WO2016036031A1 - Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant le composé - Google Patents

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

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WO2016036031A1
WO2016036031A1 PCT/KR2015/008687 KR2015008687W WO2016036031A1 WO 2016036031 A1 WO2016036031 A1 WO 2016036031A1 KR 2015008687 W KR2015008687 W KR 2015008687W WO 2016036031 A1 WO2016036031 A1 WO 2016036031A1
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unsubstituted
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compound
atom
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Song Lee
Yu-Mi Chang
Suk Woon JUN
Jeong Ho Park
Ju-Sik Kang
Yong-Jun Shin
Nam-Choul Yang
Jae-Kyun Park
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Sk Chemicals Co., Ltd.
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    • 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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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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 compound for an organic electroluminescent device, improving the 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
  • the light emitting materials can be divided into a host and a light emitting materials (dopant).
  • the light emitting materials can be divided into the fluorescent and the phosphorescent materials in accordance with the light emitting mechanism. If the fluorescent light emitting materials are used, the fluorescent dopant materials are needed to satisfy high efficiency, high colorimetric purity and long lifetime.
  • an object of the present invention is to provide a compound for an organic EL devices which may be used as a dopant of a fluorescent light emitting layer having neutral blue light emission with high electrical stability, high efficiency, high colorimetric purity and long lifetime, and an organic electroluminescent device including the same.
  • an organic electroluminescent device including the compounds for an organic EL devices substituted with alkyl group and silyl group at the 4 and 9 position of the pyrene can be implemented high efficiency, high colorimetric purity and long lifetime.
  • an aspect of the present invention provides a compound for an organic EL device, as represented by Chemical Formula 1 below.
  • 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 deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R 1 to R 6 form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,
  • X 1 and X 2 are identical to or different from each other, and X 1 and X 2 are each independently a carbon atom or a silicon atom,
  • n 0 or 1
  • R 7 to R 14 are identical to or different from each other, and R 7 to R 14 are each independently a hydrogen atom, a deuterium 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 7 to R 14 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
  • the compound for an organic EL device is represented by Chemical Formula 2 below.
  • 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 deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R 1 to R 6 form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,
  • X 1 and X 2 are identical to or different from each other, and X 1 and X 2 are each independently a carbon atom or a silicon atom,
  • n 0 or 1
  • R 7 to R 14 are identical to or different from each other, and R 7 to R 14 are each independently a hydrogen atom, a deuterium 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 7 to R 14 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
  • the compound for an organic EL device is represented by Chemical Formula 3 below.
  • 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 deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R 1 to R 6 form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,
  • X 1 and X 2 are identical to or different from each other, and, X 1 and X 2 are each independently a carbon atom or a silicon atom,
  • n 0 or 1
  • R 7 to R 9 , R 11 to R 13 , R 15 and R 16 are identical to or different from each other, and R 7 to R 9 , R 11 to R 13 , R 15 and R 16 are each independently a hydrogen atom, a deuterium 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 7 to R 9 , R 11 to R 13 , R 15 and R 16 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 un
  • Y 1 and Y 2 are identical to or different from each other, and, Y 1 and Y 2 are each independently a oxygen atom, a sulfur atom or , and
  • R 17 and R 18 are identical to or different from each other, and R 17 and R 18 are each independently a hydrogen atom, a deuterium 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.
  • the compound for an organic EL device is represented by Chemical Formula 4 below.
  • 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 deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R 1 to R 6 form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,
  • X 1 and X 2 are identical to or different from each other, and, X 1 and X 2 are each independently a carbon atom or a silicon atom,
  • n 0 or 1
  • R 7 to R 9 , R 11 to R 13 , R 15 and R 16 are identical to or different from each other, and R 7 to R 9 , R 11 to R 13 , R 15 and R 16 are each independently a hydrogen atom, a deuterium 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 7 to R 9 , R 11 to R 13 , R 15 and R 16 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 un
  • Y 1 and Y 2 are identical to or different from each other, and, Y 1 and Y 2 are each independently a oxygen atom, a sulfur atom or , and
  • R 17 and R 18 are identical to or different from each other, and R 17 and R 18 are each independently a hydrogen atom, a deuterium 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 C2 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 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.
  • the present invention provides a compound for an organic EL device which may be used as a dopant of a fluorescent light emitting layer having neutral blue light emission with high electrical stability, and improving colorimetric purity, light emission efficiency, and lifetime of fluorescent light-emitting material, and an organic electroluminescent device including the same.
  • the compound for an organic EL devices substituted with alkyl group and silyl group at the 4 and 9 positions of the pyrene can implement the organic EL device which have high efficiency, high colorimetric purity and long lifetime, compared with a organic EL device including a compound substituted with alkyl group and silyl group at the other positions of the pyrene.
  • 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 silyl group, a C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C6 to C30 arylsilyl group, a C7 to C30 alkylarylsilyl group, a C7 to C30 arylalkylsilyl 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, 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.
  • 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 150 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 HT-1 was vacuum deposited on the ITO substrate, thus forming a hole injection layer having a thickness of 65 nm. Subsequently, HT-2 was deposited to a thickness of 30 nm, thus forming a hole transport layer, and compound 1 as a dopant, was deposited to 0.1nm/sec of deposition speed of BH-1 and 0.003nm/sec of deposition speed of compound 1, and compound 1 was doped with 3% of deposition speed rate, thus forming a light emitting layer to a thickness of 25 nm on the hole transport layer.
  • an electron transport layer was formed to a thickness of 30 nm by depositing ET-1 on the light emitting layer, and lithium fluoride layer having a thickness of 1 nm and Al layer having a thickness of 50 nm were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic EL device.
  • the deposition speeds of HT-1, HT-2 and ET-2 were respectively 0.1 nm/sec, the deposition speed of lithium fluoride was 0.02 nm/sec, and the deposition speed of Al was 0.2 nm/sec.

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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 destiné à un dispositif électroluminescent organique et un dispositif électroluminescent organique comprenant le composé. La présente invention peut fournir un composé pour dispositif électroluminescent organique qui peut être utilisé en tant que dopant de la couche électroluminescente, améliorant la pureté colorimétrique et l'efficacité électroluminescente du matériau émettant de la lumière fluorescente, et un dispositif électroluminescent organique comprenant celui-ci.
PCT/KR2015/008687 2014-09-05 2015-08-20 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant le composé WO2016036031A1 (fr)

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KR10-2014-0119125 2014-09-05
KR1020140119125A KR20160029962A (ko) 2014-09-05 2014-09-05 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

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CN106146538A (zh) * 2016-06-30 2016-11-23 吉林奥来德光电材料股份有限公司 一种胺化合物及其制备方法和发光器件
CN107056806A (zh) * 2016-04-25 2017-08-18 中节能万润股份有限公司 一种含有均苯骨架结构的化合物及其在有机电致发光器件中的应用
CN107098918A (zh) * 2016-04-25 2017-08-29 中节能万润股份有限公司 一种以均苯为核心的光电材料及其应用
CN109665935A (zh) * 2017-10-16 2019-04-23 北京鼎材科技有限公司 一种新型化合物
WO2019076198A1 (fr) * 2017-10-16 2019-04-25 北京鼎材科技有限公司 Composé et dispositif électroluminescent organique
WO2019128875A1 (fr) * 2017-12-29 2019-07-04 广州华睿光电材料有限公司 Dérivé d'amine aromatique et dispositif électronique organique

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KR20240023290A (ko) * 2022-08-11 2024-02-21 솔루스첨단소재 주식회사 유기 전계 발광 소자 및 유기 화합물

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WO2011018951A1 (fr) * 2009-08-10 2011-02-17 Canon Kabushiki Kaisha Dérivé de pyrène et dispositif électroluminescent organique utilisant celui-ci
KR20120072320A (ko) * 2010-12-23 2012-07-03 에스에프씨 주식회사 피렌 유도체 화합물 및 이를 포함하는 유기전계발광소자
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107056806A (zh) * 2016-04-25 2017-08-18 中节能万润股份有限公司 一种含有均苯骨架结构的化合物及其在有机电致发光器件中的应用
CN107098918A (zh) * 2016-04-25 2017-08-29 中节能万润股份有限公司 一种以均苯为核心的光电材料及其应用
CN106146538A (zh) * 2016-06-30 2016-11-23 吉林奥来德光电材料股份有限公司 一种胺化合物及其制备方法和发光器件
CN109665935A (zh) * 2017-10-16 2019-04-23 北京鼎材科技有限公司 一种新型化合物
WO2019076198A1 (fr) * 2017-10-16 2019-04-25 北京鼎材科技有限公司 Composé et dispositif électroluminescent organique
WO2019128875A1 (fr) * 2017-12-29 2019-07-04 广州华睿光电材料有限公司 Dérivé d'amine aromatique et dispositif électronique organique

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