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

Title: Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials

Journal Article · · Journal of Materials Chemistry C
DOI:https://doi.org/10.1039/C5TC03622D· OSTI ID:1259481
 [1];  [2];  [1];  [3];  [2];  [4];  [3];  [1];  [2];  [1]
  1. Iowa State Univ., Ames, IA (United States)
  2. Ames Lab. and Iowa State Univ., Ames, IA (United States)
  3. Univ. of North Georgia, Dahlonega, GA (United States)
  4. Ames Lab. and Iowa State Univ., Ames, IA (United States); National Univ. of Science & Technology (NUST MISiS), Moscow (Russia)

Four new cross-conjugated small molecules based on a central benzo[1,2-d:4,5-d']bisoxazole moiety possessing semi-independently tunable HOMO and LUMO levels were synthesized and the properties of these materials were evaluated experimentally and theoretically. The molecules were thermally stable with 5% weight loss occurring well above 350 °C. The cruciforms all exhibited blue emission in solution ranging from 433–450 nm. Host–guest OLEDs fabricated from various concentrations of these materials using the small molecule host 4,4'-bis(9-carbazolyl)-biphenyl (CBP) exhibited deep blue-emission with Commission Internationale de L'Eclairage (CIE) coordinates of (0.15 ≤ x ≤ 0.17, 0.05 ≤ y ≤ 0.11), and maximum luminance efficiencies as high as ~2 cd A–1. Lastly, these results demonstrate the potential of benzobisoxazole cruciforms as emitters for developing high-performance deep blue OLEDs.

Research Organization:
Ames Lab., Ames, IA (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
AC02-07CH11358; 0116435; 0521063; 0849677; 1229354; 1413173
OSTI ID:
1259481
Report Number(s):
IS-J-9011; JMCCCX
Journal Information:
Journal of Materials Chemistry C, Vol. 4, Issue 17; ISSN 2050-7526
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 38 works
Citation information provided by
Web of Science

References (45)

Collapse of stiff conjugated polymers with chemical defects into ordered, cylindrical conformations journal June 2000
Single chain spectroscopy of conformational dependence of conjugated polymer photophysics journal October 2000
Linear Monodisperse π-Conjugated Oligomers: Model Compounds for Polymers and More journal May 1999
Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission journal September 2011
From Short Conjugated Oligomers to Conjugated Polymers. Lessons from Studies on Long Conjugated Oligomers journal January 2011
Solution-processed small-molecule solar cells with 6.7% efficiency journal November 2011
α-Oligofurans journal February 2010
Thiophene-based conjugated oligomers for organic solar cells journal January 2011
Towards “green” electronic materials. α-Oligofurans as semiconductors journal January 2011
Small-molecule solar cells with efficiency over 9% journal November 2014
Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells journal April 2014
Blue-Light-Emitting Oligoquinolines: Synthesis, Properties, and High-Efficiency Blue-Light-Emitting Diodes journal April 2007
High-Efficiency Solution-Processed Small Molecule Electrophosphorescent Organic Light-Emitting Diodes journal July 2011
Cruciform π-systems: hybrid phenylene-ethynylene/phenylene-vinylene oligomers journal January 2003
Cross-Conjugated Cruciform Fluorophores journal March 2010
Hydroxycruciforms: Amine-Responsive Fluorophores journal May 2008
Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes journal March 2005
Systematic Structure−Property Investigations and Ion-Sensing Studies of Pyridine-Derivatized Donor/Acceptor Tetrakis(arylethynyl)benzenes journal January 2007
Structure−Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes journal March 2008
Two-Photon Absorption Properties of Two-Dimensional π-Conjugated Chromophores: Combined Experimental and Theoretical Study journal January 2011
X-Shaped Electro-optic Chromophore with Remarkably Blue-Shifted Optical Absorption. Synthesis, Characterization, Linear/Nonlinear Optical Properties, Self-Assembly, and Thin Film Microstructural Characteristics journal May 2006
Chemical Reactions with Upright Monolayers of Cruciform π-Systems journal November 2004
Cruciform π-Systems for Molecular Electronics Applications journal May 2003
Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles journal June 2013
Supramolecular organization of extended benzobisoxazole cruciforms journal January 2010
Benzobisoxazole Cruciforms: Heterocyclic Fluorophores with Spatially Separated Frontier Molecular Orbitals journal December 2011
Benzobisoxazole Cruciforms as Fluorescent Sensors journal April 2014
Selective and Sensitive Fluoride Detection through Alkyne Cruciform Desilylation journal June 2013
Identification of carboxylic and organoboronic acids and phenols with a single benzobisoxazole fluorophore journal January 2012
Effect of Extended Conjugation on the Optoelectronic Properties of Benzo[1,2-d:4,5-d′]bisoxazole Polymers journal January 2014
Altering the Conjugation Pathway for Improved Performance of Benzobisoxazole-Based Polymer Guest Emitters in Polymer Light-Emitting Diodes journal August 2012
Recent Advances in White Organic Light-Emitting Materials and Devices (WOLEDs) journal February 2010
Triplet Harvesting in Hybrid White Organic Light-Emitting Diodes journal May 2009
Solution-processable small molecules as efficient universal bipolar host for blue, green and red phosphorescent inverted OLEDs journal January 2012
Blue fluorescent emitters: design tactics and applications in organic light-emitting diodes journal January 2013
Recent advances of the emitters for high performance deep-blue organic light-emitting diodes journal January 2015
Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications journal April 2011
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model journal March 1998
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model journal April 2003
Highly efficient deep-blue organic electroluminescent devices (CIEy ≈ 0.08) doped with fluorinated 9,9′-bianthracene derivatives (fluorophores) journal January 2013
Fluorescent polymer guest:small molecule host solution-processed OLEDs journal January 2013
Exceedingly efficient deep-blue electroluminescence from new anthracenes obtained using rational molecular design journal January 2008
Tuning the Optical and Electronic Properties of 4,8-Disubstituted Benzobisoxazoles via Alkyne Substitution journal November 2011
Composition of “Polyphosphoric acid Trimethylsilyl Ester (Ppse)” and its use as a Condensation Reagent journal August 1982
Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report) journal August 2011

Cited By (6)

UV-Sensing Semitransparent Organic Field-Effect Transistors with Wide Bandgap Small Molecular Channel and Polymeric Gate-Insulating Layers journal September 2017
Donor‐/Acceptor‐Substituted Tetrakis(arylethynyl)benzenes: The Influence of Donor Group on Optoelectronic Properties journal June 2019
Phosphorus and silicon-bridged stilbenes: synthesis and optoelectronic properties journal January 2016
Trend breaking substitution pattern of phenothiazine with acceptors as a rational design platform for blue emitters journal January 2016
Regioselective copper-catalyzed direct arylation of benzodithiophene-S,S-tetraoxide journal January 2017
Effective modulation of intramolecular ferromagnetic interaction of diradicals by functionalization of cross-conjugated coupler journal January 2018

Similar Records

Rapid Multiscale Computational Screening for OLED Host Materials
Journal Article · Mon Jan 14 00:00:00 EST 2019 · ACS Applied Materials and Interfaces · OSTI ID:1259481

Modeling the Effect of Film Morphology on the Performance of an OLED Device
Technical Report · Tue Oct 06 00:00:00 EDT 2020 · OSTI ID:1259481

Improved Operational Stability of Blue Phosphorescent OLEDs by Functionalizing Phenyl‐Carbene Groups of Tetradentate Pt(II) Complexes
Journal Article · Sat Apr 13 00:00:00 EDT 2024 · Advanced Functional Materials · OSTI ID:1259481

Related Subjects