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

Idris, Muazzam; Coburn, Caleb; Fleetham, Tyler; Milam-Guerrero, JoAnna; Djurovich, Peter I.; Forrest, Stephen R.; Thompson, Mark E.

doi:10.1039/c9mh00195f

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

Journal Article · Mon Dec 31 23:00:00 EST 2018 · Materials Horizons

DOI:https://doi.org/10.1039/c9mh00195f· OSTI ID:1614017

^[1]; Coburn, Caleb ^[2]; Fleetham, Tyler ^[3]; Milam-Guerrero, JoAnna ^[3]; ^[3]; Forrest, Stephen R. ^[4]; ^[3]

Department of Chemistry; University of Southern California; Los Angeles; USA; DOE/OSTI
Department of Physics; University of Michigan; Ann Arbor; USA
Department of Chemistry; University of Southern California; Los Angeles; USA
Department of Physics; University of Michigan; Ann Arbor; USA; Department of Electrical and Computer Engineering

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).

Research Organization:: Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

DOE Contract Number:: EE0007077; EE0007626

OSTI ID:: 1614017

Journal Information:: Materials Horizons, Journal Name: Materials Horizons Journal Issue: 6 Vol. 6; ISSN 2051-6347; ISSN MHAOAL

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (41)

Below-one-volt organic thin-film transistors with large on/off current ratios Zschieschang, Ute; Bader, Vera Patricia; Klauk, Hagen Organic Electronics, Vol. 49 https://doi.org/10.1016/j.orgel.2017.06.045	journal	October 2017
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/ Adamovich, Vadim; Brooks, Jason; Tamayo, Arnold New Journal of Chemistry, Vol. 26, Issue 9 https://doi.org/10.1039/b204301g	journal	August 2002
Reliable, All-Phosphorescent Stacked White Organic Light Emitting Devices with a High Color Rendering Index Coburn, Caleb; Jeong, Changyeong; Forrest, Stephen R. ACS Photonics, Vol. 5, Issue 2 https://doi.org/10.1021/acsphotonics.7b01213	journal	November 2017
Rapid Multiscale Computational Screening for OLED Host Materials Sylvinson M. R., Daniel; Chen, Hsiao-Fan; Martin, Lauren M. ACS Applied Materials & Interfaces, Vol. 11, Issue 5 https://doi.org/10.1021/acsami.8b16225	journal	January 2019
Organic electroluminescent diodes Tang, C. W.; VanSlyke, S. A. Applied Physics Letters, Vol. 51, Issue 12 https://doi.org/10.1063/1.98799	journal	September 1987
One-pot Microwave-Assisted Synthesis of 1H-Phenanthro[9,10- d][1,2,3]triazole Taherpour, Avat Arman; Faraji, Mehrak Molbank, Vol. 2008, Issue 3 https://doi.org/10.3390/M577	journal	September 2008
Blue organic electrophosphorescence using exothermic host–guest energy transfer Holmes, R. J.; Forrest, S. R.; Tung, Y. -J. Applied Physics Letters, Vol. 82, Issue 15 https://doi.org/10.1063/1.1568146	journal	April 2003
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 Sworakowski, Juliusz; Lipiński, Józef; Janus, Krzysztof Organic Electronics, Vol. 33 https://doi.org/10.1016/j.orgel.2016.03.031	journal	June 2016
Synthesis and photo- and electroluminescence properties of 3,6-disubstituted phenanthrenes: alternative host material for blue fluorophores Chen, Yu-Han; Chou, Ho-Hsiu; Su, Tsu-Hui Chemical Communications, Vol. 47, Issue 31 https://doi.org/10.1039/c1cc12875b	journal	January 2011
Improved energy transfer in electrophosphorescent devices O’Brien, D. F.; Baldo, M. A.; Thompson, M. E. Applied Physics Letters, Vol. 74, Issue 3 https://doi.org/10.1063/1.123055	journal	January 1999
Triphenylene-based Host Materials for Low-voltage, Highly Efficient Red Phosphorescent Organic Light-emitting Diodes Togashi, Kazunori; Yasuda, Takuma; Adachi, Chihaya Chemistry Letters, Vol. 42, Issue 4 https://doi.org/10.1246/cl.121247	journal	April 2013
Simple Phenanthroimidazole/Carbazole Hybrid Bipolar Host Materials for Highly Efficient Green and Yellow Phosphorescent Organic Light-Emitting Diodes Huang, Hong; Wang, Yixin; Zhuang, Shaoqing The Journal of Physical Chemistry C, Vol. 116, Issue 36 https://doi.org/10.1021/jp305764b	journal	September 2012
RGB Phosphorescent Organic Light-Emitting Diodes by Using Host Materials with Heterocyclic Cores: Effect of Nitrogen Atom Orientations Su, Shi-Jian; Cai, Chao; Kido, Junji Chemistry of Materials, Vol. 23, Issue 2 https://doi.org/10.1021/cm102975d	journal	January 2011
High-Efficiency BODIPY-Based Organic Photovoltaics Chen, John J.; Conron, Sarah M.; Erwin, Patrick ACS Applied Materials & Interfaces, Vol. 7, Issue 1 https://doi.org/10.1021/am506874k	journal	December 2014
Deep blue organic light-emitting devices enabled by bipolar phenanthro[9,10-d]imidazole derivatives Chen, Shuo; Wu, Yukun; Zhao, Yi RSC Advances, Vol. 5, Issue 88 https://doi.org/10.1039/C5RA13814K	journal	January 2015
Operating lifetime of phosphorescent organic light emitting devices Burrows, P. E.; Forrest, S. R.; Zhou, T. X. Applied Physics Letters, Vol. 76, Issue 18 https://doi.org/10.1063/1.126386	journal	May 2000
Nearly 100% internal phosphorescence efficiency in an organic light-emitting device Adachi, Chihaya; Baldo, Marc A.; Thompson, Mark E. Journal of Applied Physics, Vol. 90, Issue 10 https://doi.org/10.1063/1.1409582	journal	November 2001
Quantitative phosphorescence spectroscopy of polystyrene during photo-degradation and the significance of in-chain peroxides George, G. A.; Hodgeman, D. K. C. European Polymer Journal, Vol. 13, Issue 1 https://doi.org/10.1016/0014-3057(77)90050-7	journal	January 1977
Highly efficient phosphorescent emission from organic electroluminescent devices Baldo, M. A.; O'Brien, D. F.; You, Y. Nature, Vol. 395, Issue 6698, p. 151-154 https://doi.org/10.1038/25954	journal	September 1998
Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles Ueda, Satoshi; Su, Mingjuan; Buchwald, Stephen L. Angewandte Chemie, Vol. 123, Issue 38 https://doi.org/10.1002/ange.201103882	journal	August 2011
Ultrahigh Energy Gap Hosts in Deep Blue Organic Electrophosphorescent Devices Ren, Xiaofan; Li, Jian; Holmes, Russell J. Chemistry of Materials, Vol. 16, Issue 23 https://doi.org/10.1021/cm049402m	journal	November 2004
Two‐layer organic photovoltaic cell Tang, C. W. Applied Physics Letters, Vol. 48, Issue 2 https://doi.org/10.1063/1.96937	journal	January 1986
Very high-efficiency green organic light-emitting devices based on electrophosphorescence Baldo, M. A.; Lamansky, S.; Burrows, P. E. Applied Physics Letters, Vol. 75, Issue 1, p. 4-6 https://doi.org/10.1063/1.124258	journal	July 1999
Organic Light-Emitting Devices for Solid-State Lighting So, Franky; Kido, Junji; Burrows, Paul MRS Bulletin, Vol. 33, Issue 7, p. 663-669 https://doi.org/10.1557/mrs2008.137	journal	July 2008
Donor-Substituted 1,3,5-Triazines as Host Materials for Blue Phosphorescent Organic Light-Emitting Diodes Rothmann, Michael M.; Haneder, Stephan; Da Como, Enrico Chemistry of Materials, Vol. 22, Issue 7 https://doi.org/10.1021/cm9033879	journal	April 2010
Confinement of triplet energy on phosphorescent molecules for highly-efficient organic blue-light-emitting devices Tokito, Shizuo; Iijima, Toshiki; Suzuri, Yoshiyuki Applied Physics Letters, Vol. 83, Issue 3 https://doi.org/10.1063/1.1594834	journal	July 2003
Above 30% External Quantum Efficiency in Blue Phosphorescent Organic Light-Emitting Diodes Using Pyrido[2,3- b ]indole Derivatives as Host Materials Lee, Chil Won; Lee, Jun Yeob Advanced Materials, Vol. 25, Issue 38 https://doi.org/10.1002/adma.201301091	journal	June 2013
Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles Taillefer, Marc; Xia, Ning; Ouali, Armelle Angewandte Chemie International Edition, Vol. 46, Issue 6 https://doi.org/10.1002/anie.200603173	journal	January 2007
Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations Alfonso, María; Espinosa, Arturo; Tárraga, Alberto ChemistryOpen, Vol. 3, Issue 6 https://doi.org/10.1002/open.201402022	journal	September 2014
Substitution reactions of phenanthro[9,10- d ]triazole with benzyl chlorides Yasuda, Goro; Kimoto, Hiroshi Journal of Heterocyclic Chemistry, Vol. 35, Issue 2 https://doi.org/10.1002/jhet.5570350218	journal	March 1998
Rational Design of Dibenzothiophene-Based Host Materials for PHOLEDs Dong, Shou-Cheng; Zhang, Lei; Liang, Jian The Journal of Physical Chemistry C, Vol. 118, Issue 5 https://doi.org/10.1021/jp412107g	journal	January 2014
Blue Light Emitting Ir(III) Compounds for OLEDs - New Insights into Ancillary Ligand Effects on the Emitting Triplet State Rausch, Andreas F.; Thompson, Mark E.; Yersin, Hartmut The Journal of Physical Chemistry A, Vol. 113, Issue 20 https://doi.org/10.1021/jp902261c	journal	May 2009
Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles Ueda, Satoshi; Su, Mingjuan; Buchwald, Stephen L. Angewandte Chemie International Edition, Vol. 50, Issue 38 https://doi.org/10.1002/anie.201103882	journal	August 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 Mani, Neelakandha S.; Fitzgerald, Anne E. The Journal of Organic Chemistry, Vol. 79, Issue 18 https://doi.org/10.1021/jo5013288	journal	August 2014
Influence of Halogen Atoms on a Homologous Series of Bis-Cyclometalated Iridium(III) Complexes Baranoff, Etienne; Curchod, Basile F. E.; Monti, Filippo Inorganic Chemistry, Vol. 51, Issue 2 https://doi.org/10.1021/ic2011474	journal	December 2011
Development and Application of O -(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes Chen, Qiao; Yu, Hongmei; Xu, Zhaoqing The Journal of Organic Chemistry, Vol. 80, Issue 13 https://doi.org/10.1021/acs.joc.5b00923	journal	June 2015
Tuning the nonlinear optical properties of BODIPYs by functionalization with dimethylaminostyryl substituents Kulyk, Bohdan; Taboukhat, Said; Akdas-Kilig, Huriye Dyes and Pigments, Vol. 137 https://doi.org/10.1016/j.dyepig.2016.10.045	journal	February 2017
Current-gain cutoff frequencies above 10 MHz for organic thin-film transistors with high mobility and low parasitic capacitance Kitamura, Masatoshi; Arakawa, Yasuhiko Applied Physics Letters, Vol. 95, Issue 2 https://doi.org/10.1063/1.3176480	journal	July 2009
Endothermic energy transfer: A mechanism for generating very efficient high-energy phosphorescent emission in organic materials Adachi, Chihaya; Kwong, Raymond C.; Djurovich, Peter Applied Physics Letters, Vol. 79, Issue 13 https://doi.org/10.1063/1.1400076	journal	September 2001
CN-Modified Host Materials for Improved Efficiency and Lifetime in Blue Phosphorescent and Thermally Activated Delayed Fluorescent Organic Light-Emitting Diodes Byeon, Sung Yong; Kim, Ji Han; Lee, Jun Yeob ACS Applied Materials & Interfaces, Vol. 9, Issue 15 https://doi.org/10.1021/acsami.6b15502	journal	April 2017
Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles. Taillefer, Marc; Xia, Ning; Ouali, Armelle ChemInform, Vol. 38, Issue 18 https://doi.org/10.1002/chin.200718100	journal	May 2007

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