Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Phenanthro[9,10-d]triazole and imidazole derivatives: high triplet energy host materials for blue phosphorescent organic light emitting devices

Journal Article · · Materials Horizons
DOI:https://doi.org/10.1039/c9mh00195f· OSTI ID:1735848

A class of wide bandgap host materials is introduced as an alternative to carbazole-based hosts to enhance the efficiency and transport properties of organic light emitting diodes (OLEDs). We have synthesized and investigate the photophysical and electrochemical properties of a series of phenanthrene derivatives incorporating fused triazole or imidazole rings. Here, the resulting phenanthro[9,10-d]triazoles and phenanthro[9,10-d]imidazoles are suitable host materials for blue phosphors due to their high triplet energies and conductivities. Incorporation of bulky substituent groups leads to retention of the high triplet energies in the solid state. The most promising materials are incorporated in blue phosphorescent OLEDs that achieve external quantum efficiencies >20%.

Research Organization:
Univ. of Southern California, Los Angeles, CA (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Building Technologies Office
Grant/Contract Number:
EE0007077; EE0007626
OSTI ID:
1735848
Alternate ID(s):
OSTI ID: 1614017
OSTI ID: 1498805
Journal Information:
Materials Horizons, Journal Name: Materials Horizons Journal Issue: 6 Vol. 6; ISSN 2051-6347
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (41)

Above 30% External Quantum Efficiency in Blue Phosphorescent Organic Light-Emitting Diodes Using Pyrido[2,3- b ]indole Derivatives as Host Materials journal June 2013
Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles journal August 2011
Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles journal January 2007
Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles journal August 2011
Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles. journal May 2007
Substitution reactions of phenanthro[9,10- d ]triazole with benzyl chlorides journal March 1998
Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations journal September 2014
Quantitative phosphorescence spectroscopy of polystyrene during photo-degradation and the significance of in-chain peroxides journal January 1977
Tuning the nonlinear optical properties of BODIPYs by functionalization with dimethylaminostyryl substituents journal February 2017
On the reliability of determination of energies of HOMO and LUMO levels in organic semiconductors from electrochemical measurements. A simple picture based on the electrostatic model journal June 2016
Below-one-volt organic thin-film transistors with large on/off current ratios journal October 2017
Development and Application of O -(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes journal June 2015
CN-Modified Host Materials for Improved Efficiency and Lifetime in Blue Phosphorescent and Thermally Activated Delayed Fluorescent Organic Light-Emitting Diodes journal April 2017
Rapid Multiscale Computational Screening for OLED Host Materials journal January 2019
Reliable, All-Phosphorescent Stacked White Organic Light Emitting Devices with a High Color Rendering Index journal November 2017
High-Efficiency BODIPY-Based Organic Photovoltaics journal December 2014
Ultrahigh Energy Gap Hosts in Deep Blue Organic Electrophosphorescent Devices journal November 2004
RGB Phosphorescent Organic Light-Emitting Diodes by Using Host Materials with Heterocyclic Cores: Effect of Nitrogen Atom Orientations journal January 2011
Donor-Substituted 1,3,5-Triazines as Host Materials for Blue Phosphorescent Organic Light-Emitting Diodes journal April 2010
Influence of Halogen Atoms on a Homologous Series of Bis-Cyclometalated Iridium(III) Complexes journal December 2011
A Step-Economical Route to Fused 1,2,3-Triazoles via an Intramolecular 1,3-Dipolar Cycloaddition between a Nitrile and an in Situ Generated Aryldiazomethane journal August 2014
Simple Phenanthroimidazole/Carbazole Hybrid Bipolar Host Materials for Highly Efficient Green and Yellow Phosphorescent Organic Light-Emitting Diodes journal September 2012
Rational Design of Dibenzothiophene-Based Host Materials for PHOLEDs journal January 2014
Blue Light Emitting Ir(III) Compounds for OLEDs - New Insights into Ancillary Ligand Effects on the Emitting Triplet State journal May 2009
Highly efficient phosphorescent emission from organic electroluminescent devices journal September 1998
Deep blue organic light-emitting devices enabled by bipolar phenanthro[9,10-d]imidazole derivatives journal January 2015
High efficiency single dopant white electrophosphorescent light emitting diodesElectronic supplementary information (ESI) available: emission spectra as a function of doping concentration for 3 in CBP, as well as the absorption and emission spectra of Irppz, CBP and mCP. See http://www.rsc.org/suppdata/nj/b2/b204301g/ journal August 2002
Synthesis and photo- and electroluminescence properties of 3,6-disubstituted phenanthrenes: alternative host material for blue fluorophores journal January 2011
Improved energy transfer in electrophosphorescent devices journal January 1999
Very high-efficiency green organic light-emitting devices based on electrophosphorescence journal July 1999
Operating lifetime of phosphorescent organic light emitting devices journal May 2000
Endothermic energy transfer: A mechanism for generating very efficient high-energy phosphorescent emission in organic materials journal September 2001
Nearly 100% internal phosphorescence efficiency in an organic light-emitting device journal November 2001
Blue organic electrophosphorescence using exothermic host–guest energy transfer journal April 2003
Confinement of triplet energy on phosphorescent molecules for highly-efficient organic blue-light-emitting devices journal July 2003
Current-gain cutoff frequencies above 10 MHz for organic thin-film transistors with high mobility and low parasitic capacitance journal July 2009
Two‐layer organic photovoltaic cell journal January 1986
Organic electroluminescent diodes journal September 1987
Triphenylene-based Host Materials for Low-voltage, Highly Efficient Red Phosphorescent Organic Light-emitting Diodes journal April 2013
Organic Light-Emitting Devices for Solid-State Lighting journal July 2008
One-pot Microwave-Assisted Synthesis of 1H-Phenanthro[9,10- d][1,2,3]triazole journal September 2008

Cited By (4)