Asymmetric Thermally Activated Delayed Fluorescence Materials Rendering High-performance OLEDs Through both Thermal Evaporation and Solution-processing

doi:10.1007/s40242-022-2111-0

Abstract

Abstract: Exploring high-efficiency thermally activated delayed fluorescence(TADF) materials is of great importance regarding to organic light-emitting diode(OLED). Herein, we present a design strategy for developing asymmetric TADF materials based on a diphenyl sulfone-phenoxazine structure, resulting in efficient TADF emitters(CzPXZ and t-CzPXZ) with aggregation-induced emission properties, while t-CzPXZ is modified with tert-butyl groups. The two compounds exhibit high solid-state luminescence, efficient TADF, and significantly impressive device performances by both thermal evaporation and solution processing. For an instance, CzPXZ and t-CzPXZ enable the thermally-evaporated OLEDs with high external quantum efficiencies(EQEs) of over 20%. Meanwhile, t-CzPXZ allows the solution-processed device with a high EQE of 16.3% with low-efficiency roll-off, attributing to the enhanced molecular solubility and suppressed excitons quenching through tert-butyl modification on t-CzPXZ. The results reveal that the proposed asymmetric structure is a promising approach for developing high-efficiency TADF materials and OLEDs.

Key words: Thermally activated delayed fluorescence, Asymmetric strategy, Organic light-emitting diode, Thermal evaporation, Solution processing

GAO Shiyuan, CHEN Xiaojie, GE Xiangyu, CHEN Zhu, ZHAO Juan, CHI Zhenguo. Asymmetric Thermally Activated Delayed Fluorescence Materials Rendering High-performance OLEDs Through both Thermal Evaporation and Solution-processing[J]. Chemical Research in Chinese Universities, 2022, 38(6): 1526-1531.

References

[1] Hong G., Gan X. M., Leonhardt C., Zhang Z., Seibert J., Busch J. M., Brase S., Adv.Mater., 2021, 33, 2005630;
[2] Li X. N., Xie Y. J., Li Z., Chem. Asian J., 2021, 16, 2817;
[3] Balijapalli U., Lee Y. T., Karunathilaka B. S. B., Tumen-Ulzii G., Auffray M., Tsuchiya Y., Nakanotani H., Adachi C., Angew Chem. Int. Ed., 2021, 60, 19364;
[4] Wang X. Q., Yang S. Y., Tian Q. S., Zhong C., Qu Y. K., Yu Y. J., Jiang Z. Q., Liao L. S., Angew Chem., 2021, 133, 5273;
[5] Cai Z. Y., Wu X., Liu H., Guo J. J., Yang D. Z., Ma D. G., Zhao Z. J., Tang B. Z., Angew Chem. Int. Ed., 2021, 60, 23635;
[6] Dong R. Z., Liu D., Li J. Y., Ma M. Y., Mei Y. Q., Li D. L., Jiang J. Y., Mater. Chem. Front., 2020, 6, 40;
[7] Zhou C. J., Cao C., Yang D. Z., Cao X. S., Liu H., Ma D. G., Li C. S., Yang C. L., Mater. Chem. Front., 2021, 5, 3209;
[8] Zhou J. X., Zeng X. Y., Xie F. M., He Y. H., Tang Y. Q., Li Y. Q., Tang J. X., Mater. Today Energy, 2021, 21, 100819;
[9] Chen Y., Zhang D. D., Zhang Y. W., Zeng X., Huang T. Y., Liu Z. Y., Li G. M., Duan L., Adv. Mater., 2021, 33, 2103293;
[10] Wang S. M., Zhang H. Y., Zhang B. H., Xie Z. Y., Wong W. Y., Mater. Sci. Eng. R Rep., 2020, 140, 100547;
[11] Sato K., Uchida S., Toriyama S., Nishimura S., Oyaizu K., Nishide H., Nishikitani Y., Adv. Mater. Technol., 2017, 2, 1600293;
[12] Sandstrom A., Dam H. F., Krebs F. C., Edman L., Nat. Commun., 2012, 3, 1;
[13] Lee S. M., Kwon J. H., Kwon S., Choi K. C., IEEE T. Electron Dev., 2017, 64, 1922;
[14] Han T. H., Lee Y. B., Choi M. R., Woo S. H., Bae S. H., Hong B. H., Ahn J. H., Lee T. W., Nature Photon., 2012, 6, 105;
[15] Huang T. Y., Jiang W., Duan L., J. Mater. Chem. C, 2018, 6, 5577;
[16] Zou Y., Gong S. L., Xie G. H., Yang C. L., Adv. Optical Mater.,2018, 6, 1800568;
[17] Li W. L., Huang Q. Y., Mao Z., Zhao J., Wu H. Y., Chen J. R., Yang Z., Li Y., Yang Z. Y., Zhang Y., Aldred M. P., Chi Z. G., Angew Chem. Int. Ed., 2020, 132, 3768;
[18] Yang J., Chi Z., Zhu W., Tang B. Z., Li Z., Sci. China Chem., 2019, 62, 1090;
[19] Yang Z. Y., Mao Z., Xie Z. L., Zhang Y., Liu S. W., Zhao J., Xu J. R., Chi Z. G., Aldred M. P., Chem. Soc. Rev., 2017, 46, 915;
[20] Chen X. L., Tao X. D., Wei Z. Z., Meng L. Y., Lin F. L., Zhang D. H., Jing Y. Y., Lu C. Z.,ACS Appl. Mater. Interfaces, 2021, 13, 46909;
[21] Tsai W. L., Huang M. H., Lee W. K., Hsu Y. J., Pan K. C., Huang Y. H., Ting H. C., Sarma M., Ho Y. Y., Hu H. C., Chen C. C., Lee M. T., Wong K. T., Wu C. C.,Chem. Commun.,2015, 51, 13662;
[22] Lee I. H., Song W., Lee J. Y., Org. Electron., 2016, 29, 22;
[23] Zhang Q. S., Li B., Huang S. P., Nomura H., Tanaka H., Adachi C., Nature Photon., 2014, 8, 326;
[24] Xie G. H., Luo J. J., Huang M. L., Chen T. H., Wu K. L., Gong S. L., Yang C. L., Adv. Mater., 2017, 29, 1604223;
[25] Yang Z., Mao Z., Xu C., Chen X. J., Zhao J., Yang Z. Y., Zhang Y., Wu W., Jiao S. B., Liu Y., Aldred M. P., Chi Z. G., Chem. Sci., 2019, 10, 8129;
[26] Wei W. C., Yang Z., Chen X. J., Liu T. T., Mao Z., Zhao J., Chi Z. G., J. Mater. Chem. C, 2020, 8, 3663;
[27] Zhao J., Chen X. J., Yang Z., Liu T. T., Yang Z. Y., Zhang Y., Xu J. R., Chi Z. G., J. Phys. Chem. C, 2018, 123, 1015;
[28] Tanaka H., Shizu K., Miyazaki H., Adachi C., Chem. Commun., 2012, 48, 11392;
[29] Chen J. X., Tao W. W., Xiao Y. F., Wang K., Zhang M., Fan X. C., Chen W. C., Yu J., Li S. L., Geng F. X., Zhang X. H., Lee C. S.,ACS Appl. Mater. Interfaces, 2019, 11, 29086;
[30] Kim H. J., Kang H., Jeong J. E., Park S. H., Koh C. W., Kim C. W., Woo H. Y., Cho M. J., Park S., Choi D. H., Adv. Funct. Mater., 2021, 31, 2102588;
[31] Xie F. M., An Z. D., Xie M., Li Y. Q., Zhang G. H., Zou S. J., Chen L., Chen J. D., Cheng T., Tang J. X.,J. Mater. Chem. C, 2020, 8, 5769;
[32] Wallwork N. R., Mamada M., Shukla A., McGregor S. K. M., Ahachi C., Namdas E. B., Lo S. C., J. Mater. Chem. C, 2022, 10, 4767;
[33] Xie G. Z., Li X. L., Chen D. J., Wang Z. H., Cai X. Y., Chen D. C., Li Y. C., Liu K. K., Cao Y., Su S. J., Adv. Mater., 2016, 28, 181;
[34] Godumala M., Choi S., Cho M. J., Choi D. H., J. Mater. Chem. C, 2019, 7, 2172;
[35] Sk B., Thangaraji V., Yadav N., Nanda G. P., Das S., Gandeepan P., Zysman-Colman E., Rajamalli P., J. Mater. Chem. C, 2021, 9, 15583;
[36] Yang G., Ran Y., Wu Y. M., Chen M. Q., Bin Z. Y., You J. S., Aggregate, 2021, e127