双极传输供体-受体(D-A)型铱(III)配合物近红外发光材料的合成及其电致发光性能

doi:10.6023/cjoc202111017

有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1831-1838.DOI: 10.6023/cjoc202111017 上一篇下一篇

研究论文

双极传输供体-受体(D-A)型铱(III)配合物近红外发光材料的合成及其电致发光性能

曹丽琴^a, 杨小琴^a, 李茂秋^a, 刘琳^a, 于俊婷^a^,^*(), 谭华^b^,^*()

a 湖南科技大学化学化工学院理论有机化学与功能分子教育部重点实验室湖南湘潭 411201
b 常州大学材料科学与工程学院江苏省光电热能量转化材料与应用工程实验室江苏常州 213164

收稿日期:2021-11-08 修回日期:2022-01-27 发布日期:2022-02-10
通讯作者: 于俊婷, 谭华
基金资助:
湖湘高层次人才聚集工程-创新团队(2021RC5028); 常州大学材料科学与工程学院、江苏省光电热能量转换材料及应用工程实验室(GDRGCS2020001)

Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features

Liqin Cao^a, Xiaoqin Yang^a, Maoqiu Li^a, Lin Liu^a, Junting Yu^a(), Hua Tan^b()

a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
b Jiangsu Engineering Laboratory of Light-Electricity-Heat Energy-Converting Materials and Applications, School of Materials Science and Engineering, Changzhou University, Changzhou, Jiangsu 213164

Received:2021-11-08 Revised:2022-01-27 Published:2022-02-10
Contact: Junting Yu, Hua Tan
Supported by:
Innovation Team of Huxiang High-Level Talent Gathering Engineering(2021RC5028); Jiangsu Engineering Laboratory of Light-Electricity-Heat Energy-Converting Materials and Applications, and the School of Materials and Engineering, Changzhou University(GDRGCS2020001)

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摘要/Abstract

将具有电子传输性能的二苯砜基团(PS)和空穴传输性能的咔唑(Cz)基团共价连接到吡啶甲酸(pic)上, 合成了具有双极传输特性的辅助配体pic-PSCz, 并构筑了一种双极传输的供体-受体(D-A)型铱(III)配合物(^tBuTPA-BTz- Iq)₂Ir(pic-PSCz) (^tBu为叔丁基, TPA为三苯胺, BTz为苯并三唑, Iq为异喹啉)近红外电致发光材料. 通过紫外-可见吸收光谱和光致发光光谱研究发现, 相比于配合物(Piq)₂Ir(pic-PSCz), (^tBuTPA-BTz-Iq)₂Ir(pic-PSCz)由于分子内较强的D-A作用, 其发射光谱红移约110 nm. 与已报道的配合物(TPA-BTz-Iq)₂Irpic相比, (^tBuTPA-BTz-Iq)₂Ir(pic-PSCz)分子内引入Cz和PS基团, 可以有效提高其电致发光效率, 其器件最大发射峰位于716 nm, 最大外量子效率(EQE_max)为0.87%, 为(TPA-BTz-Iq)₂Irpic器件效率的3倍(EQE_max为0.29%@712 nm).

关键词: 双极传输, 供体-受体, 近红外, 铱(III)配合物, 有机电致发光器件

In this paper, an auxiliary ligand with bipolar transmission characteristics, namely pic-PSCz, was synthesized by covalently connecting electron transport diphenylsulfone (PS) unit and hole transport carbazole (Cz) unit to picolinic acid (pic), and a bipolar transmission donor-acceptor (D-A) type near-infrared iridium (III) complex (^tBuTPA-BTz-Iq)₂Ir(pic-PSCz) (^tBu is tert-butyl, TPA is triphenylamine, BTZ is benzotriazole and Iq is isoquinoline) was designed and synthesized. Compared with (Piq)₂Ir(pic-PSCz), there is about 110 nm red shifted of (^tBuTPA-BTz-Iq)₂Ir(pic-PSCz) in emission spectra due to the strong D-A effect. Compared with the reported complex (TPA-BTz-Iq)₂Irpic, the photophysical and electroluminescent properties of (^tBuTPA-BTz-Iq)₂Ir(pic-PSCz) were improved by introducing Cz and PS units. Its maximum emission peak is located in the near-infrared region of 716 nm, and a maximum external quantum efficiency (EQE_max) of 0.87% is achieved, which is three times as much as its parent complex (TPA-BTz-Iq)₂Irpic (EQE_maxis 0.29% @712 nm).

Key words: bipolar transmission, donor-acceptor, near infrared, iridium (III) complex, organic light emitting device

引用此文

曹丽琴, 杨小琴, 李茂秋, 刘琳, 于俊婷, 谭华. 双极传输供体-受体(D-A)型铱(III)配合物近红外发光材料的合成及其电致发光性能[J]. 有机化学, 2022, 42(6): 1831-1838.

Liqin Cao, Xiaoqin Yang, Maoqiu Li, Lin Liu, Junting Yu, Hua Tan. Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1831-1838.

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图/表 10

图1. 配合物(tBuTPA-BTz-Iq)2Ir(pic-PSCz)和(Piq)2Ir(pic-PSCz)的化学结构和合成路线

Figure 1. Chemical structures and synthetic routes of complexes (tBuTPA-BTz-Iq)2Ir(pic-PSCz) and (Piq)2Ir(pic-PSCz)

图2. 配合物(Piq)2Ir(pic-PSCz)和(tBuTPA-BTz-Iq)2Ir(pic- PSCz)在二氯甲烷溶液中的紫外-可见吸收和光致发光光谱

Figure 2. UV-Vis absorption and photoluminescence spectra of (Piq)2Ir(pic-PSCz) and (tBuTPA-BTz-Iq)2Ir(pic-PSCz) complexes in dilute dichloromethane solution

Complex	λ_abs/nm	λ_em/nm	τ^c/μs	PLQY ^b/%	E_HOMO^d/eV	E_LUMO^d/eV	T_d/℃
(Piq)₂Ir(pic-PSCz)	(290, 345, 463)^a; (294, 347, 471)^b	603^a; 613^b	0.13	17.25	–5.26	–3.56	280
(^tBuTPA-BTz-Iq)₂Ir(pic-PSCz)	(294, 344, 463, 538)^a; (294, 348, 473, 550)^b	717^a; 710^b	0.33	0.69	–5.00	–3.58	378

表1. 铱(III)配合物的光物理电化学和热稳定性能数据

Table 1. Photophysical, electrochemical and thermal parameters properties of the iridium(III) complex

图3. 配合物(Piq)2Ir(pic-PSCz)和(tBuTPA-BTz-Iq)2Ir(pic- PSCz)的循环伏安曲线

Figure 3. Cyclic voltammogram curves of (Piq)2Ir(pic-PSCz) and (tBuTPA-BTz-Iq)2Ir(pic-PSCz) complexes

图4. 配合物(tBuTPA-BTz-Iq)2Ir(pic-PSCz)的HOMO和LU- MO轨道电子密度分布图

Figure 4. Electron density distribution of HOMO and LUMO for (tBuTPA-BTz-Iq)2Ir(pic-PSCz)

图5. 器件的能级和结构图

Figure 5. Energy level diagram and the structure of the OLEDs

图6. (tBuTPA-BTz-Iq)2Ir(pic-PSCz)在不同掺杂浓度下的电致发光光谱图

Figure 6. EL spectra of (tBuTPA-BTz-Iq)2Ir(pic-PSCz) at different doping concentration

图7. (tBuTPA-BTz-Iq)2Ir(pic-PSCz)在不同掺杂浓度下的EQE-J曲线

Figure 7. EQE-J characteristics of (tBuTPA-BTz-Iq)2Ir(pic- bPSCz) at different doping concentration

图8. (tBuTPA-BTz-Iq)2Ir(pic-PSCz)在不同掺杂浓度下的电流密度-电压-辐照度(J-V-R)曲线

Figure 8. Current density-voltage-radiance (J-V-R) curves of (tBuTPA-BTz-Iq)2Ir(pic-PSCz) at different doping concentration

Ratio/%	λ_EL,max/nm	EQE_max/%	R_max/(mW•Sr^–1•m^–2)
4.0	716	0.87	6640
6.0	716	0.60	5773
8.0	717	0.58	5595

表2. 基于(tBuTPA-BTz-Iq)2Ir(pic-PSCz)的电致发光器件数据

Table 2. Device data of (tBuTPA-BTz-Iq)2Ir(pic-PSCz)-based OLEDs

参考文献 31

[1]	Zampetti, A.; Minotto, A.; Cacialli, F. Adv. Funct. Mater. 2019, 29, 1807623. doi: 10.1002/adfm.201807623
[2]	Ibrahim-Ouali, M.; Dumur, F. Molecules 2019, 24, 1412. doi: 10.3390/molecules24071412
[3]	Chang, P.; Han, C.; Xu, H. Chin. J. Liq. Cryst. Displays 2021, 36, 62. (in Chinese)
	( 常鹏, 韩春苗, 许辉, 液晶与显示, 2021, 36, 62.)
[4]	Tang, S.; Sandstrom, A.; Lundberg, P.; Lanz, T.; Larsen, C.; van Reenen, S.; Kemerink, M.; Edman, L. Nat. Commun. 2017, 8, 1190. doi: 10.1038/s41467-017-01339-0 pmid: 29085078
[5]	Tang, S.; Murto, P.; Xu, X.; Larsen, C.; Wang, E.; Edman, L. Chem. Mater. 2017, 29, 7750. doi: 10.1021/acs.chemmater.7b02049
[6]	Barbieri, A.; Bandini, E.; Monti, F.; Praveen, V. K.; Armaroli, N. Top. Curr. Chem. 2016, 374, 47.
[7]	Xu, H.; Chen, R.; Sun, Q.; Lai, W.; Su, Q.; Huang, W.; Liu, X. Chem. Soc. Rev. 2014, 43, 3259. doi: 10.1039/C3CS60449G
[8]	Zhu, W.; Zhang, Y.; Xiong, W.; You, C.; Wu, X.; Zhu, M.; Wang, Y. J. Changzhou Univ. (Nat. Sci. Ed.) 2018, 30, 1. (in Chinese) doi: 10.1007/BF01475762
	( 朱卫国, 张友明, 熊雯婧, 游财发, 吴秀刚, 朱梦冰, 王亚飞, 常州大学学报(自然科学版), 2018, 30, 1.)
[9]	Lee, S. Y.; Yasuda, T.; Yang, Y. S.; Zhang, Q.; Adachi, C. Angew. Chem., Int. Ed. 2014, 53, 6402. doi: 10.1002/anie.201402992
[10]	Liu, X. K.; Chen, Z.; Zheng, C. J.; Chen, M.; Liu, W.; Zhang, X. H.; Lee, C. S. Adv. Mater. 2015, 27, 2025. doi: 10.1002/adma.201500013
[11]	Xue, J.; Xin, L.; Hou, J.; Duan, L.; Wang, R.; Wei, Y.; Qiao, J. Chem. Mater. 2017, 29, 4775. doi: 10.1021/acs.chemmater.7b00518
[12]	Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sinica 2017, 75, 4. (in Chinese)
	( 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, 4.)
[13]	Zhou, W.; Liu, Z.; Wang, Z.; Hu, S.; Liang, A. Chin. J. Org. Chem. 2019, 39, 5. (in Chinese) doi: 10.1002/cjoc.202190013
	( 周文静, 刘志谦, 王志平, 胡斯帆, 梁爱辉, 有机化学, 2019, 39, 5.)
[14]	You, C.; Liu, D.; Zhu, M.; Yu, J.; Zhang, B.; Liu, Y.; Wang, Y.; Zhu, W. J. Mater. Chem. C 2020, 8, 7079. doi: 10.1039/D0TC00479K
[15]	Zhang, Y.; Li, Q.; Cai, M.; Xue, J.; Qiao, J. J. Mater. Chem. C 2020, 8, 8484.
[16]	Ren, B.; Yi, J.; Zhong, D.; Zhao, Y.; Guo, R.; Sheng, Y.; Sun, Y.; Xie, L.; Huang, W. Acta Chim. Sinica 2020, 78, 1. (in Chinese)
	( 任保轶, 依建成, 钟道昆, 赵玉志, 郭闰达, 盛永刚, 孙亚光, 解令海, 黄维, 化学学报, 2020, 78, 1.)
[17]	Liu, D.; You, C.; Li, M.; Wang, S.; Zhang, K.; Zhang, B.; Yu, J.; Liu, Y.; Su, S.-J.; Zhu, W. J. Organomet. Chem. 2021, 931, 121615. doi: 10.1016/j.jorganchem.2020.121615
[18]	Zhou, Y.; Huang, R.; Yan, J.; Li, Y.; Qiu, H.; Yang, J.; Zheng, Y. Chem. J. Chin. Univ. 2022, 43, 1. (in Chinese)
	( 周永慧, 黄如军, 严健洋, 李亚军, 邱欢欢, 杨进轩, 郑佑轩, 高等学校化学学报, 2022, 43, 1.)
[19]	Tuong Ly, K.; Chen-Cheng, R.-W.; Lin, H.-W.; Shiau, Y.-J.; Liu, S.-H.; Chou, P.-T.; Tsao, C.-S.; Huang, Y.-C.; Chi, Y. Nat. Photonics 2016, 11, 63. doi: 10.1038/nphoton.2016.230
[20]	You, C.; Liu, D.; Yu, J.; Tan, H.; Zhu, M.; Zhang, B.; Liu, Y.; Wang, Y.; Zhu, W. Adv. Opt. Mater. 2020, 8, 2000154. doi: 10.1002/adom.202000154
[21]	Baldo, M. A.; Adachi, C.; Forrest, S. R. Phys. Rev. B 2000, 62, 10967. doi: 10.1103/PhysRevB.62.10967
[22]	Reineke, S.; Walzer, K.; Leo, K. Phys. Rev. B 2007, 75, 125328. doi: 10.1103/PhysRevB.75.125328
[23]	Murawski, C.; Leo, K.; Gather, M. C. Adv. Mater. 2013, 25, 6801.
[24]	Yu, J.; Tan, H.; Meng, F.; Lv, K.; Zhu, W.; Su, S. Dyes Pigm. 2016, 131, 231. doi: 10.1016/j.dyepig.2016.04.021
[25]	Yu, J.; Li, M.; Xu, C.; Meng, F.; Cao, J.; Tan, H.; Zhu, W. Dalton Trans. 2020, 49, 8785. doi: 10.1039/D0DT01415J
[26]	Yu, J.; Xu, C.; Meng, F.; Tan, H.; Li, M.; Zhu, W. Dyes Pigm. 2019, 166, 307. doi: 10.1016/j.dyepig.2019.03.047
[27]	Wei, Z.; Zhang, K.; Kim, C. K.; Tan, S.; Wang, S.; Wang, L.; Li, J.; Wang, Y. Chin. Chem. Lett. 2021, 32, 493. doi: 10.1016/j.cclet.2020.05.005
[28]	Li, M.; Yu, J.; Liu, D.; Tan, S.; Yang, X.; Cao, L.; Tan, Y.; Cao, J.; Tan, H.; Wang, Y.; Zhu, W. Synth. Met. 2021, 281, 116917. doi: 10.1016/j.synthmet.2021.116917
[29]	Ho, C.-L.; Yao, B.; Zhang, B.; Wong, K.-L.; Wong, W.-Y.; Xie, Z.; Wang, L.; Lin, Z. J. Organomet. Chem. 2013, 730, 144. doi: 10.1016/j.jorganchem.2013.01.001
[30]	Tan, H.; Zheng, X.; Zhu, J.; Yu, J.; Zhu, W. J. Mater. Chem. C 2019, 7, 13301. doi: 10.1039/C9TC04898G
[31]	Balijapalli, U.; Nagata, R.; Yamada, N.; Nakanotani, H.; Tanaka, M.; D'Aleo, A.; Placide, V.; Mamada, M.; Tsuchiya, Y.; Adachi, C. Angew. Chem., Int. Ed. 2021, 60, 8477. doi: 10.1002/anie.202016089

双极传输供体-受体(D-A)型铱(III)配合物近红外发光材料的合成及其电致发光性能

Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features

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