WO2007105906A1 - Organic light emitting diode having high efficiency and process for fabricating the same - Google Patents

Organic light emitting diode having high efficiency and process for fabricating the same Download PDF

Info

Publication number
WO2007105906A1
WO2007105906A1 PCT/KR2007/001245 KR2007001245W WO2007105906A1 WO 2007105906 A1 WO2007105906 A1 WO 2007105906A1 KR 2007001245 W KR2007001245 W KR 2007001245W WO 2007105906 A1 WO2007105906 A1 WO 2007105906A1
Authority
WO
WIPO (PCT)
Prior art keywords
layer
light emitting
energy level
emitting device
organic light
Prior art date
Application number
PCT/KR2007/001245
Other languages
French (fr)
Inventor
Jun-Gi Jang
Chang-Hwan Kim
Dong-Seob Jeong
Sang-Young Jeon
Kong-Kyeom Kim
Wook-Dong Cho
Ji-Eun Kim
Byung-Sun Jeon
Original Assignee
Lg Chem, 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 Lg Chem, Ltd. filed Critical Lg Chem, Ltd.
Priority to EP07715641.2A priority Critical patent/EP1994118B1/en
Priority to US12/225,096 priority patent/US8586968B2/en
Priority to JP2009500291A priority patent/JP5064482B2/en
Priority to CN2007800088294A priority patent/CN101400757B/en
Publication of WO2007105906A1 publication Critical patent/WO2007105906A1/en

Links

Classifications

    • 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
    • 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
    • H10K50/15—Hole 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]
    • H10K50/17—Carrier injection 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to an organic light emitting device having high efficiency, and a process for preparing the same. Specifically, the present invention relates to an organic light emitting device having high efficiency, in which a material with a low LUMO energy level is incorporated in a hole injecting and/or transporting layer, and to a process for preparing the same.
  • the organic light emitting device is an electronic device which emits light through the current by an applied voltage. Tang et al. report an organic light emitting device having good characteristics [Applied Physics Letters 51, p. 913, 1987]. Further, an organic light emitting device using a polymeric material, which employs the structure of the organic light emitting device as disclosed in this document, has ever been developed.
  • organic material layers in the organic light emitting device play their own roles in the processes for light emission, i.e. charge injection, charge transport, exciton formation, and light generation, respectively. Therefore, in recent years, an organic light emitting device comprising an anode (7), a hole injecting layer (6), a hole transporting layer (5), a light emitting layer (4), an electron transporting layer (3), an electron injecting layer (2), and a cathode (1), as illustrated in Fig. 1, or other organic light emitting devices having a more complex structure comprising additional layers is used.
  • the efficiency of the devices may have been increased by reducing the conductivity of the hole transporting layer because the degree of electron injection from the electron transporting layer to the light emitting layer is less than that of hole injection from the hole transporting layer to the light emitting layer [Applied Physics letters, 86, 203507, 2005].
  • an organic light emitting device having high efficiency can be obtained by forming a hole injecting and/or transporting layer of an organic light emitting device using a material with a LUMO energy level of -4 eV or less with a material with a HOMO energy level of -4 eV or less, which is ordinarily used as a hole injecting and/or transporting material.
  • the hole injecting and/or transporting layer comprises a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less, and a process for preparing the same.
  • an organic light emitting device having high efficiency can be prepared by using comprise a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material of the organic light emitting device.
  • Fig. 1 is a cross-sectional view illustrating the structure of the organic light emitting device.
  • the present invention provides an organic light emitting device comprising a first electrode, a second electrode, and at least two organic material layers interposed therebetween, including a light emitting layer, wherein the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and at least one of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises both of a material with a HOMO energy level of -4 eV or less, and a material with a LUMO energy level of -4 eV or less.
  • the present invention provides a process for preparing an organic light emitting device, comprising the steps of:
  • the step of forming the organic material layer comprises the step of forming at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and the step of forming at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises the step of forming a layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less.
  • the present invention may be characterized in that the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a h ole injecting and transporting layer, and these layers comprise a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material.
  • the HOMO energy level and the LUMO energy level can be determined using an apparatus or a calculation method known in the art.
  • the HOMO energy level can be measured using a UPS (ultra-violet pho- toemission spectroscopy) or an AC-2 equipment, manufactured by Riken Keiki Co., Ltd. (Japan).
  • the LUMO energy level can be measured using an IPES (inverse photoemission spectroscopy) or calculated by measuring a HOMO energy level and then subtracting an optical band gap from this value.
  • any one which is conventionally used as a hole injecting or transporting material can be used without any limitation.
  • a doped material with LUMO energy level of -4 eV or less on the material acts as a charge generation center. Then, the charge at the material with HOMO energy level of -4 eV or less will jump into the material with LUMO energy level of -4 eV or less to leave hole at the material with HOMO energy level of -4 eV or less, thus trapping event will be prior and regulating mobility will be secondary effect.
  • the HOMO energy level of the material is preferably -9 eV or more.
  • organic materials containing an amine group are preferably used.
  • Specific examples of the material with a HOMO energy level of -4 eV or less include N,N'-bis-(l-naphthyl)-N,N'-diphenyl-l,r-biphenyl-4,4'-diamine (NPB) (-5.5 eV), and N,N'-diphenyl-N,N'-(3-methylphenyl)-l,r-biphenyl-4,4'-diamine (TPD) (-5.2 eV), but are not limited thereto.
  • the conductivity of the hole injecting and/or transporting layer in the organic light emitting device can be controlled with the LUMO energy level. Specifically, it seems that since the material with a LUMO energy level of -4 eV or less has a LUMO energy level for trapping the holes of the material with a HOMO energy level of -4 eV or less, it may play a role in reduction in the conductivity of the hole injecting and/or transporting layer, thereby improving the efficiency of the device.
  • the kind of the material is not particularly limited, as long as it has a LUMO energy level of -4 eV or less. It is more preferable that the material with a LUMO energy level of -4 eV or less has a LUMO energy level of -5 eV or less. Further, it is more preferable that the material has a LUMO energy level of -9 eV or more. If the material has a LUMO energy level within the above-described range, it is in balance with a material with a HOMO energy level of -4 eV or less, and the efficiency of the device can be further improved by suitably reducing the conductivity of the hole injecting and/or transporting layer.
  • F4TCNQ 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
  • F4TCNQ fluorine-substituted 3,4,9, 10-perylenetetracarboxylic dianhydride
  • PTCDA cyano-substituted PTCDA
  • NTCDA naphthalenetetracaboxylic dianhydride
  • fluorine-substituted NTCDA cyano-substituted NTCDA
  • HAT hexanitrile hexaazatriphenylene
  • HAT hex aazat- riphenylene hexacarbonnitrile
  • the ratio of the material with a HOMO energy level of -4 eV or less and the material with a LUMO energy level of -4 eV or less in the hole injecting and/or transporting layer is not particularly limited, but two materials can be used at a ratio which leads to a higher drive voltage than the drive voltage in the case of each material alone.
  • This mixing ratio can be selected according to the kind of the material to be used, the conditions for man- ufactuing or driving the device, or the like by a skilled person in the art.
  • hexaazatriphenylene hexacarbonnitrile can be mixed in a proportion ranging from 20 vol% to 80 vol% as a material with a LUMO energy level of -4 eV or less.
  • the method for forming a hole injecting and/or transporting layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less layer is not particularly limited, and any method known in the art can be employed.
  • the hole injecting and/or transporting layer can be formed by mixing the above-described materials and coating it in a solution process, or depositing the above-described materials togther, or by other methods. Examples of the coating method include spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes, but are not limited thereto.
  • the thickness of the layer comprising the material with a HOMO energy level of -4 eV or less and the material with a LUMO energy level of -4 eV or less is preferably 1 nm to 100 nm, and more preferably 10 nm to 60 nm.
  • the organic light emitting device can have a structure known in the art, except that its hole injecting and/or transporting layer comprises a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material.
  • the hole injecting and/or transporting layer can further comprise an inorganic material.
  • the inorganic material is preferably a metal or a metal oxide.
  • the work function of the inorganic material is desirably 6 eV or less, and more preferably 2.5 eV or more and 6 eV or less. Examples of the inorganic material having a work function of 6 eV or less include Au(5.1 eV), Pt(5.6 eV), Al(4.2 eV), Ag(4.2 eV), and Li(2.9 eV).
  • the organic light emitting device has a structure comprising a first electrode, a second electrode and organic material layers interposed therebetween, wherein the organic material layers can comprise only a hole injecting and/or transporting layer and a light emitting layer, or further comprise at least one layer selected from additional organic material layers, such as an electron transporting layer, an electron injecting layer, a hole or electron shielding layer, and a buffer layer.
  • the organic light emitting device of the present invention may have a structure, in which a substrate, a hole injecting electrode, a hole injecting and/or transporting layer, a light emitting layer, an electron transporting layer and an electron injecting electrode are subsequently laminated.
  • the organic light emitting device having such structure is referred to as an organic light emitting device having a forward structure.
  • the present invention is not limited thereto, but it also includes an organic light emitting device having a reverse structure. That is, the organic light emitting device of the present invention can have a structure in which a substrate, an electron injecting electrode, an electron transporting layer, a light emitting layer, a hole injecting and/or transporting layer and a hole injecting electrode are sequentially laminated.
  • the process for preparing the organic light emitting device comprises the steps of preparing a first electrode; forming at least two organic material layers including a light emitting layer on the first electrode; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer comprises the step of forming at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and the step of forming at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises the step of forming a layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less.
  • the organic light emitting device according to the present invention can be prepared by usual methods and materials known in the art, except that the hole injecting and/or transporting layer may be formed using a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material.
  • the organic light emitting device according to the present invention can be prepared by depositing a metal, or a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) process such as sputtering or e-beam evaporation to form an anode; forming organic material layers on the anode; and depositing a material, which can be used as a cathode, thereon.
  • a PVD physical vapor deposition
  • an organic light emitting device can be prepared by depositing a cathode material, an organic material layer, and an anode material on a substrate, as described above to prepare an organic light emitting device having a reverse structure.
  • the organic material layer in the organic light emitting device according to the present invention can be produced to have a fewer number of layers, by using a variety of polymeric materials, by means of a solvent process rather than a deposit process, such as spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes.
  • the hole injecting electrode material in the organic light emitting device according to the present invention may be preferably a material having a large work function to facilitate hole injection usually to the organic material layers.
  • Specific examples of the hole injecting electrode material which can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium-tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al and SnO :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-l,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
  • the electron injecting electrode material in the organic light emitting device according to the present invention may be preferably a material having a small work function to facilitate electron injection usually to the organic material layers.
  • the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an alloy thereof; multilayer structure materials such as LiF/Al and LiO /Al, but are not limited thereto.
  • the light emitting material are a material capable of emitting visible light by accepting and recombining holes from the hole transporting layer and electrons from the electron transporting layer, preferably a material having high quantum efficiency for fluorescence or phosphorescence.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (AIq ); compounds of carbazole series; dimerized styryl compounds; BAIq; 10-hydroxybenzoquinoline-metal compounds; compounds of benzoxazole, benzthiazole and benzimidazole series; polymers of poly(p-phenylenevinylene) (PPV) series; spiro compounds; and compounds of polyfluorene and rubrene series, but are not limited thereto.
  • AIq 8-hydroxyquinoline aluminum complex
  • PV poly(p-phenylenevinylene) series
  • spiro compounds and compounds of polyfluorene and rubrene series, but are not limited thereto.
  • the electron transporting material may be suitably a material having high electron mobility, which can transfer electrons from the electron injecting electrode) to the light emitting layer.
  • Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes including AIq ; organic radical compounds; and hydroxy flavone-metal complexes, but are not limited thereto.
  • a transparent electrode indium tin oxide was deposited on a glass substrate to a thickness of 100 nm for a hole injecting electrode, to which heat was applied in vacuo.
  • the compound of the following formula 1 (HOMO: about -5.33 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile (LUMO: about -5.5 to - 6 eV) was deposited thereon to a thickness of 60 nm for a hole injecting and transporting layer.
  • N,N'-bis-(l -naphthyl)-N,N'-diphenyl- 1 , 1 '-biphenyl-4,4'-diamine was deposited thereon to a thickness of 20 nm for a hole transporting and electron shielding layer.
  • Tris(8-hydroxyquinolino) aluminum (AIq ) and 10-(2-benzothiazolyl)-l,l,7,7-tetramethyl-2,3,6,7-tetrahydro-lH,5H,llH-[l]benzopyra no[6,7,8-ij]-quinolizin-l 1-one) (C545t) were deposited thereon to a thickness of 25 nm for a light emitting layer.
  • Tris(8-hydroxyquinolino)aluminum (AIq ) was deposited thereon to a thickness of 25 nm for an electron transporting and injecting layer.
  • LiF was deposited thereon to a thickness of 1 nm for an electron injecting layer, and then aluminum (Al) was deposited thereon to a thickness of 150 nm for an electron injecting electrode, thereby preparing an organic light emitting device.
  • the prepared device had a voltage of 10.97 V and an efficiency of 9.92 cd/A at a current density of 100 mA/cm .
  • Example 2 An organic light emitting device was prepared in the same manner as in Example 1, except that deposition was conducted to give the thickness of the hole injecting and transporting layer of 10 nm, and to give the thickness of the hole transporting and electron shielding layer of 40 nm.
  • the prepared device had a voltage of 7 V and an efficiency of 9.95 cd/A at a current density of 100 mA/cm .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that NPB (HOMO: about -5.5 eV) which had been doped with 40 vol% of hex- aazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • NPB HOMO: about -5.5 eV
  • the prepared device had a voltage of 7.73 V and an efficiency of 10.11 cd/A at a current density of 100 mA/cm .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 2 (HOMO: about -5.3 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • HOMO -5.3 eV
  • the prepared device had a voltage of 7.2 V and an efficiency of 9.5 cd/A at a current density of 100 mA/cm 2 .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 3 (HOMO: about -5.2 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • HOMO -5.2 eV
  • the prepared device had a voltage of 6.9 V and an efficiency of 9.4 cd/A at a current density of 100 mA/cm .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 4 (HOMO: about -5.4 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • HOMO -5.4 eV
  • the prepared device had a voltage of 8 V and an efficiency of 10.6 cd/A at a current density of 100 mA/cm .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 5 (HOMO: about -5.4 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • HOMO -5.4 eV
  • the prepared device had a voltage of 7.4 V and an efficiency of 9.8 cd/A at a current density of 100 mA/cm 2 .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the NPB material (HOMO: about -5.5 eV) which had been doped with 40 vol% of the compound of the following formula 6 (LUMO: about -5.0 eV to -5.3 eV) was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
  • the NPB material HOMO: about -5.5 eV
  • LUMO about -5.0 eV to -5.3 eV
  • An organic light emitting device was prepared in the same manner as in Example 1, except that only the compound of the formula 1 was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
  • the prepared device had a voltage of 6.93 V and an efficiency of 7.74 cd/A at a current density of 100 mA/cm .
  • Comparative Example 2 An organic light emitting device was prepared in the same manner as in Example 1, except that only the NPB material was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
  • the prepared device had a voltage 7.55 V and an efficiency of 8.5 cd/A at a current density of 100 mA/cm .
  • An organic light emitting device was prepared in the same manner as in Example 1, except that only hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
  • the prepared device had a voltage 6.3 V and an efficiency of 6.9 cd/A at a current density of 100 mA/cm .
  • Example 2 exhibited excellent effects in terms of voltage and efficiency, as compared with the device of Comparative Example 1.

Landscapes

  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention provides an organic light emitting device comprising a first electrode, a second electrode, and at least two organic material layers interposed therebetween, including a light emitting layer, wherein the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and at least one of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises a material with a HOMO energy level of -4 eV or less, and a material with a LUMO energy level of -4 eV or less, and a process for preparing the same.

Description

Description
ORGANIC LIGHT EMITTING DIODE HAVING HIGH EFFICIENCY AND PROCESS FOR FABRICATING THE SAME
Technical Field
[1] The present invention relates to an organic light emitting device having high efficiency, and a process for preparing the same. Specifically, the present invention relates to an organic light emitting device having high efficiency, in which a material with a low LUMO energy level is incorporated in a hole injecting and/or transporting layer, and to a process for preparing the same.
[2] This application claims priority benefits from Korean Patent Application No.
10-2006-0023608, filed on March 14, 2006, the entire contents of which are fully incorporated herein by reference. Background Art
[3] The organic light emitting device is an electronic device which emits light through the current by an applied voltage. Tang et al. report an organic light emitting device having good characteristics [Applied Physics Letters 51, p. 913, 1987]. Further, an organic light emitting device using a polymeric material, which employs the structure of the organic light emitting device as disclosed in this document, has ever been developed.
[4] The essential point of the prior art is that the organic material layers in the organic light emitting device play their own roles in the processes for light emission, i.e. charge injection, charge transport, exciton formation, and light generation, respectively. Therefore, in recent years, an organic light emitting device comprising an anode (7), a hole injecting layer (6), a hole transporting layer (5), a light emitting layer (4), an electron transporting layer (3), an electron injecting layer (2), and a cathode (1), as illustrated in Fig. 1, or other organic light emitting devices having a more complex structure comprising additional layers is used.
[5] Studies on doping various materials for improving the conductivity of the organic material for a hole injecting layer, a hole transporting layer, an electron transporting layer, and an electron injecting layer in the organic light emitting device have been conducted. See, Japanese Patent Application Publication No. 2000-196140, [Applied Physics Letters, 73, p. 729-731 (1998)], [Applied Physics Letters, 72, pp. 2147-2149 (1998)], U.S. Patent No. 5,093,698, and International Patent Application Publication WO 01/67825.
[6] The above documents proposed embodiments of devices having high efficiency simply by increasing the conductivity of the charge transporting layer or the charge injecting layer through doping. For example, International Patent Application Publication WO 01/67825 describes that the hole conductivity in the case of p-doping with a stable organic molecular material of an acceptor type having a high molecular weight of 200 g/mol or more on a hole transporting layer (at a low doping concentration of 1 : 110 to 10000) is further increased than those in the case of not applying such the procedure. Similarly, it is also described that by n-doping with a stable organic molecular material of a donor type having a high molecular weight on an electron transporting layer, the similar results can be obtained.
[7] Meanwhile, in the currently available organic light emitting devices, the efficiency of the devices may have been increased by reducing the conductivity of the hole transporting layer because the degree of electron injection from the electron transporting layer to the light emitting layer is less than that of hole injection from the hole transporting layer to the light emitting layer [Applied Physics letters, 86, 203507, 2005].
[8] However, this document describes that a hole injecting layer having a small energy band gap [copper phthalocyanine (CuPC), HOMO: -5.1 eV, LUMO: -3 eV] is doped on a hole transporting layer having a high energy band gap
[N,N'-bis-(l-naphthyl)-N,N'-diphenyl-l,r-biphenyl-4,4'-diamine (NPB), HOMO: -5.5 eV, LUMO: -2.4 eV]. In these devices, the increase in the efficiency is resulted from increasing the efficiency in proportion to the ratio of the holes and the charges injected to a light emitting layer by trapping the holes using the HOMO (highest occupied molecular orbital) energy level of CuPC. Disclosure of Invention Technical Problem
[9] The present inventor have found that an organic light emitting device having high efficiency can be obtained by forming a hole injecting and/or transporting layer of an organic light emitting device using a material with a LUMO energy level of -4 eV or less with a material with a HOMO energy level of -4 eV or less, which is ordinarily used as a hole injecting and/or transporting material.
Technical Solution
[10] Thus, it is an object of the present invention to provide an organic light emitting device, in which the hole injecting and/or transporting layer comprises a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less, and a process for preparing the same. Advantageous Effects
[11] In the present invention, an organic light emitting device having high efficiency can be prepared by using comprise a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material of the organic light emitting device.
Brief Description of the Drawings
[12] Fig. 1 is a cross-sectional view illustrating the structure of the organic light emitting device.
[13] * Reference Numerals *
[14] Cathode (1),
[15] Electron injecting layer (2),
[16] Electron transporting layer (3),
[17] Light emitting layer (4),
[ 18] Hole transporting layer (5),
[19] Hole injecting layer (6), and
[20] Anode (7).
Best Mode for Carrying Out the Invention
[21] The present invention provides an organic light emitting device comprising a first electrode, a second electrode, and at least two organic material layers interposed therebetween, including a light emitting layer, wherein the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and at least one of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises both of a material with a HOMO energy level of -4 eV or less, and a material with a LUMO energy level of -4 eV or less.
[22] Further, the present invention provides a process for preparing an organic light emitting device, comprising the steps of:
[23] preparing a first electrode;
[24] forming at least two organic material layers including a light emitting layer on the first electrode; and
[25] forming a second electrode on the organic material layer,
[26] wherein the step of forming the organic material layer comprises the step of forming at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and the step of forming at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises the step of forming a layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less.
[27] Hereinbelow, the present invention will be described in detail.
[28] The present invention may be characterized in that the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a h ole injecting and transporting layer, and these layers comprise a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material.
[29] In the present invention, the HOMO energy level and the LUMO energy level can be determined using an apparatus or a calculation method known in the art. For example, the HOMO energy level can be measured using a UPS (ultra-violet pho- toemission spectroscopy) or an AC-2 equipment, manufactured by Riken Keiki Co., Ltd. (Japan). Further, the LUMO energy level can be measured using an IPES (inverse photoemission spectroscopy) or calculated by measuring a HOMO energy level and then subtracting an optical band gap from this value.
[30] In the present invention, as the material with a HOMO energy level of -4 eV or less, any one which is conventionally used as a hole injecting or transporting material can be used without any limitation.
[31] Limitation of HOMO energy level is based on contact electrode work function.
Therefore, if the material with HOMO energy level of -4 eV or less is used, a doped material with LUMO energy level of -4 eV or less on the material acts as a charge generation center. Then, the charge at the material with HOMO energy level of -4 eV or less will jump into the material with LUMO energy level of -4 eV or less to leave hole at the material with HOMO energy level of -4 eV or less, thus trapping event will be prior and regulating mobility will be secondary effect.
[32] Further, the HOMO energy level of the material is preferably -9 eV or more. As the hole injecting or transporting material, organic materials containing an amine group are preferably used.
[33] Specific examples of the material with a HOMO energy level of -4 eV or less include N,N'-bis-(l-naphthyl)-N,N'-diphenyl-l,r-biphenyl-4,4'-diamine (NPB) (-5.5 eV), and N,N'-diphenyl-N,N'-(3-methylphenyl)-l,r-biphenyl-4,4'-diamine (TPD) (-5.2 eV), but are not limited thereto.
[34] In the present invention, for the material with a LUMO energy level of -4 eV or less, the conductivity of the hole injecting and/or transporting layer in the organic light emitting device can be controlled with the LUMO energy level. Specifically, it seems that since the material with a LUMO energy level of -4 eV or less has a LUMO energy level for trapping the holes of the material with a HOMO energy level of -4 eV or less, it may play a role in reduction in the conductivity of the hole injecting and/or transporting layer, thereby improving the efficiency of the device.
[35] In the present invention, the kind of the material is not particularly limited, as long as it has a LUMO energy level of -4 eV or less. It is more preferable that the material with a LUMO energy level of -4 eV or less has a LUMO energy level of -5 eV or less. Further, it is more preferable that the material has a LUMO energy level of -9 eV or more. If the material has a LUMO energy level within the above-described range, it is in balance with a material with a HOMO energy level of -4 eV or less, and the efficiency of the device can be further improved by suitably reducing the conductivity of the hole injecting and/or transporting layer.
[36] Specific examples of the material include
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9, 10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracaboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexanitrile hexaazatriphenylene (HAT), and hex aazat- riphenylene hexacarbonnitrile, but are not limited thereto.
[37] In the organic light emitting device of the present invention, the ratio of the material with a HOMO energy level of -4 eV or less and the material with a LUMO energy level of -4 eV or less in the hole injecting and/or transporting layer is not particularly limited, but two materials can be used at a ratio which leads to a higher drive voltage than the drive voltage in the case of each material alone. This mixing ratio can be selected according to the kind of the material to be used, the conditions for man- ufactuing or driving the device, or the like by a skilled person in the art. For example, in the case of using NPB as a material with a HOMO energy level of -4 eV or less, hexaazatriphenylene hexacarbonnitrile can be mixed in a proportion ranging from 20 vol% to 80 vol% as a material with a LUMO energy level of -4 eV or less.
[38] The method for forming a hole injecting and/or transporting layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less layer is not particularly limited, and any method known in the art can be employed. For example, the hole injecting and/or transporting layer can be formed by mixing the above-described materials and coating it in a solution process, or depositing the above-described materials togther, or by other methods. Examples of the coating method include spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes, but are not limited thereto.
[39] In the organic light emitting device according to the present invention, the thickness of the layer comprising the material with a HOMO energy level of -4 eV or less and the material with a LUMO energy level of -4 eV or less is preferably 1 nm to 100 nm, and more preferably 10 nm to 60 nm.
[40] The organic light emitting device according to the present invention can have a structure known in the art, except that its hole injecting and/or transporting layer comprises a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material. [41] In the organic light emitting device according to the present invention, the hole injecting and/or transporting layer can further comprise an inorganic material. The inorganic material is preferably a metal or a metal oxide. The work function of the inorganic material is desirably 6 eV or less, and more preferably 2.5 eV or more and 6 eV or less. Examples of the inorganic material having a work function of 6 eV or less include Au(5.1 eV), Pt(5.6 eV), Al(4.2 eV), Ag(4.2 eV), and Li(2.9 eV).
[42] The organic light emitting device according to the present invention has a structure comprising a first electrode, a second electrode and organic material layers interposed therebetween, wherein the organic material layers can comprise only a hole injecting and/or transporting layer and a light emitting layer, or further comprise at least one layer selected from additional organic material layers, such as an electron transporting layer, an electron injecting layer, a hole or electron shielding layer, and a buffer layer.
[43] For example, the organic light emitting device of the present invention may have a structure, in which a substrate, a hole injecting electrode, a hole injecting and/or transporting layer, a light emitting layer, an electron transporting layer and an electron injecting electrode are subsequently laminated. The organic light emitting device having such structure is referred to as an organic light emitting device having a forward structure. However, the present invention is not limited thereto, but it also includes an organic light emitting device having a reverse structure. That is, the organic light emitting device of the present invention can have a structure in which a substrate, an electron injecting electrode, an electron transporting layer, a light emitting layer, a hole injecting and/or transporting layer and a hole injecting electrode are sequentially laminated.
[44] The process for preparing the organic light emitting device according to the present invention comprises the steps of preparing a first electrode; forming at least two organic material layers including a light emitting layer on the first electrode; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer comprises the step of forming at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and the step of forming at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises the step of forming a layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less.
[45] The organic light emitting device according to the present invention can be prepared by usual methods and materials known in the art, except that the hole injecting and/or transporting layer may be formed using a material with a LUMO energy level of -4 eV or less, as well as a material with a HOMO energy level of -4 eV or less which is conventionally used as a hole injecting and/or transporting material. [46] For example, the organic light emitting device according to the present invention can be prepared by depositing a metal, or a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) process such as sputtering or e-beam evaporation to form an anode; forming organic material layers on the anode; and depositing a material, which can be used as a cathode, thereon. Alternatively, an organic light emitting device can be prepared by depositing a cathode material, an organic material layer, and an anode material on a substrate, as described above to prepare an organic light emitting device having a reverse structure.
[47] The organic material layer in the organic light emitting device according to the present invention can be produced to have a fewer number of layers, by using a variety of polymeric materials, by means of a solvent process rather than a deposit process, such as spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes.
[48] The hole injecting electrode material in the organic light emitting device according to the present invention may be preferably a material having a large work function to facilitate hole injection usually to the organic material layers. Specific examples of the hole injecting electrode material which can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium-tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al and SnO :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-l,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
[49] The electron injecting electrode material in the organic light emitting device according to the present invention may be preferably a material having a small work function to facilitate electron injection usually to the organic material layers. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an alloy thereof; multilayer structure materials such as LiF/Al and LiO /Al, but are not limited thereto.
[50] The light emitting material are a material capable of emitting visible light by accepting and recombining holes from the hole transporting layer and electrons from the electron transporting layer, preferably a material having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (AIq ); compounds of carbazole series; dimerized styryl compounds; BAIq; 10-hydroxybenzoquinoline-metal compounds; compounds of benzoxazole, benzthiazole and benzimidazole series; polymers of poly(p-phenylenevinylene) (PPV) series; spiro compounds; and compounds of polyfluorene and rubrene series, but are not limited thereto.
[51] The electron transporting material may be suitably a material having high electron mobility, which can transfer electrons from the electron injecting electrode) to the light emitting layer. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes including AIq ; organic radical compounds; and hydroxy flavone-metal complexes, but are not limited thereto. Mode for the Invention
[52] Hereinafter, the present invention will be described in more detail by means of
Examples. The following Examples are provided for exemplifying the invention, and it should not be construed that the scope of the invention is limited thereto.
[53] Example 1
[54] A transparent electrode (indium tin oxide) was deposited on a glass substrate to a thickness of 100 nm for a hole injecting electrode, to which heat was applied in vacuo. The compound of the following formula 1 (HOMO: about -5.33 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile (LUMO: about -5.5 to - 6 eV) was deposited thereon to a thickness of 60 nm for a hole injecting and transporting layer. N,N'-bis-(l -naphthyl)-N,N'-diphenyl- 1 , 1 '-biphenyl-4,4'-diamine (NPB) was deposited thereon to a thickness of 20 nm for a hole transporting and electron shielding layer. Tris(8-hydroxyquinolino) aluminum (AIq ) and 10-(2-benzothiazolyl)-l,l,7,7-tetramethyl-2,3,6,7-tetrahydro-lH,5H,llH-[l]benzopyra no[6,7,8-ij]-quinolizin-l 1-one) (C545t) were deposited thereon to a thickness of 25 nm for a light emitting layer. Tris(8-hydroxyquinolino)aluminum (AIq ) was deposited thereon to a thickness of 25 nm for an electron transporting and injecting layer. LiF was deposited thereon to a thickness of 1 nm for an electron injecting layer, and then aluminum (Al) was deposited thereon to a thickness of 150 nm for an electron injecting electrode, thereby preparing an organic light emitting device.
[55] The prepared device had a voltage of 10.97 V and an efficiency of 9.92 cd/A at a current density of 100 mA/cm .
[56] [Formula 1]
[57]
Figure imgf000009_0001
[58] Example 2 [59] An organic light emitting device was prepared in the same manner as in Example 1, except that deposition was conducted to give the thickness of the hole injecting and transporting layer of 10 nm, and to give the thickness of the hole transporting and electron shielding layer of 40 nm.
[60] The prepared device had a voltage of 7 V and an efficiency of 9.95 cd/A at a current density of 100 mA/cm .
[61] Example 3
[62] An organic light emitting device was prepared in the same manner as in Example 1, except that NPB (HOMO: about -5.5 eV) which had been doped with 40 vol% of hex- aazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
[63] The prepared device had a voltage of 7.73 V and an efficiency of 10.11 cd/A at a current density of 100 mA/cm .
[64] Example 4
[65] An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 2 (HOMO: about -5.3 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
[66] [Formula 2]
[67]
Figure imgf000010_0001
[68] The prepared device had a voltage of 7.2 V and an efficiency of 9.5 cd/A at a current density of 100 mA/cm2.
[69] Example 5
[70] An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 3 (HOMO: about -5.2 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm. [71] [Formula 3]
[72]
Figure imgf000011_0001
[73] The prepared device had a voltage of 6.9 V and an efficiency of 9.4 cd/A at a current density of 100 mA/cm .
[74] Example 6
[75] An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 4 (HOMO: about -5.4 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
[76] [Formula 4]
[77]
Figure imgf000011_0002
[78] The prepared device had a voltage of 8 V and an efficiency of 10.6 cd/A at a current density of 100 mA/cm .
[79] Example 7
[80] An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of the following formula 5 (HOMO: about -5.4 eV) which had been doped with 40 vol% of hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
[81] [Formula 5]
[82]
Figure imgf000012_0001
[83] The prepared device had a voltage of 7.4 V and an efficiency of 9.8 cd/A at a current density of 100 mA/cm2.
[84] Example 8
[85] An organic light emitting device was prepared in the same manner as in Example 1, except that the NPB material (HOMO: about -5.5 eV) which had been doped with 40 vol% of the compound of the following formula 6 (LUMO: about -5.0 eV to -5.3 eV) was deposited to a thickness of 10 nm for the hole injecting and transporting layer, and deposition was conducted to give the thickness of the hole transporting and electron shielding layer of 30 nm.
[86] [Formula 6]
[87]
Figure imgf000012_0002
[88] The prepared device had a voltage of 8.4 V and an efficiency of 9.5 cd/A at a current density of 100 mA/cm . [89] Comparative Example 1
[90] An organic light emitting device was prepared in the same manner as in Example 1, except that only the compound of the formula 1 was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
[91] The prepared device had a voltage of 6.93 V and an efficiency of 7.74 cd/A at a current density of 100 mA/cm . [92] Comparative Example 2 [93] An organic light emitting device was prepared in the same manner as in Example 1, except that only the NPB material was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
[94] The prepared device had a voltage 7.55 V and an efficiency of 8.5 cd/A at a current density of 100 mA/cm .
[95] Comparative Example 3
[96] An organic light emitting device was prepared in the same manner as in Example 1, except that only hexaazatriphenylene hexacarbonnitrile was deposited to a thickness of 60 nm for the hole injecting and transporting layer.
[97] The prepared device had a voltage 6.3 V and an efficiency of 6.9 cd/A at a current density of 100 mA/cm .
[98]
[99] The results from Examples 1 to 8 confirmed that in the organic light emitting device, if a hole injecting and/or transporting layer is formed by using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less in combination, a device having good efficiency can be established.
[100] In comparison between the results from Comparative Examples 1 and 3 and the results from Example 1, between the results from Comparative Example 2 and the results from Example 3, the devices of Examples in which the above-mentioned two materials were used as the materials for the hole injecting and/or transporting layer exhibited beneficial characteristics in terms of efficiency, as compared with the devices of Comparative Examples in which only one material was used as the material for hole injecting and transporting layer.
[101] The device of Example 2 exhibited excellent effects in terms of voltage and efficiency, as compared with the device of Comparative Example 1.

Claims

Claims
[1] An organic light emitting device comprising a first electrode, a second electrode, and at least two organic material layers interposed therebetween, including a light emitting layer, wherein the organic material layers comprise at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and at least one of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises both of a material with a HOMO energy level of -4 eV or less, and a material with a LUMO energy level of -4 eV or less.
[2] The organic light emitting device according to claim 1, wherein the material with a HOMO energy level of -4 eV or less includes an organic material containing an amine group.
[3] The organic light emitting device according to claim 1, wherein the material with a HOMO energy level of -4 eV or less has a HOMO energy level of -9 eV or more.
[4] The organic light emitting device according to claim 1, wherein the material with a LUMO energy level of -4 eV or less has a LUMO energy level of -9 eV or more.
[5] The organic light emitting device according to claim 1, wherein the material with a LUMO energy level of -4 eV or less includes at least one selected from the group consisting of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracaboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexanitrile hexaazatriphenylene (HAT), and hexaazatriphenylene hexacarbonnitrile.
[6] The organic light emitting device according to claim 1, wherein the material with a LUMO energy level of -4 eV or less is hexaazatriphenylene hexacarbonnitrile.
[7] The organic light emitting device according to claim 1, wherein at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer further comprises an inorganic material.
[8] The organic light emitting device according to claim 7, wherein the inorganic material is a metal or a metal oxide.
[9] The organic light emitting device according to claim 7, wherein the inorganic material has a work function of 2.5 eV or more and 6 eV or less.
[10] The organic light emitting device according to claim 1, having a forward structure, in which a hole injecting electrode, at least two organic material layers including a light emitting layer, and an electron injecting electrode are se- quentially laminated from the bottom.
[11] The organic light emitting device according to claim 1, having a reverse structure, in which an electron injecting electrode, at least two organic material layers including a light emitting layer, and a hole injecting electrode are sequentially laminated from the bottom.
[12] The organic light emitting device according to claim 1, wherein the organic material layers comprise at least one layer selected from an electron injecting layer, an electron transporting layer, an electron injecting and transporting layer, an electron shielding layer, a hole shielding layer and a buffer layer.
[13] A process for preparing an organic light emitting device, comprising the steps of: preparing a first electrode; forming at least two organic material layers including a light emitting layer on the first electrode; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer comprises the step of forming at least one layer of a hole injecting layer, a hole transporting layer and a hole injecting and transporting layer, and the step of forming at least one layer of the hole injecting layer, the hole transporting layer and the hole injecting and transporting layer comprises the step of forming a layer using a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less.
[14] The process for preparing an organic light emitting device according to claim 13, wherein the material with a HOMO energy level of -4 eV or less includes an organic material containing an amine group.
[15] The process for preparing an organic light emitting device according to claim 13, wherein the material with a HOMO energy level of -4 eV or less has a HOMO energy level of -9 eV or more.
[16] The process for preparing an organic light emitting device according to claim 13, wherein the material with a LUMO energy level of -4 eV or less has a LUMO energy level of -9 eV or more.
[17] The process for preparing an organic light emitting device according to claim 13, wherein the material with a LUMO energy level of -4 eV or less includes at least one selected from the group consisting of
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine- substituted 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano- substituted PTCDA, naphthalenetetracaboxylic dianhydride (NTCDA), fluorine- substituted NTCDA, cyano-substituted NTCDA, hexanitrile hexaazatriphenylene (HAT), and hexaazatriphenylene hexacarbonnitrile. [18] The process for preparing an organic light emitting device according to claim 13, wherein the step of forming a layer using the material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less is carried out by spin coating, dip coating, doctor blading, screen printing, ink jet printing, or heat transfer processes.
PCT/KR2007/001245 2006-03-14 2007-03-14 Organic light emitting diode having high efficiency and process for fabricating the same WO2007105906A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP07715641.2A EP1994118B1 (en) 2006-03-14 2007-03-14 Organic light emitting diode having high efficiency and process for fabricating the same
US12/225,096 US8586968B2 (en) 2006-03-14 2007-03-14 Organic light emitting diode having high efficiency and process for fabricating the same
JP2009500291A JP5064482B2 (en) 2006-03-14 2007-03-14 High-efficiency organic light-emitting device and manufacturing method thereof
CN2007800088294A CN101400757B (en) 2006-03-14 2007-03-14 Organic light emitting diode having high efficiency and process for fabricating the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20060023608 2006-03-14
KR10-2006-0023608 2006-03-14

Publications (1)

Publication Number Publication Date
WO2007105906A1 true WO2007105906A1 (en) 2007-09-20

Family

ID=38509692

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2007/001245 WO2007105906A1 (en) 2006-03-14 2007-03-14 Organic light emitting diode having high efficiency and process for fabricating the same

Country Status (7)

Country Link
US (1) US8586968B2 (en)
EP (1) EP1994118B1 (en)
JP (2) JP5064482B2 (en)
KR (1) KR100823443B1 (en)
CN (1) CN101400757B (en)
TW (1) TWI376980B (en)
WO (1) WO2007105906A1 (en)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009277791A (en) * 2008-05-13 2009-11-26 Fuji Electric Holdings Co Ltd Organic el element
WO2010058737A1 (en) * 2008-11-19 2010-05-27 ソニー株式会社 Organic electroluminescent element and display device
WO2010150792A1 (en) * 2009-06-23 2010-12-29 住友化学株式会社 Organic electroluminescent element
EP2299786A2 (en) * 2008-05-16 2011-03-23 LG Chem, Ltd. Stacked organic light-emitting diode
WO2011119162A1 (en) * 2010-03-25 2011-09-29 Universal Display Corporation Solution processable doped triarylamine hole injection materials
EP2430677A1 (en) * 2009-05-13 2012-03-21 Global OLED Technology LLC Internal connector for organic electronic devices
JP2012508975A (en) * 2008-11-13 2012-04-12 エルジー・ケム・リミテッド Low voltage driving organic light emitting device and method for manufacturing the same
WO2013011954A1 (en) 2011-07-15 2013-01-24 国立大学法人九州大学 Organic electroluminescence element and compound used therein
WO2013191429A1 (en) * 2012-06-18 2013-12-27 주식회사 엘지화학 Nitrogen-containing heterocyclic compound and organic electronic element comprising same
EP2372805A3 (en) * 2010-04-01 2014-05-07 Samsung Display Co., Ltd. Organic light emitting diode device
KR20160055675A (en) 2014-11-07 2016-05-18 삼성디스플레이 주식회사 Organic electroluminescence device
KR20160067021A (en) 2014-12-02 2016-06-13 삼성디스플레이 주식회사 Organic electroluminescence device
KR20160067728A (en) 2014-12-03 2016-06-14 삼성디스플레이 주식회사 Organic electroluminescence device
KR20160148437A (en) 2015-06-15 2016-12-26 삼성디스플레이 주식회사 Organic electroluminescence device
KR20170000741A (en) 2015-06-23 2017-01-03 삼성디스플레이 주식회사 Organic electroluminescence device
US9660202B2 (en) 2013-12-27 2017-05-23 Samsung Display Co., Ltd. Organic electroluminescence device
US9966536B2 (en) 2014-09-09 2018-05-08 Samsung Display Co., Ltd. Organic electroluminescence device
US9997715B2 (en) 2014-11-18 2018-06-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US10090475B2 (en) 2014-10-06 2018-10-02 Samsung Display Co., Ltd. Organic electroluminescent device
CN109415377A (en) * 2016-07-01 2019-03-01 株式会社Lg化学 Compound and organic electronic element comprising it
US10930854B2 (en) 2014-08-11 2021-02-23 Samsung Display Co., Ltd. Monoamine material for organic electroluminescent element, and organic electroluminescent element using same

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100894627B1 (en) 2008-01-15 2009-04-24 삼성모바일디스플레이주식회사 Organic light emitting diode and fabrication method for the same
KR100922758B1 (en) * 2008-02-20 2009-10-21 삼성모바일디스플레이주식회사 An organic light emitting device
JP4807366B2 (en) * 2008-03-11 2011-11-02 ソニー株式会社 Display device
CN101734173B (en) 2008-11-26 2013-08-28 比亚迪股份有限公司 Control system and method of motor gear
WO2011024348A1 (en) * 2009-08-24 2011-03-03 シャープ株式会社 Organic electroluminescent element, organic electroluminescent display device, organic electroluminescent illuminating device, and method for manufacturing organic electroluminescent element
KR101137388B1 (en) * 2009-11-13 2012-04-20 삼성모바일디스플레이주식회사 Organic light-emitting device
EP2628198B1 (en) * 2010-10-15 2016-06-29 The Regents of the University of Michigan Materials for controlling the epitaxial growth of photoactive layers in photovoltaic devices
KR101320449B1 (en) * 2011-09-02 2013-10-23 주식회사 엘엠에스 Organic electronic device
WO2013032303A2 (en) * 2011-09-02 2013-03-07 주식회사 엘엠에스 Organic electronic device
KR102009804B1 (en) * 2011-12-26 2019-08-13 엘지디스플레이 주식회사 Organic light emitting diode display device and method for manufacturing the same
US9431621B2 (en) * 2012-03-13 2016-08-30 The Regents Of The University Of Michigan Metal oxide charge transport material doped with organic molecules
CN104508855B (en) * 2012-05-31 2017-06-23 乐金显示有限公司 Organic light emitting diode
KR101900287B1 (en) 2012-12-11 2018-09-19 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof
CN103296215A (en) * 2013-05-21 2013-09-11 京东方科技集团股份有限公司 Organic light emitting device and display device
GB2530748A (en) * 2014-09-30 2016-04-06 Cambridge Display Tech Ltd Organic Light Emitting Device
GB2533268A (en) * 2014-12-02 2016-06-22 Cambridge Display Tech Ltd Organic light-emitting device
KR20160089219A (en) 2015-01-19 2016-07-27 엘지디스플레이 주식회사 Oled light engine
JP6282614B2 (en) * 2015-06-22 2018-02-21 ユニバーサル ディスプレイ コーポレイション Solution processable doped triarylamine hole injection material
CN105244446B (en) 2015-08-28 2018-06-29 京东方科技集团股份有限公司 Organic electroluminescence device and preparation method thereof, display device
CN105140361B (en) * 2015-09-11 2019-08-27 Tcl集团股份有限公司 Light emitting diode with quantum dots and preparation method thereof
KR102010401B1 (en) 2015-10-27 2019-08-14 주식회사 엘지화학 Organic light emitting device
KR20170075118A (en) * 2015-12-22 2017-07-03 삼성디스플레이 주식회사 Organic light emitting device
KR20170075122A (en) 2015-12-22 2017-07-03 삼성디스플레이 주식회사 Organic light emitting device
KR102615638B1 (en) * 2015-12-22 2023-12-20 삼성디스플레이 주식회사 Organic light emitting device
KR20170075114A (en) * 2015-12-22 2017-07-03 삼성디스플레이 주식회사 Organic light emitting device
KR102579752B1 (en) 2015-12-22 2023-09-19 삼성디스플레이 주식회사 Organic light emitting device
EP3382770B1 (en) * 2017-03-30 2023-09-20 Novaled GmbH Ink composition for forming an organic layer of a semiconductor
KR102244800B1 (en) * 2017-12-11 2021-04-26 주식회사 엘지화학 Organic light emitting device and method of manufacturing the same
CN112909188B (en) 2019-12-03 2023-09-01 北京夏禾科技有限公司 Organic electroluminescent device
KR20210147122A (en) * 2020-05-26 2021-12-07 삼성디스플레이 주식회사 Amine compound and organic light emitting device including the same
CN115666146A (en) * 2021-07-10 2023-01-31 北京夏禾科技有限公司 Organic electroluminescent device

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5093698A (en) 1991-02-12 1992-03-03 Kabushiki Kaisha Toshiba Organic electroluminescent device
JP2000196140A (en) 1998-12-28 2000-07-14 Sharp Corp Organic electroluminescence element and fabrication thereof
WO2001067825A1 (en) 2000-03-09 2001-09-13 The Trustees Of Princeton University High efficiency transparent organic light emitting devices
US6524727B1 (en) * 1997-06-17 2003-02-25 South Bank University Limited Electroluminescent material
EP1351558A1 (en) * 2002-03-26 2003-10-08 Junji Kido Organic electroluminescent device
EP1524706A2 (en) * 2003-10-17 2005-04-20 Junji Kido Organic electroluminescent device
US20050100760A1 (en) * 2003-10-24 2005-05-12 Pentax Corporation White organic electroluminescent device
US20050274961A1 (en) 2004-06-11 2005-12-15 Chung-Yeh Iou Organic electroluminescent device and manufacuring method thereof

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6420031B1 (en) * 1997-11-03 2002-07-16 The Trustees Of Princeton University Highly transparent non-metallic cathodes
US6303238B1 (en) * 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
JP4543446B2 (en) * 1999-04-05 2010-09-15 Ｔｄｋ株式会社 Organic EL device
JP2000327664A (en) * 1999-05-17 2000-11-28 Toppan Printing Co Ltd Hole-transporting compound and organic thin film luminescent element produced by using the compound
US6573651B2 (en) * 2000-12-18 2003-06-03 The Trustees Of Princeton University Highly efficient OLEDs using doped ambipolar conductive molecular organic thin films
US6597012B2 (en) * 2001-05-02 2003-07-22 Junji Kido Organic electroluminescent device
US20100026176A1 (en) * 2002-03-28 2010-02-04 Jan Blochwitz-Nomith Transparent, Thermally Stable Light-Emitting Component Having Organic Layers
JP2004119074A (en) 2002-09-24 2004-04-15 Seiko Epson Corp Manufacturing method of electro-optical device, electro-optical device, and electronic equipment
US6982179B2 (en) * 2002-11-15 2006-01-03 University Display Corporation Structure and method of fabricating organic devices
JPWO2004064453A1 (en) * 2003-01-10 2006-05-18 株式会社半導体エネルギー研究所 Light emitting device and manufacturing method thereof
US20040219390A1 (en) * 2003-01-23 2004-11-04 Honeywell International, Inc. Benzoxazinone and quinazolinone derivatives
CN100448060C (en) * 2003-03-13 2008-12-31 富士胶片株式会社 Organic electroluminescent element and display device
DE10339772B4 (en) * 2003-08-27 2006-07-13 Novaled Gmbh Light emitting device and method for its production
KR100519968B1 (en) 2003-12-09 2005-10-13 삼성전자주식회사 Digital cable receiver capable of improving a reception performance for addition signal in Out-Of-Band and a mehtod receiving thereof
US7061011B2 (en) * 2003-11-26 2006-06-13 The Trustees Of Princeton University Bipolar organic devices
JP4393249B2 (en) * 2004-03-31 2010-01-06 株式会社 日立ディスプレイズ ORGANIC LIGHT EMITTING ELEMENT, IMAGE DISPLAY DEVICE, AND MANUFACTURING METHOD THEREOF
US7737632B2 (en) * 2004-04-27 2010-06-15 Fujifilm Corporation Organic EL element with lamination structure and its manufacturing method
WO2005109542A1 (en) * 2004-05-11 2005-11-17 Lg Chem. Ltd. Organic electronic device
JP4315874B2 (en) 2004-07-30 2009-08-19 三洋電機株式会社 Organic electroluminescent device and organic electroluminescent display device
KR101249172B1 (en) * 2004-07-30 2013-03-29 산요덴키가부시키가이샤 Organic electroluminescence device
US7804238B2 (en) * 2004-08-31 2010-09-28 Nissan Motor Co., Ltd. Functional thin-film element, producing method thereof, and article using functional thin-film element
JP4596977B2 (en) 2005-05-20 2010-12-15 株式会社 日立ディスプレイズ Organic light emitting display
US20070290195A1 (en) * 2005-08-22 2007-12-20 Stephen Forrest Increased open-circuit-voltage organic photosensitive devices
JP2007208102A (en) 2006-02-03 2007-08-16 Konica Minolta Holdings Inc Organic electroluminescent device, display unit, and lighting system
KR101223720B1 (en) * 2006-06-05 2013-01-17 삼성디스플레이 주식회사 Polymer compound and organic light-emitting device employing the same
GB2450382B (en) * 2007-06-22 2009-09-09 Cambridge Display Tech Ltd Organic thin film transistors, organic light-emissive devices and organic light-emissive displays

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5093698A (en) 1991-02-12 1992-03-03 Kabushiki Kaisha Toshiba Organic electroluminescent device
US6524727B1 (en) * 1997-06-17 2003-02-25 South Bank University Limited Electroluminescent material
JP2000196140A (en) 1998-12-28 2000-07-14 Sharp Corp Organic electroluminescence element and fabrication thereof
WO2001067825A1 (en) 2000-03-09 2001-09-13 The Trustees Of Princeton University High efficiency transparent organic light emitting devices
EP1351558A1 (en) * 2002-03-26 2003-10-08 Junji Kido Organic electroluminescent device
EP1524706A2 (en) * 2003-10-17 2005-04-20 Junji Kido Organic electroluminescent device
US20050100760A1 (en) * 2003-10-24 2005-05-12 Pentax Corporation White organic electroluminescent device
US20050274961A1 (en) 2004-06-11 2005-12-15 Chung-Yeh Iou Organic electroluminescent device and manufacuring method thereof

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
APPLIED PHYSICS LETTERS, vol. 72, 1998, pages 2147 - 2149
APPLIED PHYSICS LETTERS, vol. 73, 1998, pages 729 - 731
APPLIED PHYSICS LETTERS, vol. 86, 2005, pages 203507
GUFENG HE ET AL., PROC. INT. SOC. OPT. ENG., vol. 5464, 2004, pages 26 - 31
See also references of EP1994118A4
TANG ET AL.: "report an organic light emitting device having good characteristics", APPLIED PHYSICS LETTERS, vol. 51, 1987, pages 913

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8497500B2 (en) 2008-05-13 2013-07-30 Sharp Kabushiki Kaisha Organic EL device
JP2009277791A (en) * 2008-05-13 2009-11-26 Fuji Electric Holdings Co Ltd Organic el element
US8637854B2 (en) 2008-05-16 2014-01-28 Lg Chem, Ltd. Stacked organic light emitting diode
EP2299786A2 (en) * 2008-05-16 2011-03-23 LG Chem, Ltd. Stacked organic light-emitting diode
EP2299786A4 (en) * 2008-05-16 2011-08-03 Lg Chemical Ltd Stacked organic light-emitting diode
US9023492B2 (en) 2008-11-13 2015-05-05 Lg Chem, Ltd. Low voltage-driven organic electroluminescence device, and manufacturing method thereof
JP2012508975A (en) * 2008-11-13 2012-04-12 エルジー・ケム・リミテッド Low voltage driving organic light emitting device and method for manufacturing the same
JP2010123704A (en) * 2008-11-19 2010-06-03 Sony Corp Organic electroluminescent element, and display device
US20110210323A1 (en) * 2008-11-19 2011-09-01 Sony Corporation Organic electroluminescent element and display device
WO2010058737A1 (en) * 2008-11-19 2010-05-27 ソニー株式会社 Organic electroluminescent element and display device
EP2430677A4 (en) * 2009-05-13 2014-03-12 Global Oled Technology Llc Internal connector for organic electronic devices
EP2430677A1 (en) * 2009-05-13 2012-03-21 Global OLED Technology LLC Internal connector for organic electronic devices
JP2011187908A (en) * 2009-06-23 2011-09-22 Sumitomo Chemical Co Ltd Organic electroluminescent device
WO2010150792A1 (en) * 2009-06-23 2010-12-29 住友化学株式会社 Organic electroluminescent element
WO2011119162A1 (en) * 2010-03-25 2011-09-29 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US9368744B2 (en) 2010-04-01 2016-06-14 Samsung Display Co., Ltd. Organic light emitting diode device including multiple hole injection layers
EP2372805A3 (en) * 2010-04-01 2014-05-07 Samsung Display Co., Ltd. Organic light emitting diode device
US9660198B2 (en) 2011-07-15 2017-05-23 Kyulux, Inc. Organic electroluminescence element and compound used therein
WO2013011954A1 (en) 2011-07-15 2013-01-24 国立大学法人九州大学 Organic electroluminescence element and compound used therein
WO2013191428A1 (en) * 2012-06-18 2013-12-27 주식회사 엘지화학 Nitrogen-containing heterocyclic compound and organic electronic element comprising same
EP2865679A4 (en) * 2012-06-18 2016-01-27 Lg Chemical Ltd Nitrogen-containing heterocyclic compound and organic electronic element comprising same
EP2862862A4 (en) * 2012-06-18 2016-01-27 Lg Chemical Ltd Nitrogen-containing heterocyclic compound and organic electronic element comprising same
US9299935B2 (en) 2012-06-18 2016-03-29 Lg Chem, Ltd. Nitrogen-containing heterocyclic compounds and organic electronic device comprising the same
US9203033B2 (en) 2012-06-18 2015-12-01 Lg Chem, Ltd. Nitrogen-containing heterocyclic compounds and organic electronic device comprising the same
WO2013191429A1 (en) * 2012-06-18 2013-12-27 주식회사 엘지화학 Nitrogen-containing heterocyclic compound and organic electronic element comprising same
US9660202B2 (en) 2013-12-27 2017-05-23 Samsung Display Co., Ltd. Organic electroluminescence device
US10930854B2 (en) 2014-08-11 2021-02-23 Samsung Display Co., Ltd. Monoamine material for organic electroluminescent element, and organic electroluminescent element using same
US9966536B2 (en) 2014-09-09 2018-05-08 Samsung Display Co., Ltd. Organic electroluminescence device
US10090475B2 (en) 2014-10-06 2018-10-02 Samsung Display Co., Ltd. Organic electroluminescent device
KR20160055675A (en) 2014-11-07 2016-05-18 삼성디스플레이 주식회사 Organic electroluminescence device
US10184078B2 (en) 2014-11-07 2019-01-22 Samsung Display Co., Ltd. Organic electroluminescent device
KR20230100707A (en) 2014-11-07 2023-07-05 삼성디스플레이 주식회사 Organic electroluminescence device
US9902901B2 (en) 2014-11-07 2018-02-27 Samsung Display Co., Ltd. Organic electroluminescent device
KR20220070407A (en) 2014-11-07 2022-05-31 삼성디스플레이 주식회사 Organic electroluminescence device
US10689568B2 (en) 2014-11-07 2020-06-23 Samsung Display Co., Ltd. Organic electroluminescent device
US10385262B2 (en) 2014-11-07 2019-08-20 Samsung Display Co., Ltd. Organic electroluminescent device
US9997715B2 (en) 2014-11-18 2018-06-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
KR20210117227A (en) 2014-12-02 2021-09-28 삼성디스플레이 주식회사 Organic electroluminescence device
KR20180090232A (en) 2014-12-02 2018-08-10 삼성디스플레이 주식회사 Organic electroluminescence device
KR20160067021A (en) 2014-12-02 2016-06-13 삼성디스플레이 주식회사 Organic electroluminescence device
US9893293B2 (en) 2014-12-02 2018-02-13 Samsung Display Co., Ltd. Organic electroluminescent device
KR20230145985A (en) 2014-12-02 2023-10-18 삼성디스플레이 주식회사 Organic electroluminescence device
KR20160067728A (en) 2014-12-03 2016-06-14 삼성디스플레이 주식회사 Organic electroluminescence device
US11133470B2 (en) 2015-06-15 2021-09-28 Samsung Display Co., Ltd. Organic electroluminescent device
KR20160148437A (en) 2015-06-15 2016-12-26 삼성디스플레이 주식회사 Organic electroluminescence device
US10164197B2 (en) 2015-06-23 2018-12-25 Samsung Display Co., Ltd. Organic electroluminescent device
KR20170000741A (en) 2015-06-23 2017-01-03 삼성디스플레이 주식회사 Organic electroluminescence device
CN109415377A (en) * 2016-07-01 2019-03-01 株式会社Lg化学 Compound and organic electronic element comprising it
EP3459956A4 (en) * 2016-07-01 2019-06-19 LG Chem, Ltd. Compound and organic electronic element comprising same
US11974497B2 (en) 2016-07-01 2024-04-30 Lg Chem, Ltd. Compound and organic electronic element comprising same

Also Published As

Publication number Publication date
CN101400757B (en) 2013-05-15
JP2009530809A (en) 2009-08-27
KR20070093881A (en) 2007-09-19
JP2012186496A (en) 2012-09-27
EP1994118B1 (en) 2018-10-17
TWI376980B (en) 2012-11-11
KR100823443B1 (en) 2008-04-18
TW200735705A (en) 2007-09-16
US8586968B2 (en) 2013-11-19
CN101400757A (en) 2009-04-01
JP5064482B2 (en) 2012-10-31
US20100289008A1 (en) 2010-11-18
JP5576430B2 (en) 2014-08-20
EP1994118A1 (en) 2008-11-26
EP1994118A4 (en) 2011-01-26

Similar Documents

Publication Publication Date Title
EP1994118B1 (en) Organic light emitting diode having high efficiency and process for fabricating the same
EP2355625B1 (en) Low voltage-driven organic electroluminescence device, and manufacturing method thereof
JP5710704B2 (en) ORGANIC LIGHT EMITTING ELEMENT AND MANUFACTURING METHOD THEREOF
EP2139970B1 (en) Organic light emitting device and method of producing the same
KR100922759B1 (en) Organic light emitting device
JP5117388B2 (en) Organic electronic device
KR100922760B1 (en) Organic light emitting device
JP4915650B2 (en) Organic electroluminescence device
US20080284325A1 (en) Organic electroluminescent device and method for preparing the same
EP2378584A1 (en) Organic electroluminescent element
WO2009130858A1 (en) Organic electroluminescent device
KR20090072447A (en) Organic light emitting device
EP2752906B1 (en) Organic light emitting diode
EP2752908B1 (en) Organic light emitting diode
US20120007064A1 (en) Organic electroluminescent device and method for preparing the same
EP3435437A1 (en) Organic light-emitting element

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07715641

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2007715641

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 200780008829.4

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 12225096

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2009500291

Country of ref document: JP