Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative

doi:10.6023/cjoc202601001

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2415-2422.DOI: 10.6023/cjoc202601001 Previous Articles Next Articles

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一种π-桥三联蒽型深蓝光材料的合成与性能研究

孙晓娟^a, 张明^b^,^*(), 田云飞^a, 王志强^a^,^*(), 郑才俊^c^,^*()

^a 洛阳师范学院化学化工学院洛阳市绿色合成与光功能材料重点实验室洛阳 471934
^b 陕西省计量科学研究院国家市场监管重点实验室(计量光学及应用) 西安 710100
^c 电子科技大学光电科学与工程学院成都 610054

收稿日期:2026-01-02 修回日期:2026-02-09 发布日期:2026-04-02
基金资助:
国家自然科学基金(22302088); 国家自然科学基金(62222503); 国家自然科学基金(62575056); 四川省自然科学基金(2024NSFSC0012); 四川省自然科学基金(2024NSFSC1446); 国家市场监督管理总局科技计划(2024MK126)

Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative

Xiaojuan Sun^a, Ming Zhang^b^,^*(), Yunfei Tian^a, Zhiqiang Wang^a^,^*(), Caijun Zheng^c^,^*()

^a Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934
^b Key Laboratory of Metrological Optics and Application for Sate Market Regulation, Shanxi Institute Metrology Science, Xi'an 710100
^c School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China, Chengdu 610054

Received:2026-01-02 Revised:2026-02-09 Published:2026-04-02
Contact: * E-mail: wzq197811@lynu.edu.cn;982938670@qq.com;zhengcaijun@uestc.edu.cn
Supported by:
National Natural Science Foundation of China(22302088); National Natural Science Foundation of China(62222503); National Natural Science Foundation of China(62575056); Sichuan Science and Technology Program(2024NSFSC0012); Sichuan Science and Technology Program(2024NSFSC1446); Technology Program of the State Administration for Market Regulation(2024MK126)

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Abstract

A deep blue electroluminescence material based on π-bridged teranthracene derivative 2-tert-butyl-9,10-bis(4-(10- phenylanthracen-9-yl)phenyl)anthracene (PBTAn) was synthesized and characterized by ¹H NMR, ¹³C NMR and HRMS. Theory calculation results show that PBTAn has a non-planar stereostructure, and the nearly degenerated highest occupied molecular orbital (HOMO, HOMO–1, HOMO–2) and lowest unoccupied molecular orbital (LUMO, LUMO+1, LUMO+2) are primarily located on the anthracene units. PBTAn shows efficient deep blue emissions both in CH₂Cl₂ solution (λ_max=424 nm) and doped film (λ_max=426 nm). The absolute photoluminescence quantum yields were measured to 0.79 and 0.83, respectively. The emission spectrum of neat PBTAn solid film (λ_max=439 nm) shows a larger red-shift compared to that acquired from CH₂Cl₂ solution and has two shoulder peaks at about 500 and 545 nm. The material PBTAn has excellent thermal stability, the decomposition temperature and glass transition temperature were measured to be 494 and 223 ℃ under N₂ atmosphere, respectively. Doped and non-doped electroluminescence devices were fabricated using PBTAn as emitter. The doped device based on PBTAn exhibits a deep blue emission at 440 nm with a CIE (Commission Internationale de l’Eclairage) coordinate of (0.15, 0.09). Meanwhile, the doped device shows high electroluminescence efficiency and low efficiency roll-off, the external quantum efficiency can reach to 4.1% and keep a higher value of 3.8% under the luminance 1000 cd•m^–2.

Key words: deep blue emitting material, anthracene derivative, organic light emitting diode, electroluminescence

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Xiaojuan Sun, Ming Zhang, Yunfei Tian, Zhiqiang Wang, Caijun Zheng. Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2415-2422.

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Fig. & Tab. 10

Scheme 1. Synthetic route of the material PBTAn

Figure 1. Stereostructure and molecular orbitals of the material PBTAn

Figure 2. Normalized UV-Vis absorption and photoluminescence (PL) spectra of the material PBTAn

Figure 3. TGA and DSC (inset) curves of the material PBTAn

Figure 4. Cyclic voltammogram (CV) curve of the material PBTAn

Figure 5. Energy level diagrams of non-doped device (a) and doped device (b), and molecular structures of materials used in devices (c)

Device	V_on^a/V	λ_max^b/nm	FWHM^b/nm	CIE (x, y)^b	L_max^c/(cd•m^–2)	EQE^d/% Max/1000	CE^d/(cd•A^–1) Max/1000	PE^d/(lm•W^–1) Max/1000
Non-doped	3.6	444	71	0.20, 0.21	3500	3.2/3.0	5.3/5.0	3.1/2.5
Doped	3.9	440	62	0.15, 0.09	2810	4.1/3.8	3.6/3.2	2.4/1.2

Table 1. Key electroluminescence performance data of the devices

Figure 6. Electroluminescence spectra of the devices

Figure 7. Current density-voltage-luminance curves of the devices

Figure 8. External quantum efficiency-luminance curves of the devices

References 52

[1]	Wang, S.; Zhou, J.; Jin, J.; Jiang, H.; Mai, M.; Duan, L.; Zhang, X.; Wong, W.-Y. ACS Appl. Mater. Interfaces 2025, 17, 31192. doi: 10.1021/acsami.5c05420
[2]	Jiang, X.; Tan, H.; Ping, L.; Hu, Z. Chin. J. Org. Chem. 2025, 45, 2896. (in Chinese) doi: 10.6023/cjoc202501017
	(江小妹, 谭海军, 平力文, 胡振光, 有机化学, 2025, 45, 2896.) doi: 10.6023/cjoc202501017
[3]	Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lussem, B.; Leo, K. Nature 2009, 459, 234. doi: 10.1038/nature08003
[4]	Zhang, H.; Xue, J.; Li, C.; Zhang, S.; Yang, B.; Liu, Y.; Wang, Y. Adv. Funct. Mater. 2021, 31, 2100704. doi: 10.1002/adfm.v31.25
[5]	Zhu, M.; Yang, C. Chem. Soc. Rev. 2013, 42, 4963. doi: 10.1039/c3cs35440g
[6]	Wang, Z.; Zheng, C.; Fu, W.; Xu, C.; Wu, J.; Ji, B. New J. Chem. 2017, 41, 14152. doi: 10.1039/C7NJ02806G
[7]	Xu, Z.; Tang, B. Z.; Wang, Y.; Ma, D. J. Mater. Chem. C 2020, 8, 2614. doi: 10.1039/C9TC06441A
[8]	He, J.; Wu, J.; Wang, J.; Xu, J.; Tang, B.; Zhao, Z. Chin. J. Org. Chem. 2024, 44, 2513. (in Chinese)
	(何俊初, 伍俊琪, 王江辉, 徐静文, 唐本忠, 赵祖金, 有机化学, 2024, 44, 2513.) doi: 10.6023/cjoc202403047
[9]	Wang, Y.; Du, C.; Cheng, Z.; Ge, S.; Feng, Z.; Wan, L.; Hu, Y.; Ma, X.; Su, Z.; Lu, P. ACS Appl. Mater. Interfaces 2024, 16, 51201. doi: 10.1021/acsami.4c05510
[10]	Jayabharathi, J.; Sivaraj, S.; Thanikachalam, V.; Seransenguttuvan, B. RSC Adv. 2020, 10, 25059. doi: 10.1039/d0ra03463k pmid: 35517441
[11]	Li, Z.; Li, Z.; Liu, J.; Han, W.; You, J.; Bin, Z. Chin. J. Org. Chem. 2024, 44, 2006. (in Chinese)
	(李治, 李祯龙, 刘俊杰, 憨卫国, 游劲松, 宾正杨, 有机化学, 2024, 44, 2006.) doi: 10.6023/cjoc202312006
[12]	Meng, G.; Zhang, D.; Wei, J.; Zhang, Y.; Huang, T.; Liu, Z.; Yin, C.; Hong, X.; Wang, X.; Zeng, X.; Yang, D.; Ma, D.; Li, G.; Duan, L. Chem. Sci. 2022, 13, 5622. doi: 10.1039/D2SC01543A
[13]	Fan, T.; Liu, Q.; Duan, L.; Zhang, D. J. Mater. Chem. C 2024, 12, 7989. doi: 10.1039/D4TC01533A
[14]	Kim, K.-H.; Baek, J. Y.; Cheon, C. W.; Moon, C.-K.; Sim, B.; Choi, M. Y.; Kim, J.-J.; Kim, Y.-H. Chem. Commun. 2016, 52, 10956. doi: 10.1039/C6CC05076J
[15]	Liu, F.; Man, X.; Liu, H.; Min, J.; Zhao, S.; Min, W.; Gao, L.; Jin, H.; Lu, P. J. Mater. Chem. C 2019, 7, 14881. doi: 10.1039/C9TC05040J
[16]	Huh, J.-S.; Ha, Y. H.; Kwon, S.-K.; Kim, Y.-H.; Kim, J.-J. ACS Appl. Mater. Interfaces 2020, 12, 15422. doi: 10.1021/acsami.9b21143
[17]	Li, Y.; Xu, Z.; Zhu, X.; Chen, B.; Wang, Z.; Xiao, B.; Lam, J. W. Y.; Zhao, Z.; Ma, D.; Tang, B. Z. ACS Appl. Mater. Interfaces 2019, 11, 17592. doi: 10.1021/acsami.9b03177
[18]	Ye, S.; Wang, Y.; Guo, R.; Zhang, Q.; Lv, X.; Duan, Y.; Leng, P.; Sun, S.; Wang, L. Chem. Eng. J. 2020, 393, 124694. doi: 10.1016/j.cej.2020.124694
[19]	Zhu, X.; Li, Y.; Wu, Z.; Lin, C.; Ma, D.; Zhao, Z.; Tang, B. Z. J. Mater. Chem. C 2021, 9, 5198. doi: 10.1039/D1TC00432H
[20]	Wang, Y.; Liu, W.; Ye, S.; Zhang, Q.; Duan, Y.; Guo, R.; Wang, L. J. Mater. Chem. C 2020, 8, 9678. doi: 10.1039/D0TC01964J
[21]	Huang, J.; Su, J.-H.; Tian, H. J. Mater. Chem. 2012, 22, 10977. doi: 10.1039/c2jm16855c
[22]	Han, P.; Lin, C.; Ma, D.; Qin, A.; Tang, B. Z. ACS Appl. Mater. Interfaces 2020, 12, 46366. doi: 10.1021/acsami.0c12722
[23]	Zheng, Y.; Wang, Z.; Wang, X.; Li, J.; Feng, X.; He, G.; Zhao, Z.; Lu, H. ACS Appl. Electron. Mater. 2021, 3, 422. doi: 10.1021/acsaelm.0c00960
[24]	Kim, B.; Park, Y.; Lee, J.; Yokoyama, D.; Lee, J.-H.; Kido, J.; Park, J. J. Mater. Chem. C 2013, 1, 432. doi: 10.1039/C2TC00185C
[25]	Shin, H.; Kim, B.; Jung, H.; Lee, J.; Lee, H.; Kang, S.; Moon, J.; Kim, J.; Park, J. RSC Adv. 2017, 7, 55582. doi: 10.1039/C7RA11773F
[26]	Sung, M. J.; Chubachi, H.; Satoh, R.; Kwon, S. K.; Pu, Y. J.; Kim, Y. H. J. Mater. Chem. C 2017, 5, 1090. doi: 10.1039/C6TC05308D
[27]	Kang, S.; Jung, H.; Lee, H.; Park, S.; Kim, J.; Park, J. J. Mater. Chem. C 2019, 7, 14709. doi: 10.1039/C9TC04603H
[28]	Qin, J.; Chen, J.; Qiao, Q.; Xiao, S.; Yang, D.; Ma, D. Chem. Sci. 2025, 16, 3536. doi: 10.1039/D4SC06232A
[29]	Liu, H.; Kang, L.; Li, J.; Liu, F.; He, X.; Ren, S.; Tang, X.; Lv, C.; Lu, P. J. Mater. Chem. C 2019, 7, 12073.
[30]	Jiang, H.; Li, H.; Jin, J.; Bodedla, G. B.; Tao, P.; Ma, D.; Wong, W.-Y. J. Mater. Chem. C 2023, 11, 6438. doi: 10.1039/D3TC00594A
[31]	Pachariyangkun, A.; Senapak, W.; Sudyoadsuk, T.; Supawadee, N.; Vinich, P. Org. Electron. 2020, 85, 105897. doi: 10.1016/j.orgel.2020.105897
[32]	Cao, C.; Yang, G.-X.; Tan, J.-H.; Shen, D.; Chen, W.-C.; Chen, J.-X.; Liang, J.-L.; Zhu, Z.-L.; Liu, S.-H.; Tong, Q.-X.; Lee, C.-S. Mater. Today Energy 2021, 21, 100727.
[33]	Xu, Y.; Liang, X.; Liang, Y.; Guo, X.; Hanif, M.; Zhou, J.; Zhou, X.; Wang, C.; Yao, J.; Zhao, R.; Hu, D.; Qiao, X.; Ma, D.; Ma, Y. ACS Appl. Mater. Interfaces 2019, 11, 31139. doi: 10.1021/acsami.9b10823
[34]	Guo, R.; Liu, W.; Ying, S.; Xu, Y.; Wen, Y.; Wang, Y.; Hub, D.; Qiao, X.; Yang, B.; Ma, D.; Wang, L. Sci. Bull. 2021, 3, 1729.
[35]	Kang, S.; Huh, J.-S.; Kim, J.-J.; Park, J. J. Mater. Chem. C 2020, 8, 11168. doi: 10.1039/D0TC01811B
[36]	Wu, L.; Xu, J.; Zhang, Z.; Xue, W.; Wang, T.; Yan, C.; He, J.; He, Y.; Yan, H.; Meng, H. Mater. Adv. 2022, 12, 1069.
[37]	Zhu, A.; Li, Z.; Guo, K.; Miao, Y.; Liu, B.; Yue, G. Prog. Chem. 2025, 37, 317. (in Chinese)
	(朱澳伟, 李战峰, 郭坤平, 苗艳勤, 刘宝友, 岳刚, 化学进展, 2025, 37, 317.) doi: 10.7536/PC240520
[38]	Jin, P.; Yang, X.; Yang, B.; Wang, X.-T.; Su, W.-T.; Zhan, S.-H.; Chen, X.; Sun, H.; Su, S.-J.; Hu, J.-Y. J. Mater. Chem. C 2024, 12, 1069. doi: 10.1039/D3TC04056A
[39]	Malatong, R.; Kaiyasuan, C.; Nalaoh, P.; Jungsuttiwong, S.; Sudyoadsuk, T.; Promarak, V. Dyes Pigm. 2021, 184, 108874. doi: 10.1016/j.dyepig.2020.108874
[40]	Hu, J.-Y.; Pu, Y.-J.; Satoh, F.; Kawata, S.; Katagiri, H.; Sasabe, H.; Kido, J. Adv. Funct. Mater. 2014, 24, 2064. doi: 10.1002/adfm.v24.14
[41]	Gao, C.; Prasad, S. K. K.; Zhang, B.; Dvořák, M.; Tayebjee, M. J. Y.; McCamey, D. R.; Schmidt, T. W.; Smith, T. A.; Wong, W. W. H. J. Phys. Chem. C 2019, 123, 20181. doi: 10.1021/acs.jpcc.9b07098
[42]	Haraguchi, A.; Goushi, K.; Sasaki, S.; Adach, C. J. Phys. Chem. Lett. 2025, 16, 5173. doi: 10.1021/acs.jpclett.5c00606
[43]	Li, Z.; Gan, G.; Ling, Z.; Guo, K.; Si, C.; Lv, X.; Wang, H.; Wei, B.; Hao, Y. Org. Electron. 2019, 66, 24. doi: 10.1016/j.orgel.2018.12.010
[44]	Yu, Y.; Wu, Z.; Li, Z.; Jiao, B.; Li, L.; Ma, L.; Wang, D.; Zhou, G.; Hou, X. J. Mater. Chem. C 2013, 1, 8117. doi: 10.1039/c3tc31743a
[45]	Si, C.; Li, Z.; Guo, K.; Lv, X.; Pan, S.; Chen, G.; Hao, Y.; Wei, B. Dyes Pigm. 2018, 148, 329. doi: 10.1016/j.dyepig.2017.09.027
[46]	Zhu, A.; Li, X.; Li, Z.; Si, C.; Miao, Y.; Liu, B.; Yue, G.; Tian, B. Dyes Pigm. 2024, 224, 112017. doi: 10.1016/j.dyepig.2024.112017
[47]	Wang, Z.-Q.; Xu, C.; Wang, W.-Z.; Duan, L.-M.; Li, Z.; Zhao, B.-T.; Ji, B.-M. New J. Chem. 2012, 36, 662. doi: 10.1039/C2NJ20809A
[48]	Sun, X.; Tian, Y.; Wang, Z. J. Iran. Chem. Soc. 2023, 20, 1873. doi: 10.1007/s13738-023-02803-z
[49]	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.
[50]	Wang, Z.; Bai, M.; Zhang, M.; Zhang, Z.; Feng, X.; Zheng, C. Acta Chem. Sinica 2020, 78, 140. (in Chinese)
	(王志强, 白美丹, 张明, 张智强, 冯勋, 郑才俊, 化学学报, 2020, 78, 140.) doi: 10.6023/A19100372
[51]	Ma, F.; Zhao, X.; Ji, H.; Zhang, D.; Hasrata, K.; Qi, Z. J. Mater. Chem. C 2020, 8, 12272. doi: 10.1039/D0TC02961K
[52]	He, Z.; Li, J.; Liu, D.; Wan, H.; Mei, Y.; Shi, C. J. Mater. Chem. C 2022, 10, 18189. doi: 10.1039/D2TC03875G

一种π-桥三联蒽型深蓝光材料的合成与性能研究

Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative

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