Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials
Abstract
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.
- Authors:
-
- Iowa State Univ., Ames, IA (United States)
- Ames Lab. and Iowa State Univ., Ames, IA (United States)
- Univ. of North Georgia, Dahlonega, GA (United States)
- Ames Lab. and Iowa State Univ., Ames, IA (United States); National Univ. of Science & Technology (NUST MISiS), Moscow (Russia)
- Publication Date:
- Research Org.:
- Ames Lab., Ames, IA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1259481
- Report Number(s):
- IS-J-9011
Journal ID: ISSN 2050-7526; JMCCCX
- Grant/Contract Number:
- AC02-07CH11358; 0116435; 0521063; 0849677; 1229354; 1413173
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Materials Chemistry C
- Additional Journal Information:
- Journal Volume: 4; Journal Issue: 17; Journal ID: ISSN 2050-7526
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Chavez, III, Ramiro, Cai, Min, Tlach, Brian, Wheeler, David L., Kaudal, Rajiv, Tsyrenova, Ayuna, Tomlinson, Aimee L., Shinar, Ruth, Shinar, Joseph, and Jeffries-EL, Malika. Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials. United States: N. p., 2016.
Web. doi:10.1039/C5TC03622D.
Chavez, III, Ramiro, Cai, Min, Tlach, Brian, Wheeler, David L., Kaudal, Rajiv, Tsyrenova, Ayuna, Tomlinson, Aimee L., Shinar, Ruth, Shinar, Joseph, & Jeffries-EL, Malika. Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials. United States. https://doi.org/10.1039/C5TC03622D
Chavez, III, Ramiro, Cai, Min, Tlach, Brian, Wheeler, David L., Kaudal, Rajiv, Tsyrenova, Ayuna, Tomlinson, Aimee L., Shinar, Ruth, Shinar, Joseph, and Jeffries-EL, Malika. Wed .
"Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials". United States. https://doi.org/10.1039/C5TC03622D. https://www.osti.gov/servlets/purl/1259481.
@article{osti_1259481,
title = {Benzobisoxazole cruciforms: A tunable, cross-conjugated platform for the generation of deep blue OLED materials},
author = {Chavez, III, Ramiro and Cai, Min and Tlach, Brian and Wheeler, David L. and Kaudal, Rajiv and Tsyrenova, Ayuna and Tomlinson, Aimee L. and Shinar, Ruth and Shinar, Joseph and Jeffries-EL, Malika},
abstractNote = {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.},
doi = {10.1039/C5TC03622D},
journal = {Journal of Materials Chemistry C},
number = 17,
volume = 4,
place = {United States},
year = {Wed Jan 20 00:00:00 EST 2016},
month = {Wed Jan 20 00:00:00 EST 2016}
}
Web of Science
Works referenced in this record:
Collapse of stiff conjugated polymers with chemical defects into ordered, cylindrical conformations
journal, June 2000
- Hu, Dehong; Yu, Ji; Wong, Kim
- Nature, Vol. 405, Issue 6790
Single chain spectroscopy of conformational dependence of conjugated polymer photophysics
journal, October 2000
- Huser, T.; Yan, M.; Rothberg, L. J.
- Proceedings of the National Academy of Sciences, Vol. 97, Issue 21
Linear Monodisperse π-Conjugated Oligomers: Model Compounds for Polymers and More
journal, May 1999
- Martin, Rainer E.; Diederich, François
- Angewandte Chemie International Edition, Vol. 38, Issue 10
Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission
journal, September 2011
- Ellinger, Stefan; Graham, Kenneth R.; Shi, Pengjie
- Chemistry of Materials, Vol. 23, Issue 17
From Short Conjugated Oligomers to Conjugated Polymers. Lessons from Studies on Long Conjugated Oligomers
journal, January 2011
- Zade, Sanjio S.; Zamoshchik, Natalia; Bendikov, Michael
- Accounts of Chemical Research, Vol. 44, Issue 1
Solution-processed small-molecule solar cells with 6.7% efficiency
journal, November 2011
- Sun, Yanming; Welch, Gregory C.; Leong, Wei Lin
- Nature Materials, Vol. 11, Issue 1, p. 44-48
α-Oligofurans
journal, February 2010
- Gidron, Ori; Diskin-Posner, Yael; Bendikov, Michael
- Journal of the American Chemical Society, Vol. 132, Issue 7
Thiophene-based conjugated oligomers for organic solar cells
journal, January 2011
- Zhang, Fan; Wu, Dongqing; Xu, Youyong
- Journal of Materials Chemistry, Vol. 21, Issue 44
Towards “green” electronic materials. α-Oligofurans as semiconductors
journal, January 2011
- Gidron, Ori; Dadvand, Afshin; Sheynin, Yana
- Chem. Commun., Vol. 47, Issue 7
Small-molecule solar cells with efficiency over 9%
journal, November 2014
- Zhang, Qian; Kan, Bin; Liu, Feng
- Nature Photonics, Vol. 9, Issue 1
Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells
journal, April 2014
- Liu, Xiaofeng; Sun, Yanming; Hsu, Ben B. Y.
- Journal of the American Chemical Society, Vol. 136, Issue 15
Blue-Light-Emitting Oligoquinolines: Synthesis, Properties, and High-Efficiency Blue-Light-Emitting Diodes
journal, April 2007
- Tonzola, C. J.; Kulkarni, A. P.; Gifford, A. P.
- Advanced Functional Materials, Vol. 17, Issue 6
High-Efficiency Solution-Processed Small Molecule Electrophosphorescent Organic Light-Emitting Diodes
journal, July 2011
- Cai, Min; Xiao, Teng; Hellerich, Emily
- Advanced Materials, Vol. 23, Issue 31
Cruciform π-systems: hybrid phenylene-ethynylene/phenylene-vinylene oligomers
journal, January 2003
- Wilson, James N.; Josowicz, Mira; Wang, Yiqing
- Chem. Commun., Issue 24
Cross-Conjugated Cruciform Fluorophores
journal, March 2010
- Zucchero, Anthony J.; McGrier, Psaras L.; Bunz, Uwe H. F.
- Accounts of Chemical Research, Vol. 43, Issue 3
Hydroxycruciforms: Amine-Responsive Fluorophores
journal, May 2008
- McGrier, Psaras L.; Solntsev, Kyril M.; Miao, Shaobin
- Chemistry - A European Journal, Vol. 14, Issue 15
Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
journal, March 2005
- Marsden, Jeremiah A.; Miller, Jeremie J.; Shirtcliff, Laura D.
- Journal of the American Chemical Society, Vol. 127, Issue 8
Systematic Structure−Property Investigations and Ion-Sensing Studies of Pyridine-Derivatized Donor/Acceptor Tetrakis(arylethynyl)benzenes
journal, January 2007
- Spitler, Eric L.; Shirtcliff, Laura D.; Haley, Michael M.
- The Journal of Organic Chemistry, Vol. 72, Issue 1
Structure−Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
journal, March 2008
- Spitler, Eric L.; Monson, John M.; Haley, Michael M.
- The Journal of Organic Chemistry, Vol. 73, Issue 6
Two-Photon Absorption Properties of Two-Dimensional π-Conjugated Chromophores: Combined Experimental and Theoretical Study
journal, January 2011
- Ohta, Koji; Yamada, Satoru; Kamada, Kenji
- The Journal of Physical Chemistry A, Vol. 115, Issue 2
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
- Kang, Hu; Evmenenko, Guennadi; Dutta, Pulak
- Journal of the American Chemical Society, Vol. 128, Issue 18
Chemical Reactions with Upright Monolayers of Cruciform π-Systems
journal, November 2004
- Klare, Jennifer E.; Tulevski, George S.; Nuckolls, Colin
- Langmuir, Vol. 20, Issue 23
Cruciform π-Systems for Molecular Electronics Applications
journal, May 2003
- Klare, Jennifer E.; Tulevski, George S.; Sugo, Kenji
- Journal of the American Chemical Society, Vol. 125, Issue 20
Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles
journal, June 2013
- Tlach, Brian C.; Tomlinson, Aimée L.; Ryno, Alden G.
- The Journal of Organic Chemistry, Vol. 78, Issue 13
Supramolecular organization of extended benzobisoxazole cruciforms
journal, January 2010
- Osowska, Karolina; Miljanić, Ognjen Š.
- Chemical Communications, Vol. 46, Issue 24
Benzobisoxazole Cruciforms: Heterocyclic Fluorophores with Spatially Separated Frontier Molecular Orbitals
journal, December 2011
- Lim, Jaebum; Albright, Thomas A.; Martin, Benjamin R.
- The Journal of Organic Chemistry, Vol. 76, Issue 24
Benzobisoxazole Cruciforms as Fluorescent Sensors
journal, April 2014
- Saeed, Musabbir A.; Le, Ha T. M.; Miljanić, Ognjen Š.
- Accounts of Chemical Research, Vol. 47, Issue 7
Selective and Sensitive Fluoride Detection through Alkyne Cruciform Desilylation
journal, June 2013
- Jo, Minyoung; Lim, Jaebum; Miljanić, Ognjen Š.
- Organic Letters, Vol. 15, Issue 14
Identification of carboxylic and organoboronic acids and phenols with a single benzobisoxazole fluorophore
journal, January 2012
- Lim, Jaebum; Nam, Dolly; Miljanić, Ognjen Š.
- Chem. Sci., Vol. 3, Issue 2
Effect of Extended Conjugation on the Optoelectronic Properties of Benzo[1,2-d:4,5-d′]bisoxazole Polymers
journal, January 2014
- Tlach, Brian C.; Tomlinson, Aimée L.; Morgan, Kiley D.
- Australian Journal of Chemistry, Vol. 67, Issue 5
Altering the Conjugation Pathway for Improved Performance of Benzobisoxazole-Based Polymer Guest Emitters in Polymer Light-Emitting Diodes
journal, August 2012
- Intemann, Jeremy J.; Hellerich, Emily S.; Tlach, Brian C.
- Macromolecules, Vol. 45, Issue 17
Recent Advances in White Organic Light-Emitting Materials and Devices (WOLEDs)
journal, February 2010
- Kamtekar, Kiran T.; Monkman, Andrew P.; Bryce, Martin R.
- Advanced Materials, Vol. 22, Issue 5
Triplet Harvesting in Hybrid White Organic Light-Emitting Diodes
journal, May 2009
- Schwartz, Gregor; Reineke, Sebastian; Rosenow, Thomas Conrad
- Advanced Functional Materials, Vol. 19, Issue 9
Solution-processable small molecules as efficient universal bipolar host for blue, green and red phosphorescent inverted OLEDs
journal, January 2012
- Chen, Jiangshan; Shi, Changsheng; Fu, Qiang
- Journal of Materials Chemistry, Vol. 22, Issue 11
Blue fluorescent emitters: design tactics and applications in organic light-emitting diodes
journal, January 2013
- Zhu, Minrong; Yang, Chuluo
- Chemical Society Reviews, Vol. 42, Issue 12
Recent advances of the emitters for high performance deep-blue organic light-emitting diodes
journal, January 2015
- Yang, Xiaolong; Xu, Xianbin; Zhou, Guijiang
- Journal of Materials Chemistry C, Vol. 3, Issue 5
Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications
journal, April 2011
- Cardona, Claudia M.; Li, Wei; Kaifer, Angel E.
- Advanced Materials, Vol. 23, Issue 20
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model
journal, March 1998
- Barone, Vincenzo; Cossi, Maurizio
- The Journal of Physical Chemistry A, Vol. 102, Issue 11
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model
journal, April 2003
- Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni
- Journal of Computational Chemistry, Vol. 24, Issue 6
Highly efficient deep-blue organic electroluminescent devices (CIEy ≈ 0.08) doped with fluorinated 9,9′-bianthracene derivatives (fluorophores)
journal, January 2013
- Yu, Yue; Wu, Zhaoxin; Li, Zhanfeng
- Journal of Materials Chemistry C, Vol. 1, Issue 48
Fluorescent polymer guest:small molecule host solution-processed OLEDs
journal, January 2013
- Hellerich, Emily S.; Intemann, Jeremy J.; Cai, Min
- Journal of Materials Chemistry C, Vol. 1, Issue 34
Exceedingly efficient deep-blue electroluminescence from new anthracenes obtained using rational molecular design
journal, January 2008
- Kim, Soo-Kang; Yang, Bing; Ma, Yuguang
- Journal of Materials Chemistry, Vol. 18, Issue 28
Tuning the Optical and Electronic Properties of 4,8-Disubstituted Benzobisoxazoles via Alkyne Substitution
journal, November 2011
- Tlach, Brian C.; Tomlinson, Aimée L.; Bhuwalka, Achala
- The Journal of Organic Chemistry, Vol. 76, Issue 21
Composition of “Polyphosphoric acid Trimethylsilyl Ester (Ppse)” and its use as a Condensation Reagent
journal, August 1982
- Yamamoto, Keiji; Watanabe, Hiroyuki
- Chemistry Letters, Vol. 11, Issue 8
Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report)
journal, August 2011
- Brouwer, Albert M.
- Pure and Applied Chemistry, Vol. 83, Issue 12
Works referencing / citing this record:
UV-Sensing Semitransparent Organic Field-Effect Transistors with Wide Bandgap Small Molecular Channel and Polymeric Gate-Insulating Layers
journal, September 2017
- Lee, Chulyeon; Lee, Sooyong; Kim, Hwajeong
- Advanced Electronic Materials, Vol. 3, Issue 10
Donor‐/Acceptor‐Substituted Tetrakis(arylethynyl)benzenes: The Influence of Donor Group on Optoelectronic Properties
journal, June 2019
- Nojo, Wataru; Reingold, I. David; Bard, Jeremy P.
- ChemPlusChem, Vol. 84, Issue 9
Phosphorus and silicon-bridged stilbenes: synthesis and optoelectronic properties
journal, January 2016
- Zhou, Yang; Yang, Shuai; Li, Jun
- Dalton Transactions, Vol. 45, Issue 45
Trend breaking substitution pattern of phenothiazine with acceptors as a rational design platform for blue emitters
journal, January 2016
- Kumar, Sunil; Singh, Meenu; Jou, Jwo-Huei
- Journal of Materials Chemistry C, Vol. 4, Issue 28
Regioselective copper-catalyzed direct arylation of benzodithiophene-S,S-tetraoxide
journal, January 2017
- Khambhati, D. P.; Sachinthani, K. A. N.; Rheingold, A. L.
- Chemical Communications, Vol. 53, Issue 37
Effective modulation of intramolecular ferromagnetic interaction of diradicals by functionalization of cross-conjugated coupler
journal, January 2018
- Burnea, Francis Kirby B.; Ko, Kyoung Chul; Lee, Jin Yong
- Physical Chemistry Chemical Physics, Vol. 20, Issue 31