Stable blue phosphorescent organic light emitting devices

Forrest, Stephen R.; Thompson, Mark; Giebink, Noel

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Title: Stable blue phosphorescent organic light emitting devices

Abstract

Novel combination of materials and device architectures for organic light emitting devices is provided. An organic light emitting device, is provided, having an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer includes a host and a phosphorescent emissive dopant having a peak emissive wavelength less than 500 nm, and a radiative phosphorescent lifetime less than 1 microsecond. Preferably, the phosphorescent emissive dopant includes a ligand having a carbazole group.

Inventors:: Forrest, Stephen R.; Thompson, Mark; Giebink, Noel

Issue Date:: 2014-08-26

Research Org.:: National Energy Technology Laboratory (NETL), Pittsburgh, PA, Morgantown, WV (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1151770

Patent Number(s):: 8815411

Application Number:: 12/257,638

Assignee:: The Regents of the University of Michigan (Ann Arbor, MI); University of Southern California (Los Angeles, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
C07F15/0033 - {Iridium compounds}

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K11/06 - containing organic luminescent materials
C09K2211/1059 - containing three nitrogen atoms as heteroatoms
C09K2211/185 - of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y10 - TECHNICAL SUBJECTS COVERED BY FORMER USPC Y10S - TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
Y10S428/917 - Electroluminescent

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DOE Contract Number:: FC26-04NT42272

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 42 ENGINEERING

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                    Forrest, Stephen R., Thompson, Mark, and Giebink, Noel. Stable blue phosphorescent organic light emitting devices.  United States: N. p., 2014. 
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                    Forrest, Stephen R., Thompson, Mark, & Giebink, Noel. Stable blue phosphorescent organic light emitting devices.  United States.

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                    Forrest, Stephen R., Thompson, Mark, and Giebink, Noel. Tue .  
        "Stable blue phosphorescent organic light emitting devices".  United States.  https://www.osti.gov/servlets/purl/1151770.

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@article{osti_1151770,

  title        = {Stable blue phosphorescent organic light emitting devices},

  author       = {Forrest, Stephen R. and Thompson, Mark and Giebink, Noel},

  abstractNote = {Novel combination of materials and device architectures for organic light emitting devices is provided. An organic light emitting device, is provided, having an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer includes a host and a phosphorescent emissive dopant having a peak emissive wavelength less than 500 nm, and a radiative phosphorescent lifetime less than 1 microsecond. Preferably, the phosphorescent emissive dopant includes a ligand having a carbazole group.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2014},

  month        = {8}

}

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Observation of the Mott–Gurney law in tris (8-hydroxyquinoline) aluminum films
journal, February 2002

Kiy, M.; Losio, P.; Biaggio, I.
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Organic light emitting device architecture for reducing the number of organic materials

Patent D'Andrade, Brian [Westampton, NJ]; Esler, James [Levittown, PA]

An organic light emitting device is provided. The device includes an anode and a cathode. A first emissive layer is disposed between the anode and the cathode. The first emissive layer includes a first non-emitting organic material, which is an organometallic material present in the first emissive layer in a concentration of at least 50 wt %. The first emissive layer also includes a first emitting organic material. A second emissive layer is disposed between the first emissive layer and the cathode, preferably, in direct contact with the first emissive layer. The second emissive material includes a second non-emitting organicmore » « less
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Highly reliable stacked white organic light emitting device

Patent Forrest, Stephen R.; Coburn, Caleb; Jeong, Changyeong

An organic light emitting device (OLED) is provided that includes a cathode and an anode; a blue emitting layer; and at least two hybrid red/green emitting layers. One of the at least two hybrid red/green emitting layers is a cathode side, red/green emitting layer that is disposed between the cathode and the blue emitting layer. The second of the at least two hybrid red/green emitting layers is an anode side, red/green emitting layer that is disposed between the blue emitting layer and the anode. The OLED emits white light.
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Citation Formats

Electroluminescent device with modified thin film luminescent zone patent, September 1988

Electroluminescent devices patent, September 1993

Transparent contacts for organic devices patent, December 1997

Multicolor organic light emitting devices patent, January 1998

High efficiency organic light emitting devices with light directing structures patent, November 1998

Vacuum deposited, non-polymeric flexible organic light emitting devices patent, December 1998

Organic electroluminescent device with graded region patent, July 1999

Saturated full color stacked organic light emitting devices patent, August 1999

Organic electroluminescent device with plural microcavities patent, September 1999

Multicolor display devices patent, January 2000

Fabrication of organic semiconductor devices using ink jet printing patent, July 2000

Displays having mesa pixel configuration patent, July 2000

Structure for high efficiency electroluminescent device patent, August 2000

White light generating organic electroluminescent device and method of fabrication patent, October 2000

Organic electroluminescent device with improved reliability patent, February 2001

Method for patterning devices patent, September 2001

OLEDs doped with phosphorescent compounds patent, October 2001

Method of purifying a primary color generated by an OED patent, December 2001

Low pressure vapor phase deposition of organic thin films patent, January 2002

Method for patterning organic thin film devices using a die patent, October 2002

Highly efficient OLEDs using doped ambipolar conductive molecular organic thin films patent, June 2003

Doping of organic opto-electronic devices to extend reliability patent, February 2007

Complexes with tridentate ligands patent, October 2007

Very Low Voltage, High Efficiency Phosphorescent OLED in a p-i-n Structure patent-application, December 2003

Transparent electrodes patent-application, September 2004

Phosphorescent dendrimers for use in light-emitting devices patent-application, June 2005

Flat panel light emitting devices with two sided patent-application, January 2006

Organic metal compounds in which compounds for host and compounds for dopant are connected, organic electroluminesence display devices using the compounds and method for preparation of the devices patent-application,

Stability OLED materials and devices patent-application, November 2006

High-molecular copolymer containing metal coordination compound and organic electroluminescence element using the same patent-application, December 2006

Stable and efficient electroluminescent materials patent-application, January 2007

Electron impeding layer for high efficiency phosphorescent OLEDs patent-application, April 2007

Metal coordination compound, polymer composition, and organic electroluminescent device employing same patent-application, June 2007

Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1',2'-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof patent-application, August 2007

Highly efficient phosphorescent emission from organic electroluminescent devices journal, September 1998

Very high-efficiency green organic light-emitting devices based on electrophosphorescence journal, July 1999

Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands journal, June 2004

Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors journal, November 2006

Management of singlet and triplet excitons for efficient white organic light-emitting devices journal, April 2006

Highly Branched Phosphorescent Dendrimers for Efficient Solution-Processed Organic Light-Emitting Diodes journal, May 2007

Tris-Cyclometalated Iridium(III) Complexes of Carbazole(fluorenyl)pyridine Ligands: Synthesis, Redox and Photophysical Properties, and Electrophosphorescent Light-Emitting Diodes journal, February 2007

Surface Plasmon Mediated Emission from Organic Light-Emitting Diodes journal, October 2002

Efficient organic light-emitting diode using semitransparent silver as anode journal, October 2005

Characterization of thin-metal anode buffers in organic devices journal, January 2006

Efficiency improvement of phosphorescent organic light-emitting diodes using semitransparent Ag as anode journal, January 2006

Au-ITO anode for efficient polymer light-emitting device operation journal, March 2005

Enhancement of hole injection using ozone treated Ag nanodots dispersed on indium tin oxide anode for organic light emitting diodes journal, April 2007

Free-radical pathways in operational degradation of OLEDs journal, January 2008

Blue Phosphorescence from Iridium(III) Complexes at Room Temperature journal, October 2006

47.2: Distinguished Paper : Structural Identification of Chemical Products and Mechanism of Operational Degradation of OLEDs journal, May 2007

Intrinsic luminance loss in phosphorescent small-molecule organic light emitting devices due to bimolecular annihilation reactions journal, February 2008

Triplet-exciton quenching in organic phosphorescent light-emitting diodes with Ir-based emitters journal, March 2007

Surface plasmon-polariton mediated emission from phosphorescent dendrimer light-emitting diodes journal, April 2006

Transient analysis of organic electrophosphorescence. II. Transient analysis of triplet-triplet annihilation journal, October 2000

Optical properties of molecular organic semiconductor thin films under intense electrical excitation journal, February 1999

Efficient, deep-blue organic electrophosphorescence by guest charge trapping journal, November 2003

In Situ Purification of Organic Materials for Organic Light-Emitting Device Fabrication journal, August 2001

Graded doping profiles for reduction of carrier trapping in organic light-emitting devices incorporating doped polymers journal, January 2001

Highly efficient simplified organic light emitting diodes journal, September 2007

Observation of the Mott–Gurney law in tris (8-hydroxyquinoline) aluminum films journal, February 2002

Reliability and degradation of small molecule-based organic light-emitting devices (OLEDs) journal, January 2002

The mechanism of lifetime extension due to CuPc injection layer in organic light-emitting diodes conference, September 2004

Photo and photo-oxidative degradations of poly(phenylene vinylene) derivatives journal, June 2002

Electroluminescent device with modified thin film luminescent zone
patent, September 1988

Electroluminescent devices
patent, September 1993

Transparent contacts for organic devices
patent, December 1997

Multicolor organic light emitting devices
patent, January 1998

High efficiency organic light emitting devices with light directing structures
patent, November 1998

Vacuum deposited, non-polymeric flexible organic light emitting devices
patent, December 1998

Organic electroluminescent device with graded region
patent, July 1999

Saturated full color stacked organic light emitting devices
patent, August 1999

Organic electroluminescent device with plural microcavities
patent, September 1999

Multicolor display devices
patent, January 2000

Fabrication of organic semiconductor devices using ink jet printing
patent, July 2000

Displays having mesa pixel configuration
patent, July 2000

Structure for high efficiency electroluminescent device
patent, August 2000

White light generating organic electroluminescent device and method of fabrication
patent, October 2000

Organic electroluminescent device with improved reliability
patent, February 2001

Method for patterning devices
patent, September 2001

OLEDs doped with phosphorescent compounds
patent, October 2001

Method of purifying a primary color generated by an OED
patent, December 2001

Low pressure vapor phase deposition of organic thin films
patent, January 2002

Method for patterning organic thin film devices using a die
patent, October 2002

Highly efficient OLEDs using doped ambipolar conductive molecular organic thin films
patent, June 2003

Doping of organic opto-electronic devices to extend reliability
patent, February 2007

Complexes with tridentate ligands
patent, October 2007

Very Low Voltage, High Efficiency Phosphorescent OLED in a p-i-n Structure
patent-application, December 2003

Transparent electrodes
patent-application, September 2004

Phosphorescent dendrimers for use in light-emitting devices
patent-application, June 2005

Flat panel light emitting devices with two sided
patent-application, January 2006

Organic metal compounds in which compounds for host and compounds for dopant are connected, organic electroluminesence display devices using the compounds and method for preparation of the devices
patent-application,

Stability OLED materials and devices
patent-application, November 2006

High-molecular copolymer containing metal coordination compound and organic electroluminescence element using the same
patent-application, December 2006

Stable and efficient electroluminescent materials
patent-application, January 2007

Electron impeding layer for high efficiency phosphorescent OLEDs
patent-application, April 2007

Metal coordination compound, polymer composition, and organic electroluminescent device employing same
patent-application, June 2007

Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1',2'-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
patent-application, August 2007

Highly efficient phosphorescent emission from organic electroluminescent devices
journal, September 1998

Very high-efficiency green organic light-emitting devices based on electrophosphorescence
journal, July 1999

Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands
journal, June 2004

Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors
journal, November 2006

Management of singlet and triplet excitons for efficient white organic light-emitting devices
journal, April 2006

Highly Branched Phosphorescent Dendrimers for Efficient Solution-Processed Organic Light-Emitting Diodes
journal, May 2007

Tris-Cyclometalated Iridium(III) Complexes of Carbazole(fluorenyl)pyridine Ligands: Synthesis, Redox and Photophysical Properties, and Electrophosphorescent Light-Emitting Diodes
journal, February 2007

Surface Plasmon Mediated Emission from Organic Light-Emitting Diodes
journal, October 2002

Efficient organic light-emitting diode using semitransparent silver as anode
journal, October 2005

Characterization of thin-metal anode buffers in organic devices
journal, January 2006

Efficiency improvement of phosphorescent organic light-emitting diodes using semitransparent Ag as anode
journal, January 2006

Au-ITO anode for efficient polymer light-emitting device operation
journal, March 2005

Enhancement of hole injection using ozone treated Ag nanodots dispersed on indium tin oxide anode for organic light emitting diodes
journal, April 2007

Free-radical pathways in operational degradation of OLEDs
journal, January 2008

Blue Phosphorescence from Iridium(III) Complexes at Room Temperature
journal, October 2006

47.2: Distinguished Paper : Structural Identification of Chemical Products and Mechanism of Operational Degradation of OLEDs
journal, May 2007

Intrinsic luminance loss in phosphorescent small-molecule organic light emitting devices due to bimolecular annihilation reactions
journal, February 2008

Triplet-exciton quenching in organic phosphorescent light-emitting diodes with Ir-based emitters
journal, March 2007

Surface plasmon-polariton mediated emission from phosphorescent dendrimer light-emitting diodes
journal, April 2006

Transient analysis of organic electrophosphorescence. II. Transient analysis of triplet-triplet annihilation
journal, October 2000

Optical properties of molecular organic semiconductor thin films under intense electrical excitation
journal, February 1999

Efficient, deep-blue organic electrophosphorescence by guest charge trapping
journal, November 2003

In Situ Purification of Organic Materials for Organic Light-Emitting Device Fabrication
journal, August 2001

Graded doping profiles for reduction of carrier trapping in organic light-emitting devices incorporating doped polymers
journal, January 2001

Highly efficient simplified organic light emitting diodes
journal, September 2007

Observation of the Mott–Gurney law in tris (8-hydroxyquinoline) aluminum films
journal, February 2002

Reliability and degradation of small molecule-based organic light-emitting devices (OLEDs)
journal, January 2002

The mechanism of lifetime extension due to CuPc injection layer in organic light-emitting diodes
conference, September 2004

Photo and photo-oxidative degradations of poly(phenylene vinylene) derivatives
journal, June 2002