WO2013089424A1 - Composé pour un dispositif opto-électrique organique, diode électroluminescente organique le comprenant et dispositif d'affichage comprenant la diode électroluminescente organique - Google Patents

Composé pour un dispositif opto-électrique organique, diode électroluminescente organique le comprenant et dispositif d'affichage comprenant la diode électroluminescente organique Download PDF

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WO2013089424A1
WO2013089424A1 PCT/KR2012/010783 KR2012010783W WO2013089424A1 WO 2013089424 A1 WO2013089424 A1 WO 2013089424A1 KR 2012010783 W KR2012010783 W KR 2012010783W WO 2013089424 A1 WO2013089424 A1 WO 2013089424A1
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신창주
강동민
강명순
이남헌
이현규
정호국
채미영
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제일모직 주식회사
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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
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    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
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    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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 for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent life, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the organic light emitting device.
  • An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
  • Organic optoelectronic devices can be divided into two types according to the operation principle.
  • excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
  • the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.
  • organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.
  • the host / dopant system can be used as a light emitting material.
  • materials constituting 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, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • This stable and efficient material should be preceded, and development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, development of new materials is continuously required.
  • the necessity of such a material development is the same in the other organic optoelectronic devices described above.
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has low initial investment cost. Large area has an advantage.
  • Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • LCD liquid crystal display
  • the response speed is 1000 times faster than the LCD in microseconds, it is possible to implement a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era.
  • the luminous efficiency In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer.
  • the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.
  • a compound for an organic optoelectronic device which can play a role of hole injection and transport or electron injection and transport, and can act as a light emitting host with an appropriate dopant.
  • An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.
  • a compound for an organic optoelectronic device represented by Formula 1 or 2 below is provided.
  • L is a single bond, a substituted or unsubstituted C10 to C30 arylene group or a substituted or unsubstituted C10 to C30 heteroarylene group
  • n is an integer of 0 to 3
  • Ar 1 is substituted or unsubstituted A C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group
  • X 1 is CR ′, N or SiR ′
  • R ′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • X 2 to X 5 are independently N or CR ', wherein R' is hydrogen, deuterium, A substituted or unsubstituted C1 to C10 alkyl group, a substituted
  • L is a single bond, a substituted or unsubstituted C10 to C30 arylene group or a substituted or unsubstituted C10 to C30 heteroarylene group
  • n is an integer of 0 to 3
  • Ar 1 is substituted or unsubstituted Is a C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group
  • X 1 is CR'R ', NR', SiR'R ', O, S, S (O) or S (O) 2
  • R 'and R' are hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • X 2 to X 5 are independently N or CR a , wherein R a is
  • n 1, and L may be a fused ring.
  • the sum of the carbon number of L and Ar 1 may be 20 or more.
  • Ar 1 may be a fused ring.
  • X 3 to X 5 are independently CR ', and R' is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or Unsubstituted C2 to C30 heteroaryl group or a combination thereof, X 2 may be N.
  • Ar 1 is a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted phenyl group.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device according to Chemical Formula 1.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device according to Chemical Formula 2.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-54.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-20.
  • the compound for an organic optoelectronic device may be any one of the following Chemical Formulas C-1 to C-76, D-1 to D-32, or E-1 to E-12.
  • the compound for an organic optoelectronic device may be a triplet excitation energy (T1) 2.0 eV or more.
  • the organic optoelectronic device may be selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode
  • at least one of the organic thin film layer is the above-described organic optoelectronic device It provides an organic light emitting device comprising a compound for.
  • the organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
  • the compound for an organic optoelectronic device may be included in an electron transport layer or an electron injection layer.
  • the compound for an organic optoelectronic device may be included in a light emitting layer.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.
  • a display device including the organic light emitting diode described above is provided.
  • Such a compound can be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer.
  • the organic optoelectronic device using the same has excellent electrochemical and thermal stability, and has excellent life characteristics, and may have high luminous efficiency even at a low driving voltage.
  • 1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • hole injection layer 230 light emitting layer + electron transport layer
  • substituted unless otherwise defined, at least one hydrogen of a substituent or a compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, trifluoro It means substituted by C1-C10 trifluoroalkyl group or cyano group, such as a romoxy group.
  • the C2 to C30 heteroaryl group may be a carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, or the like.
  • hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon.
  • an "alkyl group” means an aliphatic hydrocarbon group.
  • the alkyl group may be a "saturated alkyl group” that does not contain any double or triple bonds.
  • the alkyl group may be branched, straight chain or cyclic.
  • alkenylene group refers to a functional group consisting of at least two carbon atoms with at least one carbon-carbon double bond
  • alkynylene group means at least two carbon atoms with at least one carbon. -Refers to a functional group consisting of carbon triple bonds.
  • the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclo A butyl group, a cyclopentyl group, a cyclohexyl group, etc. are meant.
  • Aromatic group means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.
  • aryl group includes a monocyclic or fused ring polycyclic (ie, a ring that divides adjacent pairs of carbon atoms) functional groups.
  • Heteroaryl group means containing 1 to 3 hetero atoms selected from the group consisting of N, O, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • the carbazole derivative refers to a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is substituted with a hetero atom or carbon instead of nitrogen.
  • Specific examples thereof include dibenzofuran (dibenzofuranyl group), dibenzothiophene (dibenzothiophenyl group), fluorene (fluorenyl group) and the like.
  • the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate the injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.
  • an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer.
  • Compounds having specific electronic properties include substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyrimidinyl groups, substituted or unsubstituted triazinyl groups, and the like.
  • the compound for an organic optoelectronic device may have a core structure having an aryl group or heteroaryl group including a linking group having 10 or more carbon atoms in a carbazole derivative core having a fused ring.
  • the fused ring may include one nitrogen atom.
  • Common substituted or unsubstituted carbazoles are compounds having both hole and electronic properties. More specifically, hole properties may be slightly better than electronic properties. However, this may be controlled by a substituent attached to the carbazole.
  • the electronic and hole properties of the entire compound may be controlled.
  • the core structure may be used as a light emitting material, an electron injection material or an electron transporting material of an organic optoelectronic device. It may be particularly suitable for electron injection materials and / or electron transport materials.
  • the compound for an organic optoelectronic device may be a compound having various energy band gaps by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.
  • the hole transport ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in organic chemical and thermal stability It is possible to improve the life characteristics when driving the device.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device represented by the following formula (1) or (2).
  • L is a single bond, a substituted or unsubstituted C10 to C30 arylene group or a substituted or unsubstituted C10 to C30 heteroarylene group
  • n is an integer of 0 to 3
  • Ar 1 is substituted or unsubstituted A C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group
  • X 1 is CR ′, N or SiR ′
  • R ′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • X 2 to X 5 are independently N or CR ', wherein R' is hydrogen, deuterium, A substituted or unsubstituted C1 to C10 alkyl group, a substituted
  • n may be an integer of any one of 1 to 3.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device according to Chemical Formula 1.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device according to the formula (2).
  • L are a single bond, a substituted or unsubstituted phenyl group.
  • a biphenylene group, a terphenylene group, a naphthylene group, anthracenylene group, a phenanthryl group, a pyridine group, a fluorene group, a quinoline group, a pyrene group, a chrysene, etc. are not limited to this.
  • L may be a fused ring.
  • Ar 1 is a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted phenyl group.
  • the compound may have high charge mobility in the molecule.
  • Ar 1 may be a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar1 substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinoxaline group, substituted or unsubstituted quinoline group Etc.
  • Ar 1 may be selected from any one of the following Formulas S-1 to S-5, but is not limited thereto.
  • R 1 to R 4 are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group Or a combination thereof, in Formulas S-3 and S-4, any one of R 1 to R 4 represents a binding position, and in Formula S-5, any one of R 1 to R 3 represents a binding position. Indicates.
  • the sum of the carbon number of L and Ar 1 may be 20 or more.
  • Ar 1 may be a fused ring. More specific examples include substituted or unsubstituted benzimidazole groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted Fluoranthene group, substituted or unsubstituted pyrene group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinoxaline group, and the like.
  • Ar 1 may be a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group or quinoline group.
  • X 3 to X 5 are independently CR ', and R' is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or Unsubstituted C2 to C30 heteroaryl group or a combination thereof, X 2 may be N.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-54.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-20.
  • the compound for an organic optoelectronic device may be any one of the following Chemical Formulas C-1 to C-76, D-1 to D-32, or E-1 to E-12, but is not limited thereto.
  • introducing a functional group having the electronic characteristics is effective for improving the lifespan and driving voltage of the organic light emitting diode.
  • Compound for an organic optoelectronic device has a maximum emission wavelength of about 320 to 500 nm, triplet excitation energy (T1) is 2.0 eV or more, more specifically 2.0 to 4.0 eV range
  • T1 triplet excitation energy
  • the charge of the host having a high triplet excitation energy is well transferred to the dopant to increase the luminous efficiency of the dopant, and the driving voltage can be lowered by freely adjusting the HOMO and LUMO energy levels of the material. Because of the advantages it can be very useful as a host material or an electron transport material.
  • nonlinear optical material since the compound for an organic optoelectronic device has photoactive and electrical activity, nonlinear optical material, electrode material, color change material, optical switch, sensor, module, wave guide, organic transistor, laser, light absorber, dielectric and separator It can also be very usefully applied to materials such as (membrane).
  • the compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 90 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.
  • the compound for an organic optoelectronic device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport material.
  • Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
  • one embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.
  • the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like.
  • a compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, a gate, a source-drain electrode, or the like may be used as an electrode material. Can be used.
  • Another embodiment of the present invention is an organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least any one of the organic thin film layer is an embodiment of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to.
  • the organic thin film layer which may include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. At least one of the layers includes the compound for an organic optoelectronic device according to the present invention.
  • the hole transport layer or the hole injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the compound for an organic optoelectronic device when included in a light emitting layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.
  • FIG. 1 to 5 are cross-sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the organic light emitting diodes 100, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
  • the anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected into the organic thin film layer.
  • the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO 2 and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al.
  • Multilayer structure materials such as LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105.
  • the organic thin film layer 105 may exist only as a light emitting layer 130.
  • FIG. 2 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 and an hole transport layer 140 including an electron transport layer as the organic thin film layer 105, as shown in FIG. 2.
  • the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
  • the light emitting layer 130 functions as an electron transporting layer
  • the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.
  • FIG. 3 is a three-layered organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, and the organic thin film layer 105.
  • the light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.
  • FIG. 4 illustrates a four-layered organic light emitting diode 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105.
  • the hole injection layer 170 may improve adhesion to ITO used as an anode.
  • FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105.
  • the five-layer organic light emitting device 500 having five layers is present, and the organic light emitting device 500 is effective in lowering the voltage by separately forming the electron injection layer 160.
  • the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and the hole blocking layer (not shown) is included in the electron transport layer. It is desirable to provide an organic light emitting device having a simplified structure because it does not need to be formed separately.
  • the compound for an organic optoelectronic device when included in the light emitting layers 130 and 230, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
  • the above-described organic light emitting device includes a dry film method such as an evaporation, sputtering, plasma plating and ion plating after forming an anode on a substrate;
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
  • a display device including the organic light emitting diode is provided.
  • ITO was used as the cathode at a thickness of 1000 kPa
  • aluminum (Al) was used as the cathode at a thickness of 1000 kPa.
  • the anode is cut into a size of 50 mm ⁇ 50 mm ⁇ 0.7 mm ITO glass substrate having a sheet resistance value of 15 ⁇ / cm 2 to acetone, isopropyl alcohol and pure water Ultrasonic cleaning was performed for 5 minutes each, followed by UV ozone cleaning for 30 minutes.
  • Liq was vacuum deposited to a thickness of 0.5 nm as an electron injection layer on the electron transport layer, and Al was vacuum deposited to a thickness of 100 nm to form a Liq / Al electrode.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound prepared in Example 2 instead of using the compound prepared in Example 1 as an electron transport layer.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound prepared in Example 3, instead of using the compound prepared in Example 1 as the electron transport layer.
  • An organic light emitting device was manufactured in the same manner as in Example 4, except that the compound prepared in Example 1 and Liq were used as an electron transport layer in a 1 to 1 deposition.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that the compound prepared in Example 2 and Liq, which were used in an electron transport layer, were deposited to 1: 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that the compound prepared in Example 3 and Liq, which were used in an electron transport layer, were deposited on a one-to-one basis.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound represented by the following Formula R-1 instead of using the compound in Example 1 as the electron transport layer.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2) above.
  • the organic light emitting diodes of Examples 4, 7 and 9 of the present invention were found to be advantageous in terms of driving voltage, luminous efficiency and power efficiency compared to the organic light emitting diode according to Comparative Example 1.

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé pour un dispositif optoélectrique organique, une diode électroluminescente organique le comprenant et un dispositif d'affichage comprenant la diode électroluminescente organique, et fournit un composé pour un dispositif optoélectrique organique représenté par la formule chimique 1 ou 2 de façon à fabriquer une diode électroluminescente organique ayant de bonnes caractéristiques de durée de vie de service du fait qu'elle a une bonne stabilité électrochimique et thermique, et ayant un rendement d'émission de lumière élevé même à une faible tension de commande. La description des formules 1 et 2 se trouve dans la description détaillée.
PCT/KR2012/010783 2011-12-12 2012-12-12 Composé pour un dispositif opto-électrique organique, diode électroluminescente organique le comprenant et dispositif d'affichage comprenant la diode électroluminescente organique WO2013089424A1 (fr)

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WO2013165192A1 (fr) * 2012-05-02 2013-11-07 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
WO2013191177A1 (fr) * 2012-06-18 2013-12-27 東ソー株式会社 Composé azine cyclique, son procédé de fabrication, et élément électroluminescent organique le contenant
WO2014081206A1 (fr) * 2012-11-21 2014-05-30 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les contenant
WO2016089080A1 (fr) * 2014-12-02 2016-06-09 주식회사 두산 Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
JP2017088614A (ja) * 2015-01-20 2017-05-25 エスエフシー カンパニー リミテッド 新規なヘテロ環式化合物及びこれを含む有機発光素子
EP3269789A4 (fr) * 2015-03-09 2018-08-01 Hodogaya Chemical Co., Ltd. Matériau émetteur de lumière et élément électroluminescent organique
WO2018237385A1 (fr) * 2017-06-23 2018-12-27 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
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US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
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US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
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US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

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WO2013165192A1 (fr) * 2012-05-02 2013-11-07 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
WO2013191177A1 (fr) * 2012-06-18 2013-12-27 東ソー株式会社 Composé azine cyclique, son procédé de fabrication, et élément électroluminescent organique le contenant
WO2014081206A1 (fr) * 2012-11-21 2014-05-30 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les contenant
CN104781253A (zh) * 2012-11-21 2015-07-15 罗门哈斯电子材料韩国有限公司 新颖有机电致发光化合物和含有所述化合物的有机电致发光装置
US20190081244A1 (en) * 2014-10-17 2019-03-14 Lg Display Co., Ltd. Space-Through Charge Transfer Compound, and Organic Light Emitting Diode and Display Device Using the Same
US10892419B2 (en) * 2014-10-17 2021-01-12 Lg Display Co., Ltd. Space-through charge transfer compound, and organic light emitting diode and display device using the same
WO2016089080A1 (fr) * 2014-12-02 2016-06-09 주식회사 두산 Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
JP2017088614A (ja) * 2015-01-20 2017-05-25 エスエフシー カンパニー リミテッド 新規なヘテロ環式化合物及びこれを含む有機発光素子
EP3269789A4 (fr) * 2015-03-09 2018-08-01 Hodogaya Chemical Co., Ltd. Matériau émetteur de lumière et élément électroluminescent organique
US10559761B2 (en) 2015-03-09 2020-02-11 Kyulux, Inc. Light-emitting material, and organic electroluminescent device
US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
WO2018237385A1 (fr) * 2017-06-23 2018-12-27 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
US10547014B2 (en) 2017-06-23 2020-01-28 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11584739B2 (en) 2017-06-23 2023-02-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10644249B2 (en) 2017-12-22 2020-05-05 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11542260B2 (en) 2018-01-31 2023-01-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11608333B2 (en) 2018-03-20 2023-03-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11498914B2 (en) 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

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