Citation: Luyao Zhao, Chunbo Duan, Dongxue Ding, Shihui Liu, Debin Xia, Ying Guo, Hui Xu, Martin Baumgarten. Super rigid tris-spirobifluorenes: Syntheses and properties[J]. Chinese Chemical Letters, ;2021, 32(1): 397-400. doi: 10.1016/j.cclet.2020.02.001 shu

Super rigid tris-spirobifluorenes: Syntheses and properties

Luyao Zhao ^{a, b, 1} ,
Chunbo Duan ^{c, 1} ,
Dongxue Ding ^{c, 1} ,
Shihui Liu ^b ,
Debin Xia ^{b, *,} ,
Ying Guo ^{a, *,} ,
Hui Xu ^{c, *,} ,
Martin Baumgarten ^d

a.
College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
b.
MòT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China
c.
Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, School of Chemistry and Material Science, Heilongjiang University, Harbin 150080, China
d.
Max Planck Institute for Polymer Research, Mainz 55128, Germany

xia@hit.edu.cn

gyingxinxiang@126.com

hxu@hlju.edu.cn

Received Date: 22 December 2019
Revised Date: 13 January 2020
Accepted Date: 2 February 2020
Available Online: 5 February 2020

Figures(6)

In this work, a blue emitter with a 3D rigid structure composed of multiple spirobifluorene (3-Spiro) has been synthesized and characterized. Through a detailed study of the electrochemical and photophysical properties of 3-Spiro, we have evidenced that 3-Spiro can be applied as an active component of organic light-emitting diodes (OLEDs). The device with 5% doping rate of 4CzPNPh exhibits high external quantum efficiency (EQE) of 11%, which proves the potential of 3D rigid structure emitters for OLEDs.
- OLEDs,
- Spirobifluorene,
- Blue emitter,
- Rigid structure,
- Three dimensional
1. [1]
  S. Ohisa, T. Takahashi, M. Igarashi, et al., Adv. Funct. Mater. 29 (2019) 1808022. doi: 10.1002/adfm.201808022
2. [2]
  Q. Li, S. Bi, J. Na, et al., ACS Nano 13 (2019) 8425-8432. doi: 10.1021/acsnano.9b04163
3. [3]
  Y. Zou, S. Gong, C. Yang, et al., Adv. Optical Mater. 6 (2018) 1800568. doi: 10.1002/adom.201800568
4. [4]
  G. Zhang, Y. Li, C. Yang, et al., Adv. Mater. Interfaces (2019) 1901758.
5. [5]
  G. Zhou, B. Yao, Z. Xie, et al., Angew. Chem. Int. Ed. 46 (2007) 1149-1151. doi: 10.1002/anie.200604094
6. [6]
  J. Ding, B. Wang, Z. Yue, et al., Angew. Chem. Int. Ed. 48 (2009) 6664-6666. doi: 10.1002/anie.200902954
7. [7]
  D. Xia, B. Wang, B. Chen, et al., Angew. Chem. Int. Ed. 53 (2014) 1048-1052. doi: 10.1002/anie.201307311
8. [8]
  C. Fan, C. Duan, H. Xu, et al., Chem. Mater. 27 (2015) 5131-5140. doi: 10.1021/acs.chemmater.5b02012
9. [9]
  L. Zhao, S. Wang, S. Shao, et al., J. Mater. Chem. C 3 (2015) 8895-8903. doi: 10.1039/C5TC01711D
10. [10]
  F. Liu, H. Liu, P. Lu, et al., Nano Energy 68 (2020) 104325. doi: 10.1016/j.nanoen.2019.104325
11. [11]
  C. Hippola, D. Danilovic, J. Shinar, Adv. Opt. Mater. 8 (2020) 0191282. doi: 10.1002/adom.201901282
12. [12]
  M. Romain, D. Tondelier, B. Geffroy, et al., Chem. Eur. J. 21 (2015) 9426-9439. doi: 10.1002/chem.201500336
13. [13]
  L. Sicard, C. Quinton, J. D. Peltier, et al., Chem. Eur. J. 23 (2017) 7719-7727. doi: 10.1002/chem.201700570
14. [14]
  L. Sicard, C. Quinton, F. Lucas, et al., J. Phys. Chem. C 123 (2019) 19094-19104. doi: 10.1021/acs.jpcc.9b02507
15. [15]
  J. Oniki, T. Moriuchi, T. Amaya, et al., J. Am. Chem. Soc. 141 (2019) 18238-18245. doi: 10.1021/jacs.9b09179
16. [16]
  Y. H. Kim, D. C. Shin, S. K. Kwon, et al., Adv. Mater. 13 (2001) 1690-1693. doi: 10.1002/1521-4095(200111)13:22<1690::AID-ADMA1690>3.0.CO;2-K
17. [17]
  J. Luo, Y. Zhou, J. Pei, et al., J. Am. Chem. Soc. 129 (2007) 11314-11315. doi: 10.1021/ja073466r
18. [18]
  Y. I. Park, J. H. Son, J. W. Park, et al., Chem. Commun. 18 (2008) 2143-2145.
19. [19]
  C. Poriel, L. Sicard, J. Rault-Berthelot, Chem. Commun. 55 (2019) 14238-14254. doi: 10.1039/C9CC07169E
20. [20]
  Z. Jiang, C. Yang, Y. Liu, et al., Adv. Funct. Mater. 19 (2010) 3987-3995.
21. [21]
  C. Poriel, J. Rault-Berthelot, Acc. Chem. Res. 51 (2018) 1818-1830. doi: 10.1021/acs.accounts.8b00210
22. [22]
  Y. Li, Z. Wang, X. Li, et al., Chem. Mater. 27 (2015) 1100-1109. doi: 10.1021/cm504441v
23. [23]
  M. Romain, D. Tondelier, B. Geffroy, et al., Chem. Commun. 51 (2015) 1313-1315. doi: 10.1039/C4CC08028A
24. [24]
  D. Xia, X. Guo, K. Müllen, et al., J. Mater. Chem. A 3 (2015) 11086-11092. doi: 10.1039/C5TA00108K
25. [25]
  M. Romain, S. Thiery, C. Poriel, et al., Angew. Chem. Int. Ed. 54 (2015) 1176-1180. doi: 10.1002/anie.201409479
1. [1]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
2. [2]
  Yuhang Li , Yang Ling , Yanhang Ma . Application of three-dimensional electron diffraction in structure determination of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100237-100237. doi: 10.1016/j.cjsc.2024.100237
3. [3]
  Hui Liu , Xiangyang Tang , Zhuang Cheng , Yin Hu , Yan Yan , Yangze Xu , Zihan Su , Futong Liu , Ping Lu . Constructing multifunctional deep-blue emitters with weak charge transfer excited state for high-performance non-doped blue OLEDs and single-emissive-layer hybrid white OLEDs. Chinese Chemical Letters, 2024, 35(10): 109809-. doi: 10.1016/j.cclet.2024.109809
4. [4]
  Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu₂Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu²⁺ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698
5. [5]
  Hui Gu , Mingyue Gao , Kuan Shen , Tianli Zhang , Junhao Zhang , Xiangjun Zheng , Xingmei Guo , Yuanjun Liu , Fu Cao , Hongxing Gu , Qinghong Kong , Shenglin Xiong . F127 assisted fabrication of Ge/rGO/CNTs nanocomposites with three-dimensional network structure for efficient lithium storage. Chinese Chemical Letters, 2024, 35(9): 109273-. doi: 10.1016/j.cclet.2023.109273
6. [6]
  Chao Ma , Peng Guo , Zhongmin Liu . DNL-16: A new zeolitic layered silicate unraveled by three-dimensional electron diffraction. Chinese Journal of Structural Chemistry, 2024, 43(4): 100235-100235. doi: 10.1016/j.cjsc.2024.100235
7. [7]
  Shiyu Hou , Maolin Sun , Liming Cao , Chaoming Liang , Jiaxin Yang , Xinggui Zhou , Jinxing Ye , Ruihua Cheng . Computational fluid dynamics simulation and experimental study on mixing performance of a three-dimensional circular cyclone-type microreactor. Chinese Chemical Letters, 2024, 35(4): 108761-. doi: 10.1016/j.cclet.2023.108761
8. [8]
  Jun-Yi Wang , Jue-Yu Bao , Zheng-Guang Wu , Zheng-Yin Du , Xunwen Xiao , Xu-Feng Luo . Recent progress in steric modulation of MR-TADF materials and doping concentration independent OLEDs with narrowband emission. Chinese Journal of Structural Chemistry, 2025, 44(1): 100451-100451. doi: 10.1016/j.cjsc.2024.100451
9. [9]
  Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
10. [10]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
11. [11]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
12. [12]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
13. [13]
  Shenhao QIU , Qingquan XIAO , Huazhu TANG , Quan XIE . First-principles study on electronic structure, optical and magnetic properties of rare earth elements X (X=Sc, Y, La, Ce, Eu) doped with two-dimensional GaSe. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2250-2258. doi: 10.11862/CJIC.20240104
14. [14]
  Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
15. [15]
  Jiayu Xu , Meng Li , Baoxia Dong , Ligang Feng . Fully fluorinated hybrid zeolite imidazole/Prussian blue analogs with combined advantages for efficient oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(6): 108798-. doi: 10.1016/j.cclet.2023.108798
16. [16]
  Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
17. [17]
  Tiantian Gong , Yanan Chen , Shuo Wang , Miao Wang , Junwei Zhao . Rigid-flexible-ligand-ornamented lanthanide-incorporated selenotungstates and photoluminescence properties. Chinese Journal of Structural Chemistry, 2024, 43(9): 100370-100370. doi: 10.1016/j.cjsc.2024.100370
18. [18]
  Liwen Wang , Boyang Wang , Siyu Lu , Shubo Lv , Xiaoli Qu . High quantum yield yellow emission carbon dots for the construction of blue light blocking films. Chinese Chemical Letters, 2025, 36(2): 110497-. doi: 10.1016/j.cclet.2024.110497
19. [19]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118
20. [20]
  Xiao Yu , Dongyue Cui , Mengmeng Wang , Zhaojin Wang , Mengzhu Wang , Deshuang Tu , Vladimir Bregadze , Changsheng Lu , Qiang Zhao , Runfeng Chen , Hong Yan . Boron cluster-based TADF emitter via through-space charge transfer enabling efficient orange-red electroluminescence. Chinese Chemical Letters, 2025, 36(3): 110520-. doi: 10.1016/j.cclet.2024.110520

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1187)
HTML views(236)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142