Citation: Lin Danyan, Song Senchuan, Chen Zhiyong, Guo Pengran, Chen Jianghan, Shi Huahong, Mai Yuliang, Song Huacan. Luminescence Properties of the Conjugated System Containing Benzoimidazole Structural Units and Its Organic Light-Emitting Diode (OLED)[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 103-111. doi: 10.6023/cjoc201709047 shu

Luminescence Properties of the Conjugated System Containing Benzoimidazole Structural Units and Its Organic Light-Emitting Diode (OLED)

a.
School of Chemical Engineering and Technology, Sun Yat-Sen University, Guangzhou 510275
b.
Guangdong Petrochemical Research Institute, Guangzhou 510665
c.
China National Analysis Center of Guangzhou, Guangzhou 510070

Corresponding author: Song Huacan, songhc2007@163.com
Received Date: 29 September 2017
Revised Date: 6 October 2017
Available Online: 21 January 2017
Fund Project: the Special Project of Science and Technology Development of Guangdong Academy of Sciences 2017GDASCX-0104the Science and Technology Planning Project of Guangdong Province 2017A070702017the Science and Technology Planning Project of Guangdong Province 2017A040405040Project supported by the Science and Technology Planning Project of Guangdong Province (Nos. 2017A070702017, 2017A040405040) and the Special Project of Science and Technology Development of Guangdong Academy of Sciences (No. 2017GDASCX-0104)

Figures(7)

A series of conjugated compounds containing imidazole structure units were designed and synthesized. Their structures were characterized by ¹H NMR, ¹³C NMR, MS and elemental analysis. Their UV absorption wavelength (λ_a), fluorescence emission wavelength (λ_e), fluorescence quantum yield (Φ) and fluorescence lifetime (τ) were determined, and the relationships between the molecular structures and its spectral data were discussed. The results showed that these compounds possess strong luminescence characteristic, and the maximum value of Φ is 91%. 1, 4-Bis-(2-(1-benzylbenzimidazole))benzene (5b) was selected to fabricate organic light-emitting diode (OLED). Its main luminous peak is at 448 nm, the maximum brightness is 6790 cd•m^－2 when the voltage is 23.8 V (875 mA•cm^－2), the maximum current efficiency is 1.17 cd•A^－1, the maximum power efficiency is 0.96 lm•W^－1, and the maximum external quantum efficiency is 0.92%, which indicate that these compounds have great potential application value as OLED materials.
- benzoimidazole,
- luminescent property,
- organic light-emitting diode (OLED)
1. [1]
  Chen, Z.; Liu, X.-K.; Zheng, C.-J.; Ye, J.; Liu, C.-L.; Li, F.; Ou, X.-M.; Lee, C.-S.; Zhang, X.-H. Chem. Mater. 2015, 27, 5206. doi: 10.1021/acs.chemmater.5b01188
2. [2]
  Shao, J.-Y.; Yao, J.-N.; Zhong, Y.-W. Organometallics 2012, 31, 4302. doi: 10.1021/om300288h
3. [3]
  Oksana, T.; Nicolas, M.; Chiara, B. J. Mater. Chem. C 2016, 4, 5940. doi: 10.1039/C6TC01651K
4. [4]
  Peng, H.-D.; Wang, J.-Y.; Liu, Z.-H.; Pan, G.-B. Chem. Phys. Lett. 2016, 651, 133. doi: 10.1016/j.cplett.2016.03.048
5. [5]
  Li, R.-H.; Xiao, S.-H.; Li, Y.; Lin, Q.-F.; Zhang, R.-H.; Zhao, J.; Yang, C.-Y.; Zou, K.; Li, D.-S.; Yi, T. Chem. Sci. 2014, 5, 3922. doi: 10.1039/C4SC01243G
6. [6]
  Kumar, D.; Thomas, K. R. J. J. Photochem. Photobiol. A:Chem. 2011, 218, 162. doi: 10.1016/j.jphotochem.2010.12.018
7. [7]
  Yan, Y.-N.; Lin, D.-Y.; Pan, W.-L.; Li, X.-L.; Wan, Y.-Q.; Mai, Y.-L.; Song, H.-C. Spectrochim. Acta, Part A 2009, 74, 233. doi: 10.1016/j.saa.2009.06.020
8. [8]
  Dayan, O.; Yunusinan, M. Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 2015, 45, 1018. doi: 10.1080/15533174.2013.862655
9. [9]
10. [10]
  Yu, Q.-Y.; Lei, B.-X.; Liu, J.-M.; Shen, Y.; Xiao, L.-M.; Qiu, R.-L.; Kuang, D.-B.; Su, C.-Y. Inorg. Chim. Acta 2012, 392, 388. doi: 10.1016/j.ica.2012.03.047
11. [11]
  Murugan, P.; Hwang, K. C. Int. J. ChemTech Res. 2014, 6, 3518.
12. [12]
  Gao, Z.-Q.; Lee, C.-S.; Bello, I.; Lee, S. T.; Chen, R.-M.; Luh, T.-Y.; Shi, J.; Tang, C.-W. Appl. Phys. Lett. 1999, 74, 865. doi: 10.1063/1.123392
13. [13]
  Gostev, F. E.; Kol'tsova, L. S.; Petrukhin, A. N.; Titov, A. A.; Shiyonok, A. I.; Zaichenko, N. L.; Marevtsev, V. S.; Sarkisov, O. J. Photochem. Photobiol. A:Chem. 2003, 156, 1.
14. [14]
  Park, S.; Kwon, O.-H.; Kim, S.; Park, S.; Choi, M.-G.; Cha, M.; Park, S. Y.; Jang, D.-J. J. Am. Chem. Soc. 2005, 127, 10070. doi: 10.1021/ja0508727
15. [15]
  Lu, W.-F.; Yu, X.-H. Insul. Mater. Commun. 2000, 5, 5(in Chinese).
16. [16]
  Bilge, E.; Arslan, U. Spectrochim. Acta, Part A 2013, 103, 222. doi: 10.1016/j.saa.2012.10.055
17. [17]
  Xie, Q.; Liu, S.-G.; Li, X.-L.; Wu, Q.; Luo, Z.-D.; Fu, Xi.-Y.; Cao, W. Q.; Lan, G.-Q.; Li, D.; Zheng, W.-J.; Chen, T.-F. Dalton Trans. 2014, 43, 6973. doi: 10.1039/C4DT00198B
18. [18]
  Tmur, G.; Andre, F.; Teulon J.-M.; Daniel, P.; Michele, C.; Alix, C. J. Med. Chem. 1992, 35, 4455. doi: 10.1021/jm00101a024
19. [19]
  Meng, J.-P.; Lu, Y.-H.; Halqam, I.; Zou, C.-H. Chin. J. Biochem. Pharm. 2008, 29, 418(in Chinese).
20. [20]
  Hasegawa, M.; Nishigaki, N.; Washio, Y.; Kano, K.; Harris, P. A.; Sato, H.; Mori, I.; West, R. I.; Shibahara, M.; Toyoda, H.; Wang, L.; Nolte, R. T.; Veal, J. M.; Cheung, M. J Med. Chem. 2007, 50, 4453. doi: 10.1021/jm0611051
21. [21]
  Xu, J.-Y.; Zhang, L.; Wei, Z.; Hua, W.-Y.; Wu, X.-M.; Wang, Q.-J.; Zhang, J. J. Chin. Pharm. Univ. 2005, 36, 296(in Chinese).
22. [22]
  Bilge, E.; Yunus, B. Quim. Nova 2014, 37, 643.
23. [23]
  Kozaki, M.; Isoyama, A.; Kogen, A. A.; Okada, K. Org. Lett. 2005, 7, 115. doi: 10.1021/ol0476927
24. [24]
  Krebs, F. C.; Spanggaard, H. J. Org. Chem. 2002, 67, 7185. doi: 10.1021/jo025592d
25. [25]
  Varma, R. S. Green Chem. 1999, 1, 43 doi: 10.1039/a808223e
26. [26]
  Yan, Y.-N.; Pan, W.-L.; Song, H.-C. Dyes Pigm. 2010, 86, 249. doi: 10.1016/j.dyepig.2010.01.011
27. [27]
  Pan, W.-L.; Tan, H.-B.; Chen, Y.; Mu, D.-H.; Liu, H.-B.; Wan, Y.-Q.; Song, H.-C. Dyes Pigm. 2008, 76, 17. doi: 10.1016/j.dyepig.2006.07.034
28. [28]
  Song, S.-C.; Chen, J.-H.; Pan, W.-L.; Song, H.-C.; Shi, H.-H.; Mai, Y.-L.; Wen, W. Spectrochim. Acta, Part A 2017, 170, 157. doi: 10.1016/j.saa.2016.07.008
29. [29]
30. [30]
  Yang, L.; Chang, G.-J.; Zhang, L. Guangdong Chem. Ind. 2013, 40, 23(in Chinese).
31. [31]
  Tandon, S. S.; Thompson, K. L.; Bridson, N. J.; Dewan, C. J. Inorg. Chem. 1994, 33, 54. doi: 10.1021/ic00079a011
32. [32]
  ChemBioDraw Ultra 11.0. PerkinElmer, Waltham, MA, USA, 2013. Available online:http://www.cambridgesoft.com (accessed on 21 November 2013).
33. [33]
  Yu, Q.-Y.; Lei, B.-X.; Liu, J.-M.; Shen, Y.; Xiao, L.-M.; Qiu, R.-L.; Kuang, D.-B.; Su, C.-Y. Inorg. Chim. Acta 2012, 392, 388. doi: 10.1016/j.ica.2012.03.047
34. [34]
  Feng, G.-J.; Wang, Y.; Guo, T.-T. Acta Metrol. Sin. 2009, 30, 1(in Chinese). doi: 10.3969/j.issn.1000-1158.2009.z1.01
35. [35]
  Hu, L.-H.; Huang, Z.-B.; Ji, S.-J.; Zhu, J. Anal. Instrum. 2011, 5, 55(in Chinese). doi: 10.3969/j.issn.1001-232X.2011.05.014
36. [36]
  Zhang, X.-Q.; Chi, Z.-G.; Xu, B.-J.; Li, H.-Y.; Yang, Z.-Y.; Li, X.-F.; Liu, S.-W.; Zhang, Y.; Xu, J.-R. Dyes Pigm. 2011, 89, 56. doi: 10.1016/j.dyepig.2010.09.003
37. [37]
  Huang, J.-H.; Su, J.-H.; Li, X; Lam, M. K.; Fung, K. M.; Fan, H.-H.; Cheah, K. W.; Chen, C.-H.; Tai, H. J. Mater. Chem. 2011, 21, 2957. doi: 10.1039/c0jm03300f
38. [38]
  Tang, S.; Li, W.-J.; Shen, F.-Z.; Liu, D.-D.; Yang, B.; Ma, Y.-G. J. Mater. Chem. 2012, 22, 4401. doi: 10.1039/C1JM14639D
39. [39]
1. [1]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
2. [2]
  Ruixin XU , Hongtuo LI , Chen SHI , Yanhong YAN . Factors influencing the spectral properties of composite luminescent materials SrTiO₃: Eu³⁺/SrAl₂O₄: Eu²⁺, Dy³⁺. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2307-2316. doi: 10.11862/CJIC.20250055
3. [3]
  Ruoqian Zhang , Chaoqun Mu , Yali Hou , Mingming Zhang . 四苯乙烯基多组分金属有机笼的构筑及其固态发光性能研究. University Chemistry, 2025, 40(8): 277-283. doi: 10.12461/PKU.DXHX202410027
4. [4]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
5. [5]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
6. [6]
  Han ZHANG , Jianfeng SUN , Jinsheng LIANG . Hydrothermal synthesis and luminescent properties of broadband near-infrared Na₃CrF₆ phosphor. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 349-356. doi: 10.11862/CJIC.20240098
7. [7]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
8. [8]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
9. [9]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
10. [10]
  Yan ZHAO , Jiaxu WANG , Zhonghu LI , Changli LIU , Xingsheng ZHAO , Hengwei ZHOU , Xiaokang JIANG . Gd³⁺-doped Sc₂W3O₁₂: Eu³⁺ red phosphor: Preparation and luminescence performance. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 461-468. doi: 10.11862/CJIC.20240316
11. [11]
  Nian LIU , Biao ZHENG , Kun WANG , Chunbao ZHENG , Qingyan HAN , Enjie HE , Saidong XUE . Synthesis and spectroscopic performance of double perovskite Li_0.5La_0.5MgSrWO₆∶Mn⁴⁺ phosphors for plant growth lighting. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 129-140. doi: 10.11862/CJIC.20250069
12. [12]
  Shuhao FENG , Feibing XIONG , Yaqing LIN , Han SU , Xu HAN . Preparation and luminescent properties of alkaline metal doped Cd₃Al₂Ge₃O₁₂: Pr³⁺ orange phosphors. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 284-296. doi: 10.11862/CJIC.20250171
13. [13]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
14. [14]
  Pan Li , Huguo Shen , Cong Hua , Jinjie Fang , Xiangying Chi , Quan Jiang , Zichen Feng , Ye Kang , Bin Zheng . Synthesis and Characterization of an Aggregation-Induced Emission-Active Organic Cage Molecule: A Proposed Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(11): 337-345. doi: 10.12461/PKU.DXHX202502083
15. [15]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
16. [16]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
17. [17]
  Wenqian Zhang , Zhi Yang , Shunxiang Wu , Lei Yang , Bang Gu . Chemiluminescence: Colorful Experiments Unveiled. University Chemistry, 2026, 41(3): 307-321. doi: 10.12461/PKU.DXHX202505037
18. [18]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
19. [19]
  Junyang FENG , Xiaoli HAN , Yongjie SONG , Gang LI . Proton conduction and fluorescence properties of an ionic hydrogen-bonded organic framework constructed from dibromophthalic acid. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 693-702. doi: 10.11862/CJIC.20250350
20. [20]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(3527)
HTML views(241)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142