WO2014021571A1 - Composé à base de carbazole pour un dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé à base de carbazole pour un dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2014021571A1
WO2014021571A1 PCT/KR2013/006463 KR2013006463W WO2014021571A1 WO 2014021571 A1 WO2014021571 A1 WO 2014021571A1 KR 2013006463 W KR2013006463 W KR 2013006463W WO 2014021571 A1 WO2014021571 A1 WO 2014021571A1
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substituted
unsubstituted
group
fused
heterocycloalkyl
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Yong-Jun Shin
Jeong Ho Park
Suk Woon JUN
Ju-Sik Kang
Yu-Mi Chang
Nam-Choul Yang
Jae-Kyun Park
Song Lee
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Sk Chemicals Co., Ltd.
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Priority claimed from KR1020130080451A external-priority patent/KR20140017428A/ko
Application filed by Sk Chemicals Co., Ltd. filed Critical Sk Chemicals Co., Ltd.
Publication of WO2014021571A1 publication Critical patent/WO2014021571A1/fr

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    • 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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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/14—Carrier transporting layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly, to a carbazole-based compound for an organic electroluminescent device, having high light emission efficiency and low driving voltage, and to an organic electroluminescent device including the same.
  • Organic electroluminescent (EL) devices have a simpler structure, various processing advantages, higher brightness, superior viewing angle properties, quicker response rate, and a lower driving voltage compared to other flat panel displays such as liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc., and are thus being thoroughly developed so as to be utilized as light sources of flat panel displays such as wall-mountable TVs, etc. or backlight units of the displays, illuminators, advertisement boards and so on.
  • LCDs liquid crystal displays
  • PDPs plasma display panels
  • FEDs field emission displays
  • Hole transport materials for use in organic EL devices which have been known to date, are problematic because thin films formed therefrom using vacuum deposition are thermally and electrically unstable, and thus may rapidly crystallize due to heat generated upon device driving and also the film materials may change, undesirably deteriorating the light emission efficiency of the devices. Further, non-emission parts referred to as dark spots may increasingly occur, and the voltage may increase upon constant-current driving, undesirably damaging the devices.
  • organic EL devices using a phosphorescent light emitting material do not confine a triplet exciton produced in the light emitting material of a light emitting layer due to low triplet energy, undesirably lowering the light emission efficiency of the devices.
  • an object of the present invention is to provide a compound for an organic EL device, which may have high thermal stability, high triplet energy and hole transport capability.
  • Another object of the present invention is to provide an organic EL device, which includes the compound as above and is thus improved in thermal stability and light emission efficiency, and in which the above compound is used as a hole transport layer material, thereby confining a triplet exciton of a phosphorescent light emitting material, ultimately improving efficiency of the organic EL device.
  • an aspect of the present invention provides a compound for an organic EL device, as represented by Chemical Formula 1 below.
  • Ar 1 is a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • Ar 2 to Ar 9 are identical to or different from each other, and Ar 2 to Ar 9 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 2 and Ar 3 , Ar 4 and Ar 5 , Ar 6 and Ar 7 , and Ar 8 and Ar 9 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween,
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 1 and R 2 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • R 3 and R 4 are identical to or different from each other, and R 3 and R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 3 and R 4 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • n 0 or 1
  • n 0 or 1.
  • Another aspect of the present invention provides a compound for an organic EL device, as represented by Chemical Formula 2 below.
  • Ar 1 is a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • Ar 2 to Ar 9 are identical to or different from each other, and Ar 2 to Ar 9 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 2 and Ar 3 , Ar 4 and Ar 5 , Ar 6 and Ar 7 , and Ar 8 and Ar 9 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween,
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 1 and R 2 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • R 3 and R 4 are identical to or different from each other, and R 3 and R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 3 and R 4 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • n 0 or 1
  • n 0 or 1.
  • Another aspect of the present invention provides a compound for an organic EL device, as represented by Chemical Formula 3 below.
  • Ar 1 is a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • Ar 2 to Ar 9 are identical to or different from each other, and Ar 2 to Ar 9 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 2 and Ar 3 , Ar 4 and Ar 5 , Ar 6 and Ar 7 , and Ar 8 and Ar 9 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween,
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 1 and R 2 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • R 3 and R 4 are identical to or different from each other, and R 3 and R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R 3 and R 4 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or un
  • n 0 or 1
  • n 0 or 1.
  • Examples of the substituted or unsubstituted C6 to C30 aryl group may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted perylenyl group.
  • Examples of the substituted or unsubstituted C1 to C30 heteroaryl group may include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazin
  • a substituted or unsubstituted pyridinyl group a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl
  • Another aspect of the present invention provides a compound for an organic EL device, which is any one selected from among compounds 1 to 33 represented by the following chemical formulas.
  • an organic electroluminescent (EL) device including the compound for an organic EL device according to the present invention may be provided.
  • an organic EL device may include a first electrode, a second electrode, and a single organic layer or a plurality of organic layers between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers may include the compound for an organic EL device according to the present invention.
  • the single organic layer or the plurality of organic layers may include a light emitting layer.
  • the plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include one or more selected from among an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer and a hole injection layer.
  • the light emitting layer may include a host and a dopant.
  • carbazole-based compound coupled with phenyl group is substituted with one or two diaryl amine on ortho or meta position of phenyl group.
  • the compound is contained in the organic layer of an organic EL device, and the use of the compound as a phosphorescent light emitting material in the organic EL device enables to increase the triplet energy, thus obtaining an organic EL device having improved thermal stability and light emission efficiency.
  • FIG. 1 is a cross-sectional view illustrating an organic EL device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view illustrating an organic EL device according to another embodiment of the present invention.
  • the present invention may be variously modified, and may have a variety of embodiments, and is intended to illustrate specific embodiments. However, the following description does not limit the present invention to specific embodiments, and should be understood to include all variations, equivalents or substitutions within the spirit and scope of the present invention. Furthermore, in the description of the present invention, when it is determined that the detailed description of the related art would obscure the gist of the present invention, the description thereof will be omitted.
  • first a first component
  • second a second component
  • first component a first component
  • any one component when any one component is mentioned to be “formed” or “stacked” on another component, it may be directly attached to the entire surface or one surface of another component, or a further component may be additionally interposed therebetween.
  • the singular expression includes a plural expression.
  • the terms “include” and “have” are used to designate the presence of features, numbers, steps, operations, components, parts or combinations thereof described in the specification, not intending to exclude the presence or additional possibility of one or more different features, numbers, steps, operations, components, parts or combinations thereof are not excluded.
  • valence bond means a single bond, a double bond or a triple bond.
  • substituted means that at least one hydrogen on a substituent or a compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, a C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.
  • two adjacent substituents may be fused to form a ring.
  • hetero means a functional group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon.
  • the term “combination thereof” means that two or more substituents are coupled with each other by a linker or two or more substituents are condensed to each other.
  • hydrogen means hydrogen, deuterium or tritium.
  • alkyl group means an aliphatic hydrocarbon group.
  • the alkyl group may be a “saturated alkyl group” without any double bond or triple bond.
  • the alkyl group may be an “unsaturated alkyl group” with at least one double bond or triple bond.
  • alkenylene group means a functional group having at least one carbon-carbon double bond between at least two carbon atoms
  • alkynylene group means a functional group having at least one carbon-carbon triple bond between at least two carbon atoms.
  • the alkyl group may be branched, linear or cyclic, regardless of whether it is saturated or unsaturated.
  • the alkyl group may be a C1 to C30 alkyl group, preferably a C1 to C20 alkyl, more preferably a C1 to C10 alkyl group, and much more preferably a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group indicates an alkyl chain containing 1 ⁇ 4 carbon atoms, particularly an alkyl chain which is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl.
  • alkyl group examples 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, a cyclohexyl group, etc.
  • the “amine group” includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.
  • cycloalkyl group refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.
  • heterocycloalkyl group means a cycloalkyl group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heterocycloalkyl group is a fused ring, each ring may contain 1 ⁇ 4 heteroatoms.
  • aromatic group means a cyclic functional group where all ring atoms have p-orbitals, and these p-orbitals form conjugation. Specific examples thereof include an aryl group and a heteroaryl group.
  • aryl group refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.
  • heteroaryl group means an aryl group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heteroalkyl group is a fused ring, each ring may contain 1 ⁇ 4 heteroatoms.
  • the number of ring atoms is the sum of the number of carbons and the number of non-carbon atoms.
  • alkyl and aryl are used in combination as in “alkylaryl group” or “arylalkyl group,” “alkyl” and “aryl” respectively have the meanings as above.
  • arylalkyl group means an aryl substituted alkyl radical such as benzyl, and is incorporated in the alkyl group.
  • alkylaryl group means an alkyl substituted aryl radical, and is incorporated in the aryl group.
  • an organic EL device 1 including the compound for an organic EL device according to the present invention may be provided.
  • an organic EL device includes a first electrode 110, a second electrode 150, and a single organic layer or a plurality of organic layers 130 between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers 130 may include the compound for an organic EL device according to the present invention.
  • the single organic layer or the plurality of organic layers 130 may include a light emitting layer 134.
  • the plurality of organic layers 130 include a light emitting layer 134, and the plurality of organic layers 130 may further include one or more selected from among an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole transport layer 136 and a hole injection layer 137.
  • the light emitting layer 134 may include a host and a dopant.
  • the organic EL device is preferably supported by a transparent substrate.
  • the material for the transparent substrate is not particularly limited so long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof may include glass, a transparent plastic film, etc.
  • the anode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of 4 eV or more. Specific examples thereof may include Au metal or a transparent conductive material such as CuI, ITO (indium tin oxide), SnO 2 and ZnO.
  • the thickness of the anode film is preferably set to 10 ⁇ 200 nm.
  • the cathode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of less than 4 eV. Specific examples thereof may include Na, a Na-K alloy, calcium, magnesium, lithium, a lithium alloy, indium, aluminum, a magnesium alloy, or an aluminum alloy. In addition, aluminum/AlO 2 , aluminum/lithium, magnesium/silver or magnesium/indium may be used. The thickness of the cathode film is preferably set to 10 ⁇ 200 nm.
  • one or more electrodes preferably have a light transmittance of 10% or more.
  • the sheet resistance of the electrodes is preferably hundreds of ⁇ /mm or less.
  • the thickness of the electrodes falls in the range of 10 nm ⁇ 1 ⁇ m, and preferably 10 ⁇ 400 nm.
  • Such electrodes may be manufactured in the form of a thin film using the above electrode material via vapor deposition such as chemical vapor deposition (CVD), physical vapor deposition (PVD) or the like, or sputtering.
  • CVD chemical vapor deposition
  • PVD physical vapor deposition
  • a hole transport material, a hole injection material, a light emitting layer material, a host material for a light emitting layer, an electron transport material, and an electron injection material may be used alone in each organic layer, or may be used in selective combination with the compound for an organic EL device according to the present invention.
  • Examples of the hole transport material may include porphyrin compound derivatives including N,N-dicarbazolyl-3,5-benzene (mCP), poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N'N'-tetraphenyl-4,4'-diaminobiphenyl, 1,10,15,20-te
  • Examples of the electron transport material may include diphenylphosphine oxide-4-(triphenylsilyl)phenyl (TSPO1), Alq 3 , 2,5-diaryl sylol derivatives (PyPySPyPy), perfluorinated compounds (PF-6P), octasubstituted cyclooctatetraene compounds (COTs), etc.
  • TSPO1 diphenylphosphine oxide-4-(triphenylsilyl)phenyl
  • Alq 3 2,5-diaryl sylol derivatives
  • PF-6P perfluorinated compounds
  • COTs octasubstituted cyclooctatetraene compounds
  • an electron injection layer, an electron transport layer, a hole transport layer and a hole injection layer may be provided in the form of a single layer containing one or more kinds of the above compound, or may be provided in the form of a plurality of stacked layers containing different kinds of compounds.
  • the light emitting material may include, for example, photoluminescent fluorescent materials, fluorescent brighteners, laser dyes, organic scintillators and fluorescence analysis reagents.
  • specific examples thereof include carbazole-based compounds, phosphine oxide-based compounds, carbazole-based phosphine oxide compounds, polyaromatic compounds including bis((3,5-difluoro-4-cyanophenyl)pyridine)iridium picolinate (FCNIrpic), tris(8-hydroxyquinoline) aluminum (Alq 3 ), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds including quaterphenyl, scintillators for liquid scintillation including 1,4-bis(2-methylstyryl)benzene, 1,4-bis(4-methylstyryl)benzene, 1,4-bis(4-methyl-5-phenyl-2-
  • Each layer of the organic EL device according to the present invention may be provided in the form of a thin film using a known process such as vacuum deposition, spin coating or casting, or may be manufactured using each layer material.
  • the thickness of each layer is not particularly limited, but may be appropriately set depending on the material properties , and may be typically determined in the range of 2 ⁇ 5,000 nm.
  • the compound for an organic EL device according to the present invention may be subjected to vacuum deposition, a thin film formation process is simple and a uniform thin film which does not substantially have pin holes may be easily obtained.
  • a glass substrate coated with an ITO(Indium Tin Oxide) thin film having a thickness of 100 nm was ultrasonically washed with an isopropyl alcohol solvent, dried, placed in a plasma cleaning system so that the substrate was cleaned using oxygen plasma for 5 min, and then transferred into a vacuum deposition system.
  • the ITO transparent electrode thus prepared was used as an anode, and DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)-phenyl]-biphenyl-4,4'-diamine] was vacuum deposited on the ITO substrate, thus forming a hole injection layer having a thickness of 55 nm.
  • NPB N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine
  • NPB N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine
  • a second hole transport layer was formed to a thickness of 10 nm using Compound 1 on the first hole transport layer.
  • CBP 4,4-N,N-dicarbazolebiphenyl
  • 6 vol% of Ir(PPy) 3 tris(2-phenylpyridine)iridium] as a dopant were vacuum deposited to a thickness of 25 nm on the second hole transport layer, thus forming a light emitting layer.
  • an electron transport layer was formed to a thickness of 30 nm using Bphen [4,7-diphenyl-1,10-phenanthroline] on the light emitting layer.
  • 2 nm thick Liq [lithium quinolate] and 100 nm thick Al were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic EL device.
  • Comparative Device Example 1 Manufacture of organic EL device including NPB as second hole transport layer
  • the brightness was measured using a brightness meter (Minolta CS-2000), and the measured brightness value was divided by the current value, thus obtaining brightness efficiency.
  • the color coordinates were measured using a brightness meter (Minolta CS-2000).
  • carbazole-based compound coupled with phenyl group is substituted with one or two diaryl amine on ortho or meta position of phenyl group.
  • the compound is contained in the organic layer of an organic EL device, and the use of the compound as a phosphorescent light emitting material in the organic EL device enables to increase the triplet energy, thus obtaining an organic EL device having improved thermal stability and light emission efficiency.

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

Abstract

L'invention concerne un composé pour un dispositif électroluminescent organique et un dispositif électroluminescent organique le comprenant. Le dispositif électroluminescent organique comprenant le composé est amélioré en stabilité thermique et en efficacité d'émission de lumière. Lorsque ce composé est utilisé comme matière de couche de transport de trous, l'énergie triplet de la matière émettant une lumière phosphorescente dans le dispositif électroluminescent organique est augmentée, améliorant ainsi l'efficacité du dispositif électroluminescent organique.
PCT/KR2013/006463 2012-07-31 2013-07-19 Composé à base de carbazole pour un dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant WO2014021571A1 (fr)

Applications Claiming Priority (4)

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KR20120083930 2012-07-31
KR10-2012-0083930 2012-07-31
KR1020130080451A KR20140017428A (ko) 2012-07-31 2013-07-09 카바졸계 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자
KR10-2013-0080451 2013-07-09

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105418485A (zh) * 2015-12-22 2016-03-23 吉林奥来德光电材料股份有限公司 一种新的绿光主体化合物及其制备方法和应用
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
WO2016081583A1 (fr) * 2014-11-20 2016-05-26 E. I. Du Pont De Nemours And Company Matériau de transport de trous
CN106117522A (zh) * 2015-05-06 2016-11-16 E.I.内穆尔杜邦公司 空穴传输材料
CN113292481A (zh) * 2021-03-31 2021-08-24 吉林奥来德光电材料股份有限公司 有机电致发光化合物、其制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09310066A (ja) * 1996-05-23 1997-12-02 Idemitsu Kosan Co Ltd 有機電界発光素子
US20020045061A1 (en) * 2000-03-27 2002-04-18 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
JP2009021335A (ja) * 2007-07-11 2009-01-29 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20090028943A (ko) * 2007-09-17 2009-03-20 (주)루디스 정공주입층/정공수송층 물질 및 이를 포함하는유기전계발광소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09310066A (ja) * 1996-05-23 1997-12-02 Idemitsu Kosan Co Ltd 有機電界発光素子
US20020045061A1 (en) * 2000-03-27 2002-04-18 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
JP2009021335A (ja) * 2007-07-11 2009-01-29 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20090028943A (ko) * 2007-09-17 2009-03-20 (주)루디스 정공주입층/정공수송층 물질 및 이를 포함하는유기전계발광소자

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US9893295B2 (en) * 2014-10-01 2018-02-13 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10439140B2 (en) 2014-11-20 2019-10-08 Lg Chem, Ltd. Hole transport materials
WO2016081583A1 (fr) * 2014-11-20 2016-05-26 E. I. Du Pont De Nemours And Company Matériau de transport de trous
US10879467B2 (en) 2014-11-20 2020-12-29 Lg Chem, Ltd. Hole transport materials
CN107108861A (zh) * 2014-11-20 2017-08-29 E.I.内穆尔杜邦公司 空穴传输材料
CN107108861B (zh) * 2014-11-20 2019-11-12 株式会社Lg化学 空穴传输材料
CN106117522A (zh) * 2015-05-06 2016-11-16 E.I.内穆尔杜邦公司 空穴传输材料
US9954174B2 (en) 2015-05-06 2018-04-24 E I Du Pont De Nemours And Company Hole transport materials
US10749111B2 (en) 2015-05-06 2020-08-18 Lg Chem, Ltd. Crosslinkable hole transport materials
CN105418485B (zh) * 2015-12-22 2019-04-19 吉林奥来德光电材料股份有限公司 一种新的绿光主体化合物及其制备方法和应用
CN105418485A (zh) * 2015-12-22 2016-03-23 吉林奥来德光电材料股份有限公司 一种新的绿光主体化合物及其制备方法和应用
CN113292481A (zh) * 2021-03-31 2021-08-24 吉林奥来德光电材料股份有限公司 有机电致发光化合物、其制备方法和应用

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