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WO2014200243A1 - 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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WO2014200243A1
WO2014200243A1 PCT/KR2014/005078 KR2014005078W WO2014200243A1 WO 2014200243 A1 WO2014200243 A1 WO 2014200243A1 KR 2014005078 W KR2014005078 W KR 2014005078W WO 2014200243 A1 WO2014200243 A1 WO 2014200243A1
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organic
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Yu-Mi Chang
Song Lee
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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SK Chemicals Co Ltd
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Priority claimed from KR20140060059A external-priority patent/KR20140145540A/ko
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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 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.
  • 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. Especially if the fluorescent light emitting materials are used, the fluorescent host materials are needed to satisfy both high efficiency and high colorimetric purity.
  • an object of the present invention is to provide a compound for an organic EL device which may be used as a host of a fluorescent light emitting layer with high electrical stability, high transport capacity of an electron and a hole, high efficiency, and high colorimetric purity and an organic electroluminescent device including the same.
  • Another object of the present invention is to provide a compound for an organic EL device which may be used as an electron or a hole transport material and an organic electroluminescent device including the same.
  • 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 5 , and R 7 to R 11 are identical to or different from each other, and R 1 to R 5 , and R 7 to R 11 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 1 to R 5 , and R 7 to R 11 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 heterocyclo
  • R 6 to R 12 are identical to or different from each other, and R 6 to R 12 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.
  • R 1 to R 12 are identical to or different from each other, and R 1 to R 12 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 a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
  • X 1 is an oxygen atom, a sulfur atom, , , or ,
  • Ar 1 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 35 to R 38 are identical to or different from each other, and R 35 to R 38 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 R 35 and R 36 , and R 37 and R 38 , respectively, are linked to form 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 13 to R 34 are identical to or different from each other, and R 13 to R 34 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 13 to R 34 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 1 to R 12 are identical to or different from each other, and R 1 to R 12 are each independently a hydrogen atom, a deuterium atom, , , , , , ,
  • X 1 is a oxygen atom, a sulfur atom, , ,
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • R 35 to R 38 are identical to or different from each other, and R 35 to R 38 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, and
  • R 13 to R 34 are identical to or different from each other, and R 13 to R 34 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 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 1 to 65 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 may provide a compound for an organic EL device which may be used as a host of a fluorescent light emitting layer with high electrical stability, high transport capacity of an electron and a hole, high efficiency and high colorimetric purity, and an organic electroluminescent device including the same.
  • the present invention may also provide a compound for an organic EL device which may be used as an electron transport material or a hole transport material, and an organic electroluminescent device including the same.
  • 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 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 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 40 nm.
  • NPB N,N’-bis(1-naphthyl)-N,N’-diphenyl-1,1’-biphenyl-4,4’-diamine
  • DPP N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine
  • an electron transport layer was formed to a thickness of 25 nm deposing Alq 3 on the light emitting layer, and 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.
  • deposition speed of materials was 0.1nm/sec of organic compound 1, DNTPD, NPB and Alq 3 , 0.01 nm/sec of lithium fluoride and 0.5nm/sec of alluminium.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 2 was used instead of Compound 1 in Device Example 2.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 3 was used instead of Compound 1 in Device Example 3.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 4 was used instead of Compound 1 in Device Example 4.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 5 was used instead of Compound 1 in Device Example 5.
  • An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 6 was used instead of Compound 1 in Device Example 6.
  • 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).
  • the present invention may provide a compound for an organic EL device which may be used as a host of a fluorescent light emitting layer with high electrical stability, high transport capacity of an electron and a hole, high efficiency and high colorimetric purity, and an organic electroluminescent device including the same.
  • the present invention may also provide a compound for an organic EL device which may be used as an electron transport material or a hole transport material, and an organic electroluminescent device including the same.

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

Abstract

L'invention concerne un composé pour dispositif électroluminescent organique et un dispositif électroluminescent organique comprenant le composé. L'invention concerne un composé pour dispositif électroluminescent organique pouvant être utilisé en tant qu'hôte d'une couche électroluminescente fluorescente à haute stabilité électrique, haute capacité de transport d'électron et de trou, grande efficacité et pureté, et en tant que matériau de transport d'électron ou de trou.
PCT/KR2014/005078 2013-06-12 2014-06-10 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant le composé Ceased WO2014200243A1 (fr)

Applications Claiming Priority (4)

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KR20130067043 2013-06-12
KR10-2013-0067043 2013-06-12
KR10-2014-0060059 2014-05-20
KR20140060059A KR20140145540A (ko) 2013-06-12 2014-05-20 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016133058A1 (fr) * 2015-02-18 2016-08-25 Tdk株式会社 Élément électroluminescent
CN107162869A (zh) * 2017-05-05 2017-09-15 吉林奥来德光电材料股份有限公司 芘类衍生物有机电致发光材料及其制备方法和有机电致发光器件

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Publication number Priority date Publication date Assignee Title
KR20040034349A (ko) * 2002-10-16 2004-04-28 내셔널 칭화 유니버시티 방향족 화합물 및 유기 발광 다이오드
WO2007004364A1 (fr) * 2005-07-06 2007-01-11 Idemitsu Kosan Co., Ltd. Dérivé du pyrène et dispositif électroluminescent organique l’utilisant
JP2009070987A (ja) * 2007-09-12 2009-04-02 Mitsui Chemicals Inc 有機トランジスタ
WO2011030493A1 (fr) * 2009-09-14 2011-03-17 Canon Kabushiki Kaisha Nouveau composé de pyrène et dispositif organique électroluminescent comprenant ledit composé
WO2011077691A1 (fr) * 2009-12-21 2011-06-30 出光興産株式会社 Element electroluminescent organique utilisant un derive de pyrene

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Publication number Priority date Publication date Assignee Title
KR20040034349A (ko) * 2002-10-16 2004-04-28 내셔널 칭화 유니버시티 방향족 화합물 및 유기 발광 다이오드
WO2007004364A1 (fr) * 2005-07-06 2007-01-11 Idemitsu Kosan Co., Ltd. Dérivé du pyrène et dispositif électroluminescent organique l’utilisant
JP2009070987A (ja) * 2007-09-12 2009-04-02 Mitsui Chemicals Inc 有機トランジスタ
WO2011030493A1 (fr) * 2009-09-14 2011-03-17 Canon Kabushiki Kaisha Nouveau composé de pyrène et dispositif organique électroluminescent comprenant ledit composé
WO2011077691A1 (fr) * 2009-12-21 2011-06-30 出光興産株式会社 Element electroluminescent organique utilisant un derive de pyrene

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016133058A1 (fr) * 2015-02-18 2016-08-25 Tdk株式会社 Élément électroluminescent
JPWO2016133058A1 (ja) * 2015-02-18 2017-11-30 Tdk株式会社 電界発光素子
CN107162869A (zh) * 2017-05-05 2017-09-15 吉林奥来德光电材料股份有限公司 芘类衍生物有机电致发光材料及其制备方法和有机电致发光器件

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