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

doi:10.6023/cjoc202111017

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1831-1838.DOI: 10.6023/cjoc202111017 Previous Articles Next Articles

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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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Abstract

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

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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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Fig. & Tab. 10

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

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

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

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

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

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

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

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

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

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

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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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