Recent Advances in Multiple Resonance Organic/Polymer Fluorescent Materials with Narrowband Emission★
Received date: 2023-04-29
Online published: 2023-07-07
Supported by
The National Natural Science Foundation of China(52122309); The National Natural Science Foundation of China(52073282); The National Natural Science Foundation of China(51833009); The Joint Project between National Natural Science Foundation of China and Russian Science Foundation(52261135541); The CAS-Croucher Funding Scheme for Joint Laboratories, and the Start-up Scientific Research Foundation from Hainan University(KYQD(ZR)22174)
Multiple resonance (MR) emitters can be considered as intramolecular push-pull electronic systems formed by embedding electron-deficient atoms and electron-rich atoms in polycyclic aromatic skeleton. Since the structural relaxation of excited state is suppressed by the rigid molecular skeleton, multiple resonance emitters exhibit the prominent feature of narrowband emission, which enables them to attract wide attention of researchers since its report. Up to now blue, green and red multiple resonance emitters with both high device efficiency and high color purity were developed, making them become an important research direction for organic/polymeric fluorescent materials. In this review, recent advances in narrowband multiple resonance emitters are summarized from the perspective of materials and devices, with focus on B/N-, B/O(S)-, C=O/N-containing and indolocarbazole-based multiple resonance emitters. The effects of elements composition, molecular framework and substituents on their luminescent characteristics and device performances are summarized. Meanwhile, opportunities and challenges for future development of multiple resonance emitters are analyzed and prospected.
Yinuo Wang , Shiyang Shao , Lixiang Wang . Recent Advances in Multiple Resonance Organic/Polymer Fluorescent Materials with Narrowband Emission★[J]. Acta Chimica Sinica, 2023 , 81(9) : 1202 -1214 . DOI: 10.6023/A23040186
| [1] | Hong, G.; Gan, X.; Leonhardt, C.; Zhang, Z.; Seibert, J.; Busch, J. M.; Brase, S. Adv. Mater. 2021, 33, e2005630. |
| [2] | Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913. |
| [3] | Burroughes, J.; Bradley, D.; Brown, A.; Marks, R.; Mackay, K.; Friend, R.; Burns, P.; Holmes, A. Nature 1990, 347, 539. |
| [4] | Wang, Y.; Han, M.; Huang, D.; Liu, X.; Hou, L. Imaging Sci. Photochem. 2021, 39, 1. (in Chinese) |
| [4] | (王亚丽, 韩美英, 黄达, 刘贤豪, 侯丽新, 影像科学与光化学, 2021, 39, 1.) |
| [5] | Jankus, V.; Data, P.; Graves, D.; McGuinness, C.; Santos, J.; Bryce, M. R.; Dias, F. B.; Monkman, A. P. Adv. Funct. Mater. 2014, 24, 6178. |
| [6] | Baldo, M.; O'Brien, D.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M.; Forrest, S. Nature 1998, 395, 151. |
| [7] | Xiao, L.; Chen, Z.; Qu, B.; Luo, J.; Kong, S.; Gong, Q.; Kido, J. Adv. Mater. 2011, 23, 926. |
| [8] | Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234. |
| [9] | Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931. |
| [10] | Im, Y.; Kim, M.; Cho, Y. J.; Seo, J.-A.; Yook, K. S.; Lee, J. Y. Chem. Mater. 2017, 29, 1946. |
| [11] | Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444. |
| [12] | Yang, Z.; Mao, Z.; Xie, Z.; Zhang, Y.; Liu, S.; Zhao, J.; Xu, J.; Chi, Z.; Aldred, M. P. Chem. Soc. Rev. 2017, 46, 915. |
| [13] | Cai, X.; Su, S.-J. Adv. Funct. Mater. 2018, 28, 1802558. |
| [14] | Liu, Y.; Li, C.; Ren, Z.; Yan, S.; Bryce, M. R. Nat. Rev. Mater. 2018, 3, 18020. |
| [15] | Nakanotani, H.; Tsuchiya, Y.; Adachi, C. Chem. Lett. 2021, 50, 938. |
| [16] | Madayanad, S. M.; Hall, D.; Beljonne, D.; Olivier, Y.; Zysman‐Colman, E. Adv. Funct. Mater. 2020, 30, 1908677. |
| [17] | Kothavale, S. S.; Lee, J. Y. Adv. Opt. Mater. 2020, 8, 2000922. |
| [18] | Teng, J.-M.; Wang, Y.-F.; Chen, C.-F. J. Mater. Chem. C 2020, 8, 11340. |
| [19] | Ha, J. M.; Hur, S. H.; Pathak, A.; Jeong, J.-E.; Woo, H. Y. NPG Asia Mater. 2021, 13, 53. |
| [20] | Han, J.; Chen, Y.; Li, N.; Huang, Z.; Yang, C. Aggregate 2022, 3, e182. |
| [21] | Kim, H. J.; Yasuda, T. Adv. Opt. Mater. 2022, 10, 2201714. |
| [22] | Ma, P.; Han, C.; Xu, H. J. Eng. Heilongjiang Univ. 2021, 12, 63. (in Chinese) |
| [22] | (马鹏, 韩春苗, 许辉, 黑龙江大学工程学报, 2021, 12, 63.) |
| [23] | Ji, L.; Griesbeck, S.; Marder, T. B. Chem. Sci. 2017, 8, 846. |
| [24] | Grotthuss, E.; John, A.; Kaese, T.; Wagner, M. Asian J. Org. Chem. 2018, 7, 37. |
| [25] | Li, D.; Zhang, H.; Wang, Y. Chem. Soc. Rev. 2013, 42, 8416. |
| [26] | Yang, M.; Park, I. S.; Yasuda, T. J. Am. Chem. Soc. 2020, 142, 19468. |
| [27] | Hatakeyama, T.; Shiren, K.; Nakajima, K.; Nomura, S.; Nakatsuka, S.; Kinoshita, K.; Ni, J.; Ono, Y.; Ikuta, T. Adv. Mater. 2016, 28, 2777. |
| [28] | Xu, Y.; Cheng, Z.; Li, Z.; Liang, B.; Wang, J.; Wei, J.; Zhang, Z.; Wang, Y. Adv. Opt. Mater. 2020, 8, 1902142. |
| [29] | Zhang, Y.; Zhang, D.; Wei, J.; Liu, Z.; Lu, Y.; Duan, L. Angew. Chem., Int. Ed. 2019, 58, 16912. |
| [30] | Yang, M.; Shikita, S.; Min, H.; Park, I. S.; Shibata, H.; Amanokura, N.; Yasuda, T. Angew. Chem., Int. Ed. 2021, 60, 23142. |
| [31] | Matsui, K.; Oda, S.; Yoshiura, K.; Nakajima, K.; Yasuda, N.; Hatakeyama, T. J. Am. Chem. Soc. 2018, 140, 1195. |
| [32] | Oda, S.; Kumano, W.; Hama, T.; Kawasumi, R.; Yoshiura, K.; Hatakeyama, T. Angew. Chem., Int. Ed. 2021, 60, 2882. |
| [33] | Wang, Y.; Di, K.; Duan, Y.; Guo, R.; Lian, L.; Zhang, W.; Wang, L. Chem. Eng. J. 2022, 431, 133221. |
| [34] | Kondo, Y.; Yoshiura, K.; Kitera, S.; Nishi, H.; Oda, S.; Gotoh, H.; Sasada, Y.; Yanai, M.; Hatakeyama, T. Nat. Photonics 2019, 13, 678. |
| [35] | Park, J.; Lim, J.; Lee, J. H.; Jang, B.; Han, J. H.; Yoon, S. S.; Lee, J. Y. ACS Appl. Mater. Interfaces 2021, 13, 45798. |
| [36] | Nagata, M.; Min, H.; Watanabe, E.; Fukumoto, H.; Mizuhata, Y.; Tokitoh, N.; Agou, T.; Yasuda, T. Angew. Chem., Int. Ed. 2021, 60, 20280. |
| [37] | Hua, T.; Miao, J.; Xia, H.; Huang, Z.; Cao, X.; Li, N.; Yang, C. Adv. Funct. Mater. 2022, 32, 2201032. |
| [38] | Li, Q.; Wu, Y.; Wang, X.; Yang, Q.; Hu, J.; Zhong, R.; Shao, S.; Wang, L. Chem. Eur. J. 2022, 28, e202104214. |
| [39] | Park, I. S.; Min, H.; Yasuda, T. Angew. Chem., Int. Ed. 2022, 61, e202205684. |
| [40] | Li, Q.; Wu, Y.; Yang, Q.; Wang, S.; Shao, S.; Wang, L. ACS Appl. Mater. Interfaces 2022, 14, 49995. |
| [41] | Xu, Y.; Li, C.; Li, Z.; Wang, J.; Xue, J.; Wang, Q.; Cai, X.; Wang, Y. CCS Chem. 2022, 4, 2065. |
| [42] | Xu, Y.; Li, C.; Li, Z.; Wang, Q.; Cai, X.; Wei, J.; Wang, Y. Angew. Chem., Int. Ed. 2020, 59, 17442. |
| [43] | Zhang, Y.; Zhang, D.; Wei, J.; Hong, X.; Lu, Y.; Hu, D.; Li, G.; Liu, Z.; Chen, Y.; Duan, L. Angew. Chem., Int. Ed. 2020, 59, 17499. |
| [44] | Zhang, Y.; Li, G.; Wang, L.; Huang, T.; Wei, J.; Meng, G.; Wang, X.; Zeng, X.; Zhang, D.; Duan, L. Angew. Chem., Int. Ed. 2022, 61, e202202380. |
| [45] | Xu, Y.; Wang, Q.; Wei, J.; Peng, X.; Xue, J.; Wang, Z.; Su, S. J.; Wang, Y. Angew. Chem., Int. Ed. 2022, 61, e202204652. |
| [46] | Jiang, P.; Zhan, L.; Cao, X.; Lv, X.; Gong, S.; Chen, Z.; Zhou, C.; Huang, Z.; Ni, F.; Zou, Y.; Yang, C. Adv. Opt. Mater. 2021, 9, 2100825. |
| [47] | Uemura, S.; Oda, S.; Hayakawa, M.; Kawasumi, R.; Ikeda, N.; Lee, Y.-T.; Chan, C.-Y.; Tsuchiya, Y.; Adachi, C.; Hatakeyama, T. J. Am. Chem. Soc. 2022, 145, 1505. |
| [48] | Ikeda, N.; Oda, S.; Matsumoto, R.; Yoshioka, M.; Fukushima, D.; Yoshiura, K.; Yasuda, N.; Hatakeyama, T. Adv. Mater. 2020, 32, e2004072. |
| [49] | Cai, X.; Xue, J.; Li, C.; Liang, B.; Ying, A.; Tan, Y.; Gong, S.; Wang, Y. Angew. Chem., Int. Ed. 2022, 61, e202200337. |
| [50] | Liu, F.; Cheng, Z.; Jiang, Y.; Gao, L.; Liu, H.; Liu, H.; Feng, Z.; Lu, P.; Yang, W. Angew. Chem., Int. Ed. 2022, 61, e202116927. |
| [51] | Cao, X.; Pan, K.; Miao, J.; Lv, X.; Huang, Z.; Ni, F.; Yin, X.; Wei, Y.; Yang, C. J. Am. Chem. Soc. 2022, 144, 22976. |
| [52] | Meng, G.; Dai, H.; Huang, T.; Wei, J.; Zhou, J.; Li, X.; Wang, X.; Hong, X.; Yin, C.; Zeng, X.; Zhang, Y.; Yang, D.; Ma, D.; Li, G.; Zhang, D.; Duan, L. Angew. Chem., Int. Ed. 2022, 61, e202207293. |
| [53] | Qi, Y.; Ning, W.; Zou, Y.; Cao, X.; Gong, S.; Yang, C. Adv. Funct. Mater. 2021, 31, 2102017. |
| [54] | Luo, X. F.; Ni, H. X.; Lv, A. Q.; Yao, X. K.; Ma, H. L.; Zheng, Y. X. Adv. Opt. Mater. 2022, 10, 2200504. |
| [55] | Liu, Y.; Xiao, X.; Ran, Y.; Bin, Z.; You, J. Chem. Sci. 2021, 12, 9408. |
| [56] | Zhang, Y.; Wei, J.; Wang, L.; Huang, T.; Meng, G.; Wang, X.; Zeng, X.; Du, M.; Fan, T.; Yin, C.; Zhang, D.; Duan, L. Adv. Mater. 2023, 35, e2209396. |
| [57] | Zhang, Y.; Zhang, D.; Huang, T.; Gillett, A. J.; Liu, Y.; Hu, D.; Cui, L.; Bin, Z.; Li, G.; Wei, J.; Duan, L. Angew. Chem., Int. Ed. 2021, 60, 20498. |
| [58] | Wang, Y.; Zhang, K.; Chen, F.; Wang, X.; Yang, Q.; Wang, S.; Shao, S.; Wang, L. Chin. J. Chem. 2022, 40, 2671. |
| [59] | Zou, Y.; Hu, J.; Yu, M.; Miao, J.; Xie, Z.; Qiu, Y.; Cao, X.; Yang, C. Adv. Mater. 2022, 34, e2201442. |
| [60] | Hirai, H.; Nakajima, K.; Nakatsuka, S.; Shiren, K.; Ni, J.; Nomura, S.; Ikuta, T.; Hatakeyama, T. Angew. Chem., Int. Ed. 2015, 54, 13581. |
| [61] | Kitamoto, Y.; Suzuki, K.; Miyata, Y.; Kita, H.; Funaki, K.; Oi, S. Chem. Commun. 2016, 52, 7098. |
| [62] | Chen, F.; Zhao, L.; Wang, X.; Yang, Q.; Li, W.; Tian, H.; Shao, S.; Wang, L.; Jing, X.; Wang, F. Sci. China: Chem. 2021, 64, 547. |
| [63] | Chang, Y.; Wu, Y.; Wang, X.; Li, W.; Yang, Q.; Wang, S.; Shao, S.; Wang, L. Chem. Eng. J. 2023, 451, 138545. |
| [64] | Yuan, Y.; Tang, X.; Du, X. Y.; Hu, Y.; Yu, Y. J.; Jiang, Z. Q.; Liao, L. S.; Lee, S. T. Adv. Opt. Mater. 2019, 7, 1801536. |
| [65] | Zou, S. N.; Peng, C. C.; Yang, S. Y.; Qu, Y. K.; Yu, Y. J.; Chen, X.; Jiang, Z. Q.; Liao, L. S. Org. Lett. 2021, 23, 958. |
| [66] | Huang, F.; Wang, K.; Shi, Y. Z.; Fan, X. C.; Zhang, X.; Yu, J.; Lee, C. S.; Zhang, X. H. ACS Appl. Mater. Interfaces 2021, 13, 36089. |
| [67] | Sun, D.; Suresh, S. M.; Hall, D.; Zhang, M.; Si, C.; Cordes, D. B.; Slawin, A. M. Z.; Olivier, Y.; Zhang, X.; Zysman-Colman, E. Mater. Chem. Front. 2020, 4, 2018. |
| [68] | Min, H.; Park, I. S.; Yasuda, T. Angew. Chem., Int. Ed. 2021, 60, 7643. |
| [69] | Wu, S.; Kumar Gupta, A.; Yoshida, K.; Gong, J.; Hall, D.; Cordes, D. B.; Slawin, A. M. Z.; Samuel, I. D. W.; Zysman-Colman, E. Angew. Chem., Int. Ed. 2022, 61, e202213697. |
| [70] | Fan, X. C.; Wang, K.; Shi, Y. Z.; Chen, J. X.; Huang, F.; Wang, H.; Hu, Y. N.; Tsuchiya, Y.; Ou, X. M.; Yu, J.; Adachi, C.; Zhang, X. H. Adv. Opt. Mater. 2022, 10, 2101789. |
| [71] | Lee, H. L.; Chung, W. J.; Lee, J. Y. Small 2020, 16, e1907569. |
| [72] | Patil, V. V.; Lee, H. L.; Kim, I.; Lee, K. H.; Chung, W. J.; Kim, J.; Park, S.; Choi, H.; Son, W. J.; Jeon, S. O.; Lee, J. Y. Adv. Sci. 2021, 8, 2101137. |
| [73] | Lee, H.; Jeon, S.; Kim, I.; Kim, S.; Lim, J.; Kim, J.; Park, S.; Chwae, J.; Son, W.; Choi, H.; Lee, J. Adv. Mater. 2022, 34, 2202464. |
| [74] | Zeng, X.; Wang, X.; Zhang, Y.; Meng, G.; Wei, J.; Liu, Z.; Jia, X.; Li, G.; Duan, L.; Zhang, D. Angew. Chem., Int. Ed. 2022, 61, 202117181. |
| [75] | Lee, S. Y.; Yasuda, T.; Komiyama, H.; Lee, J.; Adachi, C. Adv. Mater. 2016, 28, 4019. |
| [76] | Ren, Z.; Nobuyasu, R. S.; Dias, F. B.; Monkman, A. P.; Yan, S.; Bryce, M. R. Macromolecules 2016, 49, 5452. |
| [77] | Xie, G.; Luo, J.; Huang, M.; Chen, T.; Wu, K.; Gong, S.; Yang, C. Adv. Mater. 2017, 29, 1604223. |
| [78] | Wang, T.; Zou, Y.; Huang, Z.; Li, N.; Miao, J.; Yang, C. Angew. Chem., Int. Ed. 2022, 61, 202211172. |
| [79] | Hu, Y.; Miao, J.; Zhong, C.; Zeng, Y.; Gong, S.; Cao, X.; Zhou, X.; Gu, Y.; Yang, C. Angew. Chem., Int. Ed. 2023, 62, e202302478. |
| [80] | Liu, T.; Cheng, C.; Lou, W.; Deng, C.; Liu, J.; Wang, D.; Tsuboi, T.; Zhang, Q. J. Mater. Chem. C 2022, 10, 7799. |
/
| 〈 |
|
〉 |
