Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers

Li, Huaping; Xu, Yunhua; Bazan, Guillermo C

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Title: Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers

Abstract

Tetrakis(1-imidazolyl)borate (BIm4) based zwitterionic and/or related molecules for the fabrication of PLEDs is provided. Device performances with these materials approaches that of devices with Ba/Al cathodes for which the cathode contact is ohmic. Methods of producing such materials, and electron injection layers and devices containing these materials are also provided.

Inventors:: Li, Huaping; Xu, Yunhua; Bazan, Guillermo C

Issue Date:: Tue Feb 05 00:00:00 EST 2013

Research Org.:: Univ. of California, Oakland, CA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1083217

Patent Number(s):: 8367839

Application Number:: 12/592,761

Assignee:: The Regents of the University of California (Oakland, 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

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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
C07F5/022 - {without C-boron linkages}

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Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 36 MATERIALS SCIENCE

Citation Formats


                    Li, Huaping, Xu, Yunhua, and Bazan, Guillermo C. Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers.  United States: N. p., 2013. 
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                    Li, Huaping, Xu, Yunhua, & Bazan, Guillermo C. Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers.  United States.

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                    Li, Huaping, Xu, Yunhua, and Bazan, Guillermo C. Tue .  
        "Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers".  United States.  https://www.osti.gov/servlets/purl/1083217.

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@article{osti_1083217,

  title        = {Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers},

  author       = {Li, Huaping and Xu, Yunhua and Bazan, Guillermo C},

  abstractNote = {Tetrakis(1-imidazolyl)borate (BIm4) based zwitterionic and/or related molecules for the fabrication of PLEDs is provided. Device performances with these materials approaches that of devices with Ba/Al cathodes for which the cathode contact is ohmic. Methods of producing such materials, and electron injection layers and devices containing these materials are also provided.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Feb 05 00:00:00 EST 2013},

  month        = {Tue Feb 05 00:00:00 EST 2013}

}

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Detection of biological molecules using boronate-based chemical amplification and optical sensors

Patent Van Antwerp, William Peter [Valencia, CA]; Mastrototaro, John Joseph [Los Angeles, CA]; Lane, Stephen M [Oakland, CA]; ...

Methods are provided for the determination of the concentration of biological levels of polyhydroxylated compounds, particularly glucose. The methods utilize an amplification system that is an analyte transducer immobilized in a polymeric matrix, where the system is implantable and biocompatible. Upon interrogation by an optical system, the amplification system produces a signal capable of detection external to the skin of the patient. Quantitation of the analyte of interest is achieved by measurement of the emitted signal.
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Title: Tetrakis(1-imidazolyl) borate (BIM4) based zwitterionic and related molecules used as electron injection layers

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Citation Formats

Boron-based organic cations and related methods patent-application, June 2006

Molecular Design, Device Function and Surface Potential of Zwitterionic Electron Injection Layers journal, July 2009

Organic electroluminescent diodes journal, September 1987

Light-emitting diodes based on conjugated polymers journal, October 1990

Electroluminescent Conjugated Polymers—Seeing Polymers in a New Light journal, March 1998

Integrated Optoelectronic Devices Based on Conjugated Polymers journal, June 1998

Organic Thin Film Transistors for Large Area Electronics journal, January 2002

Highly Efficient Organic Devices Based on Electrically Doped Transport Layers journal, April 2007

Two‐layer organic photovoltaic cell journal, January 1986

Plastic Solar Cells journal, February 2001

Efficient Tandem Polymer Solar Cells Fabricated by All-Solution Processing journal, July 2007

Exciplex Formation and Energy Transfer in Mixed Films of Phthalocyanine and Perylene Tetracarboxylic Diimide Derivatives journal, January 2003

Self-Organization of Nanocrystals in Polymer Brushes. Application in Heterojunction Photovoltaic Diodes journal, September 2005

A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene:fullerene solar cells journal, February 2006

Molecular Engineering of Coaxial Donor−Acceptor Heterojunction by Coassembly of Two Different Hexabenzocoronenes: Graphitic Nanotubes with Enhanced Photoconducting Properties journal, August 2007

Control of Ambipolar Thin Film Architectures by Co-Self-Assembling Oligo( p -phenylenevinylene)s and Perylene Bisimides journal, July 2006

Molecular engineering of organic semiconductors: design of self-assembly properties in conjugated thiophene oligomers journal, September 1993

Organization of Charge-Carrier Pathways for Organic Electronics journal, September 2006

Highly oriented crystals at the buried interface in polythiophene thin-film transistors journal, February 2006

Orientation-dependent ionization energies and interface dipoles in ordered molecular assemblies journal, February 2008

Charge Injection Across Self-Assembly Monolayers in Organic Field-Effect Transistors: Odd−Even Effects journal, May 2007

Single-Molecule Spectroscopy of Interfacial Electron Transfer journal, October 2003

Interface engineering in preparation of organic surface-emitting diodes journal, May 1999

Efficient light-emitting diodes based on polymers with high electron affinities journal, October 1993

Internal Field Screening in Polymer Light-Emitting Diodes journal, June 2004

Carrier tunneling and device characteristics in polymer light‐emitting diodes journal, February 1994

The roles of injection and mobility in organic light emitting diodes journal, May 1998

Molecular-scale interface engineering for polymer light-emitting diodes journal, March 2000

Highly Efficient Polymeric Electrophosphorescent Diodes journal, April 2006

Enhanced electron injection in organic electroluminescence devices using an Al/LiF electrode journal, January 1997

Fabrication and electroluminescence of double-layered organic light-emitting diodes with the Al2O3/Al cathode journal, March 1997

Achieving High-Efficiency Polymer White-Light-Emitting Devices journal, January 2006

Energy Level Alignment and Interfacial Electronic Structures at Organic/Metal and Organic/Organic Interfaces journal, June 1999

The Interface Energetics of Self-Assembled Monolayers on Metals journal, June 2008

How To Make Ohmic Contacts to Organic Semiconductors journal, January 2004

Direct measurement of the internal electric field distribution in a multilayer organic light‐emitting diode journal, November 1995

Novel Electroluminescent Conjugated Polyelectrolytes Based on Polyfluorene journal, February 2004

Recent Applications of Conjugated Polyelectrolytes in Optoelectronic Devices journal, October 2008

Control of Cationic Conjugated Polymer Performance in Light Emitting Diodes by Choice of Counterion journal, November 2006

Imaging the Interfaces of Conjugated Polymer Optoelectronic Devices journal, February 2008

Ion Motion in Conjugated Polyelectrolyte Electron Transporting Layers journal, September 2007

Electron injection into organic semiconductor devices from high work function cathodes journal, August 2008

Conjugated Oligoelectrolyte Electron Transport/Injection Layers for Organic Optoelectronic Devices journal, March 2008

Solvent Effects on the Architecture and Performance of Polymer White-Light-Emitting Diodes with Conjugated Oligoelectrolyte Electron-Transport Layers journal, November 2008

Tetrakis(imidazolyl)borate-Based Coordination Polymers: Group II Network Solids, M[B(Im) 4 ] 2 (H 2 O) 2 (M = Mg, Ca, Sr) journal, May 2003

Scientific importance, properties and growing applications of poly(3,4-ethylenedioxythiophene) journal, January 2005

Bright high efficiency blue organic light-emitting diodes with Al2O3/Al cathodes journal, November 1997

Design of Hole Blocking Layer with Electron Transport Channels for High Performance Polymer Light-Emitting Diodes journal, May 2008

Electroluminescence of doped organic thin films journal, May 1989

Efficient, Low Operating Voltage Polymer Light-Emitting Diodes with Aluminum as the Cathode Material journal, August 1998

High-Efficiency, Environment-Friendly Electroluminescent Polymers with Stable High Work Function Metal as a Cathode: Green- and Yellow-Emitting Conjugated Polyfluorene Polyelectrolytes and Their Neutral Precursors journal, August 2004

Efficient Electron Injection from a Bilayer Cathode Consisting of Aluminum and Alcohol-/Water-Soluble Conjugated Polymers journal, October 2004

Polymer Light-Emitting Electrochemical Cells journal, August 1995

Polymer Light-Emitting Electrochemical Cells: In Situ Formation of a Light-Emitting p−n Junction journal, January 1996

Direct measurement of the electric-field distribution in a light-emitting electrochemical cell journal, September 2007

Scanning Kelvin Probe Imaging of the Potential Profiles in Fixed and Dynamic Planar LECs journal, December 2007

Time-resolved electrostatic force microscopy of polymer solar cells journal, August 2006

Kelvin Probe Force Microscopy Study on Conjugated Polymer/Fullerene Bulk Heterojunction Organic Solar Cells journal, February 2005

Correlation between Surface Photovoltage and Blend Morphology in Polyfluorene-Based Photodiodes journal, April 2005

Photovoltaic Charge Generation Visualized at the Nanoscale: A Proof of Principle journal, January 2008

Electrostatic force microscopy: principles and some applications to semiconductors journal, November 2001

Direct measurement of electric field screening in light emitting diodes with conjugated polyelectrolyte electron injecting/transport layers journal, January 2009

Boron-based organic cations and related methods
patent-application, June 2006

Molecular Design, Device Function and Surface Potential of Zwitterionic Electron Injection Layers
journal, July 2009

Organic electroluminescent diodes
journal, September 1987

Light-emitting diodes based on conjugated polymers
journal, October 1990

Electroluminescent Conjugated Polymers—Seeing Polymers in a New Light
journal, March 1998

Integrated Optoelectronic Devices Based on Conjugated Polymers
journal, June 1998

Organic Thin Film Transistors for Large Area Electronics
journal, January 2002

Highly Efficient Organic Devices Based on Electrically Doped Transport Layers
journal, April 2007

Two‐layer organic photovoltaic cell
journal, January 1986

Plastic Solar Cells
journal, February 2001

Efficient Tandem Polymer Solar Cells Fabricated by All-Solution Processing
journal, July 2007

Exciplex Formation and Energy Transfer in Mixed Films of Phthalocyanine and Perylene Tetracarboxylic Diimide Derivatives
journal, January 2003

Self-Organization of Nanocrystals in Polymer Brushes. Application in Heterojunction Photovoltaic Diodes
journal, September 2005

A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene:fullerene solar cells
journal, February 2006

Molecular Engineering of Coaxial Donor−Acceptor Heterojunction by Coassembly of Two Different Hexabenzocoronenes: Graphitic Nanotubes with Enhanced Photoconducting Properties
journal, August 2007

Control of Ambipolar Thin Film Architectures by Co-Self-Assembling Oligo( p -phenylenevinylene)s and Perylene Bisimides
journal, July 2006

Molecular engineering of organic semiconductors: design of self-assembly properties in conjugated thiophene oligomers
journal, September 1993

Organization of Charge-Carrier Pathways for Organic Electronics
journal, September 2006

Highly oriented crystals at the buried interface in polythiophene thin-film transistors
journal, February 2006

Orientation-dependent ionization energies and interface dipoles in ordered molecular assemblies
journal, February 2008

Charge Injection Across Self-Assembly Monolayers in Organic Field-Effect Transistors: Odd−Even Effects
journal, May 2007

Single-Molecule Spectroscopy of Interfacial Electron Transfer
journal, October 2003

Interface engineering in preparation of organic surface-emitting diodes
journal, May 1999

Efficient light-emitting diodes based on polymers with high electron affinities
journal, October 1993

Internal Field Screening in Polymer Light-Emitting Diodes
journal, June 2004

Carrier tunneling and device characteristics in polymer light‐emitting diodes
journal, February 1994

The roles of injection and mobility in organic light emitting diodes
journal, May 1998

Molecular-scale interface engineering for polymer light-emitting diodes
journal, March 2000

Highly Efficient Polymeric Electrophosphorescent Diodes
journal, April 2006

Enhanced electron injection in organic electroluminescence devices using an Al/LiF electrode
journal, January 1997

Fabrication and electroluminescence of double-layered organic light-emitting diodes with the Al2O3/Al cathode
journal, March 1997

Achieving High-Efficiency Polymer White-Light-Emitting Devices
journal, January 2006

Energy Level Alignment and Interfacial Electronic Structures at Organic/Metal and Organic/Organic Interfaces
journal, June 1999

The Interface Energetics of Self-Assembled Monolayers on Metals
journal, June 2008

How To Make Ohmic Contacts to Organic Semiconductors
journal, January 2004

Direct measurement of the internal electric field distribution in a multilayer organic light‐emitting diode
journal, November 1995

Novel Electroluminescent Conjugated Polyelectrolytes Based on Polyfluorene
journal, February 2004

Recent Applications of Conjugated Polyelectrolytes in Optoelectronic Devices
journal, October 2008

Control of Cationic Conjugated Polymer Performance in Light Emitting Diodes by Choice of Counterion
journal, November 2006

Imaging the Interfaces of Conjugated Polymer Optoelectronic Devices
journal, February 2008

Ion Motion in Conjugated Polyelectrolyte Electron Transporting Layers
journal, September 2007

Electron injection into organic semiconductor devices from high work function cathodes
journal, August 2008

Conjugated Oligoelectrolyte Electron Transport/Injection Layers for Organic Optoelectronic Devices
journal, March 2008

Solvent Effects on the Architecture and Performance of Polymer White-Light-Emitting Diodes with Conjugated Oligoelectrolyte Electron-Transport Layers
journal, November 2008

Tetrakis(imidazolyl)borate-Based Coordination Polymers: Group II Network Solids, M[B(Im) ₄ ] ₂ (H ₂ O) ₂ (M = Mg, Ca, Sr)
journal, May 2003

Scientific importance, properties and growing applications of poly(3,4-ethylenedioxythiophene)
journal, January 2005

Bright high efficiency blue organic light-emitting diodes with Al2O3/Al cathodes
journal, November 1997

Design of Hole Blocking Layer with Electron Transport Channels for High Performance Polymer Light-Emitting Diodes
journal, May 2008

Electroluminescence of doped organic thin films
journal, May 1989

Efficient, Low Operating Voltage Polymer Light-Emitting Diodes with Aluminum as the Cathode Material
journal, August 1998

High-Efficiency, Environment-Friendly Electroluminescent Polymers with Stable High Work Function Metal as a Cathode: Green- and Yellow-Emitting Conjugated Polyfluorene Polyelectrolytes and Their Neutral Precursors
journal, August 2004

Efficient Electron Injection from a Bilayer Cathode Consisting of Aluminum and Alcohol-/Water-Soluble Conjugated Polymers
journal, October 2004

Polymer Light-Emitting Electrochemical Cells
journal, August 1995

Polymer Light-Emitting Electrochemical Cells: In Situ Formation of a Light-Emitting p−n Junction
journal, January 1996

Direct measurement of the electric-field distribution in a light-emitting electrochemical cell
journal, September 2007

Scanning Kelvin Probe Imaging of the Potential Profiles in Fixed and Dynamic Planar LECs
journal, December 2007

Time-resolved electrostatic force microscopy of polymer solar cells
journal, August 2006

Kelvin Probe Force Microscopy Study on Conjugated Polymer/Fullerene Bulk Heterojunction Organic Solar Cells
journal, February 2005

Correlation between Surface Photovoltage and Blend Morphology in Polyfluorene-Based Photodiodes
journal, April 2005

Photovoltaic Charge Generation Visualized at the Nanoscale: A Proof of Principle
journal, January 2008

Electrostatic force microscopy: principles and some applications to semiconductors
journal, November 2001

Direct measurement of electric field screening in light emitting diodes with conjugated polyelectrolyte electron injecting/transport layers
journal, January 2009