WO2011070989A1 - Nouveau complexe d'iridium et dispositif électroluminescent organique comprenant celui-ci - Google Patents

Nouveau complexe d'iridium et dispositif électroluminescent organique comprenant celui-ci Download PDF

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WO2011070989A1
WO2011070989A1 PCT/JP2010/071752 JP2010071752W WO2011070989A1 WO 2011070989 A1 WO2011070989 A1 WO 2011070989A1 JP 2010071752 W JP2010071752 W JP 2010071752W WO 2011070989 A1 WO2011070989 A1 WO 2011070989A1
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Prior art keywords
iridium complex
compound
group
emitting device
organic light
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PCT/JP2010/071752
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English (en)
Inventor
Chiaki Nishiura
Masashi Hashimoto
Shigemoto Abe
Hiroya Nitta
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Canon Kabushiki Kaisha
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Priority to EP10835909.2A priority Critical patent/EP2509987A4/fr
Priority to US13/514,025 priority patent/US8980444B2/en
Priority to CN201080055620.5A priority patent/CN102648205B/zh
Publication of WO2011070989A1 publication Critical patent/WO2011070989A1/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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System 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
    • 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
    • C09K2211/1003—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
    • C09K2211/1044—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
    • C09K2211/18—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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to a novel iridium complex and an organic light-emitting device including the novel iridium complex.
  • a compound represented by the structural formula above has a weak ligand field and such a compound is not expected to have good emission characteristics as a blue light-emitting material.
  • the present invention provides an iridium complex that emits blue phosphorescence and has good emission characteristics.
  • An organic light-emitting device including such an iridium complex and having a high external quantum yield is also provided.
  • An aspect of the present invention provides an iridium complex represented by general formula (1):
  • Ri and R 2 each independently represent a group selected from a tert-butyl group, an adamantyl group, and a bicyclooctyl group;
  • R 3 represents one selected from a hydrogen atom, a halogen atom, and a cyano group;
  • R 4 and R 5 each independently represent one selected from a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, and an amino group; and
  • R 6 represents an alkyl group.
  • Fig. 1 is an emission spectrum diagram of Compound 1-1 according to an example of the present invention.
  • Fig. 2 is an emission spectrum diagram of Compound 9 according to a comparative example.
  • Fig. 3 is a schematic cross-sectional view of an organic light-emitting device and a TFT element which is a switching element coupled to the organic light-emitting device .
  • An iridium complex according to an embodiment of the present invention is represented by general formula ( 1 ) below.
  • Rj . and R 2 each independently represent a group selected from a tert-butyl group, an adamantyl group, and a bicyclooctyl group.
  • R 3 represents one selected from a hydrogen atom, a halogen atom, and a cyano group.
  • R 4 and R 5 each independently represent one selected from a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, and an amino group.
  • R 6 represents an alkyl group.
  • Examples of the halogen atom represented by R 3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Substituents R 4 and R 5 may be the same as or different from each other.
  • Examples of the halogen atom represented by R 4 and R 5 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the alkyl group represented by R 4 and R 5 include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and an adamantyl group.
  • Examples of the alkoxy group represented by R and R 5 include a methoxyl group, an ethoxyl group, and a phenoxyl group.
  • Examples of the amino group represented by R4 and R 5 include a dimethylamino group and a
  • R 6 include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and an adamantyl group.
  • the iridium complex represented by general formula ( 1 ) has a ligand that has a skeleton in which a triazine ring, a phenyl ring, and a pyrazole ring excluding Rj. to R 6 and H are linked at particular sites .
  • This skeleton is hereinafter referred to as "the ligand backbone in general formula (1)".
  • the iridium complex emits blue phosphorescence .
  • ligand structures A to D There are four possible ligand structures A to D below constituted by a triazine ring, a phenyl ring, and a pyrazole ring.
  • the structure C i.e., the ligand backbone in general formula ( 1 )
  • the ligand backbone is the favored backbone for blue light-emitting materials.
  • ⁇ back donation is donation of electrons from the center metal of the complex to the ligand.
  • the inventors have realized that there are two crucial requirements for the ⁇ back donation derived from the electron-attracting triazine ring to work effectively.
  • the structures A to D above all include iridium, a pyrazole ring, a phenyl ring, and a triazine ring.
  • Requirement 1 The substitution site of the triazine ring bonded to the phenyl group bonded to iridium is at the ortho or para position on the phenyl ring with respect to iridium.
  • Requirement 2 The triazine ring is coplanar with the phenyl ring. [0023] In the structure B, iridium and the triazine ring are at meta positions on the phenyl ring and thus the structure B does not satisfy the requirement 1.
  • the coplanarity between the phenyl ring and the triazine ring cannot be sterically maintained due to the steric repulsion between the iridium atom and the triazine ring at adjacent bonding sites in the structure A and the steric repulsion between the pyrazole ring and the triazine ring at adjacent bonding sites in the structure D.
  • the structures A and D do not satisfy the requirement 2.
  • Two hydrogen atoms of the phenyl ring i.e., two H in general formula ( 1 ) , are important for maintaining the coplanarity of the triazine ring and the phenyl ring.
  • the two ortho positions on the phenyl ring with respect to the triazine ring may be occupied by hydrogen atoms in order to maintain the coplanarity of the triazine ring and the phenyl ring.
  • Ri and R 2 in general formula (1) are each
  • Substituents R x and R 2 are provided to protect the triazine ring. Thus, it is important that the substituents Ri and R 2 be bulky.
  • R x and R 2 each
  • Ri and R 2 may each independently represent a tert-butyl group.
  • Concentration quenching is a phenomenon in which the emission efficiency decreases at a high concentration.
  • R 6 in general formula (1) represents an alkyl group. This means that R 6 is not a hydrogen atom.
  • R 6 is a hydrogen atom, by-products derived from hydrogen tautomers occur during the synthesis of the complex.
  • a substituent having a small excluded volume is preferred. For example, a methyl group is preferred.
  • the iridium complex of this embodiment can be used as a blue phosphorescence emitting-material.
  • the iridium complex is suitable as a light-emitting material of an organic light-emitting device.
  • the organic light- emitting device is described below.
  • the iridium complex of this embodiment has a band gap sufficient for use as a host material of an emission layer of an organic light-emitting device that emits green or red light.
  • Example compound 1-1 Example compound 1-2
  • Example compound 1-3 Example compound 1-1
  • Example compound 2-1 Example compound 2-2
  • Example compound 2-3 Example compound 2-3
  • Example compound 2-4 Example compound 2-5
  • Example compound 2-6 Example compound 2-6
  • Example compound 3-4 Example compound 3-5
  • Example compound 3-6 Example compound 3-6
  • Example compound 4-4 Example compound 4-5
  • Example compound 4-6 Example compound 4-6
  • the iridium complex of this embodiment can be used as a material for an organic light-emitting device.
  • the iridium complex may be used as a guest or host material of an emission layer of an organic light-emitting device.
  • the organic light-emitting device includes a pair of electrodes opposing each other and an emission layer interposed between the electrodes.
  • the organic light-emitting device may further include a layer or layers other than the emission layer.
  • the iridium complex of this embodiment can be used in the emission layer and any of layers other than the emission layer, i.e., an electron transport layer, an
  • a host material is a material that has the largest weight ratio among compounds constituting the emission layer and a guest material is a material that has a weight ratio smaller than that of the host material among the compounds constituting the emission layer.
  • the iridium complex of this embodiment may be used as a guest material of an emission layer of an organic light-emitting device.
  • the iridium complex is preferably used as a guest material of a blue light- emitting device.
  • the emission wavelength can be changed by
  • a host material having a higher LUMO level than the iridium complex i.e., a host material having a LUMO level closer to the vacuum level
  • LUMO level is an abbreviation of a lowest unoccupied molecular orbital level
  • HOMO level is an abbreviation of a highest occupied molecular orbital level- Further descriptions of the host material and the guest material are provided below.
  • the halide used as a raw material is not limited to one into which bromine is introduced and may be, for example, one into which iodine or triflate is introduced.
  • product may be boronic acid, for example.
  • Various ligands can be synthesized by choosing the halogenated triazine synthesized in Scheme 1 and the boronic acid derivative having a 3-phenylpyrazole backbone
  • a protic solvent having a high boiling point such as ethylene glycol and glycerol, is preferred.
  • ethylene glycol or glycerol may be used or no solvent may be used.
  • An organic light-emitting device includes a pair of electrodes and an organic compound layer interposed between the pair of electrodes.
  • the pair of electrodes may be an anode and a cathode.
  • a forward electric field necessary for causing emission and a reverse electric field may be applied to the pair of electrodes .
  • the organic compound layer contains the iridium complex of an embodiment .
  • the organic light-emitting device may further include an organic compound layer or layers in addition to this organic compound layer.
  • the organic light-emitting element includes an emission layer between the anode and the cathode.
  • emission layer may be the organic compound layer containing the iridium complex or may be constituted by the organic compound layer containing the iridium complex and a
  • the organic compound layer containing the iridium complex may be an emission layer or a layer other than the emission layer.
  • a hole injection layer, a hole transport layer, a hole/exciton blocking layer, an electron transport layer, and an electron injection layer may contain the iridium complex.
  • the combination of the organic compound layer containing the iridium complex and other organic compound layers may be adequately selected.
  • the number of other organic compound layers may be two or more.
  • a first layer arrangement includes an anode, an emission layer, and a cathode stacked in that order.
  • a second layer arrangement includes an anode, a hole transport layer, an electron transport layer, and a cathode stacked in that order. If emission is observed between the hole
  • a third layer arrangement includes an anode, a hole transport layer, an emission layer, an electron transport layer, and a cathode stacked in that order.
  • a fourth layer arrangement include an anode, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and a cathode stacked in that order.
  • a fifth layer arrangement includes an anode, a hole transport layer, an emission layer, a hole/exciton blocking layer, an electron transport layer, and a cathode stacked in that order.
  • the iridium complex of this embodiment may be used in one of the layers in the first to fifth layer
  • injection layer or the hole transport layer may be a
  • the organic compound may be a low-molecular compound or a high-molecular compound.
  • Examples of the organic compound include triarylamine
  • poly(vinyl carbazole), poly( thiophene) , and other conductive polymers examples thereof are as follows .
  • the organic compound included in the electron injection layer or the electron transport layer is selected by considering the balance between the hole mobility of the compound included in the hole injection layer or the hole transport layer and that of the organic compound included in the electron injection layer or the electron transport layer. Examples thereof include oxadiazole derivatives , oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, and organic
  • aluminum complexes examples thereof are as follows :
  • the emission layer may include one organic compound or two or more organic compounds .
  • the emission layer may be a host material and a guest material.
  • a host material is a main component of the emission layer and its weight ratio is larger than that of the guest material.
  • the amount of the guest material, which is the auxiliary component, relative to the total weight of the emission layer is 0.01 wt.% or more and 20 wt.% or less and preferably 0.5 wt.% or more and 10 wt.% or less.
  • the guest material may be an emission material that determines the color of emission.
  • the emission layer includes two or more organic compounds , they may be a host material, a guest material, an emission assisting material, and a charge injection material.
  • the host material may be a material in which carriers of both holes and electrons move smoothly.
  • the host material may be a material that has a lowest triplet excitation energy level Tl higher than that of the emission material in order to efficiently use the excitons generated in the emission layer for emission.
  • Examples of the host material include fused compounds (e.g., fluorene derivatives, naphthalene derivatives, carbazole derivatives, quinoxaline derivatives, and quinoline
  • organic aluminum complexes such as tris(8- quinolinolato) aluminum, organic zinc complexes, and polymer derivatives such as triphenylamine derivatives ,
  • poly( fluorene) derivatives and poly(phenylene) derivatives. Examples thereof are as follows :
  • a material having a work function as large as possible may be used in the anode.
  • a material having a work function as large as possible include single metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten or alloys thereof, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide.
  • Conductive polymers such as polyaniline, polypyrrole, and polythiophene may also be used. These electrode substances may be used alone or in combination.
  • the anode may be constituted by one layer or two or more layers .
  • the cathode may be composed of a material having a small work function.
  • a material having a small work function examples include alkali metals such as lithium, alkaline earth metals such as calcium, and single metals such as aluminum, titanium, manganese, silver, lead, and chromium.
  • the single metals may be combined and used as alloys .
  • magnesium- silver, aluminum-lithium, and aluminum-magnesium alloys and the like can be used.
  • Metal oxides such as indium tin oxide (ITO) can also be used. These electrode substances may be used alone or in combination.
  • the cathode may be
  • containing the iridium complex and other layers containing organic compounds include thin-film forming methods such as vacuum vapor deposition, ionization deposition, sputtering, plasma coating, and coating using an adequate solvent (spin- coating, dipping, casting, a Langmuir Blodgett method, and an ink jet method) .
  • thin-film forming methods such as vacuum vapor deposition, ionization deposition, sputtering, plasma coating, and coating using an adequate solvent (spin- coating, dipping, casting, a Langmuir Blodgett method, and an ink jet method) .
  • layers When layers are formed by coating, layers may be formed by using an adequate binder resin in combination.
  • binder resin examples include
  • polyvinylcarbazole resins polycarbonate resins , polyester resins, ABS resins, acrylic resins, polyimide resins, phenolic resins, epoxy resins, silicone resins, and urea resins . These binder resins may be used alone as a
  • antioxidant and an ultraviolet absorber may be used in combination .
  • the organic light-emitting device can also be used as exposure light sources of image-forming apparatuses and backlights of liquid crystal display apparatuses .
  • a display apparatus includes a display unit that includes the organic light-emitting device of this
  • the display apparatus can display images by using the organic light-emitting device.
  • the display unit may include pixels and each pixel may include the organic light-emitting device of this embodiment .
  • the display apparatus can be used as an image display apparatus of a personal computer, etc.
  • the display apparatus may be used in a display unit of an imaging apparatus such as digital cameras and digital video cameras .
  • An imaging apparatus includes the display unit and an imaging unit having an imaging optical system for capturing images.
  • a display apparatus may include an image input unit and a display unit .
  • the image input unit may be an imaging optical system mentioned above, a light-detecting unit such as a charge coupled device (CCD), a unit that receives a memory card or the like, a scanner, or the like.
  • a light-detecting unit such as a charge coupled device (CCD)
  • CCD charge coupled device
  • Examples of the apparatuses that have the organic light-emitting device of the embodiment in the display unit include digital cameras and digital video cameras described above, and multifunctional image-forming apparatuses that have a scanner function and an image output function.
  • multifunctional image-forming apparatus may be an image- forming apparatus of an ink jet type or an
  • Fig. 3 is a schematic cross-sectional view of a display apparatus showing an organic light-emitting device functioning as a pixel and a switching element coupled to the organic light-emitting device.
  • the switching element is a thin film transistor (TFT) element.
  • the switching element may be a metal- insulator-metal (MIM) element.
  • a display apparatus 3 includes a substrate 31 composed of, for example, glass and a moisture-proof film 32 for protecting the TFT element or the organic compound layer on the substrate 31.
  • the display apparatus 3 also includes a metal gate electrode 33 composed of chromium or the like and a gate insulating film 34.
  • a TFT element 38 includes a semiconductor film 35, a drain electrode 36, and a source electrode 37.
  • the source electrode 37 is connected to an anode 311 of an organic light-emitting device through a contact hole
  • An organic compound layer 312 is illustrated in the drawing as a single layer for the purposes of simplification but is a multilayer organic compound layer.
  • protective layer 314 and a second protective layer 315 are provided on a cathode 313 to suppress deterioration of the organic light-emitting device.
  • the luminance of the light emitted from the organic light-emitting device is controlled by the TFT element.
  • an image can be displayed by controlling the luminance of the emission.
  • MALDI-TOF-MS matrix- assisted laser desorption ionization-time-of-flight mass spectroscopy
  • Example compound 1-1 The emission spectrum of Example compound 1-1 at room temperature was measured. Measurement was conducted using 1 ⁇ 10 "5 mol/1 toluene solution and F-4500 produced by Hitachi Corporation at an excitation wavelength of 350 nm. Example compound 1-1 had a spectrum that has a maximal wavelength at 468 nm at room temperature. The half width of the emission spectrum was 47 nm and the chroma according to Commission Internationale d'Eclairage (CIE) standard
  • This compound also has an emission maxima at 468 nm.
  • Example compound 1-1 has a half width 19 nm smaller than that of compound 9.
  • NTSC National Television System Committee
  • a glass substrate with an anode formed by sputter- depositing indium tin oxide (ITO) to a thickness of 120 nm was used as a transparent conductive support substrate.
  • the substrate was ultrasonically washed with acetone and then with isopropyl alcohol (IPA), washed with boiling IPA, and then dried. The substrate was then subjected to UV/ozone washing and used as the transparent conductive support substrate .
  • ITO indium tin oxide
  • a hole injection layer 30 nm in thickness was formed on the transparent conductive support substrate by spin-coating with a chloroform solution of compound 10.
  • Metal electrode layer 1 (0.5 nm) : LiF Metal electrode layer 2 (150 nm) : Al
  • the properties of the obtained organic light- emitting device were measured.
  • the current- voltage characteristic of the device was measured with a pA meter 4140B produced by Hewlett-Packard Company, and the luminance of the emission from the organic light-emitting device was measured with BM7 produced by Topcon Corporation.
  • a high emission efficiency of 21.4 cd/A and an external quantum yield of 9.6% were achieved.
  • the iridium complexes according to embodiments of the present invention are novel compounds that offer high quantum yields and exhibit emission suitable for blue.
  • Organic light-emitting devices having good emission characteristics can be formed by using these iridium complexes .
  • the present invention provides an iridium complex that has good blue emission characteristics .
  • An organic light-emitting device having good emission characteristics is also provided.

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

Abstract

La présente invention concerne un nouveau complexe d'iridium qui comprend un ligand comprenant un cycle phényle et un cycle pyrazole. Le groupe phényle est lié à un cycle triazine pour former un squelette du nouveau complexe d'iridium. Un dispositif électroluminescent organique comprend le nouveau complexe d'iridium.
PCT/JP2010/071752 2009-12-08 2010-11-26 Nouveau complexe d'iridium et dispositif électroluminescent organique comprenant celui-ci WO2011070989A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP10835909.2A EP2509987A4 (fr) 2009-12-08 2010-11-26 Nouveau complexe d'iridium et dispositif électroluminescent organique comprenant celui-ci
US13/514,025 US8980444B2 (en) 2009-12-08 2010-11-26 Iridium complex and organic light-emitting device including the same
CN201080055620.5A CN102648205B (zh) 2009-12-08 2010-11-26 铱络合物和包括该化合物的有机发光器件

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JP2009278967A JP5495746B2 (ja) 2009-12-08 2009-12-08 新規イリジウム錯体とそれを有する有機発光素子
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US9711741B2 (en) 2012-08-24 2017-07-18 Arizona Board Of Regents On Behalf Of Arizona State University Metal compounds and methods and uses thereof
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
US10033003B2 (en) 2014-11-10 2018-07-24 Arizona Board Of Regents On Behalf Of Arizona State University Tetradentate metal complexes with carbon group bridging ligands
US10056567B2 (en) 2014-02-28 2018-08-21 Arizona Board Of Regents On Behalf Of Arizona State University Chiral metal complexes as emitters for organic polarized electroluminescent devices
US10158091B2 (en) 2015-08-04 2018-12-18 Arizona Board Of Regents On Behalf Of Arizona State University Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof
US10177323B2 (en) 2016-08-22 2019-01-08 Arizona Board Of Regents On Behalf Of Arizona State University Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues
EP3447062A1 (fr) * 2017-08-21 2019-02-27 Samsung Display Co., Ltd. Composé organométallique, dispositif électroluminescent organique comprenant le composé organométallique et appareil électroluminescent organique comprenant le dispositif électroluminescent organique
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CN102648205B (zh) 2015-11-25
EP2509987A4 (fr) 2014-09-17
JP5495746B2 (ja) 2014-05-21
JP2011121875A (ja) 2011-06-23
EP2509987A1 (fr) 2012-10-17
US8980444B2 (en) 2015-03-17
CN102648205A (zh) 2012-08-22

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