Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes
Abstract
Spiro[fluorene-9,9'-xanthene] (SFX) bipolar hosts bearing one, two and three quinolyl substituents, namely SFX-bPy, SFX-DbPy and SFX-TbPy, were designed and synthesized for phosphorescent organic light emitting diodes (PhOLEDs). The successive substitution of quinoline at 2', 2 and 7' positions of SFX results in reduced LUMO energy levels while leaving the HOMO energy levels nearly intact. The impact of quinoline substitution in these SFX-based hosts on PhOLED performance was investigated in detail through green and red model devices. For the green emitting devices, the device based on SFX-bPy host showed better performance (23.6 cd A-1, 23.4 lm W-1, 6.3%) due to high triplet energy level (T1) and balanced carriers-transporting ability. In contrast, for the red PhOLED devices, the device hosted by SFX-DbPy displayed higher performance (15.8 cd A-1, 16.0 lm W-1, 9.1%), attributable to the well matched T1 and separated frontier molecular orbitals. This work thus sheds light on the rational design of SFX-based bipolar hosts for more efficient PhOLEDs.
- Authors:
-
- Shenyang Univ. of Chemical Technology, Shenyang (China); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Shenyang Univ. of Chemical Technology, Shenyang (China)
- Xinyang Normal Univ., Xinyang (China)
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Northeast Forestry Univ., Harbin (China)
- Jilin Univ., Changchun (China)
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1530248
- Alternate Identifier(s):
- OSTI ID: 1351661
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Organic Electronics
- Additional Journal Information:
- Journal Volume: 36; Journal Issue: C; Journal ID: ISSN 1566-1199
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Ren, Bao-Yi, Zhong, Dao-Kun, Sun, Ya-Guang, Zhao, Xiang-Hua, Zhang, Qi-Jian, Liu, Yi, Jurow, Matthew, Sun, Ming-Li, Zhang, Zhen-Song, and Zhao, Yi. Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes. United States: N. p., 2016.
Web. doi:10.1016/j.orgel.2016.06.006.
Ren, Bao-Yi, Zhong, Dao-Kun, Sun, Ya-Guang, Zhao, Xiang-Hua, Zhang, Qi-Jian, Liu, Yi, Jurow, Matthew, Sun, Ming-Li, Zhang, Zhen-Song, & Zhao, Yi. Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes. United States. https://doi.org/10.1016/j.orgel.2016.06.006
Ren, Bao-Yi, Zhong, Dao-Kun, Sun, Ya-Guang, Zhao, Xiang-Hua, Zhang, Qi-Jian, Liu, Yi, Jurow, Matthew, Sun, Ming-Li, Zhang, Zhen-Song, and Zhao, Yi. Thu .
"Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes". United States. https://doi.org/10.1016/j.orgel.2016.06.006. https://www.osti.gov/servlets/purl/1530248.
@article{osti_1530248,
title = {Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes},
author = {Ren, Bao-Yi and Zhong, Dao-Kun and Sun, Ya-Guang and Zhao, Xiang-Hua and Zhang, Qi-Jian and Liu, Yi and Jurow, Matthew and Sun, Ming-Li and Zhang, Zhen-Song and Zhao, Yi},
abstractNote = {Spiro[fluorene-9,9'-xanthene] (SFX) bipolar hosts bearing one, two and three quinolyl substituents, namely SFX-bPy, SFX-DbPy and SFX-TbPy, were designed and synthesized for phosphorescent organic light emitting diodes (PhOLEDs). The successive substitution of quinoline at 2', 2 and 7' positions of SFX results in reduced LUMO energy levels while leaving the HOMO energy levels nearly intact. The impact of quinoline substitution in these SFX-based hosts on PhOLED performance was investigated in detail through green and red model devices. For the green emitting devices, the device based on SFX-bPy host showed better performance (23.6 cd A-1, 23.4 lm W-1, 6.3%) due to high triplet energy level (T1) and balanced carriers-transporting ability. In contrast, for the red PhOLED devices, the device hosted by SFX-DbPy displayed higher performance (15.8 cd A-1, 16.0 lm W-1, 9.1%), attributable to the well matched T1 and separated frontier molecular orbitals. This work thus sheds light on the rational design of SFX-based bipolar hosts for more efficient PhOLEDs.},
doi = {10.1016/j.orgel.2016.06.006},
journal = {Organic Electronics},
number = C,
volume = 36,
place = {United States},
year = {Thu Jun 09 00:00:00 EDT 2016},
month = {Thu Jun 09 00:00:00 EDT 2016}
}
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Works referenced in this record:
Highly efficient phosphorescent emission from organic electroluminescent devices
journal, September 1998
- Baldo, M. A.; O'Brien, D. F.; You, Y.
- Nature, Vol. 395, Issue 6698, p. 151-154
White phosphorescent LEDs offer efficient answer
journal, January 2007
- D'Andrade, Brian
- Nature Photonics, Vol. 1, Issue 1
m -Indolocarbazole Derivative as a Universal Host Material for RGB and White Phosphorescent OLEDs
journal, August 2015
- Lai, Cheng-Chang; Huang, Min-Jie; Chou, Ho-Hsiu
- Advanced Functional Materials, Vol. 25, Issue 34
Organic host materials for phosphorescent organic light-emitting diodes
journal, January 2011
- Tao, Youtian; Yang, Chuluo; Qin, Jingui
- Chemical Society Reviews, Vol. 40, Issue 5
Solution-Processable Hosts Constructed by Carbazole/PO Substituted Tetraphenylsilanes for Efficient Blue Electrophosphorescent Devices
journal, July 2014
- Liu, He; Bai, Qing; Yao, Liang
- Advanced Functional Materials, Vol. 24, Issue 37
A Simple Carbazole/Oxadiazole Hybrid Molecule: An Excellent Bipolar Host for Green and Red Phosphorescent OLEDs
journal, October 2008
- Tao, Youtian; Wang, Qiang; Yang, Chuluo
- Angewandte Chemie, Vol. 120, Issue 42
Diarylmethylene-bridged triphenylamine derivatives encapsulated with fluorene: very high Tg host materials for efficient blue and green phosphorescent OLEDs
journal, January 2010
- Fan, Cong; Chen, Yonghua; Jiang, Zuoquan
- Journal of Materials Chemistry, Vol. 20, Issue 16
Molecular Topology Tuning of Bipolar Host Materials Composed of Fluorene-Bridged Benzimidazole and Carbazole for Highly Efficient Electrophosphorescence
journal, June 2013
- Mondal, Ejabul; Hung, Wen-Yi; Chen, Yang-Huei
- Chemistry - A European Journal, Vol. 19, Issue 32
Efficient Deep-Blue Electroluminescence from an Ambipolar Fluorescent Emitter in a Single-Active-Layer Device
journal, April 2011
- Fisher, Alison L.; Linton, Katharine E.; Kamtekar, Kiran T.
- Chemistry of Materials, Vol. 23, Issue 7
Dependence of the Properties of Dihydroindenofluorene Derivatives on Positional Isomerism: Influence of the Ring Bridging
journal, November 2013
- Romain, Maxime; Tondelier, Denis; Vanel, Jean-Charles
- Angewandte Chemie International Edition, Vol. 52, Issue 52
Spirobifluorene-2,7-dicarbazole-4′-phosphine Oxide as Host for High-Performance Single-Layer Green Phosphorescent OLED Devices
journal, September 2015
- Thiery, Sébastien; Tondelier, Denis; Geffroy, Bernard
- Organic Letters, Vol. 17, Issue 19
A Novel Class of Emitting Amorphous Molecular Materials as Bipolar Radical Formants: 2-{4-[Bis(4-methylphenyl)amino]phenyl}- 5-(dimesitylboryl)thiophene and 2-{4-[Bis(9,9-dimethylfluorenyl)amino]phenyl}- 5-(dimesitylboryl)thiophene
journal, November 2000
- Shirota, Yasuhiko; Kinoshita, Motoi; Noda, Tetsuya
- Journal of the American Chemical Society, Vol. 122, Issue 44
Highly efficient orange and deep-red organic light emitting diodes with long operational lifetimes using carbazole–quinoline based bipolar host materials
journal, January 2014
- Chen, Chin-Hsien; Hsu, Lun-Chia; Rajamalli, P.
- J. Mater. Chem. C, Vol. 2, Issue 30
Enhanced Electroluminescence Efficiency in a Spiro-Acridine Derivative through Thermally Activated Delayed Fluorescence
journal, October 2012
- Méhes, Gábor; Nomura, Hiroko; Zhang, Qisheng
- Angewandte Chemie International Edition, Vol. 51, Issue 45
Properties modulation of organic semi-conductors based on a donor-spiro-acceptor (D-spiro-A) molecular design: new host materials for efficient sky-blue PhOLEDs
journal, January 2015
- Romain, Maxime; Tondelier, Denis; Jeannin, Olivier
- Journal of Materials Chemistry C, Vol. 3, Issue 37
Donor/Acceptor Dihydroindeno[1,2- a ]fluorene and Dihydroindeno[2,1- b ]fluorene: Towards New Families of Organic Semiconductors
journal, May 2015
- Romain, Maxime; Tondelier, Denis; Geffroy, Bernard
- Chemistry - A European Journal, Vol. 21, Issue 26
Tetraphenylsilane derivatives spiro-annulated by triphenylamine/carbazole with enhanced HOMO energy levels and glass transition temperatures without lowering triplet energy: host materials for efficient blue phosphorescent OLEDs
journal, January 2013
- Fan, Cong; Chen, Yonghua; Liu, Zhongyin
- J. Mater. Chem. C, Vol. 1, Issue 3
Spiro-configured phenyl acridine thioxanthene dioxide as a host for efficient PhOLEDs
journal, January 2015
- Romain, Maxime; Tondelier, Denis; Geffroy, Bernard
- Chemical Communications, Vol. 51, Issue 7
Spiro-configured bipolar hosts incorporating 4,5-diazafluroene as the electron transport moiety for highly efficient red and green phosphorescent OLEDs
journal, January 2012
- Chen, Hsiao-Fan; Wang, Ting-Chih; Hung, Wen-Yi
- Journal of Materials Chemistry, Vol. 22, Issue 19
Tri-, Tetra- and Pentamers of 9,9′-Spirobifluorenes through Full ortho -Linkage: High Triplet-Energy Pure Hydrocarbon Host for Blue Phosphorescent Emitter
journal, December 2010
- Fan, Cong; Chen, Yonghua; Gan, Pei
- Organic Letters, Vol. 12, Issue 24
Morphological Stable Spirobifluorene/Oxadiazole Hybrids as Bipolar Host Materials for Efficient Green and Red Electrophosphorescence
journal, February 2010
- Tao, Youtian; Ao, Liang; Wang, Qiang
- Chemistry - An Asian Journal, Vol. 5, Issue 2
Spiro Compounds for Organic Optoelectronics
journal, April 2007
- Saragi, Tobat P. I.; Spehr, Till; Siebert, Achim
- Chemical Reviews, Vol. 107, Issue 4
Spiro-Configured Bipolar Host Materials for Highly Efficient Electrophosphorescent Devices
journal, October 2011
- Ku, Sung-Yu; Hung, Wen-Yi; Chen, Chung-Wen
- Chemistry - An Asian Journal, Vol. 7, Issue 1
Construction of thermally stable 3,6-disubstituted spiro-fluorene derivatives as host materials for blue phosphorescent organic light-emitting diodes
journal, March 2015
- Wang, Lei; Pan, Biao; Zhu, Liping
- Dyes and Pigments, Vol. 114
4-Pyridyl-9,9′-spirobifluorenes as Host Materials for Green and Sky-Blue Phosphorescent OLEDs
journal, March 2015
- Thiery, Sébastien; Tondelier, Denis; Declairieux, Céline
- The Journal of Physical Chemistry C, Vol. 119, Issue 11
Pure Hydrocarbon Hosts for ≈100% Exciton Harvesting in Both Phosphorescent and Fluorescent Light-Emitting Devices
journal, June 2015
- Cui, Lin-Song; Xie, Yue-Min; Wang, Ya-Kun
- Advanced Materials, Vol. 27, Issue 28
Unexpected One-Pot Method to Synthesize Spiro[fluorene-9,9‘-xanthene] Building Blocks for Blue-Light-Emitting Materials
journal, June 2006
- Xie, Ling-Hai; Liu, Feng; Tang, Chao
- Organic Letters, Vol. 8, Issue 13
Spirocyclic Aromatic Hydrocarbons (SAHs) and their Synthetic Methodologies
journal, November 2010
- Xie, Ling-Hai; Liang, Jing; Song, Juan
- Current Organic Chemistry, Vol. 14, Issue 18
SFX as a low-cost ‘Spiro’ hole-transport material for efficient perovskite solar cells
journal, January 2016
- Maciejczyk, Michal; Ivaturi, Aruna; Robertson, Neil
- Journal of Materials Chemistry A, Vol. 4, Issue 13
A low-cost spiro[fluorene-9,9′-xanthene]-based hole transport material for highly efficient solid-state dye-sensitized solar cells and perovskite solar cells
journal, January 2016
- Xu, Bo; Bi, Dongqin; Hua, Yong
- Energy & Environmental Science, Vol. 9, Issue 3
Organosolubility and optical transparency of novel polyimides derived from 2′,7′-bis(4-aminophenoxy)-spiro(fluorene-9,9′-xanthene)
journal, January 2010
- Zhang, ShuJiang; Li, YanFen; Ma, Tao
- Polymer Chemistry, Vol. 1, Issue 4
螺芴氧杂蒽(SFX)类有机半导体及其OLEDs
journal, May 2015
- Huang, Wei; Xie, LingHai; Zhang, XiaoNi
- Chinese Science Bulletin, Vol. 60, Issue 14
Dumbbell-Shaped Spirocyclic Aromatic Hydrocarbon to Control Intermolecular π−π Stacking Interaction for High-Performance Nondoped Deep-Blue Organic Light-Emitting Devices
journal, September 2010
- Gu, Ju-Fen; Xie, Guo-Hua; Zhang, Long
- The Journal of Physical Chemistry Letters, Vol. 1, Issue 19
Nondoped deep-blue spirofluorenexanthene-based green organic semiconductors (GOS) via a pot, atom and step economic (PASE) route combining direct arylation with tandem reaction
journal, January 2015
- Sun, Ming-Li; Zhu, Wen-Sai; Zhang, Zhen-Song
- Journal of Materials Chemistry C, Vol. 3, Issue 1
DiSpiroXanthene-IndenoFluorene: A New Blue Emitter for Nondoped Organic Light Emitting Diode Applications
journal, December 2009
- Cocherel, Nicolas; Poriel, Cyril; Vignau, Laurence
- Organic Letters, Vol. 12, Issue 3
Incorporation of Spiroxanthene Units in Blue-Emitting Oligophenylene Frameworks: A New Molecular Design for OLED Applications
journal, September 2011
- Poriel, Cyril; Cocherel, Nicolas; Rault-Berthelot, Joëlle
- Chemistry - A European Journal, Vol. 17, Issue 45
Harmonizing Triplet Level and Ambipolar Characteristics of Wide-Gap Phosphine Oxide Hosts toward Highly Efficient and Low Driving Voltage Blue and Green PHOLEDs: An Effective Strategy Based on Spiro-Systems
journal, December 2011
- Zhao, Jie; Xie, Guo-Hua; Yin, Cheng-Rong
- Chemistry of Materials, Vol. 23, Issue 24
Triphenyl phosphine oxide-bridged bipolar host materials for green and red phosphorescent organic light-emitting diodes
journal, December 2015
- Zhang, Qingwei; Fang, Da; Jiang, Hongji
- Organic Electronics, Vol. 27
Spirofluorene-Based Blue Phosphorescent Organic Light-Emitting Diode with Improved Efficiency Using Co-Host Structure
journal, January 2015
- Sun, Mingli; Guan, Yuqiao; Liu, Bin
- General Chemistry, Vol. 1, Issue 1
Spiro[fluorene-9,9′-xanthene]-based universal hosts for understanding structure–property relationships in RGB and white PhOLEDs
journal, January 2015
- Qian, Yan; Ni, Yeren; Yue, Shouzhen
- RSC Advances, Vol. 5, Issue 38
A new spiro[fluorene-9,9′-xanthene]-based host material possessing no conventional hole- and electron-transporting units for efficient and low voltage blue PHOLED via simple two-step synthesis
journal, November 2012
- Qian, Yan; Xie, Guohua; Chen, Shufen
- Organic Electronics, Vol. 13, Issue 11
Dimeric SFX host materials for red, green and blue phosphorescent organic light-emitting devices
journal, September 2014
- Sun, Ming-Li; Yue, Shou-Zhen; Lin, Jun-Rui
- Synthetic Metals, Vol. 195
A Significantly Twisted Spirocyclic Phosphine Oxide as a Universal Host for High-Efficiency Full-Color Thermally Activated Delayed Fluorescence Diodes
journal, February 2016
- Li, Jing; Ding, Dongxue; Tao, Youtian
- Advanced Materials, Vol. 28, Issue 16
Highly photo- and electroluminescent 1,3-diketonate Eu(iii) complexes with spiro-fluorene-xantphos dioxide ligands: synthesis and properties
journal, January 2013
- Pietraszkiewicz, Marek; Maciejczyk, Michal; Samuel, Ifor D. W.
- Journal of Materials Chemistry C, Vol. 1, Issue 48
A 3-dimensional spiro-functionalized platinum(ii) complex to suppress intermolecular π–π and Pt⋯Pt supramolecular interactions for a high-performance electrophosphorescent device
journal, January 2012
- Zhao, Xiang-Hua; Xie, Guo-Hua; Liu, Zheng-Dong
- Chemical Communications, Vol. 48, Issue 32
Synthesis of spiro[fluorene-9,9′-xanthene] derivatives and their application as hole-transporting materials for organic light-emitting devices
journal, May 2012
- Chu, Zengze; Wang, Dan; Zhang, Chao
- Synthetic Metals, Vol. 162, Issue 7-8
Thin-film processing and optical properties of conjugated rigid-rod polyquinolines for nonlinear optical applications
journal, January 1992
- Agrawal, Ashwini K.; Jenekhe, Samson A.
- Chemistry of Materials, Vol. 4, Issue 1
Synthesis and processing of heterocyclic polymers as electronic, optoelectronic, and nonlinear optical materials. 2. New series of conjugated rigid-rod polyquinolines and polyanthrazolines
journal, March 1993
- Agrawal, Ashwini K.; Jenekhe, Samson A.
- Macromolecules, Vol. 26, Issue 5
Oligothiophene Semiconductors: Synthesis, Characterization, and Applications for Organic Devices
journal, March 2014
- Zhang, Lei; Colella, Nicholas S.; Cherniawski, Benjamin P.
- ACS Applied Materials & Interfaces, Vol. 6, Issue 8
Synthetic Chemistry for Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors
journal, March 2001
- Katz, Howard E.; Bao, Zhenan; Gilat, Sylvain L.
- Accounts of Chemical Research, Vol. 34, Issue 5, p. 359-369
New Dopant and Host Materials for Blue-Light-Emitting Phosphorescent Organic Electroluminescent Devices
journal, February 2005
- Yeh, S. -J.; Wu, M. -F.; Chen, C. -T.
- Advanced Materials, Vol. 17, Issue 3
Asymmetric Design of Bipolar Host Materials with Novel 1,2,4-Oxadiazole Unit in Blue Phosphorescent Device
journal, March 2014
- Li, Qian; Cui, Lin-Song; Zhong, Cheng
- Organic Letters, Vol. 16, Issue 6
New spirobenzoanthracene derivatives with naphthylanthracene core: Synthesis and application in sky-blue fluorescent host materials
journal, June 2014
- Kim, Min-Ji; Lee, Chil-Won; Gong, Myoung-Seon
- Dyes and Pigments, Vol. 105
Highly Efficient Red Phosphorescent Dopants in Organic Light-Emitting Devices
journal, April 2011
- Kim, Do Han; Cho, Nam Sung; Oh, Hyoung-Yun
- Advanced Materials, Vol. 23, Issue 24
High-Performance Red, Green, and Blue Electroluminescent Devices Based on Blue Emitters with Small Singlet-Triplet Splitting and Ambipolar Transport Property
journal, December 2012
- Wang, Kai; Zhao, Fangchao; Wang, Chenguang
- Advanced Functional Materials, Vol. 23, Issue 21
Host and Dopant Materials for Idealized Deep-Red Organic Electrophosphorescence Devices
journal, May 2011
- Fan, Chun-Hsiang; Sun, Peipei; Su, Tsu-Hui
- Advanced Materials, Vol. 23, Issue 26
Works referencing / citing this record:
Low-cost synthesis of heterocyclic spiro-type hole transporting materials for perovskite solar cell applications
journal, January 2018
- Govindan, Venkatesan; Yang, Kai-Cheng; Fu, Yung-Sheng
- New Journal of Chemistry, Vol. 42, Issue 9
An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp 3 )–H bond activation mediated by Selectfluor
journal, January 2019
- Gao, Yejun; Hider, Robert C.; Ma, Yongmin
- RSC Advances, Vol. 9, Issue 18