基于苯并呋喃-异喹啉的红光铱配合物的合成及电致发光性质

doi:10.6023/cjoc202112039

有机化学 ›› 2022, Vol. 42 ›› Issue (5): 1423-1430.DOI: 10.6023/cjoc202112039 上一篇下一篇

研究论文

基于苯并呋喃-异喹啉的红光铱配合物的合成及电致发光性质

聂飞^a, 黄观波^b, 戴雷^b, 陈少福^b, 籍少敏^a, 陈嘉雄^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:2021-12-28 修回日期:2022-01-27 发布日期:2022-02-27
通讯作者: 陈嘉雄, 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); 国家自然科学基金(21975053)

Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline

Fei Nie^a, Guanbo Huang^b, Lei Dai^b, Shaofu Chen^b, Shaomin Ji^a, Jiaxiong Chen^a(), Yanping Huo^a()

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

Received:2021-12-28 Revised:2022-01-27 Published:2022-02-27
Contact: Jiaxiong Chen, Yanping Huo
Supported by:
Natural Science Foundation of China(U2001222); Natural Science Foundation of China(21975055); Natural Science Foundation of China(21975053)

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摘要/Abstract

分别以6-异丙基-1-(5-甲基苯并呋喃-7-基)异喹啉、6-环戊基-1-(5-甲基苯并呋喃-7-基)异喹啉和6-异丁基-1-(5-甲基苯并呋喃-7-基)异喹啉为主配体, 以3,7-二乙基-4,6-壬二酮为辅助配体, 设计合成了三个红光铱配合物. 测试了它们的光物理、热学和电化学性质, 这些配合物具有较高的光致发光量子产率以及较短的磷光寿命. 以所合成的铱配合物为客体材料, 制备了三个相同结构的有机电致发光器件. 三个器件都实现了红光发射, 峰值分别位于637、635和636 nm处. 它们的开启电压较低, 均不超过2.8 V, 对应的最高外量子效率分别为14.1%、13.4%和13.3%, 最高电流效率分别为7.0、7.4和7.0 cd/A, 最高功率效率分别为7.9、8.3和7.8 lm/W. 这些数据表明所合成的三个铱配合物均为性能较好的红光磷光材料.

关键词: 铱配合物, 磷光寿命, 外量子效率

Three red iridium complexes were designed and synthesized by employing 6-isopropyl-1-(5-methylbenzofuran-7- yl)isoquinoline, 6-cyclopentyl-1-(5-methylbenzofuran-7-yl)isoquinoline and 6-isobutyl-1-(5-methylbenzofuran-7-yl)isoquinoline as main ligands, respectively, and 3,7-diethyl-4,6-nonedione as the auxiliary ligand. Their photophysical, thermal and electrochemical properties were investigated. These complexes have higher photoluminescence quantum yields and shorter phosphorescent lifetime. Three organic electroluminescent devices with same structure were fabrication using the iridium complexes as emitters. They all exhibited red electroluminescent emission with peak values at 637, 635 and 636 nm, respectively and showed low turn-on voltages below 2.8 V. And the highest external quantum efficiency of three devices was 14.1%, 13.4% and 13.3%, the highest current efficiency was 7.0, 7.4 and 7.0 cd/A, and the highest power efficiency was 7.9, 8.3, and 7.8 lm/W, respectively. These data indicate that the three iridium complexes can be used as efficient red phosphorescent materials.

Key words: iridium complex, phosphorescent lifetime, external quantum efficiency

引用此文

聂飞, 黄观波, 戴雷, 陈少福, 籍少敏, 陈嘉雄, 霍延平. 基于苯并呋喃-异喹啉的红光铱配合物的合成及电致发光性质[J]. 有机化学, 2022, 42(5): 1423-1430.

Fei Nie, Guanbo Huang, Lei Dai, Shaofu Chen, Shaomin Ji, Jiaxiong Chen, Yanping Huo. Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1423-1430.

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图/表 9

图1. 常见铱配合物磷光材料

Figure 1. Common iridium complex phosphorescent materials

图式1. 目标化合物的合成路线和结构

Scheme 1. Synthetic pathway and structures of target compounds

图2. 配合物4a~4c的TGA曲线(a)、DSC曲线(b)、氧化曲线(c)

Figure 2. TGA curves (a), DSC curves (b) and oxidation curves (c) of complexes 4a~4c

Complex	λ_em^a/nm	λ_em^b/nm	PLQY/%	τ/ns	T_d/℃	T_m/℃	HOMO/eV	LUMO/eV	E_g/eV
4a	624	626	78	658.18	342	265	–4.98	–3.03	1.95
4b	627	625	73	573.77	338	278	–4.98	–3.03	1.95
4c	628	625	70	766.61	356	269	–4.98	–3.03	1.95

表1. 配合物4a~4c的光物理和电化学数据

Table 1. Photophysical and electrochemical data of complexes 4a~4c

图3. 配合物4a~4c的紫外-可见吸收谱图和室温发射光谱图

Figure 3. UV-Vis absorption spectra and PL spectra at room temperature of complexes 4a~4c

图4. 配合物4a~4c的室温磷光光谱图(a)及发光衰减曲线(b)

Figure 4. Phosphorescent spectra at room temperature (a) and luminescent decay curves (b) of complexes 4a~4c

图5. 器件中所用材料的化学结构(a)及器件的能级图(b)

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

Device	EL(λ_max)/nm	V_on/V	EQE_max^a/EQE₁₀₀₀^b/%	CE_max^a/CE₁₀₀₀^b/(cd•A^–1)	PE_max^a/PE₁₀₀₀^b/(lm•W^–1)
1	637	<2.4	14.1/7.0	7.0/3.8	7.9/2.0
2	635	2.6~2.8	13.4/6.3	7.4/4.1	8.3/2.1
3	636	2.6~2.8	13.3/6.8	7.0/4.0	7.8/1.9

表2. Device 1~3的电致发光数据

Table 2. Electroluminescent data of device 1~3

图6. Devices 1~3的电致发光光谱图(a)、电流密度-电压-亮度(J-V-L)曲线(b)、电流效率-亮度-功率效率(CE-L-PE)曲线(c)及外量子效率-亮度(EQE-L)曲线(d)

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 external quantum efficiency-luminance (EQE-L) curves (d) of devices 1~3

参考文献 27

[1]	Qiu, Z. P.; Tan, J. H.; Cai, N.; Wang, K.; Ji, S. M.; Huo, Y. P. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese) doi: 10.6023/cjoc201807007
	(邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.) doi: 10.6023/cjoc201807007
[2]	Kang, S.; Jung, H.; Lee, H.; Park, S.; Kim, J.; Park, J. J. Mater. Chem. C 2019, 7, 14709. doi: 10.1039/C9TC04603H
[3]	Li, G.; Zheng, J.; Klimes, K.; Zhu, Z. Q.; Wu, J.; Zhu, H.; Li, J. ACS Appl. Mater. Interfaces 2019, 11, 40320. doi: 10.1021/acsami.9b13245
[4]	Liang, Z.-P.; Tang, R.; Qiu, Y.-C.; Wang, Y.; Lu, H.; Wu, Z.-G. Acta Chim. Sinica 2021, 79, 1401. (in Chinese) doi: 10.6023/A21070355
	(梁志鹏, 唐瑞, 邱雨晨, 王阳, 陆洪彬, 吴正光, 化学学报, 2021, 79, 1401.) doi: 10.6023/A21070355
[5]	Mao, X.; Xie, F.; Wang, X.; Wang, Q.; Qiu, Z.; Elsegood, M. R. J.; Bai, J.; Feng, X.; Redshaw, C.; Huo, Y.; Hu, J. Y.; Chen, Q. Chin. J. Chem. 2021, 39, 2154. doi: 10.1002/cjoc.202100157
[6]	Sun, N.; Jiang, C.; Li, Q.; Tan, D.; Bi, S.; Song, J. J. Mater. Sci.: Mater. Electron. 2020, 31, 20688. doi: 10.1007/s10854-020-04652-5
[7]	Tian, Q. S.; Yuan, S.; Shen, W. S.; Zhang, Y. L.; Wang, X. Q.; Kong, F. C.; Liao, L. S. Adv. Opt. Mater. 2020, 8, 2000556. doi: 10.1002/adom.202000556
[8]	Vadagaonkar, K. S.; Yang, C.-J.; Zeng, W.-H.; Chen, J.-H.; Patil, B. N.; Chetti, P.; Chen, L.-Y.; Chaskar, A. C. Dyes Pigm. 2019, 160, 301. doi: 10.1016/j.dyepig.2018.07.051
[9]	Wei, Q.; Fei, N.; Islam, A.; Lei, T.; Hong, L.; Peng, R.; Fan, X.; Chen, L.; Gao, P.; Ge, Z. Adv. Opt. Mater. 2018, 6, 1800512. doi: 10.1002/adom.201800512
[10]	Yang, X.; Jiao, B.; Dang, J. S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W. Y. ACS Appl. Mater. Interfaces. 2018, 10, 10227. doi: 10.1021/acsami.7b18330
[11]	Zhao, J.-H.; Hu, Y.-X.; Lu, H.-Y.; Lü, Y.-L.; Li, X. Org. Electron. 2017, 41, 56. doi: 10.1016/j.orgel.2016.11.039
[12]	Tan, J. H.; Huo, Y. P.; Cai, N.; Ji, S. M.; Li, Z. Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457. (in Chinese)
	(谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.) doi: 10.6023/cjoc201704015
[13]	Lepeltier, M.; Dumur, F.; Wantz, G.; Vila, N.; Mbomekallé, I.; Bertin, D.; Gigmes, D.; Mayer, C. R. J. Lumin. 2013, 143, 145. doi: 10.1016/j.jlumin.2013.05.004
[14]	Liang, B.; Jiang, C.; Chen, Z.; Zhang, X.; Shi, H.; Cao, Y. J. Mater. Chem. 2006, 16, 1281. doi: 10.1039/b515549e
[15]	Ouyang, X.; Chen, D.; Zeng, S.; Zhang, X.; Su, S.; Ge, Z. J. Mater. Chem. 2012, 22, 23005. doi: 10.1039/c2jm34462a
[16]	Thamilarasan, V.; Jayamani, A.; Manisankar, P.; Kim, Y.-I.; Sengottuvelan, N. Inorg. Chim. Acta 2013, 408, 240. doi: 10.1016/j.ica.2013.08.005
[17]	Ulbricht, C.; Beyer, B.; Friebe, C.; Winter, A.; Schubert, U. S. Adv. Mater. 2009, 21, 4418. doi: 10.1002/adma.200803537
[18]	Yang, X.; Guo, H.; Liu, B.; Zhao, J.; Zhou, G.; Wu, Z.; Wong, W. Y. Adv. Sci. 2018, 5, 1701067. doi: 10.1002/advs.201701067
[19]	Yang, X.; Zhou, G.; Wong, W. Y. Chem. Soc. Rev. 2015, 44, 8484. doi: 10.1039/C5CS00424A
[20]	Laskar, I. R.; Hsu, S.-F.; Chen, T.-M. Polyhedron 2005, 24, 189. doi: 10.1016/j.poly.2004.10.016
[21]	Tobita, S.; Yoshihara, T. Curr. Opin. Chem. Biol. 2016, 33, 39. doi: 10.1016/j.cbpa.2016.05.017 pmid: 27281510
[22]	Sun, Y.; Yang, X.; Feng, Z.; Liu, B.; Zhong, D.; Zhang, J.; Zhou, G.; Wu, Z. ACS Appl. Mater. Interfaces 2019, 11, 26152. doi: 10.1021/acsami.9b06749
[23]	Wang, D. Q. M.S. Thesis, Yunnan Normal University, Yunnan, 2019. (in Chinese)
	(王登强, 硕士论文,云南师范大学,云南, 2019.)
[24]	Zhuang, J.; Li, W.; Su, W.; Liu, Y.; Shen, Q.; Liao, L.; Zhou, M. Org. Electron. 2013, 14, 2596. doi: 10.1016/j.orgel.2013.06.029
[25]	Wang, X. M.S. Thesis, Dalian University of Technology, Dalian, 2011. (in Chinese)
	(王馨, 硕士论文,大连理工大学,大连, 2011.)
[26]	Su, Y. J.; Huang, H. L.; Li, C. L.; Chien, C. H.; Tao, Y. T.; Chou, P. T.; Datta, S.; Liu, R. S. Adv. Mater. 2003, 15, 884. doi: 10.1002/adma.200304630
[27]	Lips, S.; Frontana-Uribe, B. A.; Dorr, M.; Schollmeyer, D.; Franke, R.; Waldvogel, S. R. Chem.-Eur. J. 2018, 24, 6057. doi: 10.1002/chem.201800919

基于苯并呋喃-异喹啉的红光铱配合物的合成及电致发光性质

Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline

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