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US20060232200A1 - Organic electroluminescent element - Google Patents

Organic electroluminescent element Download PDF

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Publication number
US20060232200A1
US20060232200A1 US11/392,508 US39250806A US2006232200A1 US 20060232200 A1 US20060232200 A1 US 20060232200A1 US 39250806 A US39250806 A US 39250806A US 2006232200 A1 US2006232200 A1 US 2006232200A1
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US
United States
Prior art keywords
electroluminescent element
organic
organic electroluminescent
hole transfer
layer
Prior art date
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.)
Abandoned
Application number
US11/392,508
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English (en)
Inventor
Hideki Ookawa
Junichi Tonotani
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.)
Toshiba Corp
Original Assignee
Individual
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
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Assigned to KABUSHIKI KAISHA TOSHIBA reassignment KABUSHIKI KAISHA TOSHIBA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OOKAWA, HIDEKI, TONOTANI, JUNICHI
Publication of US20060232200A1 publication Critical patent/US20060232200A1/en
Priority to US11/773,609 priority Critical patent/US7843128B2/en
Abandoned 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • 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
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof

Definitions

  • the present invention relates to an organic electroluminescent element, particularly, to an organic electroluminescent element comprising an improved organic hole transfer layer containing a polymer type organic hole transfer material.
  • the organic electroluminescent element comprises an anode, a cathode and an organic light-emitting layer interposed between the anode and the cathode and exhibiting an electric conductivity and a light-emitting capability. If voltage is applied to the organic electroluminescent element in the forward direction, holes are injected from the anode into the organic light-emitting layer and electrons are injected from the cathode into the organic light-emitting layer.
  • the organic electroluminescent element is a spontaneous light-emitting element, in which these holes and electrons are recombined within the organic light-emitting layer so as to form excitons, and then light is emitted when the excitons are relaxed. Since the organic electroluminescent element permits the process for forming a large display area having a low temperature, the organic electroluminescent element is expected to be applied to a thin film display of the next era.
  • the injection of electrons and holes from the electrodes and the mobility of the electrons and holes are controlled by arranging a plurality of layers such as a hole injection layer, a hole transfer layer, an electron transfer layer and an electron injection layer between the anode and the cathode in addition to the organic light-emitting layer.
  • Japanese Patent Application Kokai Publication No. 2004-63408 discloses a hole transfer layer formed of a polymer type hole transfer material such as a so-called “PEDOT:PSS”, which is prepared by having poly(ethylenedioxy)thiophene (DEDOT) doped with polystyrenesulphonic acid (PSS).
  • the hole transfer layer is interposed between the anode and the organic light-emitting layer, it is possible to lower the barrier wall for the hole injection, compared with the case where the holes are injected from the anode formed of a transparent electrode such as ITO directly into the organic light-emitting layer.
  • the barrier wall for the hole injection can be lowered from about 1.0 V to about 0.5 V in the case of forming a hole transfer layer between the anode and the organic light-emitting layer.
  • the organic electroluminescent element comprising the hole transfer layer is defective in that the organic light-emitting layer is deteriorated by the hole transfer layer in the current driving stage so as to shorten the life of the organic electroluminescent element.
  • an organic electroluminescent element comprising:
  • an organic hole transfer layer arranged between the anode and the organic light-emitting layer and containing a polymer type organic hole transfer material having a metal oxide of a semiconductor material or a conductive material added thereto.
  • FIG. 1 is a cross sectional view showing the construction of an organic electroluminescent diode for Example 1 of the present invention
  • FIGS. 2A and 2B are graphs each showing the current-voltage characteristics of the organic electroluminescent diode for Example 1 of the present invention.
  • FIGS. 3A and 3B are graphs each showing the current-voltage characteristics of the organic electroluminescent diode for Comparative Example 1;
  • FIG. 4 is a graph showing the changes with the driving time in the brightness and the voltage of the organic electroluminescent diode for Example 1 of the present invention.
  • FIG. 5 is a graph showing the changes with the driving time in the brightness and the voltage of the organic electroluminescent diode for Comparative Example 1.
  • the organic electroluminescent element for this embodiment is constructed such that a stacked body consisting of an organic light-emitting layer and an organic hole transfer layer is arranged between the anode and the cathode such that the organic hole transfer layer is positioned on the side of the anode.
  • the organic hole transfer layer contains a polymer type organic hole transfer material having a metal oxide of a semiconductor material or a conductive material added thereto.
  • the anode is formed of a transparent conductive material such as indium oxide doped with tin (ITO).
  • ITO indium oxide doped with tin
  • the cathode has a stacked structure comprising a layer of an alkali metal or an alkaline earth metal having a small work function, e.g., a layer of Li, Ca or Ba, and an Al layer stacked on the layer of the alkali metal or the alkaline earth metal.
  • the Al layer also acts as a protective film of the alkali metal or the alkaline earth metal that tends to be oxidized easily.
  • a cathode buffer layer made of, for example, CsF to be interposed between the cathode and the organic light-emitting layer.
  • the organic light-emitting layer is formed of a material having a polymer type polyparaphenylene vinylene skeleton or a polymer type polyfluorene skeleton.
  • the polymer type organic hole transfer material is formed of, for example, PEDOT:PSS, which is prepared by having poly (3,4-ethylenedioxy) thiophene (PEDOT) doped with polystyrenesulphonic acid or a salt thereof (PSS).
  • PEDOT:PSS polystyrenesulphonic acid or a salt thereof
  • the hole transfer material of PEDOT:PSS is soluble in water and, thus, it is possible to employ an ink jet method or a printing technology for forming a film of the organic hole transfer layer under a liquid state.
  • a metal oxide of a semiconductor material or a conductive material is added to the polymer type organic hole transfer material. It is desirable to use at least one oxide selected from the group consisting of MoO x , where x denotes an integer of 2 to 3 and VO x , where x denotes an integer of 1 to 2.5 as the metal oxide that is added to the polymer type organic hole transfer material.
  • MoO x which is excellent in electric conductivity, has a work function of about ⁇ 5 V, with the result that the hole injection from the anode made of, for example, ITO into the light-emitting layer (HOMO level of about 5.5 to 6 V) can be facilitated.
  • the organic hole transfer layer can be formed by the ink jet method or a printing technology by adding MoO x in advance to the water-soluble PEDOT:PSS.
  • the organic hole transfer layer contains a polymer type organic hole transfer material having a metal oxide of a semiconductor material or a conductive material added thereto, as described above.
  • the organic hole transfer layer contains polymer type organic hole transfer material prepared by adding at least one oxide, e.g., MoO x , selected from the group consisting of MoO x , where x denotes an integer of 2 to 3 and VO x , where x denotes an integer of 1 to 2.5 to PEDOT:PSS, it is possible to suppress or prevent the deterioration of the organic light-emitting layer during the voltage application between the anode and the cathode. It is considered reasonable to understand that the particular effect of the present invention is produced by the mechanism given below.
  • MoO x oxide
  • x denotes an integer of 2 to 3
  • VO x where x denotes an integer of 1 to 2.5 to PEDOT:PSS
  • the deterioration of the organic light-emitting layer during the voltage application is considered to be derived from the diffusion of SO3 separated from PSS in PEDOT:PSS contained in the organic hole transfer layer into the organic light-emitting layer.
  • the added MoO x enters the polymer chain of PEDOT:PSS so as to suppress the separation of SO 3 from PSS and also suppress the diffusion of the polymer chain itself containing SO 3 into the organic light-emitting layer.
  • the water soluble MoO x to enter the polymer chain of PEDOT:PSS so as to fix the polymer chain.
  • an anode was prepared by depositing ITO by a sputtering method in a thickness of, for example, 150 nm on the surface of a glass substrate, sized, for example, 24 mm square and 0.7 mm thick, followed by pattering the deposited ITO layer in the shape of a stripe. Then, prepared was an aqueous solution containing about 2% by weight of PEDOT:PSS. Also prepared was an aqueous solution containing 0.049% of MoO 3 . The aqueous solution of MoO 3 was prepared by dissolving a white powdery molybdenum oxide (MoO 3 ) in a pure water at 28° C.
  • MoO 3 white powdery molybdenum oxide
  • the PEDOT:PSS aqueous solution was mixed with the MoO 3 aqueous solution at a mixing ratio (PEDOT:PSS aqueous solution:MoO 3 aqueous solution) of 10:2 so as to obtain a mixed aqueous solution.
  • the surface of the glass substrate including the anode described above was coated with the mixed aqueous solution by a spin coating method, with the rotating speed of the glass substrate set at about 3,000 to 4,000 rpm, followed by removing the film in the region other than the light-emitting region and subsequently baking the glass substrate at 200° C. so as to form a hole transfer layer.
  • the surface of the hole transfer layer was coated with an ink prepared by dissolving a polyfluorene series blue light-emitting polymer in a tetralin solvent in a concentration of about 2%.
  • the coating was performed by a spin coating method, in which the rotating speed of the glass substrate was set at 2,000 to 3,000 rpm. Further, the resultant ink layer was baked at 150° C. so as to form an organic light-emitting layer.
  • the coating process and the baking process of the light-emitting polymer ink were carried out under a nitrogen gas atmosphere within a glove box.
  • a cathode buffer layer having a thickness of 0.5 nm and formed of CsF was formed by a resistance heating type vacuum deposition, followed by forming a Mg film 10 nm thick and an Al film 150 nm thick by the same vacuum deposition, thereby obtaining a cathode.
  • the organic electroluminescent diode thus manufactured included the glass substrate 1 having the anode 2 formed on the surface in the shape of a stripe.
  • the anode 2 was formed of an ITO layer having a thickness of, for example, 150 nm.
  • the hole transfer layer 3 prepared by adding 0.49% by weight of molybdenum oxide (MoO 3 ) to PEDOT:PSS was formed on that surface of the glass substrate 1 on which was formed the anode 2 .
  • the organic light-emitting layer 4 was formed on the surface of the hole transfer layer 3 .
  • the cathode buffer layer 5 was formed on the substrate 1 including the organic light-emitting layer 4 .
  • the cathode 6 was formed on the surface of the cathode buffer layer 5 .
  • the cover glass 8 having the drying agent 7 mounted thereto was arranged to face and to be fixed to the glass substrate 1 such that the frame-like sealing material 9 formed of a UV-curing resin was interposed between the cover glass 8 and the glass substrate 1 .
  • the region of the organic light-emitting layer 4 was sealed by the glass substrate 1 , the cover glass 8 having the drying agent mounted thereto, and the frame-like sealing material 9 .
  • An organic electroluminescent diode constructed as shown in FIG. 1 was manufactured as in Example 1, except that PEDOT:PSS alone was used for forming the hole transfer layer. In other words, a metal oxide such as MoO x was not contained in the hole transfer layer.
  • FIGS. 2A and 2B are graphs each showing the current-voltage characteristics of the diode for Example 1 comprising the hole transfer layer formed of PEDOT:PSS+MoO 3 .
  • FIGS. 3A and 3B are graphs each showing the current-voltage characteristics of the diode for Comparative Example 1 comprising the hole transfer layer formed of PEDOT:PSS alone.
  • Example 1 As apparent from FIGS. 2A, 2B , 3 A and 3 B, the diodes manufactured in Example 1 and Comparative Example 1 were found to be substantially equal to each other in the carrier current (transfer of hole in this case).
  • FIG. 4 is a graph showing the changes with time in the brightness and the voltage during the driving of the diode for Example 1 comprising the hole transfer layer formed of PEDOT:PSS+MoO 3 .
  • FIG. 5 is a graph showing the changes with time in the brightness and the voltage during the driving of the diode for Comparative Example 1 comprising the hole transfer layer formed of PEDOT:PSS alone.
  • the diode for Example 1 As apparent from FIGS. 4 and 5 , it was possible for the diode for Example 1 to suppress the deterioration of the brightness, compared with the diode for Comparative Example 1, so as to improve the life of the diode.
  • the half-life of the brightness i.e., the time required for the brightness to be lowered to half the initial brightness, for the diode for Example 1 was about 1.8 times as much as that for the diode for Comparative Example 1.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Led Devices (AREA)
US11/392,508 2005-03-31 2006-03-30 Organic electroluminescent element Abandoned US20060232200A1 (en)

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JP2005-100328 2005-03-31
JP2005100328A JP2006286664A (ja) 2005-03-31 2005-03-31 有機エレクトロルミネッセンス素子

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KR (1) KR100853897B1 (zh)
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US20100051993A1 (en) * 2008-09-03 2010-03-04 Casio Computer Co., Ltd. Light emitting apparatus and manufacturing method thereof
WO2010133449A1 (de) * 2009-05-20 2010-11-25 Siemens Aktiengesellschaft Material für eine lochtransportschicht mit p-dotierung
US20110193107A1 (en) * 2009-08-31 2011-08-11 Panasonic Corporation Light-emitter, method of manufacturing the same and light emitting device
US20120211729A1 (en) * 2009-07-31 2012-08-23 Sumitomo Chemical Company, Limited Polymer light-emitting device
US8445121B2 (en) 2005-05-20 2013-05-21 Semiconductor Energy Laboratory Co., Ltd. Light emitting element, light emitting device, and electronic device
US8921838B2 (en) 2010-08-06 2014-12-30 Panasonic Corporation Light emitting element, method for manufacturing same, and light emitting device
US8927975B2 (en) 2010-08-06 2015-01-06 Panasonic Corporation Light emitting element, method for manufacturing same, and light emitting device

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JP4910741B2 (ja) * 2007-02-08 2012-04-04 三菱化学株式会社 有機電界発光素子の製造方法
JP5618458B2 (ja) * 2007-08-10 2014-11-05 住友化学株式会社 有機エレクトロルミネッセンス素子、製造方法及び塗布液
JP4770896B2 (ja) * 2008-09-08 2011-09-14 カシオ計算機株式会社 発光装置及び発光装置の製造方法
GB201110770D0 (en) * 2011-06-24 2011-08-10 Cambridge Display Tech Ltd Process for controlling the acceptor strength of solution-processed transition metal oxides for OLED applications
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CN103500803B (zh) * 2013-10-21 2016-06-08 京东方科技集团股份有限公司 一种复合发光层及其制作方法、白光有机电致发光器件
FR3013897B1 (fr) * 2013-11-26 2017-05-12 Commissariat Energie Atomique Dispositifs electroniques organiques
CN109449316B (zh) * 2016-04-19 2020-04-17 Tcl集团股份有限公司 一种In掺杂MoO3薄膜的制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8445121B2 (en) 2005-05-20 2013-05-21 Semiconductor Energy Laboratory Co., Ltd. Light emitting element, light emitting device, and electronic device
WO2008119338A1 (de) * 2007-03-30 2008-10-09 Osram Opto Semiconductors Gmbh Organische strahlungsemittierende vorrichtung, deren verwendung sowie ein herstellungsverfahren für die vorrichtung
US20100102761A1 (en) * 2007-03-30 2010-04-29 Norwin Von Malm Organic Radiation-Emitting Device, Use Thereof and a Method of Producing the Device
US20100051993A1 (en) * 2008-09-03 2010-03-04 Casio Computer Co., Ltd. Light emitting apparatus and manufacturing method thereof
WO2010133449A1 (de) * 2009-05-20 2010-11-25 Siemens Aktiengesellschaft Material für eine lochtransportschicht mit p-dotierung
US8610113B2 (en) 2009-05-20 2013-12-17 Siemens Aktiengesellschaft Material for a hole transport layer with p-dopant
US20120211729A1 (en) * 2009-07-31 2012-08-23 Sumitomo Chemical Company, Limited Polymer light-emitting device
US20110193107A1 (en) * 2009-08-31 2011-08-11 Panasonic Corporation Light-emitter, method of manufacturing the same and light emitting device
US8378361B2 (en) 2009-08-31 2013-02-19 Panasonic Corporation Light-emitter, and light emitting device including a metal-oxide charge injection layer
US8921838B2 (en) 2010-08-06 2014-12-30 Panasonic Corporation Light emitting element, method for manufacturing same, and light emitting device
US8927975B2 (en) 2010-08-06 2015-01-06 Panasonic Corporation Light emitting element, method for manufacturing same, and light emitting device

Also Published As

Publication number Publication date
CN1841812A (zh) 2006-10-04
CN1841812B (zh) 2010-08-25
KR100853897B1 (ko) 2008-08-25
KR20060105587A (ko) 2006-10-11
JP2006286664A (ja) 2006-10-19
TWI332721B (zh) 2010-11-01
US20080007162A1 (en) 2008-01-10
US7843128B2 (en) 2010-11-30
TW200644311A (en) 2006-12-16

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