skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Effect of the Number and Substitution Pattern of Carbazole Donors on the Singlet and Triplet State Energies in a Series of Carbazole-Oxadiazole Derivatives Exhibiting Thermally Activated Delayed Fluorescence

Journal Article · · Chemistry of Materials

Substitution of a varying number of 9H-carbazole donors onto 2-(pentafluorophenyl)-5-phenyl-1,3,4-oxadiazole yields a series of donor–acceptor compounds with similar electrochemical band gaps, but dissimilar optical properties. Each substitution of a carbazole onto the 2- and 4-positions results in a 150–200 meV stabilization of the first singlet excited state, evident in the fluorescent emission. Here, the first triplet excited state is less sensitive to these substitutions, leading to a reduced energy separation between the singlet and triplet states, ΔEST, with increasing carbazole content. OLED devices made using the donor–acceptor compounds exhibiting the lowest ΔEST were fabricated and exhibit sky blue emission with an external quantum efficiency of up to 24.4% at a luminance of 10 cd m–2, and 9.2% at 1000 cd m–2.

Research Organization:
Georgia Institute of Technology, Atlanta, GA (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
Grant/Contract Number:
EE0008205
OSTI ID:
1767449
Journal Information:
Chemistry of Materials, Vol. 30, Issue 18; ISSN 0897-4756
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 14 works
Citation information provided by
Web of Science

References (49)

Organic electroluminescent diodes journal September 1987
Highly efficient phosphorescent emission from organic electroluminescent devices journal September 1998
Delayed Fluorescence Optical Thermometry journal December 1995
A study of thermally activated delayed fluorescence in C60 journal June 1997
Recent advances in organic thermally activated delayed fluorescence materials journal January 2017
Highly efficient blue electroluminescence based on thermally activated delayed fluorescence journal December 2014
Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes journal August 2012
Highly efficient organic light-emitting diodes from delayed fluorescence journal December 2012
Confinement of charge carriers and molecular excitons within 5‐nm‐thick emitter layer in organic electroluminescent devices with a double heterostructure journal August 1990
Blue light‐emitting organic electroluminescent devices journal February 1990
Electron Transport Materials for Organic Light-Emitting Diodes journal November 2004
Electron-transporting materials for organic electroluminescent and electrophosphorescent devices journal January 2005
Blue-Light-Emitting Organic Electroluminescent Devices with Oxadiazole Dimer Dyes as an Emitter journal June 1992
Charge Carrier Transporting Molecular Materials and Their Applications in Devices journal April 2007
The Unusual Electrochemical and Photophysical Behavior of 2,2‘-Bis(1,3,4-oxadiazol-2-yl)biphenyls, Effective Electron Transport Hosts for Phosphorescent Organic Light Emitting Diodes journal December 2006
A Simple Carbazole/Oxadiazole Hybrid Molecule: An Excellent Bipolar Host for Green and Red Phosphorescent OLEDs journal October 2008
Bipolar Host Materials: A Chemical Approach for Highly Efficient Electrophosphorescent Devices journal August 2011
Polymers with Carbazole-Oxadiazole Side Chains as Ambipolar Hosts for Phosphorescent Light-Emitting Diodes journal September 2011
The host materials containing carbazole and oxadiazole fragment for red triplet emitter in organic light-emitting diodes journal October 2006
Carbazole Compounds as Host Materials for Triplet Emitters in Organic Light-Emitting Diodes:  Tuning the HOMO Level without Influencing the Triplet Energy in Small Molecules journal May 2004
High-performance blue electroluminescent devices based on 2-(4-biphenylyl)-5-(4-carbazole-9-yl)phenyl-1,3,4-oxadiazole journal January 2003
New Carbazole−Oxadiazole Dyads for Electroluminescent Devices:  Influence of Acceptor Substituents on Luminescent and Thermal Properties journal December 2004
Colour tuning of blue electroluminescence using bipolar carbazole–oxadiazole molecules in single-active-layer organic light emitting devices (OLEDs) journal January 2012
Tuning the Optoelectronic Properties of Carbazole/Oxadiazole Hybrids through Linkage Modes: Hosts for Highly Efficient Green Electrophosphorescence journal January 2010
A carbazole–oxadiazole diad molecule for single-emitting-component white organic light-emitting devices (WOLEDs) journal March 2014
Oxadiazole- and triazole-based highly-efficient thermally activated delayed fluorescence emitters for organic light-emitting diodes journal January 2013
Creating a thermally activated delayed fluorescence channel in a single polymer system to enhance exciton utilization efficiency for bluish-green electroluminescence journal January 2016
Efficient blue organic light-emitting diodes employing thermally activated delayed fluorescence journal March 2014
Perspective on carbazole-based organic compounds as emitters and hosts in TADF applications journal January 2017
Purely organic materials for extremely simple all-TADF white OLEDs: a new carbazole/oxadiazole hybrid material as a dual-role non-doped light blue emitter and highly efficient orange host journal January 2018
The inductive-effect of electron withdrawing trifluoromethyl for thermally activated delayed fluorescence: tunable emission from tetra- to penta-carbazole in solution processed blue OLEDs journal January 2015
Local-Excitation versus Charge-Transfer Characters in the Triplet State: Theoretical Insight into the Singlet–Triplet Energy Differences of Carbazolyl-Phthalonitrile-Based Thermally Activated Delayed Fluorescence Materials journal December 2016
Design of Efficient Ambipolar Host Materials for Organic Blue Electrophosphorescence: Theoretical Characterization of Hosts Based on Carbazole Derivatives journal November 2011
Theoretical Investigation of Triscarbazole Derivatives As Host Materials for Blue Electrophosphorescence: Effects of Topology journal December 2011
Electronic Structure of Carbazole-Based Phosphine Oxides as Ambipolar Host Materials for Deep Blue Electrophosphorescence: A Density Functional Theory Study journal June 2012
Up-Conversion Intersystem Crossing Rates in Organic Emitters for Thermally Activated Delayed Fluorescence: Impact of the Nature of Singlet vs Triplet Excited States journal March 2017
Rational Design of TADF Polymers Using a Donor-Acceptor Monomer with Enhanced TADF Efficiency Induced by the Energy Alignment of Charge Transfer and Local Triplet Excited States journal January 2016
Triplet Harvesting with 100% Efficiency by Way of Thermally Activated Delayed Fluorescence in Charge Transfer OLED Emitters journal May 2013
Revealing the spin–vibronic coupling mechanism of thermally activated delayed fluorescence journal November 2016
Effect of Topology on the Singlet-Triplet Energy Difference and their Natures: A Density Functional Theory Study of Carbazolyl-Phthalonitrile Derivatives: Effect of Topology on the Singlet-Triplet Energy Difference journal July 2017
Molecular Design for Blue Thermal Activated Delayed Fluorescence Materials: Substitution Position Effect journal October 2017
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields journal November 1994
Hybrid Meta Density Functional Theory Methods for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions:  The MPW1B95 and MPWB1K Models and Comparative Assessments for Hydrogen Bonding and van der Waals Interactions journal August 2004
Mild Copper-Mediated Direct Oxidative Cross-Coupling of 1,3,4-Oxadiazoles with Polyfluoroarenes by Using Dioxygen as Oxidant journal February 2013
Crosslinking Using Rapid Thermal Processing for the Fabrication of Efficient Solution-Processed Phosphorescent Organic Light-Emitting Diodes journal January 2013
Carbazole electrochemistry: a short review journal August 2015
Excited state engineering for efficient reverse intersystem crossing journal June 2018
High performance blue-emitting organic light-emitting diodes from thermally activated delayed fluorescence: A guest/host ratio study journal August 2018
Ideal Molecular Design of Blue Thermally Activated Delayed Fluorescent Emitter for High Efficiency, Small Singlet–Triplet Energy Splitting, Low Efficiency Roll-Off, and Long Lifetime journal August 2016

Cited By (5)