3D interlocking triggers intramolecular interactions to achieve an efficient deep-blue multiple resonance thermal activation delayed fluorescence material

Abstract

Multi-resonance thermally activated delayed fluorescence (MR-TADF) emitters have shown promise for achieving full-color emission with a high efficiency and a narrow band. However, the development of MR-TADF materials with both high efficiency and deep-blue emission for organic light-emitting diode (OLED) remains a significant challenge. Herein, a B/N-based MR core and a indolocarbazole group are interlocked in 3D mode to induce intramolecular interaction between both, culminating in the development of the target emitter, DPABN-ICz. Notably, DPABN-ICz demonstrates a remarkable deep-blue emission, peaking at 445 nm, with a small full width at half maximum (FWHM) of 19 nm and a Commission Internationale de L'Eclairage (CIE)y coordinate of 0.06. Interestingly, DPABN-ICz exhibits an enhanced oscillator strength of 0.2975, resulting in an impressive photoluminescence quantum yield of 94%. Furthermore, the sensitized OLED achieves a high maximum external quantum efficiency of 31.4%, and a narrow electroluminescence with a small FWHM of 27 nm and the CIE coordinates of (0.153, 0.055), closely aligning with the BT.2020 deep-blue emission standard.

Keywords

deep-blue electroluminescence / intramolecular interaction / multiple-resonance / spatial assembly / thermally activated delayed fluorescence

References

[1] J. E. Ryu, S. Park, Y. Park, S. W. Ryu, K. Hwang, H. W. Jang, Adv. Mater. 2023, 35, e2204947.

[2] S. H. Ko, J. Rogers, Adv. Funct. Mater. 2021, 31, 2106546.

[3] D. Zhang, T. Huang, L. Duan, R. Shi, W. Huang, Z. Shi, L. Wu, F. Zhang, L. Gao, C. Li, X. Zhang, J. Xu, H. Zhang, Adv. Mater. 2020, 32, e1902391.

[4] H. Fang, J. Guo, H. Wu, Nano Energy 2022, 96, 107112.

[5] X. Tang, Q. Bai, Q. Peng, Y. Gao, J. Li, Y. Liu, L. Yao, P. Lu, B. Yang, Y. Ma, Chem. Mater. 2015, 27, 7050.

[6] X. Yang, X. Xu, G. Zhou, J. Mater. Chem. C 2015, 3, 913.

[7] D. Yu, F. Zhao, Z. Zhang, C. Han, H. Xu, J. Li, D. Ma, P. Yan, Chem. Commun. 2012, 48, 6157.

[8] B. Minaev, G. Baryshnikov, H. Agren, Phys. Chem. Chem. Phys. 2014, 16, 1719.

[9] T. Fleetham, G. Li, J. Li, Adv. Mater. 2017, 29, 1601861.

[10] M. Li, Z. Chen, K. Liu, Q. He, S.-J. Su, FlexMat 2025, 2, 145.

[11] H. Li, C. Chen, Z. Ye, K. Feng, J. Huang, G. Xie, Y. Tao, FlexMat 2024, 1, 173.

[12] X. Jiao, Y. Wang, R. Zhu, Y. Chen, J. Pan, Z. Lu, X.-C. Hang, Z.  Sun, W. Huang, FlexMat 2025, 2, 442.

[13] W.-L. Tsai, M.-H. Huang, W.-K. Lee, Y.-J. Hsu, K.-C. Pan, Y.-H. Huang, H.-C. Ting, M. Sarma, Y.-Y. Ho, H.-C. Hu, C.-C. Chen, M.-T. Lee, K.-T. Wong, C.-C. Wu, Chem. Commun. 2015, 51, 13662.

[14] D. Poitras, C.-C. Kuo, C. Py, Opt. Exp. 2008, 16, 11.

[15] T.-Y. Cho, C.-L. Lin, C.-C. Wu, Appl. Phys. Lett. 2006, 88, 111106.

[16] H. Yokoyama, Science 1992, 256, 66.

[17] K. Matsui, S. Oda, K. Yoshiura, K. Nakajima, N. Yasuda, T. Hatakeyama, J. Am. Chem. Soc. 2018, 140, 1195.

[18] X.-F. Luo, S.-Q. Song, X. Wu, C.-F. Yip, S. Cai, Y.-X. Zheng, Aggregate 2024, 5, e445.

[19] Y. Zhang, D. Zhang, J. Wei, Z. Liu, Y. Lu, L. Duan, Angew. Chem., Int. Ed. 2019, 58, 16912.

[20] S. Oda, W. Kumano, T. Hama, R. Kawasumi, K. Yoshiura, T. Hatakeyama, Angew. Chem., Int. Ed. 2021, 60, 2882.

[21] H. Tanaka, S. Oda, G. Ricci, H. Gotoh, K. Tabata, R. Kawasumi, D. Beljonne, Y. Olivier, T. Hatakeyama, Angew. Chem., Int. Ed. 2021, 60, 17910.

[22] Y. Zhang, D. Zhang, J. Wei, X. Hong, Y. Lu, D. Hu, G. Li, Z. Liu, Y. Chen, L. Duan, Angew. Chem., Int. Ed. 2020, 59, 17499.

[23] M. Yang, S. Shikita, H. Min, I. S. Park, H. Shibata, N. Amanokura, T. Yasuda, Angew. Chem., Int. Ed. 2021, 60, 23142.

[24] X.-F. Luo, H.-X. Ni, H.-L. Ma, Z.-Z. Qu, J. Wang, Y.-X. Zheng, J.-L. Zuo, Adv. Opt. Mater. 2022, 10, 2102513.

[25] Y. Xu, Z. Cheng, Z. Li, B. Liang, J. Wang, J. Wei, Z. Zhang, Y. Wang, Adv. Opt. Mater. 2020, 8, 1902142.

[26] N. Ikeda, S. Oda, R. Matsumoto, M. Yoshioka, D. Fukushima, K. Yoshiura, N. Yasuda, T. Hatakeyama, Adv. Mater. 2020, 32, 2004072.

[27] Y. Xu, Q. Wang, X. Cai, C. Li, Y. Wang, J. Bao, Q. Su, Z. Xu, C. Wang, Z. Wang, D. Shan, B. Guo, Adv. Mater. 2021, 33, 2100652.

[28] P. Jiang, L. Zhan, X. Cao, X. Lv, S. Gong, Z. Chen, C. Zhou, Z. Huang, F. Ni, Y. Zou, C. Yang, Adv. Opt. Mater. 2021, 9, 2100825.

[29] Y. Qi, W. Ning, Y. Zou, X. Cao, S. Gong, C. Yang, Adv. Funct. Mater. 2021, 31, 2102017.

[30] X. Wu, J.-W. Huang, B.-K. Su, S. Wang, L. Yuan, W.-Q. Zheng, H. Zhang, Y.-X. Zheng, W. Zhu, P.-T. Chou, Adv. Mater. 2022, 34, 2105080.

[31] X.-F. Luo, S.-Q. Song, H.-X. Ni, H. Ma, D. Yang, D. Ma, Y.-X. Zheng, J.-L. Zuo, Angew. Chem., Int. Ed. 2022, 61, e202209984.

[32] Y. Zhang, G. Li, L. Wang, T. Huang, J. Wei, G. Meng, X. Wang, X. Zeng, D. Zhang, L. Duan, Angew. Chem., Int. Ed. 2022, 61, e202202380.

[33] M. Yang, I. S. Park, T. Yasuda, J. Am. Chem. Soc. 2020, 142, 19468.

[34] J.-K. Li, X.-Y. Chen, Y.-L. Guo, X.-C. Wang, A. C. H. Sue, X.-Y. Cao, X.-Y. Wang, J. Am. Chem. Soc. 2021, 143, 17958.

[35] Y. Zhang, D. Zhang, T. Huang, A. J. Gillett, Y. Liu, D. Hu, L. Cui, Z. Bin, G. Li, J. Wei, L. Duan, Angew. Chem., Int. Ed. 2021, 60, 20498.

[36] Y. Liu, X. Xiao, Y. Ran, Z. Bin, J. You, Chem. Sci. 2021, 12, 9408.

[37] M. Du, Y. Chen, M. Mai, T. Fan, Q. Jin, Y. Zhang, L. Duan, FlexMat 2024, 1, 46.

[38] T. Hua, L. Zhan, N. Li, Z. Huang, X. Cao, Z. Xiao, S. Gong, C. Zhou, C. Zhong, C. Yang, Chem. Eng. J. 2021, 426, 131169.

[39] P. Lu, F. Liu, Z. Cheng, Y. Jiang, L. Gao, H. Liu, H. Liu, Z. Feng, W. Yang, Angew. Chem., Int. Ed. 2022, 61, e202116927.

[40] Y. Kondo, K. Yoshiura, S. Kitera, H. Nishi, S. Oda, H. Gotoh, Y. Sasada, M. Yanai, T. Hatakeyama, Nat. Photonics 2019, 13, 678.

[41] I. S. Park, M. Yang, H. Shibata, N. Amanokura, T. Yasuda, Adv. Mater. 2022, 34, 2107951.

[42] M. Mamada, A. Aoyama, R. Uchida, J. Ochi, S. Oda, Y. Kondo, M. Kondo, T. Hatakeyama, Adv. Mater. 2024, 36, 2402905.

[43] L. Wu, X. Mu, D. Liu, W. Li, D. Li, J. Zhang, C. Liu, T. Feng, Y. Wu, J. Li, S.-J. Su, Z. Ge, Angew. Chem., Int. Ed. 2024, 63, e202409580.

[44] M. Xing, G. Chen, S. Wang, X. Yin, J. Liu, Z. Xue, N. Li, J. Miao, Z. Huang, C. Yang, Adv. Funct. Mater. 2025, 35, 2414635.

[45] S. M. Suresh, L. Zhang, T. Matulaitis, D. Hall, C. Si, G. Ricci, A. M. Z. Slawin, S. Warriner, D. Beljonne, Y. Olivier, I. D. W. Samuel, E. Zysman-Colman, Adv. Mater. 2023, 35, 2300997.

[46] K. R. Naveen, H. Lee, R. Braveenth, K. J. Yang, S. J. Hwang, J. H. Kwon, Chem. Eng. J. 2022, 432, 134381.

[47] D. Zhang, X. Song, A. J. Gillett, B. H. Drummond, S. T. E. Jones, G. Li, H. He, M. Cai, D. Credgington, L. Duan, Adv. Mater. 2020, 32, 1908355.

[48] X. Huang, J. Liu, Y. Xu, G. Chen, M. Huang, M. Yu, X. Lv, X. Yin, Y. Zou, J. Miao, X. Cao, C. Yang, Natl. Sci. Rev. 2024, 11, nwae115.

[49] M. Nagata, H. Min, E. Watanabe, H. Fukumoto, Y. Mizuhata, N. Tokitoh, T. Agou, T. Yasuda, Angew. Chem., Int. Ed. 2021, 60, 20280.

[50] N. Aizawa, A. Matsumoto, T. Yasuda, Sci. Adv. 2021, 7, eabe5769.

[51] X. Xiong, J. Li, T. Chen, X. Fan, Y. Cheng, H. Wang, F. Huang, H. Wu, J. Yu, X. Chen, K. Wang, X. Zhang, Adv. Funct. Mater. 2024, 34, 2313726.

[52] X. Yan, Z. Li, Q. Wang, Y. Qu, Y. Xu, Y. Wang, J. Mater. Chem. C 2022, 10, 15408.

[53] J. Park, J. Lim, J. H. Lee, B. Jang, J. H. Han, S. S. Yoon, J. Y. Lee, ACS Appl. Mater. Interfaces 2021, 13, 45798.

[54] Z. Ye, H. Wu, Y. Xu, T. Hua, G. Chen, Z. Chen, X. Yin, M. Huang, K. Xu, X. Song, Z. Huang, X. Lv, J. Miao, X. Cao, C. Yang, Adv. Mater. 2024, 36, 2308314.

[55] J. Ochi, Y. Yamasaki, K. Tanaka, Y. Kondo, K. Isayama, S. Oda, M. Kondo, T. Hatakeyama, Nat. Commun. 2024, 15, 2361.

RIGHTS & PERMISSIONS

2025 The Author(s). FlexMat published by John Wiley & Sons Australia, Ltd on behalf of Nanjing University of Posts & Telecommunications.