Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells

Bo Zhang; Yong-gao Yu; Zhi-tian Liu; Xi Liu; Chun-hui Duan; Fei Huang

doi:10.11777/j.issn1000-3304.2020.20011

您当前的位置：

首页 >

文章列表页 >

Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells

更新时间：2021-01-26

- Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells
- Acta Polymerica Sinica Vol. 51, Issue 6, Pages: 620-631(2020)
- 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：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2020.20011
  CLC：
- Published：2020-6，
  
  Published Online：17 April 2020，
  
  Received：27 January 2020，
  
  Revised：5 March 2020，
扫描看全文
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 51(6):620-631(2020)
DOI：

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 51(6):620-631(2020) 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 .

更多指标>

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

New Thin-film Solar Cells: Flexible Design and Printing Manufacturing

Recent Progress of Conjugated Polymers Containing Quinoidal Structure

Research Progress on Aggregation Structure of Conjugated Polymers in Multicomponent Blends

Direct Arylation Polycondensation Synthesis of High Mobility Conjugated Polymers

Related Author

No data

Related Institution

Institute of Chemistry, Chinese Academy of Sciences

College of Chemistry and Chemical Engineering/Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University

College of Chemistry and Chemical Engineering/Institute of Polymers and Energy Chemistry, Nanchang University

School of Materials Science and Engineering, Tianjin University

State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

Postal code：100190
Tel：010-62588927 Email：gfzxb@iccas.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备05002797号-8 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰