US20120205645A1 - Heteroleptic carbene complexes and the use thereof in organic electronics - Google Patents

Heteroleptic carbene complexes and the use thereof in organic electronics Download PDF

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US20120205645A1
US20120205645A1 US13/504,725 US201013504725A US2012205645A1 US 20120205645 A1 US20120205645 A1 US 20120205645A1 US 201013504725 A US201013504725 A US 201013504725A US 2012205645 A1 US2012205645 A1 US 2012205645A1
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carbon atoms
substituted
heteroatoms
radical
optionally
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Evelyn Fuchs
Oliver Molt
Korinna Dormann
Thomas Gessner
Nicolle Langer
Ingo Muenster
Jianqiang Qu
Christian Lennartz
Christian Schildknecht
Soichi Watanabe
Gerhard Wagenblast
Guenter Schmid
Herbert Friedrich Boerner
Volker Van Elsbergen
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BASF SE
Osram Oled GmbH
OLEDworks GmbH
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BASF SE
Osram Opto Semiconductors GmbH
Koninklijke Philips Electronics NV
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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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to heteroleptic complexes comprising a phenylimidazole or phenyltriazole unit bonded via a carbene bond to a central metal atom, and phenylimidazole ligands attached via a nitrogen-metal bond to the central atom, to OLEDs which comprise such heteroleptic complexes, to light-emitting layers comprising at least one such heteroleptic complex, to a device selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a heteroleptic complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge blocker.
  • OLEDs Organic Light-Emitting Diodes
  • OLEDs exploit the property of materials to emit light when they are excited by electrical current.
  • OLEDs are of particular interest as an alternative to cathode ray tubes and liquid-crystal displays for production of flat visual display units.
  • devices comprising OLEDs are suitable especially for mobile applications, for example for applications in cellphones, laptops, etc.
  • white OLEDs give great advantages over the illumination technologies known to date, especially a particularly high efficiency.
  • the prior art proposes numerous materials, examples of which include heteroleptic complexes with iridium as the central metal atom, which emit light on excitation by electrical current.
  • WO 2006/121811 A1 discloses phosphorescent heteroleptic metal complexes which comprise carbene ligands.
  • Compounds which have imidazolocarbenes (imidazolylidenes) or triazolocarbenes (triazolylidenes) as ligands are not disclosed in WO 2006/121811 A1.
  • WO 2006/067074 A1 likewise discloses electroluminescent heteroleptic metal complexes with carbene ligands.
  • the noncarbene ligands used include arylpyridines, arylpyrazoles and aryltriazoles.
  • Use of 2-phenyl-1H-imidazoles as noncarbene ligands is not disclosed in WO 2006/067074 A1.
  • WO 2007/115981 discloses heteroleptic metal complexes comprising both carbene ligands and heterocyclic noncarbene ligands, a process for preparation thereof, and the use of these compounds in OLEDs.
  • the compounds disclosed by way of example in WO 2007/115981 do not comprise a combination of 2-phenyl-1H-imidazole ligands with an imidazolocarbene (imidazolylidene) ligand or a triazolocarbene (triazolylidene) ligand.
  • JP 2009057505 discloses optoelectronic components which comprise compounds with tunable emission wavelength, high light emission efficiency and long lifetime.
  • the components according to this document comprise metal complexes which, as well as two ligands optionally joined to one another, comprise at least one ligand attached to the metal atom firstly via a carbene bond and secondly via a noncarbene bond.
  • No combination of a 2-phenyl-1H-imidazole ligand with an imidazolocarbene (imidazolylidene) ligand or a triazolocarbene (triazolylidene) ligand is disclosed.
  • electroluminescence is understood to mean both electrofluorescence and electrophosphorescence.
  • M in which M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each defined as follows:
  • aryl radical, unit or group, heteroaryl radical, unit or group, alkyl radical, unit or group and cycloalkyl radical, unit or group are each defined as follows, as long as no different meanings are mentioned:
  • An aryl radical or group is understood to mean a radical with a base skeleton of 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, which is formed from an aromatic ring or a plurality of fused aromatic rings.
  • Suitable base skeletons are, for example, phenyl, benzyl, naphthyl, anthracenyl or phenanthrenyl. This base skeleton may be unsubstituted, which means that all carbon atoms which are substitutable bear hydrogen atoms, or may be substituted at one, more than one or all substitutable positions of the base skeleton.
  • Suitable substituents are, for example, alkyl radicals, preferably alkyl radicals having 1 to 8 carbon atoms, more preferably methyl, ethyl, i-propyl or t-butyl, aryl radicals, preferably C 6 -aryl radicals, which may in turn be substituted or unsubstituted, heteroaryl radicals, preferably heteroaryl radicals which comprise at least one nitrogen atom, more preferably pyridyl radicals, alkenyl radicals, preferably alkenyl radicals which bear one double bond, more preferably alkenyl radicals with one double bond and 1 to 8 carbon atoms, or groups with donor or acceptor action.
  • Groups with donor action are understood to mean groups which have a +I and/or +M effect
  • groups with acceptor action are understood to mean groups which have a ⁇ I and/or ⁇ M effect.
  • Suitable groups with donor or acceptor action are halogen radicals, preferably F, Cl, Br, more preferably F, alkyl radicals, alkoxy radicals, aryloxy radicals, carbonyl radicals, ester radicals, amine radicals, amide radicals, CH 2 F groups, CHF 2 groups, CF 3 groups, CN groups, thio groups or SCN groups.
  • the aryl radicals most preferably bear substituents selected from the group consisting of methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, aryloxy, amine, thio groups and alkoxy, or the aryl radicals are unsubstituted.
  • the aryl radical or the aryl group is preferably a C 6 -aryl radical optionally substituted by at least one of the aforementioned substituents.
  • the C 6 -aryl radical more preferably has none, one, two or three of the aforementioned substituents.
  • a heteroaryl radical or a heteroaryl group is understood to mean radicals having 5 to 30 carbon atoms and/or heteroatoms, which differ from the aforementioned aryl radicals in that at least one carbon atom in the base skeleton of the aryl radicals is replaced by a heteroatom.
  • Preferred heteroatoms are N, O and S.
  • one or two carbon atoms of the base skeleton of the aryl radicals are replaced by heteroatoms.
  • the base skeleton is especially preferably selected from electron-poor systems such as pyridyl, pyrimidyl, pyrazyl and triazolyl, and five-membered heteroaromatics such as pyrrole, furan, thiophene, imidazole, pyrazole, triazole, oxazole and thiazole.
  • the base skeleton may be substituted at one, more than one or all substitutable positions of the base skeleton. Suitable substituents are the same as have already been specified above for the aryl groups.
  • alkyl radical or an alkyl group is understood to mean a radical having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms.
  • This alkyl radical may be branched or unbranched and may optionally be interrupted by one or more heteroatoms, preferably N, O or S.
  • this alkyl radical may be substituted by one or more of the substituents already specified for the aryl groups. It is likewise possible that the alkyl radical bears one or more aryl groups. All of the aryl groups listed above are suitable.
  • alkyl radicals selected from the group consisting of methyl, ethyl, i-propyl, n-propyl, i-butyl, n-butyl, t-butyl, sec-butyl, i-pentyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, i-hexyl and sec-hexyl.
  • alkyl radicals selected from the group consisting of methyl, ethyl, i-propyl, n-propyl, i-butyl, n-butyl, t-butyl, sec-butyl, i-pentyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, i-hexyl and sec-hexyl.
  • methyl, i-propyl, tert-butyl
  • a cycloalkyl radical or a cycloalkyl group is understood to mean a cyclic radical having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms.
  • This cycloalkyl radical may optionally be interrupted by one or more heteroatoms, preferably N, O or S.
  • this cycloalkyl radical may be unsubstituted or substituted, i.e. may be substituted by one or more of the substituents already specified for the aryl groups. It is likewise possible that the cycloalkyl radical bears one or more aryl groups. All of the aryl groups listed above are suitable.
  • aryl, heteroaryl, alkyl and cycloalkyl radicals applies, in accordance with the invention, independently to the radicals mentioned in the present application, especially to the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 radicals, where R 8 and R 9 , in the case that A 1 and/or A 2 is N, are a free electron pair, which means that no substituent selected from the abovementioned group is present on these ring nitrogen atoms. In the case that A 1 and/or A 2 is C, R 8 and R 9 are each independently hydrogen and/or the substituents specified.
  • M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each defined as follows:
  • M is Ir or Pt, preferably Ir.
  • Ir is present in the inventive heteroleptic complexes in the +3 oxidation state.
  • Pt is present in the inventive heteroleptic complexes in the +2 oxidation state.
  • a 1 and A 2 are each independently C or N. Preference is given in accordance with the invention to the following embodiments:
  • R 1 is a linear or branched alkyl radical having 1 to 20 carbon atoms, a substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl radical having 5 to 18 carbon atoms and/or heteroatoms.
  • R 1 is more preferably a substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, most preferably a substituted, especially ortho,ortho′- or ortho,ortho′,para-substituted, or unsubstituted phenyl radical.
  • the substituents are preferably alkyl radicals having 1 to 10, especially 1 to 6, carbon atoms, for example methyl, ethyl, propyl, butyl.
  • Very particularly preferred R 1 radicals are phenyl, 2,6-dimethylphenyl, 2,6-di-iso-propylphenyl or 2,4,6-trimethylphenyl, i.e. mesityl.
  • the present invention therefore relates more particularly to an inventive heteroleptic complex where R 1 is an aryl radical which has 6 to 30 carbon atoms and is substituted in the ortho,ortho′ positions in each case by a linear or branched alkyl radical having 1 to 10 carbon atoms.
  • R 2 , R 3 are each independently hydrogen, a linear or branched alkyl radical having 1 to 20 carbon atoms, a substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl radical having 5 to 18 carbon atoms and/or heteroatoms.
  • R 4 , R 5 , R 6 , R 7 are each hydrogen or R 4 and R 5 or R 5 and R 6 or R 6 and R 7 , especially R 5 and R 6 or R 6 and R 7 , together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 6 to 30 carbon atoms.
  • R 4 and R 5 or R 5 and R 6 or R 6 and R 7 together form a cycle of the general formula (IIa) or (IIb)
  • R 8 , R 9 are each independently a free electron pair if A 1 or A 2 is N, or, if A 1 or A 2 is C, hydrogen or linear or branched alkyl radical having 1 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl radical having 5 to 18 carbon atoms and/or heteroatoms, most preferably phenyl radical.
  • R 10 is a linear or branched alkyl radical having 1 to 20 carbon atoms, more preferably having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, more preferably having 6 to 10 carbon atoms.
  • particularly preferred alkyl radicals for R 10 are methyl, ethyl, propyl, especially isopropyl, butyl, especially tert-butyl, or pentyl.
  • aryl radicals for R 10 are unsubstituted phenyl or substituted phenyl, preferably substituted in the ortho position, for example by alkyl radicals having 1 to 6 carbon atoms, for example methyl, ethyl or propyl, especially isopropyl.
  • R 11 , R 12 , R 13 , R 14 are each independently hydrogen or a linear or branched alkyl radical having 1 to 20 carbon atoms, more preferably hydrogen.
  • R 1 and R 14 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms, preferably a six-membered aromatic ring, is optionally fused.
  • R 1 and R 14 form an unsaturated bridge having two carbon atoms, to which a six-membered aromatic ring is fused, which is either unsubstituted or substituted by one or two alkyl radicals having 1 to 6 carbon atoms, for example methyl or ethyl.
  • R 7 and R 8 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms, preferably a six-membered aromatic ring, is optionally fused.
  • R 7 and R 8 form an unsaturated bridge having two carbon atoms, to which a six-membered aromatic ring is fused, which is either unsubstituted or substituted by one or two alkyl radicals having 1 to 6 carbon atoms, for example methyl or ethyl.
  • the present invention more preferably relates to inventive heteroleptic complexes of the general formula (I) where M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each defined as follows:
  • the present invention preferably further relates to inventive heteroleptic complexes of the general formula (I) where M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each defined as follows:
  • the present invention preferably also relates to inventive heteroleptic complexes of the general formula (I) where M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each defined as follows:
  • Very particularly preferred inventive heteroleptic complexes of the general formula (I) have the ligands depicted in table 1, especially preferably in the combinations shown:
  • heteroleptic complexes of the general formula (I) Depending on the coordination number of the metal M present in the inventive heteroleptic complexes of the general formula (I) and the number of carbene ligands and noncarbene ligands used, different isomers of the corresponding heteroleptic metal complexes may be present with the same metal M and the same nature of the carbene ligands and noncarbene ligands used.
  • the S1a/S1b and S2a/S2b isomers are referred to as pseudo-meridional isomers and the S3a/S3b and S4a/S4b isomers as pseudo-facial isomers.
  • the S3 and S4 isomers when used in OLEDs, give particularly good results with regard to efficiency and lifetime when used in diodes.
  • the S3a/S3b and S4a/S4b isomers, i.e. the pseudo-facial isomers, are therefore particularly preferred in accordance with the invention.
  • inventive complexes of the general formula (I) which comprise two noncarbene ligands and one carbene ligand are present as pseudo-facial isomers.
  • the T1a/T1b and T2a/T2b isomers are referred to as pseudo-meridional isomers and the T3a/T3b and T4a/T4b isomers as pseudo-facial isomers.
  • the T3 and T4 isomers when used in OLEDs, usually give particularly good results with regard to efficiency and lifetime when used in diodes.
  • the T3a/T3b and T4a/T4b isomers i.e. the pseudo-facial isomers, are therefore particularly preferred in accordance with the invention.
  • the inventive complexes of the general formula (I) which comprise one noncarbene ligand and two carbene ligands are present as pseudo-facial isomers.
  • the different isomers of the heteroleptic metal complexes of the formula (I) can be separated by processes known to those skilled in the art, for example by chromatography, sublimation or crystallization.
  • the different isomers can generally be interconverted by suitable reaction conditions (e.g. pH), thermally or photochemically.
  • the present invention relates both to the individual isomers or enantiomers of the heteroleptic complexes of the formula (I) and to mixtures of different isomers or enantiomers in any desired mixing ratio.
  • the present invention therefore relates, in a particularly preferred embodiment, to the inventive heteroleptic complexes with the general and preferred definitions specified for M, A 1 , A 2 , n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 , where these have one of the following configurations IIIa, IIIb, IVa or IVb:
  • the present invention additionally also relates to a process for preparing an inventive heteroleptic complex of the general formula (I) by
  • a complex comprising appropriate noncarbene ligands, attached to the appropriate metal M, preferably iridium, and appropriate carbene ligands, preferably in deprotonated form as the free carbene or in the form of a protected carbene, for example as the silver-carbene complex, are contacted.
  • suitable precursor compounds comprise the appropriate substituents R 1 to R 14 which are to be present in the complexes of the general formula (I).
  • these complexes used as precursor compounds may comprise further ligands known to those skilled in the art, for example halides, preferably chloride.
  • Further suitable ligands are, for example 1,5-cyclooctadiene (COD), phosphines, cyanides, alkoxides, pseudohalides and/or alkyl.
  • R 1 , R 2 , R 3 , R 11 , R 12 , R 13 and R 14 where Y may independently be F, Cl, Br, I, methoxy or carboxylate.
  • Particularly preferred precursor compounds for the carbene ligands used in complexes of the general formula (I) correspond, for example, to the general formulae (VII) or (VIII)
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and A where Z may be F, Cl, Br, I, BF 4 , PF 6 , ClO 4 or SbF 6 .
  • the carbene ligand precursors are deprotonated, preferably before the reaction, for example, by basic compounds known to those skilled in the art, for example basic metalates, basic metal acetates, acetylacetonates or alkoxides, or bases such as KO t Bu, NaO t Bu, LiO t Bu, NaH, silylamides, Ag 2 O and phosphazene bases.
  • the carbene can also be released by removing volatile substances, for example lower alcohols such as methanol, ethanol, for example at elevated temperature and/or reduced pressure, from precursor compounds of the carbene ligands. Corresponding processes are known to those skilled in the art.
  • the contacting is preferably effected in a solvent.
  • Suitable solvents are known to those skilled in the art and are preferably selected from the group consisting of aromatic or aliphatic solvents, for example benzene or toluene, cyclic or acyclic ethers, alcohols, esters, amides, ketones, nitriles, halogenated compounds and mixtures thereof.
  • Particularly preferred solvents are toluene, xylenes, dioxane and THF.
  • the molar ratio of metal-noncarbene complex used to carbene ligand precursor used is generally 1:10 to 10:1, preferably 1:1 to 1:5, more preferably 1:2 to 1:4.
  • the contacting is generally effected at a temperature of 20 to 200° C., preferably 50 to 150° C., more preferably 60 to 130° C.
  • the reaction time depends on the desired carbene complex and is generally 0.02 to 50 hours, preferably 0.1 to 24 hours, more preferably 1 to 12 hours.
  • the complexes of the general formula (I) obtained after the reaction can optionally be purified by processes known to those skilled in the art, for example washing, crystallization or chromatography, and optionally isomerized under conditions likewise known to those skilled in the art, for example thermally or photochemically.
  • the aforementioned heteroleptic complexes and mixtures thereof are outstandingly suitable as emitter molecules in organic light-emitting diodes (OLEDs). Variations in the ligands make it possible to provide corresponding complexes which exhibit electroluminescence in the red, green and especially in the blue region of the electromagnetic spectrum.
  • the inventive heteroleptic complexes of the general formula (I) are therefore outstandingly suitable as emitter substances, since they have emission (electroluminescence) in the visible region of the electromagnetic spectrum, for example at 400 to 800 nm, preferably 400 to 600 nm.
  • the inventive heteroleptic complexes make it possible to provide compounds which have electroluminescence in the red, green and especially in the blue region of the electromagnetic spectrum. It is thus possible, with the aid of the inventive heteroleptic complexes as emitter substances, to provide industrially usable OLEDs.
  • inventive heteroleptic complexes of the general formula (I) are suitable as matrix material, charge transport material, especially hole transport material, and/or charge blocker material.
  • the inventive heteroleptic complex of the general formula (I) are preferably suitable as emitter and/or hole transport material, more preferably as emitter.
  • the present application therefore further provides an OLED comprising at least one inventive heteroleptic complex of the general formula (I).
  • inventive heteroleptic complex of the general formula (I) is preferably employed in the OLED as emitter, matrix material, charge transport material, expecially hole transport material, and/or hole blocker, more preferably as emitter and/or hole transport material, particularly preferably as emitter.
  • the present application also provides for the use of the heteroleptic complexes of the general formula (I) as a light-emitting layer in OLEDs, preferably as an emitter, matrix material, charge transport material, especially hole transport material, and/or charge blocker, more preferably as emitter and/or hole transport material, particularly preferably as emitter.
  • Organic light-emitting diodes are in principle formed from a plurality of layers:
  • the OLED does not comprise all of the layers mentioned, an OLED formed from the layers (1) (anode), (3) (light-emitting layer) and (5) (cathode) is for example also useful, wherein the functions of the layers (2) (hole-transport layer) and (4) (electron-transporting layer) are taken over by the adjacent layers.
  • OLEDs comprising the layers (1), (2), (3) and (5) respectively the layers (1), (3), (4) and (5) are also suitable.
  • the heteroleptic complexes of the general formula (I) are preferably used as emitter molecules and/or matrix materials in the light-emitting layer (3).
  • the inventive heteroleptic complexes of the general formula (I) can also be employed—in addition to the application as emitter molecules and/or matrix materials in the light-emitting layer (3) or instead of the application in the light-emitting layer—as charge transport material in the hole-transporting layer (2) or in the electron-transporting layer (4) and/or as charge blocker, wherein the application as charge transport material in the hole-transporting layer (2) (hole-transport material) is preferred.
  • the present application therefore further provides a light-emitting layer comprising at least one of the inventive heteroleptic complexes of the general formula (I), preferably as emitter molecule.
  • a light-emitting layer comprising at least one of the inventive heteroleptic complexes of the general formula (I), preferably as emitter molecule.
  • Preferred heteroleptic complexes of the general formula (I) have already been specified above.
  • heteroleptic complexes of the general formula (I) used in accordance with the invention may be present in the light-emitting layer in substance, i.e. without further additions.
  • further compounds are present in the light-emitting layer.
  • a fluorescent dye may be present in order to alter the emission color of the heteroleptic complex used as the emitter molecule.
  • a diluent material matrix material
  • This diluent material may be a polymer, for example poly(N-vinylcarbazole) or polysilane.
  • the diluent material may, however, likewise be a small molecule, for example 4,4′-N,N′-dicarbazolebiphenyl (CDP) or tertiary aromatic amines.
  • CDP 4,4′-N,N′-dicarbazolebiphenyl
  • the proportion of the inventive heteroleptic complexes of the general formula (I) used in the light-emitting layer is generally less than 40% by weight, preferably 3 to 30% by weight.
  • the inventive heteroleptic complexes of the general formula (I) are preferably used in a matrix.
  • the light-emitting layer thus preferably comprises at least one inventive heteroleptic complex of the general formula (I) and at least one matrix material as diluent material.
  • Suitable matrix materials are—in addition to the aforementioned dilution materials—in principle the materials specified hereinafter as hole and electron transport materials, and also carbene complexes, for example the carbene complexes of the formula (I) or the carbene complexes mentioned in WO 2005/019373.
  • Particularly suitable are carbazole derivatives, for example 4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl (CDBP), 4,4′-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(N-carbazolyl)benzene (mCP), and the matrix materials specified in the following applications: WO2008/034758, WO2009/003919.
  • WO2007108459 H-1 to H-37
  • H-20 to H-22 and H-32 to H-37 most preferably H-20, H-32, H-36, H-37,
  • WO2008035571 A1 Host 1 to Host 6
  • JP2010135467 compounds 1 to 46 and Host-1 to Host-39 and Host-43
  • one or more compounds of the general formula (X) specified hereinafter are used as matrix material.
  • Preferred embodiments of the compounds of the general formula (X) are likewise specified hereinafter.
  • the matrix materials mentioned above as well as the compounds of the general formula (X) mentioned below are not only applicable as matrix material in the light-emitting layer, but also as matrix materials in other layers of an OLED, for example in the electron-transport layer and/or in the hole transport layer. It is also possible, to apply two or more different matrix materials mentioned before and/or compounds of the general formula (X) mentioned below as matrix materials.
  • the HOMO (highest occupied molecular orbital) of the hole-transporting layer should be aligned to the work function of the anode
  • the LUMO (lowest unoccupied molecular orbital) of the electron-transporting layer should be aligned to the work function of the cathode.
  • the present application further provides an OLED comprising at least one inventive light-emitting layer.
  • the further layers in the OLED may be formed from any material which is typically used in such layers and is known to those skilled in the art.
  • Suitable materials for the aforementioned layers are known to those skilled in the art and are specified, for example, in H. Meng, N. Herron, Organic Small Molecule Materials for Organic Light - Emitting Devices in Organic Light - Emitting Materials and Devices , eds: Z. Li, H. Meng, Taylor & Francis, 2007, Chapter 3, pages 295 to 411.
  • the anode is an electrode which provides positive charge carriers. It may be composed, for example, of materials which comprise a metal, a mixture of different metals, a metal alloy, a metal oxide or a mixture of different metal oxides. Alternatively, the anode may be a conductive polymer. Suitable metals comprise the metals of groups 11, 4, 5 and 6 of the Periodic Table of the Elements, and also the transition metals of groups 8 to 10. When the anode is to be transparent, mixed metal oxides of groups 12, 13 and 14 of the Periodic Table of the Elements are generally used, for example indium tin oxide (ITO). It is likewise possible that the anode (1) comprises an organic material, for example polyaniline, as described, for example, in Nature, Vol. 357, pages 477 to 479 (Jun. 11, 1992). At least either the anode or the cathode should be at least partly transparent in order to be able to emit the light formed.
  • ITO indium tin oxide
  • Suitable hole transport materials for layer (2) of the inventive OLED are disclosed, for example, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Vol. 18, pages 837 to 860, 1996. Either hole-transporting molecules or polymers may be used as the hole transport material.
  • Customarily used hole-transporting molecules are selected from the group consisting of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl ( ⁇ -NPD), N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine (ETPD), tetrakis(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA), ⁇ -phenyl-4-N,N-diphenylamin
  • Customarily used hole-transporting polymers are selected from the group consisting of polyvinylcarbazoles, (phenylmethyl)polysilanes and polyanilines. It is likewise possible to obtain hole-transporting polymers by doping hole-transporting molecules into polymers such as polystyrene and polycarbonate. Suitable hole-transporting molecules are the molecules already mentioned above.
  • carbene complexes are, for example, the inventive carbene complexes of the general formula (I), carbene complexes as described in WO 2005/019373 A2, WO 2006/056418 A2, WO 2005/113704, WO 2007/115970, WO 2007/115981 and WO 2008/000727.
  • a suitable carbene complex is Ir(DPBIC) 3 with the formula:
  • mixtures in the hole-transporting layer in particular mixtures which lead to electrical p-doping of the hole-transporting layer.
  • p-Doping is achieved by the addition of oxidizing materials.
  • These mixtures may, for example, be the following mixtures: mixtures of the abovementioned hole transport materials with at least one metal oxide, for example MoO 2 , MoO 3 , WO x , ReO 3 , and/or preferably MoO 3 and/or ReO 3 , more preferably ReO 3 or mixtures comprising the aforementioned hole transport materials and one or more compounds selected from V 2 O 5 , 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ), 2,5-bis(2-hydroxyethoxy)-7,7,8,8-tetracyanoquinodimethane, bis(tetra-n-buty
  • oxinoid compounds such as tris(8
  • Layer (4) may serve both to ease the electron transport and as a buffer layer or as a barrier layer in order to prevent quenching of the exciton at the interfaces of the layers of the OLED. Layer (4) preferably improves the mobility of the electrons and reduces quenching of the exciton.
  • mixtures of at least two materials in the electron-transporting layer in which case at least one material is electron-conducting.
  • at least one material is electron-conducting.
  • at least one phenanthroline compound is used in such mixed electron-transporting layers.
  • alkali metal hydroxyquinolate complexes for example Liq.
  • mixtures may, for example, be mixtures of the abovementioned electron transport materials with alkali/alkaline earth metals or alkali/alkaline earth metal salts, for example Li, Cs, Ca, Sr, Cs 2 CO 3 , with alkali metal complexes, for example 8-hydroxyquinolatolithium (Liq), and with Y, Ce, Sm, Gd, Tb, Er, Tm, Yb, Li 3 N, Rb 2 CO 3 , dipotassium phthalate, W(hpp) 4 from EP 1786050, or with compounds as described in EP1837926 B1.
  • alkali/alkaline earth metals or alkali/alkaline earth metal salts for example Li, Cs, Ca, Sr, Cs 2 CO 3
  • alkali metal complexes for example 8-hydroxyquinolatolithium (Liq)
  • the present invention therefore also relates to an inventive OLED which comprises an electron-transporting layer comprising at least two different materials, of which at least one material should be electron-conductive.
  • the present invention relates to an inventive OLED wherein the electron-transporting layer comprises at least one phenanthroline derivative.
  • the invention relates to an inventive OLED wherein the electron-transporting layer comprises at least one phenanthroline derivative and at least one alkali metal hydroxyquinolate complex.
  • the invention relates to an inventive OLED wherein the electron-transporting layer comprises at least one phenanthroline derivative and 8-hydroxyquinolatolithium.
  • hole transport materials and electron-transporting materials can fulfill several functions.
  • some of the electron-transporting materials are simultaneously hole-blocking materials if they have a low-lying HOMO.
  • the charge-transporting layers may also be electronically doped in order to improve the transport properties of the materials used, in order firstly to make the layer thickness more generous (avoidance of pinholes/short circuits) and in order secondly to minimize the operating voltage of the device.
  • the hole transport materials may for example be doped with electron acceptors, phthalocyanines respectively arylamines like TPD or TDTA may be for example doped with tetrafluorotetracyano-chinodimethane (F4-TCNQ).
  • Electronic doping is known to those skilled in the art and is disclosed, for example, in W. Gao, A. Kahn, J. Appl. Phys., Vol. 94, No. 1, 1. July 2003 (p-doped organic layers); A.
  • the cathode (5) is an electrode which serves to introduce electrons or negative charge carriers.
  • the cathode may be any metal or nonmetal which has a lower work function than the anode. Suitable materials for the cathode are selected from the group consisting of alkali metals of group 1, for example Li, Cs, alkaline earth metals of group 2, metals of group 12 of the Periodic Table of the Elements, comprising the rare earth metals and the lanthanides and actinides. In addition, metals such as aluminum, indium, calcium, barium, samarium and magnesium, and combinations thereof, may be used.
  • lithium-comprising organometallic compounds such as 8-hydroxyquinolatolithium (Liq) or LiF or at least one of the following compounds (Cs 2 CO 3 , KF, CsF or NaF may be applied between the organic layer and the cathode as an electron injection layer in order to reduce the operating voltage.
  • organometallic compounds such as 8-hydroxyquinolatolithium (Liq) or LiF or at least one of the following compounds (Cs 2 CO 3 , KF, CsF or NaF may be applied between the organic layer and the cathode as an electron injection layer in order to reduce the operating voltage.
  • the OLED of the present invention may additionally comprise further layers which are known to those skilled in the art.
  • a layer which eases the transport of the positive charge and/or matches the band gaps of the layers to one another may be applied between the layer (2) and the light-emitting layer (3).
  • this further layer may serve as a protective layer.
  • additional layers may be present between the light-emitting layer (3) and the layer (4) in order to ease the transport of the negative charge and/or to match the band gaps between the layers to one another.
  • this layer may serve as a protective layer.
  • the inventive OLED in addition to the layers (1) to (5), comprises at least one of the further layers mentioned below:
  • the OLED does not have all of the layers (1) to (5) mentioned; for example, an OLED comprising layers (1) (anode), (3) (light-emitting layer) and (5) (cathode) is likewise suitable, in which case the functions of layers (2) (hole-transporting layer) and (4) (electron-transporting layer) are assumed by the adjoining layers. OLEDs having layers (1), (2), (3) and (5) or layers (1), (3), (4) and (5) are likewise suitable.
  • Suitable materials for the individual layers are known to those skilled in the art and disclosed, for example, in WO 00/70655.
  • the layers (1), (2), (3), (4) and (5) have been surface-treated in order to increase the efficiency of charge carrier transport.
  • the selection of the materials for each of the layers mentioned is preferably determined by obtaining an OLED having a high efficiency.
  • the inventive OLED can be produced by methods known to those skilled in the art.
  • the OLED is produced by successive vapor deposition of the individual layers onto a suitable substrate.
  • Suitable substrates are, for example, glass, inorganic materials like ITO or IZO or polymer films.
  • customary techniques may be used, such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) and others.
  • the organic layers may be coated from solutions or dispersions in suitable solvents, in which case coating techniques known to those skilled in the art are employed.
  • Suitable coating techniques are, for example, spin-coating, the casting method, the Langmuir-Blodgett (“LB”) method, the inkjet printing method, dip-coating, letterpress printing, screen printing, doctor blade printing, roller printing, reverse roller printing, offset lithography printing, flexographic printing, web printing, spray coating, coating by a brush or pad printing, and the like.
  • LB Langmuir-Blodgett
  • the inkjet printing method dip-coating, letterpress printing, screen printing, doctor blade printing, roller printing, reverse roller printing, offset lithography printing, flexographic printing, web printing, spray coating, coating by a brush or pad printing, and the like.
  • spin-coating the inkjet printing method and the casting method since they are particularly simple and inexpensive to perform.
  • the coating can be obtained using a solution prepared by dissolving the composition in a concentration of 0.0001 to 90% by weight in a suitable organic solvent such as benzene, toluene, xylene, tetrahydrofuran, methyltetrahydrofuran, N,N-dimethylformamide, acetone, acetonitrile, anisole, dichloromethane, dimethyl sulfoxide, water and mixtures thereof.
  • a suitable organic solvent such as benzene, toluene, xylene, tetrahydrofuran, methyltetrahydrofuran, N,N-dimethylformamide, acetone, acetonitrile, anisole, dichloromethane, dimethyl sulfoxide, water and mixtures thereof.
  • all layers of the OLED are prepared with the same coating technique. It is further also possible that two or more coating techniques are carried out in the production of the layers of the OLED.
  • the different layers have the following thicknesses: anode (2) 500 to 5000 ⁇ , preferably 1000 to 2000 ⁇ ( ⁇ ngström); hole-transporting layer (3) 50 to 1000 ⁇ , preferably 200 to 800 ⁇ ; light-emitting layer (4) 10 to 1000 ⁇ , preferably 100 to 800 ⁇ ; electron-transporting layer (5) 50 to 1000 ⁇ , preferably 200 to 800 ⁇ ; cathode (6) 200 to 10 000 ⁇ , preferably 300 to 5000 ⁇ .
  • the position of the recombination zone of holes and electrons in the inventive OLED and thus the emission spectrum of the OLED may be influenced by the relative thickness of each layer.
  • the thickness of the electron transport layer should preferably be selected such that the electron/hole recombination zone is within the light-emitting layer.
  • the ratio of the layer thicknesses of the individual layers in the OLED is dependent upon the materials used. The layer thicknesses of any additional layers used are known to those skilled in the art.
  • the present invention also relates to an OLED comprising at least one inventive heteroleptic complex of the general formula (I), and at least one compound of the general formula (X)
  • two units of the general formula (X) are bridged to one another via a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom, via a bond or via O.
  • the compounds of the formula (X) have the formula (XI) or (XI*):
  • the compounds of the general formula (X) can be used as a matrix (diluent material), hole/exciton blocker, electron/exciton blocker, electron transport material or hole transport material in combination with the heteroeleptic complexes claimed, which then preferably serve as emitters.
  • Inventive OLEDs which include both at least one compound of the formula (X) and a compound of the formula (I) exhibit particularly good efficiencies and lifetimes. Depending on the function in which the compound of the formula (X) is used, it is present in pure form or in different mixing ratios.
  • one or more compounds of the formula (X) are used as matrix material in the light-emitting layer.
  • aryl radical or group, heteroaryl radical or group, alkyl radical or group, cycloalkyl radical or group, heterocycloalkyl radical or group, alkenyl radical or group, alkynyl radical or group, and groups with donor and/or acceptor action are each defined as follows:
  • An aryl radical is understood to mean a radical having a base skeleton of 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, which is formed from an aromatic ring or a plurality of fused aromatic rings.
  • Suitable base skeletons are, for example, phenyl, naphthyl, anthracenyl or phenanthrenyl, indenyl or fluorenyl.
  • This base skeleton may be unsubstituted (which means that all carbon atoms which are substitutable bear hydrogen atoms), or may be substituted at one, more than one or all substitutable positions of the base skeleton.
  • Suitable substituents are, for example, deuterium, alkoxy radicals, aryloxy radicals, alkylamino groups, arylamino groups, carbazolyl groups, silyl groups, SiR 78 R 79 R 80 , suitable silyl groups SiR 78 R 79 R 80 being specified below, alkyl radicals, preferably alkyl radicals having 1 to 8 carbon atoms, more preferably methyl, ethyl or i-propyl, aryl radicals, preferably C 6 -aryl radicals, which may in turn be substituted or unsubstituted, heteroaryl radicals, preferably heteroaryl radicals which comprise at least one nitrogen atom, more preferably pyridyl radicals and carbazolyl radicals, alkenyl radicals, preferably alkenyl radicals which bear one double bond, more preferably alkenyl radicals having one double bond and 1 to 8 carbon atoms, alkynyl radicals, preferably alkynyl radical
  • the substituted aryl radicals most preferably bear substituents selected from the group consisting of methyl, ethyl, isopropyl, alkoxy, heteroaryl, halogen, pseudohalogen and amino, preferably arylamino.
  • the aryl radical or the aryl group is preferably a C 6 -C 18 -aryl radical, more preferably a C 6 -aryl radical, which is optionally substituted by at least one or more than one of the aforementioned substituents.
  • the C 6 -C 18 -aryl radical, preferably C 6 -aryl radical more preferably has none, one, two, three or four, most preferably none, one or two, of the aforementioned substituents.
  • a heteroaryl radical or a heteroaryl group is understood to mean radicals which differ from the aforementioned aryl radicals in that at least one carbon atom in the base skeleton of the aryl radicals is replaced by a heteroatom, and in that the base skeleton of the heteroaryl radicals preferably has 5 to 18 ring atoms.
  • Preferred heteroatoms are N, O and S.
  • Heteroaryl radicals suitable with particular preference are nitrogen-containing heteroaryl radicals. Most preferably, one or two carbon atoms of the base skeleton are replaced by heteroatoms, preferably nitrogen.
  • the base skeleton is especially preferably selected from systems such as pyridine, pyrimidine and five-membered heteroaromatics such as pyrrole, furan, pyrazole, imidazole, thiophene, oxazole, thiazole, triazole.
  • the heteroaryl radicals may be fused ring systems, for example benzofuryl, benzothienyl, benzopyrrolyl, dibenzofuryl, dibenzothienyl, phenanthrolinyl, carbazolyl radicals, azacarbazolyl radicals or diazacarbazolyl radicals.
  • the base skeleton may be substituted at one, more than one or all substitutable positions of the base skeleton. Suitable substituents are the same as have already been specified for the aryl groups.
  • alkyl radical or an alkyl group is understood to mean a radical having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 8, most preferably 1 to 4 carbon atoms.
  • This alkyl radical may be branched or unbranched and optionally be interrupted by one or more heteroatoms, preferably Si, N, O or S, more preferably N, O or S.
  • this alkyl radical may be substituted by one or more of the substituents specified for the aryl groups.
  • the alkyl radicals present in accordance with the invention may have at least one halogen atom, for example F, CI, Br or I, especially F.
  • the alkyl radicals present in accordance with the invention may be fully fluorinated. It is likewise possible that the alkyl radical bears one or more (hetero)aryl groups. In the context of the present application, for example, benzyl radicals are thus substituted alkyl radicals. In this context, all of the (hetero)aryl groups listed above are suitable.
  • the alkyl radicals are more preferably selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, iso-butyl and tert-butyl, very particular preference being given to methyl and ethyl.
  • a cycloalkyl radical or a cycloalkyl group is understood to mean a radical having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms.
  • This base skeleton may be unsubstituted (which means that all carbon atoms which are substitutable bear hydrogen atoms) or substituted at one, more than one or all substitutable positions of the base skeleton.
  • Suitable substituents are the groups already mentioned above for the aryl radicals. It is likewise possible that the cycloalkyl radical bears one or more (hetero)aryl groups. Examples of suitable cycloalkyl radicals are cyclopropyl, cyclopentyl and cyclohexyl.
  • a heterocycloalkyl radical or a heterocycloalkyl group is understood to mean radicals which differ from the aforementioned cycloalkyl radicals in that at least one carbon atom in the base skeleton of the cycloalkyl radicals is replaced by a heteroatom.
  • Preferred heteroatoms are N, O and S.
  • Most preferably, one or two carbon atoms of the base skeleton of the cycloalkyl radicals are replaced by heteroatoms.
  • suitable heterocycloalkyl radicals are radicals derived from pyrrolidine, piperidine, piperazine, tetrahydrofuran, dioxane.
  • alkenyl radical or an alkenyl group is understood to mean a radical which corresponds to the aforementioned alkyl radicals having at least two carbon atoms, with the difference that at least one C—C single bond of the alkyl radical is replaced by a C—C double bond.
  • the alkenyl radical preferably has one or two double bonds.
  • alkynyl radical or an alkynyl group is understood to mean a radical which corresponds to the aforementioned alkyl radicals having at least two carbon atoms, with the difference that at least one C—C single bond of the alkyl radical is replaced by a C—C triple bond.
  • the alkynyl radical preferably has one or two triple bonds.
  • SiR 78 R 79 R 80 group is understood to mean a silyl radical in which
  • R 78 , R 79 and R 80 are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl or OR 73 .
  • SiR 74 R 75 R 76 group is understood to mean a silyl radical in which
  • R 74 , R 75 and R 76 are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl or OR 73 .
  • a group or a substituent with donor or acceptor action is understood to mean the following groups:
  • Groups with donor action are understood to mean groups which have a +I and/or +M effect, and groups with acceptor action are understood to mean groups which have a —I and/or -M effect.
  • Preferred suitable groups are selected from C 1 -C 20 -alkoxy, C 6 -C 30 -aryloxy, C 1 -C 20 -alkylthio, C 6 -C 30 -arylthio, SiR 81 R 82 R 83 , OR 73 , halogen radicals, halogenated C 1 -C 20 -alkyl radicals, carbonyl (—CO(R 81 )), carbonylthio (—C ⁇ O(SR 81 )), carbonyloxy (—C ⁇ O(OR 81 )), oxycarbonyl (—OC ⁇ O(R 81 )), thiocarbonyl (—SC ⁇ O(R 81 )), amino (—NR 81 R 82 ), pseudohalogen radicals, amido (—C ⁇
  • R 81 , R 82 and R 83 radicals mentioned in the aforementioned groups with donor or acceptor action are each independently:
  • R 81 , R 82 and R 83 radicals are more preferably C 1 -C 6 -alkyl, e.g. methyl, ethyl or i-propyl, or phenyl.
  • R 81 , R 82 and R 83 are preferably each independently substituted or unsubstituted C 1 -C 20 -alkyl or substituted or unsubstituted aryl, preferably phenyl.
  • Preferred substituents with donor or acceptor action are selected from the group consisting of:
  • CF 3 CH 2 F, CHF 2 or C 2 F 5 ; amino, preferably dimethylamino, diethylamino or diarylamino, more preferably diarylamino; pseudohalogen radicals, preferably CN, —C(O)OC 1 -C 4 -alkyl, preferably —C(O)OMe, P(O)R 2 , preferably P(O)Ph 2 .
  • Very particularly preferred substituents with donor or acceptor action are selected from the group consisting of methoxy, phenyloxy, halogenated C 1 -C 4 -alkyl, preferably CF 3 , CH 2 F, CHF 2 , C 2 F 5 , halogen, preferably F, CN, SiR 81 R 82 R 83 , suitable R 81 , R 82 and R 83 radicals already having been specified, diarylamino (NR 84 R 85 where R 84 , R 85 are each C 6 -C 30 -aryl), —C(O)OC 1 -C 4 -alkyl, preferably —C(O)OMe, P(O)Ph 2 .
  • Halogen groups are preferably understood to mean F, Cl and Br, more preferably F and Cl, most preferably F.
  • Pseudohalogen groups are preferably understood to mean CN, SCN and OCN, more preferably CN.
  • aryl radicals or groups, heteroaryl radicals or groups, alkyl radicals or groups, cycloalkyl radicals or groups, heterocycloalkyl radicals or groups, alkenyl radicals or groups and groups with donor and/or acceptor action may—as mentioned above—be substituted or unsubstituted.
  • an unsubstituted group is understood to mean a group in which the substitutable atoms of the group bear hydrogen atoms.
  • a substituted group is understood to mean a group in which one or more substitutable atom(s) bear(s) a substituent in place of a hydrogen atom at least at one position. Suitable substituents are the substituents specified above for the aryl radicals or groups.
  • radicals having the same numbering occur more than once in the compounds according to the present application, these radicals may each independently have the definitions specified.
  • the T radical in the compounds of the formula (X) is NR 57 , S, O or PR 57 , preferably NR 57 , S or O, more preferably O or S, most preferably O.
  • the R 57 radical is aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, preferably aryl, heteroaryl or alkyl, more preferably aryl, where the aforementioned radicals may be unsubstituted or substituted. Suitable substituents have been specified above.
  • R 65 is more preferably phenyl which may be substituted by the aforementioned substituents or unsubstituted.
  • R 57 is most preferably unsubstituted phenyl.
  • the Q′ group in the compounds of the formula (X) is —NR 58 R 59 , —P(O)R 60 R 61 , —PR 62 R 63 , —S(O) 2 R 64 , —S(O)R 65 , —SR 66 or —OR 67 ; preferably NR 58 R 59 , —P(O)R 60 R 61 or —OR 67 , more preferably —NR 58 R 59 .
  • R 58 to R 67 and R 74 to R 76 radicals are each defined as follows:
  • T is NPh, S or O.
  • —NR 58 R 59 groups suitable with preference are selected from the group consisting of pyrrolyl, 2,5-dihydro-1-pyrrolyl, pyrrolidinyl, indolyl, indolinyl, isoindolinyl, carbazolyl, azacarbazolyl, diazacarbazolyl, imidazolyl, imidazolinyl, benzimidazolyl, pyrazolyl, indazolyl, 1,2,3-triazolyl, benzotriazolyl, 1,2,4-triazolyl, tetrazolyl, 1,3-oxazolyl, 1,3-thiazolyl, piperidyl, morpholinyl, 9,10-dihydroacridinyl and 1,4-oxazinyl, where the aforementioned groups may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, ary
  • Particularly preferred —NR 58 R 59 groups are:
  • Particularly preferred —P(O)R 60 R 61 groups are:
  • a particularly preferred PR 62 R 63 group is:
  • R 55 , R 56 in the compounds of the formula (X) are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a further A group or a group with donor or acceptor action; preferably each independently alkyl, aryl, heteroaryl or a group with donor or acceptor action.
  • R 55 or R 56 may each independently be:
  • a′′ R 55 groups and/or b′ R 56 groups may be present, where a′′ and b′ are:
  • a′′ is 0, 1, 2, 3 or 4; preferably independently 0, 1 or 2; b′ is 0, 1, 2 or 3; preferably independently 0, 1 or 2.
  • At least a′′ or b′ is 0, very especially preferably a′′ and b′ are each 0 or a′′ is 1 and b′ is 0.
  • R 73 in the compounds of the general formula (XI) is generally independently SiR 74 R 75 R 76 , aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, optionally substituted by an OR 77 group.
  • R 77 in compounds of the general formula (XI) is generally independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl.
  • OR 77 substituent optionally present may generally be present in the radicals mentioned at all sites which appear suitable to the person skilled in the art.
  • two units of the general formula (XI) and/or (XI*) are bridged to one another via a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom or via O, where this bridge in the general formula (XI) and/or (XI*) is in each case attached to the silicon atoms in place of R 71 .
  • This bridge is preferably selected from the group consisting of —CH 2 —, —C 2 H 4 —, —C 4 H 8 —, —C 6 H 12 —, —C 8 H 16 —, —C 9 H 18 —, —CH(C 8 H 17 )CH 2 —, —C 2 H 4 (CF 2 ) 8 C 2 H 4 —, —C ⁇ C—, -1,4-(CH 2 ) 2 -phenyl-(CH 2 ) 2 —, 1,3-(CH 2 ) 2 -phenyl-(CH 2 ) 2 —, -1,4-phenyl-, -1,3-phenyl-, —O—, —O—Si(CH 3 ) 2 —O—, —O—Si(CH 3 ) 2 —O—, —O—Si(CH 3 ) 2 —O—Si(CH 3 ) 2 —O—, —O—.
  • the compounds of the general formula (X) have the general formula (XIa), (XIb), (XIc), (XId) or (XIe), i.e. they are preferred embodiments of the compounds of the general formula (XI) or (XI*):
  • R 70 , R 71 or R 72 in the compounds of the general formula (XI) or (XI*) are aromatic units of the general formulae (XIi) and/or (XIi*)
  • R 55 , R 56 , Q′, T, a′ and b′ are each as defined above.
  • the present invention therefore relates, in one embodiment, to an inventive OLED where R 70 , R 71 or R 72 in the compounds of the general formula (XI) or (XI*) are aromatic units of the general formulae (XIi) and/or (XIi*)
  • R 56 , R 56 , Q′, T, a′ and b′ are each as defined above.
  • the present invention relates to an OLED wherein the compound of the general formula (XI) or (XI*) is selected from the following group:
  • T is O or S, preferably O.
  • R 70 , R 71 , R 72 are each defined as follows:
  • Nr R 70 R 71 R 72 1 methyl methyl ethyl 2 methyl methyl i-propyl 3 methyl methyl n-propyl 4 methyl methyl n-butyl 5 methyl methyl i-butyl 6 methyl methyl t-butyl 7 methyl methyl n-pentyl 8 methyl methyl n-hexyl 9 methyl methyl —CH 2 CH 2 C(CH 3 ) 3 10 methyl methyl n-C 8 H 17 11 methyl methyl i-C 8 H 17 12 methyl methyl n-C 10 H 21 13 methyl methyl n-C 12 H 25 16 methyl methyl n-C 18 H 37 17 methyl methyl n-C 30 H 61 19 methyl methyl cyclohexyl 20 methyl methyl C(CH 3 ) 2 Ph 21 methyl methyl —C(CH 3 ) 2 CH(CH 3 ) 2 22 methyl methyl —CCH 2 CH(CH 3 )(C 2 H
  • R 70 , R 71 , R 72 , R 87 , R 88 and R 89 are each defined as follows:
  • R therein is independently Me, phenyl or R 86 , where at least one R radical is R 86 :
  • the present invention relates to an OLED which, as well as at least one metal-carbene complex of the general formula (I), comprises at least one compound of the general formula (X), in which case the compound of the formula (X) is most preferably at least one of the compounds specified below:
  • T is O or S, preferably O.
  • all T groups have the same definition.
  • crosslinked or polymeric materials comprising repeat units based on the general formula (X) in crosslinked or polymerized form together with at least one heteroeleptic complex of the general formula (I).
  • the latter are preferably used as matrix materials.
  • the crosslinked or polymeric materials have outstanding solubility in organic solvents, excellent film-forming properties and relatively high glass transition temperatures.
  • high charge carrier mobilities, high stabilities of color emission and long operating times of the corresponding components can be observed when crosslinked or polymeric materials according to the present invention are used in organic light-emitting diodes (OLEDs).
  • the crosslinked or polymerized materials are particularly suitable as coatings or in thin films since they are thermally and mechanically stable and relatively defect-free.
  • crosslinked or polymerized materials comprising repeat units based on the general formula (X) can be prepared by a process comprising steps (a) and (a):
  • the crosslinked or polymerized materials may be homopolymers, which means that exclusively units of the general formula (X) are present in crosslinked or polymerized form. They may also be copolymers, which means that further monomers are present in addition to the units of the general formula (X), for example monomers with hole-conducting and/or electron-conducting properties, in crosslinked or polymerized form.
  • inventive OLED comprises an emission layer comprising at least one inventive heteroeleptic complex of the general formula (I), at least one matrix material of the formula (X), and optionally at least one further hole-transporting matrix material.
  • the inventive OLEDs can be used in all devices in which electroluminescence is useful. Suitable devices are preferably selected from stationary and mobile visual display units and illumination means. The present invention therefore also relates to a device selected from the group consisting of stationary visual display units and mobile visual display units and illumination means, comprising an inventive OLED.
  • Stationary visual display units are, for example, visual display units of computers, televisions, visual display units in printers, kitchen appliances and advertising panels, illuminations and information panels.
  • Mobile visual display units are, for example, visual display units in cellphones, laptops, digital cameras, mp-3 players, smartphones, vehicles, and destination displays on buses and trains.
  • inventive heteroleptic complexes of the general formula (I) can be used in OLEDs with inverse structure.
  • the inventive complexes are preferably used in turn in these inverse OLEDs in the light-emitting layer.
  • the structure of inverse OLEDs and the materials typically used therein are known to those skilled in the art.
  • a further embodiment of the present invention is a white OLED comprising at least one heteroleptic complex of the general formula (I).
  • the heteroleptic complex of the general formula (I) is employed in the white OLED as emitter material. Preferred embodiments of the heteroleptic complex of the general formula (I) are mentioned before.
  • Beside the at least one heteroleptic complex of the general formula (I) the white OLED may comprise at least one compound of the formula (X).
  • the compound of formula (X) is preferably employed as matrix material. Preferred compounds of the formula (X) are mentioned before.
  • the OLED In order to obtain white light, the OLED must generate light which colors the entire visible range of the spectrum.
  • organic emitters normally emit only in a limited portion of the visible spectrum—i.e. are colored.
  • White light can be generated by the combination of different emitters. Typically, red, green and blue emitters are combined.
  • the prior art also discloses other methods for formation of white OLEDs, for example the triplet harvesting approach. Suitable structures for white OLEDs or methods for formation of white OLEDs are known to those skilled in the art.
  • the present invention also relates to an organic electronic component, preferably an organic light-emitting diode (OLED), organic photovoltaic cell (OPV), organic filed-effect transistor (OFET) or light-emitting electrochemical cell (LEEC), comprising a least one inventive heteroleptic complex of the general formula (I).
  • OLED organic light-emitting diode
  • OPFET organic field-effect transistor
  • LEEC light-emitting electrochemical cell
  • N-(2,6-Diisopropylphenyl)-2-phenylimidazole L1 is synthesized analogously to example 14 in WO2006/121811.
  • the synthesis of 5-methoxy-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole C1 is effected according to D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Che—m. 1995, 107, 9, 1119-1122 or D. Enders, K. Breuer, U. Kallank, T. Balensiefer, Synthesis 2003, 8, 1292-1295.
  • 3-(2,6-Dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridine L3 is synthesized analogously to example 10 in WO 2007/095118.
  • the synthesis of the ligand precursor 1-isopropyl-1,2,4-triazolo[4,3-f]phenanthridinium iodide C3 is effected as described in WO 2009/050281.
  • the synthesis of the exciton and hole blocker 2,8-bis(triphenylsilyl)-dibenzofuran LB1 is disclosed in synthesis example 4g in WO 2009/003898.
  • Em1-i corresponds to the configuration IVa or IVb of the pseudo-facial isomer S4a or S4b.
  • Em1-i is present as the racemate; for crystal structure see FIG. 2 , the sample for the x-ray structure analysis is crystallized from cyclohexane/ethyl acetate (cyclohexane still present in the crystals).
  • the photoluminescence quantum yield of the facial isomer Em1-i is 1.36 times the quantum yield of the meridional isomer Em1-s.
  • the cooling bath is removed, and the mixture is allowed to come to room temperature in a water bath within approx. 30 min and stirred for a further two hours. Subsequently, 60 ml of saturated sodium chloride solution are added cautiously (slightly exothermic reaction, temperature rise 1-2° C.). The organic phase is removed and freed of the solvent under reduced pressure. The oily red-brown residue is taken up in 900 ml of dichloromethane and washed successively with 500 ml of HCl solution (1 N) and 400 ml of water. The organic phase is dried over magnesium sulfate and freed of the solvent under reduced pressure.
  • 119.00 g of the first stage (comprise 110.66 g, 447.9 mmol of 4-bromodibenzofuran) are dissolved in 700 ml of dimethylformamide and admixed successively with 37.15 g (545.7 mmol) of imidazole, 15.80 g (83.0 mmol) of copper(I) iodide and 83.20 g (602.0 mmol) of potassium carbonate. The mixture is stirred at 150° C. for 48 h, in the course of which a further 3.75 g (55.1 mmol) of imidazole are added after 24 h and a further 1.93 g (28.3 mmol) after 44 h.
  • Em2-i corresponds to the configuration IVa or IVb of the pseudo-facial isomer S4a or S4b.
  • Em2-1 is present as the racemate; for crystal structure see FIG. 3 , the sample for the x-ray structure analysis was crystallized from tetra hydrofuran/n-hepta ne.
  • the photoluminescence quantum yield of the facial isomer Em2-i is 1.44 times the quantum yield of the isomer Em2-s.
  • ⁇ 0.79 (d, 3H), 0.89 (d, 3H), 0.90 (d, 3H), 0.97 (d, 6H), 1.02 (d, 3H), 1.10 (d, 3H), 1.15 (d, 3H), 1.16 (d, 3H), 1.47 (d, 3H), 2.03 (sept, 1H), 2.47 (sept, 1H), 2.65 (sept, 1H), 2.76 (sept, 1H), 4.47 (sept, 1H), 6.13 (d, 1H), 6.21 (d, 1H), 6.35 (d, 1H), 6.46 (m c , 3H), 6.58 (dd, 2H), 6.65-6.76 (m, 3H), 6.93 (dd, 1H), 7.09 (dd, 1H), 7.15 (d, 1H), 7.25 (dd, 1H), 7.28-7.33 (m, 3H), 7.44-7.52 (m, 2H), 7.58 (dd, 1H), 7.67-7.76 (m, 2H), 8.39 (
  • Em3-s A suspension of 2.1 g of Em3-s in 2000 ml of acetonitrile is irradiated with a moderate-pressure mercury immersion lamp at room temperature for 8 h (TQ150 with Duran sheath). Subsequently, the solvent is removed under reduced pressure. The residue was stirred twice with acetone and filtered. 1.6 g of Em3-i were obtained as a yellow powder (76%).
  • ⁇ 0.68 (d, 3H), 0.75 (d, 3H), 0.82 (d, 3H), 0.96 (d, 3H), 0.99 (d, 3H), 1.05 (d, 3H), 1.13 (d, 3H), 1.20 (d, 3H), 1.24 (d, 3H), 1.60 (d, 3H), 1.79 (sept, 1H), 2.42 (sept, 1H), 2.51 (sept, 1H), 2.76 (sept, 1H), 4.56 (sept, 1H), 6.10 (dd, 2H), 6.30-6.35 (m, 1H), 6.38-6.45 (m, 2H), 6.53 (d, 1H), 6.61 (dd, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 6.74-6.78 (m, 2H), 6.79 (d, 1H), 6.96 (dd, 1H), 7.07-7.15 (m, 1H), 7.19 (d, 1H), 7.22 (d, 1H), 7.27-7.34 (m,
  • the photoluminescence quantum yield of the isomer Em3-i is 1.21 times the quantum yield of the isomer Em3-s.
  • Stage 1 Benzonitrile (51.5 g, 0.50 mol) is admixed with ethanol (anhydrous, 25 ml). Then a constant stream of HCl gas is introduced over 2 h and the mixture is subsequently stirred at room temp. for 48 h, in the course of which a solid forms. The solvent is drawn off from the reaction mixture under reduced pressure (95 g).
  • Stages 2+3 12 g of stage 1 (64.6 mmol) are again dissolved in EtOH (120 ml), and phenylhydrazine (9.4 g, 84 mmol, 1.3 equiv.) is added, in the course of which a solid forms. Triethylamine (22 ml, 162 mmol, 2.5 equiv.) is added and then the mixture is stirred at room temp. for 16 h. The solvent is again removed from the reaction mixture under reduced pressure at room temp., such that the amidrazone formed remains, still moist. After the addition of formic acid (200 ml), the mixture is heated to reflux for 3.5 h.
  • Stage 4 The triazole of the preceding stage (1.5 g, 66 mmol) is dissolved in THF (anhydrous, 40 ml), admixed with MeI (14 ml) and heated to reflux for 5 days. The solid obtained is filtered off, recrystallized repeatedly (CH 2 Cl 2 /n-hexane) and dried (780 mg, 32%).
  • the photoluminescence quantum yield of the isomer Em-4-i has 1.40 times the quantum yield of the isomer Em-4-s.
  • Stage 1 Aq. NaHCO 3 solution (5%, 330 g, 190 mmol, 2.0 equiv.) is added at room temp. to a suspension of o-tolylhydrazine hydrochloride (15 g, 97 mmol) in methyl chloride (450 ml). After stirring for 30 minutes, the biphasic solution is phase-separated. The organic phase is dried over Na 2 SO 4 , freed of the solvent and dried under reduced pressure at 60° C. to isolate tolylhydrazine as a pale yellow solid (7.3 g, 62%).
  • Stage 2 Benzoyl chloride (8.4 g, 60 mmol, 1.0 equiv.) is initially charged in toluene (anhydrous, 60 ml) and cooled to 5° C. Then aniline (5.6 g, 60 mmol, 1.0 equiv.) is added, and the reaction mixture is heated to reflux for 16 h and then stirred at room temp. for a further 48 h. Then the mixture is heated to 80° C., thionyl chloride (21.4 g, 180 mmol, 3.0 equiv.) is added at this temperature and the mixture is stirred for a further 2 h. Then the mixture is cooled to room temp.
  • reaction mixture is admixed with THF (anhydrous, 180 ml) and triethylamine (9.1 g, 90 mmol, 1.5 equiv.) and cooled to 5° C., and then the tolylhydrazine of stage 1 (7.3 g, 60 mmol), dissolved in THF (20 ml), is added. The mixture is stirred at room temperature for 16 h. After the removal of the solvent, the residue is recrystallized from acetic acid (2%, 150 ml), washed with iPrOH (80 ml, 20 ml) and dried (10.3 g, 57%).
  • Stage 3 Triethyl orthoformate (9.0 ml, 8.1 g, 56 mmol, 5.6 equiv.) and 3 g of the hydrazone of stage 2 (10 mmol) are initially charged, ammonium iodide (1.4 g, 10 mmol, 1.0 equiv.) is added and the suspension is heated to reflux for 7 h. After cooling, the solid is filtered off with suction and washed repeatedly with n-hexane and ethyl acetate, from which the iodide salt is obtained as a gray powder (3.2 g, 73%).
  • the photoluminescence quantum yield of the isomerized Em5-i complex mixture has 1.50 times the quantum yield of the Em5-s complex mixture.
  • the synthesis is performed analogously to D1.
  • the precipitate obtained is extracted with dichloromethane. After removing the solvent, D2 is obtained from the extract in a yield of 36%.
  • CEm1 corresponds to compound (N-3) from WO 2006067074
  • complex CEm1 is not suitable as an emitter in OLEDs.
  • CEm2 corresponds to the compound “Compound 3” from WO 2006121811. The synthesis was analogous WO 2006121811.
  • the ITO substrate used as the anode is cleaned first with commercial detergents for LCD production (Deconex® 20NS, and 25ORGAN-ACID® neutralizing agent) and then in an acetone/isopropanol mixture in an ultrasound bath. To eliminate possible organic residues, the substrate is exposed to a continuous ozone flow in an ozone oven for a further 25 minutes. This treatment also improves the hole injection properties of the ITO.
  • the hole injection layer AJ20-1000 from Plexcore respectively PEDT: PSS (CLEVIOS P AR 4083) from H. C. Starck is spun on from solution.
  • the organic materials specified below are applied by vapor deposition to the cleaned substrate at about 10 ⁇ 7 -10 ⁇ 9 mbar at a rate of approx. 0.5-5 nm/min.
  • the hole conductor and exciton blocker applied to the substrate is Ir(DPBIC) 3 with a thickness of 45 nm, of which the first 35 nm are doped with MoO x to improve the conductivity,
  • a mixture of emitter and of the compound Ma1 is applied by vapor deposition with a thickness of 40 nm, the latter compound functioning as a matrix material.
  • the material Ma1 is applied by vapor deposition with a thickness of 10 nm as an exciton and hole blocker.
  • an electron transporter BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) is applied by vapor deposition in a thickness of 20 nm, as are a 0.75 nm-thick lithium fluoride layer and finally a 100 nm-thick Al electrode. All components are adhesive-bonded to a glass lid in an inert nitrogen atmosphere.
  • electroluminescence spectra are recorded at different currents and voltages.
  • the current-voltage characteristic is measured in combination with the light output emitted.
  • the light output can be converted to photometric parameters by calibration with a photometer.
  • the lifetime t 1/2 of the diode is defined by the time taken for the luminance to fall to 50% of its initial value. The lifetime measurement is carried out at a constant current.
  • ITO-40 nm AJ20-1000-35 nm Ir(DPBIC) 3 mixed with MoO x -10 nm Ir(DPBIC) 3 -40 nm Ma1 mixed with 20 wt % Em1-i-5 nm Ma1-40 nm electron conductor-1 nm Liq-100 nm Al.
  • the preparation of the OLED is carried out in analogy to Example 17.
  • Imidazoliumiodide C6 corresponds to a pre-intermediate of the compound “example 1” in WO 2006056418.
  • the synthesis is carried out in analogy to the synthesis of the compound “example 1” in WO 2006056418.
  • ⁇ 0.83 (d, 3H), 0.89-0.96 (m, probably interpreted as 4 ⁇ d, 12H), 1.00 (d, 3H), 1.13 (d, 3H), 1.15 (d, 3H), 1.98 (sept, 1H), 2.31 (sept, 1H), 2.70 (sept, 1H), 2.74 (sept, 1H), 3.21 (s, 3H), 6.10 (dd, 2H), 6.37-6.45 (m, 4H), 6.56-6.65 (m, 4H), 6.70 (dd, 1H), 6.83 (m c , 1H), 6.95 (d, 1H), 7.06 (m c , 1H), 7.19 (m c , 2H), 7.25-7.31 (m, 4H), 7.44-7.50 (m, 3H).
  • ⁇ 0.65 (d, 3H), 0.77 (d, 3H), 0.85 (d, 3H), 0.97 (d, 3H), 0.98 (d, 3H), 1.02 (d, 3H), 1.13 (d, 6H), 1.82 (sept, 1H), 2.33 (sept, 1H), 2.54 (sept, 1H), 2.67 (sept, 1H), 3.04 (s, 3H), 6.09 (dd, 2H), 6.37 (td, 1H), 6.40-6.44 (m, 3H), 6.50 (m, 1H), 6.59 (d, 1H), 6.61 (td, 1H), 6.68 (d, 1H), 6.70 (d, 1H), 6.72 (d, 1H), 6.86 (d, 1H), 6.96 (br.s, 1H), 7.14 (m c , 2H), 7.20-7.23 (m, 1H), 7.23-7.31 (m, 3H), 7.44-7.50 (m, 3H).
  • the photoluminescence quantum efficiency of the isomer Em9-i has the 1.14-fold value of the quantum efficiency of the isomer Em9-s.
  • a solution of 19.50 g (58.7 mmol) 2-anilino-1,2-di-o-tolyl-ethanone in 80 ml of tetrahydrofuran is meaned with 7.80 g (88.1 mmol) acetformylanhydride and stirred for 17 hours at room temperature.
  • the reaction mixture is reduced at a rotarap to a syrup and purified at silica gel with a petrol ether-acetic ester solution as eluent at first in a ratio of 10:1 then 1:1. After removal of the solvent 18.4 g (91%) of a nearly colorless syrup are obtained.
  • Step 4 Preparation of 1,3-diphenyl-4,5-di-o-tolylimidazolium-tetrafluoroborate C7
  • a suspension of 1.61 g (3.30 mmol) 1,3-diphenyl-4,5-di-o-tolyl-imidazolium-tetrafluoroborate in 25 ml of toluene are stirred for 15 min under argon at room temperature and then cooled to 0° C. 12.6 ml (6.29 mmol) 0.5 M potassium-bis(trimethylsilyl)-amide in toluene are added with 1 min.
  • the reaction solution is then stirred for 15 min at 0-12° C., and subsequently, 2.50 g (1.50 mmol) bis(iridium-p-chloro-complex) D1 are added. It is purged with 5 ml of toluene.
  • the orange-yellow suspension is heated under reflux to boiling. After 75 min the reaction solution is cooled to room temperature diluted with 20 ml acetic ester and then extracted two times with 20 ml of phosphate buffer solution (ph 7). The organic phase is separated, dryed over sodium sulfate and then reduced to dryness. The solid is shortly heated in 150 ml of methanol under reflux to boiling. After cooling of the suspension to 50° C. the solid is sucked, washed two times with 10 ml of methanol each and dryed. 2.52 g of a yellow solid are obtained. The filtrate is reduced to 40 ml and stirred overnight at room temperature. The precipitate is sucked, washed with a small amount of methanol and dried. 0.28 g of a yellow solid are obtained, which is combined with the residue.
  • Em10-s 0.50 g (0.42 mmol) of Em10-s are dissolved in 300 ml of acetonitril and irradiated with a mercury pressure dipping lamp TQ 150 (365 nm, 150 W) for 5.5 hours. The solution is freed from the solvent. The residue is dissolved in 30 ml of methanol by heating. After cooling the precipitate is sucked, washed with methanol and dried. The complex isomer Em10-i [0.19 g (38%)] is obtained as yellow powder melting at 316-317° C.
  • Structure B ITO-AJ20-1000-35 nm Ir(DPBIC) 3 mixed with 10 wt.-% MoO 3 -10 nm Ir(DPBIC) 3 -40 nm “MaX” mixed with 15 wt.-% Em1-i-10 nm LB1-20 nm electron conductor BCP-0.70 nm LiF-100 nm Al.
  • the preparation of the diode is carried out in analogy to Example 17.
  • the preparation of the diode is carried out in analogy to Example 17.
  • matrix material Ma10 is described in JP2009046408, compound B, [0039], p. 13.

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JP6015124B2 (ja) * 2011-05-18 2016-10-26 東ソー株式会社 カルベン化合物誘導体を構成成分とする有機薄膜電子デバイス
US8748012B2 (en) 2011-05-25 2014-06-10 Universal Display Corporation Host materials for OLED
EP3415521A1 (en) 2011-06-14 2018-12-19 UDC Ireland Limited Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in oleds
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
US8409729B2 (en) * 2011-07-28 2013-04-02 Universal Display Corporation Host materials for phosphorescent OLEDs
JP5742586B2 (ja) * 2011-08-25 2015-07-01 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
CN103917542B (zh) 2011-11-10 2018-03-27 Udc 爱尔兰有限责任公司 用于电子应用的4H‑咪唑并[1,2‑a]咪唑
EP2797941A1 (en) * 2011-12-28 2014-11-05 Solvay SA Preparation of heteroleptic metal complexes
KR102012047B1 (ko) 2012-01-06 2019-08-19 유니버셜 디스플레이 코포레이션 효율이 큰 인광 물질
JP5978843B2 (ja) 2012-02-02 2016-08-24 コニカミノルタ株式会社 イリジウム錯体化合物、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
JP6024744B2 (ja) * 2012-04-03 2016-11-16 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子
US9620724B2 (en) 2012-07-10 2017-04-11 Udc Ireland Limited Benzimidazo[1,2-A]benzimidazole derivatives for electronic applications
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
JP6217642B2 (ja) 2012-08-24 2017-10-25 コニカミノルタ株式会社 透明電極、電子デバイス、および透明電極の製造方法
JP6333262B2 (ja) 2012-09-20 2018-05-30 ユー・ディー・シー アイルランド リミテッド 電子用途のためのアザジベンゾフラン
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
KR102046153B1 (ko) * 2013-03-12 2019-12-02 삼성전자주식회사 유기 금속 착물, 이를 이용한 유기 전계 발광 소자 및 표시 장치
CN105051927B (zh) 2013-03-20 2020-10-16 Udc 爱尔兰有限责任公司 在oled中用作效率促进剂的氮杂苯并咪唑卡宾配体
EP2980878B1 (en) 2013-03-29 2019-05-01 Konica Minolta, Inc. Organic electroluminescent element, and lighting device and display device which are provided with same
KR101798307B1 (ko) 2013-03-29 2017-11-15 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자용 재료, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치
JP6048281B2 (ja) * 2013-03-29 2016-12-21 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
EP2991997B1 (en) 2013-04-29 2018-02-21 UDC Ireland Limited Transition metal complexes with carbene ligands and the use thereof in oleds
CN104183754A (zh) * 2013-05-22 2014-12-03 海洋王照明科技股份有限公司 有机电致发光器件及其制备方法
CN104183723A (zh) * 2013-05-22 2014-12-03 海洋王照明科技股份有限公司 有机电致发光器件及其制备方法
JP6506272B2 (ja) 2013-07-02 2019-04-24 ユー・ディー・シー アイルランド リミテッド 有機発光ダイオードにおいて使用するための一置換されたジアザベンゾイミダゾールカルベン金属錯体
EP2837634A1 (en) 2013-08-12 2015-02-18 Saudi Basic Industries Corporation Catalyst system for polymerisation of an olefin
WO2015063046A1 (en) 2013-10-31 2015-05-07 Basf Se Azadibenzothiophenes for electronic applications
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
DE102013225682A1 (de) 2013-12-12 2015-06-18 Friedrich-Alexander-Universität Erlangen-Nürnberg Metallionaddukte von neutralen phosphoreszenten Emittern zur Verwendung in lichtemittierenden organischen optoelektronischen Bauteilen
EP3084855B1 (en) 2013-12-20 2021-08-18 UDC Ireland Limited Highly efficient oled devices with very short decay times
CN106661068A (zh) 2014-03-31 2017-05-10 Udc 爱尔兰有限责任公司 包含具有o‑取代非环金属化芳基的碳烯配位体的金属络合物和其在有机发光二极管中的用途
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
WO2016016791A1 (en) 2014-07-28 2016-02-04 Idemitsu Kosan Co., Ltd (Ikc) 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds)
EP2982676B1 (en) 2014-08-07 2018-04-11 Idemitsu Kosan Co., Ltd. Benzimidazo[2,1-B]benzoxazoles for electronic applications
DE102014112618B4 (de) * 2014-09-02 2023-09-07 Pictiva Displays International Limited Organisches Licht emittierendes Bauelement
EP2993215B1 (en) 2014-09-04 2019-06-19 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles for electronic applications
KR102308117B1 (ko) 2014-10-17 2021-10-01 삼성전자주식회사 카바졸계 화합물 및 이를 포함한 유기 발광 소자
EP3015469B1 (en) 2014-10-30 2018-12-19 Idemitsu Kosan Co., Ltd. 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications
WO2016079667A1 (en) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Indole derivatives for electronic applications
EP3034507A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs)
EP3034506A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 4-functionalized carbazole derivatives for electronic applications
EP3053918B1 (en) 2015-02-06 2018-04-11 Idemitsu Kosan Co., Ltd. 2-carbazole substituted benzimidazoles for electronic applications
EP3054498B1 (en) 2015-02-06 2017-09-20 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
JP5831654B1 (ja) 2015-02-13 2015-12-09 コニカミノルタ株式会社 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
GB2535476A (en) * 2015-02-16 2016-08-24 Cambridge Display Tech Ltd Compound, composition and organic light-emitting device
EP3061759B1 (en) 2015-02-24 2019-12-25 Idemitsu Kosan Co., Ltd Nitrile substituted dibenzofurans
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
EP3070144B1 (en) 2015-03-17 2018-02-28 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
EP3072943B1 (en) 2015-03-26 2018-05-02 Idemitsu Kosan Co., Ltd. Dibenzofuran/carbazole-substituted benzonitriles
EP3075737B1 (en) 2015-03-31 2019-12-04 Idemitsu Kosan Co., Ltd Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
JP6662913B2 (ja) 2015-06-03 2020-03-11 ユー・ディー・シー アイルランド リミテッド 減衰時間がきわめて短く高度に効率的なｏｌｅｄデバイス
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US10672996B2 (en) 2015-09-03 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
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
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 (en) 2015-10-01 2019-08-14 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes
EP3150604B1 (en) 2015-10-01 2021-07-14 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
KR20180079328A (ko) 2015-11-04 2018-07-10 이데미쓰 고산 가부시키가이샤 벤즈이미다졸 축합 헤테로아릴
WO2017093958A1 (en) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes
JP6160685B2 (ja) * 2015-12-24 2017-07-12 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP6788314B2 (ja) 2016-01-06 2020-11-25 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置
US20170229663A1 (en) 2016-02-09 2017-08-10 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10968229B2 (en) 2016-04-12 2021-04-06 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US12317745B2 (en) 2016-11-09 2025-05-27 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US12098157B2 (en) 2017-06-23 2024-09-24 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US12180230B2 (en) 2017-11-28 2024-12-31 University Of Southern California Carbene compounds and organic electroluminescent devices
EP3492480B1 (en) 2017-11-29 2021-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11937503B2 (en) 2017-11-30 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
CN108191827A (zh) * 2018-02-09 2018-06-22 广东省石油与精细化工研究院 一种喹啉三唑类稀土配合物及其制备方法和应用
CN108586539B (zh) * 2018-04-13 2020-06-05 苏州科技大学 含二苯并噻吩环金属铱配合物及其作为有机电致发光器件发光层掺杂材料的应用
US20200075870A1 (en) 2018-08-22 2020-03-05 Universal Display Corporation Organic electroluminescent materials and devices
EP3850055A1 (en) 2018-09-12 2021-07-21 Merck Patent GmbH Materials for organic electroluminescent devices
TWI826522B (zh) 2018-09-12 2023-12-21 德商麥克專利有限公司 電致發光裝置
TW202030902A (zh) 2018-09-12 2020-08-16 德商麥克專利有限公司 電致發光裝置
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US20200251664A1 (en) 2019-02-01 2020-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US20220127286A1 (en) 2019-03-04 2022-04-28 Merck Patent Gmbh Ligands for nano-sized materials
JP2020158491A (ja) 2019-03-26 2020-10-01 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
KR102769410B1 (ko) 2019-04-11 2025-02-17 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 재료
US12281128B2 (en) 2019-07-30 2025-04-22 Universal Display Corporation Organic electroluminescent materials and devices
US12139501B2 (en) 2019-08-16 2024-11-12 Universal Display Corporation Organic electroluminescent materials and devices
US20210135130A1 (en) 2019-11-04 2021-05-06 Universal Display Corporation Organic electroluminescent materials and devices
US20230002416A1 (en) 2019-11-04 2023-01-05 Merck Patent Gmbh Materials for organic electroluminescent devices
TW202134252A (zh) 2019-11-12 2021-09-16 德商麥克專利有限公司 有機電致發光裝置用材料
TW202136181A (zh) 2019-12-04 2021-10-01 德商麥克專利有限公司 有機電致發光裝置用的材料
US20210217969A1 (en) 2020-01-06 2021-07-15 Universal Display Corporation Organic electroluminescent materials and devices
US20220336759A1 (en) 2020-01-28 2022-10-20 Universal Display Corporation Organic electroluminescent materials and devices
EP4097090A1 (de) 2020-01-29 2022-12-07 Merck Patent GmbH Benzimidazol-derivate
KR20220157456A (ko) 2020-03-23 2022-11-29 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 재료
EP3937268B1 (en) 2020-07-10 2025-05-07 Universal Display Corporation Plasmonic oleds and vertical dipole emitters
US20220158096A1 (en) 2020-11-16 2022-05-19 Universal Display Corporation Organic electroluminescent materials and devices
US20220165967A1 (en) 2020-11-24 2022-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US12325717B2 (en) 2020-11-24 2025-06-10 Universal Display Corporation Organic electroluminescent materials and devices
US20220271241A1 (en) 2021-02-03 2022-08-25 Universal Display Corporation Organic electroluminescent materials and devices
EP4060758A3 (en) 2021-02-26 2023-03-29 Universal Display Corporation Organic electroluminescent materials and devices
EP4059915A3 (en) 2021-02-26 2022-12-28 Universal Display Corporation Organic electroluminescent materials and devices
US20220298192A1 (en) 2021-03-05 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US20220298190A1 (en) 2021-03-12 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US20220298193A1 (en) 2021-03-15 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US20220340607A1 (en) 2021-04-05 2022-10-27 Universal Display Corporation Organic electroluminescent materials and devices
US20220352478A1 (en) 2021-04-14 2022-11-03 Universal Display Corporation Organic eletroluminescent materials and devices
US20220407020A1 (en) 2021-04-23 2022-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US20230006149A1 (en) 2021-04-23 2023-01-05 Universal Display Corporation Organic electroluminescent materials and devices
US20230133787A1 (en) 2021-06-08 2023-05-04 University Of Southern California Molecular Alignment of Homoleptic Iridium Phosphors
EP4151699A1 (en) 2021-09-17 2023-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US20240343970A1 (en) 2021-12-16 2024-10-17 Universal Display Corporation Organic electroluminescent materials and devices
EP4231804A3 (en) 2022-02-16 2023-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US20230292592A1 (en) 2022-03-09 2023-09-14 Universal Display Corporation Organic electroluminescent materials and devices
JP2023148087A (ja) 2022-03-30 2023-10-13 学校法人関西学院 金属錯体
US20230337516A1 (en) 2022-04-18 2023-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US20230389421A1 (en) 2022-05-24 2023-11-30 Universal Display Corporation Organic electroluminescent materials and devices
EP4293001A1 (en) 2022-06-08 2023-12-20 Universal Display Corporation Organic electroluminescent materials and devices
US20240016051A1 (en) 2022-06-28 2024-01-11 Universal Display Corporation Organic electroluminescent materials and devices
US20240107880A1 (en) 2022-08-17 2024-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US20240188419A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240180025A1 (en) 2022-10-27 2024-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US20240188319A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240196730A1 (en) 2022-10-27 2024-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US20240188316A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
KR20250110873A (ko) 2022-11-17 2025-07-21 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
US20240247017A1 (en) 2022-12-14 2024-07-25 Universal Display Corporation Organic electroluminescent materials and devices
CN115961298B (zh) * 2022-12-31 2024-10-01 广西师范大学 一种电化学介导乙烯基苯胺与醇合成2，3-二烷氧基取代吲哚啉化合物、合成方法及应用
US20250204238A1 (en) 2023-12-15 2025-06-19 Universal Display Corporation Organic electroluminscent materials and devices
US20250204239A1 (en) 2023-12-15 2025-06-19 Universal Display Corporation Organic electroluminescent materials and devices

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020086180A1 (en) * 2000-12-28 2002-07-04 Satoshi Seo Luminescent device
US20050260448A1 (en) * 2004-05-18 2005-11-24 Chun Lin Novel organometallic compounds for use in electroluminescent devices
US20050258433A1 (en) * 2004-05-18 2005-11-24 Entire Interest Carbene metal complexes as OLED materials
US20060246315A1 (en) * 2005-04-27 2006-11-02 Begley William J Phosphorescent oled with mixed electron transport materials
US20070190359A1 (en) * 2006-02-10 2007-08-16 Knowles David B Metal complexes of cyclometallated imidazo[1,2-ƒ]phenanthridine and diimidazo[1,2-a:1',2'-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US20080106188A1 (en) * 2006-11-08 2008-05-08 Seok-Hwan Hwang Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound
US20090017330A1 (en) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device utilizing the same
US20120012821A1 (en) * 2009-01-07 2012-01-19 Basf Se Silyl- and heteroatom-substituted compounds selected from carbazoles, dibenzofurans, dibenzothiophenes and dibenzophospholes, and use thereof in organic electronics
US8383828B2 (en) * 2006-04-04 2013-02-26 Basf Aktiengesellschaft Transition metal complexes comprising one noncarbene ligand and one or two carbene ligands and their use in OLEDs
US8692241B1 (en) * 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US9812656B2 (en) * 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices

Family Cites Families (83)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5984539A (en) 1997-11-06 1999-11-16 Eastman Kodak Company Method and apparatus of applying a solution of a predetermined viscosity to photosensitive material to form a protective coating thereon
EP1729327B2 (en) 1999-05-13 2022-08-10 The Trustees Of Princeton University Use of a phosphorescent iridium compound as emissive molecule in an organic light emitting device
JP3924648B2 (ja) 1999-11-02 2007-06-06 ソニー株式会社 有機電界発光素子
DE10104426A1 (de) 2001-02-01 2002-08-08 Covion Organic Semiconductors Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen
DE10338550A1 (de) 2003-08-19 2005-03-31 Basf Ag Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs)
WO2005113704A2 (en) 2004-05-18 2005-12-01 The University Of Southern California Luminescent compounds with carbene ligands
DE102004037451A1 (de) 2004-08-02 2006-03-16 Niels Raeder Verpackung, insbesondere Tüte, mit einem Informationsträger
DE102004057072A1 (de) 2004-11-25 2006-06-01 Basf Ag Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs)
US8492749B2 (en) 2004-12-23 2013-07-23 Basf Se Electroluminescent metal complexes with nucleophilic carbene ligands
US7902374B2 (en) 2005-05-06 2011-03-08 Universal Display Corporation Stability OLED materials and devices
US9051344B2 (en) * 2005-05-06 2015-06-09 Universal Display Corporation Stability OLED materials and devices
CN101184822B (zh) 2005-05-30 2014-11-26 西巴特殊化学品控股有限公司 电致发光器件
JP4935024B2 (ja) * 2005-08-25 2012-05-23 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、それを用いた表示装置および照明装置
US8148891B2 (en) * 2005-10-04 2012-04-03 Universal Display Corporation Electron impeding layer for high efficiency phosphorescent OLEDs
EP1786050B1 (de) 2005-11-10 2010-06-23 Novaled AG Dotiertes organisches Halbleitermaterial
DE102005058543A1 (de) 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
EP2463930B1 (en) 2006-01-05 2017-04-12 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
US20090091253A1 (en) 2006-03-17 2009-04-09 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
ES2310380T3 (es) 2006-03-21 2009-01-01 Novaled Ag Radical o dirradical heterociclicos, sus dimeros, oligomeros, polimeros, compuestos diespiro y policiclos, su utilizacion, material semiconductor organico asi como componente electronico.
JP5683784B2 (ja) * 2006-03-23 2015-03-11 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
US20070224446A1 (en) 2006-03-24 2007-09-27 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US7897962B2 (en) 2006-03-30 2011-03-01 Konica Minolta Holdings, Inc. Organic electroluminescence device, lighting device, and display having a reactive organic compound
JP5345519B2 (ja) 2006-04-05 2013-11-20 ビーエーエスエフ ソシエタス・ヨーロピア ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード（ｏｌｅｄ）において用いる使用
JP5055818B2 (ja) 2006-04-19 2012-10-24 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、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5298460B2 (ja) * 2006-06-08 2013-09-25 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置および照明装置
WO2008000727A1 (de) 2006-06-26 2008-01-03 Basf Se Verwendung von übergangsmetallcarbenkomplexen, die keine cyclometallierung über nicht-carbene enthalten, in oleds
JP2008021687A (ja) 2006-07-10 2008-01-31 Mitsubishi Chemicals Corp 有機電界発光素子用材料、有機電界発光素子用組成物及び有機電界発光素子
JP5332614B2 (ja) 2006-09-08 2013-11-06 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP5444715B2 (ja) 2006-09-08 2014-03-19 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP2008066569A (ja) 2006-09-08 2008-03-21 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2008035571A1 (en) 2006-09-20 2008-03-27 Konica Minolta Holdings, Inc. Organic electroluminescence element
KR101069302B1 (ko) 2006-09-21 2011-10-05 바스프 에스이 수명이 연장된 ｏｌｅｄ 디스플레이
JP5589251B2 (ja) 2006-09-21 2014-09-17 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子材料
JP5011908B2 (ja) 2006-09-26 2012-08-29 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、表示装置および照明装置
WO2008072596A1 (ja) 2006-12-13 2008-06-19 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、表示装置及び照明装置
GB0625540D0 (en) 2006-12-22 2007-01-31 Oled T Ltd Electroluminescent devices
JP5381103B2 (ja) 2007-01-23 2014-01-08 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子の製造方法、該製造方法により得られた有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2008207520A (ja) 2007-02-28 2008-09-11 Konica Minolta Holdings Inc 有機薄膜、有機薄膜の製造方法、電子デバイス、有機エレクトロルミネッセンス素子、表示装置及び照明装置
EP1988587B1 (de) 2007-04-30 2016-12-07 Novaled GmbH Oxokohlenstoff-, Pseudooxokohlenstoff- und Radialenverbindungen sowie deren Verwendung
WO2008140114A1 (ja) 2007-05-16 2008-11-20 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2008146838A1 (ja) 2007-05-30 2008-12-04 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2008156105A1 (ja) 2007-06-21 2008-12-24 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR101577465B1 (ko) * 2007-07-05 2015-12-14 바스프 에스이 카르벤 전이 금속 착체 이미터, 및 디실릴카르바졸, 디실릴디벤조푸란, 디실릴디벤조티오펜, 디실릴디벤조포스폴, 디실릴디벤조티오펜 ｓ-옥사이드 및 디실릴디벤조티오펜 ｓ,ｓ-디옥사이드로부터 선택된 1종 이상의 화합물을 포함하는 유기 발광 다이오드
JP5804703B2 (ja) 2007-07-05 2015-11-04 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ジシリルカルバゾール、ジシリルジベンゾフラン、ジシリルジベンゾチオフェン、ジシリルジベンゾホスホール、ジシリルジベンゾチオフェンｓ−オキシドおよびジシリルジベンゾチオフェンｓ，ｓ−ジオキシドから選択される少なくとも１つのジシリル化合物を含む有機発光ダイオード
JP5194596B2 (ja) 2007-07-11 2013-05-08 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、表示装置及び照明装置
FR2918892B1 (fr) 2007-07-16 2010-02-12 Fabre Pierre Dermo Cosmetique Composition dermatologique anti-inflammatoire comprenant des corticoides et des fragments de hyaluronate, et ses utilisations
JP2009046408A (ja) 2007-08-17 2009-03-05 Konica Minolta Holdings Inc ジハロ多環芳香族化合物、ピロリル多環芳香族化合物、及びそれらの製造方法
JP5186843B2 (ja) 2007-08-30 2013-04-24 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、照明装置及び表示装置
JP5194652B2 (ja) * 2007-09-03 2013-05-08 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、有機エレクトロルミネッセンス素子、表示装置及び照明装置
ATE554095T1 (de) 2007-10-17 2012-05-15 Basf Se Übergangsmetallkomplexe mit verbrückten carbenliganden und deren verwendung in oleds
WO2009060779A1 (ja) 2007-11-08 2009-05-14 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5458890B2 (ja) 2007-11-08 2014-04-02 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2009114370A (ja) 2007-11-08 2009-05-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子及び表示装置、照明装置
WO2009060780A1 (ja) 2007-11-08 2009-05-14 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2009060757A1 (ja) 2007-11-08 2009-05-14 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2009114369A (ja) 2007-11-08 2009-05-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2009063757A1 (ja) 2007-11-14 2009-05-22 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置
JP2009135183A (ja) 2007-11-29 2009-06-18 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
US20090153034A1 (en) 2007-12-13 2009-06-18 Universal Display Corporation Carbazole-containing materials in phosphorescent light emittinig diodes
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
WO2009084413A1 (ja) 2007-12-28 2009-07-09 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子、及び有機エレクトロルミネッセンス素子の製造方法
JP5549053B2 (ja) 2008-01-18 2014-07-16 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置
JP2009182298A (ja) 2008-02-01 2009-08-13 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP5381719B2 (ja) 2008-02-20 2014-01-08 コニカミノルタ株式会社 白色発光有機エレクトロルミネッセンス素子
JP2009267255A (ja) 2008-04-28 2009-11-12 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
EP2123733B1 (en) 2008-05-13 2013-07-24 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
JP5533652B2 (ja) 2008-07-01 2014-06-25 コニカミノルタ株式会社 白色発光有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2010004877A1 (ja) 2008-07-10 2010-01-14 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、表示装置及び照明装置
JP2010021336A (ja) 2008-07-10 2010-01-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP5338184B2 (ja) 2008-08-06 2013-11-13 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置、照明装置
KR101929837B1 (ko) 2008-10-07 2018-12-18 유디씨 아일랜드 리미티드 축합환계로 치환된 실롤 및 유기전자소자에서의 그 용도
WO2010044342A1 (ja) 2008-10-15 2010-04-22 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、有機エレクトロルミネッセンス素子の製造方法、白色有機エレクトロルミネッセンス素子、表示装置及び照明装置
EP2180029B1 (en) 2008-10-23 2011-07-27 Novaled AG Radialene compounds and their use
JP5493333B2 (ja) 2008-11-05 2014-05-14 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、白色有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5707665B2 (ja) 2008-12-03 2015-04-30 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置
WO2010067746A1 (ja) 2008-12-08 2010-06-17 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、表示装置、及び照明装置
WO2010079678A1 (ja) 2009-01-09 2010-07-15 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、表示装置及び照明装置
JP5472121B2 (ja) 2009-01-28 2014-04-16 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置および照明装置、ならびに有機エレクトロルミネッセンス素子の製造方法
WO2010090077A1 (ja) 2009-02-06 2010-08-12 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、該素子を備えた照明装置及び表示装置
WO2010095564A1 (ja) 2009-02-18 2010-08-26 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、該素子を備えた照明装置及び表示装置
CN102741265B (zh) * 2009-10-28 2015-12-09 巴斯夫欧洲公司 杂配卡宾配合物及其在有机电子品中的用途
US20110203649A1 (en) 2010-02-19 2011-08-25 Basf Se Use of indanthrene compounds in organic photovoltaics
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020086180A1 (en) * 2000-12-28 2002-07-04 Satoshi Seo Luminescent device
US20050260448A1 (en) * 2004-05-18 2005-11-24 Chun Lin Novel organometallic compounds for use in electroluminescent devices
US20050258433A1 (en) * 2004-05-18 2005-11-24 Entire Interest Carbene metal complexes as OLED materials
US20060246315A1 (en) * 2005-04-27 2006-11-02 Begley William J Phosphorescent oled with mixed electron transport materials
US20070190359A1 (en) * 2006-02-10 2007-08-16 Knowles David B Metal complexes of cyclometallated imidazo[1,2-ƒ]phenanthridine and diimidazo[1,2-a:1',2'-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US8383828B2 (en) * 2006-04-04 2013-02-26 Basf Aktiengesellschaft Transition metal complexes comprising one noncarbene ligand and one or two carbene ligands and their use in OLEDs
US20080106188A1 (en) * 2006-11-08 2008-05-08 Seok-Hwan Hwang Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound
US20090017330A1 (en) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device utilizing the same
US20120012821A1 (en) * 2009-01-07 2012-01-19 Basf Se Silyl- and heteroatom-substituted compounds selected from carbazoles, dibenzofurans, dibenzothiophenes and dibenzophospholes, and use thereof in organic electronics
US9812656B2 (en) * 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices
US9847495B2 (en) * 2011-06-08 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US8692241B1 (en) * 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Ma et al., "Organic light-emitting diodes based on new n-doped electron transport layer", Synthetic Metals 158, pp. 810-814 (2008). *

Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11839140B2 (en) 2009-12-14 2023-12-05 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDS
US11444254B2 (en) 2009-12-14 2022-09-13 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs
US10916716B2 (en) 2009-12-14 2021-02-09 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDS
US9487548B2 (en) 2009-12-14 2016-11-08 Udc Ireland Limited Metal complexes comprising diazabenzimidazolocarbene ligands and the use thereof in OLEDs
US10090476B2 (en) 2009-12-14 2018-10-02 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs
US9236535B2 (en) 2011-02-24 2016-01-12 Basf Se Illumination devices
US9711665B2 (en) 2011-05-10 2017-07-18 Basf Se Color converters
US9406894B2 (en) 2011-06-03 2016-08-02 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, organic light-emitting element, light-emitting device, electronic device, and lighting device
US11063229B2 (en) 2011-06-08 2021-07-13 Universal Display Corporation Organic electroluminescent materials and devices
US9755164B2 (en) * 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US9812656B2 (en) * 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices
US10297769B2 (en) 2011-06-08 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US20140175408A1 (en) * 2011-06-08 2014-06-26 Universal Display Corporation Heteroleptic iridium carbene complexes and light emitting device using them
US20180019414A1 (en) * 2011-06-08 2018-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US20140131687A1 (en) * 2011-06-08 2014-05-15 Universal Display Corporation Heteroleptic iridium carbene complexes and light emitting device using them
US10978648B2 (en) * 2011-06-08 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US9406848B2 (en) 2011-06-10 2016-08-02 Basf Se Color converter
US10230023B2 (en) 2011-06-10 2019-03-12 Basf Se Color converter
US9583719B2 (en) 2011-08-12 2017-02-28 Basf Se Carbazolocarbazol-bis(dicarboximides) and their use as semiconductors
JP2014101307A (ja) * 2012-11-20 2014-06-05 Konica Minolta Inc イリジウム錯体のフェイシャル体の製造方法
US10290817B2 (en) 2013-07-31 2019-05-14 Udc Ireland Limited Luminescent diaza-monoaza-and benzimidazole metal carbene complexes for use in electronic devices such as OLEDs
US9701773B2 (en) 2013-08-12 2017-07-11 Sabic Global Technologies, B.V. Catalyst system for polymerisation of an OLEFIN
US10033000B2 (en) 2013-11-15 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9873753B2 (en) 2013-12-20 2018-01-23 Saudi Basic Industries Corporation Catalyst system for polymerization of an olefin
US10727423B2 (en) * 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US11114624B2 (en) 2016-06-20 2021-09-07 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) * 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
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US12171139B2 (en) 2016-06-20 2024-12-17 Universal Display Corporation Organic electroluminescent materials and devices
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US12101999B2 (en) 2016-06-20 2024-09-24 Universal Display Corporation Organic electroluminescent materials and devices
US11690284B2 (en) 2016-06-20 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
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US10651403B2 (en) * 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
US20170373259A1 (en) * 2016-06-20 2017-12-28 Universal Display Corporation Organic Electroluminescent Materials and Devices
JP2017200929A (ja) * 2017-06-05 2017-11-09 コニカミノルタ株式会社 イリジウム錯体のフェイシャル体の製造方法
US11038138B2 (en) 2017-08-11 2021-06-15 Lg Chem, Ltd. Organic electroluminescent device and method for manufacturing the same
CN111587494A (zh) * 2017-12-20 2020-08-25 诺瓦尔德股份有限公司 包含反配位络合物的有机电子器件及其制备方法
GB2569635A (en) * 2017-12-21 2019-06-26 Sumitomo Chemical Co Compound
US11856845B2 (en) 2017-12-21 2023-12-26 Sumitomo Chemical Company Limited Compound
US11165028B2 (en) * 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US20190334100A1 (en) * 2018-04-27 2019-10-31 Samsung Display Co., Ltd. Organometallic compound and organic light-emitting device including the same
US12232409B2 (en) * 2018-04-27 2025-02-18 Samsung Display Co., Ltd. Organometallic compound and organic light-emitting device including the same
US12187748B2 (en) 2020-11-02 2025-01-07 Universal Display Corporation Organic electroluminescent materials and devices

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