骨架非稠合的电子受体在聚合物太阳能电池中的应用

doi:10.3866/PKU.WHXB201805091

物理化学学报 >> 2019, Vol. 35 >> Issue (4): 394-400.doi: 10.3866/PKU.WHXB201805091

所属专题：非富勒烯有机太阳能电池

骨架非稠合的电子受体在聚合物太阳能电池中的应用

章中强¹,张书华¹,刘志玺¹,张志国²,李永舫²,李昌治^1,*(),陈红征^1,*()

¹ 浙江大学高分子科学与工程学系，硅材料国家重点实验室，高分子合成与功能构造教育部重点实验室，杭州 310027
² 中国科学院化学研究所，北京 100190

收稿日期:2018-04-10 发布日期:2018-09-13
通讯作者: 李昌治,陈红征 E-mail:czli@zju.edu.cn;hzchen@zju.edu.cn
基金资助:
国家自然科学基金(21734008);国家自然科学基金(61721005);国家自然科学基金(21674093);国家自然科学基金(51473142);浙江省科技计划(2018C01047)

A Simple Electron Acceptor with Unfused Backbone for Polymer Solar Cells

Zhongqiang ZHANG¹,Shuhua ZHANG¹,Zhixi LIU¹,Zhiguo ZHANG²,Yongfang LI²,Changzhi LI^1,*(),Hongzheng CHEN^1,*()

¹ MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, P. R. China
² Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China

Received:2018-04-10 Published:2018-09-13
Contact: Changzhi LI,Hongzheng CHEN E-mail:czli@zju.edu.cn;hzchen@zju.edu.cn
Supported by:
the National Natural Science Foundation of China(21734008);the National Natural Science Foundation of China(61721005);the National Natural Science Foundation of China(21674093);the National Natural Science Foundation of China(51473142);the Zhejiang Province Science and Technology Plan, China(2018C01047)

摘要/Abstract

摘要：

非富勒烯电子受体由于其吸收强，能级可调，稳定性好等优点，近年来受到研究者的广泛关注，并且光电转换效率已突破14%。在本研究中，我们设计并合成了一种结构简单，易于合成的非稠环结构的非富勒烯电子受体ICTP。通过合理的结构设计，利用分子内的非共价作用力，实现了高的空间平面性。其在长波长区域宽且强的吸收和合适的能级水平，使得ICTP适合与许多聚合物给体材料搭配，制备太阳能电池。基于PBDB-T:ICTP的聚合物太阳能电池取得了4.43%的光电转换效率和0.97 V的开路电压。

关键词: 聚合物太阳能电池, 非富勒烯受体, 非共价作用力, 光电转换效率, 结构平面性

Abstract:

Non-fullerene electron acceptors have attracted enormous attention of the research community owing to their advantages of optoelectronic and chemical tunabilities for promoting high-performance polymer solar cells (PSCs). Among them, fused-ring electron acceptors (FREAs) are the most popular ones with the good structural planarity and rigidity, which successfully boost the power conversion efficiencies (PCEs) of PSCs to over 14%. In considering the cost-control of future scale-up applications, it is also worthwhile to explore novel structures that are easy to synthesize and still maintain the advantages of FREAs. In this work, we design and synthesize a new electron acceptor with an unfused backbone, 5, 5'-((2, 5-bis((2-hexyldecyl)oxy)-1, 4-phenylene)bis(thiophene-2-yl))bis(methanylylidene)) bis(3-oxo-2, 3-dihydro-1H-indene-2, 1-diylidene))dimal-ononitrile (ICTP), which contains two thiophenes and one alkoxy benzene as the core and 2-(3-oxo-2, 3-dihydroinden-1-ylidene) malononitrile (IC) as the terminal groups. The synthetic route to ICTP involves only three steps, with high yields. Density functional theory calculations indicate that the non-covalent interactions, O…H and O…S, help reinforce the space conformation between the central core and the terminals. ICTP shows broad and strong absorption in the long-wavelength range between 500 and 760 nm. The highest occupied molecular orbital and lowest unoccupied molecular orbital levels of ICTP were measured to be -5.56 and -3.84 eV by cyclic voltammetry. The suitable absorption and energy levels make ICTP a good acceptor candidate for medium bandgap polymer donors. The best devices based on PBDB-T:ICTP showed a PCE of 4.43%, with an open circuit voltage (V_OC) of 0.97 V, a short circuit current density (J_SC) of 8.29 mA∙cm^-2, and a fill factor (FF) of 0.55, after adding 1% 1, 8-diiodooctane (DIO) as the solvent additive. Atomic force microscopy revealed that DIO could ameliorate the strong aggregation in the blended film and lead to a smoother film surface. The hole and electron mobilities of the optimized device were measured to be 9.64 and 2.03 × 10^-5 cm²∙V^-1∙s^-1, respectively, by the space-charge-limited current method. The relatively low mobilities might be responsible for the moderate PCE. Further studies can be performed to enlarge the conjugation length by including more aromatic rings. This study provides a simple strategy to design non-fullerene acceptors and a valuable reference for the future development of PSCs.

Key words: Polymer solar cell, Non-fullerene acceptor, Non-covalent interaction, Power conversion efficiency, Structure planarity

章中强, 张书华, 刘志玺, 张志国, 李永舫, 李昌治, 陈红征. 骨架非稠合的电子受体在聚合物太阳能电池中的应用[J]. 物理化学学报, 2019, 35(4): 394-400.

Zhongqiang ZHANG, Shuhua ZHANG, Zhixi LIU, Zhiguo ZHANG, Yongfang LI, Changzhi LI, Hongzheng CHEN. A Simple Electron Acceptor with Unfused Backbone for Polymer Solar Cells[J]. Acta Phys. -Chim. Sin., 2019, 35(4): 394-400.

链接本文: https://www.whxb.pku.edu.cn/CN/10.3866/PKU.WHXB201805091

https://www.whxb.pku.edu.cn/CN/Y2019/V35/I4/394

参考文献

1	Lin Y. ; Zhan X. Acc. Chem. Res. 2016, 49, 175.
2	Li S. ; Zhang Z. ; Shi M. ; Li C. Z. ; Chen H. Phys. Chem. Chem. Phys. 2017, 19, 3440.
3	Li S. ; Liu W. ; Li C. Z. ; Shi M. ; Chen H. Small 2017, 13, 1701120.
4	Liu W. ; Li S. ; Huang J. ; Yang S. ; Chen J. ; Zuo L. ; Shi M. ; Zhan X. ; Li C. Z. ; Chen H. Adv. Mater. 2016, 28, 9729.
5	Lin Y. ; Zhan X. Mater. Horiz. 2014, 1, 470.
6	Li S. X. ; Liu W. Q. ; Shi M. M. ; Mai J. Q. ; Lau T. K. ; Wan J. H. ; Lu X. H. ; Li C. Z. ; Chen H. Z. Energy Environ. Sci. 2016, 9, 604.
7	Han J. ; Liang Q. ; Qu Y. ; Liu J. ; Han Y. Acta Phys. -Chim. Sin. 2018, 34, 391.
7	韩杰; 梁秋菊; 曲轶; 刘剑刚; 韩艳春. 物理化学学报, 2018, 34, 391.
8	Wang B. ; Liu W. ; Li H. ; Mai J. ; Liu S. ; Lu X. ; Li H. ; Shi M. ; Li C. Z. ; Chen H. J. Mater. Chem. A 2017, 5, 9396.
9	Zhang S. ; Qin Y. ; Zhu J. ; Hou J. Adv. Mater. 2018, 30, 1800868.
10	Cui Y. ; Yao H ; Yang C. ; Zhang S. ; Hou J. Acta Polym. Sin. 2018, (2), 223.
10	崔勇; 姚惠峰; 杨晨熠; 张少青; 侯剑辉. 高分子学报, 2018, (2), 223.
11	Vohra V. ; Kawashima K. ; Kakara T. ; Koganezawa T. ; Osaka I. ; Takimiya K. ; Murata H. Nat. Photon. 2015, 9, 403.
12	Huang J. ; Zhang X. ; Zheng D. ; Yan K. ; Li C. Z. ; Yu J. Solar RRL 2017, 1, 1600008.
13	He Z. ; Zhong C. ; Su S. ; Xu M. ; Wu H. ; Cao Y. Nat. Photon. 2012, 6, 593.
14	Xu J. ; Fu W. ; Yang S. ; Liu T. ; Li C. Z. ; Chen H. Acta Polym. Sin. 2018, (2), 164.
14	许景琦; 傅伟飞; 杨时达; 刘唐; 李昌治; 陈红征. 高分子学报, 2018, (2), 164.
15	Xu J. Q. ; Liu W. ; Liu S. Y. ; Ling J. ; Mai J. ; Lu X. ; Li C. Z. ; Jen A. K. Y. ; Chen H. Sci. China Chem. 2017, 60, 561.
16	Lin Y. ; Wang J. ; Zhang Z. G. ; Bai H. ; Li Y. ; Zhu D. ; Zhan X. Adv. Mater. 2015, 27, 1170.
17	Lin Y. ; Zhang Z. G. ; Bai H. ; Wang J. ; Yao Y. ; Li Y. ; Zhu D. ; Zhan X. Energy Environ. Sci. 2015, 8, 610.
18	Yao H. ; Chen Y. ; Qin Y. ; Yu R. ; Cui Y. ; Yang B. ; Li S. ; Zhang K. ; Hou J. Adv. Mater. 2016, 28, 8283.
19	Lin Y. ; He Q. ; Zhao F. ; Huo L. ; Mai J. ; Lu X. ; Su C. J. ; Li T. ; Wang J. ; Zhu J. ; et al J. Am. Chem. Soc. 2016, 138, 2973.
20	Yang Y. ; Zhang Z. G. ; Bin H. ; Chen S. ; Gao L. ; Xue L. ; Yang C. ; Li Y. J. Am. Chem. Soc. 2016, 138, 15011.
21	Zhang Z. ; Liu W. ; Rehman T. ; Ju H. X. ; Mai J. ; Lu X. ; Shi M. ; Zhu J. ; Li C. Z. ; Chen H. J. Mater. Chem. A 2017, 5, 9649.
22	Liu J. ; Chen S. ; Qian D. ; Gautam B. ; Yang G. ; Zhao J. ; Bergqvist J. ; Zhang F. ; Ma W. ; Ade H. ; et al Nat. Energy 2016, 1, 16089.
23	Zhang H. ; Li S. ; Xu B. ; Yao H. ; Yang B. ; Hou J. J. Mater. Chem. A 2016, 4, 18043.
24	Lin Y. ; Zhao F. ; Wu Y. ; Chen K. ; Xia Y. ; Li G. ; Prasad S. K. K. ; Zhu J. ; Huo L. ; Bin H. ; et al Adv. Mater. 2017, 29, 1604155.
25	Jiang K. ; Zhang G. ; Yang G. ; Zhang J. ; Li Z. ; Ma T. ; Hu H. ; Ma W. ; Ade H. ; Yan H. Adv. Energy Mater. 2018, 8, 1701370.
26	Jiang W. ; Yu R. ; Liu Z. ; Peng R. ; Mi D. ; Hong L. ; Wei Q. ; Hou J. ; Kuang Y. ; Ge Z. Adv. Mater. 2017, 29, 1703005.
27	Zhu J. ; Ke Z. ; Zhang Q. ; Wang J. ; Dai S. ; Wu Y. ; Xu Y. ; Lin Y. ; Ma W. ; You W. ; Zhan X. Adv. Mater. 2017, 29, 1704713.
28	Zuo L. ; Yu J. ; Shi X. ; Lin F. ; Tang W. ; Jen A. K. Adv. Mater. 2017, 29, 1702547.
29	Cui Y. ; Yao H. ; Gao B. ; Qin Y. ; Zhang S. ; Yang B. ; He C. ; Xu B. ; Hou J. J. Am. Chem. Soc. 2017, 139, 7302.
30	Liu F. ; Zhou Z. ; Zhang C. ; Zhang J. ; Hu Q. ; Vergote T. ; Liu F. ; Russell T. P. ; Zhu X. Adv. Mater. 2017, 29, 1606574.
31	Dai S. ; Zhao F. ; Zhang Q. ; Lau T. K. ; Li T. ; Liu K. ; Ling Q. ; Wang C. ; Lu X. ; You W. ; et al J. Am. Chem. Soc. 2017, 139, 1336.
32	Li S. ; Zhan L. ; Liu F. ; Ren J. ; Shi M. ; Li C. Z. ; Russell T. P. ; Chen H. Adv. Mater. 2018, 30, 1705208.
33	Zhang Z. ; Liu Z. ; Yan K. ; Li H. ; Liu W. ; Lu X. ; Li H. ; Chen H. ; Li C. Z. Acta Polym. Sin. 2018, (2), 295.
33	章中强; 刘志玺; 严康荣; 李焕斌; 刘文清; 路新慧; 李寒莹; 陈红征; 李昌治. 高分子学报, 2018, (2), 295.
34	Ullah F. ; Qian S. ; Yang W. ; Shah M. N. ; Zhang Z. ; Chen H. ; Li C. Z. Chinese Chem. Lett. 2017, 28, 2223.
35	Shah M. N. ; Zhang S. ; Sun Q. ; Ullah F. ; Chen H. ; Li C. Z. Tetrahedron Lett. 2017, 58, 2975.
36	Nguyen T. L. ; Choi H. ; Ko S. J. ; Uddin M. A. ; Walker B. ; Yum S. ; Jeong J. E. ; Yun M. H. ; Shin T. J. ; Hwang S. ; et al Energy Environ. Sci. 2014, 7, 3040.
37	Bin H. ; Gao L. ; Zhang Z. G. ; Yang Y. ; Zhang Y. ; Zhang C. ; Chen S. ; Xue L. ; Yang C. ; Xiao M. ; et al Nat. Commun. 2016, 7, 13651.
38	Bin H. ; Zhong L. ; Yang Y. ; Gao L. ; Huang H. ; Sun C. ; Li X. ; Xue L. ; Zhang Z. G. ; Zhang Z. ; et al Adv. Energy Mater. 2017, 7, 1700746.
39	Yu T. ; Xu X. ; Zhang G. ; Wan J. ; Li Y. ; Peng Q. Adv. Funct. Mater. 2017, 29, 1701491.
40	Fan Q. ; Su W. ; Meng X. ; Guo X. ; Li G. ; Ma W. ; Zhang M. ; Li Y. Solar RRL 2017, 1, 1700020.
41	Bin H. ; Zhang Z. G. ; Gao L. ; Chen S. ; Zhong L. ; Xue L. ; Yang C. ; Li Y. J. Am. Chem. Soc. 2016, 138, 4657.
42	Zhao W. ; Qian D. ; Zhang S. ; Li S. ; Inganas O. ; Gao F. ; Hou J. Adv. Mater. 2016, 28, 4734.
43	Elumalai N. K. ; Uddin A. Energy Environ. Sci. 2016, 9, 391.

[1]	尹媛, 郭振东, 陈高远, 张慧峰, 尹万健. 卤化钙钛矿太阳能电池的缺陷容忍及缺陷钝化研究进展[J]. 物理化学学报, 2021, 37(4): 2008048 - .
[2]	刘柏侨, 许韵华, 夏冬冬, 肖承义, 杨兆凡, 李韦伟. 基于非富勒烯电子受体的半透明有机太阳能电池[J]. 物理化学学报, 2021, 37(3): 2009056 - .
[3]	魏珍, 李敏杰, 陆文聪. 应用于染料敏化太阳能电池的基于染料R6的含有不同吸电子基团的有机染料的理论研究[J]. 物理化学学报, 2021, 37(10): 1905084 - .
[4]	冯诗语, 路皓, 刘泽坤, 刘亚辉, 李翠红, 薄志山. 通过非共价构象锁定和端基工程策略设计高效率的A-D-A型稠环电子受体[J]. 物理化学学报, 2019, 35(4): 355 -360 .
[5]	薛佩瑶,张俊祥,辛景明,RECHJeromy,李腾飞,孟凯鑫,王嘉宇,马伟,尤为,MARDER Seth R.,韩平畴,占肖卫. 第三组份端基对有机太阳能电池性能的影响[J]. 物理化学学报, 2019, 35(3): 275 -283 .
[6]	许青青,常春梅,李万宾,郭冰,国霞,张茂杰. 基于一种新型聚噻吩衍生物为给体的非富勒烯聚合物太阳能电池[J]. 物理化学学报, 2019, 35(3): 268 -274 .
[7]	吴仪, 孔静宜, 秦云朋, 姚惠峰, 张少青, 侯剑辉. 通过调节共轭聚合物侧链实现可绿色溶剂加工的非富勒烯太阳能电池[J]. 物理化学学报, 2019, 35(12): 1391 -1398 .
[8]	贾国骁,张少青,杨丽燕,何畅,范慧俐,侯剑辉. A-D-A型小分子电子给体光伏材料的端基修饰及其光伏性能[J]. 物理化学学报, 2019, 35(1): 76 -83 .
[9]	国霞,凡群平,崔超华,张志国,张茂杰. 基于无规三元共聚物的非卤溶液加工型高效聚合物太阳能电池[J]. 物理化学学报, 2018, 34(11): 1279 -1285 .
[10]	何畅,侯剑辉. 基于非富勒烯受体的溶液加工型全小分子太阳能电池研究进展[J]. 物理化学学报, 2018, 34(11): 1202 -1210 .
[11]	邓丹,周二军,魏志祥. 氟化策略：高效有机光伏材料的设计与应用[J]. 物理化学学报, 2018, 34(11): 1239 -1249 .
[12]	许利刚, 邱伟, 陈润锋, 张宏梅, 黄维. ZnO电极修饰层在钙钛矿太阳能电池中的应用[J]. 物理化学学报, 2018, 34(1): 36 -48 .
[13]	张少青,侯剑辉. 面向非富勒烯型有机光伏电池的聚合物给体材料设计[J]. 物理化学学报, 2017, 33(12): 2327 -2338 .
[14]	胥国成,邓先云,李军丽,张睿,谢云鹏,屠国力,夏江滨,卢兴. 碘化铅作为空穴传输层在P3HT:PC₆₁BM聚合物太阳能电池中的增强效果[J]. 物理化学学报, 2016, 32(6): 1307 -1313 .
[15]	武娜, 骆群, 吴振武, 马昌期. 电极界面缓冲层对P3HT:PC₆₁BM太阳能电池热稳定性的影响[J]. 物理化学学报, 2015, 31(7): 1413 -1420 .

骨架非稠合的电子受体在聚合物太阳能电池中的应用

A Simple Electron Acceptor with Unfused Backbone for Polymer Solar Cells

RichHTML

PDF

赞

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

Metrics

推荐阅读 0