|
|
|
|
|
|
The Effect of Substituent Position on Photophysical Properties of Iridium Phosphorescent Complexes Based on Substituted 2,4-Diphenylpyridine |
CHANG Qiao-wen, CHEN Zhu-an, YAN Cai-xian, LIU Wei-ping, FENG Yang-yang* |
State Key Laboratory of Advanced Technologies for Comprehensive Utilization of Platinum Metals, Yunnan Precious Metals Lab Co., Ltd.,Kunming Institute of Precious Metals, Kunming 650106, China
|
|
|
Abstract Phosphorescent iridium complexes are the electroluminescent materials with the best comprehensive performance. Phosphorescent iridium complexes have been employed in organic light-emitting diodes (OLEDs), electrochemical light-emitting cells (LECs), photocatalysis, tumour diagnosis and sensors owing to their various advantages such as high quantum efficiency, good thermal stability and tunable emission colors. The color tuning of the iridium phosphorescent complex can be realized by changing the chemical structure of the main ligands and auxiliary ligands such as changing the conjugation degree of ligand, electron-donating and with drawing ability of substituents and substituent position. The influence of substituent position on iridium phosphorescent complex's photophysical properties was rarely researched. In this paper, we propose studying the effect of different substitution positions of methyl groups on the photophysical properties of iridium phosphorescent complexes. Two new iridium phosphorescence complexes (2,4-2Me-2,4-dppy)2Ir(tmd) and (3,5-2Me-dppy)2Ir(tmd) were synthesized with 2,4-diphenylpyridine of different methyl substituent positions as the main ligand and 2,2,6,6-tetramethylheptanedione as the auxiliary ligands. Their composition and spatial structure were characterized by elemental analysis, nuclear magnetic resonance (1H NMR and 13C NMR) and single-crystal X-ray diffraction. Bothcomplexes show slightly distorted octahedral configuration with space groups of C 12 / C 1 and P-1, with monoclinic and triclinic crystal systems, respectively. The thermal stability was tested by TG curves, the two complexes have good thermal stability with thermal decomposition temperatures of 307 ℃ and 318 ℃ respectively. UV-Vis spectra and photoluminescence spectra studied the photophysical properties of the complexes. The emission wavelengths of the two complexes in solution were 545 and 572 nm, respectively. The quantum yields in solution were 70% and 92%, respectively. The effect of substituent position on the photophysical properties of iridium phosphorescent complexes was further discussed. It was found that the position of the methyl group had a significant effect on the luminescence color and emission wavelength of 2,4-diphenylpyridine iridium phosphorescent complexes. Compared with the iridium phosphorescent complex obtained when the methyl group is at the 2 and 4 positions, the emission wavelength of the iridium complex obtained when the methyl group is at the 3 and 5 positions has a significant redshift, which is pure yellow light emission. It is a potential yellow light material expected to be applied in OLED lighting.
|
Received: 2022-07-15
Accepted: 2022-11-11
|
|
Corresponding Authors:
FENG Yang-yang
E-mail: fyy@ipm.com.cn
|
|
[1] Reineke S, Lindner F, Schwartz G, et al. Nature, 2009, 459 (7244): 234.
[2] Helander M G, Wang Z B, Qiu J, et al. Science, 2011, 332(6032): 944.
[3] Costa R D, Orti E, Bolink H J, et al. Angewandte Chemie International Edition, 2012, 51(33):8178.
[4] Eremina A A, Kinzhalov M A, Katlenok E A, et al. Inorganic Chemistry, 2020, 59(4): 2209.
[5] Tao P, Li W, Zhang J, et al. Adv. Funct. Mater., 2016, 26 (6): 881.
[6] Ulbricht C, Beyer B, Friebe C, et al. Advanced Materials, 2010, 21(44): 4418.
[7] Zhuang J, Li W, Su W, et al. Org. Electron., 2013, 14(10): 2596.
[8] King K A, Spellane R J, Watts R J. Journal of the Acerican Chemical Society, 1985, 107(5): 1431.
[9] Baldo M A, Lamansky S, Burrows P E, et al. Applied Physics Letters, 1999, 75(1): 4.
[10] Yang X, Zhou G, Wong W Y. Chemical Society Reviews, 2015, 44(23): 8484.
[11] Lamansky S, Djurovich P, Murphy D, et al. Journal of American Chemistry Society, 2001, 123(18): 4304.
[12] Lamansky S, Djurovich P, Murphy D, et al. Inorganic Chemistry, 2001, 40(7): 1704.
[13] Dedeian K, Djurovich P I, Garces F O, et al. Inorganic Chemistry, 1991, 30(8): 1685.
[14] Tamayo A B, Alleyne B D, Djurovich P I, et al. Journal of the American Chemistry Society, 2003, 125(24): 7377.
[15] Huang K, Wu H, Shi M, et al. Chemical Communication, 2009, 10: 1243.
[16] Chao K, Shao K, Peng T, et al.. Journal of Materials Chemistry C, 2013,1(8): 6800.
[17] Xu M L, Li W L, An Z W, et al. Applied Organometallic Chemistry, 2005, 19(12): 1225.
[18] Kajjam A B, Vaidyanathan S. The Chemical Record, 2017, 17: 1.
|
[1] |
TENG Jing1, 2, SHI Yao2, LI Hui-quan2, 3*, LIU Zuo-hua1*, LI Zhi-hong2, HE Ming-xing2, 4, ZHANG Chen-mu2. The Mechanism of Moisture Influence and Correction of Electroplating Sludges Testing With EDXRF[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(02): 419-425. |
[2] |
HAN Min-jie, WANG Xiang-you, XU Ying-chao*, CUI Ying-jun, LÜ Dan-yang. Research on the Factors Influencing the Non-Destructive Detection of
Potatoes by Near-Infrared Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(01): 37-42. |
[3] |
YANG Dong-feng1, LI Ai-chuan1, LIU Jin-ming1, CHEN Zheng-guang1, SHI Chuang1, HU Jun2*. Optimization of Seed Vigor Near-Infrared Detection by Coupling Mean Impact Value With Successive Projection Algorithm[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(10): 3135-3142. |
[4] |
LÜ Jia-nan, LI Jun-sheng*, HUANG Guo-xia, YAN Liu-juan, MA Ji. Spectroscopic Analysis on the Interaction of Chrysene With Herring Sperm DNA and Its Influence Factors[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(01): 210-214. |
[5] |
ZHAI Wen-yu, CHEN Lei*, XU Yi-xuan, KONG Xiang-yu. Analysis of Impact Factors and Applications by Using Spectral Absorption Depth for Quantitative Inversion of Carbonate Mineral[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(07): 2226-2232. |
[6] |
ZHANG Feng1, TANG Xiao-jun1*, TONG Ang-xin1, WANG Bin1, TANG Chun-rui2, WANG Jie2. A Mid-Infrared Wavelength Selection Method Based on the Impact Value of Variables and Population Analysis[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(06): 1795-1799. |
[7] |
XU Zhi-niu, HU Yu-hang, ZHAO Li-juan*, FAN Ming-yue. Fast and Highly Accurate Brillouin Frequency Shift Extracted Algorithm Based on Modified Quadratic Polynomial Fit[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2020, 40(03): 842-848. |
[8] |
QUE Hua-li1, 2, YANG Wen-liang1, XIN Xiu-li1, MA Dong-hao1, ZHANG Xian-feng1, ZHU An-ning1*. Ammonia Volatilization from Farmland Measured by Laser Absorption Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2020, 40(03): 885-890. |
[9] |
ZHOU Hao, YANG Zheng. The Reversible Ammonium Detection Based on the Coupled Microfluidic Chipand the Investigation of the Impact Factors[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2019, 39(12): 3749-3754. |
[10] |
ZHOU Kun-peng1, BAI Xu-fang1, BI Wei-hong2*. The Temperature, Turbidity and pH Impact Analysis of Water COD Detected by Fluorescence Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2019, 39(04): 1097-1102. |
[11] |
PAN Zhao1, CUI Yao-yao2, WU Xi-jun1*, YUAN Yuan-yuan1, LIU Ting-ting1. Krawtchouk Moment Method for the Quantitative Analysis of Polycyclic Aromatic Hydrocarbons Based on Fluorescence Three-Dimensional Spectra[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2018, 38(12): 3785-3789. |
[12] |
SUN Tong, MO Xin-xin, LIU Mu-hua*. Effect of Pericarp on Prediction Accuracy of Soluble Solid Content in Navel Oranges by Visible/Near Infrared Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2018, 38(05): 1406-1411. |
[13] |
YANG Bin1, GUO Hao-ran1, CHEN Xiao-long2, PAN Ke-wei2, GUI Xin-yang1, CAI Xiao-shu1, LIU Pei-jin3. Research on the Influence of Spectral Response on Radiation Spectroscopy Thermometry[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2018, 38(02): 638-642. |
[14] |
REN Lin-jiao, ZHANG Pei, QI Ru-bin, YIN Jing, LIU Shuai, ZHANG Ji-tao, CHEN Qing-hua, JIANG Li-ying*. Influencing Factors of Luminescence Properties of Carbon Dots Prepared by Ultrasonic[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2017, 37(11): 3354-3359. |
[15] |
ZHENG Feng1, LIU Li-ying1, LIU Xiao-xi2, LI Ye1, SHI Xiao-guang1, ZHANG Guo-yu1, HUAN Ke-wei1* . Study on Outliers Influence in NIR Quantitative Analysis Model [J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2016, 36(11): 3523-3529. |
|
|
|
|