Citation: GUAN Yu-Qiao, SONG Juan, SUN Wei, ZHANG Qin, TANG Chao, LI Xue, FENG Xiao-Miao, QIAN Yan, TAO You-Tian, CHEN Shu-Fen, WANG Lian-Hui, HUANG Wei. One-Step Synthesis of Spirobi[fluorene] and Spiro[fluorene-9,9'-xanthene] Derivatives and Their Applications in Organic Light-Emitting Devices: Performance Enhancement and Related Optical Phenomena[J]. Acta Physico-Chimica Sinica, ;2016, 32(6): 1534-1542. doi: 10.3866/PKU.WHXB201603232 shu

One-Step Synthesis of Spirobi[fluorene] and Spiro[fluorene-9,9'-xanthene] Derivatives and Their Applications in Organic Light-Emitting Devices: Performance Enhancement and Related Optical Phenomena

GUAN Yu-Qiao ^1, ,
SONG Juan ¹ ,
SUN Wei ¹ ,
ZHANG Qin ¹ ,
TANG Chao ² ,
LI Xue ³ ,
FENG Xiao-Miao ¹ ,
QIAN Yan ¹ ,
TAO You-Tian ² ,
CHEN Shu-Fen ¹ ,
WANG Lian-Hui ¹ ,
HUANG Wei ²

1.
Key Laboratory for Organic Electronics and Information Displays and Institute of Advanced Materials, and Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing 210023, P. R. China;
2.
Key Laboratory of Flexible Electronics and Institute of Advanced Materials, National Synergistic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, P. R. China;
3.
Mechanical Engineering Institute, Nanjing Institute of Technology, Nanjing 211167, P. R. China

Received Date: 5 January 2016
Revised Date: 22 March 2016

Fund Project: The project was supported by the National Key Basic Research Program of China (973)(2015CB932202, 2012CB933301), National Natural Science Foundation of China (61274065, 51173081, 61136003, BZ2010043, 51372119, 51172110, 21304047, 21373114, 21003076), Innovation Team of the Ministry of Education of China (IRT1148), Ministry of Education Humanities and Social Science Research Projects, China (13YJCZH091), Natural Science Foundation of Jiangsu Province, China (BK20141424), Priority Academic Program Development of Jiangsu Provincial Higher Education Institutions, China (YX030001), Ordinary University Graduate Student Practical Innovation Projects of Jiangsu Province, China (SJLX15_0390), Pandeng Project of Nanjing University of Posts and Telecommunications, China (NY214085), and Open Foundation from Jilin University, China (IOSKL2015KF32).

Employing fluorene as substrate, we synthesized a new spirobifluorene derivative, 2'-(9-phenylfluoren-9-yl)-9,9'-spirobi[fluorene] (PF-SBF), through a one-step palladium-catalyzed cross-coupling reaction. Utilizing PF-SBF as an emitter and as a host of the blue phosphor bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyri-dyl))iridium(III)(FIrpic) in organic light-emitting devices (OLEDs), we observed a red light band different from the intrinsic blue emission of PF-SBF and FIrpic. This was attributed to the intermolecular aggregation of PF-SBF and to exciplexes generated at the interfaces of the emitting layer and the electron transport layer. The exciplex emission was then restrained through a suitable selection of hole and electron transport layer. Employing PF-SBF with di-[4-(N,N-ditolyl-amino)-phenyl]cyclohexane (TAPC) as a cohost, we obtained high-performance blue and green emissions from FIrpic and tris(2-phenylpyridine)iridium(III)(Ir(ppy)₃). The maximum current efficiencies and luminances of the blue and green OLEDs were as high as 16.7 and 50.5 cd·A^-1 and 7857 (at 11 V) and 23390 cd·m-2 (at 8 V), respectively. As an alternative to PF-SBF, we also synthesized a new xanthene derivative, 2-(9-phenyl-fluoren-9-yl)spiro[fluorene-9,9'-xanthene] (PF-SFX), with a large triplet energy level of 2.8 eV. Using PF-SFX similarly as a host of FIrpic, the current efficiency and luminance were significantly improved to 22.6 cd·A^-1 and 6421 cd·m^-2 (at 10 V). These results demonstrate the potential of PF-SBF and PF-SFX as new building blocks for high-efficiency green/blue phosphorescent host materials.
- Palladium catalysis,
- One-step method,
- Exciplex,
- Cohost,
- Blue organic light-emitting diode
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
1. [1]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
2. [2]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
3. [3]
  Huafeng SHI . Construction of MnCoNi layered double hydroxide@Co-Ni-S amorphous hollow polyhedron composite with excellent electrocatalytic oxygen evolution performance. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1380-1386. doi: 10.11862/CJIC.20240378
4. [4]
  Ruolin CHENG , Yue WANG , Xiyao NIU , Huagen LIANG , Ling LIU , Shijian LU . Efficient photothermal catalytic CO₂ cycloaddition over W₁₈O₄₉/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424
5. [5]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
6. [6]
  Jiageng Li , Putrama . 数值积分耦合非线性最小二乘法一步确定反应动力学参数. University Chemistry, 2025, 40(6): 364-370. doi: 10.12461/PKU.DXHX202407098
7. [7]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
8. [8]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
9. [9]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
10. [10]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
11. [11]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
12. [12]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
13. [13]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
14. [14]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi₄Ti₃O₁₂ Coupling with g-C₃N₄ for Photocatalytic H₂O₂ Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009
15. [15]
  Wang Wang , Yucheng Liu , Shengli Chen . Use of NiFe Layered Double Hydroxide as Electrocatalyst in Oxygen Evolution Reaction: Catalytic Mechanisms, Electrode Design, and Durability. Acta Physico-Chimica Sinica, 2024, 40(2): 2303059-0. doi: 10.3866/PKU.WHXB202303059
16. [16]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
17. [17]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
18. [18]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
19. [19]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016
20. [20]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(811)
HTML views(101)

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