Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1,3,5-Tribenzoylbenzene as Electron-Acceptor

doi:10.6023/A19100372

Acta Chimica Sinica ›› 2020, Vol. 78 ›› Issue (2): 140-146.DOI: 10.6023/A19100372 Previous Articles Next Articles

Article

基于新型电子受体1,3,5-三苯酰基苯的两种热活化延迟荧光材料的合成及性能研究

王志强^a, 白美丹^b, 张明^b, 张智强^c, 冯勋^a, 郑才俊^b

a 洛阳师范学院化学化工学院河南省功能导向多孔材料重点实验室洛阳 471934;
b 电子科技大学光电科学与工程学院成都 610054;
c 郑州轻工业大学材料与化学工程学院郑州 450001

投稿日期:2019-10-16 发布日期:2019-12-31
通讯作者: 王志强, 张智强, 郑才俊 E-mail:wzq197811@lynu.edu.cn;zhangzq@zzuli.edu.cn;zhengcaijun@uestc.edu.cn
基金资助:
项目受国家自然科学基金（No.51773029）和河南省自然科学基金（No.182300410230）资助.

Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1,3,5-Tribenzoylbenzene as Electron-Acceptor

Wang Zhiqiang^a, Bai Meidan^b, Zhang Ming^b, Zhang Zhiqiang^c, Feng Xun^a, Zheng Caijun^b

a College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471934;
b School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China(UESTC), Chengdu 610054;
c Department of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001

Received:2019-10-16 Published:2019-12-31
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51773029) and the Henan Natural Science Foundation (No. 182300410230).

1. Supporting Information-A19100372.pdf.pdf(1492KB)

Abstract

Two thermally activated delayed fluorescence (TADF) materials TBP-DmCz and TBP-TmCz were successfully synthesized using 1,3,5-tribenzoylbenzene (TBP) as electron-acceptor, 1,8-dimethylcarbazole (DmCz) and 1,3,6,8-tetra-methylcarbazole (TmCz) as electron-donor, respectively. Thermal gravimetric analysis show that the thermal decomposition temperatures (T_d) are 479℃ for TBP-DmCz and 484℃ for TBP-TmCz and no glass transition was found for both materials during the differential scanning calorimetry investigations. The highest occupied molecular orbitals (HOMO) are confined on the carbazole unit, while the lowest unoccupied molecular orbitals (LUMO) are located on the 1,3,5-tribenzoylbenzene unit, and there is almost no overlap between HOMO and LUMO, which is the typical molecular orbital character of TADF materials. Meanwhile, TBP-DmCz and TBP-TmCz possess degenerated HOMO and LUMO, which would promote the radiative transitions as the transitions could take place from all degenerated LUMOs to HOMOs. The HOMO level of TBP-TmCz is obviously higher than that of TBP-DmCz due to increasing the number of methyl groups at the electron-donor carbazole, and the LUMO levels of TBP-DmCz and TBP-TmCz only show a small difference because these materials have the same electron-acceptor 1,3,5-tribenzoylbenzene. In toluene solution, these materials have very similar absorption spectra and exhibit absorption bands assigned to intramolecular charge-transfer transition. The spectral peaks are located at 488 nm for TBP-DmCz and 502 nm for TBP-TmCz, respectively, in toluene solution at room temperature. According to the fluorescence and phosphorescence spectra of these materials in 1,3-bis(N-carbazolyl)benzene (mCP) film at 77 K, the energy gaps between the lowest singlet and triplet (ΔE_ST) of TBP-DmCz and TBP-TmCz are calculated to be 0.05 and 0.01 eV, respectively. The fluorescence decay behaviors at different temperatures (100, 200 and 300 K) proved that emissions of TBP-DmCz and TBP-TmCz contain TADF component. The electroluminescence devices with TBP-DmCz and TBP-TmCz as the emitters show high efficiency and low efficiency roll-off. The maximum external quantum efficiencies of devices based on TBP-DmCz and TBP-TmCz are 13.6% and 18.3%, respectively.

Key words: electroluminescence, light-emitting material, thermally activated delayed fluorescence, 1,3,5-tribenzoylbenzene, carbazole

Cite this article

Wang Zhiqiang, Bai Meidan, Zhang Ming, Zhang Zhiqiang, Feng Xun, Zheng Caijun. Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1,3,5-Tribenzoylbenzene as Electron-Acceptor[J]. Acta Chimica Sinica, 2020, 78(2): 140-146.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Sun, Y. R.; Giebink, N. C.; Kanno, H.; Ma, B. W.; Thompson, M. E.; Forrest, S. R. Nature 2006, 440, 908.
[2] Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lussem, B.; Leo, K. Nature 2009, 459, 234.
[3] Helander, M. G.; Wang, Z. B.; Qiu, J.; Greiner, M. T.; Puzzo, D. P.; Liu, Z. W. Science 2011, 332, 944.
[4] Han, T.-H.; Lee, Y.; Choi, M.-R.; Woo, S.-H.; Hong, B. H.; Ahn, J.-H.; Lee, T.-W. Nat. Photonics 2012, 459, 105.
[5] Sasabe, H.; Kido, J. J. Mater. Chem. C 2013, 1, 1699.
[6] Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sinica 2017, 75, 367. (陈仕琦, 代军, 周凯峰, 罗艳菊, 苏仕健, 蒲雪梅, 黄艳, 卢志云, 化学学报, 2017, 75, 367.)
[7] Qiu, Z.; Tan, J.; Cai, N.; Wang, K.; Ji, S.; Huo, Y. Chin. J. Org. Chem. 2019, 39, 679. (邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.)
[8] He, X.; Xiao, Y.; Yuan, X.; Ye, S.; Jiang, H. Chin. J. Org. Chem. 2019, 39, 761. (何煦, 肖燏萍, 袁鑫磊, 叶尚辉, 姜鸿基, 有机化学, 2019, 39, 761.)
[9] Wang, F.; Cao, X.; Mei, L.; Zhang, X.; Hu, J.; Tao, Y. Chin. J. Chem. 2018, 36, 241.
[10] Zhou, W.; Liu, Z.; Wang, Z.; Hu, S.; Liang, A. Chin. J. Org. Chem. 2019, 39, 1214. (周文静, 刘志谦, 王志平, 胡斯帆, 梁爱辉, 有机化学, 2019, 39, 1214.)
[11] Xu, H.; Chen, R.; Sun, Q.; Huang, W.; Liu, X. Chem. Soc. Rev. 2014, 43, 3259.
[12] Volz, D.; Wallesch, M.; Fléchon, C.; Danz, M.; Verma, A.; Navarro, J. M.; Zink, D. M.; Bräse, S.; Baumann, T. Green Chem. 2015, 17, 1988.
[13] Chi, Y.; Tong, B.; Chou, P.-T. Coord. Chem. Rev. 2014, 281, 1.
[14] Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234.
[15] Dias, F. B.; Bourdakos, K. N.; Jankus, V.; Moss, K. C.; Kamtekar, K. T.; Bhalla, V.; Santos, J.; Bryce, M. R.; Monkman, A. P. Adv. Mater. 2013, 25, 3707.
[16] Zhang, D. D.; Duan, L. A.; Li, Y. L.; Zhang, D. Q.; Qiu, Y. J. Mater. Chem. C 2014, 2, 8191.
[17] Wang, H.; Xie, L.; Peng, Q.; Meng, L.; Wang, Y.; Yi, Y.; Wang, P. Adv. Mater. 2014, 26, 5198.
[18] Mei, L.; Hu, J.; Cao, X.; Wang, F.; Zheng, C.; Tao, Y.; Zhang, X.; Huang, W. Chem. Commun. 2015, 51, 13024.
[19] Cai, X.; Li, X.; Xie, G.; He, Z.; Gao, K.; Liu, K.; Chen, D.; Cao, Y.; Su, S. J. Chem. Sci. 2016, 7, 4264.
[20] Meng, L.; Wang, H.; Wei, X.; Liu, J.; Chen, Y.; Kong, X.; Lv, X.; Wang, P.; Wang, Y. ACS Appl. Mater. Interfaces 2016, 8, 20955.
[21] Wang, K.; Zheng, C. J.; Liu, W.; Liang, K.; Shi, Y. Z.; Tao, S. L.; Lee, C. S.; Ou, X. M.; Zhang, X. H. Adv. Mater. 2017, 29, 1701476.
[22] Lee, J.; Aizawa, N.; Yasuda, T. Chem. Mater. 2017, 29, 8012.
[23] Shi, Y. Z.; Wang, K.; Li, X.; Dai, G. L.; Liu, W.; Ke, K.; Zhang, M.; Tao, S. L.; Zheng, C. J.; Ou, X. M.; Zhang, X. H. Angew. Chem., Int. Ed. 2018, 57, 9480.
[24] Yu, L.; Wu, Z.; Xie, G.; Zeng, W.; Ma, D.; Yang, C. Chem. Sci. 2018, 9, 1385.
[25] Yang, Z.; Mao, Z.; Xu, C.; Chen, X.; Zhao, J.; Yang, Z.; Zhang, Y.; Wu, W.; Jiao, S.; Liu, Y.; Aldred, M. P.; Chi, Z. Chem. Sci. 2019, 10, 8129.
[26] Zhang, M.; Liu, W.; Zheng, C. J.; Wang, K.; Shi, Y. Z.; Li, X.; Lin, H.; Tao, S. L.; Zhang, X. H. Adv. Sci. 2019, 6, 1801938.
[27] Rajamalli, P.; Senthilkumar, N.; Gandeepan, P.; Huang, P. Y.; Huang, M. J.; Ren-Wu, C. Z.; Yang, C. Y.; Chiu, M. J.; Chu, L. K.; Lin, H. W.; Cheng, C. H. J. Am. Chem. Soc. 2016, 138, 628.
[28] Xie, Z.; Chen, C.; Xu, S.; Li, J.; Zhang, Y.; Liu, S.; Xu, J.; Chi, Z. Angew. Chem., Int. Ed. 2015, 54, 7181.
[29] Nikolaenko, A. E.; Cass, M.; Bourcet, F.; Mohamad, D.; Roberts, M. Adv. Mater. 2015, 27, 7236.
[30] Di, D.; Romanov, A. S.; Yang, L.; Richter, J. M.; Rivett, J. P. H.; Jones, S.; Thomas, T. H.; Jalebi, M. A.; Friend, R. H.; Linnolahti, M.; Bochmann, M.; Credgington, D. Science 2017, 356, 159.
[31] Wang, Z.; Zheng, C.; Wang, W.; Xu, C.; Ji, B.; Zhang, X. Inorg. Chem. 2016, 55, 2157.
[32] Wang, Z.; Sun, X.; Xu, C.; Ji, B. Front. Chem. 2019, DOI:10. 3389/fchem. 2019.00422
[33] Song, X.; Zhang, D.; Lu, Y.; Yin, C.; Duan, L. Adv. Mater. 2019, 31, 1901923.
[34] Kretzschmar, A.; Patze, C.; Schwaebel, S. T.; Bunz, U. H. F. J. Org. Chem. 2015, 80, 9126.
[35] Zhu, Y.; Zhang, Y.; Yao, B.; Wang, Y.; Zhang, Z.; Zhan, H.; Zhang, B.; Xie, Z.; Wang, Y.; Cheng, Y. Macromolecules 2016, 49, 4373.
[36] Wang, Z.; Cai, J.; Zhang, M.; Zheng, C.; Ji, B. Acta Chim. Sinica 2019, 77, 263. (王志强, 蔡佳林, 张明, 郑才俊, 吉保明, 化学学报, 2019, 77, 263.)
[37] 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.
[38] Huang, T.; Jiang, W.; Duan, L. J. Mater. Chem. C 2018, 6, 5577.
[39] Godumala, M.; Choi, S.; Cho, M. J.; Choi, D. H. J. Mater. Chem. C 2019, 7, 2172.
[40] Cao, X.; Zhang, D.; Zhang, S.; Tao, Y.; Huang, W. J. Mater. Chem. C 2017, 5, 7699.
[41] Godumala, M.; Choi, S.; Cho, M. J.; Choi, D. H. J. Mater. Chem. C 2016, 4, 11355.
[42] Cai, X.; Chen, D.; Gao, K.; Gan, L.; Yin, Q.; Qiao, Z.; Chen, Z.; Jiang, X.; Su, S.-J. Adv. Funct. Mater. 2017, 27, 1704927.
[43] Bai, M.-D.; Zhang, M.; Wang, K.; Shi, Y.-Z.; Chen, J.-X.; Lin, H.; Tao, S.-L.; Zheng, C.-J.; Zhang, X.-H. Org. Electron. 2018, 62, 220.

基于新型电子受体1,3,5-三苯酰基苯的两种热活化延迟荧光材料的合成及性能研究

Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1,3,5-Tribenzoylbenzene as Electron-Acceptor

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	Peng Tao, Xiaokang Zheng, Guoliang Wang, Xinghao Sheng, He Jiang, Wentao Li, Jibiao Jin, Sui-Hung Wong, Yanqin Miao, Hua Wang, Wai-Yeung Wong. Novel Bipolar Orange Emissive Iridium(III) Complexes: Design, Synthesis, and Electroluminescence^★ [J]. Acta Chimica Sinica, 2023, 81(8): 891-897.
[3]	Zhenyu Liu, Junfeng Rao, Shoujia Zhu, Bingyang Wang, Fan Yu, Quanyou Feng, Linghai Xie. Research Progress of Solution-Processed Self-Host Thermally Activated Delayed Fluorescence Materials [J]. Acta Chimica Sinica, 2023, 81(7): 820-835.
[4]	Yinfeng Wang, Meng Li, Chuanfeng Chen. Chiral Triptycene-Based Red Thermally Activated Delayed Fluorescence Polymers and Their Organic Light-Emitting Diodes^★ [J]. Acta Chimica Sinica, 2023, 81(6): 588-594.
[5]	Shaoqin Zhang, Meiqing Li, Zhongjun Zhou, Zexing Qu. Theoretical Study on the Multiple Resonance Thermally Activated Delayed Fluorescence Process [J]. Acta Chimica Sinica, 2023, 81(2): 124-130.
[6]	Lu Zhou, Jia-Xiong Chen, Shaomin Ji, Wen-Cheng Chen, Yanping Huo. Research Progress of Red Thermally Activated Delayed Fluorescent Materials Based on Quinoxaline [J]. Acta Chimica Sinica, 2022, 80(3): 359-372.
[7]	Tao Zhou, Yue Qian, Hongjian Wang, Quanyou Feng, Linghai Xie, Wei Huang. Recent Advances in Substituent Effects of Blue Thermally Activated Delayed Fluorescence Small Molecules [J]. Acta Chimica Sinica, 2021, 79(5): 557-574.
[8]	Cao Hongtao, Li Bo, Wan Jun, Yu Tao, Xie Linghai, Sun Chen, Liu Yuyu, Wang Jin, Huang Wei. Cyano-substituted Spiro[fluorine-9,9'-xanthene] Derivatives: Exciplex Emission and Property Manipulation [J]. Acta Chimica Sinica, 2020, 78(7): 680-687.
[9]	Ren Bao-Yi, Yi Jian-Cheng, Zhong Dao-Kun, Zhao Yu-Zhi, Guo Run-Da, Sheng Yong-Gang, Sun Ya-Guang, Xie Ling-Hai, Huang Wei. Conjugated Regulation of Phosphorescent Iridium (III) Complex Constructed from Spiro Ligand and Its Electroluminescent Performances [J]. Acta Chimica Sinica, 2020, 78(1): 56-62.
[10]	Wang Zhiqiang, Cai Jialin, Zhang Ming, Zheng Caijun, Ji Baoming. A Novel Yellow Thermally Activated Delayed Fluorescence Emitter For Highly Efficient Organic Light-Emitting Diodes [J]. Acta Chim. Sinica, 2019, 77(3): 263-268.
[11]	Chen Shiqi, Dai Jun, Zhou Kaifeng, Luo Yanju, Su Shijian, Pu Xuemei, Huang Yan, Lu Zhiyun. Synthesis and Characterization of New Solution-Processable Red Iridium (III) Complexes Based on a Phenylation Strategy [J]. Acta Chim. Sinica, 2017, 75(4): 367-374.
[12]	Cao Qiang, Chen Qi, Han Baohang. Recent Advance in Organic Porous Polycarbazoles: Preparation and Properties [J]. Acta Chim. Sinica, 2015, 73(6): 541-556.
[13]	Chen Zhao, Shan Wei, Yin Jun, Yu Guangao, Liu Shenghua. Efficient Construction of Carbazole Derivatives via New Benzyne Precursors of Four Acetylene Modules [J]. Acta Chim. Sinica, 2015, 73(10): 1007-1012.
[14]	Wang Fangfang, Tao Youtian, Huang Wei. Recent Progress of Host Materials for Highly Efficient Blue Phosphorescent OLEDs [J]. Acta Chimica Sinica, 2015, 73(1): 9-22.
[15]	Wu Youxiong, Ren Hongyang, Wu Yifang, Wang Bingxi. Theoretical Study of Energy Gaps for Naphthalimide-based Charge Transfer Compounds [J]. Acta Chim. Sinica, 2015, 73(1): 53-59.