EP2358841A1 - Organische elektrolumineszenzvorrichtung - Google Patents

Organische elektrolumineszenzvorrichtung

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Publication number
EP2358841A1
EP2358841A1 EP09756676A EP09756676A EP2358841A1 EP 2358841 A1 EP2358841 A1 EP 2358841A1 EP 09756676 A EP09756676 A EP 09756676A EP 09756676 A EP09756676 A EP 09756676A EP 2358841 A1 EP2358841 A1 EP 2358841A1
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EP
European Patent Office
Prior art keywords
formula
aromatic
compound
organic electroluminescent
atoms
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EP09756676A
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German (de)
English (en)
French (fr)
Inventor
Joachim Kaiser
Arne Buesing
Anja Gerhard
Philipp Stoessel
Susanne Heun
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of EP2358841A1 publication Critical patent/EP2358841A1/de
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    • 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
    • H—ELECTRICITY
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—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
    • 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
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum

Definitions

  • the present invention relates to phosphorescent organic electroluminescent devices which contain two phosphorescent dopants.
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • further improvements are needed.
  • the so-called roll-off behavior of the OLEDs ie the efficiency as a function of the brightness of the OLED, there is still room for improvement, since it is often observed that the efficiency drops sharply at high brightness. This applies in particular to electroluminescent devices which are doped with a phosphorescent emitter.
  • carbazole derivatives e.g. B. bis (carbazolyl) biphenyl
  • a matrix material for the phosphorescent emitter used as a matrix material for the phosphorescent emitter.
  • these matrix materials often lead to comparatively high operating voltages.
  • electron-conducting materials including ketones (for example according to WO 04/093207 or according to the unpublished application DE 102008033943.1), phosphine oxides and sulfones (WO 05/003253) are used as matrix materials for phosphorescent emitters.
  • ketones possibly due to the good electron transport properties, very low operating voltages and long lifetimes are achieved, which makes this class of compounds a very interesting matrix material.
  • these matrix materials often lead to a stronger roll-off behavior of the OLED, ie a greater decrease in efficiency at high brightness than with other matrix materials. There is therefore still room for improvement here.
  • these matrix materials sometimes show incompatibility with metal complexes containing ketoketonate ligands, for example, acetylacetonate. This is reflected in lower efficiency and lifetime.
  • metal complexes especially these metal complexes have proven to be emitters with very good emission properties, so that many of the currently used phosphorescent emitters are of this type of structure. There is therefore still room for improvement here.
  • the technical problem underlying this invention is therefore to provide an organic electroluminescent device which exhibits less high-brightness roll-off behavior.
  • the object is furthermore to provide an organic electroluminescent device which contains a metal complex with ketoketonate ligands and which leads to good emission properties with this dopant, in particular to good efficiency, a long service life and a low operating voltage.
  • an organic electroluminescent device which contains in the emitting layer an aromatic ketone or another of the matrix materials defined below which is substituted by two different phosphorescent emitters simultaneously has high efficiencies, long lifetimes and low Operating voltages, even with phosphorescent emitters containing Ketoketonatliganden show. Furthermore, these electroluminescent devices have a surprisingly low roll-off behavior, so that they can also be operated with good efficiency at high brightness.
  • organic electroluminescent devices which contain two phosphorescent emitters in a matrix.
  • organic electroluminescent devices which contain a host material and two phosphorescent dopants.
  • CBP bis (carbazolyl) biphenyl
  • these electroluminescent devices have very high operating voltages. The voltages are comparable or even higher than in
  • Electroluminescent devices containing only one phosphorescent dopant An influence on the roll-off behavior of the electroluminescent device is not disclosed.
  • organic electroluminescent devices which contain a host material, a phosphorescent dopant and a fluorescent or phosphorescent dopant, which emits longer wavelength.
  • Triarylamine derivatives and carbazole derivatives are disclosed in particular as the host material. This results in better efficiencies and a better lifetime especially for combination with a fluorescent dopant.
  • An influence on the lifetime is not disclosed for electroluminescent devices which contain two phosphorescent dopants.
  • an influence on the roll-off behavior of the electroluminescent device is not disclosed.
  • the invention thus relates to an organic electroluminescent devices comprising in at least one emitting layer
  • (C) a matrix material selected from the group consisting of aromatic ketones, aromatic phosphine oxides, aromatic sulfoxides and aromatic sulfones.
  • an aromatic ketone is understood to mean a carbonyl group to which two aromatic or heteroaryl aromatic groups or aromatic or heteroaromatic ring systems are directly bonded.
  • an aromatic sulfone is understood to mean a group S (OO) 2, to which two aromatic or heteroaromatic groups or aromatic or heteroaromatic ring systems are directly bonded.
  • X is C, P or S;
  • Ar is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which may be substituted in each case with one or more groups R 1 ;
  • R 1 is the same or different H, D, F, Cl, Br, I at each occurrence
  • Ar 1 is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
  • R 2 is identical or different at each occurrence H, D or an aliphatic, aromatic and / or heteroaromatic organic radical, in particular a hydrocarbon radical having 1 to 20 C atoms, in which also H atoms can be replaced by F; two or more adjacent substituents R 2 may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
  • neither Ar nor Ar 1 contains a triarylamine group or a carbazole group.
  • An organic electroluminescent device is understood to mean a device which contains the anode, cathode and at least one emitting layer, which is arranged between the anode and the cathode, wherein at least one layer between the anode and the cathode contains at least one organic or organometallic compound.
  • at least one emitting layer contains at least one phosphorescent emitter A, at least one phosphorescent emitter B and at least one compound of the above-mentioned formula (1).
  • An organic electroluminescent device need not necessarily contain only layers composed of organic or organometallic materials. So it is also possible that one or more layers contain inorganic materials or are constructed entirely of inorganic materials.
  • a phosphorescent compound in the context of this invention is a compound which exhibits luminescence at room temperature from an excited state with a higher spin multiplicity, ie a spin state> 1, in particular from an excited triplet state.
  • all luminescent transition metal complexes in particular all luminescent iridium and platinum compounds, are to be regarded as phosphorescent compounds.
  • An aryl group in the sense of this invention contains at least 6 C atoms;
  • a heteroaryl group contains at least 2 C atoms and at least 1 heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example naphthalene, anthracene, pyrene, quinoline, isoquinoline, etc., understood.
  • An aromatic ring system in the context of this invention contains at least 6 C atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains at least 2 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups a short, non-aromatic moiety (preferably less than 10% of the atoms other than H), e.g.
  • N or O atom may be connected.
  • systems such as 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are also to be understood as aromatic ring systems in the context of this invention.
  • aromatic or heteroaromatic ring system is understood as meaning systems in which a plurality of aryl or heteroaryl groups are linked together by single bonds, for example biphenyl, terphenyl or bipyridine.
  • a C 1 - to C 4 -alkyl group in which also individual H atoms or CH 2 groups can be substituted by the abovementioned groups particularly preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, tert-pentyl, 2-pentyl, cyclopentyl, n-hexyl, s -hexyl, tert -hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n- Octyl, 2-
  • An alkynyl group is particularly preferably understood to mean the radicals ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
  • a C 1 to C 40 -alkoxy group particular preference is given to methoxy, trifluoromethoxy, ethoxy, n-
  • an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms which may be substituted in each case with the abovementioned radicals R and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, Naphthalene, anthracene, phenanthrene, benzanthracene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, benzofluorene, dibenzofluorene, spirobifluorene, dihydrophenanthrene, dihydropyr
  • the compounds of the formula (1) preferably have a glass transition temperature TQ of greater than 70 ° C., more preferably greater than 90 ° C., very particularly preferably greater than 110 ° C.
  • the photoluminescence maximum of the phosphorescent compound A is at least 20 nm shorter wavelength than that of the phosphorescent compound B, particularly preferably at least 30 nm short-wave. This is especially true when compound A is a green phosphorescent compound and compound B is a red phosphorescent compound or when compound A is a blue phosphorescent compound and compound B is a green phosphorescent compound.
  • compound A is a deep blue phosphorescent compound and the compound B is a light blue phosphorescent compound, it is preferred that the compound A emit at least 10 nm short wavelength than the compound B.
  • the photoluminescence maximum is determined by measuring the photoluminescence spectrum of a 50 nm thick layer in which the compound A is doped in a proportion of 5% by volume or the compound B in a proportion of 5% by volume in the enrovende matrix material according to formula (1).
  • the emission spectrum of the electroluminescent device as a whole predominantly corresponds to the emission spectrum of the longer-wavelength emitting compound, that is, the compound B.
  • the phosphorescent compound A is a green-luminescent compound and the phosphorescent compound B is a red-luminescent compound.
  • the phosphorescent compound A is a blue-luminescent compound and the phosphorescent compound B is a green-luminescent compound or a red-luminescent compound.
  • the phosphorescent compound A is a deep blue luminescent or UV-emitting compound and the compound B is a light blue luminescent compound.
  • Green luminescence is understood as meaning a luminescence with a maximum of the photoluminescence spectrum in the range from 490 to 560 nm.
  • blue luminescence is meant a luminescence with a maximum of the photoluminescence spectrum in the range of 440 to 490 nm.
  • Deep blue luminescence is understood as meaning a luminescence with a maximum of the photoluminescence spectrum in the range from 350 to 460 nm.
  • light blue luminescence is meant a luminescence with a maximum of the photoluminescence spectrum in the range of 460 to 490 nm.
  • the photoluminescence spectrum is measured as described above.
  • the proportion of the phosphorescent compound A in the layer is preferably 5 to 50% by volume, particularly preferably 10 to 25% by volume, very particularly preferably 12 to 20% by volume.
  • the proportion of phosphorescent compound B in the layer is preferably 1 to 20% by volume, more preferably 3 to 10% by volume, most preferably 4 to 7% by volume.
  • the phosphorescent compound A is preferably a material capable of transporting holes. Since the location of the HOMO (highest occupied molecular orbital) is responsible for the hole transport properties of the material, compound A preferably has a HOMO of> -5.9 eV, more preferably> -5.7 eV and most preferably of> -5.5 eV.
  • the HOMO can be determined by photoelectron spectroscopy using Model AC-2 photon electron spectrometer from Riken Keiki Co. Ltd. (Http://www.rikenkeiki.com/pages/AC2.htm).
  • Particularly suitable phosphorescent compounds A and B are compounds which, when suitably excited, emit light, preferably in the visible range, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80.
  • Preferred phosphorescence emitters A and B are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
  • Particularly preferred organic electroluminescent devices contain as phosphorescent compound A and / or as phosphorescent compound B at least one compound of the formulas (2) to (5),
  • DCy is, identically or differently on each occurrence, a cyclic group which contains at least one donor atom, preferably nitrogen, carbon in the form of a carbene or phosphorus, via which the cyclic group is bonded to the metal, and which in turn has one or more substituents R 1 can carry; the groups DCy and CCy are linked by a covalent bond;
  • CCy is the same or different at each occurrence a cyclic
  • A is the same or different at each occurrence as a mononionic, bidentate chelating ligand, preferably a diketonate ligand or a picolinate ligand.
  • ring systems between a plurality of radicals R 1 there may also be a bridge between the groups DCy and CCy. Furthermore, by forming ring systems between a plurality of radicals R 1, there may also be a bridge between two or three ligands CCy-DCy or between one or two ligands CCy-DCy and the ligand A, so that it is a polydentate or polypodal ligand system ,
  • the compound A is preferably a compound of the abovementioned formula (3), in particular tris (phenylpyridyl) iridium, which may be substituted by one or more radicals R 1 .
  • the compound A is tris (phenylpyridyl) iridium.
  • the compound B is preferably a compound of the above-mentioned formulas (2), (3) or (5), particularly preferably of the formulas (2) or (5), very particularly preferably of the formula (2).
  • a in formula (2) is preferably acetylacetonate or an acetylacetonate derivative.
  • Examples of preferred phosphorescent compounds A and B are listed in the following table.
  • Suitable compounds according to formula (1) are the ketones disclosed in WO 04/093207 and the unpublished DE 102008033943.1 and the phosphine oxides, sulfoxides and sulfones disclosed in WO 05/003253. These are via quote part of the present invention.
  • the symbol X is C or P, particularly preferably C. They are therefore preferably ketones or phosphine oxides, more preferably ketones.
  • the definition of the compound according to formula (1) shows that it not only has to contain a carbonyl or phosphine oxide group, but can also contain several of these groups.
  • the group Ar in compounds according to formula (1) is preferably an aromatic ring system having 6 to 40 aromatic ring atoms.
  • the aromatic ring system need not necessarily have only aromatic groups, but also two aryl groups may be interrupted by a non-aromatic group, for example by another carbonyl group.
  • the group Ar has no more than two condensed rings. It is therefore preferably composed only of phenyl and / or naphthyl groups, particularly preferably only of phenyl groups, but does not contain any larger condensed aromatics, such as, for example, anthracene.
  • Preferred groups Ar which are bonded to the carbonyl group are phenyl, 2-, 3- or 4-tolyl, 3- or 4-o-xylyl, 2- or 4-m-xylyl, 2-p-xylyl, , m- or p-tert-butylphenyl, o-, m- or p-fluorophenyl, benzophenone, 1-, 2- or 3-phenylmethanone, 2-, 3- or 4-biphenyl, 2-, 3- or 4- o-terphenyl, 2-, 3- or 4-m-terphenyl, 2-, 3- or 4-p-terphenyl, 2 '-p-terphenyl, 2', 4 'or 5' - m-terphenyl, 3 '- or 4' -o-terphenyl, p, m, o, p, m, m, o, m- or o, o-quaterphenyl, quinquephenyl, sexiphen
  • the groups Ar may be substituted by one or more radicals R 1 .
  • the group Ar 1, identical or different at each occurrence is an aromatic ring system having 6 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 .
  • Ar 1 is more preferably identical or different at each occurrence, an aromatic ring system having 6 to 12 aromatic ring atoms.
  • Preferred aromatic ketones, phosphine oxides, sulfoxides and sulfones are therefore the compounds of the following formulas (6) to (30),
  • Z is the same or different every occurrence CR 1 or N, with a maximum of 3 symbols Z per ring for N; preferably Z is CR 1 ;
  • n 1, 2, 3, 4 or 5;
  • n is the same or different at each occurrence 0, 1, 2, 3 or 4;
  • p is the same or different 0 or 1 at each occurrence.
  • Ar in the abovementioned formulas (6) to (30) is preferably an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R 1 .
  • Particularly preferred are the abovementioned groups Ar.
  • aromatic ketones are benzophenone derivatives which are each substituted at the 3,3 ', 5,5'-positions by an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in turn is replaced by one or more radicals R 1 according to the above definition can be substituted.
  • suitable compounds according to formula (1) are the compounds (1) to (72) depicted below.
  • the organic electroluminescent device may contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, charge generation layers (Charge Generation Layers, IDMC 2003, Taiwan, Session 21 OLED (5), T. Matsumoto, T. Nakada). J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or Organic or Inorganic P / N Transitions.
  • interlayers may be present, which control, for example, the charge balance in the device.
  • the layers, in particular the charge transport layers may also be doped. The doping of the layers may be advantageous for improved charge transport. It should be noted, however, that not necessarily each of these layers must be present and the choice of layers always depends on the compounds used.
  • the organic electroluminescent device contains a plurality of emitting layers, wherein at least one emitting layer contains at least one phosphorescent compound A, one phosphorescent compound B and one compound according to formula (1). Particularly preferably, these emission layers have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce and emit the blue and yellow, orange or red light.
  • three-layer systems ie systems with three emitting layers, wherein at least one of these layers contains at least one phosphorescent compound A, a phosphorescent compound B and a compound according to formula (1) and wherein the three layers show blue, green and orange or red emission (For the basic structure see eg WO 05/011013).
  • the use of more than three emitting layers may also be preferred.
  • a matrix material is selected from compounds of the formula (1).
  • Preferred hole-conducting matrix materials are triarylamines, carbazole derivatives, e.g. B. CBP (N, N-bis-carbazolylbiphenyl) or in WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 08/086851 disclosed carbazole derivatives, Azacarbazole, z. B. according to EP 1617710, EP 1617711,
  • bipolar matrix materials e.g. B. according to WO 07/137725, and benzothiophene or Dibenzothiophenderivate, z. B. according to WO 09/021126.
  • the mixture of matrix materials may also contain more than two matrix materials.
  • two or more materials according to formula (1) can be used.
  • an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
  • the materials become in vacuum sublimation at a pressure less than 10 "5 mbar, preferably less than 10 " 6 mbar evaporated. It should be noted, however, that the pressure can be even lower, for example less than 10 "7 mbar.
  • organic electroluminescent device characterized in that one or more layers with the
  • OVPD Organic Vapor Phase Deposition
  • carrier gas sublimation a carrier gas sublimation
  • the materials are applied at a pressure between 10 "applied 5 mbar and 1 bar.
  • OVJP organic vapor jet printing
  • the materials are applied directly through a nozzle and patterned (eg. BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
  • an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
  • any printing process such as screen printing, flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • inkjet printing ink jet printing
  • soluble compounds are needed. High solubility can be achieved by suitable substitution of the compounds.
  • solutions of individual materials can be applied, but also solutions containing several compounds, for example matrix materials and dopants.
  • the organic electroluminescent device may also be fabricated as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
  • a hybrid system by applying one or more layers of solution and depositing one or more other layers.
  • the emitting layer comprising a compound of the formula (1) and the phosphorescent compounds A and B are evaporated in vacuo and one or more other layers can be applied from solution.
  • Another object of the present invention are mixtures comprising at least one phosphorescent compound A, at least one phosphorescent compound B and at least one aromatic ketone, aromatic phosphine oxide, aromatic sulfoxide or aromatic sulfone, preferably a compound according to formula (1).
  • Yet another object of the present invention are solutions or formulations containing at least one mixture according to the invention and at least one solvent.
  • the organic electroluminescent devices according to the invention have a very high efficiency. This is especially true when phosphorescent metal complexes with Ketoketonatliganden, z. Acetylacetonate ligands.
  • the organic electroluminescent devices according to the invention simultaneously have a very good service life. This is especially true when phosphorescent metal complexes are used with Ketoketonatliganden.
  • the organic electroluminescent devices according to the invention simultaneously have a very low operating voltage. In particular, the operating voltage is significantly lower than with matrix materials based on carbazole derivatives. 4.
  • the organic electroluminescent devices according to the invention have a very low roll-off behavior. Thus, the roll-off is significantly lower than with electroluminescent devices, which also contain a compound according to formula (1), but only a phosphorescent compound.
  • Example 1-13 Preparation and characterization of organic electroluminescent devices according to the invention
  • Electroluminescent devices according to the invention can be prepared as described, for example, in WO 05/003253. In the following, the results of different OLEDs are compared.
  • Q Examples 1-13 describe red-emitting OLEDs that are realized by the following layer structure:
  • HIL Hole Injection Layer 20 nm 2,2 ', 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
  • HTL Hole transporting layer 20 nm NPB (N-naphthyl-N-phenyl-4,4 1 - diaminobiphenyl).
  • Emission Layer 30 nm Matrix Material: Spiro-Ketone (SK)
  • HBL Hole blocking layer
  • ETL Electron conductor
  • OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) as a function of the brightness, the operating voltage, calculated from current-voltage-luminance characteristic curves (LUL characteristic curves), and the service life are determined.
  • Example 1 serves as a comparative example and contains TER-1 as dopant.
  • Example 2 describes an inventive OLED, in addition to TER-1 lr (ppy) 3 as further dopant. From Table 1 it can be seen that the OLED of the invention compared to the comparative example has a significantly improved efficiency and life, without affecting the color or the operating voltage.
  • Comparative Examples 12 and 13 show the effect of a second dopant using the prior art host material CBP.
  • CBP prior art host material
  • Example 14-16 Preparation and characterization of organic electroluminescent devices according to the invention
  • Examples 14-16 describe blue and green emitting OLEDs that are realized by the following layer construction and can be generated by the general method mentioned above:
  • HIL Hole Injection Layer 20 nm 2,2 ' ) 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
  • HTL Hole transport layer 5 nm NPB (N-naphthyl-N-phenyl-4,4'-diaminobiphenyl).
  • Emission layer 40 nm ketone (K)
  • Dotand lr (ppy) 3 (fac-tris [2-phenylpyridyl] iridium) as a comparative example; in examples according to the invention dopant 1 doped with dopant 2 (degree of doping see table 2).
  • Dotand 1 and Dotand 2 are TEB 1 Flrpic or Ir (ppy) 3 ;
  • HBL Hole Blocking Layer
  • K Ketone
  • ETL Electron Conductor
  • EBM, TEB, Flrpic, and K are shown below for the sake of clarity.
  • the efficiency is increased by the introduction of the dopant Flrpic in a green Ir (ppy) 3 device. At the same time the color improves.
  • This concept can also be implemented in a blue-green emitting device with high efficiency, as the example 16 shows.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
EP09756676A 2008-12-17 2009-11-18 Organische elektrolumineszenzvorrichtung Withdrawn EP2358841A1 (de)

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Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008033563A1 (de) 2008-07-17 2010-01-21 Merck Patent Gmbh Komplexe mit kleinen Singulett-Triplett-Energie-Abständen zur Verwendung in opto-elektronischen Bauteilen (Singulett-Harvesting-Effekt)
DE102010010481A1 (de) 2010-03-06 2011-09-08 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010027319A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
JP5968885B2 (ja) * 2010-07-30 2016-08-10 メルク パテント ゲーエムベーハー 有機エレクトロルミネセンスデバイス
WO2012027427A1 (en) * 2010-08-24 2012-03-01 E. I. Du Pont De Nemours And Company Photoactive composition and electronic device made with the composition
DE102010048498A1 (de) * 2010-10-14 2012-04-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
KR101920513B1 (ko) * 2011-04-05 2018-11-20 메르크 파텐트 게엠베하 유기 전계발광 디바이스
EP2742054B1 (de) 2011-08-10 2016-10-12 Merck Patent GmbH Metallkomplexe
KR101897045B1 (ko) * 2011-10-20 2018-09-10 에스에프씨 주식회사 유기금속 화합물 및 이를 포함하는 유기전계발광소자
CA2879094C (en) * 2012-08-02 2020-07-28 F. Hoffmann-La Roche Ag Iridium-based complexes for ecl
CN104718218B (zh) 2012-08-02 2017-10-24 霍夫曼-拉罗奇有限公司 用于ecl的新型铱基配合物
EP2880043B1 (en) 2012-08-02 2016-09-21 Roche Diagnostics GmbH New bis-iridium-complexes for manufacturing of ecl-labels
CN107602620B (zh) 2012-08-02 2020-08-28 霍夫曼-拉罗奇有限公司 用于ecl的新型铱基络合物
JP2015530979A (ja) 2012-08-02 2015-10-29 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｅｃｌ用の新規イリジウムベース錯体
WO2014056565A1 (de) 2012-10-09 2014-04-17 Merck Patent Gmbh Elektronische vorrichtung
EP2960315A1 (de) 2014-06-27 2015-12-30 cynora GmbH Organische Elektrolumineszenzvorrichtung
EP2963044A1 (de) 2014-06-30 2016-01-06 cynora GmbH Zweikernige Metall(I)-Komplexe mit tetradentaten Liganden für optoelektronische Anwendungen
EP3221422B1 (de) 2014-11-18 2018-06-13 cynora GmbH Kupfer(i)komplexe für optoelektronische anwendungen
EP3539972B1 (en) * 2018-03-13 2021-07-28 Samsung Display Co., Ltd Organometallic compound and organic light-emitting device including the same
TW202030902A (zh) 2018-09-12 2020-08-16 德商麥克專利有限公司 電致發光裝置
CN112639052A (zh) 2018-09-12 2021-04-09 默克专利有限公司 用于有机电致发光器件的材料
TWI826522B (zh) 2018-09-12 2023-12-21 德商麥克專利有限公司 電致發光裝置
US20220127286A1 (en) 2019-03-04 2022-04-28 Merck Patent Gmbh Ligands for nano-sized materials
JP2022527591A (ja) 2019-04-11 2022-06-02 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のための材料
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
WO2021151922A1 (de) 2020-01-29 2021-08-05 Merck Patent Gmbh Benzimidazol-derivate
US20230337537A1 (en) 2020-03-23 2023-10-19 Merck Patent Gmbh Materials for organic electroluminescent devices
EP4099420A1 (en) * 2021-06-03 2022-12-07 Samsung Electronics Co., Ltd. Composition, layer including the composition, light-emitting device including the composition, and electronic apparatus including the light-emitting device
WO2024105066A1 (en) 2022-11-17 2024-05-23 Merck Patent Gmbh Materials for organic electroluminescent devices

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0676461B1 (de) 1994-04-07 2002-08-14 Covion Organic Semiconductors GmbH Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien
DE19652261A1 (de) 1996-12-16 1998-06-18 Hoechst Ag Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen
DE60031729T2 (de) 1999-05-13 2007-09-06 The Trustees Of Princeton University Lichtemittierende, organische, auf elektrophosphoreszenz basierende anordnung mit sehr hoher quantenausbeute
CN1840607B (zh) 1999-12-01 2010-06-09 普林斯顿大学理事会 作为有机发光器件的磷光掺杂剂的l2mx形式的络合物
US6660410B2 (en) 2000-03-27 2003-12-09 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
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
CN101924190B (zh) 2000-08-11 2012-07-04 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
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 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
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
US6893743B2 (en) 2000-10-04 2005-05-17 Mitsubishi Chemical Corporation Organic electroluminescent device
JP4039023B2 (ja) * 2000-10-04 2008-01-30 三菱化学株式会社 有機電界発光素子
JP4493915B2 (ja) * 2001-05-16 2010-06-30 ザ、トラスティーズ オブ プリンストン ユニバーシティ 高効率多色電界リン光ｏｌｅｄ
DE10310887A1 (de) 2003-03-11 2004-09-30 Covion Organic Semiconductors Gmbh Matallkomplexe
KR100501702B1 (ko) * 2003-03-13 2005-07-18 삼성에스디아이 주식회사 유기 전계 발광 디스플레이 장치
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
JP5318347B2 (ja) * 2003-04-15 2013-10-16 メルク パテント ゲーエムベーハー 発光可能な、マトリックス材料と有機半導体との混合物、その使用、ならびに前記混合物を含む電子部品
DE10317556B4 (de) * 2003-04-15 2021-05-12 Merck Patent Gmbh Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese
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
EP2251396B1 (de) * 2003-07-07 2014-11-19 Merck Patent GmbH Zur Emission befähigte organische Verbindungen und Elektronikbauteile diese enthaltend
DE10330761A1 (de) * 2003-07-07 2005-02-03 Covion Organic Semiconductors Gmbh Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend dieses
DE10333232A1 (de) * 2003-07-21 2007-10-11 Merck Patent Gmbh Organisches Elektrolumineszenzelement
JP4455211B2 (ja) * 2003-08-29 2010-04-21 キヤノン株式会社 発光素子及び表示装置
JP4625005B2 (ja) * 2003-09-19 2011-02-02 メルク パテント ゲーエムベーハー 有機エレクトロルミネセンス素子
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
DE10350722A1 (de) 2003-10-30 2005-05-25 Covion Organic Semiconductors Gmbh Metallkomplexe
US7790890B2 (en) 2004-03-31 2010-09-07 Konica Minolta Holdings, Inc. Organic electroluminescence element material, organic electroluminescence element, display device and illumination device
DE102004023277A1 (de) 2004-05-11 2005-12-01 Covion Organic Semiconductors Gmbh Neue Materialmischungen für die Elektrolumineszenz
WO2005112520A1 (ja) * 2004-05-18 2005-11-24 Nippon Hoso Kyokai 発光素子
US7825249B2 (en) 2004-05-19 2010-11-02 Merck Patent Gmbh Metal complexes
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
JP2006054422A (ja) * 2004-07-15 2006-02-23 Fuji Photo Film Co Ltd 有機電界発光素子及び表示素子
DE102004034517A1 (de) 2004-07-16 2006-02-16 Covion Organic Semiconductors Gmbh Metallkomplexe
TW200634020A (en) 2004-12-09 2006-10-01 Merck Patent Gmbh Metal complexes
JP2008528646A (ja) 2005-02-03 2008-07-31 メルク パテント ゲーエムベーハー 金属錯体
JP5242380B2 (ja) 2005-05-03 2013-07-24 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子
JP5080774B2 (ja) * 2005-10-04 2012-11-21 富士フイルム株式会社 有機電界発光素子
US20070247061A1 (en) 2006-04-20 2007-10-25 Vadim Adamovich Multiple dopant emissive layer OLEDs
DE102006025777A1 (de) 2006-05-31 2007-12-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
JP5205584B2 (ja) * 2006-09-06 2013-06-05 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子および表示装置
DE102007002714A1 (de) 2007-01-18 2008-07-31 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
JP5081010B2 (ja) * 2007-03-26 2012-11-21 富士フイルム株式会社 有機電界発光素子
WO2008140115A1 (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
DE102008027005A1 (de) 2008-06-05 2009-12-10 Merck Patent Gmbh Organische elektronische Vorrichtung enthaltend Metallkomplexe
DE102008033943A1 (de) 2008-07-18 2010-01-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010069442A1 *

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