基于3,4-二氰基噻吩的宽带隙共轭聚合物的设计合成与光伏应用

张拨; 余永高; 刘治田; 刘熙; 段春晖; 黄飞

doi:10.11777/j.issn1000-3304.2020.20011

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基于3,4-二氰基噻吩的宽带隙共轭聚合物的设计合成与光伏应用

论文 | 更新时间：2021-01-26

- 基于3,4-二氰基噻吩的宽带隙共轭聚合物的设计合成与光伏应用
- Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells
- 高分子学报 2020年51卷第6期页码：620-631
- 作者机构：
  
  1.武汉工程大学材料科学与工程学院光电与新能源材料研究所　武汉 430205
  2.华南理工大学发光材料与器件国家重点实验室高分子光电材料与器件研究所　广州 510640
  3.五邑大学纺织材料与工程学院　江门 529020
- 作者简介：
  
  E-mail: able.ztliu@wit.edu.cn Zhi-tian Liu, E-mail: able.ztliu@wit.edu.cn
  E-mail: liuxi_wyu@163.com Xi Liu, E-mail: liuxi_wyu@163.com
  E-mail: duanchunhui@scut.edu.cn Chun-hui Duan, E-mail: duanchunhui@scut.edu.cn
- 基金信息：
  
  国家自然科学基金(基金号 21875072，51973169)资助项目
- DOI：10.11777/j.issn1000-3304.2020.20011
  中图分类号：
- 纸质出版日期：2020-6，
  
  网络出版日期：2020-4-17，
  
  收稿日期：2020-1-27，
  
  修回日期：2020-3-5，
扫描看全文
张拨, 余永高, 刘治田, 刘熙, 段春晖, 黄飞. 基于3,4-二氰基噻吩的宽带隙共轭聚合物的设计合成与光伏应用[J]. 高分子学报, 2020,51(6):620-631.

Bo Zhang, Yong-gao Yu, Zhi-tian Liu, Xi Liu, Chun-hui Duan, Fei Huang. Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells[J]. Acta Polymerica Sinica, 2020,51(6):620-631.
张拨, 余永高, 刘治田, 刘熙, 段春晖, 黄飞. 基于3,4-二氰基噻吩的宽带隙共轭聚合物的设计合成与光伏应用[J]. 高分子学报, 2020,51(6):620-631. DOI： 10.11777/j.issn1000-3304.2020.20011.

Bo Zhang, Yong-gao Yu, Zhi-tian Liu, Xi Liu, Chun-hui Duan, Fei Huang. Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells[J]. Acta Polymerica Sinica, 2020,51(6):620-631. DOI： 10.11777/j.issn1000-3304.2020.20011.

摘要

利用3

4-二氰基噻吩(DCT)为电子受体单元，苯并双噻吩(BDT)为电子给体单元，并结合不同侧链取代的噻吩为

桥，设计合成了一系列新型宽带隙共轭聚合物：PB3TCN-C32、PB3TCN-C36、PB3TCN-C36-R以及PB3TCN-C40. 这些聚合物具有较宽的光学带隙(

1.8 eV)、较深的最高占有分子轨道(HOMO)能级. 与非富勒烯受体(IT-4F)结合制备了有机太阳电池器件，其中聚合物PB3TCN-C40实现了高达11.2%的能量转换效率(PCE)，其开路电压(

)为0.92 V，短路电流密度(

)为18.9 mA cm

−2

，填充因子(FF)为0.64，是目前文献报道基于氰基噻吩类聚合物材料的最好结果. 同时，该体系具有低至0.6 eV的能量损失. 这些结果表明DCT是一种极具潜力的实现宽带隙、深HOMO能级共轭聚合物的构筑单元，有望实现更高能量转换效率的有机太阳电池.

Abstract

In this contribution

we report a set of wide bandgap conjugated polymers (PB3TCN-C32

PB3TCN-C36

PB3TCN-C36-R

PB3TCN-C40) based on 3

4-dicyanothiophene (DCT) for use as electron donors in organic solar cells (OSCs). The polymers exhibit wide optical bandgaps (

1.8 eV) and deep highest occupied molecular orbital (HOMO) levels due to the high electron affinity of DCT unit. The optoelectronic properties

active layer morphology

and device performance of the polymers can be tuned by side chains. As a result

high-performance solar cells with a decent power conversion efficiency (PCE) of 11.2% have been achieved by PB3TCN-C40 when using IT-4F as the electron acceptor. Noticeably

the polymers afforded a high open circuit voltage (

) of up to 0.92 V and an energy loss (

loss

) as low as 0.6 eV even though there is not any additional withdrawing groups such as F

or S atom on the polymers

which is superior to the leading polymer donors in the field of OSCs. These results suggest that the DCT unit hold big room for further increasing

and decreasing

loss

of OSCs

via

rational polymer design

which is desirable for application in tandem devices and in-door photovoltaics. Overall

this work demonstrated that DCT is a promising building block for constructing wide bandgap conjugated polymer with deep HOMO level for highly efficient OSCs.

关键词

有机太阳电池共轭聚合物宽带隙给体材料34-二氰基噻吩

Keywords

Organic solar cellsConjugated polymersWide bandgapDonor materials34-Dicyanothiophene

references

Yu G, Gao J, Hummelen J C, Wudi F, Heeger A J. Science , 1995 . 270 ( 5243 ): 1789 - 1791 . DOI:10.1126/science.270.5243.1789http://doi.org/10.1126/science.270.5243.1789 .

Ma W, Yang C, Xiong Gong, Lee K, Heeger A J. Adv Funct Mater , 2005 . 15 ( 10 ): 1617 - 1622 . DOI:10.1002/adfm.200500211http://doi.org/10.1002/adfm.200500211 .

Wang E, Wang L, Lan L, Luo C, Zhuang W, Peng J, Cao Y. App Phys Lett , 2008 . 92 ( 3 ): 033307 DOI:10.1063/1.2836266http://doi.org/10.1063/1.2836266 .

Meng L, Zhang Y, Wan X, Li C, Zhang X, Wang Y, Ke X, Xiao Z, Ding L, Xia R, Yip H L, Cao Y, Chen Y. Science , 2018 . 361 ( 6407 ): 1094 - 1098 . DOI:10.1126/science.aat2612http://doi.org/10.1126/science.aat2612 .

Hou J, Park M-H, Zhang S, Yao Y, Chen L M, Li J H, Yang Y. Macromolecules , 2008 . 41 ( 16 ): 6012 - 6018 . DOI:10.1021/ma800820rhttp://doi.org/10.1021/ma800820r .

Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J. Chem Rev , 2016 . 116 ( 12 ): 7397 - 7457 . DOI:10.1021/acs.chemrev.6b00176http://doi.org/10.1021/acs.chemrev.6b00176 .

Zhou H, Yang L, Stuart A C, Price S C, Liu S, You W. Angew Chem Int Ed , 2011 . 50 ( 13 ): 2995 - 2998 . DOI:10.1002/anie.201005451http://doi.org/10.1002/anie.201005451 .

Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat Commun , 2014 . 5 5293 DOI:10.1038/ncomms6293http://doi.org/10.1038/ncomms6293 .

Wang M, Hu X, Liu P, Li W, Gong X, Huang F, Cao Y. J Am Chem Soc , 2011 . 133 ( 25 ): 9638 - 9641 . DOI:10.1021/ja201131hhttp://doi.org/10.1021/ja201131h .

Wienk M M, Turbiez M, Gilot J, Janssen R A J. Adv Mater , 2008 . 20 ( 13 ): 2556 - 2560 . DOI:10.1002/adma.200800456http://doi.org/10.1002/adma.200800456 .

Li W, Hendriks K H, Wienk M M, Janssen R A J. Acc Chem Res , 2016 . 49 ( 1 ): 78 - 85 . DOI:10.1021/acs.accounts.5b00334http://doi.org/10.1021/acs.accounts.5b00334 .

Li Z A, Chueh C C, Jen A K Y. Prog Polym Sci , 2019 . 99 101175 DOI:10.1016/j.progpolymsci.2019.101175http://doi.org/10.1016/j.progpolymsci.2019.101175 .

Cai Y, Huo L, Sun Y. Adv Mater , 2017 . 29 ( 22 ): 1605437 DOI:10.1002/adma.201605437http://doi.org/10.1002/adma.201605437 .

Hu Z, Ying L, Huang F, Cao Y. Sci China Chem , 2017 . 60 ( 5 ): 571 - 582 . DOI:10.1007/s11426-016-0424-9http://doi.org/10.1007/s11426-016-0424-9 .

Huang Fei(黄飞), Bo Zhishan(薄志山), Geng Yanhou(耿延候), Wang Xianhong(王献红), Wang Lixiang(王利祥),Ma Yuguang(马於光), Hou Jianhui(侯剑辉), Hu Wenping(胡文平), Pei Jian(裴坚), Dong Huanli(董焕丽),Wang Shu(王树), Li Zhen(李振), Shuai Zhigang(帅志刚), Li Yongfang(李永舫), Cao Yong(曹镛) . 2019 . 50 ( 10 ): 988 - 1046 . DOI:10.11777/j.issn1000-3304.2019.19110http://doi.org/10.11777/j.issn1000-3304.2019.19110 .

Lin Y, Wang J, Zhang Z G, Bai H, Li Y, Zhu D, Zhan X. Adv Mater , 2015 . 27 ( 7 ): 1170 - 1174 . DOI:10.1002/adma.201404317http://doi.org/10.1002/adma.201404317 .

Zhao W, Li S, Yao H, Zhang S, Zhang Y, Yang B, Hou J. J Am Chem Soc , 2017 . 139 ( 21 ): 7148 - 7151 . DOI:10.1021/jacs.7b02677http://doi.org/10.1021/jacs.7b02677 .

Yuan J, Zhang Y, Zhou L, Zhang G, Yip H L, Lau T K, Lu X, Zhu C, Peng H, Johnson P A, Leclerc M, Cao Y, Ulanski J, Li Y, Zou Y. Joule , 2019 . 3 ( 4 ): 1140 - 1151 . DOI:10.1016/j.joule.2019.01.004http://doi.org/10.1016/j.joule.2019.01.004 .

Dai Shuixing(代水星), Zhan Xiaowei(占肖卫) . 2017 . ( 11 ): 1706 - 1714.

Yan C, Barlow S, Wang Z, Yan H, Jen A K Y, Marder S R, Zhan X. Nat Rev Mater , 2018 . 3 ( 3 ): 18003 DOI:10.1038/natrevmats.2018.3http://doi.org/10.1038/natrevmats.2018.3 .

Hou J, Inganäs O, Friend R H, Gao F. Nat Mater , 2018 . 17 ( 2 ): 119 - 128 . DOI:10.1038/nmat5063http://doi.org/10.1038/nmat5063 .

Zhang G, Zhao J, Chow P C Y, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem Rev , 2018 . 118 ( 7 ): 3447 - 3507 . DOI:10.1021/acs.chemrev.7b00535http://doi.org/10.1021/acs.chemrev.7b00535 .

Wang J, Wang S, Duan C, Colberts F J M, Mai J, Liu X, Jia X, Lu X, Janssen R A J, Huang F, Cao Y. Adv Energy Mater , 2017 . 7 ( 22 ): 1702033 DOI:10.1002/aenm.201702033http://doi.org/10.1002/aenm.201702033 .

Liu X, Du X, Wang J, Duan C, Tang X, Heumueller T, Liu G, Li Y, Wang Z, Wang J, Liu F, Li N, Brabec C J, Huang F, Cao Y. Adv Energy Mater , 2018 . 8 ( 26 ): 1801699 DOI:10.1002/aenm.201801699http://doi.org/10.1002/aenm.201801699 .

Zhang R, Wang J, Liu X, Pang S, Duan C, Huang F, Cao Y. Sci China Chem , 2019 . 62 ( 7 ): 829 - 836 . DOI:10.1007/s11426-018-9429-1http://doi.org/10.1007/s11426-018-9429-1 .

Veldman D, Meskers S C J, Janssen R A J. Adv Funct Mater , 2009 . 19 ( 12 ): 1939 - 1948 . DOI:10.1002/adfm.200900090http://doi.org/10.1002/adfm.200900090 .

Li W, Hendriks K H, Furlan A, Wienk M M, Janssen R A J. J Am Chem Soc , 2015 . 137 ( 6 ): 2231 - 2234 . DOI:10.1021/ja5131897http://doi.org/10.1021/ja5131897 .

Li S, Ye L, Zhao W, Yan H, Yang B, Liu D, Li W, Ade H, Hou J. J Am Chem Soc , 2018 . 140 ( 23 ): 7159 - 7167 . DOI:10.1021/jacs.8b02695http://doi.org/10.1021/jacs.8b02695 .

Liu J, Chen S, Qian D, Gautam B, Yang G, Zhao J, Bergqvist J, Zhang F, Ma W, Ade H, Inganäs O, Gundogdu K, Gao F, Yan H. Nat Energy , 2016 . 1 ( 7 ): 16089 DOI:10.1038/nenergy.2016.89http://doi.org/10.1038/nenergy.2016.89 .

Wang M, Wang H, Ford M, Yuan J, Mai C-K, Fronk S, Bazan G C. J Mater Chem A , 2016 . 4 ( 39 ): 15232 - 15239 . DOI:10.1039/C6TA07120Ahttp://doi.org/10.1039/C6TA07120A .

Vandewal K, Ma Z, Bergqvist J, Tang Z, Wang E, Henriksson P, Tvingstedt K, Andersson M R, Zhang F, Inganäs O. Adv Funct Mater , 2012 . 22 ( 16 ): 3480 - 3490 . DOI:10.1002/adfm.201200608http://doi.org/10.1002/adfm.201200608 .

Zhang L, Deng W, Wu B, Ye L, Sun X, Wang Z, Gao K, Wu H, Duan C, Huang F, Cao Y. ACS Appl Mater Interfaces , 2020 . 1 ( 2 ): 753 - 762.

Liu X, Deng W, Wang J, Zhang R, Zhang S, Galuska L, Pang S, Gu X, Qiao X, Ma D, Wu H, Duan C, Huang F, Cao Y. J Mater Chem C , 2019 . 7 ( 48 ): 15335 - 15343 . DOI:10.1039/C9TC05601Ghttp://doi.org/10.1039/C9TC05601G .

Mei J, Bao Z. Chem Mater , 2013 . 26 ( 1 ): 604 - 615.

Cui C, Li Y. Energy Environ Sci , 2019 . 12 3225 - 3246 . DOI:10.1039/C9EE02531Fhttp://doi.org/10.1039/C9EE02531F .

Xu X, Zhang G, Li Y, Peng Q. Chin Chem Lett , 2019 . 30 ( 4 ): 809 - 825 . DOI:10.1016/j.cclet.2019.02.030http://doi.org/10.1016/j.cclet.2019.02.030 .

Xiong Y, Qiao X, Li H. Polym Chem , 2015 . 6 ( 36 ): 6579 - 6584 . DOI:10.1039/C5PY00804Bhttp://doi.org/10.1039/C5PY00804B .

Sui Y, Deng Y, Han Y, Zhang J, Hu W, Geng Y. J Mater Chem C , 2018 . 6 ( 47 ): 12896 - 12903 . DOI:10.1039/C8TC03725Fhttp://doi.org/10.1039/C8TC03725F .

Liao S F, Chen C T, Chao C Y. ACS Macro Lett , 2017 . 6 ( 9 ): 969 - 974 . DOI:10.1021/acsmacrolett.7b00547http://doi.org/10.1021/acsmacrolett.7b00547 .

Huang J, Tang Y, Gao K, Liu F, Guo H, Russell T P, Yang T, Liang Y, Cheng X, Guo X. Macromolecules , 2016 . 50 ( 1 ): 137 - 150.

Kim H G, Kim M, Clement J A, Lee J, Shin J, Hwang H, Sin D H, Cho K. Chem Mater , 2015 . 27 ( 19 ): 6858 - 6868 . DOI:10.1021/acs.chemmater.5b03256http://doi.org/10.1021/acs.chemmater.5b03256 .

Seri M, Bolognesi M, Chen Z, Lu S, Koopman W, Facchetti A, Muccini M. Macromolecules , 2013 . 46 ( 16 ): 6419 - 6430 . DOI:10.1021/ma4011186http://doi.org/10.1021/ma4011186 .

Wang Y, Hasegawa T, Matsumoto H, Mori T, Michinobu T. Adv Funct Mater , 2017 . 27 ( 2 ): 1604608 DOI:10.1002/adfm.201604608http://doi.org/10.1002/adfm.201604608 .

Balandier J Y, Quist F, Amato C, Bouzakraoui S, Cornil J, Sergeyev S, Geerts Y. Tetrahedron , 2010 . 66 ( 49 ): 9560 - 9572 . DOI:10.1016/j.tet.2010.09.086http://doi.org/10.1016/j.tet.2010.09.086 .

Cardona C M, Li W, Kaifer A E, Stockdale D, Bazan G C. Adv Mater , 2011 . 23 ( 20 ): 2367 - 2371 . DOI:10.1002/adma.201004554http://doi.org/10.1002/adma.201004554 .

Feng K, Yuan J, Bi Z, Ma W, Xu X, Zhang G, Peng Q. iScience , 2019 . 12 1 - 12 . DOI:10.1016/j.isci.2018.12.027http://doi.org/10.1016/j.isci.2018.12.027 .

Du Z, Bao X, Li Y, Liu D, Wang J, Yang C, Wimmer R, Städe L W, Yang R, Yu D. Adv Energy Mater , 2018 . 8 ( 8 ): 1701471 DOI:10.1002/aenm.201701471http://doi.org/10.1002/aenm.201701471 .

Chen S, Liu Y, Zhang L, Chow P C Y, Wang Z, Zhang G, Ma W, Yan H. J Am Chem Soc , 2017 . 139 ( 18 ): 6298 - 6301 . DOI:10.1021/jacs.7b01606http://doi.org/10.1021/jacs.7b01606 .

Yao H, Qian D, Zhang H, Qin Y, Xu B, Cui Y, Yu R, Gao F, Hou J. Chinese J Chem , 2018 . 36 ( 6 ): 491 - 494 . DOI:10.1002/cjoc.201800015http://doi.org/10.1002/cjoc.201800015 .

Yao H, Cui Y, Qian D, Ponseca C S, J r., Honarfar A, Xu Y, Xin J, Chen Z, Hong L, Gao B, Yu R, Zu Y, Ma W, Chabera P, Pullerits T, Yartsev A, Gao F, Hou J.. J Am Chem Soc , 2019 . 141 ( 19 ): 7743 - 7750 . DOI:10.1021/jacs.8b12937http://doi.org/10.1021/jacs.8b12937 .

Zhang S, Qin Y, Zhu J, Hou J. Adv Mater , 2018 . 30 ( 20 ): 1800868 DOI:10.1002/adma.201800868http://doi.org/10.1002/adma.201800868 .

Li W, Ye L, Li S, Yao H, Ade H, Hou J. Adv Mater , 2018 . 30 ( 16 ): 1707170 DOI:10.1002/adma.201707170http://doi.org/10.1002/adma.201707170 .

Su W, Li G, Fan Q, Zhu Q, Guo X, Chen J, Wu J, Ma W, Zhang M, Li Y. J Mater Chem A , 2019 . 7 ( 5 ): 2351 - 2359 . DOI:10.1039/C8TA10662Bhttp://doi.org/10.1039/C8TA10662B .

Fan B, Du X, Liu F, Zhong W, Ying L, Xie R, Tang X, An K, Xin J, Li N, Ma W, Brabec C J, Huang F, Cao Y. Nat Energy , 2018 . 3 ( 12 ): 1051 - 1058 . DOI:10.1038/s41560-018-0263-4http://doi.org/10.1038/s41560-018-0263-4 .

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