WO2013018531A1 - Complexe organométallique et élément électroluminescent comprenant celui-ci - Google Patents

Complexe organométallique et élément électroluminescent comprenant celui-ci Download PDF

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WO2013018531A1
WO2013018531A1 PCT/JP2012/068047 JP2012068047W WO2013018531A1 WO 2013018531 A1 WO2013018531 A1 WO 2013018531A1 JP 2012068047 W JP2012068047 W JP 2012068047W WO 2013018531 A1 WO2013018531 A1 WO 2013018531A1
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light emitting
emitting element
organic light
compound
organometallic complex
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PCT/JP2012/068047
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English (en)
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Masanori Seki
Hiroya Nitta
Kenichi Ikari
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Canon Kabushiki Kaisha
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    • 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
    • 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
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—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
    • C09K2211/10—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
    • 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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to an organometallic complex and an organic light emitting element including the same .
  • An organic light emitting element is an element which includes a pair of electrodes and an organic compound layer arranged therebetween. When electrons and holes are injected from the pair of electrodes, excitons of a
  • luminescent organic compound in the organic compound layer are generated, and when the excitons return to the ground state, light is emitted.
  • NPL 1 an organometallic complex in which a sulfone group is introduced has been disclosed.
  • This organometallic complex is an iridium complex in which phenylpyridine having a sulfone group bonded to its benzene ring and acetylacetone are coordinated.
  • the iridium complex disclosed in PTL 1 has a slightly long emission wavelength and cannot be used as a blue luminescent material.
  • the iridium complex disclosed in PTL 2 has not enough luminescent efficiency.
  • the present invention provides an organometallic complex which emits light in a blue region and which has a high luminescent efficiency .
  • the present invention provides an organometallic complex represented by the following general formula [ 1 ] .
  • R x to R 7 are each independently selected from a hydrogen atom and an alkyl group.
  • the alkyl group indicates an alkyl group having 1 4 carbon atoms.
  • a sulfone group and an ether group of th general formula [1] may bond to each other to form a five- membered ring or a six-membered ring.
  • organometallic complex having a high luminescent efficiency can be provided.
  • organic light emitting element which includes the above organometallic complex and which has a high luminescent efficiency can be provided.
  • Figure 1 is a schematic cross-sectional view showing an organic light emitting element and a switching element connected thereto.
  • the present invention provides an organometallic complex represented by the following general formula [1].
  • Ri to R 7 are each independently selected from a hydrogen atom and an alkyl group.
  • the alkyl group indicates an alkyl group having 1 to 4 carbon atoms.
  • the alkyl group having 1 to 4 carbon atoms indicates 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, or a tert-butyl group.
  • the ether group and the sulfone group adjacent thereto of the general formula [1] may bond to each other to form a five-membered ring or a six-membered ring. That is, Ri and R 2 bond to each other to form a five-membered ring or a six-membered ring. When a five-membered ring is formed, Ri and R 2 collectively represent one carbon atom.
  • the organometallic complex of the present invention has a short emission wavelength and a high luminescent efficiency.
  • the blue region indicates light having a wavelength of 450 to 480 nm.
  • NPL 1 the organometallic complex which uses phenylpyridine having a sulfone group and diketone as ligands has been disclosed.
  • the emission wavelength (actual measurement value) of the organometallic complex described in NPL 1 is shown in the following Table 1.
  • the compound indicated by 4-S02R is the organometallic complex described in NPL 1
  • the compound indicated by a is a compound prepared for
  • the phenyl group in the molecular structure has no alkoxy group.
  • the organometallic complex indicated by a has both a sulfone group and an alkoxy group.
  • the emission wavelength of 4-S02R is 498 nm.
  • a methoxy group is provided at the 5-position adjacent to a sulfone group, so that the emission wavelength is shortened.
  • the emission wavelength of the organometallic complex indicated by a is 480 nm and is shortened by 18 nm as compared to that of 4-S02R.
  • withdrawing property is provided at the 5-position.
  • the compound of the present invention is an
  • organometallic complex having three ligands each identical to each of the two ligands of the organometallic complex indicated by a.
  • the emission wavelength is shortened.
  • the organometallic complex of the present invention has three phenylpyridine ligands each including both a sulfone group and an alkoxy group, blue light
  • the organometallic complex of the present invention has a high quantum yield of light emission in a solution, when this organometallic complex is used as a constituent material of an organic light emitting element, the organic light emitting element can be expected to have a high luminescent efficiency.
  • the organometallic complex of the present invention when used as a luminescent material, a blue organic light emitting element having a high color purity and a high efficiency can be obtained.
  • the ligand is obtained by processing a compound A-l with dimethyl sulfate under a basic condition.
  • a compound A-3 is obtained, for example, when a compound A-2 and bispinacolborane react with each other in the presence of a Pd catalyst.
  • a compound A-5 can be obtained when a compound A-4 react with a pinacolborane compound A-3 in the presence of Pd(PPh 3 ) 4 as a catalyst and sodium carbonate in a mixed solvent of toluene, ethanol, and distilled water.
  • the organometallic complex of the present invention can be synthesized by the following synthetic method using the ligand synthesized, for example, by the above synthetic route .
  • the iridium complex is synthesized through the following three stages.
  • the organic light emitting element according to this embodiment is an organic light emitting element which includes a pair of electrodes, an anode and a cathode, facing each other and at least one organic compound layer arranged therebetween.
  • a layer having a phosphorescent material among the organic compound layers is a light emitting layer.
  • the above organic compound layer contains the organometallic complex represented by the general formula [ 1 ] .
  • the number of the organic compound layers may be one or two or more.
  • the plurality of layers are layers appropriately selected from a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an exciton diffusion blocking layer, and the like.
  • a plurality of layers may be selected from the above group and may be used in combination.
  • an organic light emitting element which has a pair of electrodes, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer may be mentioned.
  • a plurality of light emitting layers may be provided so that respective elements emit different types of color light.
  • a light emitting element having a plurality of light emitting layers may have a plurality of light emitting layers between a pair of electrodes.
  • a structure in which light emitting layers respectively emitting red, green, and blue light are mentioned.
  • the structure of the organic light emitting element according to this embodiment is not limited thereto.
  • various layer structures in which an insulating layer is provided at the interface between the electrode and the organic compound layer, in which an adhesion layer or an interference layer is provided, and in which the electron transport layer or the hole transport layer is formed from two layers having different ionization potentials.
  • any one of a so-called top emission method in which light is extracted from a side opposite to the substrate, a so-called bottom emission method in which light is extracted from a substrate side, and a dual extraction method may be used.
  • the organometallic complex when a plurality of organic compound layers is provided, the organometallic complex may be contained in any layer thereof.
  • the hole injection layer, the hole transport layer, the light emitting layer, the hole blocking layer, or the electron transport layer may be used.
  • the light emitting layer is preferably selected.
  • the light emitting layer of the organic light emitting element according to this embodiment may be formed from only the organometallic compound of the present invention, a host material and a guest material are
  • an assistant material may also be contained.
  • the host material is a compound having the highest weight ratio in the light emitting layer, functioning as a matrix, and being primarily responsible to transport carriers and to supply excitation energy to the guest .
  • the guest material is a compound which has a weight ratio smaller than that of the host material in the light emitting layer and which is responsible for primary light emission .
  • the assistant material is a compound which has a weight ratio smaller than that of the host material in the light emitting layer and which assists light emission of the guest material.
  • the assistant material may also be called a second host material or a host material 2 in some cases.
  • the concentration of the guest material to the whole light emitting layer is preferably 0.1 to 30 percent by weight and more preferably 0.5 to 10 percent by weight.
  • the organic light emitting element according to this embodiment may also use a known low molecular and/or high molecular compound, if needed.
  • a hole injection material or a hole transport material a material having a high hole mobility is
  • a low molecular and a high molecular material having a hole injection ability or a hole transport ability for example, a triarylamine derivative, a
  • phenylenediamine derivative a stilbene derivative, a phthalocyanine derivative, a porphyrin derivative, a poly
  • the host material for example, a triarylamine derivative, a carbazole derivative, a phenylene derivative, a condensed ring aromatic compound (such as a fluorene derivative, a benzene derivative, or a triphenylene
  • an organometallic complex such as an organic aluminum complex including tris ( 8-quinolinolato) aluminum, an organic beryllium complex, an organic iridium complex, or an organic platinum complex
  • a polymer derivative such as a poly (phenylene vinylene) derivatives, a poly ( fluorene) derivative, a poly (phenylene) derivative, a poly (thienylene vinylene) derivative, or a poly (acetylene) derivative, may be mentioned; however, of course, the host material is not limited thereto. As the host material, a compound having a triphenylene derivative is particularly preferable.
  • the triphenylene derivative is a compound having a triphenylene skeleton in its molecular structure.
  • An electron injection material or an electron transport material is selected, for example, in
  • an oxadiazole derivative for example, an oxadiazole derivative, an oxazole derivative, a pyridine derivative, a triazole derivative, a triazine derivative, a quinoline derivative, a quinoxaline derivative, a phenanthroline derivative, and an organic aluminum complex may be
  • an alkali metal such as lithium or cesium
  • an alkaline earth metal such as calcium, or a doped salt thereof may also be used.
  • anode material a material having a work function as high as possible is preferable.
  • metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, alloys formed from the metals mentioned above, and metal oxides, such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide, may be used.
  • ITO indium tin oxide
  • conductive polymers such as a polyaniline, a polypyrrole, and a polythiophene, may also be used. These electrode materials may be used alone, or at least two types thereof may be used in combination.
  • the anode may be formed either from a single layer or a plurality of layers .
  • a cathode material a material having a low work function is preferably used.
  • an alkali metal such as lithium or cesium
  • an alkaline earth metal such as calcium
  • a metal such as aluminum, titanium, manganese, silver, lead, or chromium
  • alloys formed from those metals in combination may also be used.
  • magnesium-silver, aluminum-lithium, and aluminum-magnesium may be used.
  • Metal oxides, such as indium tin oxide (ITO) may also be used. These electrode materials may be used alone, or at least two types thereof may be used in
  • the cathode may be formed either from a single layer or a plurality of layers.
  • the layer including the organometallic complex according to this embodiment and the layer including the other organic compound are formed by the following methods .
  • the layer is formed by a vacuum deposition method, an ionization deposition method, a sputtering method, a plasma deposition method, or a known coating method (such as spin coating, dipping, a casting method, an LB method, or an ink jet method) using an organic compound dissolved in an appropriate solvent.
  • a vacuum deposition method an ionization deposition method, a sputtering method, a plasma deposition method, or a known coating method (such as spin coating, dipping, a casting method, an LB method, or an ink jet method) using an organic compound dissolved in an appropriate solvent.
  • the layer is formed, for example, by a vacuum deposition method or a solution coating method, for example, crystallization is not likely to occur, and a film having excellent aging stability is obtained.
  • a coating method is used for film formation, a film may also be formed in combination with a suitable binder resin.
  • binder resin As the binder resin mentioned above, although a pol (vinyl carbazole) resin, a polycarbonate resin, a polyester resin, an ABS resin, an acrylate resin, a pol (vinyl carbazole) resin, a polycarbonate resin, a polyester resin, an ABS resin, an acrylate resin, a pol (vinyl carbazole) resin, a polycarbonate resin, a polyester resin, an ABS resin, an acrylate resin, a
  • the binder resin is not limited thereto.
  • binder resin a homopolymer or a copolymer may only be used, or at least two types thereof may also be used in combination.
  • additives such as a known plasticizer, antioxidant, and ultraviolet absorber, may also be used, if needed.
  • the organic light emitting element according to this embodiment may be used for a display device and a lighting device.
  • the organic light emitting element according to this embodiment may also be used, for example, for an exposure light source of an image forming device of an electrophotographic system and a backlight of a liquid crystal display device.
  • the display device has the organic light emitting element according to this embodiment in a display portion.
  • This display portion includes a plurality of pixels.
  • the pixels each have the organic light emitting element
  • a TFT element as one example of a switching element controlling the luminescent brightness .
  • the switching element is connected to the anode or the cathode of this organic light emitting element and a drain electrode or a source electrode of the thin film transistor .
  • the display device may be used as an image display device of a personal computer (PC), a head mount display, a mobile phone, or the like.
  • PC personal computer
  • head mount display a mobile phone
  • any image such as a two-dimensional image or a three- dimensional image, may be displayed.
  • the display device may be an image output device which has an input portion to input image information from an area CCD, a linear CCD, a memory card, or the like, and which outputs an inputted image on the display portion.
  • the image output device may be a digital camera having an imaging optical system in which the image input portion is formed of an image sensor, such as a CCD sensor.
  • the display device may have an input function which can perform an input by touching an output image.
  • a touch-panel function may be mentioned.
  • the display device may be used for a display portion of a multifunctional printer.
  • the organic light emitting element according to this embodiment may also be used for a lighting device.
  • the color of light emitted from the lighting device according to this embodiment may be white, natural white, and any other colors.
  • lighting device may also have a compound besides the
  • white and natural white may be a color obtained by mixing a luminescent color of the compound different from that of the compound according to this embodiment.
  • Figure 1 is a schematic cross-sectional view showing the organic light emitting element according to this embodiment and a TFT element, which is one example of a switching element, connected the above organic light
  • the display device shown in Figure 1 includes a substrate 1 formed of a glass or the like and a dampproof film 2 provided thereon to protect the TFT element or the organic compound layer.
  • reference numeral 3 indicates a metal gate electrode.
  • Reference numeral 4 indicates a gate insulating film, and reference numeral 5 indicates a semiconductor layer.
  • a thin film transistor 8 includes the semiconductor layer 5, a drain electrode 6, and a source electrode 7.
  • An insulating film 9 is provided on an upper portion of the thin film transistor 8, and an anode 11 of the organic light emitting element and the source electrode 7 are connected to each other through a contact hole 10.
  • the display device is not limited to that described above and may have any structure as long as the anode or the cathode is connected to one of the source electrode and the drain electrode of the thin film transistor.
  • compound layer 12 is shown as one layer; however, a
  • a first protective layer 14 and a second protective layer 15 are provided to suppress degradation of the organic light emitting element.
  • the switching element is not particularly limited, and a transistor or an MIM element may be used.
  • a transistor or an MIM element may be used as the transistor.
  • the transistor for example, a thin film transistor using single crystal silicon or an amorphous-silicon type transistor element may be used.
  • the thin film transistor is also called a TFT element .
  • the luminescent brightness of the organic light emitting element is controlled by the switching element.
  • control may also be performed in such a way that active matrix drivers are formed on a Si substrate, and the organic light emitting elements are provided thereon.
  • the structure may be selected depending on the fineness, and for example, when the fineness is
  • reaction solution was heated to 190°C under a nitrogen stream and stirred for 6 hours. After the reaction solution was cooled to room temperature, a precipitate precipitated by addition of water was separated by
  • the emission maximum wavelength was 467 nm.
  • a spectrophotometer F-4500 manufactured by Hitachi Co., Ltd. was used for this measurement.
  • ultraviolet-visible spectrophotometer V-560 manufactured by JASCO Corporation.
  • Example compound (10) was synthesized in a manner similar to that of Example 1 except that the compound A-3 was changed to the following compound A-8.
  • an organic light emitting element having the structure in which an anode/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/cathode were
  • An ITO film having a thickness of 120 nm was formed as an anode on the glass substrate by a sputtering method and was used as a transparent conductive support substrate
  • Electron blocking layer (10 nm) A-ll
  • Light emitting layer (30 nm) host material 1: A-12, guest material: example compound (2) (10 percent by weight)
  • Metal electrode layer 1 (0.5 nm) : LiF
  • Metal electrode layer 2 (100 nm) : aluminum
  • the luminescent efficiency was 12.2 lm/W, and blue light emission was observed.
  • An organic light emitting element was formed in a manner similar to that of Example 4 except that the guest material was changed to the example compound (10).
  • the luminescent efficiency was 12.0 lm/W, and blue light emission was observed.
  • the organometallic complex of the present invention emits light in a blue region and has a high luminescent efficiency. Therefore, when this
  • organometallic complex is used for an organic light emitting element, an organic light emitting element having a high luminescent efficiency can be obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un complexe organométallique utile en tant que matériau hôte d'un élément électroluminescent phosphorescent bleu. De plus, la présente invention concerne en outre un élément électroluminescent organique ayant une efficacité luminescente élevée. La présente invention concerne un complexe organométallique selon la revendication 1 représenté par la formule générale [1]. Dans la formule générale [1], R1 à R7 sont chacun indépendamment choisis parmi un atome d'hydrogène et un groupe alkyle. Le groupe alkyle indique un groupe alkyle ayant 1 à 4 atomes de carbone. Un groupe sulfone et un groupe éther dans la formule générale [1] peuvent se lier mutuellement de manière à former un cycle de cinq chaînons ou un cycle de six chaînons.
PCT/JP2012/068047 2011-07-29 2012-07-10 Complexe organométallique et élément électroluminescent comprenant celui-ci WO2013018531A1 (fr)

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JP2011166968A JP2013028757A (ja) 2011-07-29 2011-07-29 有機金属錯体及びこれを有する有機発光素子
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Cited By (1)

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US20180240987A1 (en) * 2017-02-22 2018-08-23 Universal Display Corporation Organic electroluminescent materials and devices

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