Host compounds for red phosphorescent OLEDs

Xia, Chuanjun; Cheon, Kwang -Ohk

Title: Host compounds for red phosphorescent OLEDs

Abstract

Novel compounds containing a triphenylene moiety linked to an .alpha..beta. connected binaphthyl ring system are provided. These compounds have surprisingly good solubility in organic solvents and are useful as host compounds in red phosphorescent OLEDs.

Inventors:: Xia, Chuanjun; Cheon, Kwang -Ohk

Issue Date:: Tue Aug 25 00:00:00 EDT 2015

Research Org.:: Universal Display Corporation, Ewing, NJ (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1212395

Patent Number(s):: 9118017

Application Number:: 13/718,248

Assignee:: Universal Display Corporation (Ewing, NJ)

DOE Contract Number:: EE0004534

Resource Type:: Patent

Resource Relation:: Patent File Date: 2012 Dec 18

Country of Publication:: United States

Language:: English

Subject:: 36 MATERIALS SCIENCE

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                    Xia, Chuanjun, and Cheon, Kwang -Ohk. Host compounds for red phosphorescent OLEDs.  United States: N. p., 2015. 
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                    Xia, Chuanjun, & Cheon, Kwang -Ohk. Host compounds for red phosphorescent OLEDs.  United States.

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                    Xia, Chuanjun, and Cheon, Kwang -Ohk. Tue .  
        "Host compounds for red phosphorescent OLEDs".  United States.  https://www.osti.gov/servlets/purl/1212395.

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@article{osti_1212395,

  title        = {Host compounds for red phosphorescent OLEDs},

  author       = {Xia, Chuanjun and Cheon, Kwang -Ohk},

  abstractNote = {Novel compounds containing a triphenylene moiety linked to an .alpha..beta. connected binaphthyl ring system are provided. These compounds have surprisingly good solubility in organic solvents and are useful as host compounds in red phosphorescent OLEDs.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Aug 25 00:00:00 EDT 2015},

  month        = {Tue Aug 25 00:00:00 EDT 2015}

}

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https://doi.org/10.1063/1.1384903

A novel class of phosphorescent gold(iii) alkynyl-based organic light-emitting devices with tunable colour
journal, January 2005

Wong, Keith Man-Chung; Zhu, Xiuling; Hung, Ling-Ling
Chemical Communications, Issue 23
https://doi.org/10.1039/B503315B

Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors
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Wong, Wai-Yeung; Ho, Cheuk-Lam; Gao, Zhi-Qiang
Angewandte Chemie International Edition, Vol. 45, Issue 46, p. 7800-7803
https://doi.org/10.1002/anie.200602906

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Title: Host compounds for red phosphorescent OLEDs

Abstract

Citation Formats

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

Electroluminescent device with organic electroluminescent medium patent, October 1991

Electroluminescent devices patent, September 1993

Transparent contacts for organic devices patent, December 1997

Multicolor organic light emitting devices patent, January 1998

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

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

Method for patterning devices patent, September 2001

OLEDs doped with phosphorescent compounds patent, October 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

Material for luminescence element and luminescence element using the same patent, March 2003

Organic light emitting materials and devices patent, February 2004

Phosphorescent compounds and devices comprising the same patent, December 2004

Metal coordination compound, luminescence device and display apparatus patent, July 2005

Organic light emitting devices having reduced pixel shrinkage patent, August 2006

Binuclear compounds patent, August 2006

Cyclometallated iridium carbene complexes for use as hosts patent, December 2006

Phosphorescent compound, a phosphorescent composition and an organic light-emitting device patent, July 2007

Complexes with tridentate ligands patent, October 2007

OLEDs utilizing multidentate ligand systems patent, February 2008

Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir patent, March 2008

Luminescent compounds with carbene ligands patent, July 2008

Light emitting material and organic light-emitting device patent, July 2008

Process and apparatus for organic vapor jet deposition patent, October 2008

Cationic metal-carbene complexes patent, November 2008

Organometallic compounds for use in electroluminescent devices patent, May 2009

Organometallic complexes as phosphorescent emitters in organic LEDs patent-application, March 2002

Transition Metal Complex and Light-Emitting Device patent-application, September 2002

Electronic Device Comprising Organic Compound Having P-Type Semiconducting Characteristics patent-application, October 2002

Deuterated Semi-Conducting Organic Compounds Used for Opto-Electronic Devices patent-application, July 2003

White light emitting oleds from combined monomer and aggregate emission patent-application, September 2003

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

Light Emitting Element patent-application, February 2004

Organic Electroluminescent Device patent-application, July 2004

Transparent electrodes patent-application, September 2004

Materials and Structures for Enhancing the Performance of Organic Light Emitting Devices patent-application, February 2005

Organic Electroluminescent Device patent-application, May 2005

Organic Light Emitting Materials and Devices patent-application, January 2006

Stability OLED materials and devices patent-application, November 2006

Organic electroluminescent device patent-application, November 2006

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

Organic electroluminescent device having a hole conductor as an emitting layer journal, October 1989

Nearly 100% internal phosphorescence efficiency in an organic light-emitting device journal, November 2001

High-efficiency red electrophosphorescence devices journal, March 2001

Material design of hole transport materials capable of thick-film formation in organic light emitting diodes journal, April 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

Bright-blue electroluminescence from a silyl-substituted ter-(phenylene–vinylene) derivative journal, February 1999

Highly efficient electrophosphorescent polymer light-emitting devices journal, December 2000

High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato)beryllium as an Emitter journal, May 1993

Blue organic electrophosphorescence using exothermic host–guest energy transfer journal, April 2003

Novel high Tg hole-transport molecules based on indolo[3,2-b]carbazoles for organic light-emitting devices journal, June 2000

Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2,N)iridium(III) Derivatives journal, March 2007

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

Anode modification in organic light-emitting diodes by low-frequency plasma polymerization of CHF3 journal, January 2001

Highly efficient phosphorescence from organic light-emitting devices with an exciton-block layer journal, July 2001

P-185: Low-Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide journal, January 2006

1,3,5-Tris[4-(diphenylamino)phenyl]benzene and its methyl-substituted derivatives as a novel class of amorphous molecular materials journal, January 1993

Highly efficient and stable red phosphorescent organic light-emitting device using bis[2-(2-benzothiazoyl)phenolato]zinc(II) as host material journal, March 2007

1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices journal, July 1993

Thermally stable multilared organic electroluminescent devices using novel starburst molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), as hole-transport materials journal, September 1994

High operational stability of electrophosphorescent devices journal, July 2002

Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes journal, March 2001

Polymer phosphorescent light-emitting devices doped with tris(2-phenylpyridine) iridium as a triplet emitter journal, October 2000

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

Triplet luminescent dinuclear-gold( I ) complex-based light-emitting diodes with low turn-on voltage journal, March 1999

Thermally Stable Hole-Transporting Material for Organic Light-Emitting Diode: an Isoindole Derivative journal, August 2003

Preparation, Characterization, and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands journal, April 2005

Highly Efficient Electrophosphorescent Devices with Saturated Red Emission from a Neutral Osmium Complex journal, June 2005

5,5‘-Bis(dimesitylboryl)-2,2‘-bithiophene and 5,5‘‘-Bis(dimesitylboryl)-2,2‘:5‘,2‘‘-terthiophene as a Novel Family of Electron-Transporting Amorphous Molecular Materials journal, September 1998

Green fluorescent organic light-emitting device with external quantum efficiency of nearly 10% journal, August 2006

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

Electroluminescent device with organic electroluminescent medium
patent, October 1991

Electroluminescent devices
patent, September 1993

Transparent contacts for organic devices
patent, December 1997

Multicolor organic light emitting devices
patent, January 1998

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

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

Method for patterning devices
patent, September 2001

OLEDs doped with phosphorescent compounds
patent, October 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

Material for luminescence element and luminescence element using the same
patent, March 2003

Organic light emitting materials and devices
patent, February 2004

Phosphorescent compounds and devices comprising the same
patent, December 2004

Metal coordination compound, luminescence device and display apparatus
patent, July 2005

Organic light emitting devices having reduced pixel shrinkage
patent, August 2006

Binuclear compounds
patent, August 2006

Cyclometallated iridium carbene complexes for use as hosts
patent, December 2006

Phosphorescent compound, a phosphorescent composition and an organic light-emitting device
patent, July 2007

Complexes with tridentate ligands
patent, October 2007

OLEDs utilizing multidentate ligand systems
patent, February 2008

Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir
patent, March 2008

Luminescent compounds with carbene ligands
patent, July 2008

Light emitting material and organic light-emitting device
patent, July 2008

Process and apparatus for organic vapor jet deposition
patent, October 2008

Cationic metal-carbene complexes
patent, November 2008

Organometallic compounds for use in electroluminescent devices
patent, May 2009

Organometallic complexes as phosphorescent emitters in organic LEDs
patent-application, March 2002

Transition Metal Complex and Light-Emitting Device
patent-application, September 2002

Electronic Device Comprising Organic Compound Having P-Type Semiconducting Characteristics
patent-application, October 2002

Deuterated Semi-Conducting Organic Compounds Used for Opto-Electronic Devices
patent-application, July 2003

White light emitting oleds from combined monomer and aggregate emission
patent-application, September 2003

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

Light Emitting Element
patent-application, February 2004

Organic Electroluminescent Device
patent-application, July 2004

Transparent electrodes
patent-application, September 2004

Materials and Structures for Enhancing the Performance of Organic Light Emitting Devices
patent-application, February 2005

Organic Electroluminescent Device
patent-application, May 2005

Organic Light Emitting Materials and Devices
patent-application, January 2006

Stability OLED materials and devices
patent-application, November 2006

Organic electroluminescent device
patent-application, November 2006

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

Organic electroluminescent device having a hole conductor as an emitting layer
journal, October 1989

Nearly 100% internal phosphorescence efficiency in an organic light-emitting device
journal, November 2001

High-efficiency red electrophosphorescence devices
journal, March 2001

Material design of hole transport materials capable of thick-film formation in organic light emitting diodes
journal, April 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

Bright-blue electroluminescence from a silyl-substituted ter-(phenylene–vinylene) derivative
journal, February 1999

Highly efficient electrophosphorescent polymer light-emitting devices
journal, December 2000

High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato)beryllium as an Emitter
journal, May 1993

Blue organic electrophosphorescence using exothermic host–guest energy transfer
journal, April 2003

Novel high Tg hole-transport molecules based on indolo[3,2-b]carbazoles for organic light-emitting devices
journal, June 2000

Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2,N)iridium(III) Derivatives
journal, March 2007

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

Anode modification in organic light-emitting diodes by low-frequency plasma polymerization of CHF3
journal, January 2001

Highly efficient phosphorescence from organic light-emitting devices with an exciton-block layer
journal, July 2001

P-185: Low-Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide
journal, January 2006

1,3,5-Tris[4-(diphenylamino)phenyl]benzene and its methyl-substituted derivatives as a novel class of amorphous molecular materials
journal, January 1993

Highly efficient and stable red phosphorescent organic light-emitting device using bis[2-(2-benzothiazoyl)phenolato]zinc(II) as host material
journal, March 2007

1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices
journal, July 1993

Thermally stable multilared organic electroluminescent devices using novel starburst molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), as hole-transport materials
journal, September 1994

High operational stability of electrophosphorescent devices
journal, July 2002

Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes
journal, March 2001

Polymer phosphorescent light-emitting devices doped with tris(2-phenylpyridine) iridium as a triplet emitter
journal, October 2000

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

Triplet luminescent dinuclear-gold( I ) complex-based light-emitting diodes with low turn-on voltage
journal, March 1999

Thermally Stable Hole-Transporting Material for Organic Light-Emitting Diode: an Isoindole Derivative
journal, August 2003

Preparation, Characterization, and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands
journal, April 2005

Highly Efficient Electrophosphorescent Devices with Saturated Red Emission from a Neutral Osmium Complex
journal, June 2005

5,5‘-Bis(dimesitylboryl)-2,2‘-bithiophene and 5,5‘‘-Bis(dimesitylboryl)-2,2‘:5‘,2‘‘-terthiophene as a Novel Family of Electron-Transporting Amorphous Molecular Materials
journal, September 1998

Green fluorescent organic light-emitting device with external quantum efficiency of nearly 10%
journal, August 2006

High efficiency molecular organic light-emitting diodes based on silole derivatives and their exciplexes
journal, September 2003

First Examples of Alkenyl Pyridines as Organic Ligands for Phosphorescent Iridium Complexes
journal, November 2004

Realizing Green Phosphorescent Light-Emitting Materials from Rhenium(I) Pyrazolato Diimine Complexes
journal, February 2003