Citation: Xu Guiying, Xue Rongming, Zhang Moyao, Li Yaowen, Li Yongfang. Synthesis of Pyrazine-based Hole Transport Layer and Its Application in p-i-n Planar Perovskite Solar Cells[J]. Acta Physico-Chimica Sinica, ;2021, 37(4): 200805. doi: 10.3866/PKU.WHXB202008050 shu

Synthesis of Pyrazine-based Hole Transport Layer and Its Application in p-i-n Planar Perovskite Solar Cells

1.
Laboratory of Advanced Optoelectronic Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, Jiangsu Province, China
2.
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

Corresponding author: Li Yaowen, ywli@suda.edu.cn
Received Date: 19 August 2020
Revised Date: 20 September 2020
Accepted Date: 23 September 2020
Available Online: 9 October 2020
Fund Project: the National Natural Science Foundation of China 51673138The project was supported by the National Natural Science Foundation of China (51922074, 51673138, 51820105003), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and Postgraduate Research & Practice Innovation Program of Jiangsu Province (KYCPTTPA8_2496)the National Natural Science Foundation of China 51820105003the National Natural Science Foundation of China 51922074the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and Postgraduate Research & Practice Innovation Program of Jiangsu Province KYCPTTPA8_2496

Planar p-i-n perovskite solar cells (pero-SCs) with solution-processed fabrication, low cost, flexible device fabrication, and negligible hysteresis have attracted significant interest. Hole transport material (HTM) plays a crucial role in improving the performance of p-i-n planar pero-SCs by facilitating hole extraction and then reducing surface recombination. Two types of HTMs have been used in p-i-n pero-SCs. p-Type inorganic semiconductors, such as NiO, CuI, Cu₂O, CuSCN, and graphene oxide, have shown good efficiency and stability; however, organic semiconductor-based HTMs (e.g., poly[bis(4-phenyl) (2, 4, 6-trimethylphenyl)amine] (PTAA), polyarylamine (poly-TPD), poly(N-9-heptadecanyl-2, 7-carbazole-alt-5, 5-(4, 7-di(thien-2-yl)-2, 1, 3-benzothiadiazole)) (PCDTBT), and triphenylamine or thiophene derivative) have outstanding processability for simple one-step solution process at low temperatures; therefore, they should be investigated further. However, their electrical properties are usually inferior than those of inorganic semiconductors, and additives are required to improve their mobility and conductivity, which complicates device processing and results in hysteresis and poor device stability. Therefore, for the organic semiconductor-based HTMs, new hole transport layer (HTL) materials should be developed with easy synthesis process, highly reproducible photovoltaic performance, and better understanding of the structure–property relationship between the HTL materials and the device performance. Herein, an X-type HTM 4, 4, 4'', 4'''-(pyrazine-2, 3, 5, 6-tetrayl)tetrakis(N, N-bis(4-methoxyphenyl)aniline) (PT-TPA) containing pyrazine as the molecular core and triphenylamine (TPA) derivative as branches was designed and synthesized. We introduce an electron-deficient para-diazine as the core and electron-donating methoxytriphenylamine as the peripheral unit to enhance the dipole moment of PT-TPA, which could induce an intermolecular charge transfer. Compared with 4, 4'', 4'', 4'''-silanetetrayltetrakis(N, N-bis(4-methoxyphenyl)aniline) (Si-OMeTPA), the pyrazine core not only endows PT-TPA with good crystallinity but also improves the charge transfer property and plane conjugation of the molecular center, which significantly enhances the hole mobility of PT-TPA. The p-i-n planar pero-SCs based on dopant-free PT-TPA HTL showed a power conversion efficiency of 17.52%, which is approximately 15% higher than that of the device with a Si-OMeTPA HTL.
- Pyrazine,
- Hole-transporting layer,
- Organic small molecule,
- p-i-n planar perovskite solar cell,
- Structure and property relationship
1. [1]
  Kojima, A.; Teshima, K.; Shirai, Y.; Miyasaka, T. J. Am. Chem. Soc. 2009, 131, 6050. doi: 10.1021/ja809598r doi: 10.1021/ja809598r
2. [2]
  Olaleru, S. A.; Kirui, J. K.; Wamwangi, D.; Roro, K. T.; Mwakikunga, B. Sol. Energy 2020, 196, 295. doi: 10.1016/j.solener.2019.12.025 doi: 10.1016/j.solener.2019.12.025
3. [3]
  Park, N. G. ACS Energy Lett. 2019, 4, 2983. doi: 10.1021/acsenergylett.9b02442 doi: 10.1021/acsenergylett.9b02442
4. [4]
  Zheng, X.; Hou, Y.; Bao, C.; Yin, J.; Yuan, F.; Huang, Z.; Song, K.; Liu, J.; Troughton, J.; Gasparini, N.; et al. Nat. Energy 2020, 5, 131. doi: 10.1038/s41560-019-0538-4 doi: 10.1038/s41560-019-0538-4
5. [5]
  Yang, D.; Sano, T.; Yaguchi, Y.; Sun, H.; Sasabe, H.; Kido, J. Adv. Funct. Mater. 2019, 29, 1970074. doi: 10.1002/adfm.201970074 doi: 10.1002/adfm.201970074
6. [6]
  Xue, R.; Zhang, M.; Luo, D.; Chen, W.; Zhu, R.; Yang, Y. M.; Li, Y.; Li, Y. Sci. China Chem. 2020, doi: 10.1007/s11426-020-9741-1
7. [7]
  Jia, X.; Zuo, C.; Tao, S.; Sun, K.; Zhao, Y.; Yang, S.; Cheng, M.; Wang, M.; Yuan, Y.; Yang J.; et al. Science Bulletin 2019, 64, 1532. doi: 10.1016/j.scib.2019.08.017 doi: 10.1016/j.scib.2019.08.017
8. [8]
  Cheng, M.; Zuo, C.; Wu, Y.; Li, Z.; Xu, B.; Hua, Y.; Ding, L. Science Bulletin 2020, 65 (15), 1237. doi: 10.1016/j.scib.2020.04.021 doi: 10.1016/j.scib.2020.04.021
9. [9]
  Sathiyan, G.; Syed. A. A.; Chen, C.; Wu, C.; Tao, L.; Ding, X.; Miao, Y.; Li, G.; Cheng, M.; Ding L. Nano Energy 2020, 72, 104673. doi: 10.1016/j.nanoen.2020.104673 doi: 10.1016/j.nanoen.2020.104673
10. [10]
  Bi, C.; Wang, Q.; Shao, Y.; Yuan, Y.; Xiao, Z.; Huang, J. Nat. Commun. 2015, 6, 7747. doi: 10.1038/ncomms8747 doi: 10.1038/ncomms8747
11. [11]
  Huang, C.; Fu, W.; Li, C. Z.; Zhang, Z.; Qiu, W.; Shi, M.; Heremans, P.; Jen, A. K. Y.; Chen, H. J. Am. Chem. Soc. 2016, 138, 2528. doi: 10.1021/jacs.6b00039 doi: 10.1021/jacs.6b00039
12. [12]
  Zhang, J.; He, Y.; Min, J. Acta Phys. -Chim. Sin. 2018, 34, 1221. doi: 10.3866/PKU.WHXB201803231
13. [13]
  Xu, L.; Chen, X.; Jin, J.; Liu, W.; Dong, B.; Bai, X.; Song, H.; Reiss, P. Nano Energy 2019, 63, 103860. doi: 10.1016/j.nanoen.2019.103860 doi: 10.1016/j.nanoen.2019.103860
14. [14]
  Son, M. K.; Steier, L.; Schreier, M.; Mayer, M. T.; Luo, J.; Grätzel, M. Energy Environ. Sci. 2017, 10, 912. doi: 10.1039/C6EE03613A doi: 10.1039/C6EE03613A
15. [15]
  Zhao, D.; Sexton, M.; Park, H. Y.; Baure, G.; Nino, J. C.; So, F. Adv. Energy Mater. 2015, 5, 1401855. doi: 10.1002/aenm.201500436 doi: 10.1002/aenm.201500436
16. [16]
  Li, X.; Liu, X.; Wang, X.; Zhao, L.; Jiu, T.; Fang, J. J. Mater. Chem. A 2015, 3, 15024. doi: 10.1039/C5TA04712A doi: 10.1039/C5TA04712A
17. [17]
  Meng, L.; You, J.; Guo, T. F.; Yang, Y. Acc. Chem. Res. 2016, 49, 155. doi: 10.1021/acs.accounts.5b00404 doi: 10.1021/acs.accounts.5b00404
18. [18]
  Jeon, N. J.; Noh, J. H.; Kim, Y. C.; Yang, W. S.; Ryu, S.; Seok, S. I. Nat. Mater. 2014, 13, 897. doi: 10.1038/nmat4014 doi: 10.1038/nmat4014
19. [19]
  Wang, Y. K.; Yuan, Z. C.; Shi, G. Z.; Li, Y. X.; Li, Q.; Hui, F.; Sun, B. Q.; Jiang, Z.; Liao, L. Adv. Funct. Mater. 2016, 26, 1375. doi: 10.1002/adfm.201504245 doi: 10.1002/adfm.201504245
20. [20]
  Labban, A. E.; Chen, H.; Kirkus, M.; Barbe, J.; Del Gobbo, S.; Neophytou, M.; McCulloch, I.; Eid, J. Adv. Energy Mater. 2016, 6, 1502101. doi: 10.1002/aenm.201502101 doi: 10.1002/aenm.201502101
21. [21]
  Chen, H.; Fu, W.; Huang, C.; Zhang, Z.; Li, S.; Ding, F.; Shi, M.; Li, C. Z.; Jen, A. K. Y.; Chen, H. Adv. Energy Mater. 2017, 7, 1700012. doi: 10.1002/aenm.201700012 doi: 10.1002/aenm.201700012
22. [22]
  Xue, R.; Zhang, M.; Xu, G.; Zhang, J.; Chen, W.; Chen, H.; Yang, M.; Cui, C.; Li, Y.; Li, Y. J. Mater. Chem. A 2018, 6, 404. doi: 10.1039/C7TA09716F doi: 10.1039/C7TA09716F
23. [23]
  Lin, H.; Chen, S.; Hu, H.; Zhang, L.; Ma, T.; Lai, J. Y. L.; Li, Z.; Qin, A.; Huang, X.; Tang, B.; Yan, H. Adv. Mater. 2016, 28, 8546. doi: 10.1002/adma.201600997 doi: 10.1002/adma.201600997
24. [24]
  Liu, Y.; Lai, J. Y. L.; Chen, S.; Li, Y.; Jiang, K.; Zhao, J.; Li, Z.; Hu, H.; Ma, T.; Lin, H.; et al. J. Mater. Chem. A 2015, 3, 13632. doi: 10.1039/C5TA03093E doi: 10.1039/C5TA03093E
25. [25]
  Liu, Y.; Mu, C.; Jiang, K.; Zhao, J.; Li, Y.; Zhang, L.; Li, Z.; Lai, J.; Hu, H.; Ma, T.; et al. Adv. Mater. 2015, 27, 1015. doi: 10.1002/adma.201404152 doi: 10.1002/adma.201404152
26. [26]
  Xu, L.; Zhang, Q. Sci. China Mater. 2017, 60, 1093. doi: 10.1007/s40843-016-5170-2 doi: 10.1007/s40843-016-5170-2
27. [27]
  Zhu, Y.; Champion, R.; Jenekhe, S. Macromolecules 2006, 39, 8712. doi: 10.1021/ma061861g doi: 10.1021/ma061861g
28. [28]
  Zhou, E.; Cong, J.; Yamakawa, S.; Wei, Q.; Nakamura, M.; Tajima, K.; Yang, C.; Hashimoto, K. Macromolecules 2010, 43, 2873. doi: 10.1021/ma100039q doi: 10.1021/ma100039q
29. [29]
  Chen, M.; Nie, H.; Song, B.; Li, L.; Sun, J. Z.; Qin, A.; Tang, B. Z. J. Mater. Chem. C 2016, 4, 2901. doi: 10.1039/C5TC03299G doi: 10.1039/C5TC03299G
30. [30]
  Liu, F.; Wu, F.; Tu, Z.; Liao, Q.; Gong, Y.; Zhu, L.; Li, Q.; Li, Z. Adv. Funct. Mater. 2019, 29, 1901296. doi: 10.1002/adfm.201901296 doi: 10.1002/adfm.201901296
31. [31]
  Zhang, D.; Xu, P.; Wu, T.; Ou, Y.; Yang, X.; Sun, A.; Cui, B.; Sun, H.; Hua, Y. J. Mater. Chem. A 2019, 7, 5221. doi: 10.1039/C8TA12139G doi: 10.1039/C8TA12139G
32. [32]
  Hua, Y.; Chen, S.; Zhang, D.; Xu, P.; Sun, A.; Ou, Y.; Wu, T.; Sun, H.; Cui, B.; Zhu, X. J. Mater. Chem. A 2019, 7, 10200. doi: 10.1039/C9TA01731C doi: 10.1039/C9TA01731C
33. [33]
  Zhao, Y.; Xu, G.; Guo, X.; Xia, Y.; Cui, C.; Zhang, M.; Song, B.; Li, Y.; Li, Y. J. Mater. Chem. A 2015, 3, 17991. doi: 10.1039/C5TA03801D doi: 10.1039/C5TA03801D
34. [34]
  Zhang, P.; Li, C.; Li, Y.; Yang, X.; Chen, L.; Xu, B.; Tian, W.; Tu, Y. Chem. Commun. 2013, 49, 4917. doi: 10.1039/C3CC41321G doi: 10.1039/C3CC41321G
35. [35]
  Deepa, M.; Salado, M.; Calio, L.; Kazim, S.; Shivaprasad, S. M.; Ahmad, S. Phys. Chem. Chem. Phys. 2017, 19, 4069. doi: 10.1039/C6CP08022G doi: 10.1039/C6CP08022G
36. [36]
  Saliba, M.; Matsui, T.; Seo, J. Y.; Domanski, K.; Correa-Baena, J. P.; Nazeeruddin, M. K.; Zakeeruddin, S. M.; Tress, W.; Abate, A.; Hagfeldt, A.; Grätzel, M. Energy Environ. Sci. 2016, 9, 1989. doi: 10.1039/C5EE03874J doi: 10.1039/C5EE03874J
37. [37]
  Ge, Q. Q.; Shao, J. Y.; Ding, J.; Deng, L. Y.; Zhou, W. K.; Chen, Y. X.; Ma, J. Y.; Wan, L. J.; Yao, J.; Hu, J. S.; Zhong, Y. W. Angew. Chem. Int. Ed. 2018, 57, 10959. doi: 10.1002/anie.201806392 doi: 10.1002/anie.201806392
38. [38]
  Luo, D.; Yang, W.; Wang, Z.; Sadhanala, A.; Hu, Q.; Su, R.; Shivanna, R.; Trindade, G. F.; Watts, J. F.; Xu, Z.; et al. Science 2018, 360, 1442. doi: 10.1126/science.aap9282 doi: 10.1126/science.aap9282
39. [39]
  Tu, Y.; Yang, X.; Su, R.; Luo, D.; Cao, Y.; Zhao, L.; Liu, T.; Yang, W.; Zhang, Y.; Xu, Z.; et al. Adv. Mater. 2018, 30, 1805085. doi: 10.1002/adma.201805085 doi: 10.1002/adma.201805085
40. [40]
  Li, Y.; Zhao, Y.; Chen, Q.; Yang, Y.; Liu, Y.; Hong, Z.; Liu, Z.; Hsieh, Y. T.; Meng, L.; Li, Y.; Yang, Y. J. Am. Chem. Soc. 2015, 137, 15540. doi: 10.1021/jacs.5b10614 doi: 10.1021/jacs.5b10614
41. [41]
  Cowan, S. R.; Roy, A.; Heeger, A. J. Phys. Rev. B 2010, 82, 245207. doi: 10.1103/PhysRevB.82.245207 doi: 10.1103/PhysRevB.82.245207
42. [42]
  Mandoc, M. M.; Kooistra, F. B.; Hummelen, J. C.; Boer, B. d.; Blom, P. W. M. Appl. Phys. Lett. 2007, 91, 263505.doi: 10.1063/1.2821368 doi: 10.1063/1.2821368
43. [43]
  Liu, X.; Yu, Z.; Wang, T.; Chiu, K.; Lin, F.; Gong, H.; Ding, L.; Cheng, Y. Adv. Energy Mater. 2020, 2001958. doi: 10.1002/aenm.202001958
1. [1]
  Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I₂ interface modification engineering on the performance of all-inorganic CsPbBr₃ perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
2. [2]
  Yixuan Gao , Lingxing Zan , Wenlin Zhang , Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091
3. [3]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
4. [4]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
5. [5]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
6. [6]
  Xiaoyao YIN , Wenhao ZHU , Puyao SHI , Zongsheng LI , Yichao WANG , Nengmin ZHU , Yang WANG , Weihai SUN . Fabrication of all-inorganic CsPbBr₃ perovskite solar cells with SnCl₂ interface modification. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 469-479. doi: 10.11862/CJIC.20240309
7. [7]
  Pengyu Dong , Yue Jiang , Zhengchi Yang , Licheng Liu , Gu Li , Xinyang Wen , Zhen Wang , Xinbo Shi , Guofu Zhou , Jun-Ming Liu , Jinwei Gao . NbSe₂纳米片优化钙钛矿太阳能电池的埋底界面. Acta Physico-Chimica Sinica, 2025, 41(3): 2407025-. doi: 10.3866/PKU.WHXB202407025
8. [8]
  Yipeng Zhou , Chenxin Ran , Zhongbin Wu . Metacognitive Enhancement in Diversifying Ideological and Political Education within Graduate Course: A Case Study on “Solar Cell Performance Enhancement Technology”. University Chemistry, 2024, 39(6): 151-159. doi: 10.3866/PKU.DXHX202312096
9. [9]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
10. [10]
  Yingqi BAI , Hua ZHAO , Huipeng LI , Xinran REN , Jun LI . Perovskite LaCoO₃/g-C₃N₄ heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 480-490. doi: 10.11862/CJIC.20240259
11. [11]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
12. [12]
  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
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]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Tianqi Bai , Kun Huang , Fachen Liu , Ruochen Shi , Wencai Ren , Songfeng Pei , Peng Gao , Zhongfan Liu . 石墨烯厚膜热扩散系数与微观结构的关系. Acta Physico-Chimica Sinica, 2025, 41(3): 2404024-. doi: 10.3866/PKU.WHXB202404024
17. [17]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
18. [18]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
19. [19]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
20. [20]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(449)
HTML views(78)

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