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WO2015041492A1 - Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2015041492A1
WO2015041492A1 PCT/KR2014/008783 KR2014008783W WO2015041492A1 WO 2015041492 A1 WO2015041492 A1 WO 2015041492A1 KR 2014008783 W KR2014008783 W KR 2014008783W WO 2015041492 A1 WO2015041492 A1 WO 2015041492A1
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Ju-Sik Kang
Jeong Ho Park
Suk Woon JUN
Yong-Jun Shin
Yu-Mi Chang
Nam-Choul Yang
Jae-Kyun Park
Song Lee
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SK Chemicals Co Ltd
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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 an amine-based compound for an organic electroluminescent device, having excellent light emission efficiency, 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 high 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 in contact with a light emitting layer, thereby increasing a triplet energy, 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.
  • m1 to m4 are each independently 0 or 1
  • n1 to n3 are are each independently 0 or 1
  • Ar 1 to Ar 16 are identical to or different from each other, and Ar 1 to Ar 16 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 at least one of Ar 1 to Ar 16 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , Ar 7 and Ar 8 , Ar 9 and Ar 10
  • R 1 to R 6 are identical to or different from each other, and R 1 to R 6 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.
  • m1 to m4 are each independently 0 or 1
  • Ar 1 to Ar 16 are identical to or different from each other, and Ar 1 to Ar 16 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 at least one of Ar 1 to Ar 16 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , Ar 7 and Ar 8 , Ar 9 and Ar 10
  • R 1 to R 6 are identical to or different from each other, and R 1 to R 6 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.
  • Ar 1 to Ar 16 are identical to or different from each other, and Ar 1 to Ar 16 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, or at least one of Ar 1 to Ar 16 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , Ar 7 and Ar 8 , Ar 9 and Ar 10 , Ar 11 and Ar 12 , Ar 13 and Ar 14 ,
  • X 1 and X 2 are identical to or different from each other, and X 1 and X 2 are each independently a oxygen atom, a sulfur atom, , or ,
  • Ar 17 is 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,
  • R 26 and R 27 are identical to or different from each other, and R 26 and R 27 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, and
  • R 7 to R 25 are identical to or different from each other, and R 7 to R 25 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.
  • 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
  • the compound for an organic EL device is any one selected from among compounds 1 to 24 represented by the following chemical formulas.
  • an organic electroluminescent (EL) device including the compounds 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.
  • phenyl group is bonded at central benzene ring, and diarylamine is bonded at the above phenyl group thereby realizing improved HOMO and LUMO energy level, and thus obtaining a compound for an organic EL device which may have high triplet energy by separating HOMO and LUMO.
  • the present invention may improve thermal stability and light emission efficiency of the organic EL device by using the above compound, and thus improving efficiency of the organic EL device by increasing a triplet energy of the phosphorescent material using the above compound as hole transport layer material which may contact with light emitting layer.
  • 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 C50 amine group, a nitro group, a silyl group, a C1 to C50 alkyl group, a C1 to C50 alkylsilyl group, a C3 to C50 cycloalkyl group, a C1 to C50 heterocycloalkyl group, a C6 to C50 aryl group, a C1 to C50 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.
  • halogen group the hydroxyl group, the amino group, the C1 to C50 amine group, the silyl group, the C1 to C50 alkyl group,
  • 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 C50 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, at least one 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, at least one 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.
  • carbon atom on the ⁇ position of any one atom refers to a carbon atom adjacent to another atom linked with the one atom.
  • carbon atom on the ⁇ position of a nitrogen atom is a carbon atom indicated by the arrow in the following chemical formula.
  • 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.
  • ITO indium tin oxide
  • 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 30 nm.
  • HATCN 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile
  • TBDB N,N,N',N'-tetra(4-biphenyl)-diaminobiphenylene
  • a second hole transport layer was formed to a thickness of 40 nm using compound 9 on the first hole transport layer.
  • an electron transport layer was formed to a thickness of 20 nm using DNABI [2-[4-(9,10-Di-naphthalen-2-yl-anthracen-2-yl)-phenyl]-1-phenyl-1H-benzoimidazole] on the light emitting layer.
  • DNABI DNABI [2-[4-(9,10-Di-naphthalen-2-yl-anthracen-2-yl)-phenyl]-1-phenyl-1H-benzoimidazole] 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.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 10 was used as a second hole transport layer instead of Compound 9.
  • Comparative Device Example 1 Manufacture of organic EL device including TBDB as second hole transport layer
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that TBDB was used as second hole transport layer instead of Compound 9.
  • 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. Also, the color coordinates were measured using a brightness meter (Minolta CS-2000).
  • phenyl group is bonded at central benzene ring, and diarylamine is bonded at the above phenyl group thereby realizing improved HOMO and LUMO energy level, and thus obtaining a compound for an organic EL device which may have high triplet energy by separating HOMO and LUMO.
  • the present invention may improve thermal stability and light emission efficiency of the organic EL device by using the above compound, and thus improving efficiency of the organic EL device by increasing a triplet energy of the phosphorescent material using the above compound as hole transport layer material which may contact with light emitting layer.

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Abstract

La présente invention concerne un composé pour un dispositif électroluminescent organique et un dispositif électroluminescent organique le comprenant. Selon la présente invention, le dispositif électroluminescent organique comprenant le composé peut avoir une stabilité thermique et un rendement d'émission lumineuse améliorés. Quand le composé est utilisé en tant que matériau de couche de transport de trous, on a une augmentation d'une énergie triplet d'un matériau électroluminescent phosphorescent, ce qui améliore l'efficacité du dispositif électroluminescent organique.
PCT/KR2014/008783 2013-09-23 2014-09-22 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant Ceased WO2015041492A1 (fr)

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WO2017148565A1 (fr) * 2016-03-03 2017-09-08 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
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JP2018118933A (ja) * 2017-01-26 2018-08-02 株式会社リコー エレクトロクロミック化合物、エレクトロクロミック組成物およびエレクトロクロミック素子
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US10693079B2 (en) 2015-06-17 2020-06-23 Samsung Display Co., Ltd. Mono amine derivatives and organic electroluminescent device including the same
US11261176B2 (en) 2017-01-26 2022-03-01 Lg Chem, Ltd. Amine-based compound and organic light emitting device using the same
US11358946B2 (en) * 2016-09-20 2022-06-14 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using same and electronic device therefor
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005112765A (ja) * 2003-10-07 2005-04-28 Mitsui Chemicals Inc 複素環化合物および該化合物を含有する有機電界発光素子
JP2009267255A (ja) * 2008-04-28 2009-11-12 Idemitsu Kosan 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
WO2010095621A1 (fr) * 2009-02-18 2010-08-26 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique
WO2011004639A1 (fr) * 2009-07-07 2011-01-13 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, nouveau composé, dispositif d'éclairage et dispositif d'affichage
US20120018714A1 (en) * 2001-03-01 2012-01-26 Konica Minolta Holdings, Inc. Organic electroluminescent device, display apparatus, and lighting apparatus
JP2013016717A (ja) * 2011-07-06 2013-01-24 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

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120018714A1 (en) * 2001-03-01 2012-01-26 Konica Minolta Holdings, Inc. Organic electroluminescent device, display apparatus, and lighting apparatus
JP2005112765A (ja) * 2003-10-07 2005-04-28 Mitsui Chemicals Inc 複素環化合物および該化合物を含有する有機電界発光素子
JP2009267255A (ja) * 2008-04-28 2009-11-12 Idemitsu Kosan 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
WO2010095621A1 (fr) * 2009-02-18 2010-08-26 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique
WO2011004639A1 (fr) * 2009-07-07 2011-01-13 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, nouveau composé, dispositif d'éclairage et dispositif d'affichage
JP2013016717A (ja) * 2011-07-06 2013-01-24 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

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US11050025B2 (en) 2014-10-28 2021-06-29 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
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US10205102B2 (en) 2015-06-17 2019-02-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
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US12041848B2 (en) * 2015-12-08 2024-07-16 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
JP2019510011A (ja) * 2016-03-03 2019-04-11 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
US12065431B2 (en) 2016-03-03 2024-08-20 Merck Patent Gmbh Materials for organic electroluminescent devices
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US12441715B2 (en) 2016-03-03 2025-10-14 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2017148565A1 (fr) * 2016-03-03 2017-09-08 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US10961230B2 (en) 2016-03-03 2021-03-30 Merck Patent Gmbh Materials for organic electroluminescent devices
JP7080821B2 (ja) 2016-03-03 2022-06-06 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
US11608327B2 (en) 2016-03-03 2023-03-21 Merck Patent Gmbh Materials for organic electroluminescent devices
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US10975296B2 (en) 2017-01-26 2021-04-13 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic element
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