WO2011070991A1 - Nouveau complexe de l'iridium, dispositif électroluminescent organique et appareil d'affichage d'images - Google Patents

Nouveau complexe de l'iridium, dispositif électroluminescent organique et appareil d'affichage d'images Download PDF

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WO2011070991A1
WO2011070991A1 PCT/JP2010/071754 JP2010071754W WO2011070991A1 WO 2011070991 A1 WO2011070991 A1 WO 2011070991A1 JP 2010071754 W JP2010071754 W JP 2010071754W WO 2011070991 A1 WO2011070991 A1 WO 2011070991A1
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compound
iridium complex
emitting device
organic light
light
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PCT/JP2010/071754
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Shigemoto Abe
Masashi Hashimoto
Chiaki Nishiura
Hiroya Nitta
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Canon Kabushiki Kaisha
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Priority to US13/514,030 priority Critical patent/US9045510B2/en
Publication of WO2011070991A1 publication Critical patent/WO2011070991A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/02—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor bodies
    • H01L33/14—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor bodies with a carrier transport control structure, e.g. highly-doped semiconductor layer or current-blocking structure
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • 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
    • C09K2211/10—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
    • 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
    • C09K2211/10—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
    • 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
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition

Definitions

  • the present invention relates to an iridium complex, an organic light-emitting device containing the iridium complex, and an image display apparatus containing the iridium complex.
  • Patent Literature 1 describes an iridium complex having the following structural formula.
  • Patent Literature 2 describes derivatives of this compound into which various substituents are introduced.
  • Patent Literature 1 Ir(Pim) 3 , emits blue light (Patent Literature 1). Although derivatives of this compound into which various substituents are introduced are being studied, none of the derivatives have had desirable characteristics (Patent Literature 2).
  • the present invention provides a novel iridium complex that has excellent light-emitting properties in a blue to green emission region.
  • the present invention also provides an organic light-emitting device that contains the iridium complex and has excellent light-emitting properties.
  • the present invention provides an iridium complex having the following general formula (1):
  • H denotes a hydrogen atom
  • N denotes a nitrogen atom
  • Ir denotes an iridium atom
  • Ri and R 2 denote an alkyl group
  • R 3 denotes an alkyl group or a substituted
  • R 4 and R 5 are independently selected from a hydrogen atom and alkyl groups
  • R6 denotes a hydrogen atom or a cyano group.
  • Fig. 1 is a schematic cross-sectional view of an organic light-emitting device and a switching device disposed under the organic light-emitting device.
  • the switching device is connected to the organic light-emitting device.
  • Fig. 2 shows the PL spectra of a compound pil-1 according to one embodiment of the present invention and a reference example Ir(Pim) 3 in toluene at room temperature.
  • Fig. 3 shows the PL spectra of the compound pil-1 according to one embodiment of the present invention and the reference example Ir(Pim) 3 in toluene at a temperature of 77 K.
  • Fig. 4 shows the PL spectra of the compound pil-1 according to one embodiment of the present invention and reference examples bIr-01 and gIr-01 in toluene at room temperature .
  • FIG. 5 shows the PL spectra of the compound pil-1 according to one embodiment of the present invention and the reference examples blr-Ol and gIr-01 in toluene at a
  • An iridium complex according to one embodiment of the present invention has the following general formula (1):
  • H denotes a hydrogen atom
  • N denotes a nitrogen atom
  • Ir denotes an iridium atom
  • Ri and R2 denote an alkyl group
  • R3 denotes an alkyl group or a substituted
  • R 4 and R 5 are independently selected from a hydrogen atom and alkyl groups
  • R 6 denotes a hydrogen atom or a cyano group.
  • the iridium complex having the general formula (1) according to one embodiment of the present invention has a skeleton in which a triazine ring, a phenyl ring, and an imidazole ring are bonded at particular positions.
  • This skeleton is
  • the iridium complex according to one embodiment of the present invention is an excellent blue- or green-light- emitting complex because of a strong ligand field resulting from the main skeleton of a ligand having the general formula ( 1 ) .
  • the ligand structure composed of the triazine ring, the phenyl ring, and the imidazole ring may be one of the following four structures A to D.
  • the structure C that is, the main skeleton of a ligand having the general formula (1) is excellent as a basic skeleton of a light- emitting material particularly in a blue emission region.
  • the position of the triazine ring on the phenyl ring is ortho or para to iridium bonded to the phenyl ring.
  • the triazine ring and the phenyl ring can lie in the same plane.
  • the structure B does not meet the first requirement because the triazine ring on the phenyl ring is meta to iridium.
  • the triazine ring and the phenyl ring cannot lie in the same plane because of the steric repulsion between the triazine ring and a substituent on the phenyl ring disposed adjacent to the triazine ring, that is, the iridium atom in the structure A and the
  • the main skeleton of a ligand having the general formula (1) provides excellent light-emitting properties in a blue to green emission region, particularly in a blue emission region.
  • the dihedral angle was calculated by structural optimization calculation in the ground state using a
  • Gaussian 03* Revision D.01. The density functional theory was employed as quantum chemical calculation. B3LYP was used as a functional.
  • the basis function was 6-31G*.
  • Examples of the alkyl groups of Ri and R 2 include, but are not limited to, a methyl group, an ethyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a neopentyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a bicyclo [2.2.2 ] octan-l-yl group, and a 1-adamantyl group.
  • Ri and R 2 may be the same or different.
  • Ri and R 2 be an alkyl group having a large excluded volume.
  • An alkyl group having a large excluded volume can surround lone-pair electrons of the triazine ring to reduce the coordinating ability of the nitrogen atoms of the triazine ring.
  • a specific substituent having a large excluded volume can effectively be a
  • substituent containing a tertiary carbon having an SP 3 hybrid orbital for example, a tert-butyl group, a
  • Effect 1 A high-purity iridium complex can be produced in high yield.
  • Effect 3 An alkyl group having a large excluded volume can reduce intermolecular interaction and the concentration quenching of a light-emitting material.
  • the concentration quenching is a phenomenon in which the emission intensity decreases at high concentrations.
  • Examples of the alkyl groups of R 3 , R 4 , and R5 include, but are not limited to, a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, and a neopentyl group.
  • the alkyl groups of R 3 , R 4 , and R5 may be the same or different.
  • R 3 be a low-molecular-weight alkyl group or a substituted or unsubstituted phenyl group in view of the purification of the complex. Since the life of the device increases with decreasing liberation of a substituent from an excited complex in the charge-transfer transition from the central metal to the ligand, it is desirable that R 3 be an alkyl group or a substituted or unsubstituted phenyl group. Examples of the substituent of the phenyl group of R 3 include, but are not limited to, a methyl group and an ethyl group. It is desirable that the substituent of the phenyl group of R 3 be a methyl group or an ethyl group because of the low molecular weight.
  • R 5 be a hydrogen atom or a low-molecular-weight alkyl group in view of the purification of the complex.
  • R 5 can effectively be an alkyl group, such as a methyl group or an ethyl group.
  • R 6 is close to the adjacent ligand, it is desirable that R 6 be a substituent having a small excluded volume, such as a hydrogen atom or a cyano group, to achieve a high synthesis yield of the complex.
  • a cyano group is effective in increasing back donation from the metal to increase ligand field splitting.
  • An iridium complex according to one embodiment of the present invention can be used as a guest material or a host material for a light-emitting layer of an organic light-emitting device according to one embodiment of the present invention.
  • An organic light-emitting device can be used as a guest material or a host material for a light-emitting layer of an organic light-emitting device according to one embodiment of the present invention.
  • An organic light-emitting device includes a pair of electrodes and a light-emitting layer between the electrodes.
  • An organic light-emitting device may further include another layer.
  • An iridium complex according to one embodiment of the present invention can be appropriately used in layers other than the light-emitting layer, for example, a hole- injection layer, a hole-transport layer, a hole/exciton blocking layer, an electron-transport layer, and an
  • the host material is a compound having the highest weight ratio
  • the guest material is a compound having a lower weight ratio than the host material.
  • An iridium complex according to one embodiment of the present invention can be used as a guest material for a light-emitting layer of an organic light-emitting device according to one embodiment of the present invention.
  • it is desirable that an iridium complex can be used as a guest material for a light-emitting layer of an organic light-emitting device according to one embodiment of the present invention.
  • the present invention be used as a guest material for a blue- or green-light-emitting device .
  • the introduction of a substituent into the basic skeleton of an iridium complex according to one embodiment of the present invention can alter the emission wavelength.
  • substituents that can alter the emission wavelength include, but are not limited to, alkyl groups and a cyano group.
  • the host material be a material having a higher LUMO level than the iridium complex, that is, a material having an energy level closer to the vacuum level.
  • an iridium complex according to one embodiment of the present invention has a low LUMO level and can accept electrons smoothly from the host material in the light-emitting layer.
  • the LUMO level stands for the lowest unoccupied molecular orbital level.
  • the HOMO level stands for the highest occupied molecular orbital level.
  • Iridium complexes according to embodiments of the present invention can be divided into the following four groups .
  • substituent on the basic skeleton of an iridium complex allows light emission in the blue to green region.
  • a ligand of an organic compound having the general formula (1) can be synthesized through the synthetic routes 1, 2, 3, and 4 described below with reference to Angew. Chem. Int. Ed., (2008), Vol. 47, 8246-8250, Org. Lett., (2007), Vol. 9, 4195-4198, Organic Syntheses, (2005), Vol. 81, 105- 111, WO 2008/124850, and J. Med. Chem. , (2007), Vol. 50, 528-542.
  • the ligand can be any organic compound described above.
  • the ligand can be any organic compound described above.
  • a hydrogen atom can be substituted with another substituent, such as an alkyl group or a cyano group.
  • An organic light-emitting device includes a pair of electrodes, an anode and a cathode, and an organic compound layer between the electrodes.
  • the organic compound layer contains an iridium complex having the general formula (1).
  • carriers of the anode and the cathode are injected into the organic compound layer to produce an exciton of the light-emitting iridium complex.
  • the organic light-emitting device emits light while the exciton returns to the ground state.
  • the light-emitting layer may be formed only of an iridium complex according to one embodiment of the present invention or may contain another component.
  • the iridium complex may be the main component or an
  • the main component is a component having the
  • An accessory component is a component having a lower weight ratio than the main component.
  • a material of the main component can also be any material of the main component.
  • a host material referred to as a host material.
  • a material of an accessory component is a dopant (guest) material.
  • Other accessory components include an emitting-assist material and a charge-injection material.
  • a device that includes an iridium complex having the general formula (1) according to one embodiment of the present invention as a host material or a guest material, particularly a guest material, of a light- emitting layer can efficiently output high-intensity light and have high durability.
  • An organic light-emitting device that includes an iridium complex according to one embodiment of the present invention may include an anode, a light-emitting layer, and a cathode in this order on a substrate.
  • Another organic light-emitting device that includes an iridium complex according to one embodiment of the present invention may include an anode, a hole-transport layer, an electron- transport layer, and a cathode in this order.
  • Still another organic light-emitting device that includes an iridium complex according to one embodiment of the present invention may include an anode, a hole-transport layer, a light- emitting layer, an electron-transport layer, and a cathode in this order.
  • Still another organic light-emitting device that includes an iridium complex according to one embodiment of the present invention may include an anode, a hole- injection layer, a hole-transport layer, a light-emitting layer, an electron-transport layer, and a cathode in this order, or an anode, a hole-transport layer, a light-emitting layer, a hole/exciton blocking layer, an electron-transport layer, and a cathode in this order.
  • These five multilayer organic light-emitting devices only have a basic structure.
  • An organic light-emitting device that includes an iridium complex according to one embodiment of the present invention is not limited to these devices.
  • an insulating layer, an adhesive layer, or an interference layer may be disposed at an interface between an electrode and an organic compound layer.
  • An electron-transport layer or a hole- transport layer may be formed of two sublayers having
  • An iridium complex having the general formula (1) according to one embodiment of the present invention may be used in an organic compound layer of a light-emitting device having any layer structure.
  • an iridium complex having the general formula (1) may be used in an organic compound layer of a light-emitting device having any layer structure.
  • another compound may be used if necessary.
  • the other compound include, but are not limited to, a hole- injecting compound, a hole-transporting compound, a host compound, which is a host material, a light-emitting
  • the hole-injecting compound and hole-transporting compound be materials having high hole mobility.
  • the low- or high-molecular-weight material having hole-injection ability or hole-transport ability include triarylamine derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine
  • porphyrin derivatives porphyrin derivatives, polyvinylcarbazole, polythiophene, and other electroconductive polymers.
  • the following table shows specific structural formulae of the host compounds.
  • the host compounds may be derivatives of the compounds having structural formulae shown in the table.
  • Other examples of the host compounds include, but are not limited to, fused-ring compounds (for example, fluorene derivatives, naphthalene derivatives, carbazole derivatives, quinoxaline derivatives, and
  • quinoline derivatives include organic aluminum complexes, such as tris ( 8-quinolinolate) aluminum, organozinc complexes, triphenylamine derivatives, and polymer derivatives, such as polyfluorene derivatives and polyphenylene derivatives.
  • organic aluminum complexes such as tris ( 8-quinolinolate) aluminum
  • organozinc complexes such as tris ( 8-quinolinolate) aluminum
  • triphenylamine derivatives such as triphenylamine derivatives
  • polymer derivatives such as polyfluorene derivatives and polyphenylene derivatives.
  • the electron-injecting compound or the electron- transporting compound is selected in consideration of balance with hole mobility of the hole-injecting compound or the hole-transporting compound.
  • Examples of the compound having electron-injection ability or electron-transport ability include, but are not limited to, oxadiazole
  • the material for the anode have a work function as large as possible.
  • the anode material include, but are not limited to, metallic elements, such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, alloys of these metallic elements, and metal oxides, such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide.
  • metallic elements such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten
  • metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide.
  • the anode material also include, but are not limited to, electroconductive polymers, such as polyaniline, polypyrrole, and polythiophene . These electrode substances may be used alone or in combination.
  • the anode may have a monolayer or multilayer structure.
  • the material for the cathode have a work function as small as possible.
  • the cathode material include, but are not limited to, alkali metals, such as lithium, alkaline-earth metals, such as calcium, and metallic elements, such as aluminum, titanium, manganese, silver, lead, and chromium.
  • the cathode material also include, but are not limited to, alloys of these metallic elements, such as magnesium-silver, aluminum-lithium, and aluminum-magnesium.
  • Metal oxides, such as indium tin oxide (ITO) may also be used. These electrode substances may be used alone or in combination.
  • the cathode may have a monolayer or multilayer structure.
  • a layer containing an iridium complex according to one embodiment of the present invention and a layer composed of another organic compound can be formed in the following manner.
  • a thin film is generally formed by a vacuum evaporation method, an ionized deposition method, sputtering, plasma CVD, or a known coating method (for example, spin coating, dipping, casting, an LB method, or an ink jet method) using a
  • a layer formed by a vacuum evaporation method or a solution coating method experiences little crystallization and has excellent
  • an iridium complex according to one embodiment of the present invention can be used in combination with an appropriate binder resin.
  • binder resin examples include, but are not limited to, a polyvinylcarbazole resin, a polycarbonate resin, a polyester resin, an ABS resin, an acrylic resin, a polyimide resin, a phenolic resin, an epoxy resin, a
  • silicone resin and a urea resin.
  • binder resins may be used alone as a homopolymer or copolymer or in
  • an additive agent such as a known plasticizer, antioxidant, and/or ultraviolet absorber, may be used.
  • An organic light-emitting device can be used in display apparatuses and lighting apparatuses.
  • An organic light- emitting device can also be used in exposure light sources of electrophotographic image-forming apparatuses and backlights of liquid crystal displays.
  • a display apparatus includes an organic light- emitting device according to one embodiment of the present invention in the display.
  • the display includes pixels, which include an organic light-emitting device according to one embodiment of the present invention.
  • the display apparatus can be used as an image display apparatus of PCs.
  • the display apparatus may be used in displays of image pickup devices, such as digital cameras and digital video cameras.
  • Image pickup devices include the display and an image-capturing unit including an imaging optical system.
  • a display apparatus that includes an organic light- emitting device according to one embodiment of the present invention will be described below.
  • Fig. 1 is a schematic cross-sectional view of an organic light-emitting device according to one embodiment of the present invention and a switching device TFT disposed on a substrate.
  • the switching device TFT is connected to the organic light-emitting device and drives the organic light- emitting device. This structure will be described in detail below .
  • a display apparatus 3 illustrated in Fig. 1 includes a substrate 31, for example, formed of glass, a moisture-proof film 32 for protecting a TFT or an organic compound layer, a gate electrode 33, for example, formed of a metal, such as Cr, a gate-insulating film 34, and a semiconductor layer 35.
  • a TFT device 38 includes the semiconductor film 35, a drain electrode 36, and a source electrode 37.
  • insulating film 39 is disposed on the TFT device 38.
  • An anode 311 of the organic light-emitting device is connected to the source electrode 37 through a contact hole (through hole) 310.
  • a multilayer organic compound layer 312 is
  • a first protective layer 314 and a second protective layer 315 for preventing degradation of the organic light-emitting device are illustrated as a single layer in Fig. 1.
  • the TFT device controls the luminance of the organic light-emitting device.
  • a plurality of organic light-emitting devices on the substrate can emit light having their respective luminance to display images.
  • a MIM device may also be used as the switching device.
  • a display apparatus that includes an organic light- emitting device according to one embodiment of the present invention can stably display high-quality images for a long period of time.
  • the compound was identified by M+ at 1237 by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) .
  • the compound was identified by M+ at 1237 by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) .
  • Fig. 2 also shows the result of Ir(Pim) 3 as a comparative example. Two spectra were superposed with the intensity of the first peak being set at 1.0.
  • the spectrum of the compound pil-1 had the first peak having the maximum intensity at 487 nm and the second peak at approximately 515 nm and had a half-width of 35 nm.
  • Fig. 3 The emission spectrum of a 1 x 10 ⁇ 5 mol/1 toluene solution of the compound pil-1 was measured at 77 K by photoluminescence at an excitation wavelength of 350 nm with F-4500 manufactured by Hitachi, Ltd. (Fig. 3). Fig. 3 also shows the PL measurement of Ir(Pim) 3 under the same conditions as a comparative example. Two spectra were superposed with the maximum intensity of the first peak being set at 1.0.
  • the spectrum of the compound pil-1 had the first peak having the maximum intensity at 491 nm and the second peak at 527 nm.
  • the intensity of the second peak was 0.30 with the maximum intensity of the first peak being 1.0.
  • the spectrum of the comparative compound Ir(Pim) 3 had the first peak having the maximum intensity at 462 nm and the second peak at 495 nm.
  • the intensity of the second peak was 0.62 with the maximum intensity of the first peak being 1.0.
  • the absolute quantum yield of the compound pil-1 in solution was determined to be 0.80 at room temperature with an absolute PL quantum yield measurement system (C9920-02) manufactured by Hamamatsu Photonics K.K.
  • the absolute quantum yield of the compound pil-1 was 1.14 with the absolute quantum yield of the comparative compound Ir(Pim) 3 being 1.00.
  • the light-emitting properties of the compound pil-1 were compared with the light-emitting properties of a common blue-light-emitting complex bIr-01 and a common green-light- emitting complex gIr-01.
  • Fig. 4 also shows the PL measurements of the blue-light- emitting homoleptic complex blr-01 and the green-light- emitting homoleptic complex glr-01 as comparative examples. Three spectra were superposed with the first peak being set at 1.0.
  • the spectrum of the compound pil-1 had the first peak having the maximum intensity at 487 nm and the second peak at approximately 515 nm and had a half-width of 35 nm.
  • the compound blr-01 had the first peak at 468 nm and the second peak having the maximum intensity at 492 nm and had a half- width of 66 nm.
  • the spectrum of the comparative compound glr-01 had the first peak having the maximum intensity at 510 nm and the second peak at approximately 540 nm and had a half-width of 58 nm.
  • the emission spectrum of a 1 x 10 ⁇ 5 mol/1 toluene solution of the compound pil-1 was measured at 77 K by photoluminescence at an excitation wavelength of 350 nm with F-4500 manufactured by Hitachi, Ltd. (Fig. 5).
  • Fig. 5 also shows the PL measurements of bIr-01 and gIr-01 under the same conditions as comparative examples. Three spectra were superposed with the maximum intensity of the first peak being set at 1.0.
  • the spectrum of the compound pil-1 had the first peak having the maximum intensity at 491 nm and the second peak at 527 nm.
  • the intensity of the second peak was 0.30 with the maximum intensity of the first peak being 1.0.
  • the spectrum of the comparative compound bIr-01 had the first peak having the maximum intensity at 460 nm and the second peak at 492 nm.
  • the intensity of the second peak was 0.77 with the maximum intensity of the first peak being 1.0.
  • the spectrum of the comparative compound gIr-01 had the first peak having the maximum intensity at 500 nm and the second peak at 535 nm.
  • the intensity of the second peak was 0.45 with the maximum intensity of the first peak being 1.0.
  • ITO indium tin oxide
  • transparent electroconductive supporting substrate was then subjected to UV/ozone cleaning.
  • the compound 2-1 was then deposited by a vacuum evaporation method to form a hole-transport layer having a thickness of 20 nm.
  • the degree of vacuum was 1.0 x 10 ⁇ 4 Pa, and the deposition rate was 0.1 nm/sec .
  • a host compound 2-2 described below and a guest compound pil-1 were co-evaporated on the hole-transport layer to form a light-emitting layer such that the pil-1 content was 10% by weight of the total weight of the light- emitting layer.
  • the light-emitting layer had a thickness of 40 nm.
  • the degree of vacuum was 1.0 x lCT 4 Pa, and the deposition rate was 0.1 nm/sec.
  • a compound 2-3 described below was then deposited by a vacuum evaporation method to form an electron-transport layer having a thickness of 30 nm.
  • a vacuum evaporation method to form an electron-transport layer having a thickness of 30 nm.
  • the degree of vacuum was 1.0 x 10 ⁇ 4 Pa, and the deposition rate ranged from 0.2 to 0.3 nm/sec.
  • a lithium fluoride film having a thickness of 0.5 nm was formed on the organic layer by a vacuum evaporation method.
  • An aluminum film having a thickness of 150 nm was then formed by a vacuum evaporation method.
  • the organic light-emitting device was covered with a protective glass plate and was sealed with an acrylic resin binder in a dry air atmosphere.
  • the current-voltage characteristics of the organic light-emitting device thus fabricated were measured with a microammeter 4140B manufactured by Hewlett-Packard Co. using an ITO electrode (anode) as a positive electrode and an Al electrode (cathode) as a negative electrode.
  • the luminance was measured with BM7 manufactured by Topcon Co. The luminance was 100 cd/m 2 at an applied voltage of 8.0 V.
  • the external quantum efficiency (O exe ) was 15.0%, indicating highly efficient emission. Blue-green light having the maximum wavelength of 494 nm was observed.
  • An iridium complex according to the present invention is a novel compound that has a high quantum yield and excellent light-emitting properties in a blue to green emission region.
  • An organic light-emitting device that contains the iridium complex has excellent light-emitting properties .
  • the present invention can provide a novel iridium complex having a small half-width of an emission spectrum.
  • the present invention can also provide a novel iridium complex the emission wavelength of which can be altered by the introduction of a substituent into the basic skeleton of the iridium complex.
  • the present invention can also provide an organic light- emitting device that contains any of the novel iridium complexes .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Computer Hardware Design (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention porte sur un nouveau complexe de l'iridium ayant une petite largeur à mi-hauteur dans un spectre d'émission et sur un dispositif électroluminescent organique qui contient le complexe de l'iridium. L'invention porte sur un nouveau complexe de l'iridium qui a un noyau phényle et un noyau imidazole comme ligands et qui a un squelette de base dans lequel le noyau phényle est lié à un noyau triazine.
PCT/JP2010/071754 2009-12-08 2010-11-26 Nouveau complexe de l'iridium, dispositif électroluminescent organique et appareil d'affichage d'images WO2011070991A1 (fr)

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Cited By (1)

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US9768396B2 (en) 2011-12-23 2017-09-19 Semiconductor Energy Laboratory Co., Ltd. Iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device

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JP5900292B2 (ja) * 2012-11-06 2016-04-06 コニカミノルタ株式会社 イミノクロライド誘導体の製造方法及びフェニルイミダゾール誘導体の製造方法
JP6595752B2 (ja) * 2014-11-04 2019-10-23 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、及び照明装置
JP6655873B2 (ja) * 2014-11-04 2020-03-04 株式会社半導体エネルギー研究所 イリジウム錯体、発光素子、発光装置、電子機器、及び照明装置
WO2018189623A1 (fr) * 2017-04-14 2018-10-18 株式会社半導体エネルギー研究所 Complexe organométallique, élément électroluminescent, dispositif électroluminescent, dispositif électronique et dispositif d'éclairage
WO2018212251A1 (fr) * 2017-05-17 2018-11-22 国立研究開発法人産業技術総合研究所 Complexe d'iridium comprenant un ligand phényltriazole et matériau électroluminescent mettant en œuvre ledit composé

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WO2008035571A1 (fr) * 2006-09-20 2008-03-27 Konica Minolta Holdings, Inc. Élément électroluminescent organique
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WO2008035571A1 (fr) * 2006-09-20 2008-03-27 Konica Minolta Holdings, Inc. Élément électroluminescent organique
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US9768396B2 (en) 2011-12-23 2017-09-19 Semiconductor Energy Laboratory Co., Ltd. Iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device

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