US20120043531A1 - Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the light emitting diode - Google Patents

Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the light emitting diode Download PDF

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US20120043531A1
US20120043531A1 US13/212,484 US201113212484A US2012043531A1 US 20120043531 A1 US20120043531 A1 US 20120043531A1 US 201113212484 A US201113212484 A US 201113212484A US 2012043531 A1 US2012043531 A1 US 2012043531A1
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Sung-Hyun Jung
Dal-Ho Huh
Dong-wan Ryu
Kyoung-Mi LEE
Eui-Su Kang
Mi-Young Chae
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Cheil Industries Inc
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Cheil Industries Inc
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Assigned to CHEIL INDUSTRIES, INC. reassignment CHEIL INDUSTRIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHAE, MI-YOUNG, HUH, DAL-HO, JUNG, SUNG-HYUN, KANG, EUI-SU, LEE, KYOUNG-MI, RYU, DONG-WAN
Publication of US20120043531A1 publication Critical patent/US20120043531A1/en
Priority to US14/072,871 priority Critical patent/US9478753B2/en
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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
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    • 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
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    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/14—Carrier transporting layers
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • Y02E10/549—Organic PV cells

Definitions

  • Embodiments relate to a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display device including the light emitting diode.
  • An organic optoelectronic device is, in a broad sense, a device for transforming photo-energy to electrical energy or a device for transforming electrical energy to photo-energy conversely.
  • An organic optoelectronic device may be classified as follows in accordance with its driving principles.
  • One type of organic optoelectronic device is an electronic device driven as follows: excitons are generated in an organic material layer by photons introduced from an external light source to a device; the excitons are separated into electrons and holes; and the electrons and holes are respectively transferred to different electrodes and used as a current source (a voltage source).
  • Another type of organic optoelectronic device is an electronic device driven as follows: a voltage or a current is applied to at least two electrodes to inject holes and/or electrons into an organic material semiconductor positioned at an interface of the electrodes, and the device is driven by the injected electrons and holes.
  • the organic optoelectronic device may include an organic light emitting diode (OLED), an organic solar cell, an organic photo-conductor drum, an organic transistor, an organic memory device, and the like. and may include a hole injecting or transporting material, an electron injecting or transporting material, or a light emitting material.
  • organic light emitting diode has recently drawn attention due to an increase in demand for a flat panel display.
  • organic light emission refers to transformation of electrical energy to photo-energy.
  • Embodiments are directed to a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display device including the light emitting diode.
  • the embodiments may be realized by providing a compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 1:
  • Ar is a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group
  • X is N, B, or P
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group
  • n and m are each independently integers of 0 to about 3
  • R 1 to R 9 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 2:
  • Ar is a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group
  • X is N, B, or P
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group
  • n and m are each independently integers of 0 to about 3
  • R 1 to R 9 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group,
  • X may be N.
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 3:
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n and m each independently integers of 0 to about 3, and R 1 to R 9 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n and m are each independently integers of 0 to about 3, and R 1 to R 9 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 ary
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 5:
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n and m are each independently integers of 0 to about 3, and R 1 to R 9 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 ary
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 6:
  • L 1 is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n is an integer of 0 to about 3, and R 1 to R 5 and R 8 to R 11 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula A-1, A-10, A-19, A-28, A-37, A-46, A-55, A-56, A-61, A-66, A-67, A-76, A-77, A-86, or A-87:
  • the compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulae B-1 to B-6:
  • the compound represented by Chemical Formula 1 is represented by the following Chemical Formula A-2, A-4, A-6, A-8, A-11, A-13, A-15, A-17, A-20, A-22, A-24, A-26, A-29, A-31, A-33, A-35, A-38, A-40, A-42, A-44, A-47, A-49, A-51, A-53, A-57, A-59, A-62, A-64, A-69, A-71, A-72, A-74, A-79, A-81, A-82, A-84, A-89, A-91, A-92, or A-94.
  • the compound represented by Chemical Formula 1 is represented by the following Chemical Formula A-3, A-5, A-7, A-9, A-12, A-14, A-16, A-18, A-21, A-23, A-25, A-27, A-30, A-32, A-34, A-36, A-39, A-41, A-43, A-45, A-48, A-50, A-52, A-54, A-58, A-60, A-63, A-65, A-68, A-70, A-73, A-75, A-78, A-80, A-83, A-85, A-88, A-90, A-93, or A-95.
  • the compound may be a hole transport material or hole injection material of an organic light emitting diode.
  • the compound may have a triplet excitation energy (T1) of about 2.0 eV or greater.
  • the organic optoelectronic device may include one selected from an organic photoelectronic device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the embodiments may also be realized by providing an organic light emitting diode including an anode, a cathode, and at least one organic thin layer between the anode and cathode, wherein the at least one organic thin layer includes the compound for an organic optoelectronic device according to an embodiment.
  • the at least one organic thin layer may be selected from an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer, and a combination thereof.
  • HTL hole transport layer
  • HIL hole injection layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the at least one organic thin layer may include a hole transport layer (HTL) or a hole injection layer (HIL), and the compound for an organic optoelectronic device may be included in the hole transport layer (HTL) or the hole injection layer (HIL).
  • HTL hole transport layer
  • HIL hole injection layer
  • the at least one organic thin layer may include an emission layer, and the compound for an organic optoelectronic device may be included in the emission layer.
  • the at least one organic thin layer may include an emission layer, and the compound for an organic optoelectronic device may be a phosphorescent host material or fluorescent host material in the emission layer.
  • the embodiments may also be realized by providing a display device including the organic light emitting diode according to an embodiment.
  • FIGS. 1 to 5 illustrate cross-sectional views of organic light emitting diodes including compounds according to various embodiments.
  • substituted may refer to one substituted with deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group such as a trifluoromethyl group, or a cyano group, instead of at least hydrogen of substituents or compounds.
  • the term “combination thereof” may refer to at least two substituents bound to each other by a linker, or at least two substituents condensed to each other.
  • alkyl group may refer to an aliphatic hydrocarbon group.
  • the alkyl group may be a saturated alkyl group that does not include any alkene group or alkyne group.
  • the alkyl may be an unsaturated alkyl group that includes at least one alkene group or alkyne group.
  • alkene may refer to a group in which at least two carbon atoms are bound in at least one carbon-carbon double bond
  • alkyne may refer to a group in which at least two carbon atoms are bound in at least one carbon-carbon triple bond.
  • the alkyl may be branched, linear, or cyclic.
  • the alkyl group may have 1 to 20 carbon atoms. In an implementation, the alkyl group may be a medium-sized alkyl having 1 to 10 carbon atoms. In another implementation, the alkyl group may be a lower alkyl having 1 to 6 carbon atoms.
  • a C1-C4 alkyl may have 1 to 4 carbon atoms and may be selected from the group of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and t-butyl.
  • Examples of an alkyl group may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an ethenyl group, a propenyl group, a butenyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and/or a cyclohexyl group, which may be individually and independently substituted.
  • aromatic group may refer to a cyclic functional group where all elements have conjugated pi-orbitals.
  • aromatic group include an aryl group and a heteroaryl group.
  • aryl group may refer to an aryl group including a carbocyclic aryl (e.g., phenyl) having at least one ring having a covalent pi electron system.
  • heteroaryl group may refer to an aryl group where 1 to 3 heteroatoms selected from N, O, S, and P, and remaining carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • spiro structure may refer to a cyclic structure having a common carbon contact point.
  • spiro structure may refer to a compound or substituent having a spiro structure.
  • a compound for an organic optoelectronic device may have a core structure including a carbazolyl and a fluorenyl group as a substituent linked to an N, B, or P atom.
  • the carbazolyl group (with excellent hole properties, e.g., hole transport properties and/or hole injection properties) may be linked to the N, B, or P atom in the core structure.
  • the compound may be used as a hole injection material or a hole transport material for an organic light emitting diode.
  • At least one substituent combined or bound to the core may have excellent electron properties, e.g., electron transport properties and/or electron injection properties. Accordingly, the compound may have the core structure having excellent hole properties and may be reinforced with electron properties of the substituent and thus, may satisfy a condition desirable for an emission layer.
  • the compound may be used as a host material for an emission layer.
  • the hole properties are that holes generated at an anode may be easily injected into an emission layer and moved therein due to conductive properties according to HOMO levels.
  • the electron properties are that electrons generated at a cathode may be easily injected into an emission layer and moved therein due to conductive properties according to LUMO levels.
  • the compound for an organic optoelectronic device may have the core as described above and may include various substituents substituted on the core and thus, may have various energy band gaps.
  • a compound having various energy levels (according to a substituent thereof) is used for an organic photoelectric device, it may reinforce hole transport capability or electron transport capability and thus, may have excellent effects on efficiency and driving voltage and also, may have excellent electrochemical and thermal stability. Accordingly, life-span of the organic photoelectric device may be improved.
  • the compound for an organic optoelectronic device may be represented by the following Chemical Formula 1.
  • Ar may be a substituted or unsubstituted triperylenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dibenzothiophenyl group,
  • X may be N, B, or P
  • L 1 and L 2 may each independently be a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • n and m may each independently be integers of 0 to about 3, and
  • R 1 to R 9 may each independently be hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group
  • the compound for an organic optoelectronic device may exhibit excellent hole or electron properties, film stability, thermal stability, and high triplet excitation energy (T1).
  • the compound may have excellent thermal stability and/or excellent resistance against oxidation.
  • the compound represented by the above Chemical Formula 1 may have an asymmetrical bipolar structure.
  • the asymmetrical bipolar structure may improve hole and electron transport capabilities and thus, may improve luminous efficiency and performance of a device.
  • substituents may be selected to prepare a compound with a bulky structure and thus, lower crystallinity.
  • the compound with lower crystallinity may improve life-span of a device.
  • Ar may not be a carbazolyl group.
  • X a core atom in the above Chemical Formula 1, may not be substituted with more than one carbazolyl group.
  • Such a structure may avoid increased symmetry and thus, avoid increased crystallinity.
  • L 1 , L 2 , n, and m may be adjusted to control a length of the compound, which may adjust ⁇ -conjugation length of the compound. Accordingly, the compound may be adjusted regarding a triplet energy bandgap and thus, may be usefully applied to an emission layer for an organic photoelectric device as a phosphorescent host
  • the compound when a heteroaryl group is introduced as the substituent, the compound may have a molecule structure with bipolar properties and may realize high efficiency as a phosphorescent host.
  • the fluorenyl group as a substituent for the core, may decrease symmetry of the molecule and thus, may hinder crystallization of the compound. Accordingly, when this compound is used for a hole injection layer and/or a hole transport layer (HTL) for an organic electric field light emitting element, it may help achieve long life-span and high efficiency of the element.
  • HTL hole transport layer
  • Ar may be a substituted or unsubstituted triperylenyl or triphenylenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.
  • the triphenylenyl group may have a bulky structure and may bring about resonance effects. Thus, the triphenylenyl group may suppress a side reaction occurring in the solid status of a compound and the compound may improve performance of an organic light emitting diode.
  • triphenylenyl group may make the compound bulky and may lower crystallinity thereof, thereby increasing life-span of a device prepared using the compound.
  • the triphenylenyl group may have a broad bandgap and a large triplet excitation energy (unlike other substituents). Thus, the triphenylenyl group may be combined with the compound including carbazole without decreasing bandgap or triplet excitation energy of the compound.
  • Ar is the dibenzofuranyl group or dibenzothiophenyl group having hole transport property and is asymmetrically combined as shown in the above Chemical Formula 1, the group may include a hetero aromatic cycle withdrawing electrons; and may bring about asymmetric bipolar properties all over a molecule.
  • substituted in the definition of “substituted or unsubstituted” may refer to one substituted with a substituent selected from deuterium, a halogen, a cyano group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C40 silyl group, and a combination thereof, instead of hydrogen of each substituent.
  • a substituent selected from deuterium, a halogen, a cyano group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstit
  • a “substituted” structure as aforementioned may subtly regulate electric-optical properties and thin film properties to optimize performance of a material for an organic photoelectric device as well as maintain basic properties of a compound.
  • the compound for an organic photoelectric device may be represented by the following Chemical Formula 2.
  • Chemical Formula 2 may be the same as the aforementioned Chemical Formula 1, except for being limited to a particular combination location with respect to the carbazolyl group and the fluorenyl group.
  • Chemical Formula 2 it may be advantageous in terms of actual synthesis.
  • Chemical Formula 2 is the same as Chemical Formula 1 (i.e., definitions of X, Ar, etc.), and repeated descriptions thereof are omitted.
  • the compound for an organic photoelectric device may be represented by the following Chemical Formula 3.
  • the compound represented by Chemical Formula 3 may exhibit improved thermal stability and may remarkably increase half life-span of a device.
  • the compound for an organic photoelectric device may be represented by the following Chemical Formula 4.
  • the structure of the above Chemical Formula 4 defines Ar (from Chemical Formula 1) as a dibenzothiophenyl group. This structure may improve thermal stability of a material and remarkably increases half life-span of a device.
  • the compound for an organic photoelectric device may be represented by the following Chemical Formula 5.
  • the structure of the above Chemical Formula 5 defines Ar (from Chemical Formula 1) as a triphenylenyl group.
  • This structure may broaden T1 energy of triphenylene as well as improve thermal stability of a material and thus, may be used for hole transport and injection layers of a phosphorescent light emitting material.
  • the compound for an organic photoelectric device may be represented by the following Chemical Formula 6.
  • X may be N, B, or P
  • L 1 may be a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • n may be an integer of 0 to about 3
  • R 1 to R 5 and R 8 to R 11 may each independently be hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 al
  • L 1 may be phenylene, and n may be 1.
  • an organic photoelectric device e.g., an organic light emitting diode
  • the device may have excellent life-span.
  • the compound for an organic optoelectronic device may exhibit remarkably improved thermal stability when phenyl groups are substituted at the 9 and 9′ positions of the fluorenyl group and a biphenyl group is substituted on X.
  • the compound may not be easily decomposed due to heat, even when deposited at a higher speed during the fabrication of a device.
  • X may be N.
  • a tertiary amine core may be formed, and hole properties of the entire compound may be further improved.
  • the compound for an organic photoelectric device may be represented by one of the following Chemical Formulae A-1 to A-95.
  • Compounds having following structures may exhibit excellent thin film properties and improved thermal stability (due to asymmetry thereof) and may exhibit excellent hole transport properties of a carbazolyl group.
  • the compound may be applied to a hole injection layer and a hole transport layer (HTL) for an organic electric field light emitting element, thereby achieving long life-span and high efficiency of the organic electric field light emitting element.
  • HTL hole transport layer
  • the compound for an organic optoelectronic device may be represented by one of the following Chemical Formulae B-1 to B-6.
  • the compound having a structure of one of Chemical Formulae A-1 to A-95 and B-1 to B-6 is used to fabricate an organic photoelectric device (e.g., organic light emitting diode), the device may have excellent life-span.
  • an organic photoelectric device e.g., organic light emitting diode
  • a functional group with electron properties in a molecule may deteriorate electron blocking properties of the electron blocking layer. Accordingly, the compound should not include a functional group with electron properties. Examples of a functional group with electron properties may include benzoimidazole, pyridine, pyrazine, pyrimidine, triazine, quinoline, isoquinoline, and the like.
  • a compound for an organic optoelectronic device is used for an electron blocking layer or a hole transport layer (HTL) (or a hole injection layer (HIL)
  • the foresaid description may be limited.
  • the functional group with electron properties may be included in the compound to effectively improve life-span of an organic light emitting diode and decrease its driving voltage.
  • the compound for an organic optoelectronic device may have a maximum light emitting wavelength of about 320 to 500 nm and a triplet excitation energy (T1) of more than about 2.0 eV, e.g., about 2.0 to about 4.0 eV. Accordingly, the compound with high triplet excitation energy (T1) as a host may effectively transport a charge to a dopant and thus, may increase luminous efficiency of the dopant and also may be freely adjusted according to HOMO and LUMO energy levels and decrease driving voltage of a device. Thus, the compound may be usefully used as a host material or a charge transport material.
  • the compound for an organic optoelectronic device may have photoactive and electric activity and thus, may be usefully applied to a non-linear optical material, an electrode material, a discoloring material, an optical switch, a sensor, a module, a wave guide, an organic transistor, a laser, a light-absorbing agent, a dielectric material, a material for a separating membrane, or the like.
  • the compound for an organic optoelectronic device may have a glass transition temperature of about 90° C. or higher and a thermal decomposition temperature of about 400° C. or higher and thus, may exhibit excellent thermal stability. Accordingly, the compound may provide high efficiency to an organic photoelectric device.
  • the compound for an organic optoelectronic device may play a role in emitting light or injecting and/or transporting electrons, and may act as a light emitting host together with a suitable dopant.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material, a blue light emitting dopant material, or an electron transporting material.
  • the compound for an organic optoelectronic device according to an embodiment may be used for an organic thin layer.
  • the life span characteristic, efficiency characteristic, electrochemical stability, and thermal stability of an organic photoelectric device may be improved; and the driving voltage thereof may be decreased.
  • an organic optoelectronic device that includes the compound for an organic optoelectronic device.
  • the organic optoelectronic device may include an organic photoelectronic device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, or the like.
  • the compound for an organic optoelectronic device according to an embodiment may be included in an electrode or an electrode buffer layer in the organic solar cell to improve quantum efficiency.
  • the compound may be used as an electrode material for a gate, a source-drain electrode, or the like in the organic transistor.
  • An embodiment provides an organic light emitting diode including an anode, a cathode, and at least one organic thin layer between the anode and the cathode.
  • the at least one organic thin layer may include the above-described compound for an organic optoelectronic device according to an embodiment.
  • the organic thin layer may include a layer selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking film, and a combination thereof.
  • the at least one layer may include the compound for an organic optoelectronic device according to an embodiment.
  • the electron transport layer (ETL) or the electron injection layer (EIL) may include the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device is included in the emission layer, the compound may be included as a phosphorescent or fluorescent host or as a fluorescent blue dopant material.
  • FIGS. 1 to 5 illustrate cross-sectional views of organic light emitting diodes including the compound for an organic optoelectronic device according to an embodiment.
  • organic light emitting diodes 100 , 200 , 300 , 400 , and 500 may include at least one organic thin layer 105 between an anode 120 and a cathode 110 .
  • the anode 120 may include an anode material laving a large work function to facilitate hole injection into an organic thin layer.
  • the anode material may include, e.g., a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combined metal and oxide such as ZnO:Al or SnO 2 :Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto.
  • the anode 120 may include a transparent electrode including indium tin oxide (ITO).
  • the cathode 110 may include a cathode material having a small work function to facilitate electron injection into an organic thin layer.
  • the cathode material may include, e.g., a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, and the like, or or alloys thereof; or a multi-layered material such as LiF/Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but is not limited thereto.
  • the cathode 110 may include a metal electrode including aluminum.
  • the organic light emitting diode 100 may include an organic thin layer 105 including only an emission layer 130 .
  • the organic light emitting diode 200 may include the emission layer 230 (which may also function as an electron transport layer (ETL)) and a hole transport layer (HTL) 140 layer (that has an excellent binding property with a transparent electrode such as ITO or an excellent hole transporting property).
  • ETL electron transport layer
  • HTL hole transport layer
  • a three-layered organic light emitting diode 300 may include an organic thin layer 105 including an electron transport layer (ETL) 150 , an emission layer 130 , and a hole transport layer (HTL) 140 .
  • the emission layer 130 may be independently installed; and layers having an excellent electron transporting property or an excellent hole transporting property may be separately stacked.
  • a four-layered organic light emitting diode 400 may include an organic thin layer 105 including an electron injection layer (EIL) 160 , an emission layer 130 , a hole transport layer (HTL) 140 , and a hole injection layer (HIL) 170 for binding with the anode 120 of ITO.
  • EIL electron injection layer
  • HTL hole transport layer
  • HIL hole injection layer
  • a five-layered organic light emitting diode 500 may include an organic thin layer 105 including an electron transport layer (ETL) 150 , an emission layer 130 , a hole transport layer (HTL) 140 , and a hole injection layer (HIL) 170 , and may further include an electron injection layer (EIL) 160 to achieve a low voltage.
  • ETL electron transport layer
  • HTL hole transport layer
  • HIL hole injection layer
  • the organic thin layer 105 may include the compound for an organic optoelectronic device according to an embodiment.
  • the compound for an organic optoelectronic device may be used for an electron transport layer (ETL) 150 or electron injection layer (EIL) 160 .
  • ETL electron transport layer
  • EIL electron injection layer
  • the compound for an organic optoelectronic device When the compound for an organic optoelectronic device is included in the emission layer 130 and 230 , the compound may be included as a phosphorescent or fluorescent host or a fluorescent blue dopant.
  • the organic light emitting diode may be fabricated by, e.g., forming an anode on a substrate; forming an organic thin layer (in accordance with a dry coating method such as evaporation, sputtering, plasma plating, and ion plating, or a wet coating method such as spin coating, dipping, and flow coating); and providing a cathode thereon.
  • a dry coating method such as evaporation, sputtering, plasma plating, and ion plating
  • a wet coating method such as spin coating, dipping, and flow coating
  • Another embodiment provides a display device including the organic light emitting diode according to an embodiment.
  • the reactant was refluxed and agitated under a nitrogen atmosphere for 12 hours and then extracted three times with dichloromethane and distilled water.
  • the extracted solution was dried with magnesium sulfate, filtered, and then concentrated under a reduced pressure.
  • the product was purified through silica gel column chromatography by using n-hexane/dichloromethane mixed in a volume ratio of 7:3, obtaining a desired compound, an intermediate M-1, as 43 g of a white solid (yield: 75%).
  • the product was purified through silica gel column chromatography by using n-hexane/dichloromethane in a volume ratio of 7:3, obtaining a desired compound, an intermediate M-2, as 35 g of a white solid (yield: 81%).
  • the resulting reactant was extracted with ethyl acetate, dried with magnesium sulfate, filtered, and then concentrated under a reduced pressure.
  • the resulting product was purified through silica gel column chromatography by using n-hexane/dichloromethane mixed in a volume ratio of 9:1, obtaining a desired compound, an intermediate M-5, as 27 g of a white solid (yield: 89%).
  • the reactant was extracted with ethyl acetate.
  • the extracted solution was dried with magnesium sulfate, filtered, and then concentrated under a reduced pressure.
  • the product was purified through silica gel column chromatography by using n-hexane/dichloromethane mixed in a volume ratio of 9:1, obtaining a desired compound, an intermediate M-6, as 25 g of a white solid (yield: 83%).
  • a glass substrate coated with a 1,500 ⁇ -thick ITO (Indium tin oxide) thin film was cleaned with a distilled water ultrasonic wave.
  • the glass substrate was ultrasonic wave-cleaned with a solvent including one of isopropyl alcohol, acetone, methanol, and the like, and then, cleaned in a plasma cleaner by using oxygen plasma for 5 minutes and moved with a vacuum evaporator.
  • the ITO transparent electrode was used as a positive electrode; and 4,4′-bis[N-[4- ⁇ N,N-bis(3-methylphenyl)amino ⁇ -phenyl]-N-phenylamino]biphenyl (DNTPD) was vacuum-deposited to form a 600 ⁇ -thick hole injection layer (HIL) thereon. Then, the compound A-1 of Example 1 was vacuum-deposited to form a 300 ⁇ -thick hole transport layer (HTL) on the hole injection layer (HIL).
  • HIL hole injection layer
  • HTL hole transport layer
  • ADN 9,10-di-(2-naphthyl)anthracene
  • TBPe 2,5,8,11-tetra(tert-butyl)perylene
  • ETL electron transport layer
  • LiF was vacuum-deposited to be 10 ⁇ thick
  • Al layer was formed to be 1,000 ⁇ thick to fabricate a cathode. Then, the cathode was used to fabricate an organic light emitting diode.
  • An organic light emitting diode was fabricated according to the same method as Example 10, except for using compound A-6 according to Example 6 instead of compound A-1 according to Example 1.
  • An organic light emitting diode was fabricated according to the same method as Example 10 except for using compound A-7 according to Example 7 instead of compound A-1 according to Example 1.
  • An organic light emitting diode was fabricated according to the same method as Example 10 except for using compound B-1 according to Example Ad-1 instead of compound A-1 according to Example 1.
  • An organic light emitting diode was fabricated according to the same method as Example 10 except for using NPB instead of the compound A-1 of Example 1.
  • An organic light emitting diode was fabricated according to the same method as Example 10 except for using HT1 instead of the compound A-1 of Example 1.
  • the compounds according to Examples 1, 6, 7, and Ad-1 had a decomposition temperature close to about 500° C. and thus, very high thermal stability, compared with a Td of 392° C. of carbazole biphenyl (CBP).
  • CBP carbazole biphenyl
  • the compounds according to Examples 1, 6, 7, and Ad-1 had remarkably high glass transition temperatures, compared with a Tg of 90° C. of typically-used compounds for an organic optoelectronic device.
  • the organic light emitting diodes were measured regarding current per unit device by using a current-voltage system (Keithley 2400) while voltage was increased from 0 V to 10 V and current density by dividing the current value by an area.
  • the organic light emitting diodes was measured regarding luminance by using a luminance meter (Minolta Cs-1000 A) while voltage was increased from 0 V to 10 V.
  • the organic light emitting diodes according to Examples 10 to 12 and Ad-2 had remarkably excellent efficiency and half life-span, compared with those of Comparative Examples 1 and 2.
  • the organic light emitting diodes according to Examples 10 to 12 and Ad-2 had remarkably improved half life-span compared with those of Comparative Examples 1 and 2.
  • the organic light emitting diodes according to Examples 12 and Ad-2 had 2,000 hours (h) of half life-span compared with 1250 hours and, thus, more than about 1.6 times improved half life-span.
  • life-span of a device is an important factor in terms of actual commercialization of a device, the organic light emitting diodes according to the Examples turned out to have a satisfactory life-span.
  • the organic light emitting diode transforms electrical energy into light by applying a current to an organic light emitting material.
  • the OLED may have a structure in which a functional organic material layer is interposed between an anode and a cathode.
  • the organic material layer may include a multi-layer including different materials, for example, a hole injection layer (HIL), a hole transport layer (HTL), an emission layer, an electron transport layer (ETL), and an electron injection layer (EIL) in order to improve efficiency and stability of an organic light emitting diode.
  • HIL hole injection layer
  • HTL hole transport layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an organic light emitting diode when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected to an organic material layer. The holes and electrons are recombined to generate excitons having high energy. The generated excitons generate light of a certain wavelength while shifting to a ground state.
  • a phosphorescent light emitting material as well as a fluorescent light emitting material, may be used as a light emitting material for an organic light emitting diode.
  • a phosphorescent material emits light by transiting the electrons from a ground state to an exited state, transiting a singlet exciton to a triplet exciton without radiance through intersystem crossing, and transiting the triplet exciton to a ground state.
  • an organic material layer for an organic light emitting diode may include a light emitting material and a charge transport material, e.g., a hole injection material, a hole transport material, an electron transport material, an electron injection material, or the like.
  • a charge transport material e.g., a hole injection material, a hole transport material, an electron transport material, an electron injection material, or the like.
  • the light emitting material may be classified as blue, green, and red light emitting materials according to emitted colors, and yellow and orange light emitting materials to emit colors near to natural colors.
  • a device When one material is used as a light emitting material, a device may exhibit deteriorated efficiency because interactions among molecules may shift a maximum light emitting wavelength to a long wavelength, may decrease color purity, or may quench light emitting effects. Therefore, a host/dopant system may be used as a light emitting material in order to improve color purity and increase luminous efficiency and stability through energy transfer.
  • a material forming an organic material layer e.g., a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and a light emitting material such as a host and/or a dopant should be stable and have good efficiency.
  • an organic light emitting diode may be classified into a low molecular weight organic light emitting diode and a polymer organic light emitting diode.
  • the low molecular weight organic light emitting diode may be fabricated in a form of a thin film using a vacuum deposit method and thus, may have excellent efficiency and life-span performance.
  • the polymer organic light emitting diode may be fabricated using an inkjet method or a spin coating method and thus, may have a low cost in the initial step while having a large area.
  • Both the low molecular weight organic light emitting diode and the polymer organic light emitting diode exhibit self-light emission, fast response speed, wide photviewing angle, ultra thin film, high image quality, durability, broad operation temperature range, and the like, and thus, draw attention as a next generation display.
  • the low molecular weight organic light emitting diode and the polymer organic light emitting diode self-emit light and thus, have good visibility in a dark place or against an external light, with no need of a backlight. Accordingly, they may be fabricated to have about 1 ⁇ 3 less thickness and weight than a conventional liquid crystal display (LCD).
  • LCD liquid crystal display
  • the low molecular weight organic light emitting diode and the polymer organic light emitting diode may have more than 1,000 times faster response speed than LCD (by a micro second) and thus, may realize a perfect motion picture without an after-image. Accordingly, the low molecular weight organic light emitting diode and the polymer organic light emitting diode may be an optimum display in a multimedia era, since they have 80 times improved efficiency and more than 100 times improved life-span due to remarkable technological development since the first model was developed in the late 1980s. Organic light emitting diodes are finding bigger applications, e.g., a 40 inch organic light emitting diode panel and the like have been developed.
  • Luminous efficiency of a device may require smooth combination of a hole with an electron in an emission layer.
  • an organic material may exhibit slower electron mobility than hole mobility.
  • an electron transport layer ETL may be used to increase electron injection and mobility from a cathode and simultaneously block hole mobility, so that a hole may be efficiently combined with an electron in an emission layer.
  • the embodiments provide a compound capable of providing an organic optoelectronic device having good life span, efficiency, electrochemical stability, and thermal stability.
  • the compound has high hole or electron transporting properties, film stability, thermal stability and high triplet excitation energy.
  • the compound may be used in an emission layer as a hole injection/transport material, a host material, or an electron injection/transport material.
  • the organic photoelectric device including the compound may provide excellent life-span and luminous efficiency while having low driving voltages due to excellent electrochemical and thermal stability.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130241401A1 (en) * 2012-03-15 2013-09-19 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US20140183466A1 (en) * 2012-12-27 2014-07-03 Samsung Display Co., Ltd. Organic light-emitting diode
US20140252327A1 (en) * 2013-03-05 2014-09-11 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US20140291586A1 (en) * 2011-10-27 2014-10-02 Merck Patent Gmbh Materials for electronic devices
US20150034938A1 (en) * 2012-04-24 2015-02-05 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
US20150048332A1 (en) * 2013-08-19 2015-02-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US20150060796A1 (en) * 2013-08-27 2015-03-05 Samsung Display Co., Ltd. Organic light emitting device
US20150236266A1 (en) * 2014-02-14 2015-08-20 Samsung Display Co Ltd Organic light-emitting device
US20170092873A1 (en) * 2015-09-25 2017-03-30 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device and display device
JP2017518279A (ja) * 2014-05-13 2017-07-06 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 化合物、これを含む有機光電子素子および表示装置
US10014477B2 (en) 2012-08-31 2018-07-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
JP2018524289A (ja) * 2015-05-27 2018-08-30 ドク サン ネオルクス カンパニー リミテッド 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置
US10297756B2 (en) 2012-12-27 2019-05-21 Samsung Display Co., Ltd. Organic light-emitting diode
US10355219B2 (en) 2012-08-03 2019-07-16 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US20210119144A1 (en) * 2018-03-16 2021-04-22 Nippon Steel Chemical & Material Co., Ltd. Organic electroluminescent element

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KR101288567B1 (ko) * 2010-06-01 2013-07-22 제일모직주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
US8946695B2 (en) * 2010-12-29 2015-02-03 Lg Chem, Ltd. Compound, and organic light-emitting device using same
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JP2014108938A (ja) 2012-11-30 2014-06-12 Samsung Display Co Ltd アリールアミン化合物及びそれを用いた有機電界発光素子
JP6307689B2 (ja) 2012-12-05 2018-04-11 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． アミン誘導体、有機発光材料及びそれを用いた有機エレクトロルミネッセンス素子
KR102325919B1 (ko) * 2013-10-21 2021-11-12 우미코레 아게 운트 코 카게 방향족 아민의 모노아릴화
WO2016026122A1 (en) 2014-08-21 2016-02-25 Dow Global Technologies Llc Benzocyclobutenes derived compositions, and electronic devices containing the same
JP2016100364A (ja) 2014-11-18 2016-05-30 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
CN105789481B (zh) * 2015-06-10 2018-06-19 广东阿格蕾雅光电材料有限公司 有机电致发光器件
EP3176161A1 (de) 2015-12-02 2017-06-07 Umicore AG & Co. KG Buchwald-hartwig arylierungsverfahren zur herstellung tertiärer arylamine
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EP3502107B1 (de) * 2017-12-20 2022-01-26 Samsung Display Co., Ltd. 1-aminodibenzofuran-basierte verbindung und organische lichtemittierende vorrichtung damit
KR102630640B1 (ko) 2018-06-08 2024-01-30 삼성디스플레이 주식회사 아민계 화합물을 포함한 유기 발광 소자 및 아민계 화합물
JP2018199722A (ja) * 2018-09-14 2018-12-20 株式会社半導体エネルギー研究所 有機化合物及び発光装置
CN109232382B (zh) * 2018-11-15 2021-12-28 长春海谱润斯科技股份有限公司 一种咔唑衍生物及其有机电致发光器件
KR102786420B1 (ko) 2019-06-19 2025-03-27 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 아민 화합물
KR102819937B1 (ko) 2019-09-16 2025-06-13 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함하는 유기 발광 소자
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CN113861043B (zh) * 2020-06-30 2024-07-05 北京鼎材科技有限公司 一种化合物及其应用
KR102870803B1 (ko) 2020-08-20 2025-10-14 삼성디스플레이 주식회사 아민 화합물 및 이를 포함한 발광 소자
CN112624961B (zh) * 2020-12-31 2024-08-20 阜阳欣奕华材料科技有限公司 咔唑类化合物与有机电致发光器件、显示装置

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050221124A1 (en) * 2004-04-02 2005-10-06 Seok-Hwan Hwang Fluorene-based compound and organic electroluminescent display device using the same
US20070231503A1 (en) * 2004-04-02 2007-10-04 Hwang Seok-Hwan Organic light emitting device and flat panel display device comprising the same
US20130087776A1 (en) * 2010-06-01 2013-04-11 Kyoung-Mi LEE Compound for organic photoelectric device and organic photoelectric device including the same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4177707B2 (ja) 2003-03-27 2008-11-05 三井化学株式会社 アミン化合物および該化合物を含有する有機電界発光素子
KR100669716B1 (ko) 2004-07-14 2007-01-16 삼성에스디아이 주식회사 페닐카르바졸 화합물 및 이를 이용한 유기 전계 발광 소자
KR100846586B1 (ko) 2006-05-29 2008-07-16 삼성에스디아이 주식회사 유기 발광 소자 및 이를 구비한 평판 표시 장치
US7663309B2 (en) * 2006-09-28 2010-02-16 Fujifilm Corporation Organic electroluminescent element having plurality of light emitting layers with specific thicknesses
JP5133259B2 (ja) * 2006-11-24 2013-01-30 出光興産株式会社 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
TWI441898B (zh) 2007-09-28 2014-06-21 Idemitsu Kosan Co 有機ｅｌ元件
KR20090048299A (ko) 2007-11-08 2009-05-13 주식회사 엘지화학 새로운 유기 발광 소자 재료 및 이를 이용한 유기 발광소자
WO2009061145A1 (en) * 2007-11-08 2009-05-14 Lg Chem, Ltd. New compound and organic light emitting device using the same
KR20120022859A (ko) * 2009-04-01 2012-03-12 이데미쓰 고산 가부시키가이샤 유기 전기발광 소자

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050221124A1 (en) * 2004-04-02 2005-10-06 Seok-Hwan Hwang Fluorene-based compound and organic electroluminescent display device using the same
US20070231503A1 (en) * 2004-04-02 2007-10-04 Hwang Seok-Hwan Organic light emitting device and flat panel display device comprising the same
US20130087776A1 (en) * 2010-06-01 2013-04-11 Kyoung-Mi LEE Compound for organic photoelectric device and organic photoelectric device including the same

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140291586A1 (en) * 2011-10-27 2014-10-02 Merck Patent Gmbh Materials for electronic devices
US9812643B2 (en) * 2011-10-27 2017-11-07 Merck Patent Gmbh Materials for electronic devices
US9548459B2 (en) 2012-03-15 2017-01-17 Universal Display Corporation Organic materials for organic light emitting devices
US20130241401A1 (en) * 2012-03-15 2013-09-19 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9054323B2 (en) * 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US20150034938A1 (en) * 2012-04-24 2015-02-05 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
US9324948B2 (en) * 2012-04-24 2016-04-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
US10355219B2 (en) 2012-08-03 2019-07-16 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US11444246B2 (en) 2012-08-31 2022-09-13 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US11362279B2 (en) 2012-08-31 2022-06-14 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US10014477B2 (en) 2012-08-31 2018-07-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US10297756B2 (en) 2012-12-27 2019-05-21 Samsung Display Co., Ltd. Organic light-emitting diode
US9590184B2 (en) * 2012-12-27 2017-03-07 Samsung Display Co., Ltd. Organic light-emitting diode
US20140183466A1 (en) * 2012-12-27 2014-07-03 Samsung Display Co., Ltd. Organic light-emitting diode
US9590185B2 (en) * 2013-03-05 2017-03-07 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US20140252327A1 (en) * 2013-03-05 2014-09-11 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US20150048332A1 (en) * 2013-08-19 2015-02-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US9768388B2 (en) * 2013-08-19 2017-09-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting diode including the same
US9525141B2 (en) * 2013-08-27 2016-12-20 Samsung Display Co., Ltd. Organic light emitting device
US20150060796A1 (en) * 2013-08-27 2015-03-05 Samsung Display Co., Ltd. Organic light emitting device
US9601703B2 (en) * 2014-02-14 2017-03-21 Samsung Display Co., Ltd. Organic light-emitting device
US20150236266A1 (en) * 2014-02-14 2015-08-20 Samsung Display Co Ltd Organic light-emitting device
JP2017518279A (ja) * 2014-05-13 2017-07-06 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 化合物、これを含む有機光電子素子および表示装置
US11563179B2 (en) 2014-05-13 2023-01-24 Samsung Sdi Co., Ltd. Compound, organic optoelectronic element comprising same and display device thereof
JP2018524289A (ja) * 2015-05-27 2018-08-30 ドク サン ネオルクス カンパニー リミテッド 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置
US11380846B2 (en) 2015-05-27 2022-07-05 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
US20170092873A1 (en) * 2015-09-25 2017-03-30 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device and display device
US20210119144A1 (en) * 2018-03-16 2021-04-22 Nippon Steel Chemical & Material Co., Ltd. Organic electroluminescent element
US12484443B2 (en) * 2018-03-16 2025-11-25 Nippon Steel Chemical & Material Co., Ltd. Organic electroluminescent element

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