WO2005124890A1 - Complexe d'iridium electroluminescent et dispositifs fabriques a l'aide dudit compose - Google Patents

Complexe d'iridium electroluminescent et dispositifs fabriques a l'aide dudit compose Download PDF

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Publication number
WO2005124890A1
WO2005124890A1 PCT/US2005/020449 US2005020449W WO2005124890A1 WO 2005124890 A1 WO2005124890 A1 WO 2005124890A1 US 2005020449 W US2005020449 W US 2005020449W WO 2005124890 A1 WO2005124890 A1 WO 2005124890A1
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Prior art keywords
layer
compound
layers
host
organic
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PCT/US2005/020449
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English (en)
Inventor
Norman Herron
Nora Sabina Radu
Klaus Mullen
Eric Maurice Smith
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E.I. Dupont De Nemours And Company
Max Planck Institute For Polymer Research
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Publication of WO2005124890A1 publication Critical patent/WO2005124890A1/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
    • 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
    • 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
    • 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
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • This invention relates to organometallic compounds, and more particularly to semiconductor and photoactive organometallic compounds. It also relates to electronic devices in which an active layer includes at least one such organometallic compound.
  • an active layer includes at least one such organometallic compound.
  • the organic active layer emits light through the light-transmitting electrical contact layer upon application of electricity across the electrical contact layers.
  • organic electroluminescent compounds as the active component in light-emitting diodes. Simple organic molecules such as anthracene, thiadiazole derivatives, and coumarin derivatives are known to show electroluminescence.
  • Semiconductive conjugated polymers have also been used as electroluminescent components, as has 25 been disclosed in, for example, Friend et al., U.S. Patent 5,247,190, Heeger et al., U.S. Patent 5,408,109, and Nakano et al., Published European Patent Application 443 861.
  • OLEDs organic light emitting diodes
  • electroluminescent devices containing at least one active layer including the invention compound.
  • Figure 1 is a schematic diagram of one illustrative example of a light-emitting device.
  • the compound of the invention has the following formula which may exist in either facial (fac) or mehdonal (mer) isomeric forms:
  • the compound of the present invention can be formed into films by any conventional means and may be used in a composition.
  • the compound is deposited by solution processing.
  • liquid or solution processing or solution deposition refers to the formation of uniform films from a liquid medium.
  • the film is robust.
  • the deposition techniques include any continuous or discontinuous method of depositing a material that is in the form of a liquid medium.
  • layer is used interchangeably with the term “film” and refers to a coating covering a desired area. The term is not limited by size. For example, in some embodiments, the area can be as large as an entire device.
  • the area can be as small as a specific functional area such as the actual visual display, or as small as a single sub-pixel.
  • the area can be continuous or discontinuous.
  • Layers can be formed by any conventional deposition technique, including, but not limited to, vapor deposition, liquid deposition, and thermal transfer.
  • the layer may be made by] spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, continuous nozzle coating, and discontinuous deposition techniques such as ink jet printing, contact printing such as gravure printing, screen printing, and the like, or indeed, any other way which is effective in causing a layer to come into existence.
  • the liquid medium for solution processing the new compound can be any organic or partially organic liquid in which the compound can be dissolved or dispersed.
  • the liquid medium is non-aqueous.
  • suitable organic liquids which can be used as the liquid medium include, but are not limited to, toluene, xylenes, chlorinated hydrocarbons, ethylacetate, and 4-hydroxy-4-methyl-2-pentanone.
  • the compound of Formula I can be prepared by the reaction of iridium trichloride hydrate, an excess of ligand, and silver trifluoroacetate.
  • the ligand can generally be prepared using the Suzuki coupling of the component groups, as described in O. Lohse, P.Thevenin, E.
  • the compounds of the invention can be isolated, purified, and fully characterized by elemental analysis, 1 H and 19 F NMR spectral data, and, for suitable crystalline compounds, single crystal X-ray diffraction.
  • Electronic Device Another embodiment is a new organic electronic device comprising at least one layer comprising the above compound of Formula I. The compound can be in a separate layer or can be combined with other active or inactive materials in the device.
  • the emissive layer comprises a host transport material into which the electroluminescent material is doped at ⁇ 20 wt %.
  • good miscibility between the host and electroluminescent material is needed to obtain good film quality.
  • the addition of at least one solvent-solubilizing substituent can improve compatibility of the metal compound and the host and result in high-quality films which retain amorphous character and inhibit phase segregation or emitter aggregation in the host.
  • An illustration of one type of organic electronic device structure is shown in Figure 1.
  • the device 100 has an anode layer 110 and a cathode layer 150. Adjacent to the anode is a layer 120 comprising hole transport material.
  • the photoactive layer 130 Adjacent to the cathode is a layer 140 comprising an electron transport material. Between the hole transport layer and the electron transport layer is the photoactive layer 130.
  • the photoactive layer 130 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell, light-emitting display), a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
  • Electronic devices that benefit from the use of this invention include (1 ) devices that convert electrical energy into radiation (e.g., a light-emitting diode, light-emitting diode display, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes), IR detectors), (3) devices that convert radiation into electrical energy (e.g., a photovoltaic device or solar cell), and (4) devices that include one or more electronic components that include one or more organic semi-conductor layers (e.g., a transistor or diode).
  • devices that convert electrical energy into radiation e.g., a light-emitting diode, light-emitting diode display, or diode laser
  • devices that detect signals through electronics processes e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, photo
  • the compounds of the invention are particularly useful as the photoactive material in layer 130, or as electron transport material in layer 130 or layer 140.
  • the compounds of the invention are used as the light-emitting material in diodes.
  • a layer that is greater than 20% by weight new compound, based on the total weight of the layer, up to 100% new compound, can be used as the emitting layer. Additional materials can be present in the emitting layer with the compound of the invention. For example, a fluorescent dye may be present to alter the color of emission.
  • a diluent may also be added and such diluent may be a charge transport material or an inert matrix.
  • a diluent may comprise polymeric materials, small molecule or mixtures thereof.
  • a diluent may act as a processing aid, may improve the physical or electrical properties of films containing the new compound, may decrease self-quenching in the new compound described herein, and/or may decrease the aggregation of the new compound described herein.
  • the new compound of Formula I is present as a guest material in a host material.
  • guest material is intended to mean a material, within a layer including a host material, that changes the electronic characteristic(s) or the targeted wavelength(s) of radiation emission, reception, or filtering of the layer compared to the electronic characteristic(s) or the wavelength(s) of radiation emission, reception, or filtering of the layer in the absence of such material.
  • host material is intended to mean a material, usually in the form of a layer, to which a guest material may or may not be added.
  • the host material may or may not have electronic characteristic(s) or the ability to emit, receive, or filter radiation.
  • suitable polymeric host materials include poly(N-vinyl carbazole), conjugated polymers, and polysilanes and mixtures thereof.
  • suitable small molecules host materials include 4,4'-N,N'-dicarbazole biphenyl (CBP), Bis(2-methyl-8- quinolinolato)(4-phenyIphenolato)aluminum (BAIQ) or tertiary aromatic amines and mixtures thereof.
  • conjugated polymers examples include polyarylenevinylenes, polyfluorenes, polyoxadiazoles, polyanilines, polythiophenes, polyphenylenes, copolymers thereof and combinations thereof.
  • the conjugated polymer can be a copolymer having non- conjugated portions, for example, acrylic, methacrylic, or vinyl monomeric units.
  • the host comprises homopolymers and copolymers of fluorine and substituted fluorenes. When a host is used, the compound of the invention is generally present in a small amount. In one embodiment, the new compound is less than 20% by weight, based on the total weight of the layer. In one embodiment, the new compound is less than 10% by weight, based on the total weight of the layer.
  • the HOMO (highest occupied molecular orbital) of the hole transport material should align with the work function of the anode
  • the LUMO (lowest un-occupied molecular orbital) of the electron transport material should align with the work function of the cathode.
  • Chemical compatibility and sublimation temp of the materials are also important considerations in selecting the electron and hole transport materials.
  • the other layers in the OLED can be made of any materials which are known to be useful in such layers.
  • the anode 110 is an electrode that is particularly efficient for injecting positive charge carriers. It can be made of, for example, materials containing a metal, mixed metal, alloy, metal oxide or mixed-metal oxide, or it can be a conducting polymer.
  • Suitable metals include the Group 11 metals, the metals in Groups 4, 5, and 6, and the Group 8-10 transition metals. If the anode is to be light-transmitting, mixed-metal oxides of Groups 12, 13 and 14 metals, such as indium-tin- oxide, are generally used. The IUPAC numbering system is used throughout, where the groups from the Periodic Table are numbered from left to right as 1-18 (CRC Handbook of Chemistry and Physics, 81 st Edition, 2000).
  • the anode 110 may also comprise an organic material such as polyaniline as described in "Flexible light-emitting diodes made from soluble conducting polymer," Nature vol. 357, pp 477-479 (11 June 1992).
  • At least one of the anode and cathode should be at least partially transparent to allow the generated light to be observed.
  • Examples of hole transport materials for layer 120 have been summarized for example, in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, p. 837-860, 1996, by Y. Wang. Both hole transporting molecules and polymers can be used.
  • hole transporting molecules are: N,N'-diphenyl-N,N'-bis(3-methylphenyl)- [1 ,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-Bis[N-(1-naphthyl)-N- phenylaminojbiphenyl (NPB, NPD) 1 ,1-bis[(di-4-tolylamino) phenyljcyclohexane (TAPC), N,N'-bis(4-methylphenyl)-N,N'-bis(4- ethylphenyl)-[1 ,i ⁇ 3,3'-dimethyl)biphenyl]-4,4'-diamine (ETPD), tetrakis-(3- methylphenyl)-N,N,N',N'-2,5-phenylenediamine (PDA), a-phenyl-4-N,N- diphenyl
  • hole transporting polymers are polyvinylcarbazole, (phenylmethyl)polysilane, and polyaniline. It is also possible to obtain hole transporting polymers by doping hole transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate.
  • Examples of other electron transport materials for layer 140 include metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq 3 ); phenanthroline-based compounds, such as 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline (DDPA) or 4,7-diphenyl-1 ,10-phenanthroline (DPA), and azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (PBD) and 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1 ,2,4-triazole (TAZ).
  • metal chelated oxinoid compounds such as tris(8-hydroxyquinolato)aluminum (Alq 3 )
  • phenanthroline-based compounds such as 2,9-dimethyl-4,7-diphenyl-1
  • the cathode 150 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
  • the cathode can be any metal or nonmetal having a lower work function than the anode.
  • Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides.
  • Li-containing organometallic compounds can also be deposited between the organic layer and the cathode layer to lower the operating voltage. It is known to have other layers in organic electronic devices. For example, there can be additional layers(not shown) between the anode layerl 10 and the active layer 130 to facilitate positive charge transport and/or band-gap matching of the layers, or to function as a protective layer. Similarly, there can be additional layers (not shown) between the active layer 130 and the cathode layer 150 to facilitate negative charge transport and/or band-gap matching between the layers, or to function as a protective layer. Layers that are known in the art can be used.
  • any of the above-described layers can be made of two or more layers.
  • some or all of inorganic anode layer 110, the hole transporting layer 120, the active layer 130, and cathode layer 150 may be surface treated to increase charge carrier transport efficiency.
  • the choice of materials for each of the component layers is preferably determined by balancing the goals of providing a device with high device efficiency. It is understood that each functional layer may be made up of more than one material layer.
  • the device can be prepared by sequentially vapor depositing the individual layers on a suitable substrate. Substrates such as glass and polymeric films can be used. Conventional vapor deposition techniques can be used, such as thermal evaporation, chemical vapor deposition, and the like.
  • the organic layers can be coated from solutions or dispersions in suitable solvents, using any conventional coating technique.
  • the different layers will have the following range of thicknesses: anode 110, 500-5000A, preferably 1000-2000A; hole transport layer 120, 50-1000A, preferably 200-800A; light-emitting layer 130, 10-1000 A, preferably 100-800A; electron transport layer 140, 50-1 OOOA, preferably 200-800A; cathode 150, 200-1 OOOOA, preferably 300-5000A.
  • the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer.
  • the thickness of the electron-transport layer should be chosen so that the electron-hole recombination zone is in the light-emitting layer.
  • the desired ratio of layer thicknesses will depend on the exact nature of the materials used. It is understood that the efficiency of devices made with the compound of the invention, can be further improved by optimizing the other layers in the device. For example, more efficient cathodes such as Ca, Ba or LiF can be used. Shaped substrates and novel hole transport materials that result in a reduction in operating voltage or increase quantum efficiency are also applicable. Additional layers can also be added to tailor the energy levels of the various layers and facilitate electroluminescence. The compound of the invention may be useful in applications other than OLEDs.
  • organometallic compounds have been used as oxygen sensitive indicators, as phosphorescent indicators in bioassays, and as catalysts.
  • compound is intended to mean an electrically uncharged substance made up of molecules that further consist of atoms, wherein the atoms cannot be separated by physical means.
  • ligand is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion.
  • complex when used as a noun, is intended to mean a compound having at least one metallic ion and at least one ligand.
  • group is intended to mean a part of a compound, such as a substituent in an organic compound or a ligand in a complex.
  • adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
  • adjacent R groups is used to refer to R groups that are next to each other in a chemical formula (i.e., R groups that are on atoms joined by a bond).
  • photoactive refers to any material that exhibits electroluminescence and/or photosensitivity.
  • liquid or solution processing or solution deposition refers to the formation of uniform films from a liquid medium. In one embodiment, the film is robust.
  • the terms include any continuous or discontinuous method of depositing a material that is in the form of a liquid medium.
  • Liquid deposition techniques include, but are not limited to, continuous deposition techniques such as spin coating, gravure coating, curtain coating, dip coating, slot-die coating, casting, spray-coating, bar coating, roll coating, doctor blade coating and continuous nozzle coating; and discontinuous deposition techniques such as ink jet printing, gravure printing, and screen printing.
  • film refers to a coating covering a desired area. The area can be as large as an entire display, or as small as a single pixel. Films can be formed by any conventional deposition technique, including vapor deposition and liquid deposition.
  • solvent-solubilizing indicates that the solubility or dispersability of a material in at least one organic solvent has been increased.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

La présente invention concerne, de manière générale, le composé organométallique représenté par la formule suivante (I), ainsi que des dispositifs électroniques organiques présentant une couche comprenant ledit composé.
PCT/US2005/020449 2004-06-09 2005-06-08 Complexe d'iridium electroluminescent et dispositifs fabriques a l'aide dudit compose WO2005124890A1 (fr)

Applications Claiming Priority (2)

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US54559604P 2004-06-09 2004-06-09
US60/545,596 2004-06-09

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WO2005124890A1 true WO2005124890A1 (fr) 2005-12-29

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PCT/US2005/020412 WO2005124889A1 (fr) 2004-06-09 2005-06-08 Composés organométalliques et dispositifs faits de ces composés

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EP (1) EP1754267A1 (fr)
JP (2) JP4934035B2 (fr)
KR (2) KR101233855B1 (fr)
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WO2016171358A1 (fr) * 2015-04-24 2016-10-27 삼성에스디아이 주식회사 Composé pour élément optoélectronique organique, élément optoélectronique organique, et dispositif d'affichage
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US11631825B2 (en) 2011-09-30 2023-04-18 Udc Ireland Limited Organic electroluminescent element and novel iridium complex
US11827648B2 (en) 2018-04-02 2023-11-28 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound

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JP4934035B2 (ja) 2012-05-16
KR20120052425A (ko) 2012-05-23
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WO2005124889A1 (fr) 2005-12-29
KR101292376B1 (ko) 2013-08-01

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