WO2011155742A2 - Composé comprenant du carbazole et des dérivés d'amines aromatiques, élément électronique organique utilisant ce composé, et terminal comportant l'élément électronique organique - Google Patents

Composé comprenant du carbazole et des dérivés d'amines aromatiques, élément électronique organique utilisant ce composé, et terminal comportant l'élément électronique organique Download PDF

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WO2011155742A2
WO2011155742A2 PCT/KR2011/004126 KR2011004126W WO2011155742A2 WO 2011155742 A2 WO2011155742 A2 WO 2011155742A2 KR 2011004126 W KR2011004126 W KR 2011004126W WO 2011155742 A2 WO2011155742 A2 WO 2011155742A2
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organic
substituted
layer
compound
unsubstituted
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WO2011155742A3 (fr
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김동하
최대혁
박정환
유한성
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덕산하이메탈(주)
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
    • 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
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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]
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound comprising a carbazole and an aromatic amine derivative, an organic electric device using the same, and a terminal thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • Embodiments of the present invention to solve the problems of the above-described background, a compound containing a carbazole and an aromatic amine derivative having a novel structure has been found, and also when applying the compound to an organic electronic device organic electronic device It has been found that the effect of increasing the efficiency, lowering the driving voltage, increasing the lifetime and increasing the stability.
  • an object of the present invention is to provide a compound comprising a novel carbazole and an aromatic amine derivative, an organic electric device using the same, and a terminal thereof.
  • the present invention provides a compound of the formula:
  • the present invention is a compound containing a carbazole and an aromatic amine derivative can be used as a hole injection, hole transport, electron injection, electron transport, light emitting material and passivation (kepping) material in organic electronic devices, in particular light emitting material and host It can be used as a host or dopant in dopants, and can be used as a hole injection and hole transport layer.
  • the present invention also provides a compound including a carbazole and an aromatic amine derivative, an organic electronic device using the same, and a terminal including the organic electronic device.
  • the present invention is used as an organic light emitting device as a compound containing a carbazole and an aromatic amine derivative to provide the effect of increasing the efficiency of the organic electronic device, lowering the driving voltage, increase in life and stability when applied to the organic electroluminescent device.
  • 1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.
  • the present invention provides a compound of Formula 1 as follows.
  • Ar 1 to Ar 4 may each independently be a substituted or unsubstituted aromatic hydrocarbon group having 5 to 40 carbon atoms or a substituted or unsubstituted hetero atom having 3 to 60 nuclear atoms.
  • Ar 1 to Ar 4 may be bonded to adjacent groups, respectively, to form a substituted or unsubstituted saturated or unsaturated aliphatic ring, or a hetero ring having N, O, S, P, and Si as heteroatoms.
  • Ar 1 and Ar 2 , Ar 3 and Ar 4 may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated aliphatic ring or a hetero ring having N, O, S, P, and Si as heteroatoms. have.
  • Cz represents the following Chemical Formula 2, wherein R 1 is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, R 2 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, Substituted or unsubstituted C1-C50 alkyl group, substituted or unsubstituted C1-C50 alkoxy group, substituted or unsubstituted C6-C50 alkyl group, substituted or unsubstituted C1-C50 arylcycle Amino, substituted or unsubstituted alkoxycarbonyl groups having 2 to 50 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, halogen atoms, cyano groups, nitro groups, hydroxyl groups or carboxyl groups Can be. here Indicates the position of connection with other groups . It is the same below.
  • L independently represents a linking group selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted hetero arylene group, a tetravalent or higher substituted or unsubstituted aliphatic hydrocarbon, and specifically,
  • Specific examples of the compounds belonging to Formulas 1 and 2, which are compounds including carbazole and aromatic amine derivatives according to an embodiment of the present invention, may be the compounds of Formulas 3 and 4, but the present invention is not limited thereto. .
  • the present invention provides a compound of formula 3 when comprising 3 carbazole.
  • the present invention provides a compound of formula 4 when comprising 2 carbazole.
  • Ar 1 to Ar 4 may be the same as Ar 1 to Ar 4 in Formula 1, and R 1 to R 4 may be the same as R 1 and R 2 of Formula 2.
  • Compounds represented by Formula 1, Formula 3 to Formula 4 may be one of the compounds represented by Formula 5 and Formula 6, but is not limited thereto.
  • Ar 1 to Ar 4 , Cz, and R 1 to R 4, which are substituents of the compounds represented by Formula 1, Formula 3 to Formula 4, are difficult to exemplify all the compounds in a broad relationship.
  • the compounds represented by Formula 1, Formula 3, and Formula 4, which are not represented by Formulas 5 to 6, may also form part of the present specification.
  • organic electroluminescent devices in which compounds including carbazole and aromatic amine derivatives described with reference to Chemical Formulas 1 to 6 are used as the organic material layer.
  • organic electroluminescent devices include organic electroluminescent devices (OLEDs), organic solar cells, organophotoreceptor (OPC) drums, and organic Transistors (organic TFTs).
  • organic electroluminescent device As an example of an organic electroluminescent device to which compounds including carbazole and aromatic amine derivatives described with reference to Chemical Formulas 1 to 6 can be applied, an organic light emitting diode (OLED) is described, but the present invention is not limited thereto. Compounds comprising the carbazole and aromatic amine derivatives described above can be applied to the device.
  • OLED organic light emitting diode
  • Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 6 Provided is a light emitting device.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • At least one layer of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer is formed to include the compounds of Formulas 1 to 6 above. Except for the above, it may be manufactured in a structure known in the art using conventional manufacturing methods and materials in the art.
  • FIGS. 1 to 6 The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto.
  • reference numeral 101 is a substrate
  • 102 is an anode
  • 103 is a hole injection layer (HIL)
  • 104 is a hole transport layer (HTL)
  • 105 is a light emitting layer (EML)
  • 106 is an electron injection layer (EIL)
  • 107 represents an electron transport layer (ETL)
  • 108 represents a cathode.
  • the organic light emitting diode may further include a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for preventing the movement of electrons, and a protective layer.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound including the carbazole and the aromatic amine derivative described with reference to Chemical Formulas 1 to 6 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
  • the compound including the carbazole and the aromatic amine derivative described with reference to Chemical Formulas 1 to 6 is one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a protective layer It may be used instead of the above or may be used by forming a layer with them.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • the compound including the carbazole and the aromatic amine derivative described with reference to Chemical Formulas 1 to 6 may be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material, and a passivation (kepping) material, In particular, it can be used alone as a light emitting material and a host or dopant. More specifically, the compound may be used as the hole transport material in the hole transport layer can significantly improve the low driving voltage, high luminous efficiency and life.
  • the organic light emitting device is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • PVD physical vapor deposition
  • An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process of the compound including the carbazole and the aromatic amine derivative described above. have.
  • the substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
  • An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • Tg glass transition temperature
  • Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compound, a silicon-based arylamine compound, and the like.
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency.
  • an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene.
  • PPV polyphenylene vinylene
  • a polymer such as poly fluorene can be used for
  • the electron transport layer is positioned on the organic light emitting layer.
  • the electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is stacked on the electron transport layer.
  • the electron injection layer is an aromatic (aromatic) having an imidazole ring, a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, etc. It can be produced by using low molecular materials containing compounds, boron compounds, etc. In this case, the electron injection layer may be formed in a thickness range of 100 kPa to 300 kPa.
  • the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
  • the material used as the cathode it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
  • This terminal means a current or future wired or wireless communication terminal.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.
  • intermediate 2 is 2- (3,5-dibromophenyl) -9-phenyl-9H-carbazole, 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- except that 9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole is used instead of yl) -9H-carbazole. same. Yield 60%.
  • Ar of intermediate 3 is naphthyl, it is the same as the synthesis method except that N-phenylnaphthalen-1-amine is used instead of diphenylamine. Yield 70%.
  • Ar in intermediate 3 is biphenyl, 2- (3,5-dibromophenyl) -9-phenyl-9H-carbazole and N are substituted for 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole and diphenylamine. It is the same as the above synthesis method except that -phenylbiphenyl-4-amine is used. Yield 65%.
  • Ar of intermediate 4 is naphthyl, N- (3-bromo-5- (9-phenyl-9H) instead of 3-bromo-N, N-diphenyl-5- (9-phenyl-9H-carbazol-3-yl) aniline Same as the above synthesis method except that -carbazol-3-yl) phenyl) -N-phenylnaphthalen-1-amine is used. Yield 67%.
  • Ar of intermediate 4 is fluorene, N- (3-bromo-5- (9-phenyl-) instead of 3-bromo-N, N-diphenyl-5- (9-phenyl-9H-carbazol-3-yl) aniline It is the same as the synthesis method except that 9H-carbazol-2-yl) phenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-2-amine is used. Yield 55%.
  • the developed material was first vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.
  • NPD NPB
  • NPB NPD
  • a light emitting layer doped with 7% of BD-052X having a thickness of 45 nm on the hole transport layer (where BD-052X is a blue fluorescent dopant and a light emitting host material) 9,10-di (naphthalene-2-anthracene (AND)) was used as the hole blocking layer (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineole).
  • BAlq Ito
  • Alq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
  • Ar 1 to Ar 4 , Cz, and R 1 to R 4 which are substituents of the compounds represented by Chemical Formulas 1 and 3 to 4 , are representative examples of the synthesis of compounds in a wide range.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention has high efficiency and color purity as well as long-lasting blue light emission is obtained as a hole transporting material of the organic electroluminescent device Can be used to significantly improve the low driving voltage, high luminous efficiency and lifetime.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained. .

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Abstract

La présente invention se rapporte à un composé comprenant du carbazole et des dérivés d'amines aromatiques, à un élément électronique organique utilisant ce composé, ainsi qu'à un terminal comportant l'élément électronique organique.
PCT/KR2011/004126 2010-06-08 2011-06-07 Composé comprenant du carbazole et des dérivés d'amines aromatiques, élément électronique organique utilisant ce composé, et terminal comportant l'élément électronique organique WO2011155742A2 (fr)

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KR10-2010-0054059 2010-06-08
KR1020100054059A KR101188280B1 (ko) 2010-06-08 2010-06-08 카바졸과 방향족 아민 유도체를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말

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Cited By (6)

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KR20160029399A (ko) * 2014-09-05 2016-03-15 롬엔드하스전자재료코리아유한회사 정공 전달 재료 및 이를 포함하는 유기 전계 발광 소자
CN105418485A (zh) * 2015-12-22 2016-03-23 吉林奥来德光电材料股份有限公司 一种新的绿光主体化合物及其制备方法和应用
JP2016508964A (ja) * 2012-12-06 2016-03-24 ドク サン ネオルクス カンパニーリミテッド 有機電子素子用化合物、これを用いた有機電子素子及びその電子装置
WO2016064227A1 (fr) * 2014-10-23 2016-04-28 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
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