WO2014104545A1 - Composé pour dispositif optoélectronique organique, élément électroluminescent organique le comprenant et appareil d'affichage comprenant ledit élément électroluminescent organique - Google Patents

Composé pour dispositif optoélectronique organique, élément électroluminescent organique le comprenant et appareil d'affichage comprenant ledit élément électroluminescent organique Download PDF

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WO2014104545A1
WO2014104545A1 PCT/KR2013/008837 KR2013008837W WO2014104545A1 WO 2014104545 A1 WO2014104545 A1 WO 2014104545A1 KR 2013008837 W KR2013008837 W KR 2013008837W WO 2014104545 A1 WO2014104545 A1 WO 2014104545A1
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substituted
unsubstituted
group
organic
light emitting
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Korean (ko)
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허달호
조영경
류동완
홍진석
김준석
유동규
이남헌
이승재
장유나
정성현
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
    • 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
    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
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    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • 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

  • Display device including organic light emitting device
  • a display device comprising an organic light emitting device.
  • An organic optoelectric device refers to a device that requires 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.
  • an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes, respectively, to the current source (voltage source).
  • the current source voltage source
  • 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.
  • OLEDs organic light emitting diodes
  • organic light emission phenomenon refers to the use of organic materials to convert electrical energy into light energy.
  • 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 has a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.
  • a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer may be made of 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 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.
  • the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect.
  • the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect.
  • the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect.
  • Host / dopant systems can be used.
  • a material forming an 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 among the light emitting materials, 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 among the light emitting materials, etc.
  • This stable and efficient material must 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 device is a device in the form of a thin film by vacuum deposition method As it is manufactured, the efficiency and lifespan performance are good, and the polymer organic light emitting diode has an advantage of low initial investment cost and large area using an inkjet or spin coating method.
  • 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.
  • An organic light emitting device comprising the compound for an organic optoelectronic device and the
  • a display device including an organic light emitting device is provided.
  • 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 any one of the organic thin film layer of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to an embodiment.
  • an anode, a cathode and at least one organic thin film layer formed between the anode and the cathode the organic thin film layer is a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer Or a combination thereof, wherein the organic thin film layer includes a light emitting layer and a plurality of hole transport layers, and a hole transport layer adjacent to the light emitting layer among the plurality of hole transport layers is an organic optoelectronic device according to an embodiment of the present invention described above.
  • Comprising a compound any one of the hole transport layer that is not adjacent to the light emitting layer provides an organic light emitting device comprising a compound represented by the formula (B-1).
  • R 1 to R ⁇ Ar 1 to Ar 3 , L 1 to L 4, and nl to n4 are as defined in the following detailed description.
  • a display device including the organic light emitting device according to the embodiment of the present invention described above is provided.
  • the organic optoelectronic device including the compound for an organic optoelectronic device has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.
  • FIG. 1 and 2 are cross-sectional views showing various embodiments of the organic light emitting device that can be prepared using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or unsubstituted C1 to C10 such as 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, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc. It means substituted with a trifluorouroalkyl group or a cyano group.
  • substituted halogen group hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C1 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc.
  • Two adjacent substituents of the C10 trifluoroalkyl group or cyano group may be fused to form a ring.
  • hetero contains 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in one functional group, The rest means carbon.
  • alkyl group is aliphatic unless otherwise defined.
  • Alkyl groups may be "saturatedalkyl groups" that do not contain any double or triple bonds.
  • the alkyl group may be an alkyl group of 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 means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonuclear group And the like.
  • Aryl group means a substituent in which all elements of a cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic ( That is, a ring) group that shares adjacent pairs of carbon atoms.
  • Heteroaryl group '' means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P, and the rest are carbon.
  • the heteroaryl group is a fused ring In the case, each ring may contain 1 to 3 heteroatoms.
  • the hole characteristic means a property of having conductivity characteristics along the HQMO level to facilitate the injection and movement of the holes formed at the anode into the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
  • 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. More specifically, it may be similar to the property of attracting electrons.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and in the range of Ar 1 and Ar 2 Excluding heteroaryl groups, X 1 to X 16 are independently from each other, -N- or -CR'-, at least one of X 1 to X 16 is -N-, L 1 to L 3 are each other Independently, a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or Of these
  • Nl to ⁇ 3 are each independently an integer of 0 to 3, and R 'is hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substitution or
  • the compound represented by Chemical Formula 1 may have a core structure including at least one azacarbazolyl group.
  • a core structure including at least one azacarbazolyl group.
  • the compound for an organic optoelectronic device represented by Formula 1 may be a compound having a variety of energy band gap by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naph Tilyl, substituted or unsubstituted
  • Anthracenyl group substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted P-terphenyl group, substituted Or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted peryleneyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted Furanyl groups, substituted or unsubstituted thiophenyl groups, substituted or unsubstituted pyrrolyl groups, substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted imidazolyl groups,
  • Phenothiazineyl group substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted
  • Dibenzofuranyl group substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, or a combination thereof, but is not limited thereto.
  • Conjugation length can be determined, from which the triplet energy band 3 ⁇ 4 can be adjusted. Through this, it is possible to realize the characteristics of the material required in the organic optoelectronic device.
  • the triplet energy bandgap can be adjusted by changing the binding position of olso, para, and meta.
  • L 1 to L 3 include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or
  • Fluorenylene group substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted perrylenyl group, and the like.
  • L 1 to L 3 may be independently a phenylene group.
  • L 1 to L 3 is a phenylene group
  • both core parts may be bonded to ortho, meta or para based on the phenylene group.
  • L 1 to L 3 may be any one of the following substituents independently of each other. However, it is not limited thereto.
  • X is -0- or -S-.
  • Ar 1 and Ar 2 independently of one another, It may be any one of substituents. However, it is not limited thereto.
  • X is -0- or -S-, and ⁇ 5 to Ar 7 are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine Groups, nitro groups, carboxyl groups, ferrocenyl groups, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C1 To C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group , Substituted or unsub
  • Aryloxycarbonylamino group substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 aryl A thil group, a substituted or unsubstituted C1 to C20 heterocyclothiyl group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.
  • the compound of interest depends on the nature of the HOMO and / or LUMO Ar 1 and Ar 2 may be selectively adjusted.
  • Ar 1 and Ar 2 may be each independently a substituted or unsubstituted C6 to C30 aryl group.
  • the glass transition temperature of the molecular structure can be increased to increase the thermal stability of the compound.
  • At least one of X 1 to X 8 may be -N-, and at least one of X 9 to X 16 may be -N-. That is, according to one embodiment of the present invention
  • the compound for an organic optoelectronic device may have a core including two azacarbazolyl groups. In this case, it is possible to limit the hole transport capacity of the molecule to improve luminous efficiency, and to improve the roll-off characteristic.
  • the compound for an organic optoelectronic device may be any one of the following compounds, but is not limited thereto.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and includes nitrogen in the range of Ar 1 and Ar 2 Heteroaryl groups are excluded.
  • the compound represented by Chemical Chemistry 1 may be any one of the following compounds. This is merely an example.
  • an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, wherein at least any one of the organic thin film layer comprises the compound for the organic optoelectronic device An organic optoelectronic device is provided.
  • the compound for an organic optoelectronic device is used in an organic thin film layer
  • the organic thin film layer may be a hole injection layer or a hole transport layer.
  • the organic optoelectronic device is an organic light emitting device, an organic photoelectric device, an organic solar cell, It may be an organic transistor, an organic photosensitive drum or an organic memory device. More specifically, the organic optoelectronic device may be an organic light emitting device.
  • 1 and 2 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 and 200 may include an anode 120, a cathode 110, and at least one organic layer interposed between the anode and the cathode. It has a structure including the thin film layer 105.
  • the anode 120 comprises an anode material, which is typically
  • a material having a large work function is preferable to facilitate hole injection into the organic thin film layer.
  • the positive electrode material may include a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof, and include zinc oxide, indium oxide,
  • Metal oxides such as indium tin oxide ( ⁇ ) and indium zinc oxide (IZO); and combinations of metals and oxides such as ZnO and A1 or Sn0 2 and Sb; and poly (3-methylthiophene) , poly (3, 4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), but include polypyrrole and polyaniline, and the like. More specifically, a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • ITO indium tin oxide
  • the negative electrode 110 includes a negative electrode material, which is typically
  • the material has a small work function to facilitate electron injection into the organic thin film layer.
  • the negative electrode material include metals such as magnesium, kale, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or alloys thereof, and LiF / Al. , Multilayer structures such as Li0 2 / Al, LiF / Ca, UF / A1, and BaF 2 / Ca, and the like, but are not limited thereto. More specifically, 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, and the organic thin film layer 105 is
  • the light emitting layer 130 may be present only.
  • 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 include the light emitting layer 230 and the holes. It may be a two-layered type including the transport layer 140.
  • the light emitting layer 130 functions as an electron transporting layer
  • the hole transporting layer 140 has a bonding property with a transparent electrode such as?
  • the organic thin film layer 105 of FIG. 1 and FIG. 2 may further include an electron injection layer, an auxiliary electron transport layer, an electron transport layer, an auxiliary major transport layer, a hole injection layer, and a combination thereof.
  • the electron transport layer 150, the light emitting layers 130 and 230, the hole transport layer 140 constituting the organic thin film layer 105, an electron injection layer, an auxiliary electron transport layer, which may be further included, are not shown. Any one selected from the group consisting of an electron transport layer, an auxiliary major transport layer, a hole injection layer, and a combination thereof includes the organic optoelectronic device material.
  • 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 optoelectronic device is provided.
  • an anode, a cathode and at least one organic thin film layer formed between the anode and the cathode the organic thin film layer is a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer Or a combination thereof, and the organic thin film layer includes a light emitting layer and a plurality of hole transport layers, and a hole transport layer adjacent to the light emitting layer among the plurality of hole transport layers is an organic optoelectronic device according to an embodiment of the present invention described above.
  • Comprising a compound, any one of the hole transport layer that is not adjacent to the light emitting layer provides an organic light emitting device comprising a compound represented by the formula (B-1). [Formula Bl]
  • R 'to R 4 are each independently 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, R 1 and R 2 may form a fused ring with each other, R 3 and R 4 may form a fused ring with each other, and Ar 1 to Ar 3 may be independently substituted or unsubstituted.
  • a C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, L 1 to L 4 are each independently a substituted or unsubstituted 1 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkoxy A nylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and ⁇ to ⁇ 4 are integers independently of each other.
  • the organic optoelectronic device may include a plurality of hole transport layers. In this case, electrons rather than a single hole transport layer
  • the organic optoelectronic device according to the exemplary embodiment of the present invention has excellent electrochemical and thermal stability, thereby improving lifespan characteristics and high luminous efficiency even at a low driving voltage.
  • the hole transport layer adjacent to the light emitting layer of the plurality of hole transport layer may include a compound according to an embodiment of the present invention described above. Since the description is duplicated, it will be omitted.
  • any one of the hole transport layer not adjacent to the light emitting layer may include a compound represented by Formula B-1.
  • the compound represented by Bl may be an amine-based compound in which at least one substituent of an amine is substituted with a carbazole group.
  • R 1 and R 2 may form a fused ring with each other
  • R 3 and R 4 may form a fused ring with each other. In this case, thermal stability is increased, and electron transfer and injection characteristics are increased.
  • an hole transport layer Electron hopping is optimized for the energy level of, resulting in excellent electrochemical and thermal stability. Accordingly, the organic optoelectronic device may have improved lifetime characteristics and may have high luminous efficiency even at a low driving voltage.
  • the compound represented by Chemical Formula B-1 may be represented by any one of the following Chemical Formulas J-1 to J-144. However, it is not limited thereto.
  • HOMO level of the compound represented by Formula 1 may be more than 5.4 eV and less than 6.0 eV. In this case, holes can be smoothly injected from the chemical formula B-1 and the injection barrier can be lowered to the light emitting layer.
  • Triplet excitation energy (T1) of the compound represented by Formula 1 is 2.5 eV or more
  • the HOMO level of the compound represented by Formula B-1 may be 5.2 eV or more and 5.6 eV or less.
  • the driving voltage can be lowered by lowering the hole injection barrier from the anode.
  • a display device including the organic light emitting device according to the embodiment of the present invention described above is provided.
  • the following reaction scheme shows a reaction scheme by introducing an aryl group (or a heteroaryl group) into the azacarbazole structure.
  • Azacarbazole halideol was synthesized through the following reaction. This can be used as an intermediate for the compound for an organic optoelectronic device according to an embodiment of the present invention later
  • chloride is not well synthesized by a typical Suzuki coupling reaction. It is reported that the ring reaction yield is different. (See K. L. Billingsley, K. W.
  • the organic light emitting device has a structure having five organic thin layers, specifically
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using Example 2 compound instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 4 instead of Example 1.
  • Example 25 An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 5 instead of Example 1.
  • Example 25
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 6 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 10 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 11 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound of Example 12 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using the compound using Example 17 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using Example 18 compound instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using Example 19 compound instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 21 except for using Example 20 compound instead of Example 1.
  • Example 21 In Example 21 above, ⁇ , ⁇ '-di (1-naphthyl) - ⁇ , ⁇ '-diphenylbenzidine [ ⁇ ] is used in place of HT-1, and Example 1 N, ⁇ '-di ( An organic light emitting diode was manufactured according to the same method except that 1-naphthyl) - ⁇ , ⁇ '-diphenylbenzidine [ ⁇ ] was used.
  • Example 1 Using [ ⁇ ] and Example 1 Organic Light Emitting except that Tris (4,4 ', 4 "-(9-carbazolyl))-triphenylamine [TCTA] was used instead of the compound. The device was manufactured.
  • Example 21 HT-1 instead of the compound of Example 1
  • the current value flowing through the unit device was measured by using a current-voltmeter (Keithley2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured by using a luminance meter (Minolta Cs-1000 A) while increasing the voltage from 0V to 10V to obtain a result.
  • a luminance meter Minolta Cs-1000 A
  • Luminous efficiency (cd / A) and power efficiency (lm / W) of the same brightness (l, 000 cd / m2) were calculated using the brightness, current density, and voltage measured from (1) and (2).
  • Examples 21 to 32 using the compound according to one embodiment of the present invention as an auxiliary hole transport layer compared to Comparative Example 1 or Comparative Example 3 without using the auxiliary hole transport layer were found to improve the luminous efficiency and lifetime of the organic light emitting device.
  • the embodiment of the present invention can be seen that the luminous efficiency is significantly increased by at least 10% or more, the embodiment of the present invention compared to Comparative Example 2 using the conventionally known TCTA as an auxiliary hole transport layer, the life of the light emitting device Is increased by at least 10%, considering that the lifetime of the device in terms of commercialization of the actual device is one of the biggest problems of commercialization. The results of the embodiments are considered to be sufficient to commercialize the device.
  • Example 33 Manufacture of a Red Organic Light-Emitting Element
  • [DNTPD] was vacuum deposited to form a hole injection layer of 600 A thickness.
  • HT-1 was then vacuum deposited to form a 200 A thick hole transport layer.
  • An auxiliary hole transport layer having a thickness of 100A was formed by vacuum deposition using the compound prepared in Example 1 on the hole transport layer.
  • (4,4'- ⁇ , ⁇ '-dicarbazole) biphenyl [CBP] is used as a host on top of the auxiliary hole transport layer and dopant bis (2-phenylquinoline) (acetylacetonate) iridium (III) [Ir (pq) 2 acac] 7 parts by weight doped with 0/0 to form a light-emitting layer thickness of 300 a by vacuum deposition.
  • the organic light emitting device has a structure having six organic thin film layers, specifically
  • An organic light emitting diode was manufactured according to the same method as Example 33 except for using Example 2 compound instead of Example 1.
  • Example 33 using the compound of Example 4 instead of Example 1 Except for the organic light emitting device was manufactured in the same manner.
  • An organic light emitting diode was manufactured according to the same method as Example 33 except for using the compound of Example 5 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 33 except for using the compound of Example 6 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 33 except for using Example 10 compound instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 33 except for using Example 12 compound instead of Example 1.
  • Example 33 using Example 20 compound instead of Example 1 An organic light emitting device was manufactured by the method.
  • Example 33 ⁇ , ⁇ '-di (1-naphthyl) - ⁇ , ⁇ '-diphenylbenzidine instead of HT-1
  • An organic light-emitting device was manufactured in the same manner except that [ ⁇ ] was used and ⁇ , ⁇ '-di (1-naphthyl) - ⁇ , ⁇ '-diphenylbenzidine [ ⁇ ] was used instead of the compound. Prepared.
  • Example 33 ⁇ , ⁇ '-di (1-naphthyl) - ⁇ , ⁇ '-diphenylbenzidine instead of HT-1
  • Example 1 An organic light-emitting device was used in the same manner except for using [ ⁇ ] and using Tris (4,4 ', 4 "-(9-carbazolyl))-triphenylamine [TCTA] instead of the compound. was prepared.
  • Example 33 using HT-1 instead of Example 1 compound
  • the measuring method is as above-mentioned. However, in the case of the life characteristics, the time taken for the luminance to decrease by 80% was measured while the current density corresponding to 1000 nit flowed through the device.
  • Examples 33 to 40 using the compound according to one embodiment of the present invention as an auxiliary hole transport layer compared to Comparative Example 4 or Comparative Example 6 without using the auxiliary hole transport layer is found to improve the luminous efficiency and lifetime of the organic light emitting device.
  • the embodiment of the present invention compared to Comparative Example 3 can be seen that the luminous efficiency is greatly increased by at least 15% or more, and the embodiment of the present invention compared to Comparative Example 5 using the conventionally known TCTA as an auxiliary hole transport layer It can be seen that the increase of at least 10% and the life of the light emitting device is at least about 20%.

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Abstract

La présente invention concerne un composé pour un dispositif optoélectronique organique, un élément électroluminescent le comprenant et un appareil d'affichage comprenant ladite diode électroluminescente organique. L'invention concerne le composé pour un dispositif optoélectronique organique qui est exprimé par la formule chimique 1.
PCT/KR2013/008837 2012-12-31 2013-10-02 Composé pour dispositif optoélectronique organique, élément électroluminescent organique le comprenant et appareil d'affichage comprenant ledit élément électroluminescent organique WO2014104545A1 (fr)

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KR102254724B1 (ko) * 2014-08-08 2021-05-21 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102617840B1 (ko) * 2015-11-26 2023-12-26 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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