WO2007107306A1 - Verwendung von heterocyclischen radikalen zur dotierung von organischen halbeitern - Google Patents
Verwendung von heterocyclischen radikalen zur dotierung von organischen halbeitern Download PDFInfo
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- WO2007107306A1 WO2007107306A1 PCT/EP2007/002359 EP2007002359W WO2007107306A1 WO 2007107306 A1 WO2007107306 A1 WO 2007107306A1 EP 2007002359 W EP2007002359 W EP 2007002359W WO 2007107306 A1 WO2007107306 A1 WO 2007107306A1
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- H—ELECTRICITY
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- H10K99/00—Subject matter not provided for in other groups of this subclass
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/549—Organic PV cells
Definitions
- heterocyclic radical or diradical their dimers, oligomers, polymers, dispiro compounds and polycycles as dopant for doping an organic semiconducting matrix material
- the present invention relates to the use of heterocyclic radicals or radicals, their dimers, oligomers, polymers, dispiro compounds and polycycles for use as dopants for doping an organic semiconductive matrix material, as blocking layer, as charge injection layer, as electrode material, as memory material or as semiconductor material itself in electronic or optoelectronic components.
- Inorganic dopants such as alkali metals (eg cesium) or Lewis acids (eg FeCl 3 ) are usually disadvantageous in organic matrix materials because of their high diffusion coefficients, since the function and stability of the electronic components is impaired. Further, it is known to release dopants via chemical reactions in the semiconductive matrix material to provide dopants. However, the oxidation potential of the dopants released in this way is often insufficient for various applications, in particular for organic light-emitting diodes (OLEDs). Furthermore, upon release of the dopants, further compounds and / or atoms, for example atomic hydrogen, are generated, whereby the properties of the doped layer or of the corresponding electronic component are impaired.
- alkali metals eg cesium
- Lewis acids eg FeCl 3
- compounds used as dopants often do not have a sufficiently low ionization potential for the particular application.
- the present invention is based on the object by the use of certain heterocyclic radicals or diradicals, their dimers, oligomers, polymers, Dispirover- bonds and polycycles, improved organic semiconducting matrix materials, blocking layers, charge injection layers, electrode materials, memory materials or semiconductor layers themselves, especially in electronic or optoelectronic devices to provide.
- the radicals, diradicals and derivatives used should have sufficiently low oxidation potentials, without interfering with the matrix material and provide an effective increase in the number of charge carriers in the matrix material and be comparatively easy to handle.
- dimers is understood as meaning compounds which are formed by reaction of two monoradicals or diradicals with one another.
- oligomers is to be understood as meaning compounds which are composed of a plurality of diradicals, one first radical end of a diradical reacting with a first of a further diradical, and a second end of the thus newly formed, larger diradical reacting with a second The ends of such oligomers may be reacted by monoradicals.
- polymer is to be understood as meaning compounds which are built up from oligomers of a larger number of diradicals.
- a “dispiro compound” in accordance with the present invention is an intramolecular addition product of a diradical whose radical centers are spaced from structural elements of such a type that said structural element combines the formally radical-bearing, ie, inter-reactive, carbon atoms.
- polycycle is an intramolecular addition product of a diradical to understand whose radical centers are spaced from structural elements of such a type that said structural element other than the formally radical-bearing, ie mutually reactive carbon atoms connects (ie at least one at least alpha-stationary atom) ,
- the radicals R 1-9 and Ru may be preferably substituted aryl, wherein the substituents are preferably electron-donating radicals, for example dialkylamine Julolidyl, Diary- lamin, alkylarylamine, Diheterocyclylamin, Diheteroalkylamin, alkoxy, aryloxy, Alkylmer- captyl, Arylmercaptyl, alkyl, Sililyl , Haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, alkynyl, trialkylsililylalkynyl or styryl.
- substituents are preferably electron-donating radicals, for example dialkylamine Julolidyl, Diary- lamin, alkylarylamine, Diheterocyclylamin, Diheteroalkylamin, alkoxy, aryloxy, Alkylmer- captyl, Arylmercaptyl, alkyl, Sililyl ,
- hetero-cyclic compounds is a much stronger and / or more stable dopant than in previously known donor compounds, wherein the heterocyclic radicals and diradicals, their dimers, oligomers, dispiro compounds or polycycles in neutral form as an n-dopant be used against an organic semiconductive matrix material.
- the conductivity of charge transport layers in the case of use according to the invention is substantially increased and / or the transfer of the charge carriers between the contacts and the organic layer is substantially improved in applications as an electronic component.
- the cations belonging to the respective heterocyclic radicals and diradicals are formed, in particular by the transfer of at least one electron from the respective one heterocyclic radical and diradical, its dimer, OH gomer, dispiro compound or polycycle on the surrounding matrix material.
- anions of the matrix material are formed, which are movable on the matrix material. In this way, the matrix material acquires a conductivity that is opposite to the conductive increased speed of the undoped matrix material is increased.
- Conductivities of undoped matrix materials are generally ⁇ 10 '8 S / cm, in particular frequently ⁇ 10 10 S / cm.
- the conductivity of such matrix materials can for greater than 10 -8 S / cm, often increase> 10 "S / cm. This is especially true for matrix materials vs. a reduction potential of less than -1 V Fc / Fc +, preferably less than -1.7 V vs. Fc / Fc + , in particular less than -2.1 V vs. Fc / Fc +
- Fc / Fc + refers to the redox pair ferrocene / ferrocenium, which as reference in an electrochemical potential determination, for example Cyclo voltammetry is used.
- the described heterocyclic compounds can also be used as an injection layer in electronic components, preferably between an electrode and a semiconductor layer, which can also be doped, or as blocking layer, preferably between emitter and transport layer, or as semiconductor layer in electronic components can be.
- the use according to the invention enables a photo- or light-induced irreversible doping of organic semiconductors with the aid of the use according to the invention, in particular the generation of said radicals and diradicals by cleavage of their dimers or oligomers or dispirane compounds by means of electromagnetic radiation and a subsequent irreversible doping of n-type semiconductors.
- the heterocyclic compounds described are preferably isolated molecules which are thus preferably present in the respective semiconductive layer as isolated molecules which are not fixed by chemical bonds to one another and / or to a matrix or to another component.
- the dopants of the invention have a surprisingly high stability with respect to their reactivity with the atmosphere.
- radicals, diradicals and derivatives thereof can be synthesized by known methods, in some cases they are also commercially available. The synthesis of such compounds is described, for example, in the following references, which are hereby incorporated by reference in their entirety. as a reference in the application. It is understood that the cited references are given by way of example only.
- benzimidazoles can be readily prepared from o-phenylenediamine and corresponding carboxylic acid derivatives M.R. DeLuca, S.M. Kerwin Tetrahedron 51 457-64 (1997) or aldehydes (M. Curini et al., Synlett K) 1832-4 2004). See also MRGrimmett "Imidazoles and Benzimidazole Synthesis” Academic Press, Harcourt Brace & Company, Publishers, London, San Diego, New York, Boston O-phenylenediamines are commercially available or, for example, by the method of Sushitsky et al., JCSChem. Comm., 1977, 189-90 A representation of benzothiazoles can be prepared analogously via the o-mercaptoanilines.
- Perarylated imidazoles can be according to H.Baumgärtel et al. from benzoins, anilines and benzoic acid chloride (Ber Bunsenges (1972) 76/294-100; Chem. Ber. (1968) 101 3504).
- the alkylations of the or the N atom in the heterocyclic five-membered rings succeeds with dimethyl or diethyl sulfate in the presence of bases, H. Quast, E. Schmitt Chem. Ber. 101 4012-14 (1968) or with alkyl halides.
- the corresponding cationic products can be isolated as perchlorate, tetrafluoroborate, halide, tetraphenyl borate or hexafluorophosphate.
- the abovementioned radicals can be prepared chemically by means of alkali metals or the alkali metal amalgams or electrochemically from the corresponding heteroaromatic cations by reduction, T. Muramatsu et al. Chemistry Letters 1996 151-2; Pragst et al. J. Electroanal. Chem., 180 1984, 141-56; V. Wintgens, J.Pouliquen, J.Kossanyi, New J. Chem. 1986 10/6 345-50.
- the radicals rapidly dimerize or form dispiro compounds b and tricyclene d, T. Muramatsu, A. Toyota, M. Suzuki, J. Am. Chem. Soc.
- the position of the balance also depends on the length and type of bridge and thus the hoop stress, as well as the energetic state, in particular the temperature.
- Bis [3-methyl-2-alkyl-1,2-dihydro-benzothiazolyl (2)] and bis [3-methyl-2-aryl-1,2-dihydrobenzothiazolyl (2)] compounds can be directly represented by benzothiazolium salts and corresponding Grignard compounds, A.Kinya; S, Hiroaki; I. Naoki; Chem. Soc. Japan (1979) 52/1 156-9.
- Inter alia quinolinato complexes for example of aluminum or other main group metals, where the quinolinato ligand can also be substituted, can be used as n-dopable matrix materials.
- the matrix material may be tris (8-hydroxyquinolinato) aluminum.
- Other aluminum complexes containing O and / or N donor atoms may also be used if desired.
- BPhen bathophenanthroline tris (8-hydroxy-quinolinato) -aluminum C 1 -C 4 -diphenyl-i, i-O-phenanthroline)
- the quinolinato complexes may contain, for example, one, two or three quinolinato ligands, the other ligands preferably complexing with O and / or N donor atoms to the central atom, such as the above-mentioned AI complex.
- Phenanthrolines which may be substituted or unsubstituted, in particular aryl-substituted, for example phenyl- or naphthyl-substituted, can also be used as the matrix material.
- aryl-substituted for example phenyl- or naphthyl-substituted
- Bphen can be used as matrix material.
- Heteroaromatics in particular triazoles, may also be used as the matrix material, and if appropriate also pyrroles, imidazoles, triazoles, pyridines, pyrimidines, pyridazines and like.
- the heteroaromatics are preferably substituted, in particular aryl-substituted, for example phenyl or naphthyl-substituted.
- below triazole can be used as matrix material.
- the matrix material used consists entirely of a metal phthalocyanine complex, in particular ZnPc, a porphyrin complex, or a Buckminster fullerene, in particular fullerene C60.
- matrix materials mentioned can also be used with one another or mixed with other materials in the context of the invention. It is understood that suitable other organic matrix materials having semiconducting properties may also be used.
- the dopant is present in a doping concentration of ⁇ 1: 1 to the matrix molecule or the monomeric unit of a polymeric matrix molecule, preferably in a doping concentration of 1: 2 or less, more preferably from 1: 5 or less or 1: 10 or smaller ,
- the doping concentration may be in the range of 1: 1 to 1: 100,000, more preferably in the range of 1: 5 to 10,000 or 1: 10 to 1,000, for example in the range of 1:10 to 1: 100 or 1:25 to 1:50, without being limited thereto. Carrying out the doping
- the doping of the respective matrix material with the compounds to be used according to the invention can be carried out by one or a combination of the following processes:
- the doping can also be carried out in such a way that the dopant is evaporated out of a precursor compound which releases the dopant on heating and / or irradiation.
- a precursor compound which releases the dopant on heating and / or irradiation.
- a carbonyl compound, dinitrogen compound or the like can be used as the precursor compound, which releases CO, nitrogen or the like upon release of the dopant, although other suitable precursors can also be used, for example salts, for example halides, or the like.
- the selection of such precursor compound may be based on the fact that the dopant is not present in this compound as a radical. This can improve the handling of the dopant.
- the irradiation can be effected by means of electromagnetic radiation, in particular visible light, UV radiation.
- the irradiation can essentially provide the heat necessary for the evaporation, it can also be irradiated deliberately into specific bands of the compounds or precursors or compound complexes to be vaporized, such as charge-transfer complexes, in order to vaporize the compounds, for example by conversion into excited states to facilitate by dissociation of the complexes.
- the complex may also be sufficiently stable to evaporate undissociated under the given conditions or to be applied to the substrate. It is understood that other suitable methods for carrying out the doping can be used.
- the electron-rich radicals, diradicals and derivatives thereof used according to the invention it is possible to produce semiconducting layers which may be more linear in shape, such as e.g. as conductivity paths, contacts or the like.
- the compounds may hereby be used as n-dopants together with another compound which may function as matrix material, wherein the doping ratio may be 1: 1 or less.
- the dopant used may also be present in higher proportions to the other compound or component, however, so that the ratio dopant: compound can be in the ratio> 1: 1, for example in the ratio> 2: 1,> 5: 1, ⁇ 1O: 1 or> 20: 1 or higher.
- the respective other component may be one which can be used as matrix material in the case of the production of doped layers, without being limited thereto.
- the dopant used can also be present substantially in pure form, for example as a pure layer.
- the area containing a dopant or essentially or completely existing therefrom can in particular be provided with an organic semiconducting material and / or a inorganic semiconducting material be electrically conductively contacted, for example, be arranged on such a substrate.
- said electron-rich radicals, diradicals and derivatives are used according to the invention as n-dopants, for example in a ratio ⁇ 1: 1 or ⁇ 1: 2.
- C 60 can be used, for example when using fullerenes as matrix, semiconductive layers having conductivities at room temperature in the range of 10 ⁇ 5 S / cm or higher, for example 10 '3 S / cm or higher, for example 10 "1 S / cm.
- phthalocyanine-zinc As a matrix a conductivity of higher 10 "8 S / cm was achieved, for example 10 " 6 S / cm So far it was not possible to dope this matrix with organic donors, because the reduction potential of the matrix is too low In contrast, phthalocyanine zinc is at most 10 "10 S / cm.
- the layer or formation with the dopants may each contain one or more different such electron-rich radicals, diradicals and derivatives.
- n-doped organic semiconducting materials which can be arranged in particular in the form of layers or electrical conduction paths
- a multiplicity of electronic components or devices containing them can be produced with an n-doped organic semiconductor layer.
- electronic components also encompasses optoelectronic components
- the connections described allow the electronic properties of an electronically functionally effective region of the component, such as its electrical conductivity, light-emitting properties or the like, to be advantageously changed the conductivity of the doped layers is improved and / or the improvement of the charge carrier injection of contacts into the doped layer is achieved.
- the invention includes organic light emitting diodes (OLEDs), organic solar cells, field effect transistors, organic diodes, particularly those having a high rectification ratio such as 10 3 -10 7 , preferably 10 4 -10 7 or 10 5 -10 7 , and organic field effect transistors produced by the electron-rich radicals and their derivatives.
- OLEDs organic light emitting diodes
- organic solar cells organic solar cells
- field effect transistors organic diodes, particularly those having a high rectification ratio such as 10 3 -10 7 , preferably 10 4 -10 7 or 10 5 -10 7
- organic field effect transistors produced by the electron-rich radicals and their derivatives.
- an n-doped layer based on an organic matrix material may be present, for example, in the following layer structures, wherein preferably the base materials or matrix materials of the individual layers are respectively organic:
- M-i-n metal-insulator-n-doped semiconductor, wherein the layer M forms the metal ground contact and may be, for example, ITO, Au, Ag, Al, etc.
- the cover contact forms an ohmic contact with the n-doped layer and may consist of Al, for example.
- the layer "i" stands for an undoped layer.
- n-i-M the statements on the M-i-n structure apply, but in contrast to this, the ohmic contact is provided on the substrate.
- p-i-n p-doped semiconductor-insulator-n-doped semiconductor
- n-i-p n-doped semiconductor-insulator-p-doped semiconductor.
- i is an undoped layer
- p is a p-doped layer.
- the contact materials are here hole-etching, wherein on the p-side, for example, a layer or a contact of ITO or Au may be provided, or electron-injecting, n-side, a layer or a contact of ITO, Al or Ag can be provided.
- the i-layer may also be omitted, whereby layer sequences with pn or np junctions can be obtained.
- the use of the compounds described is not limited to the abovementioned embodiments, in particular the layer structures can be supplemented or modified by introducing additional suitable layers.
- OLEDs with such layer sequences, in particular with pin or with an inverse structure with them, can be constructed with the compounds described.
- organic diodes of the metal-insulator-n-doped semiconductor type (min) or optionally of the pin type, for example on the basis of phthalocyanine zinc can be produced with the aid of the described n-dopants. These diodes show a rectification ratio of 10 5 and higher.
- electronic components having pn junctions can be produced, with the same semiconductor material being used for the p-doped and n-doped sides (homo-pn junction), and wherein for the n-doped semiconductor material a described electron-rich radical or its derivative is used.
- the electron-rich radicals and derivatives can be used according to the invention in the electronic components but also in layers, conductivity paths, point contacts or the like, if these predominate over another component, for example as an injection layer in pure or substantially pure form.
- An extremely electron-rich radical or its oligomer, preferably dimer, and also diradicals or their dispiro compounds and tricyclic compounds are provided.
- the proposed radical, dimer, oligomer or dispiro compound and the tricycle are simultaneously vaporized with the matrix material.
- this is Matrix material in each case phthalocyanine zinc or fullerene C 60 .
- the n-dopant and matrix material can be evaporated in such a way that the layer deposited on a substrate in a vacuum evaporation plant has a doping ratio of n-dopant to matrix material of 1:10.
- Each doped with the n-dopant layer of the organic semiconductor material is applied to an ITO layer (indium tin oxide), which is arranged on a glass substrate.
- ITO layer indium tin oxide
- a metal cathode is deposited, for example, by vapor deposition of a suitable metal to produce an organic light emitting diode.
- the organic light-emitting diode can also have a so-called inverted layer structure, wherein the layer sequence is: glass substrate - metal cathode -n-doped organic layer - transparent conductive cover layer (for example ITO). It is understood that depending on the application, further layers can be provided between the individual layers mentioned.
- some devices were exposed to UV radiation, after which an irreversible increase in conductivity could be detected.
- halogen lamps or mercury pressure lamps can be used.
- the neutral dimer 1, r, 2,2 ', 4,4', 6,6'-octamethyl-4,4'-bis [1,4-dihydropyridinyl- (4)] was used to dope ZnPc as matrix material.
- Doped layers with a doping ratio dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant with ZnPc.
- the reduction potential of ZnPc is approx. -1.3V. Fc / Fc + .
- the fullerene C60 was doped with the l, 3-di- (4-anisyl) -2,4,5-triphenylimidazolyl radical in a ratio of 10: 1.
- the conductivity was 2x10 "5 S / cm
- the reduction potential of C60 is about -1.0V vs. Fc / Fc + .
- the neutral dimer 2,2 ', 4,4', 6,6'-hexamethyl-4,4'-bi-4H-pyran was prepared by conventional methods.
- the dimer was then filled with C60 as matrix material in an evaporator source.
- Doped layers with a doping ratio of dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant with C60.
- the conductivity was 3x10 "5 S / cm.
- the neutral dimer bis [l, 2,3-trimethyl-1,2-dihydrobenzimidazolyl (2)] was prepared by conventional methods.
- the dimer was then filled with ZnPc as matrix material in an evaporator source.
- Doped layers with a doping ratio of dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant with ZnPc.
- the neutral dimer bis [l, 2,3-trimethyl-1,2-dihydrobenzimidazolyl (2)] was prepared by conventional methods.
- the dimer was then filled with C60 as matrix material in an evaporator source.
- Doped layers with a doping ratio of dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant with C60.
- the conductivity was 2xlO ⁇ 3 S / cm.
- the neutral dimer bis- [1,2-dimethyl-1,2-dihydrobenzothiazolyl- (2)] was prepared by conventional procedures.
- the dimer was then filled with C60 as matrix material in an evaporator source.
- Doped layers with a doping ratio of dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant with C60.
- the conductivity was SxlO ⁇ S / cm.
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Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07723337A EP2002492B1 (de) | 2006-03-22 | 2007-03-16 | Verwendung von heterocyclischen radikalen zur dotierung von organischen halbeitern |
US12/293,757 US8431046B2 (en) | 2006-03-22 | 2007-03-16 | Use of heterocyclic radicals for doping organic semiconductors |
KR1020087025796A KR101460021B1 (ko) | 2006-03-22 | 2007-03-16 | 유기 반도체 매트릭스 물질을 도핑하기 위한 도펀트로서의 헤테로시클릭 라디칼 또는 헤테로시클릭 디라디칼, 이의 다이머, 올리고머, 폴리머, 디스피로 화합물 및 폴리사이클의 용도 |
JP2009500751A JP5356212B2 (ja) | 2006-03-22 | 2007-03-16 | 有機半導体のドーピングを目的とした複素環式ラジカルの使用 |
AT07723337T ATE540435T1 (de) | 2006-03-22 | 2007-03-16 | Verwendung von heterocyclischen radikalen zur dotierung von organischen halbeitern |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP06005834A EP1837927A1 (de) | 2006-03-22 | 2006-03-22 | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
EP06005834.4 | 2006-03-22 |
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PCT/EP2007/002359 WO2007107306A1 (de) | 2006-03-22 | 2007-03-16 | Verwendung von heterocyclischen radikalen zur dotierung von organischen halbeitern |
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US (1) | US8431046B2 (de) |
EP (2) | EP1837927A1 (de) |
JP (1) | JP5356212B2 (de) |
KR (1) | KR101460021B1 (de) |
AT (1) | ATE540435T1 (de) |
WO (1) | WO2007107306A1 (de) |
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EP2887416A1 (de) | 2013-12-23 | 2015-06-24 | Novaled GmbH | N-dotiertes Halbleitermaterial mit Phosphinoxidmatrix und Metalldotiermittel |
WO2015090504A2 (de) | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Heterocyclische spiroverbindungen |
EP2963010A1 (de) | 2014-07-04 | 2016-01-06 | Novaled GmbH | Elektronische Vorrichtung und Verbindung |
WO2016034262A1 (de) | 2014-09-05 | 2016-03-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2016155866A1 (en) | 2015-03-30 | 2016-10-06 | Merck Patent Gmbh | Formulation of an organic functional material comprising a siloxane solvent |
WO2016198141A1 (en) | 2015-06-12 | 2016-12-15 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for oled formulations |
EP3109916A1 (de) | 2015-06-23 | 2016-12-28 | Novaled GmbH | Organische lichtemittierende vorrichtung mit polarer matrix, metalldotierstoff und silber-kathode |
EP3109919A1 (de) | 2015-06-23 | 2016-12-28 | Novaled GmbH | N-dotiertes halbleitermaterial mit polarer matrix und einem metalldotiermittel |
EP3109915A1 (de) | 2015-06-23 | 2016-12-28 | Novaled GmbH | Organische lichtemittierende vorrichtung mit polarer matrix und metalldotiermittel |
WO2016207228A1 (en) | 2015-06-23 | 2016-12-29 | Novaled Gmbh | N-doped semiconducting material comprising polar matrix and metal dopant |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
WO2017097391A1 (en) | 2015-12-10 | 2017-06-15 | Merck Patent Gmbh | Formulations containing ketones comprising non-aromatic cycles |
WO2017102049A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a mixture of at least two different solvents |
WO2017102052A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a solid solvent |
WO2017102048A1 (en) | 2015-12-15 | 2017-06-22 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
WO2017140404A1 (en) | 2016-02-17 | 2017-08-24 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2017144516A1 (en) | 2016-02-22 | 2017-08-31 | Novaled Gmbh | Charge transporting semi-conducting material and electronic device comprising it |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2017216128A1 (en) | 2016-06-17 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018001928A1 (en) | 2016-06-28 | 2018-01-04 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018024719A1 (en) | 2016-08-04 | 2018-02-08 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3312895A1 (de) | 2016-10-24 | 2018-04-25 | Novaled GmbH | Organisches halbleitermaterial mit einem elektrischen n-dotierstoff sowie elektronentransportmatrix und elektronische vorrichtung mit dem halbleitermaterial |
EP3312896A1 (de) | 2016-10-24 | 2018-04-25 | Novaled GmbH | Organische elektrolumineszezvorrichtung mit einer redox-dotierten elektronentransportschicht und hilfselektronentransportschicht |
WO2018077660A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018077662A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018095839A1 (de) | 2016-11-22 | 2018-05-31 | Merck Patent Gmbh | Verbrückte triarylamine für elektronische vorrichtungen |
WO2018104202A1 (en) | 2016-12-06 | 2018-06-14 | Merck Patent Gmbh | Preparation process for an electronic device |
WO2018108760A1 (en) | 2016-12-13 | 2018-06-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
EP3355378A1 (de) | 2017-01-30 | 2018-08-01 | Novaled GmbH | Elektrolumineszente vorrichtung mit einer definierten schichtanordnung aus einer lichtemittierenden schicht, einer lochtransportschicht und einer elektronentransportschicht |
WO2018138319A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic electroluminescence (el) element |
WO2018138318A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
EP3369729A1 (de) | 2017-03-02 | 2018-09-05 | Novaled GmbH | Kondensierte 9-phenyl-acridin- derivate zur verwendung in einer elektronischen vorrichtung und anzeigevorrichtung |
WO2018178136A1 (en) | 2017-03-31 | 2018-10-04 | Merck Patent Gmbh | Printing method for an organic light emitting diode (oled) |
WO2018189050A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018189134A1 (de) | 2017-04-13 | 2018-10-18 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2018197447A1 (de) | 2017-04-25 | 2018-11-01 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2018202603A1 (en) | 2017-05-03 | 2018-11-08 | Merck Patent Gmbh | Formulation of an organic functional material |
DE102017111137A1 (de) | 2017-05-22 | 2018-11-22 | Novaled Gmbh | Organische elektrolumineszente Vorrichtung |
EP3406599A1 (de) | 2017-05-23 | 2018-11-28 | Novaled GmbH | Organische elektronische vorrichtung mit einer organischen halbleiterschicht |
EP3407401A1 (de) | 2017-05-23 | 2018-11-28 | Novaled GmbH | Organische elektronische vorrichtung mit einer organischen halbleiterschicht und bauelement |
EP3406752A1 (de) | 2017-05-22 | 2018-11-28 | Novaled GmbH | Verfahren zum erstellen einer elektronischen vorrichtung, auf diese art erhältliche elektronische vorrichtung und verbindungen zur verwendung hierbei |
WO2019002198A1 (en) | 2017-06-26 | 2019-01-03 | Merck Patent Gmbh | HOMOGENEOUS MIXTURES |
WO2019007866A1 (de) | 2017-07-05 | 2019-01-10 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2019007867A1 (de) | 2017-07-05 | 2019-01-10 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2019016184A1 (en) | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL |
CN109320528A (zh) * | 2018-10-27 | 2019-02-12 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
EP3470412A1 (de) | 2017-10-13 | 2019-04-17 | Novaled GmbH | Organische elektronische vorrichtung mit einer organischen halbleiterschicht |
EP3470398A1 (de) | 2017-10-13 | 2019-04-17 | Novaled GmbH | Organische elektronische vorrichtung mit einer organischen halbleiterschicht |
EP3483153A1 (de) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Verbindungen enthaltend triazin, fluoren und aryl gruppen und deren verwendung in organischen elektronischen vorrichtungen |
EP3483154A1 (de) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Verbindungen enthaltend triazin- , fluoren- und aryl-gruppen und deren verwendung in elektronischen organischen vorrichtungen |
WO2019096717A2 (de) | 2017-11-14 | 2019-05-23 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3524593A1 (de) | 2018-02-07 | 2019-08-14 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019162483A1 (en) | 2018-02-26 | 2019-08-29 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3533788A1 (de) | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
EP3582280A1 (de) | 2018-06-14 | 2019-12-18 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019238782A1 (en) | 2018-06-15 | 2019-12-19 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2020064582A1 (de) | 2018-09-24 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von granulat |
WO2020074379A1 (en) | 2018-10-12 | 2020-04-16 | Novaled Gmbh | Organic light emitting device |
WO2020094538A1 (en) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2020178230A1 (en) | 2019-03-04 | 2020-09-10 | Merck Patent Gmbh | Ligands for nano-sized materials |
EP3742513A1 (de) | 2019-05-21 | 2020-11-25 | Novaled GmbH | Organische leuchtdiode |
EP3840080A1 (de) | 2019-12-17 | 2021-06-23 | Novaled GmbH | Organische elektronische vorrichtung und anzeigevorrichtung mit der organischen elektronischen vorrichtung |
WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2021250279A1 (en) | 2020-06-12 | 2021-12-16 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2021250277A1 (en) | 2020-06-12 | 2021-12-16 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2021259824A1 (de) | 2020-06-23 | 2021-12-30 | Merck Patent Gmbh | Verfahren zur herstellung einer mischung |
WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
EP4037000A1 (de) | 2014-07-21 | 2022-08-03 | Merck Patent GmbH | Materialen für elektronische vorrichtungen |
WO2022223675A1 (en) | 2021-04-23 | 2022-10-27 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2022243403A1 (de) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
EP4141979A1 (de) | 2021-08-24 | 2023-03-01 | Novaled GmbH | Organische leuchtdiode und verbindung zur verwendung darin |
WO2023025843A1 (en) | 2021-08-24 | 2023-03-02 | Novaled Gmbh | Organic light emitting diode and a compound for use therein |
WO2023046950A1 (en) | 2021-09-27 | 2023-03-30 | Novaled Gmbh | Organic electronic device and a compound |
WO2023057327A1 (en) | 2021-10-05 | 2023-04-13 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
EP4177978A1 (de) | 2021-11-05 | 2023-05-10 | Novaled GmbH | Organische leuchtdiode, anzeigevorrichtung damit und beleuchtungsvorrichtung damit |
EP4198026A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Verbindungen zur verwendung in halbleitenden materialien für elektronische vorrichtungen |
EP4198103A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
EP4199133A1 (de) | 2021-12-20 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode, anzeigevorrichtung damit und verbindung |
EP4199125A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode, verfahren zu ihrer herstellung und vorrichtung damit |
EP4273947A1 (de) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
EP4273948A1 (de) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
EP4299573A1 (de) | 2022-06-30 | 2024-01-03 | Novaled GmbH | Verbindung, halbleitermaterial diese verbindung beinhaltend, organische elektronische vorrichtung mit dieser verbindung und verfahren diese vorrichtung herzustellen |
EP4321511A1 (de) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Verbindung, organisches halbleitendes material damit, organische elektronische vorrichtung damit sowie anzeigevorrichtung damit |
EP4346356A1 (de) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Halbleitermaterial, verfahren zur herstellung einer schicht des halbleitermaterials, organische halbleitervorrichtung mit dem halbleitermaterial und verbindung |
EP4346357A1 (de) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Halbleitermaterial, verfahren zur herstellung einer halbleiterschicht, organische halbleitervorrichtung mit dem organischen halbleitermaterial, anzeigevorrichtung mit dem organischen halbleiter |
Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101361710B1 (ko) * | 2006-03-21 | 2014-02-10 | 노발레드 아게 | 도핑된 유기 반도체 물질을 제조하는 방법 및 이러한 방법에 사용되는 포뮬레이션 |
EP1912268B1 (de) * | 2006-10-09 | 2020-01-01 | Novaled GmbH | Verfahren zur räumlichen Strukturierung der Leuchtdichte von lichtermittierenden organischen Halbleiterbauelementen, danach hergestelltes Halbleiterbauelement und Verwendung desselben |
DE102008011185A1 (de) | 2008-02-27 | 2009-09-03 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung einer dotierten organischen halbleitenden Schicht |
GB2467316B (en) | 2009-01-28 | 2014-04-09 | Pragmatic Printing Ltd | Electronic devices, circuits and their manufacture |
JP5492424B2 (ja) * | 2009-02-13 | 2014-05-14 | ケミプロ化成株式会社 | 有機ラジカル化合物、それを用いた有機デバイス |
DE102009013685B4 (de) | 2009-03-20 | 2013-01-31 | Novaled Ag | Verwendung einer organischen Diode als organische Zenerdiode und Verfahren zum Betreiben |
EP2433317B1 (de) * | 2009-05-19 | 2014-07-30 | heliatek GmbH | Halbleitendes bauelement |
GB2473200B (en) | 2009-09-02 | 2014-03-05 | Pragmatic Printing Ltd | Structures comprising planar electronic devices |
EP2489085A2 (de) | 2009-10-14 | 2012-08-22 | Novaled AG | Elektrooptisches, organisches halbleiterbauelement und verfahren zum herstellen desselben |
EP2312663B1 (de) | 2009-10-19 | 2014-10-15 | Novaled AG | Organische elektronische Vorrichtung mit einem organischen Halbleitermaterial |
DE102010004453A1 (de) | 2010-01-12 | 2011-07-14 | Novaled AG, 01307 | Organisches lichtemittierendes Bauelement |
EP2395571B1 (de) | 2010-06-10 | 2013-12-04 | Novaled AG | Eine organische Vorrichtung umfassend ein organisches halbleitendes Material |
KR102127406B1 (ko) | 2012-09-20 | 2020-06-29 | 유디씨 아일랜드 리미티드 | 전자 응용을 위한 아자디벤조푸란 |
CN105073763B (zh) | 2013-04-29 | 2019-03-01 | Udc 爱尔兰有限责任公司 | 具有碳烯配体的过渡金属配合物及其在oled中的用途 |
GB201309668D0 (en) | 2013-05-30 | 2013-07-17 | Isis Innovation | Organic semiconductor doping process |
EP3063153B1 (de) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophene für electronische anwendungen |
JP6107605B2 (ja) * | 2013-11-05 | 2017-04-05 | コニカミノルタ株式会社 | 有機エレクトロルミッセンス素子、及び照明装置 |
KR20230015524A (ko) | 2013-12-20 | 2023-01-31 | 유디씨 아일랜드 리미티드 | 매우 짧은 감쇠 시간을 갖는 고효율 oled 장치 |
EP3174885B1 (de) | 2014-07-28 | 2019-10-02 | Idemitsu Kosan Co., Ltd. | 2,9-funktionalisierte benzimidazolo[1,2-a]benzimidazole als wirte für organische lichtemittierende dioden (oleds) |
EP2982676B1 (de) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-b]benzoxazole für elektronische Anwendungen |
TWI690534B (zh) | 2014-08-08 | 2020-04-11 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 電致發光咪唑并喹噁啉碳烯金屬錯合物 |
EP2993215B1 (de) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazole für elektronische Anwendungen |
EP3015469B1 (de) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazole für elektronische Anwendungen |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
WO2016079169A1 (en) | 2014-11-18 | 2016-05-26 | Basf Se | Pt- or pd-carbene complexes for use in organic light emitting diodes |
EP3034506A1 (de) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-funktionalisierte Carbazolderivate für elektronische Anwendungen |
EP3034507A1 (de) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-funktionalisierte Dibenzofurane und Dibenzothiophene für organische Leuchtdioden (OLEDS) |
DE102015200699A1 (de) | 2015-01-19 | 2016-07-21 | Siemens Aktiengesellschaft | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
EP3054498B1 (de) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazozine |
EP3053918B1 (de) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-Carbazol substituierte Benzimidazole für Elektronische Anwendungen |
EP3061759B1 (de) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrilsubstituierte dibenzofurane |
EP3070144B1 (de) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Siebengliedrige ringverbindungen |
EP3072943B1 (de) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazol-substituierte benzonitrile |
EP3075737B1 (de) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazol mit aryl- oder heteroarylnitrilgruppen für organische leuchtdioden |
US20180182980A1 (en) | 2015-06-03 | 2018-06-28 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
DE102015210388A1 (de) * | 2015-06-05 | 2016-12-08 | Siemens Aktiengesellschaft | Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik |
US20180291028A1 (en) | 2015-10-01 | 2018-10-11 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150604B1 (de) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazol mit benzimidazolo[1,2-a]benzimidazolylgruppen, carbazolylgruppen, benzofurangruppen oder benzothiophengruppen für organische leuchtdioden |
WO2017056055A1 (en) | 2015-10-01 | 2017-04-06 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
EP3150606B1 (de) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles mit benzofuran-oder benzothiophen gruppen für organische licht emittierende dioden |
US20180319813A1 (en) | 2015-11-04 | 2018-11-08 | Idemitsu Kosan Co., Ltd | Benzimidazole fused heteroaryls |
US11174258B2 (en) | 2015-12-04 | 2021-11-16 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
US20180370981A1 (en) | 2015-12-21 | 2018-12-27 | Idemitsu Kosan Co., Ltd. | Hetero-condensed phenylquinazolines and their use in electronic devices |
KR20170074170A (ko) | 2015-12-21 | 2017-06-29 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도 |
JP6851725B2 (ja) | 2016-03-29 | 2021-03-31 | 住友化学株式会社 | 新規化合物及びその製造方法 |
JP6224758B2 (ja) | 2016-03-29 | 2017-11-01 | 住友化学株式会社 | 発光素子及びその製造方法 |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3312899B1 (de) | 2016-10-24 | 2021-04-07 | Novaled GmbH | Elektronentransportschichtstapel für eine organische lichtemittierende diode |
EP3418285B1 (de) | 2017-06-20 | 2020-05-06 | Idemitsu Kosan Co., Ltd. | Zusammensetzung mit einem substituierten ir-komplex und einem mit einem heteroatom verbrückten phenylchinazolin |
EP3466954A1 (de) | 2017-10-04 | 2019-04-10 | Idemitsu Kosan Co., Ltd. | Mit einem heteroatom verbrückte kondensierte phenylchinazoline |
KR102021436B1 (ko) * | 2018-01-22 | 2019-09-16 | 기초과학연구원 | 유기 발광 복합체 및 유기 발광 복합체의 제조 방법 |
CN117343078A (zh) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | 有机电致发光材料和器件 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5922396A (en) * | 1996-12-23 | 1999-07-13 | The University Of Southern California | Electron transporting and light emitting layers based on organic free radicals |
US20050061232A1 (en) * | 2003-08-18 | 2005-03-24 | Novaled Gmbh | Doped organic semiconductor materials and process for their preparation |
US20050072971A1 (en) | 2003-10-02 | 2005-04-07 | Marrocco Matthew L. | Organic diodes and materials |
Family Cites Families (77)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2566208A (en) * | 1948-10-13 | 1951-08-28 | Monsanto Chemicals | Dielectric composition of halogenated aromatic hydrocarbon and organic antimony compound as a corrosion inhibitor |
CH354065A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
CH354066A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
US3083242A (en) * | 1956-09-19 | 1963-03-26 | M & T Chemicals Inc | Preparation of certain organomagnesium chlorides in ethylene polyethers |
DE1140576B (de) * | 1961-09-21 | 1962-12-06 | Bayer Ag | Verfahren zur Herstellung von Arylmagnesiumhalogeniden |
US3563751A (en) * | 1967-07-20 | 1971-02-16 | Du Pont | Hexaarylbiimidazole-acridine dye compositions |
US3558671A (en) * | 1967-08-30 | 1971-01-26 | Du Pont | Fluoro- and cyano-substituted 7,7,8,8-tetracyanoquinodimethans and intermediates thereto |
US4003943A (en) * | 1974-12-20 | 1977-01-18 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
US4066569A (en) * | 1975-12-30 | 1978-01-03 | Hughes Aircraft Company | Dopants for dynamic scattering liquid crystals |
US4133821A (en) * | 1977-03-15 | 1979-01-09 | Wisconsin Alumni Research Foundation | Alkylidenediquinocyclopropanes and Diarylcyclopropenes and method for preparation |
JPS61254582A (ja) | 1985-05-04 | 1986-11-12 | Mitsubishi Chem Ind Ltd | テトラキス(1,3−ジチオ−ル−2−イリデン)〔4〕ラジアレン類 |
US4618453A (en) * | 1985-05-30 | 1986-10-21 | The United States Of America As Represented By The Secretary Of The Navy | Conductive heterocyclic ladder polymers |
JPS63172275A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
JPS63172274A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
US4960916A (en) * | 1989-09-29 | 1990-10-02 | United States Of America As Represented By The Secretary Of The Navy | Organometallic antimony compounds useful in chemical vapor deposition processes |
DE4024871A1 (de) * | 1990-08-06 | 1992-02-13 | Basf Ag | Perlfoermige antistatische expandierbare styrolpolymerisate |
US5093698A (en) * | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
DE4106122A1 (de) * | 1991-02-27 | 1992-09-03 | Bayer Ag | Neue naphthalimide, diese enthaltende toner und die verwendung der neuen naphthalimide als additive fuer toner |
JP2998268B2 (ja) * | 1991-04-19 | 2000-01-11 | 三菱化学株式会社 | 有機電界発光素子 |
JPH04338760A (ja) | 1991-05-15 | 1992-11-26 | Konica Corp | 電子写真感光体 |
US5393614A (en) * | 1992-04-03 | 1995-02-28 | Pioneer Electronic Corporation | Organic electroluminescence device |
EP0567429B1 (de) * | 1992-04-22 | 1996-01-10 | Ciba-Geigy Ag | Substituierte Tetracyanochinodimethane, Verfahren zu deren Herstellung und deren Verwendung als pi-akzeptoren und elektrische Halbleiter |
JPH07168377A (ja) | 1993-12-16 | 1995-07-04 | Konica Corp | 電子写真感光体 |
JP3256361B2 (ja) | 1993-12-29 | 2002-02-12 | 昭和電工株式会社 | ポリ(アルキル置換−2,5−ピリミジンジイル)及びその製造方法 |
FI95574C (fi) * | 1994-02-16 | 1996-02-26 | Valtion Teknillinen | Elektroneja johtavia molekyylivalmisteita |
EP0676461B1 (de) * | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
US6013982A (en) * | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
JPH10270171A (ja) * | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19756361A1 (de) * | 1997-12-18 | 1999-06-24 | Philips Patentverwaltung | Organische lichtemittierende Diode mit Terbiumkomplex |
JPH11251067A (ja) * | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19836408A1 (de) | 1998-08-12 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Grignardverbindungen |
JP3389888B2 (ja) | 1998-11-09 | 2003-03-24 | 東レ株式会社 | 発光素子 |
DE19858856A1 (de) * | 1998-12-19 | 2000-06-21 | Merck Patent Gmbh | Verfahren zur Herstellung von Arylmetallverbindungen und deren Umsetzung mit Elektrophilen |
US6103459A (en) * | 1999-03-09 | 2000-08-15 | Midwest Research Institute | Compounds for use as chemical vapor deposition precursors, thermochromic materials light-emitting diodes, and molecular charge-transfer salts and methods of making these compounds |
JP3924648B2 (ja) * | 1999-11-02 | 2007-06-06 | ソニー株式会社 | 有機電界発光素子 |
JP2001131174A (ja) * | 1999-11-02 | 2001-05-15 | Sony Corp | バソフェナントロリン化合物及びその製造方法 |
WO2001083410A1 (en) * | 2000-05-03 | 2001-11-08 | The Regents Of The University Of California | Soluble tetrahedral compounds for use in electroluminescent devices |
JP2001319698A (ja) | 2000-05-11 | 2001-11-16 | Fuji Photo Film Co Ltd | 光電変換素子および光電池 |
EP1160888A1 (de) * | 2000-05-29 | 2001-12-05 | Sony International (Europe) GmbH | Lochleitermaterial und Verwendung in einer (Farbstoff-)Solarzelle |
JP3998903B2 (ja) * | 2000-09-05 | 2007-10-31 | 出光興産株式会社 | 新規アリールアミン化合物及び有機エレクトロルミネッセンス素子 |
US6844089B2 (en) * | 2002-05-10 | 2005-01-18 | Sensient Imaging Technologies Gmbh | Organic red electro-luminescent device and dopant |
US6699597B2 (en) * | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
EP1289030A1 (de) * | 2001-09-04 | 2003-03-05 | Sony International (Europe) GmbH | Dotierung eines Lochleitermaterials |
JP3823312B2 (ja) * | 2001-10-18 | 2006-09-20 | 日本電気株式会社 | 有機薄膜トランジスタ |
KR100691543B1 (ko) * | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
DE10212926A1 (de) * | 2002-03-22 | 2003-10-16 | Infineon Technologies Ag | Halbleiterspeicherzelle und Halbleiterspeichereinrichtung |
WO2003088271A1 (en) | 2002-04-08 | 2003-10-23 | The University Of Southern California | Doped organic carrier transport materials |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
DE10224021B4 (de) * | 2002-05-24 | 2006-06-01 | Novaled Gmbh | Phosphoreszentes lichtemittierendes Bauelement mit organischen Schichten |
JP3960131B2 (ja) | 2002-06-05 | 2007-08-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、及びそれを用いた有機エレクトロルミネッセンス素子および表示装置 |
ES2197818B1 (es) | 2002-06-11 | 2005-02-01 | Institut Quimic De Sarria Cets | 2,7,12,17 alquenil, aril y heteroaril derivados del 3,6,13,16-tetraazaporficeno, y procedimiento, compuesto intermedio y utilizaciones correspondientes. |
US7074534B2 (en) * | 2002-07-10 | 2006-07-11 | E. I. Du Pont De Nemours And Company | Polymeric charge transport compositions and electronic devices made with such compositions |
DE10261662A1 (de) | 2002-12-20 | 2004-07-01 | Friedrich-Schiller-Universität Jena | Neue mit Pyrazinen verknüpfte 1,4,5,8-Tetraazafulvalene und Verfahren zu ihrer Herstellung |
US20050042390A1 (en) * | 2003-01-09 | 2005-02-24 | Siegel Stephen B. | Rotary UV curing method and apparatus |
DE102004014046B4 (de) * | 2003-03-19 | 2013-04-25 | Heliatek Gmbh | Photoaktives Bauelement mit organischen Schichten |
JP2004335557A (ja) | 2003-04-30 | 2004-11-25 | Ricoh Co Ltd | 縦型有機トランジスタ |
EP1477892B1 (de) * | 2003-05-16 | 2015-12-23 | Sap Se | System, Verfahren, Computerprogrammprodukt und Herstellungsartikel zur Dateneingabe in ein Computersystem |
US20050023974A1 (en) * | 2003-08-01 | 2005-02-03 | Universal Display Corporation | Protected organic electronic devices and methods for making the same |
DE10339772B4 (de) * | 2003-08-27 | 2006-07-13 | Novaled Gmbh | Licht emittierendes Bauelement und Verfahren zu seiner Herstellung |
DE10357044A1 (de) * | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
DE102004010954A1 (de) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
US7439537B2 (en) * | 2004-07-30 | 2008-10-21 | Agfa Graphics, N.V. | Divinylfluorenes |
US7540978B2 (en) * | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
EP1643568A1 (de) * | 2004-10-04 | 2006-04-05 | Novaled GmbH | Verfahren zum Herstellen einer Schicht aus einem dotierten Halbleitermaterial und Vorrichtung |
US8034466B2 (en) * | 2004-12-06 | 2011-10-11 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and light-emitting device using the same |
WO2006067800A1 (en) | 2004-12-24 | 2006-06-29 | Council Of Scientific And Industrial Research | Triorganoantimony compounds for pesticidal use |
JP5295756B2 (ja) * | 2005-04-14 | 2013-09-18 | メルク パテント ゲーエムベーハー | 有機電子素子のための化合物 |
US7563518B2 (en) * | 2005-07-28 | 2009-07-21 | Eastman Kodak Company | Low voltage organic electroluminescent element |
US7582893B2 (en) * | 2005-09-15 | 2009-09-01 | Spansion Llc | Semiconductor memory device comprising one or more injecting bilayer electrodes |
US20070116984A1 (en) * | 2005-09-21 | 2007-05-24 | Doosan Corporation | Spiro-compound for electroluminescent display device and electroluminescent display device comprising the same |
DE502005009802D1 (de) * | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
DE502006000749D1 (de) * | 2006-03-21 | 2008-06-19 | Novaled Ag | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
DE102006039423A1 (de) | 2006-08-23 | 2008-02-28 | Werner, Johannes | Halbleitende Polyaddukte mit kolumnarer Struktur |
DE602007008337D1 (de) * | 2006-10-24 | 2010-09-23 | Semiconductor Energy Lab | Anthrazenderivat und lichtemittierendes Element, lichtemittierende Vorrichtung und elektronische Vorrichtung mit Anthrazenderivat |
EP3457451B1 (de) * | 2007-04-30 | 2019-07-17 | Novaled GmbH | Die verwendung von oxokohlenstoff-, pseudooxokohlenstoff- und radialenverbindungen |
-
2006
- 2006-03-22 EP EP06005834A patent/EP1837927A1/de not_active Withdrawn
-
2007
- 2007-03-16 KR KR1020087025796A patent/KR101460021B1/ko active IP Right Grant
- 2007-03-16 US US12/293,757 patent/US8431046B2/en active Active
- 2007-03-16 JP JP2009500751A patent/JP5356212B2/ja active Active
- 2007-03-16 WO PCT/EP2007/002359 patent/WO2007107306A1/de active Application Filing
- 2007-03-16 AT AT07723337T patent/ATE540435T1/de active
- 2007-03-16 EP EP07723337A patent/EP2002492B1/de active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5922396A (en) * | 1996-12-23 | 1999-07-13 | The University Of Southern California | Electron transporting and light emitting layers based on organic free radicals |
US20050061232A1 (en) * | 2003-08-18 | 2005-03-24 | Novaled Gmbh | Doped organic semiconductor materials and process for their preparation |
US20050072971A1 (en) | 2003-10-02 | 2005-04-07 | Marrocco Matthew L. | Organic diodes and materials |
Non-Patent Citations (4)
Title |
---|
AUS T.P. VAID ET AL., CHEM. MATER., vol. 15, 2003, pages 4292 - 4299 |
T. MURAMATSU ET AL.: "Preparation and Properties of a Novel Heterocyclic Dispiro Compound, 3,10-Diaza-N,N-dimethyldispiro[5.0.5.3]pentadeca-1,4,8,11-tetraene", CHEMISTRY LETTERS, 1996, pages 151 - 152, XP008068093 * |
V. WINTGENS ET AL.: "REDUCTION OF PYRYLIUM SALTS: STUDY BY ESR AND UV-VISIBLE SPECTROSCOPY, OF THE REVERSIBLE DIMERIZATION OF THE PYRANLY RADICAL", NEW YOURNAL OF CHEMISTRY, vol. 10, no. 6, 1986, pages 345 - 350, XP008068094 * |
VAID T P ET AL: "Investigations of the 9,10-diphenylacridyl radical as an isostructural dopant for the molecular semiconductor 9,10-diphenylanthracene", CHEMISTRY OF MATERIALS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 15, no. 22, 7 October 2003 (2003-10-07), pages 4292 - 4299, XP002355671, ISSN: 0897-4756 * |
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WO2019072928A1 (en) | 2017-10-13 | 2019-04-18 | Novaled Gmbh | ORGANIC ELECTRONIC DEVICE COMPRISING AN ORGANIC SEMICONDUCTOR LAYER |
WO2019072932A1 (en) | 2017-10-13 | 2019-04-18 | Novaled Gmbh | ORGANIC ELECTRONIC DEVICE COMPRISING AN ORGANIC SEMICONDUCTOR LAYER |
EP3470412A1 (de) | 2017-10-13 | 2019-04-17 | Novaled GmbH | Organische elektronische vorrichtung mit einer organischen halbleiterschicht |
EP3483154A1 (de) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Verbindungen enthaltend triazin- , fluoren- und aryl-gruppen und deren verwendung in elektronischen organischen vorrichtungen |
EP3483153A1 (de) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Verbindungen enthaltend triazin, fluoren und aryl gruppen und deren verwendung in organischen elektronischen vorrichtungen |
WO2019096717A2 (de) | 2017-11-14 | 2019-05-23 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3524593A1 (de) | 2018-02-07 | 2019-08-14 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019154713A1 (en) | 2018-02-07 | 2019-08-15 | Novaled Gmbh | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
WO2019162483A1 (en) | 2018-02-26 | 2019-08-29 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2019166206A1 (en) | 2018-02-28 | 2019-09-06 | Novaled Gmbh | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
EP3533788A1 (de) | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2019238858A1 (en) | 2018-06-14 | 2019-12-19 | Novaled Gmbh | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
EP3582280A1 (de) | 2018-06-14 | 2019-12-18 | Novaled GmbH | Organisches material für eine elektronische optoelektronische vorrichtung und elektronische vorrichtung mit dem organischen material |
WO2019238782A1 (en) | 2018-06-15 | 2019-12-19 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2020064582A1 (de) | 2018-09-24 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von granulat |
WO2020074379A1 (en) | 2018-10-12 | 2020-04-16 | Novaled Gmbh | Organic light emitting device |
CN109320528B (zh) * | 2018-10-27 | 2021-04-13 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
CN109320528A (zh) * | 2018-10-27 | 2019-02-12 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
WO2020094538A1 (en) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2020178230A1 (en) | 2019-03-04 | 2020-09-10 | Merck Patent Gmbh | Ligands for nano-sized materials |
EP3742513A1 (de) | 2019-05-21 | 2020-11-25 | Novaled GmbH | Organische leuchtdiode |
WO2021122155A1 (en) | 2019-12-17 | 2021-06-24 | Novaled Gmbh | Organic electronic device and display device comprising the organic electronic device |
EP3840080A1 (de) | 2019-12-17 | 2021-06-23 | Novaled GmbH | Organische elektronische vorrichtung und anzeigevorrichtung mit der organischen elektronischen vorrichtung |
WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2021250277A1 (en) | 2020-06-12 | 2021-12-16 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2021250279A1 (en) | 2020-06-12 | 2021-12-16 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2021259824A1 (de) | 2020-06-23 | 2021-12-30 | Merck Patent Gmbh | Verfahren zur herstellung einer mischung |
WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
WO2022223675A1 (en) | 2021-04-23 | 2022-10-27 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2022243403A1 (de) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
WO2023025843A1 (en) | 2021-08-24 | 2023-03-02 | Novaled Gmbh | Organic light emitting diode and a compound for use therein |
EP4141979A1 (de) | 2021-08-24 | 2023-03-01 | Novaled GmbH | Organische leuchtdiode und verbindung zur verwendung darin |
WO2023046950A1 (en) | 2021-09-27 | 2023-03-30 | Novaled Gmbh | Organic electronic device and a compound |
WO2023057327A1 (en) | 2021-10-05 | 2023-04-13 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
EP4177978A1 (de) | 2021-11-05 | 2023-05-10 | Novaled GmbH | Organische leuchtdiode, anzeigevorrichtung damit und beleuchtungsvorrichtung damit |
EP4198026A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Verbindungen zur verwendung in halbleitenden materialien für elektronische vorrichtungen |
EP4198103A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
EP4199125A1 (de) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode, verfahren zu ihrer herstellung und vorrichtung damit |
WO2023110608A1 (en) | 2021-12-14 | 2023-06-22 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2023110610A1 (en) | 2021-12-14 | 2023-06-22 | Novaled Gmbh | Organic light emitting diode, method for preparing the same and device comprising the same |
EP4199133A1 (de) | 2021-12-20 | 2023-06-21 | Novaled GmbH | Organische leuchtdiode, anzeigevorrichtung damit und verbindung |
WO2023117255A1 (en) | 2021-12-20 | 2023-06-29 | Novaled Gmbh | Organic light emitting diode, display comprising the same, and compound |
EP4273947A1 (de) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
EP4273948A1 (de) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organische leuchtdiode und vorrichtung damit |
WO2023213705A1 (en) | 2022-05-02 | 2023-11-09 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
WO2023213712A1 (en) | 2022-05-02 | 2023-11-09 | Novaled Gmbh | Organic light emitting diode and device comprising the same |
EP4299573A1 (de) | 2022-06-30 | 2024-01-03 | Novaled GmbH | Verbindung, halbleitermaterial diese verbindung beinhaltend, organische elektronische vorrichtung mit dieser verbindung und verfahren diese vorrichtung herzustellen |
WO2024002883A1 (en) | 2022-06-30 | 2024-01-04 | Novaled Gmbh | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and a method for preparing the organic electronic device |
EP4321511A1 (de) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Verbindung, organisches halbleitendes material damit, organische elektronische vorrichtung damit sowie anzeigevorrichtung damit |
WO2024033353A1 (en) | 2022-08-09 | 2024-02-15 | Novaled Gmbh | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and display device comprising the same |
EP4346356A1 (de) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Halbleitermaterial, verfahren zur herstellung einer schicht des halbleitermaterials, organische halbleitervorrichtung mit dem halbleitermaterial und verbindung |
EP4346357A1 (de) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Halbleitermaterial, verfahren zur herstellung einer halbleiterschicht, organische halbleitervorrichtung mit dem organischen halbleitermaterial, anzeigevorrichtung mit dem organischen halbleiter |
WO2024068951A1 (en) | 2022-09-29 | 2024-04-04 | Novaled Gmbh | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the semiconducting material and compound |
WO2024068954A1 (en) | 2022-09-29 | 2024-04-04 | Novaled Gmbh | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the organic semiconducting material, display device comprising the organic semiconducting device and compound |
Also Published As
Publication number | Publication date |
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EP2002492B1 (de) | 2012-01-04 |
US20110108772A1 (en) | 2011-05-12 |
JP5356212B2 (ja) | 2013-12-04 |
JP2009530835A (ja) | 2009-08-27 |
ATE540435T1 (de) | 2012-01-15 |
KR20090006111A (ko) | 2009-01-14 |
US8431046B2 (en) | 2013-04-30 |
EP2002492A1 (de) | 2008-12-17 |
KR101460021B1 (ko) | 2014-11-11 |
EP1837927A1 (de) | 2007-09-26 |
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