EP3028318A1 - Elektrooptische vorrichtung und deren verwendung - Google Patents

Elektrooptische vorrichtung und deren verwendung

Info

Publication number
EP3028318A1
EP3028318A1 EP14733092.2A EP14733092A EP3028318A1 EP 3028318 A1 EP3028318 A1 EP 3028318A1 EP 14733092 A EP14733092 A EP 14733092A EP 3028318 A1 EP3028318 A1 EP 3028318A1
Authority
EP
European Patent Office
Prior art keywords
emitter
electro
group
optical device
emitter layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP14733092.2A
Other languages
German (de)
English (en)
French (fr)
Inventor
Susanne Heun
Aurélie LUDEMANN
Junyou Pan
Niels Schulte
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to EP14733092.2A priority Critical patent/EP3028318A1/de
Publication of EP3028318A1 publication Critical patent/EP3028318A1/de
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/411—Suzuki reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/95—Use in organic luminescent diodes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1483—Heterocyclic containing nitrogen and sulfur as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent 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]
    • H10K50/11—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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • 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]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a novel design principle for organic, electro-optical devices, in particular for electroluminescent elements and their use in based on displays and lighting means.
  • light-sensitive organic materials e.g., phthalocyanines
  • organic charge transport materials e.g., triarylamine-based hole transport materials
  • OLED organic light-emitting diodes
  • multicolor display elements such as in pocket calculators,
  • PLED polymeric OLED
  • SMOLED vapor deposited small molecule devices
  • interlayer in a layer structure, such as in WO 04 / 084260 A, the lifetime and efficiency of PLED have been significantly increased, and these interlayers are deposited between the anode and the layer of light-emitting polymers, with the function of injecting and transporting holes, ie positively charged carriers, into the light-emitting To facilitate polymer or
  • intermediate layers consist of polymers with a high proportion of hole-transporting units linked by a conjugated backbone. These polymers also block the transport of electrons at the same time.
  • Interlayer is applied by ink jet printing or by spin coating. The thickness of this layer is adjusted so that the layer does not completely dissolve again in the subsequent step.
  • Carrying out a crosslinking step can be produced if emitters are used in addition to the emitter layer in the intermediate layer. This allows the simple generation of multicolor OLED in which at least two different emitter layers can be processed from solution.
  • the present invention has the object to provide an electro-optical device which can be produced with simple application methods from solution, which has a plurality of emitters and which has a longer service life compared to known devices.
  • the subject of the present invention is thus an electro-optical device containing
  • At least one first emitter layer which is arranged between the anode and the cathode, comprising at least one semiconductive, organic material
  • the emitters of the second emitter layer and the intermediate layer, respectively are selected to have a lowest unoccupied molecular orbital ("LUMO") higher than the LUMO of the semiconducting organic material of the first
  • the LUMO of the emitter of the intermediate layer is preferably 0.1 eV, and particularly preferably 0.2 eV, higher than the LUMO of the first emitter layer.
  • HOMO Highest Occupied Molecular Orbital
  • LUMO Low Unoccupied Molecular Orbital
  • the energy levels of the molecular orbitals can also be determined by quantum chemical calculation methods, e.g. through the "Density Function
  • the emitter is integrated as a repeating unit in a polymer.
  • the emitter is mixed into a matrix material, which may be a small molecule, a polymer, an oligomer, a dendrimer or a mixture thereof.
  • emitter layer containing at least one emitter selected from fluorescent compounds, phosphorescent compounds and emitting organometallic complexes.
  • emitter unit or emitter in the present application refers to a unit or compound in which, upon receipt of an exciton or formation of an exciton, radiation decay occurs with light emission.
  • emitters There are two classes of emitters, fluorescent and phosphorescent
  • fluorescent emitter refers to materials or compounds that have a radiation transition from an excited one Experience singlet state to its ground state.
  • phosphorescent emitter as used in the present application refers to luminescent materials or compounds containing transition metals. These typically include materials in which the light emission is caused by spin-forbidden transitions, eg, transitions of excited triplet and / or transitions
  • the transition from excited states with high spin multiplicity e.g. of excited triplet states, forbidden to the ground state.
  • a heavy atom such as iridium, osmium, platinum and europium
  • the excited singlet and triplet are mixed so that the triplet acquires a certain singlet character, and if the singlet-triplet mixture results in a radiation decay rate faster than the non-radiative event, the luminance can be efficient.
  • This type of emission can be achieved with metal complexes, as Baldo et al. in Nature 395, 151-154 (1998).
  • an emitter selected from the group of fluorescent emitters.
  • fluorescent emitters e.g. Styrylamine derivatives in JP 2913116 B and WO 2001/021729 A1, as well as Indenofluorenderivate in WO 2008/006449 and the
  • the fluorescent emitters are preferably polyaromatic compounds, such as 9,10-di (2-naphthylanthracene) and other anthracene derivatives, derivatives of tetracene, xanthene, perylene, such as 2,5,8,11-tetracenes.
  • t-butylperylene phenylene, eg 4,4 '- (bis (9-ethyl-3-carbons) azovinylene) -1, r-biphenyl, fluorene, arylpyrene (US 2006/0222886), arylenevinylenes (US 5121029, US 5130603), derivatives of rubrene, coumarin, rhodamine, quinacridone, such as ⁇ , ⁇ '-dimethylquinacridone (DMQA), dicyano-methylene-pyran, such as, for example, 4- (dicyanoethylene) -6- (4-dimethylaminostyryl-2-methyl) -4H-pyran (DCM), thiopyrans, polymethine, pyrylium and thiopyrylium salts, periflanthene, indenoperylene, Bis (azinyl) imineboron compounds (US 2007/0092753 A1), bis (aziny
  • Suitable fluorescent emitters are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines.
  • a monostyrylamine is meant a compound containing a substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
  • a distyrylamine is meant a compound which is two substituted or unsubstituted
  • Styryl groups and at least one, preferably aromatic, amine are to be understood as meaning a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tetrastyrylamine is meant a compound containing four substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • the styryl groups are particularly preferably stilbenes, which may also be further substituted.
  • the corresponding phosphines and ethers are defined analogously to the amines.
  • the present application is under an aryl amine or a
  • aromatic amine to understand a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems which are directly bonded to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, preferably having at least 14 aromatic ring atoms. Preferred examples of these are aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic
  • aromatic anthracenamine is a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • aromatic anthracenediamine is meant a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups being attached to the pyrene preferably in the 1-position or in the 1, 6-position.
  • Other preferred fluorescent emitters are indenofluorenamines and indenofluorodiamines, e.g. according to WO 2006/122630, benzoin-indenofluoreneamines and benzoindenofluorodiamines, e.g. according to WO 2008/006449, and dibenzoindenofluorenamines and dibenzoindeno-fluoro-diamines, e.g. according to WO 2007/140847.
  • Examples of emitters from the class of styrylamines are substituted or unsubstituted tristilbenamines or the dopants described in WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549 and WO 2007/115610.
  • Distyrylbenzene and distyryl biphenyl derivatives are described in US 5121029.
  • Other styrylamines can be found in US 2007/0122656 A1.
  • Particularly preferred styrylamine emitters and triarylamine emitters are the compounds of the formulas (1) to (6) as described in US Pat. No. 7,250,532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US Pat
  • fluorescent emitters are selected from the group of tri-aryl amines, such as e.g. in EP 1957606 A1 and the
  • fluorescent emitters are from the derivatives of naphthalene, anthracene, tetracene, fluorene, periflanthene, indenoperylene, phenanthrene, perylene (US 2007/0252517 A1), pyrene, chrysene, decacycles, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirobifluorene, Rubrene, coumarin (US 4769292, US 6020078, US 2007/0252517 A1), pyran, oxazone, benzoxazole, benzothiazole, benzimidazole, pyrazine, cinnamic acid esters, diketopyrrolopyrrole, acridone and quinacridone (US 2007/0252517 A1).
  • anthracene compounds 9,10-substituted anthracenes such as 9,10-diphenylanthracene and 9,10-bis (phenylethynyl) anthracene are particularly preferred. 1,4-bis (9'-ethynylanthracenyl) benzene is also a preferred dopant.
  • an emitter in the emitter layer is selected from the group of blue-fluorescent emitters.
  • an emitter in the emitter layer is selected from the group of green-fluorescing emitters.
  • an emitter in the emitter layer is selected from the group of yellow-fluorescing emitters.
  • an emitter in the emitter layer is selected from the group of red-fluorescent emitters.
  • a red-fluorescent emitter is preferably selected from the group of perylene derivatives, for example in the following structure of the formula (7), as disclosed, for example, in US 2007/0104977 A1.
  • Preferred emissive repeat units are those selected from the following formulas:
  • Ar 1 independently of one another is a mono- or polycyclic aryl or heteroaryl group which, if appropriate, is monosubstituted or polysubstituted by radicals R 11 ,
  • Ar 12 is independently a mono- or polycyclic aryl or heteroaryl group, which is optionally mono- or polysubstituted by radicals R 12 ,
  • Ar 13 is independently of one another a mono- or polycyclic aryl or heteroaryl group which is optionally mono- or polysubstituted by radicals R 13 ,
  • Ar 14 is independently of one another a mono- or polycyclic aryl or heteroaryl group which is optionally mono- or polysubstituted by radicals R 14 ,
  • R 11 , R 12 and R 13 may also mean a covalent bond in a polymer
  • X °, R ° and R 00 have one of the meanings defined in formula (I), i is independently 1, 2 or 3,
  • k is independently 1, 2 or 3,
  • o is independently 0 or 1.
  • R 1 and R 2 have the meaning defined for formula (I) and Ar has one of the meaning defined for Ar 11 in formula (I).
  • emitting repeat units are 1,4-bis (2-arylenevinyl) benzenes of the formula (III), as disclosed, for example, in WO 00/46321 A: wherein r and R are as defined above and u is 0 or 1.
  • X 21 is O, S, SO 2 C (R X ) 2 or NR x , in which R x is aryl or substituted aryl or aralkyl having 6 to 40 C atoms, or alkyl having 1 to 24 C atoms, preferably aryl 6 to 24 C atoms, particularly preferably alkylated aryl having 6 to 24 C atoms,
  • Ar 21 is optionally substituted aryl or heteroaryl having 6 to 40, preferably 6 to 24, particularly preferably 6 to 14 C atoms.
  • X 22 R 23 C CR 23 or S, in which each R 23 is independently selected from the group consisting of hydrogen, alkyl, aryl, perfluoroalkyl, thioalkyl, cyano, alkoxy, heteroaryl, alkylaryl or arylalkyl,
  • R 21 and R 22 are the same or different and each one
  • Ar 22 and Ar 23 independently represent a divalent aromatic or heteroaromatic ring system having 2 to 40 carbon atoms, which is optionally substituted by one or more radicals R 21 , and a1 and b1 are independently 0 or 1.
  • X 23 is NH, O or S.
  • Ph is phenyl
  • an emitter in the emitter layer which is selected from the group of phosphorescent emitters.
  • Examples of phosphorescent emitters are disclosed in WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614 and WO 2005/033244.
  • the phosphorescent emitter may be a metal complex, preferably of the formula M (L) Z in which M is a metal atom, L on each occurrence independently represents an organic ligand attached to M via one, two or more positions or is coordinated thereto, and z is an integer> 1, preferably 1, 2, 3, 4, 5 or 6, and in which optionally these groups with a polymer over one or more, preferably one, two or three Positions, preferably via the ligands L, are linked.
  • M is a metal atom selected from transition metals, preferably from Group VIII transition metals, lanthanides or actinides, more preferably Rh, Os, Ir, Pt, Pd, Au, Sm, Eu, Gd, Tb , Dy, Re, Cu, Zn, W, Mo, Pd, Ag or Ru, and in particular is selected from Os, Ir, Ru, Rh, Re, Pd or Pt.
  • M can also mean Zn.
  • Preferred ligands are 2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives or 2-phenylquinoline derivatives. These compounds may each be substituted, e.g. by fluorine or trifluoromethyl substituents for blue.
  • Secondary ligands are preferably acetylacetonate or picric acid.
  • complexes of trivalent lanthanides such as Tb 3+ and Eu 3+ (Kido, KJ et al., Appl., Phys., Lett., 65, 2124, Kido, et al., Chem., Lett., 657, 1990, US Pat 2007/0252517 A1) or phosphorescent complexes of Pt (II), Ir (I), Rh (I) with maleonitrile dithiolate (Johnson et al., JACS 105, 1983, 1795), Re (I) tricarbonyldiimine complexes (inter alia Wrighton , JACS 96, 1974, 998), Os (II) complexes with cyano ligands and bipyridyl or phenanthroline ligands (Ma et al., Synth. Metals 94, 1998, 245) or Alq 3 .
  • trivalent lanthanides such as Tb 3+ and Eu 3+
  • Particularly preferred phosphorescent emitters are compounds of the following formulas (9) and (10) as well as further compounds such as e.g. in US 2001/0053462 A1 and WO 2007/095118 A1.
  • an emitter in the emitter layer selected from the group of organometallic complexes.
  • a suitable metal complex according to the present invention are selected from transition metals, rare earth elements, lanthanides and actinides.
  • the metal is selected from Ir, Ru, Os, Eu, Au, Pt, Cu, Zn, Mo, W, Rh, Pd and Ag.
  • the proportion of emitter structural units in the hole-conducting polymer used in the intermediate layer is generally between 0.01 and 20 mol%, preferably between 0.5 and 10 mol%, particularly preferably between 1 and 8 mol%, and in particular between 1 and 5 mol%.
  • copolymers containing the intermediate layer i. the second
  • Form emitter layer must have hole-conducting properties.
  • This property profile can be selected by selecting appropriate
  • repeating units having hole transport properties can be generated.
  • the polymer of the intermediate layer has further repeating units which form the polymer backbone.
  • HTM hole transport material
  • HTM hole transport material
  • Such HTM is preferably selected from amines, triarylamines, thiophenes, carbazoles, phthalocyanines, porphyrins and their isomers and
  • the HTM is more preferably selected from amines, triarylamines, thiophenes, carbazoles, phthalocyanines and porphyrins.
  • Suitable HTM units are phenylenediamine derivatives (US 3615404), arylamine derivatives (US 3567450), amino-substituted chalcone derivatives (US 3526501), styrylanthracene derivatives (JP A 56-46234), polycyclic aromatic compounds (EP 009041), polyarylalkane derivatives (US 3615402), fluorenone derivatives (JP A 54-110837), hydrazone derivatives (US 3717462), stilbene derivatives (JP A 61-2 0363), silazane derivatives (US 4950950), polysilanes (JP A 2-204996), aniline copolymers (JP A 2-282263), Thiophene oligomers, polythiophenes, PVK, polypyrroles, polyanilines and other copolymers, porphyrin compounds (JP A 63-2956965), aromatic dimethylidene-type compounds, carbazole compounds such as CDBP, CBP,
  • aromatic tertiary amines containing at least two tertiary amine units e.g. 4,4-bis- [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD) (US 5061569) or
  • triarylamine compounds of formulas (11) to (16) which may also be substituted, e.g. in EP 1162193 A1, EP 650955 A1, in Synth. Metals 1997, 91 (1-3), 209, in DE 19646119 A1, WO 2006/122630 A1, EP 1860097 A1, EP 1834945 A1, JP 08/053397 A, US 6251531 B1 and the
  • WO 2009/041635 discloses.
  • HTM units are, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, carbazole, azulene, thiophene, pyrrole and furan derivatives, and also O, S or N-containing heterocycles.
  • HTM units are as follows
  • Ar 1 which may be the same or different, independently when in different repeating units, represents a single bond or an optionally substituted mononuclear or polynuclear aryl group
  • Ar 2 which may be the same or different, independently, if in different repeating units, an optionally substituted one mononuclear or polynuclear aryl group
  • Ar 3 which may be the same or different, independently when in different repeating units, represents an optionally substituted mononuclear or polynuclear aryl group
  • n 1, 2 or 3.
  • Particularly preferred units of the formula (17) are selected from the group of the following formulas (18) to (20).
  • R which may be the same or different at each occurrence, is selected from H, sub ⁇ stituted or unsubstituted, aromatic or heteroaromatic group, alkyl group, cycloalkyl group, alkoxy group, aralkyl group, aryloxy group, arylthio group, alkoxycarbonyl group, silyl group, carboxyl group, halogen atom, cyano group, nitro group, or
  • r 0, 1, 2, 3 or 4 and
  • Another preferred interlayer polymer contains at least one repeating unit of the following formula (21)
  • T and T 2 are independently selected from thiophene, selenophene, thieno [2,3b] thiophene, thieno [3,2b] thiophene, dithienothiophene, pyrrole, aniline, all of which are optionally substituted with R 5 ,
  • R ° and R 00 are independently H or an optionally substi tuted ⁇ carbyl or hydrocarbyl, optionally containing one or more hetero atoms,
  • Ar 4 and Ar 5 independently of each other mononuclear or polynuclear aryl or heteroaryl which is optionally substituted and is optionally ⁇ Pol fused to the 2,3-positions of one or both of the adjacent thiophene or Selenophen phenomenon,
  • c and e independently represent 0, 1, 2, 3 or 4, wherein
  • d and f independently represent 0, 1, 2, 3 or 4.
  • the groups T 1 and T 2 are preferably selected from Thiophene-2,5-diyl,
  • R ° and R 5 can assume the same meanings as R ° and R 5 in formula (21).
  • Preferred units of formula (21) are selected from the group of the following formulas:
  • R ° can assume the same meanings as R 5 in formula (21).
  • the proportion of the HTM repeat units in the hole-conducting polymer used in the intermediate layer is preferably between 0 and 99 mol%, particularly preferably between 20 and 80 mol%, and in particular between 30 and 60 mol%.
  • the copolymers used in the intermediate layer preferably have further structural units, which form the backbone of the copolymer.
  • repeating units which form the polymer backbone are aromatic or heteroaromatic structures having 6 to 40 carbon atoms. These are, for example, 4,5-dihydropyrene derivatives, 4,5,9,10-tetrahydropyrene derivatives, fluorine derivatives as disclosed, for example, in US Pat. No.
  • repeating units for the polymer backbone are repeating units of the following formula (22)
  • X means halogen
  • R ° and R 00 independently of one another denote H or an optionally substituted carbyl or hydrocarbyl group which optionally contains one or more heteroatoms
  • each g is independently 0 or 1 and the corresponding h in the same subunit is for the other of 0 or 1,
  • Ar 1 and Ar 2 are independently mono- or polynuclear aryl or heteroaryl optionally substituted and optionally fused to the 7,8-positions or 8,9-positions of the indenofluorene group, and
  • a and b independently represent 0 or 1.
  • R 1 and R 2 form a spiro group with the fluorene group to which they are attached, these are preferably spirobifluorene.
  • the group of the formula (22) is preferably selected from the following formulas (23) to (27)
  • the group of formula (22) is more preferably selected from the following formulas (28) to (31)
  • L is H, halogen or optionally fluorinated, linear or branched alkyl or alkoxy having 1 to 12 C atoms and preferably H, F, methyl, i-propyl, t-butyl, n-pentoxy or trifluoromethyl and
  • L ' is optionally fluorinated, linear or branched alkyl or alkoxy having 1 to 12 C atoms and preferably n-octyl or n-octyloxy.
  • the polymer of the intermediate layer is a non-conjugated or partially conjugated polymer.
  • a particularly preferred nonconjugated or partially conjugated polymer of the intermediate layer contains a non-conjugated repeat unit for the polymer backbone.
  • the unconjugated repeating unit for the polymer backbone unit is preferably an indenofluorene unit represented by the following formulas (32) and (33), such as e.g. disclosed in WO 2010/136110.
  • X and Y are independently selected from the group consisting of H, F, a a C 2- 4o-alkenyl group, a C2 -4 o- alkynyl group, an optionally substituted C 6- 4o-aryl group and an optionally substituted 5- to 25-membered consists heteroaryl group.
  • non-conjugated repeating units for the polymer backbone are selected from fluorene, phenanthrene,
  • R1-R4 may take the same meanings as X and Y in the formulas (32) and (33).
  • the proportion of repeat units in the hole-conducting polymer used in the intermediate layer, the polymer backbone is preferably between 10 and 99 mol%, particularly preferably between 20 and 80 mol%, and in particular between 30 and 60 mol%.
  • the semiconducting organic material for the first emitter layer may be a polymeric matrix material incorporating one or more different emitters incorporated in the polymer, which may be a polymeric and non-emissive matrix material into which one or more low molecular weight emitters are intermixed may be mixtures of different polymers with im
  • the emitter layer contains a conjugated polymer containing at least one repeating unit containing an emitter group as described above.
  • metal complex-containing conjugated polymers and their synthesis are described in e.g. in EP 1138746 B1 and DE 102004032527 A1.
  • singlet emitter-containing conjugated polymers and their synthesis are described e.g. in DE 102005060473 A1 and WO 2010/022847. ⁇
  • the emitter layer contains a non-conjugated polymer containing at least one emitter group as described above and at least one pendant charge transport group.
  • non-conjugated polymers containing a pendent metal complex and their synthesis are disclosed, for example, in US7250226 B2, JP 2007/21 1243 A2, JP 2007/197574 A2, US 7250226 B2 and JP 2007/059939 A.
  • not Conjugated polymers containing a pendant singlet emitter and their synthesis are disclosed, for example, in JP 2005/108556, JP 2005/285661 and JP 2003/338375.
  • the emitter layer contains a non-conjugated polymer which has at least one emitter group as described above as a repeating unit and at least one
  • Repeating unit forming the polymer backbone in the main chain, wherein the repeating units constituting the polymer backbone may be preferably selected from the non-conjugated polymer backbone repeat units described above for the interlayer polymer.
  • Examples of non-conjugated polymers containing a metal complex in the main chain and their synthesis are described e.g. in WO 2010/149261 and WO 2010/136110.
  • a material used for the emitter layer contains, in addition to the emitter (s), a charge-transporting polymer matrix.
  • this polymer matrix may be selected from a conjugated polymer which preferably contains a non-conjugated polymer backbone as described above for the interlayer polymer, and most preferably a conjugated polymer backbone as described above for the interlayer polymer.
  • this polymer matrix is preferably selected from non-conjugated polymers which are a non-conjugated side-chain polymer or non-conjugated backbone polymer, eg, polyvinylcarbazole ("PVK”), polysilane, copolymers containing phosphine oxide units, or the like Matrix polymers as described, for example, in WO 2010/149261 and WO 2010/1361 0.
  • the emitter layer contains at least one low molecular weight emitter having a
  • Suitable low molecular weight matrix materials are materials from various classes.
  • Preferred matrix materials for fluorescent or singlet emitters are selected from the classes of the oligoarylenes (for example 2,2 ', 7,7'-tetraphenyl-spirobifluorene according to EP 676461 or dinaphthylanthracene),
  • Oligoarylenes e.g. Phenanthrene, tetracene, coronene, chrysene, fluorene, spirobifluorene, perylene, phthaloperylene, naphthaloperylene, decacyclene, rubrene, the oligoarylenevinylenes (eg 4,4'-bis (2,2-diphenylethenyl) -1, 1'-biphenyl (DPVBi) or 4,4-bis-2,2-diphenylvinyl-1, 1-spirobiphenyl (spiro-DPVBi) according to EP 676461), the polypodal metal complexes (eg.
  • metal complexes of 8-hydroxyquinoline for example aluminum (III) tris (8-hydroxyquinoline) (aluminum quinolate, Alq 3 ) or bis (2-methyl-8-quinolinolato) -4- ( phenylphenol-linolato) aluminum, also with imidazole chelate (US 2007/0092753 A1) and quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline-metal complexes, the hole-conducting compounds (eg according to the
  • WO 04/058911 the electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (for example according to WO 05/084081 and WO 05/084082), the atropisomers (for example according to the
  • Particularly preferred host materials are from the classes of
  • Very particularly preferred host materials are from the classes of oligoarylenes containing anthracene, Benzanthracene and / or pyrene, or atropisomers of these compounds selected.
  • an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.
  • Particularly preferred low molecular weight matrix materials for singlet emitters are selected from benzanthracene, anthracene, triarylamine, indenofluorene, fluorene, spirobifluorene, phenanthrene, dihydrophenanthrene and their isomers and derivatives.
  • Preferred low molecular weight matrix materials for phosphorescent or triplet emitters are ⁇ , ⁇ -biscarbazolylbiphenyl (CBP),
  • Carbazole derivatives for example according to WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 and DE 102007002714),
  • Azacarbazoles for example according to EP 1617710, EP 1617711, the
  • ketones e.g.
  • WO 04/093207 phosphine oxides, sulfoxides and sulfones (e.g., according to WO 05/003253), oligophenylenes, aromatic amines (e.g., according to US 2005/0069729), bipolar matrix materials (e.g.
  • WO 07/137725 1,3,5-triazine derivatives (for example according to US Pat. No. 6,229,012 B1, US Pat. No. 6,225,467 B1, DE 10312675 A1, WO 9804007 A1 and US Pat. No. 6352791 B1), silanes (for example according to WO 05 / 111172), 9,9-diaryl fluorene derivatives (eg according to DE 102008017591), azaboroles or
  • Boronic acid esters for example according to WO 06/117052
  • triazole derivatives for example according to WO 06/117052
  • oxazoles and oxazole derivatives for example, imidazole derivatives, polyarylalkane derivatives,
  • Particularly preferred low molecular weight matrix materials for triplet emitters are selected from carbazole, ketone, triazine, imidazole, fluorene, spirobifluorene, phenanthrene, dihydrophenanthrene and their isomers and derivatives.
  • Another preferred material used for the first emitter layer includes, in addition to the emitter (s), a neutral polymer matrix, e.g. Polystyrene (PS), polymethyl methacrylate (PMMA), polyvinyl butyral (PVB) or polycarbonate (PC).
  • a neutral polymer matrix e.g. Polystyrene (PS), polymethyl methacrylate (PMMA), polyvinyl butyral (PVB) or polycarbonate (PC).
  • a preferred material used for the construction of the first emitter layer contains, in addition to the emitter or emitters, a material with electron-transporting properties (ETM).
  • ETM can be contained either as a repeating unit in the polymer or as a separate compound in the first emitter layer.
  • ETM electron transport material
  • Triarylboranen and their isomers and derivatives are Suitable ETM materials are metal chelates of 8-hydroxyquinoline (for example, Liq, Alq 3, Gaq 3, MgQ 2, ZnQ 2, lnq 3, Zrq), Balq, 4-Azaphenanthren-5-ol / loading complexes (US 5,529,853 A; eg formula 7), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), benzazoles, such as
  • phenanthrolines e.g. BCP and Bphen
  • phenanthrolines bonded via biphenyl or other aromatic groups e.g. BCP and Bphen
  • phenanthrolines bonded to anthracene e.g. BCP and Bphen
  • 1, 3,4-oxadiazoles eg.
  • Formula 11 triazoles, e.g. Formula 12, triarylboranes, benzimidazole derivatives and other N-heterocyclic compounds (US 2007/0273272 A1), silacyclopentadiene derivatives, borane derivatives, Ga-oxinoid complexes.
  • a preferred ETM unit is selected from units having a
  • the ETM unit has the structure of the following formula (34):
  • ETM units fluorene, spirobifluorene or indenofluoro ketones which are selected from the following formulas (35) to (37):
  • R and R 1 "8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic cyclic hydrocarbon group having 6 to 50 carbon atoms in the nucleus, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms in the nucleus, a substituted or unsubstituted one Alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms in the nucleus, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms in the nucleus, a substituted or unsubstituted arylthio group having 5 to 50 carbon atoms in the nucleus, a substituted or unsub
  • ETM repeating units are selected from the group consisting of imidazole derivatives or benzoimidazole derivatives, e.g. in US 2007 / 0104977A1.
  • R is a hydrogen atom, a C 6-60 aryl group which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, a C 1-20 alkyl group which may have a substituent, or a C 1-6 alkyl group which may have a substituent C1-20 alkoxy group which may have a substituent;
  • m is an integer from 0 to 4;
  • R 1 is a C 6-60 aryl group which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, a C 1-20 alkyl group which may have a substituent, or a C 1-6 alkyl group which may have a substituent C1-20 aikoxy group which may have a substituent;
  • R 2 is a hydrogen atom, a C 6-60 aryl group which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, a C 1-20 alkyl group which may have a substituent, or a C 1-20 alkoxy group which may have a substituent;
  • l is a C 6-60 arylene group which may have a substituent, a pyridinylene group which may have a substituent, a quinoline group which may have a substituent, or a fluorenylene group which may have a substituent, and
  • Ar 1 represents a C 6-60 aryl group which may have a substituent, a pyridinyl group which may have a substituent, or a quinolinyl group which may have a substituent. Further preferred are 2,9,10-substituted anthracenes (with 1- or 2-naphthyl and 4- or 3-biphenyl) or molecules containing two anthracene units, as disclosed, for example, in US 2008/0193796 A1.
  • N-heteroaromatic ring systems of the following formulas (39) to (44).
  • anthracene benzimidazole derivatives of the following formulas (45) to (47), as described e.g. in US 6878469 B2, the
  • polymers containing an ETM repeating unit and their synthesis are disclosed, for example, in US 2003/0170490 A1 for triazine as ETM repeating unit.
  • Preferred as structural units with electron-transporting properties for the first emission layer are units which differ from
  • benzophenone triazine, imidazole, benzoimidazole and perylene units, which may be optionally substituted. Particular preference is given to benzophenone, aryltriazine, benzoimidazole and diarylperylene units.
  • ETM repeat units or ETM compounds which comprise structural units having electron-conducting properties which are selected from the structural units of the following formulas (48) to (51),
  • R 1 to R 4 can assume the same meaning as R in formula (36).
  • the proportion of structural units having electron-conducting properties in the polymer which is used in the first emitter layer is preferably between 0.01 and 30 mol%, particularly preferably between 1 and 20 mol%, and in particular between 10 and 20 mol%.
  • the first emitter layer is a polymeric matrix material that incorporates one or more different emitters incorporated in the polymer backbone, or mixtures of polymers
  • Matrix materials wherein the polymers incorporated in the polymer backbone contain one or more different emitters.
  • the emitters in the emitter layers are preferably selected so that the widest possible emission results.
  • triplet emitters are combined with the following emissions: green and red; blue and green; light blue and light red; blue, green and red.
  • triplet emitters with deep green and deep red emission are particularly preferably used. This can be adjusted especially yellow tones well. By varying the concentrations of the individual emitters, the hues can be generated and adjusted in the desired manner.
  • the term "visible spectrum” is understood to mean the wavelength range from 380 nm to 750 nm.
  • electroluminescent devices in which a first emitter has an emission maximum in the green spectral range and a second emitter has an emission maximum in the red spectral range.
  • emitters are those which have their emission maximum in the blue and green spectral range, in the light blue and bright red spectral range or in blue, green and red
  • electro-optical devices in which at least two triplet emitters are present, each one
  • the first triplet emitter is in the first emission layer and the second one
  • Triplet emitter arranged in the intermediate layer.
  • electro-optical devices in which the first triplet emitter has an emission maximum in the light blue spectral range and the second triplet emitter has an emission maximum in the yellow spectral range.
  • electro-optical devices in which at least one singlet emitter is present, which has an emission maximum in the green, red or blue spectral range.
  • the emitters are present in the emitter layers in a dopant-matrix system.
  • the concentration of the emitter (s) is preferably in the range from 0.01% to 30 mol%, particularly preferably in the range from 1 to 25 mol%, and in particular in the range from 2 to 20 mol%.
  • the first emitter layer contains electron-transporting substances.
  • the electro-optical device according to the invention in the first emitter layer and / or in the second emitter layer contains substances which promote the transfer of excitation energy into the triplet state. These are, for example, carbazoles, ketones, phosphine oxides, silanes, sulfoxides,
  • the organic semiconductor in the first emitter layer is a semiconducting polymer, preferably a semiconductive copolymer.
  • the organic semiconducting polymer preferably has
  • Copolymers have further repeating units derived from triarylamines, preferably those having repeating units of the following formulas (52) to (54).
  • R which may be the same or different at each occurrence, from H, substituted or unsubstituted aromatic or heteroaromatic group, alkyl group, cycloalkyl group, alkoxy group, aralkyl group, aryloxy group, arylthio group, alkoxycarbonyl group, silyl group, carboxy group, halogen atom, cyano group, nitro group or
  • r 0, 1, 2, 3 or 4 and
  • s 0, 1, 2, 3, 4 or 5.
  • the eiektrooptica devices according to the invention particularly preferably have the simplest possible structure.
  • this may be a device which, in addition to a cathode and anode layer, has only two or more interposed therebetween
  • ektroktroptica device comprises at least one additional
  • Electron injection layer which is disposed directly between the first emission layer and the cathode.
  • the electro-optical device according to the invention is preferably applied to a substrate, preferably to a transparent substrate,
  • an electrode of transparent or semi-transparent material is preferably applied.
  • ITO indium tin oxide
  • the electro-optical device according to the invention has a third emission layer.
  • This third emission layer preferably contains at least one
  • low molecular weight emitter which can be selected from the groups of emitters described above, and at least one
  • the first and second emission layers are processed from solution, and the third emission layer is evaporated in vacuo.
  • the first, second and third emission layers emit red, green and blue light, the light intensity of the individual layers being adjusted such that a total of white emission results.
  • the electro-optical device according to the invention consists only of anode, buffer layer, e.g. containing PANI or PEDOT, hole injection layer, two emitter layers, hole blocking layer, electron transport layer and cathode, optionally built on a transparent substrate.
  • the electro-optic device further comprises a hole injection layer disposed between the anode and intermediate layer of hole-conducting polymer, preferably a layer of poly (ethylenedioxothiophene) (PEDOT).
  • PEDOT poly (ethylenedioxothiophene)
  • the electro-optical devices according to the invention have
  • thicknesses of the separated individual layers in the range from 1 to 150 nm, particularly preferably in the range from 3 to 100 nm, and in particular in the range from 5 to 80 nm.
  • Preferred electro-optical devices according to the invention contain polymeric materials having glass transition temperatures T g greater than 90 ° C, more preferably greater than 100 ° C, and most preferably greater than 120 ° C.
  • cathode materials materials known per se can be used in the electro-optical devices according to the invention. Especially for OLEDs, materials with a low work function are used. Examples are metals, metal combinations or
  • Low work function metal alloys such as e.g. Ca, Sr, Ba, Cs, Mg, Al, In and Mg / Ag.
  • the structure of the devices according to the invention can be with
  • Printing processes within the meaning of the present application also include those which emanate from the solid, such as thermal transfer or LITI.
  • solvents which dissolve the substances used.
  • the nature of the substance is not relevant to the present invention.
  • the preparation of the electro-optical device according to the invention can thus be carried out according to known methods, wherein at least the two emitter layers are applied from solution, preferably by printing method, particularly preferably by ink jet printing.
  • the electro-optical device is an organic light-emitting device (OLED).
  • OLED organic light-emitting device
  • the OLEC has two electrodes, at least one emission layer and an intermediate layer between the emission layer and an electrode as described above, wherein the emission layer has at least one ionic compound.
  • the principle of OLEC is described in Qibing Pei et al., Science, 1995, 269, 1086-1088.
  • the inventive electro-optical device can be in
  • electro-optical devices according to the invention are particularly preferred in displays, as
  • Another preferred field of application of the electro-optical devices according to the invention relates to use in the cosmetic and therapeutic field, as disclosed, for example, in EP 1444008 and GB 2408092. These uses are also the subject of the present application.
  • the following examples illustrate the invention without limiting it.
  • interlayers As interlayers according to the invention, it is possible to use all hole-dominated polymers which additionally contain an emitter whose LUMO lies below the lowest LUMO of the other interlayer building blocks and of the preceding layer.
  • the use of interlayers in organic light emitting diodes is described e.g. disclosed in WO 2004/084260.
  • Typical interlayer polymers are disclosed in WO 2004/041901, but virtually all used in PLEDs,
  • conjugated or partially conjugated polymers by the incorporation of large amounts of hole-conducting units (typically triarylamines) in
  • Interlayer polymers are transferred.
  • Each of these interlayers can be converted into an interlayer according to the invention by the incorporation of emitters which can be polymerized or doped.
  • PLED polymeric organic light-emitting diodes
  • ITO structure indium-tin-oxide, a transparent, conductive anode
  • Sodalimeglas that result in the vapor-deposited at the end of the manufacturing process cathode 4 pixels x 2 x 2 mm.
  • PEDOT is a polythiophene derivative (C! Evios P 4083 AI) of HC Starck, Goslar, which is supplied as an aqueous dispersion) applied by spin coating.
  • the required spin rate depends on
  • the substrates are baked for 10 minutes at 180 ° C on a hot plate. Thereafter, under an inert gas atmosphere (nitrogen or argon), 20 nm of an interlayer are spun first.
  • these are the polymers P1 to P 0, which are processed at a concentration of 5 g / l of toluene. All interlayers of these device examples are baked under inert gas for 1 hour at 180 ° C. Subsequently, 65 nm of the polymer layers are applied from toluene solutions (typical concentrations 8 to 12 g / l). Similarly, soluble small molecules can be used, but then because of the low viscosity of the solutions in higher
  • Concentration must be set. Typical are 20 to 28 mg / ml. It has also proven advantageous to use a layer thickness of 80 nm here.
  • this second solubilized layer the main emission layer (“EML”), is also spin-coated and then baked under inert gas for 10 minutes at 180 ° C. Thereafter, the Ba / Al cathode is deposited in the
  • vapor-deposited by means of a vapor deposition mask high-purity metals from Aldrich, especially barium 99.99% (Order No. 474711);
  • Vaporiser systems from Lesker oa, typical vacuum level 5 x 10 ⁇ 6 mbar).
  • the device is finally encapsulated.
  • the encapsulation of the device takes place by gluing a commercially available coverslip over the pixelized surface. Subsequently, the device is characterized. For this, the devices are made specifically for the substrate size
  • a photodiode with eyelet filter can be placed directly on the measuring holder to exclude the influence of extraneous light.
  • the voltages are from 0 to max. 20 V in 0.2 V increments and lowered again. For each measurement point, the current through the device and the photocurrent obtained by the photodiode is measured. In this way you get the IVL data of the
  • Test Devices Important parameters are the measured maximum efficiency ("Max. Eff.” In cd / A) and the voltage required for 100 cd / m 2 .
  • the voltage required for 100 cd / m 2 is again applied after the first measurement and the photodiode is replaced by a spectrum measuring head. This is connected by an optical fiber with a spectrometer (Ocean Optics).
  • the color coordinates from the measured spectrum (CIE: Commission International de l'eclairage, standard observer from 1931) can be derived.
  • the life of the devices is measured in one of the initial evaluation very similar measurement setup so that an initial luminance is set (for example, 1000 cd / m 2).
  • the current required for this luminance is kept constant, while typically the voltage increases and the luminance decreases.
  • the lifetime is reached when the initial luminance has dropped to 50% of the initial value, which is why this value is also called LT 50 (from English "lifetime")
  • Example 11 If one has determined an extrapolation factor, the lifetimes can also be measured accelerated by setting a higher initial luminance. In this case, the measuring apparatus keeps the current constant so that it shows the electrical degradation of the components in a voltage increase.
  • Example 11 If one has determined an extrapolation factor, the lifetimes can also be measured accelerated by setting a higher initial luminance. In this case, the measuring apparatus keeps the current constant so that it shows the electrical degradation of the components in a voltage increase.
  • a first, unoptimized two-color white with cool white color coordinates is created by combining the interlayer P2 with the blue one
  • FIG. 3 shows the spectrum of the pure triplet green on HIL-012 and the
  • White components for lighting applications can also be improved with the help of the self-luminous interlayer.
  • a color tuning towards increasingly red white light is possible, for example, cultural
  • Examples 15 to 18 show the results for solubilized OLEDs in the structure of Figure 1, using as EML a white polymer which is synthesized without a red emitter (SPW-110 from Merck;
  • FIG. 4 again shows the EL spectrum of the device with HIL-012 from Merck and the spectra with the interlayer polymers P1 to P4 according to the invention.
  • OLEDs according to the invention are produced here,
  • the green interlayer has the additional advantage of also strengthening the red component in the spectrum, because without built - in green
  • Examples 24 to 26 therefore show the results of OLEDs with the white Merck polymer SPW-106, which is processed for comparison on the colorless interlayer HIL-012, as well as on the interlayers P9 and P10.
  • FIGS. 7 and 8 show the EL spectra. It is good to see, especially in the magnification, that the light blue emitter of the interlayer is responsible for the blue emission. Thus blue emission can also be obtained from the interlayer.
  • luminescent interlayer polymers in devices intended to emit white light.
  • the interlayer P2 is coated as usual, above that a blue EML polymer (SPB-036 as in Example 11) is processed and a green triplet EML is evaporated (TEG-001 in TMM-038).
  • SPB-036 blue EML polymer
  • TMG-001 in TMM-0308 green triplet EML is evaporated
  • the device structure is shown in FIG.
  • the white EL spectrum containing all the color components is shown in FIG.
  • the quantum efficiency of the device is 10% EQE, though largely

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Planar Illumination Modules (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
EP14733092.2A 2013-07-29 2014-06-26 Elektrooptische vorrichtung und deren verwendung Ceased EP3028318A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14733092.2A EP3028318A1 (de) 2013-07-29 2014-06-26 Elektrooptische vorrichtung und deren verwendung

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13003770 2013-07-29
PCT/EP2014/001738 WO2015014427A1 (de) 2013-07-29 2014-06-26 Elektrooptische vorrichtung und deren verwendung
EP14733092.2A EP3028318A1 (de) 2013-07-29 2014-06-26 Elektrooptische vorrichtung und deren verwendung

Publications (1)

Publication Number Publication Date
EP3028318A1 true EP3028318A1 (de) 2016-06-08

Family

ID=48915802

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14733092.2A Ceased EP3028318A1 (de) 2013-07-29 2014-06-26 Elektrooptische vorrichtung und deren verwendung

Country Status (6)

Country Link
US (1) US20160163987A1 (zh)
EP (1) EP3028318A1 (zh)
JP (2) JP2016525781A (zh)
KR (1) KR102238849B1 (zh)
CN (1) CN105409022B (zh)
WO (1) WO2015014427A1 (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108140741B (zh) * 2015-10-06 2020-05-15 住友化学株式会社 发光元件
EP3457449A4 (en) * 2016-05-10 2020-01-22 Hitachi Chemical Company, Ltd. CHARGE TRANSPORTATION MATERIAL, ORGANIC ELECTRONIC ELEMENT, AND ORGANIC ELECTROLUMINESCENT ELEMENT
KR20210056432A (ko) * 2018-09-24 2021-05-18 메르크 파텐트 게엠베하 과립형 재료의 제조 방법

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110315963A1 (en) * 2010-06-24 2011-12-29 Sony Corporation Organic el display and method of manufacturing the same
WO2012089294A1 (de) * 2010-12-28 2012-07-05 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen

Family Cites Families (156)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL250330A (zh) 1959-04-09
US3526501A (en) 1967-02-03 1970-09-01 Eastman Kodak Co 4-diarylamino-substituted chalcone containing photoconductive compositions for use in electrophotography
US3567450A (en) 1968-02-20 1971-03-02 Eastman Kodak Co Photoconductive elements containing substituted triarylamine photoconductors
US3615404A (en) 1968-04-25 1971-10-26 Scott Paper Co 1 3-phenylenediamine containing photoconductive materials
US3717462A (en) 1969-07-28 1973-02-20 Canon Kk Heat treatment of an electrophotographic photosensitive member
BE756943A (fr) 1969-10-01 1971-03-16 Eastman Kodak Co Nouvelles compositions photoconductrices et produits les contenant, utilisables notamment en electrophotographie
US4127412A (en) 1975-12-09 1978-11-28 Eastman Kodak Company Photoconductive compositions and elements
JPS54110837A (en) 1978-02-17 1979-08-30 Ricoh Co Ltd Electrophotographic photoreceptor
JPS5646234A (en) 1979-09-21 1981-04-27 Ricoh Co Ltd Electrophotographic receptor
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
JPS61210363A (ja) 1985-03-15 1986-09-18 Canon Inc 電子写真感光体
US4720432A (en) 1987-02-11 1988-01-19 Eastman Kodak Company Electroluminescent device with organic luminescent medium
US4769292A (en) 1987-03-02 1988-09-06 Eastman Kodak Company Electroluminescent device with modified thin film luminescent zone
JPS63256965A (ja) 1987-04-15 1988-10-24 Canon Inc 静電荷像現像用トナ−
US5121029A (en) 1987-12-11 1992-06-09 Idemitsu Kosan Co., Ltd. Electroluminescence device having an organic electroluminescent element
JPH02282263A (ja) 1988-12-09 1990-11-19 Nippon Oil Co Ltd ホール輸送材料
JP2727620B2 (ja) 1989-02-01 1998-03-11 日本電気株式会社 有機薄膜ｅｌ素子
US5130603A (en) 1989-03-20 1992-07-14 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US4950950A (en) 1989-05-18 1990-08-21 Eastman Kodak Company Electroluminescent device with silazane-containing luminescent zone
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
JP2913116B2 (ja) 1990-11-20 1999-06-28 株式会社リコー 電界発光素子
JP3016896B2 (ja) 1991-04-08 2000-03-06 パイオニア株式会社 有機エレクトロルミネッセンス素子
US5529853A (en) 1993-03-17 1996-06-25 Sanyo Electric Co., Ltd. Organic electroluminescent element
JP3295088B2 (ja) 1993-09-29 2002-06-24 出光興産株式会社 有機エレクトロルミネッセンス素子
DE69412567T2 (de) 1993-11-01 1999-02-04 Hodogaya Chemical Co., Ltd., Tokio/Tokyo Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung
EP0676461B1 (de) 1994-04-07 2002-08-14 Covion Organic Semiconductors GmbH Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien
JP2686418B2 (ja) 1994-08-12 1997-12-08 東洋インキ製造株式会社 ジアリールアミン誘導体、その製造方法及び用途
US5708130A (en) 1995-07-28 1998-01-13 The Dow Chemical Company 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers
EP0765106B1 (en) 1995-09-25 2002-11-27 Toyo Ink Manufacturing Co., Ltd. Light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted
DE19628719B4 (de) 1996-07-17 2006-10-05 Hans-Werner Prof. Dr. Schmidt Elektronenleitende Schicht in organischen, elektrolumineszierenden Anordnungen
US5766779A (en) 1996-08-20 1998-06-16 Eastman Kodak Company Electron transporting materials for organic electroluminescent devices
DE19646119A1 (de) 1996-11-08 1998-05-14 Hoechst Ag Elektrolumineszenzvorrichtung
GB9805476D0 (en) * 1998-03-13 1998-05-13 Cambridge Display Tech Ltd Electroluminescent devices
US6830828B2 (en) 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6229012B1 (en) 1998-10-01 2001-05-08 Xerox Corporation Triazine compositions
US6361886B2 (en) 1998-12-09 2002-03-26 Eastman Kodak Company Electroluminescent device with improved hole transport layer
US6020078A (en) 1998-12-18 2000-02-01 Eastman Kodak Company Green organic electroluminescent devices
KR100663052B1 (ko) 1999-02-04 2007-01-02 다우 글로벌 테크놀로지스 인크. 플루오렌 공중합체 및 이로부터 제조된 디바이스
EP1449238B1 (en) 1999-05-13 2006-11-02 The Trustees Of Princeton University Very high efficiency organic light emitting devices based on electrophosphorescence
US6534199B1 (en) 1999-09-21 2003-03-18 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and organic light emitting medium
EP3379591A1 (en) 1999-12-01 2018-09-26 The Trustees of Princeton University Complexes of form l2mx
JP4876311B2 (ja) 2000-01-14 2012-02-15 東レ株式会社 発光素子
US6225467B1 (en) 2000-01-21 2001-05-01 Xerox Corporation Electroluminescent (EL) devices
US6660410B2 (en) 2000-03-27 2003-12-09 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
DE60103442T3 (de) 2000-03-31 2014-05-15 Sumitomo Chemical Co. Ltd. Polymerisches fluoreszentes Material, Verfahren zu ihrer Herstellung, und lumineszentes Polymergerät worin es eingesetzt wird
JP4048521B2 (ja) 2000-05-02 2008-02-20 富士フイルム株式会社 発光素子
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
CN102041001B (zh) 2000-08-11 2014-10-22 普林斯顿大学理事会 有机金属化合物和发射转换有机电致磷光
JP4154138B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子、表示装置及び金属配位化合物
JP4154139B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 金属配位化合物
WO2002043449A1 (fr) 2000-11-24 2002-05-30 Toray Industries, Inc. Materiau luminescent et element luminescent contenant celui-ci
US20040082813A1 (en) 2001-03-16 2004-04-29 Toshihiro Iwakuma Method for producting aromatic amino compound
JP4629643B2 (ja) 2001-08-31 2011-02-09 日本放送協会 有機発光素子及び表示装置
US7250226B2 (en) 2001-08-31 2007-07-31 Nippon Hoso Kyokai Phosphorescent compound, a phosphorescent composition and an organic light-emitting device
DE10143353A1 (de) 2001-09-04 2003-03-20 Covion Organic Semiconductors Konjugierte Polymere enthaltend Spirobifluoren-Einheiten und deren Verwendung
JP2003115387A (ja) 2001-10-04 2003-04-18 Junji Kido 有機発光素子及びその製造方法
US6835469B2 (en) 2001-10-17 2004-12-28 The University Of Southern California Phosphorescent compounds and devices comprising the same
GB0127581D0 (en) 2001-11-17 2002-01-09 Univ St Andrews Therapeutic Light-emitting device
DE10159946A1 (de) 2001-12-06 2003-06-18 Covion Organic Semiconductors Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen
KR100691543B1 (ko) 2002-01-18 2007-03-09 주식회사 엘지화학 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자
US6730417B2 (en) 2002-01-29 2004-05-04 Xerox Corporation Organic electroluminescent (EL) devices
JP2003253145A (ja) 2002-02-28 2003-09-10 Jsr Corp 発光性組成物
JP4256182B2 (ja) 2002-03-14 2009-04-22 Ｔｄｋ株式会社 有機ｅｌ素子
SG128438A1 (en) 2002-03-15 2007-01-30 Sumitomo Chemical Co Polymer compound and polymer light emitting deviceusing the same
JP4274403B2 (ja) 2002-03-25 2009-06-10 大日本印刷株式会社 蛍光発光色素材料
WO2003099901A1 (fr) 2002-05-28 2003-12-04 Sumitomo Chemical Company, Limited Polymere et element luminescent polymere contenant ce polymere
ITRM20020411A1 (it) 2002-08-01 2004-02-02 Univ Roma La Sapienza Derivati dello spirobifluorene, loro preparazione e loro uso.
EP1551206A4 (en) 2002-10-09 2007-12-05 Idemitsu Kosan Co ORGANIC ELECTROLUMINESCENCE ELEMENT
DE10249723A1 (de) 2002-10-25 2004-05-06 Covion Organic Semiconductors Gmbh Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung
GB0226010D0 (en) 2002-11-08 2002-12-18 Cambridge Display Tech Ltd Polymers for use in organic electroluminescent devices
JP2004200162A (ja) 2002-12-05 2004-07-15 Toray Ind Inc 発光素子
CN100489056C (zh) 2002-12-23 2009-05-20 默克专利有限公司 有机电致发光元件
DE10310887A1 (de) 2003-03-11 2004-09-30 Covion Organic Semiconductors Gmbh Matallkomplexe
EP2174933B1 (en) 2003-03-13 2019-04-03 Idemitsu Kosan Co., Ltd. Benzimidazole derivatives for use in organic electroluminescent devices
JP4411851B2 (ja) 2003-03-19 2010-02-10 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
GB0306409D0 (en) 2003-03-20 2003-04-23 Cambridge Display Tech Ltd Electroluminescent device
JP2004311184A (ja) 2003-04-04 2004-11-04 Junji Kido 多核型フェナントロリン誘導体よりなる電子輸送材料、電荷制御材料およびそれを用いた有機発光素子
KR20040089567A (ko) 2003-04-14 2004-10-21 가부시키가이샤 도요다 지도숏키 자외선의 생성을 억제하는 유기 전계발광소자 및 이 유기전계발광소자를 가진 조명 시스템
EP2281861A3 (de) 2003-04-15 2012-03-28 Merck Patent GmbH Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese Mischungen
WO2004095889A1 (ja) 2003-04-23 2004-11-04 Konica Minolta Holdings, Inc. 有機エレクトロルミネッセンス素子及び表示装置
EP1478032A2 (en) 2003-05-16 2004-11-17 Kabushiki Kaisha Toyota Jidoshokki Light emitting diode method for forming the same
JP2004349138A (ja) 2003-05-23 2004-12-09 Toyota Industries Corp 有機電界発光素子及びその製造方法
EP1491568A1 (en) 2003-06-23 2004-12-29 Covion Organic Semiconductors GmbH Semiconductive Polymers
US8592614B2 (en) 2003-07-07 2013-11-26 Merck Patent Gmbh Mixtures of organic emissive semiconductors and matrix materials, their use and electronic components comprising said materials
DE10337346A1 (de) 2003-08-12 2005-03-31 Covion Organic Semiconductors Gmbh Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung
DE10343606A1 (de) 2003-09-20 2005-04-14 Covion Organic Semiconductors Gmbh Weiß emittierende Copolymere, deren Darstellung und Verwendung
JP2005108556A (ja) 2003-09-29 2005-04-21 Tdk Corp 有機ｅｌ素子及び有機ｅｌディスプレイ
DE10345572A1 (de) 2003-09-29 2005-05-19 Covion Organic Semiconductors Gmbh Metallkomplexe
US7795801B2 (en) 2003-09-30 2010-09-14 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
DE112004001856T5 (de) 2003-10-01 2006-07-27 Sumitomo Chemical Co., Ltd. Lichtemittierendes Polymermaterial und lichtemittierende polymere Vorrichtung
GB2408092A (en) 2003-11-13 2005-05-18 Ahad Ramezanpour A heat exchanger
US7029766B2 (en) 2003-12-05 2006-04-18 Eastman Kodak Company Organic element for electroluminescent devices
US6824895B1 (en) 2003-12-05 2004-11-30 Eastman Kodak Company Electroluminescent device containing organometallic compound with tridentate ligand
TW200530373A (en) 2003-12-12 2005-09-16 Sumitomo Chemical Co Polymer and light-emitting element using said polymer
DE102004008304A1 (de) 2004-02-20 2005-09-08 Covion Organic Semiconductors Gmbh Organische elektronische Vorrichtungen
JP4466160B2 (ja) 2004-03-30 2010-05-26 Ｔｄｋ株式会社 有機ｅｌ素子及び有機ｅｌディスプレイ
US7790890B2 (en) 2004-03-31 2010-09-07 Konica Minolta Holdings, Inc. Organic electroluminescence element material, organic electroluminescence element, display device and illumination device
DE102004020298A1 (de) 2004-04-26 2005-11-10 Covion Organic Semiconductors Gmbh Elektrolumineszierende Polymere und deren Verwendung
DE102004023277A1 (de) 2004-05-11 2005-12-01 Covion Organic Semiconductors Gmbh Neue Materialmischungen für die Elektrolumineszenz
JP4862248B2 (ja) 2004-06-04 2012-01-25 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
CN100368363C (zh) 2004-06-04 2008-02-13 友达光电股份有限公司 蒽化合物以及包括此蒽化合物的有机电致发光装置
TW200613515A (en) 2004-06-26 2006-05-01 Merck Patent Gmbh Compounds for organic electronic devices
DE102004031000A1 (de) 2004-06-26 2006-01-12 Covion Organic Semiconductors Gmbh Organische Elektrolumineszenzvorrichtungen
DE102004032527A1 (de) 2004-07-06 2006-02-02 Covion Organic Semiconductors Gmbh Elektrolumineszierende Polymere
GB0422391D0 (en) * 2004-10-08 2004-11-10 Cambridge Display Tech Ltd Light emitting device
US20060094859A1 (en) 2004-11-03 2006-05-04 Marrocco Matthew L Iii Class of bridged biphenylene polymers
EP1655359A1 (de) 2004-11-06 2006-05-10 Covion Organic Semiconductors GmbH Organische Elektrolumineszenzvorrichtung
TW200639140A (en) 2004-12-01 2006-11-16 Merck Patent Gmbh Compounds for organic electronic devices
TW200639193A (en) 2004-12-18 2006-11-16 Merck Patent Gmbh Electroluminescent polymers and their use
US9179518B2 (en) * 2004-12-24 2015-11-03 Cambridge Display Technology Limited Light emissive device
KR20100106626A (ko) 2005-01-05 2010-10-01 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 이를 이용한 유기 전기발광 소자
KR100803125B1 (ko) 2005-03-08 2008-02-14 엘지전자 주식회사 적색 인광 화합물 및 이를 사용한 유기전계발광소자
JP4263700B2 (ja) 2005-03-15 2009-05-13 出光興産株式会社 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
EP1860097B1 (en) 2005-03-18 2011-08-10 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device utilizing the same
US20060222886A1 (en) 2005-04-04 2006-10-05 Raymond Kwong Arylpyrene compounds
CN101184789B (zh) 2005-04-28 2012-05-30 住友化学株式会社 高分子化合物及使用了它的高分子发光元件
CN103204996B (zh) 2005-05-03 2015-12-09 默克专利有限公司 有机电致发光器件
DE102005023437A1 (de) 2005-05-20 2006-11-30 Merck Patent Gmbh Verbindungen für organische elektronische Vorrichtungen
WO2007043495A1 (ja) 2005-10-07 2007-04-19 Sumitomo Chemical Company, Limited 共重合体およびそれを用いた高分子発光素子
US7588839B2 (en) 2005-10-19 2009-09-15 Eastman Kodak Company Electroluminescent device
US20070092755A1 (en) 2005-10-26 2007-04-26 Eastman Kodak Company Organic element for low voltage electroluminescent devices
US20070092753A1 (en) 2005-10-26 2007-04-26 Eastman Kodak Company Organic element for low voltage electroluminescent devices
US20070104977A1 (en) 2005-11-07 2007-05-10 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US7553558B2 (en) 2005-11-30 2009-06-30 Eastman Kodak Company Electroluminescent device containing an anthracene derivative
DE102005058543A1 (de) 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102005058557A1 (de) 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
US7709105B2 (en) 2005-12-14 2010-05-04 Global Oled Technology Llc Electroluminescent host material
DE102005060473A1 (de) 2005-12-17 2007-06-28 Merck Patent Gmbh Konjugierte Polymere, deren Darstellung und Verwendung
DE102006003710A1 (de) 2006-01-26 2007-08-02 Merck Patent Gmbh Elektrolumineszierende Materialien und deren Verwendung
JP4879591B2 (ja) 2006-01-26 2012-02-22 昭和電工株式会社 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置
EP2399922B1 (en) 2006-02-10 2019-06-26 Universal Display Corporation Metal complexes of cyclometallated imidazo(1,2-f) phenanthridine and diimidazo(1,2-A;1',2'-C)quinazoline ligands and isoelectronic and benzannulated analogs therof
DE102006006412A1 (de) * 2006-02-13 2007-08-16 Merck Patent Gmbh Elektronisches Bauteil, Verfahren zu dessen Herstellung und dessen Verwendung
DE102006015183A1 (de) 2006-04-01 2007-10-04 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
JP4995475B2 (ja) 2006-04-03 2012-08-08 出光興産株式会社 ベンズアントラセン誘導体、及びそれを用いた有機エレクトロルミネッセンス素子
US20070252517A1 (en) 2006-04-27 2007-11-01 Eastman Kodak Company Electroluminescent device including an anthracene derivative
DE102006025777A1 (de) 2006-05-31 2007-12-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102006025846A1 (de) 2006-06-02 2007-12-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102006031990A1 (de) 2006-07-11 2008-01-17 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
WO2008011953A1 (en) * 2006-07-25 2008-01-31 Merck Patent Gmbh Polymer blends and their use in organic light emitting devices
JP2008124156A (ja) 2006-11-09 2008-05-29 Idemitsu Kosan Co Ltd 有機ｅｌ材料含有溶液、有機ｅｌ材料の薄膜形成方法、有機ｅｌ材料の薄膜、有機ｅｌ素子
JP5294872B2 (ja) 2006-11-20 2013-09-18 出光興産株式会社 有機エレクトロルミネッセンス素子
DE102007002714A1 (de) 2007-01-18 2008-07-31 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
JP4902381B2 (ja) 2007-02-07 2012-03-21 昭和電工株式会社 重合性化合物の重合体
DE102007024850A1 (de) 2007-05-29 2008-12-04 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
US7645142B2 (en) 2007-09-05 2010-01-12 Vivant Medical, Inc. Electrical receptacle assembly
JPWO2009041635A1 (ja) 2007-09-28 2011-01-27 出光興産株式会社 有機ｅｌ素子
DE102008017591A1 (de) 2008-04-07 2009-10-08 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008044868A1 (de) 2008-08-29 2010-03-04 Merck Patent Gmbh Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE102009023156A1 (de) 2009-05-29 2010-12-02 Merck Patent Gmbh Polymere, die substituierte Indenofluorenderivate als Struktureinheit enthalten, Verfahren zu deren Herstellung sowie deren Verwendung
DE102009023154A1 (de) 2009-05-29 2011-06-16 Merck Patent Gmbh Zusammensetzung, enthaltend mindestens eine Emitterverbindung und mindestens ein Polymer mit konjugationsunterbrechenden Einheiten
DE102009030848A1 (de) 2009-06-26 2011-02-03 Merck Patent Gmbh Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends
DE102011104745A1 (de) 2011-06-17 2012-12-20 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
GB201113563D0 (en) * 2011-08-05 2011-09-21 Cambridge Display Tech Ltd Light emitting polymers and devices
JP6570834B2 (ja) * 2011-12-12 2019-09-04 メルク パテント ゲーエムベーハー 電子素子のための化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110315963A1 (en) * 2010-06-24 2011-12-29 Sony Corporation Organic el display and method of manufacturing the same
WO2012089294A1 (de) * 2010-12-28 2012-07-05 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2015014427A1 *

Also Published As

Publication number Publication date
KR102238849B1 (ko) 2021-04-09
JP2016525781A (ja) 2016-08-25
WO2015014427A1 (de) 2015-02-05
US20160163987A1 (en) 2016-06-09
JP6848033B2 (ja) 2021-03-24
CN105409022B (zh) 2018-06-19
JP2020053395A (ja) 2020-04-02
CN105409022A (zh) 2016-03-16
KR20160040243A (ko) 2016-04-12

Similar Documents

Publication Publication Date Title
EP2462203B1 (en) Electronic devices comprising multi cyclic hydrocarbons
CN107690720B (zh) 作为用于oled制剂的溶剂的含有非芳族环的酯
EP3189551B1 (de) Formulierungen und verfahren zur herstellung einer organischen elektrolumineszenzvorrichtung
EP3532566B1 (en) Formulation of an organic functional material
EP3028319A1 (de) Elekrolumineszenzvorrichtung
KR102570137B1 (ko) 실록산 용매를 포함하는 유기 기능성 재료의 제형
WO2013060411A1 (de) Hyperverzweigte polymere, verfahren zu deren herstellung sowie deren verwendung in elektronischen vorrichtungen
DE102010009193B4 (de) Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend
KR20190077044A (ko) 유기 기능성 재료의 제형
KR20190022812A (ko) 유기 기능성 재료의 제형
JP6848033B2 (ja) 電気光学素子およびその使用
KR102515195B1 (ko) 전자 디바이스의 유기 소자를 형성하는 방법
EP3028320A1 (de) Elektrooptische vorrichtung und deren verwendung
KR20180066145A (ko) 적어도 2종의 유기 반도체 화합물 및 적어도 2종의 용매를 포함하는 제형
EP3241248A1 (de) Formulierungen und elektronische vorrichtungen
KR20240072268A (ko) 전자 디바이스의 유기 소자를 형성하는 방법

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20151211

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20200625

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

RAP3 Party data changed (applicant data changed or rights of an application transferred)

Owner name: MERCK PATENT GMBH

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230518

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20230407