Citation: Zhaoyue Lü, Tiantian Chai, Yichao Jin, Xiao Wang, Ye Zou, Lijiang Zhang, Jiankang Feng, Mengtong Zhang, Shuo Wang, Chichong Lu, Guofan Jin. Asymmetrical carbazole-benzonitrile-based TADF emitters designed by alternate donor-acceptor strategy[J]. Chinese Chemical Letters, ;2025, 36(6): 110817. doi: 10.1016/j.cclet.2025.110817 shu

Asymmetrical carbazole-benzonitrile-based TADF emitters designed by alternate donor-acceptor strategy

Zhaoyue Lü ^{b, 1} ,
Tiantian Chai ^{a, 1} ,
Yichao Jin ^b ,
Xiao Wang ^b ,
Ye Zou ^{c, *,} ,
Lijiang Zhang ^b ,
Jiankang Feng ^a ,
Mengtong Zhang ^a ,
Shuo Wang ^a ,
Chichong Lu ^{d, *,} ,
Guofan Jin ^{a, *,}

a.
School of Pharmacy, Jiangsu University, Zhenjiang 212013, China
b.
School of Physics, East China University of Science and Technology, Shanghai 200237, China
c.
Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
d.
Department of Chemistry, College of Light Industry Science and Engineering, Beijing Technology and Business University, Beijing 100048, China

zouye@iccas.ac.cn

luchichong@btbu.edu.cn

organicboron@ujs.edu.cn

Received Date: 18 September 2024
Revised Date: 27 December 2024
Accepted Date: 2 January 2025
Available Online: 2 January 2025

Figures(5)

A pair of asymmetric rigid carbazole-benzonitrile-based emitters were synthesized by strategically alternating donor and acceptor groups along the molecular edges. The spin-flip process is accelerated by both the formation of localized and delocalized charge transfer states due to linearly positioned donors and strong spin-orbital coupling between different excitation feature of the lowest singlet and triplet excited states. This molecular architecture results in a remarkable short delayed lifespan of around 100 ns. The application of the two emitters in organic light-emitting diodes (OLEDs) achieves the highest external quantum efficiencies of 13.0% for the green emitter and 9.1% for the sky-blue emitter. Impressively, these devices maintain their high efficiency even at high luminance levels. The sustained efficiency is ascribed to the effective suppression of exciton quenching by substantially shortening delayed lifespan. These findings underscore the practical utility of the molecular design strategy that incorporates alternate donor and acceptor groups at the molecular periphery for shortening delayed fluorescence lifetime, and hold great promise for the development of high-performance OLEDs.
- Delayed fluorescence,
- Linear D-A-D structure,
- Localized excited state,
- Delocalized charge transfer state,
- Spin-orbital coupling
1. [1]
  Y. Lee, H. Cho, H. Yoon, et al., Adv. Mater. Technol. 8 (2023) 2201067. doi: 10.1002/admt.202201067
2. [2]
  G. Hong, X. Gan, C. Leonhardt, et al., Adv. Mater. 33 (2021) 2005630. doi: 10.1002/adma.202005630
3. [3]
  C.M. Kang, H. Lee, J. Inf. Disp. 23 (2022) 19–32. doi: 10.1080/15980316.2021.1917461
4. [4]
  W.J. Joo, J. Kyoung, M. Esfandyarpour, et al., Science 370 (2020) 459–463. doi: 10.1126/science.abc8530
5. [5]
  Y. Lee, J.W. Chung, G.H. Lee, et al., Sci. Adv. 7 (2021) eabg9180. doi: 10.1126/sciadv.abg9180
6. [6]
  H. Chae, Y. Park, Y. Jo, et al., Adv. Mater. Interfaces 10 (2023) 2202443. doi: 10.1002/admi.202202443
7. [7]
  X. Hu, Y. Qin, Z. Li, et al., Chin. Chem. Lett. 33 (2022) 4645–4648. doi: 10.1016/j.cclet.2021.12.047
8. [8]
  X.C. Fan, K. Wang, Y.Z. Shi, et al., SmartMat 4 (2023) e1122. doi: 10.1002/smm2.1122
9. [9]
  S. Hirata, Y. Sakai, K. Masui, et al., Nat. Mater. 14 (2015) 330–336. doi: 10.1038/nmat4154
10. [10]
  Y. Mei, D. Liu, J. Li, H. Li, W. Wei, J. Mater. Chem. C 9 (2021) 5885–5892. doi: 10.1039/d1tc00592h
11. [11]
  H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 492 (2012) 234–238. doi: 10.1038/nature11687
12. [12]
  Y. Im, M. Kim, Y.J. Cho, et al., Chem. Mater. 29 (2017) 1946–1963. doi: 10.1021/acs.chemmater.6b05324
13. [13]
  F. Fang, L. Zhu, M. Li, et al., Adv. Sci. 8 (2021) 2102970. doi: 10.1002/advs.202102970
14. [14]
  Y. Mei, D. Liu, J. Li, J. Wang, J. Mater. Chem. C 10 (2022) 16524–16535. doi: 10.1039/d2tc03448d
15. [15]
  X. Dong, S. Shen, Y. Qin, et al., Chin. Chem. Lett. 34 (2023) 108311. doi: 10.1016/j.cclet.2023.108311
16. [16]
  J. Liu, Z. Feng, C. Peng, et al., Chin. Chem. Lett. 34 (2023) 107634. doi: 10.1016/j.cclet.2022.06.057
17. [17]
  L. Yan, N. Su, Y. Yang, et al., SmartMat 5 (2024) e1272. doi: 10.1002/smm2.1272
18. [18]
  M. Mamada, H. Katagiri, C.Y. Chan, et al., Adv. Funct. Mater. 32 (2022) 2204352. doi: 10.1002/adfm.202204352
19. [19]
  J. Kim, C.W. Joo, S.J. Woo, et al., J. Mater. Chem. C 10 (2022) 7304–7310. doi: 10.1039/d2tc00669c
20. [20]
  D. Zhang, M. Cai, Y. Zhang, D. Zhang, L. Duan, Mater. Horiz. 3 (2016) 145–151. doi: 10.1039/C5MH00258C
21. [21]
  H. Noda, H. Nakanotani, C. Adachi, Sci. Adv. 4 (2018) eaao6910. doi: 10.1126/sciadv.aao6910
22. [22]
  C.Y. Chan, M. Tanaka, H. Nakanotani, C. Adachi, Nat. Commun. 9 (2018) 5036. doi: 10.1038/s41467-018-07482-6
23. [23]
  S. Zou, F. Xie, M. Xie, et al., Adv. Sci. 7 (2020) 1902508. doi: 10.1002/advs.201902508
24. [24]
  F.M. Xie, Z.D. An, M. Xie, et al., J. Mater. Chem. C 8 (2020) 5769–5776. doi: 10.1039/d0tc00718h
25. [25]
  C. Chan, M. Tanaka, Y. Lee, et al., Nat. Photonics 15 (2021) 203–207. doi: 10.1038/s41566-020-00745-z
26. [26]
  C. Murawski, K. Leo, M.C. Gather, Adv. Mater. 25 (2013) 6801–6827. doi: 10.1002/adma.201301603
27. [27]
  M. Hasan, A. Shukla, V. Ahmad, et al., Adv. Funct. Mater. 30 (2020) 2000580. doi: 10.1002/adfm.202000580
28. [28]
  B. Zee, Y. Li, G.J.A.H. Wetzelaer, P.W.M. Blom, Adv. Opt. Mater. 9 (2021) 2100249. doi: 10.1002/adom.202100249
29. [29]
  Y. Liu, C. Li, Z. Ren, S. Yan, M.R. Bryce, Nat. Rev. Mater. 3 (2018) 18020. doi: 10.1038/natrevmats.2018.20
30. [30]
  T. Hosokai, H. Matsuzaki, H. Nakanotani, et al., Sci. Adv. 3 (2017) e1603282. doi: 10.1126/sciadv.1603282
31. [31]
  X. Dai, L. Liu, Z. Ji, Q. Meng, Y. Zou, Chin. Chem. Lett. 34 (2023) 107239. doi: 10.1016/j.cclet.2022.02.044
32. [32]
  Y. Zou, Q. Meng, H. Mao, D. Zhu, Org. Electron. 41 (2017) 307–314. doi: 10.1016/j.orgel.2016.11.021
33. [33]
  J. Chen, Y. Xiao, K. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 2478–2484. doi: 10.1002/anie.202012070
34. [34]
  W. Li, M. Li, W. Li, et al., ACS Appl. Mater. Interfaces 13 (2021) 5302–5311. doi: 10.1021/acsami.0c19302
35. [35]
  L. Gan, Z. Xu, Z. Wang, et al., Adv. Funct. Mater. 29 (2019) 1808088. doi: 10.1002/adfm.201808088
36. [36]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 16 Revision A.03, Gaussian Inc., Wallingford, CT, 2016.
37. [37]
  R.L. Martin, J. Chem. Phys. 118 (2003) 4775–4777. doi: 10.1063/1.1558471
38. [38]
  Y. Liu, P. Ganesan, M. Chen, et al., Chem. Eng. J. 499 (2024) 156529. doi: 10.1016/j.cej.2024.156529
39. [39]
  J.U. Kim, I.S. Park, C.Y. Chan, et al., Nat. Commun. 11 (2020) 1765. doi: 10.1038/s41467-020-15558-5
1. [1]
  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
2. [2]
  Haiyan Yin , Abdusalam Ablez , Zhuangzhuang Wang , Weian Li , Yanqi Wang , Qianqian Hu , Xiaoying Huang . Novel open-framework chalcogenide photocatalysts: Cobalt cocatalyst valence state modulating critical charge transfer pathways towards high-efficiency hydrogen evolution. Chinese Journal of Structural Chemistry, 2025, 44(4): 100560-100560. doi: 10.1016/j.cjsc.2025.100560
3. [3]
  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
4. [4]
  Hui Zhang , Rong Feng , Wanyi Yu , Hongbei Wei , Tianhong Wu , Peng Zhang , Wenhai Bian , Xin Li , Di Gao , Guojun Weng , Zhe Yang , Tony D. James , Xiaolong Sun . Evaluating the global thiols redox state in living cells using a reducing sulfur species responsive fluorescence switching platform. Chinese Chemical Letters, 2025, 36(4): 110528-. doi: 10.1016/j.cclet.2024.110528
5. [5]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
6. [6]
  Hengying Xiang , Nanping Deng , Lu Gao , Wen Yu , Bowen Cheng , Weimin Kang . 3D core-shell nanofibers framework and functional ceramic nanoparticles synergistically reinforced composite polymer electrolytes for high-performance all-solid-state lithium metal battery. Chinese Chemical Letters, 2024, 35(8): 109182-. doi: 10.1016/j.cclet.2023.109182
7. [7]
  Bin Chen , Chaoyang Zheng , Dehuan Shi , Yi Huang , Renxia Deng , Yang Wei , Zheyuan Liu , Yan Yu , Shenghong Zhong . p-d orbital hybridization induced by CuGa2 promotes selective N2 electroreduction. Chinese Journal of Structural Chemistry, 2025, 44(1): 100468-100468. doi: 10.1016/j.cjsc.2024.100468
8. [8]
  Jingyu Shi , Xiaofeng Wu , Yutong Chen , Yi Zhang , Xiangyan Hou , Ruike Lv , Junwei Liu , Mengpei Jiang , Keke Huang , Shouhua Feng . Structure factors dictate the ionic conductivity and chemical stability for cubic garnet-based solid-state electrolyte. Chinese Chemical Letters, 2025, 36(5): 109938-. doi: 10.1016/j.cclet.2024.109938
9. [9]
  Kaili Wang , Pengcheng Liu , Mingzhe Wang , Tianran Wei , Jitao Lu , Xingling Zhao , Zaiyong Jiang , Zhimin Yuan , Xijun Liu , Jia He . Modulating d-d orbitals coupling in PtPdCu medium-entropy alloy aerogels to boost pH-general methanol electrooxidation performance. Chinese Chemical Letters, 2025, 36(4): 110532-. doi: 10.1016/j.cclet.2024.110532
10. [10]
  Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
11. [11]
  Biao Fang , Runwei Mo . PVDF-based solid-state battery. Chinese Journal of Structural Chemistry, 2024, 43(8): 100347-100347. doi: 10.1016/j.cjsc.2024.100347
12. [12]
  Jiayuan Liang , Xin Mi , Songhao Guo , Hui Luo , Kejun Bu , Tonghuan Fu , Menglin Duan , Yang Wang , Qingyang Hu , Rengen Xiong , Peng Qin , Fuqiang Huang , Xujie Lü . Pressure-induced emission in 0D metal halide (EATMP)SbBr5 by regulating exciton-phonon coupling. Chinese Journal of Structural Chemistry, 2024, 43(7): 100333-100333. doi: 10.1016/j.cjsc.2024.100333
13. [13]
  Jing Guo . Stacking solid-state electrolyte and aluminum pellets for anode-free solid-state batteries. Chinese Chemical Letters, 2025, 36(5): 110764-. doi: 10.1016/j.cclet.2024.110764
14. [14]
  Changyuan Bao , Yunpeng Jiang , Haoyin Zhong , Huaizheng Ren , Junhui Wang , Binbin Liu , Qi Zhao , Fan Jin , Yan Meng Chong , Jianguo Sun , Fei Wang , Bo Wang , Ximeng Liu , Dianlong Wang , John Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353
15. [15]
  Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
16. [16]
  Yuqing Zhu , Haohao Chen , Li Wang , Liqun Ye , Houle Zhou , Qintian Peng , Huaiyong Zhu , Yingping Huang . Piezoelectric materials for pollutants degradation: State-of-the-art accomplishments and prospects. Chinese Chemical Letters, 2024, 35(4): 108884-. doi: 10.1016/j.cclet.2023.108884
17. [17]
  Tianyi Hou , Yunhui Huang , Henghui Xu . Interfacial engineering for advanced solid-state Li-metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100313-100313. doi: 10.1016/j.cjsc.2024.100313
18. [18]
  Huangjie Lu , Yingzhe Du , Peng Lin , Jian Lin . Separation of americium from lanthanides based on oxidation state control. Chinese Journal of Structural Chemistry, 2024, 43(10): 100344-100344. doi: 10.1016/j.cjsc.2024.100344
19. [19]
  Qiao Wang , Ziling Jiang , Chuang Yu , Liping Li , Guangshe Li . Research progress of inorganic sodium ion conductors for solid-state batteries. Chinese Chemical Letters, 2025, 36(6): 110006-. doi: 10.1016/j.cclet.2024.110006
20. [20]
  Mufan Cao , Long Pan , Yaping Wang , Xianwei Sui , Xiong Xiong Liu , Shengfa Feng , Pengcheng Yuan , Min Gao , Jiacheng Liu , Song-Zhu Kure-Chu , Takehiko Hihara , Yang Zhou , Zheng-Ming Sun . Mechanical-durable and humidity-resistant dry-processed halide solid-state electrolyte films for all-solid-state battery. Chinese Chemical Letters, 2025, 36(6): 110391-. doi: 10.1016/j.cclet.2024.110391

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(163)
HTML views(4)

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