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

doi:10.6023/cjoc202112039

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1423-1430.DOI: 10.6023/cjoc202112039 Previous Articles Next Articles

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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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Abstract

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

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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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Fig. & Tab. 9

Figure 1. Common iridium complex phosphorescent materials

Scheme 1. Synthetic pathway and structures of target compounds

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

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

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

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

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

Table 2. Electroluminescent data of device 1~3

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

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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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