Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline

doi:10.6023/cjoc202301021

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1799-1807.DOI: 10.6023/cjoc202301021 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

ARTICLES

基于四氢喹啉的多重共振热活化延迟荧光材料的设计、合成及电致发光性能研究

梁凯淳^a, 白科研^b, 戴雷^b, 刘源^a, 叶泽聪^a^,^*(), 霍延平^a^,^*()

a 广东工业大学轻工化工学院广州 510006
b 广东阿格蕾雅光电材料有限公司广东佛山 528300

收稿日期:2023-01-24 修回日期:2023-03-06 发布日期:2023-03-30
通讯作者: 叶泽聪, 霍延平
基金资助:
国家自然科学基金(U2001222); 国家自然科学基金(21975055); 广东省基础与应用基础研究基金(2019B1515120035)

Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline

Kaichun Liang^a, Keyan Bai^b, Lei Dai^b, Yuan Liu^a, Zecong Ye^a(), Yanping Huo^a()

a School of Chemistry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006
b Guangdong Aglaia Optoelectronic Materials Co. Ltd., Foshan, Guangdong 528300

Received:2023-01-24 Revised:2023-03-06 Published:2023-03-30
Contact: Zecong Ye, Yanping Huo
Supported by:
National Natural Science Foundation of China(U2001222); National Natural Science Foundation of China(21975055); Guangdong Basic and Applied Basic Research Foundation(2019B1515120035)

1. .pdf(1320KB)

Abstract

Multiresonant thermally activated delayed fluorescence (MR-TADF) materials are a series of hot materials to realize ultra-high definition organic light-emitting diode (OLED) display. 5,9-Bis(1,2,3,4-tetrahydroquinoline)-5,9-dihydro-5,9- diaza-13b-boranaphtho[3,2,1-de]anthracene (THQBN) and 7-(tert-butyl)-5,9-bis(6-(tert-butyl)-4,4-dimethyl-1,2,3,4-tetra- hydroquinoline)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (Tt-THQBN) were designed and synthesized as organoboron based MR-TADF based on tetrahydroquinoline, whose structures were characterized by nuclear magnetic resonance and mass spectrum. The thermal stabilities, electrochemical properties and photophysical properties of these two molecules were measured. They had the similar deep-blue photoluminescence, narrow full-width at half-maximum and high photoluminescence quantum yield with the classical MR-TADF molecules. OLED devices were fabricated employing THQBN and Tt-THQBN as the guest materials. They all had deep blue emission at 455~458 nm. The CIE-y values of devices 2~4 are less than 0.1, and the full width of half maximum (FWHMs) of all devices were narrow, whitin the range of 34~38 nm. Their maximum brightness can exceed 1000 cd•m^–2 without serious efficiency roll-down. The device lifetime LT₉₀ of device 3 with best performance in these devices can reach 99 h at the initial brightness of 1000 cd•m^–2.

Key words: multiresonant thermally activated delayed fluorescence, organoboron based compound, full-width at half- maximum, device lifetime

Cite this article

Kaichun Liang, Keyan Bai, Lei Dai, Yuan Liu, Zecong Ye, Yanping Huo. Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1799-1807.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 10

Scheme 1. Synthetic route of target compounds

Figure 1. Curves of TGA (a), DSC (b) and oxidation (c) of THQBN and Tt-THQBN

Compd.	λ_abs^a/nm	λ_em^a/nm	FWHM/nm	PLQY^b/%	τ_p/ns	τ_d/μs	T_d^c/℃	T_m/℃	HOMO/eV	LUMO/eV	E_g/eV	ΔE_ST^d/eV
THQBN	435	449	24.5	83.4	6.1	51.1	356	201	–5.08	–2.34	2.74	0.09
Tt-THQBN	436	449.5	27.1	85.7	5.8	63.6	381	200	–4.99	–2.27	2.72	0.15
t-DABNA	445	459	22.3	82.9	—	—	419	—	–5.72	–3.02	2.70	0.09

Table 1. Photophysical and electrochemical data of THQBN and Tt-THQBN

Figure 2. UV-Vis absorption spectra and PL spectra at room temperature of THQBN, Tt-THQBN and t-DABNA

Figure 3. Phosphorescence and fluorescence spectra of THQBN and Tt-THQBN at 77 K

Compd.	Ф^a	Ф_F^b	Ф_TADF^b	k_F^c×10⁸/s^–1	k_IC^c×10⁷/s^–1	k_ISC^c×10⁶/s^–1	k_RISC^c×10⁴/s^–1	k_nr^d×10⁷/s^–1	ΔE_ST^c/eV
THQBN	0.834	0.814	0.020	1.33	2.66	3.94	1.68	3.17	0.19
Tt-THQBN	0.857	0.819	0.038	1.41	2.36	7.63	1.42	2.88	0.20

Table 2. Photophysical data of THQBN and Tt-THQBN

Figure 4. Theoretic calculation of frontier molecular orbitals of THQBN and Tt-THQBN

Figure 5. Energy level diagram of the device (a) and chemical structure of materials used in the device (b)

Device	EL(λ_max)/nm	FWHM/nm	V_on/V	CE_max^a/CE₁₀₀₀^b/(cd•A^–1)	LT₉₀^c/h
1	456	37	3.2	4.3/4.2	78
2	455	34	3.2	4.0/3.9	90
3	457	37	3.2	4.5/4.2	99
4	458	38	3.2	4.5/4.3	87

Table 3. Electroluminescent data of device 1~4

Figure 6. Electroluminescence spectra (a), current density-voltage-luminance (J-V-L) curves (b), current efficiency-luminance-power efficiency (CE-L-PE) curves (c) and lifetime (LT90) curve (d) of devices 1~4

References 42

[1]	Tang, C. W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913. doi: 10.1063/1.98799
[2]	Nie, F.; Huang, G. B.; Dai, L.; Chen, S. F.; Ji, S. M.; Chen, J. X.; Huo, Y. P. Chin. J. Org. Chem. 2019, 39, 1423. (in Chinese)
	(聂飞, 黄观波, 戴雷, 陈少福, 籍少敏, 陈嘉雄, 霍延平, 有机化学, 2022, 42, 1423.) doi: 10.6023/cjoc202112039
[3]	Kim, J. U.; Park, I. S.; Chan, C. Y.; Tanaka, M.; Tsuchiya, Y.; Nakanotani, H.; Adachi, C. Nat. Commun. 2020, 11, 1765. doi: 10.1038/s41467-020-15558-5
[4]	Hatakeyama, T.; Ikuta, T.; Shiren, K.; Nakajima, K.; Ni, J. Adv. Mater. 2016, 28, 2777. doi: 10.1002/adma.201505491
[5]	Suresh, S. M.; Hall, D.; Beljonne, D.; Olivier, Y.; Zysman-Colman, E. Adv. Funct. Mater. 2020, 30, 1908677. doi: 10.1002/adfm.v30.33
[6]	Han, S. H.; Jeong, J. H.; Yoo, J. W.; Lee, J. Y. J. Mater. Chem. C 2019, 7, 3082. doi: 10.1039/C8TC06575F
[7]	Zhang, Y.; Zhang, D.; Wei, J.; Hong, X.; Duan, L. Angew. Chem., nt. Ed. 2020, 36, 17499.
[8]	Liu, Y.; Xiao, X.; Ran, Y.; Bin, Z. Y.; You, J. S. Chem. Sci. 2021, 12, 9408. doi: 10.1039/D1SC02042K
[9]	Zhang, Y. W.; Zhang, D. D.; Duan, L. Angew. Chem., nt. Ed. 2019, 58, 16912.
[10]	Wang, Y.; Xu, Y.; Li, C.; Li, Z.; Wei, J. Angew. Chem.,Int. Ed. 2020, 59, 17442. doi: 10.1002/anie.v59.40
[11]	Liu, J. Y.; Zhu, Y. H.; Zhang, Q. S. Nat. Commun. 2022, 13, 4876. doi: 10.1038/s41467-022-32607-3
[12]	Yang, M.; Park, I. S.; Yasuda, T. J. Am. Chem. Soc. 2020, 142, 19468. doi: 10.1021/jacs.0c10081
[13]	Xu, Y. C.; Zhang, Z. L.; Wang, Y. Adv. Opt. Mater. 2020, 8, 1902142. doi: 10.1002/adom.v8.9
[14]	Ning, W. M.; Wang, H.; Gong, S. L.; Zhong, C.; Yang, C. L. Sci. China: Chem. 2022, 65, 1715. doi: 10.1007/s11426-022-1318-9
[15]	Cao, X. S.; Pan, K.; Miao, J. S.; Lv, X. L.; Huang, Z. Y.; Wei, Y. X.; Yang, C. L. Nat. Photonics 2022, 16, 803. doi: 10.1038/s41566-022-01083-y
[16]	Hu, Y. X.; Miao, J. S.; Hua, T.; Huang, Z. Y.; Qi, Y. Y.; Yang, C. L. J. Am. Chem. Soc. 2022, 144, 22976. doi: 10.1021/jacs.2c09543
[17]	Suresh, S. M.; Duda, E.; Hall, D.; Yao, Z.; Zysman-Colman, E. J. Am. Chem. Soc. 2020, 142, 6588. doi: 10.1021/jacs.9b13704
[18]	Zhang, Y.; Wei, J.; Zhang, D.; Yin, C.; Li, G.; Liu, Z. Angew. Chem., nt. Ed. 2020, 59, 17499.
[19]	Suresh, S. M.; Hall, D.; Zhang, M.; Si, C.; Cordes, D. B. Mater. Chem. Front. 2020, 4, 2018. doi: 10.1039/D0QM00190B
[20]	Yuan, Y.; Tang, X.; Du, X. Y.; Hu, Y.; Yu, Y. J.; Jiang, Z. Q.; Liao, L. S.; Lee, S. Adv. Opt. Mater. 2019, 7, 1801536. doi: 10.1002/adom.v7.7
[21]	Liang, X.; Yan, Z. P.; Han, H. B.; Wu, Z. G.; Zheng, Y. X.; Hong, M. Angew. Chem., nt. Ed. 2018, 57, 11316.
[22]	Kondo, Y.; Yoshiura, K.; Kitera, S.; Nishi, H.; Hatakeyama, T. Nat. Photonics 2019, 13, 678. doi: 10.1038/s41566-019-0476-5
[23]	Liu, G.; Sasabe, H.; Kumada, K.; Matsunaga, A.; Katagiri, H.; Kido, J. J. Mater. Chem. C 2021, 9, 8308. doi: 10.1039/D1TC01427G
[24]	Wu, Y.; Zhu, Y.; Zhang, Z.; Zhao, C.; He, J.; Yan, C.; Meng, H.; Mukherjee, S.; Shang, C.; Chen, X. Molecules 2022, 27, 348. doi: 10.3390/molecules27020348
[25]	Matsui, K.; Oda, S.; Yoshiura, K.; Nakajima, K.; Yasuda, N.; Hatakeyama, T. J. Am. Chem. Soc. 2018, 140, 1195. doi: 10.1021/jacs.7b10578 pmid: 29120174
[26]	Park, J.; Lim, J.; Jin, H. L.; Jang, B.; Ju, H. H.; Yoon, S. S. ACS Appl. Mater. Interfaces 2021, 13, 45798. doi: 10.1021/acsami.1c11399
[27]	Park, I. S.; Min, H.; Kim, J. U.; Yasuda, T. Adv. Opt. Mater. 2021, 9, 2101282. doi: 10.1002/adom.v9.24
[28]	Park, I.; Yang, M.; Shibata, H.; Amanokura, N.; Yasuda, T. Adv. Mater. 2022, 34, 2107951. doi: 10.1002/adma.v34.9
[29]	Ji, H.; Wjc, B.; Jk, A.; Jyl, B. Mater. Today Energy 2021, 21, 100792.
[30]	Tanaka, H.; Oda, S.; Ricci, G.; Gotoh, H.; Tabata, K.; Kawasumi, R.; Beljonne, D.; Olivier, Y; Hatakeyama, T. Angew. Chem.,Int. Ed. 2021, 60, 17910. doi: 10.1002/anie.v60.33
[31]	Im, Y.; Si, H. H.; Lee, J. Y. J. Mater. Chem. C 2018, 6, 5012. doi: 10.1039/C8TC00546J
[32]	Lee, Y. H.; Jung, J.; Yoo, S.; Lee, M. H. Adv. Opt. Mater. 2018, 6, 1800385. doi: 10.1002/adom.v6.17
[33]	Cui, L. S.; Nomura, H.; Geng, Y.; Kim, J. U.; Adachi, C. Angew. Chem., nt. Ed. 2017, 56, 1571.
[34]	Lee, Y. H.; Lee, D.; Lee, T.; Lee, J.; Min, H. L. Dyes Pigm. 2021, 188, 109224. doi: 10.1016/j.dyepig.2021.109224
[35]	Xia, G. Q.; Qu, C.; Zhu, Y. L.; Ye, J. J.; Ye, K. Q.; Zhang, Z. L.; Wang, Y. Angew. Chem., nt. Ed. 2021, 60, 9598.
[36]	Lim, H.; Cheon, H. J.; Woo, S. J.; Kwon, S. K.; Kim, Y. H.; Kim, J. J. Adv. Mater. 2020, 2004083.
[37]	Wang, T. T.; Hua, X. C.; Yu, Y. J.; Yuan, Y.; Feng, M. Q.; Jiang, Z. Q. Chin. J. Org. Chem. 2019, 39, 1436. (in Chinese) doi: 10.6023/cjoc201810016
	(王彤彤, 华晓晨, 郁友军, 袁熠, 冯敏强, 蒋佐权, 有机化学, 2019, 39, 1436.) doi: 10.6023/cjoc201810016
[38]	Zhang, Q.; Kuwabara, H.; Potscavage, W. J.; Huang, S.; Hatae, Y.; Shibata, T.; Adachi, C. J. Am. Chem. Soc. 2014, 136, 18070. doi: 10.1021/ja510144h
[39]	Yang, H. Y.; Zhang, M.; Zhao, J. W.; Pu, C. P.; Lin, H.; Tao, S. L.; Zheng, C. J.; Zhang, X. H. Chin. J. Chem. 2022, 40, 911. doi: 10.1002/cjoc.v40.8
[40]	Northey, T.; Penfold, T. J. Org. Electron. 2018, 59, 45. doi: 10.1016/j.orgel.2018.04.038
[41]	Oda, S.; Kawakami, B.; Kawasumi, R.; Okita, R.; Hatakeyama, T. Org. Lett. 2019, 21, 9311. doi: 10.1021/acs.orglett.9b03342
[42]	Paterson, L.; Mondal, A.; Heimel, P.; Lovrincic, R.; May, F.; Lennartz, C. Nat. Commun. 2019, 9, 4990. doi: 10.1038/s41467-018-07432-2

基于四氢喹啉的多重共振热活化延迟荧光材料的设计、合成及电致发光性能研究

Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 10

References 42

Related Articles 0

Recommended Articles

Metrics

Comments