Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3, 2-b:2', 3'-d]pyrrole-based Conjugated Copolymers

Jing Ren; Wei-ye Chen; Feng Li; Wei Wang; Ren-qiang Yang; Ming-liang Sun

doi:10.11777/j.issn1000-3304.2017.17124

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Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3, 2-b:2', 3'-d]pyrrole-based Conjugated Copolymers

Research Article | 更新时间：2021-01-26

- Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3, 2-b:2', 3'-d]pyrrole-based Conjugated Copolymers
- Acta Polymerica Sinica Issue 4, Pages: 456-463(2018)
- 作者机构：
  
  1.中国海洋大学材料科学与工程学院青岛 266100
  2.中国科学院青岛生物能源与过程研究所青岛 266101
  3.青岛科技大学高分子科学与工程学院青岛 266042
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2017.17124
  CLC：
- Published：20 April 2018，
  
  Received：7 May 2017，
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Jing Ren, Wei-ye Chen, Feng Li, Wei Wang, Ren-qiang Yang, Ming-liang Sun. Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3, 2-b:2', 3'-d]pyrrole-based Conjugated Copolymers. [J]. Acta Polymerica Sinica (4):456-463(2018)
DOI：

Jing Ren, Wei-ye Chen, Feng Li, Wei Wang, Ren-qiang Yang, Ming-liang Sun. Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3, 2-b:2', 3'-d]pyrrole-based Conjugated Copolymers. [J]. Acta Polymerica Sinica (4):456-463(2018) DOI： 10.11777/j.issn1000-3304.2017.17124.

摘要

二噻吩[3，2-b：2'，3'-d]并吡咯（Dithieno[3，2-b：2'，3'-d]

pyrrole，DTP）分别与3种受体单元聚合得到聚合物

，受体单元分别为：吡咯并吡咯二酮（DPP）、二噻吩苯并噁二唑（DTBO）和喹喔啉衍生物（TQ）.研究表明，3种聚合物都有较窄的带隙（

：1.23 eV，

：1.51 eV，

：1.50 eV），有利于活性层材料对太阳光的吸收，其中

获得了最宽的吸收（近1000 nm）.将

与PC

BM共混制备光伏器件，当给受体比例为1：3时，基于

的光伏器件短路电流密度（short-circuit current density，

）为15.82 mA/cm

，开路电压（open-circuit voltage，

）为0.38 V，能量转化效率（power conversion efficiency，PCE）达到3.33%，为3种聚合物中最高的效率.对于聚合物

和

，在给受体比例为1：2时，光伏性能最好，此时

与

的PCE值分别为1.20%和1.37%，导致较低光电转换效率的因素是短路电流密度

（

：9.70 mA/cm

，

：9.21 mA/cm

）和开路电压

（约0.3 V）过低.

Abstract

In the polymer solar cells research field

dithieno[3

2-b:2'

3'-d]pyrrole (DTP) is a good donor unit due to its good planarity when it is used as build donor-acceptor (D-A) polymer. In this work

three DTP based polymers (named

) are synthesized by polymerizing DTP with DPP

DTBO and TQ co-monomer acceptor unit

respectively. These three polymers exhibit good solubility in common solvent such as dichlorobenzene. GPC results show that the polymers show moderate number-average molecular weights (

9×10

to 2.2×10

) and narrow PDI (1-2). UV-Vis absorption spectra in solution and thin film show that the polymers have a relatively narrow band gap (

:1.23 eV;

:1.51 eV;

:1.50 eV)

which enhances the polymer absorption of sunlight

with

showing the widest absorption (extending UV-Vis absorption to nearly 1000 nm). The thermal property of these polymers is measured by thermogravimetric analysis (TGA)

giving their

located at 313-410℃. The highest occupied molecular orbital (HOMO) energy levels of the polymers are between -5.2 eV and -5.4 eV

as tested by CV method. Photovoltaic devices are fabricated with

as donor and PC

BM as acceptor in active layer. The solar cells

test results reveal that

has the highest PCE of 3.33% with

of 15.82 mA/cm

of 0.38 V when the mass ratio of

to PC

BM is kept at 1:3. The relative high PCE of

based PSCs devices is due to the wide light absorption

leading to high

of PSCs devices

which also can be confirmed by external quatum efficiency (EQE) test. For the polymers

and

with the mass ratio of polymer/PC

BM at 1:2

PCE of 1.20% for

and 1.37% of

are achieved respectively

and the relatively low PCE is caused by low short circuit current density (

) (

:9.70 mA/cm

:9.21 mA/cm

) and the low open-circuit voltage (

only around 0.3 V). Transmission electron microscopy is also used to explore the polymer solar cells active layer morphology

which correlates closely with the donor and the acceptor aggregations and the phase separation.

关键词

二噻吩[3 2-b:2' 3'-d]并吡咯共轭聚合物光伏材料聚合物太阳能电池

Keywords

Dithieno[3 2-b:2' 3'-d]pyrroleConjugated polymerPhotovoltaic materialPolymer solar cells

references

Z He , C Zhong , S Su , M Xu , H Wu , Y Cao . Nat Photonics , 2012 . 6 ( 9 ): 591 - 595 . DOI:10.1038/nphoton.2012.190http://doi.org/10.1038/nphoton.2012.190.

L Ye , S Zhang , W Zhao , H Yao , J Hou . Chem Mater , 2014 . 26 ( 12 ): 3603 - 3605 . DOI:10.1021/cm501513nhttp://doi.org/10.1021/cm501513n.

S Zhang , L Ye , W Zhao , D Liu , H Yao , J Hou . Macromolecules , 2014 . 47 ( 14 ): 4653 - 4659 . DOI:10.1021/ma500829rhttp://doi.org/10.1021/ma500829r.

S H Liao , H J Jhuo , Y S Cheng , S A Chen . Adv Mater , 2013 . 25 ( 34 ): 4766 - 4771 . DOI:10.1002/adma.v25.34http://doi.org/10.1002/adma.v25.34.

Huifeng Yao , Jianhui Hou . Acta Polymerica Sinica , 2016 . ( 11 ): 1468 - 1481 . http://www.gfzxb.org/article/doi/10.11777/j.issn1000-3304.2016.16216.

姚惠峰 , 侯剑辉 . 高分子学报 , 2016 . ( 11 ): 1468 - 1481 . http://www.gfzxb.org/article/doi/10.11777/j.issn1000-3304.2016.16216.

Yong Cui , Huifeng Yao , Chenyi Yang , Shaoqing Zhang , Jianhui Hou . Acta Polymerica Sinica , 2018 . ( 2 ): 223 - 230 . http://www.gfzxb.org/article/doi/10.11777/j.issn1000-3304.2018.17297.

崔勇 , 姚惠峰 , 杨晨熠 , 张少青 , 侯剑辉 . 高分子学报 , 2018 . ( 2 ): 223 - 230 . http://www.gfzxb.org/article/doi/10.11777/j.issn1000-3304.2018.17297.

L Yang , H Zhou , W J You . Phys Chem C , 2010 . 114 ( 39 ): 16793 - 16800 . DOI:10.1021/jp106640rhttp://doi.org/10.1021/jp106640r.

W Lee , H Choi , S Hwang , J Y Kim , H Y Woo . Chemistry , 2012 . 18 ( 9 ): 2551 - 2558 . DOI:10.1002/chem.201102883http://doi.org/10.1002/chem.201102883.

Y Li . Acc Chem Res , 2012 . 45 ( 5 ): 723 - 733 . DOI:10.1021/ar2002446http://doi.org/10.1021/ar2002446.

Q Peng , X Liu , D Su , G Fu , J Xu , L Dai . Adv Mater , 2011 . 23 ( 39 ): 4554 - 4558 . DOI:10.1002/adma.201101933http://doi.org/10.1002/adma.201101933.

W Li , W S Roelofs , M M Wienk , R A Janssen . J Am Chem Soc , 2012 . 134 ( 33 ): 13787 - 13795 . DOI:10.1021/ja305358zhttp://doi.org/10.1021/ja305358z.

L Dou , W H Chang , J Gao , C C Chen , J You , Y Yang . Adv Mater , 2013 . 25 ( 6 ): 825 - 831 . DOI:10.1002/adma.v25.6http://doi.org/10.1002/adma.v25.6.

S A Jenekhe , L Lu , M M Alam . Macromolecules , 2001 . 34 ( 21 ): 7315 - 7324 . DOI:10.1021/ma0100448http://doi.org/10.1021/ma0100448.

X Xu , Y Wu , J Fang , Z Li , Z Wang , Y Li , Q Peng . Chem-Eur J , 2014 . 20 ( 41 ): 13259 - 13271 . DOI:10.1002/chem.201403153http://doi.org/10.1002/chem.201403153.

M Wang , H Wang , T Yokoyama , X Liu , Y Huang , Y Zhang , T Q Nguyen , S Aramaki , G C Bazan . J Am Chem Soc , 2014 . 136 ( 36 ): 12576 - 12579 . DOI:10.1021/ja506785whttp://doi.org/10.1021/ja506785w.

W C Zhao , L Ye , S Q Zhang , H F Yao , M L Sun , J H Hou . J Phys Chem C , 2015 . 119 27322 - 27329 . DOI:10.1021/acs.jpcc.5b09575http://doi.org/10.1021/acs.jpcc.5b09575.

W C Zhao , L Ye , S Q Zhang , B Fan , M L Sun , J H Hou . Sci Rep , 2014 . 47 4653 - 4660 . http://www.ncbi.nlm.nih.gov/pubmed/25300365.

K Zhao , L Ye , W C Zhao , S Q Zhang , H F Yao , B W Xu , M L Sun , J H Hou . J Mater Chem C , 2015 . 3 9565 - 9571 . http://dx.doi.org/10.1039/C5TC02172C.

J Z Ren , X C Bao , L L Han , J X Wang , M Qiu , Q Q Zhu , T Hu , R Y Sheng , M L Sun , R Q Yang . Polym Chem , 2015 . 6 4415 - 4423 . DOI:10.1039/C5PY00199Dhttp://doi.org/10.1039/C5PY00199D.

R Y Sheng , Q Liu , M J Xiao , C Y Gu , T Hu , J Z Ren , M L Sun , R Q Yang . Polym Chem , 2015 . 53 1558 - 1566 . DOI:10.1002/pola.v53.13http://doi.org/10.1002/pola.v53.13.

Q Liu , X C Bao , Y Yan , Z K Du , V A L Roy , D Q Zhu , M L Sun , C S Lee , R Q Yang . J Mater Sci , 2015 . 50 2263 - 2271 . DOI:10.1007/s10853-014-8789-8http://doi.org/10.1007/s10853-014-8789-8.

Q Liu , X C Bao , L L Han , C T Gu , M Qiu , Z K Du , R Y Sheng , M L Sun , R Q Yang . Sol Energ Mat Sol C , 2015 . 138 26 - 34 . DOI:10.1016/j.solmat.2015.02.022http://doi.org/10.1016/j.solmat.2015.02.022.

D Y Liu , C Y Gu , M J Xiao , M Qiu , M L Sun , R Q Yang . Polym Chem , 2015 . 6 3398 - 3406 . DOI:10.1039/C5PY00117Jhttp://doi.org/10.1039/C5PY00117J.

T Hu , L L Han , M J Xiao , X C Bao , T Wang , M L Sun , R Q Yang . J Mater Chem C , 2014 . 2 8047 - 8053 . DOI:10.1039/C4TC01440Ehttp://doi.org/10.1039/C4TC01440E.

J X Wang , M J Xiao , W C Chen , M Qiu , Z K Du , W G Zhu , S G Wen , N Wang , R Q Yang . Macromolecules , 2014 . 47 7823 - 7830 . DOI:10.1021/ma501756phttp://doi.org/10.1021/ma501756p.

Mingliang Sun , Li Wang , Yangjun Xia , Bin Du , Ransheng Liu , Yong Cao . Acta Polymerica Sinica , 2007 . ( 10 ): 952 - 958 . http://kns.cnki.net/KCMS/detail/detail.aspx?filename=gfxb200710010&dbname=CJFD&dbcode=CJFQ.

孙明亮 , 王藜 , 夏养君 , 杜斌 , 刘然升 , 曹镛 . 高分子学报 , 2007 . ( 10 ): 952 - 958 . http://kns.cnki.net/KCMS/detail/detail.aspx?filename=gfxb200710010&dbname=CJFD&dbcode=CJFQ.

E J Zhou , S Yamakawa , K Tajima , C H Yang , K Hashimoto . Chem Mater , 2009 . 21 4055 - 4061 . DOI:10.1021/cm901487fhttp://doi.org/10.1021/cm901487f.

E J Zhou , K Tajima , C H Yang , K Hashimoto . J Mater Chem , 2010 . 20 2362 - 2368 . DOI:10.1039/b923452ghttp://doi.org/10.1039/b923452g.

E J Zhou , J Z Cong , K Tajima , C H Yang , K Hashimoto . J Phys Chem C , 2012 . 116 2608 - 2614 . DOI:10.1021/jp209253mhttp://doi.org/10.1021/jp209253m.

C Gong , H B Yang , Q L Song , Z S Lu , C M Li . Sol Energ Mat Sol C , 2011 . 95 969 - 973 . DOI:10.1016/j.solmat.2010.11.034http://doi.org/10.1016/j.solmat.2010.11.034.

B Burkhart , P P Khlyabich , B C Thompson . J Photon Energy , 2012 . 2 021002(1-14) http://www.mendeley.com/research/solar-cells-based-semirandom-p3ht-analogues-containing-dithienopyrrole-influence-incorporating-stron/.

M J Zhang , H J Fan , X Guo , Y J He , Z G Zhang , J Min , J Zhang , G J Zhao , X W Zhan , Y F Li . Macromolecules , 2010 . 43 5706 - 5712 . DOI:10.1021/ma100767bhttp://doi.org/10.1021/ma100767b.

E J Zhou , J Z Cong , K Tajima , C H Yang , K Hashimoto . Macromol Chem Phys , 2011 . 212 305 - 310 . DOI:10.1002/macp.201000584http://doi.org/10.1002/macp.201000584.

X L Hu , M M Shi , L J Zuo , Y X Nan , Y J Liu , L Fu , H Z Chen . Polymer , 2011 . 52 2559 - 2564 . DOI:10.1016/j.polymer.2011.03.057http://doi.org/10.1016/j.polymer.2011.03.057.

Y F Geng , J Z Cong , K Tajima , Q D Zenga , E J Zhou . Polym Chem , 2014 . 5 6797 - 6803 . DOI:10.1039/C4PY00975Dhttp://doi.org/10.1039/C4PY00975D.

Y Qiao , Y Guo , C Yu , F Zhang , W Xu , Y Liu , D Zhu . J Am Chem Soc , 2012 . 134 4084 - 4087 . DOI:10.1021/ja3003183http://doi.org/10.1021/ja3003183.

X Guo , A Facchetti , T J Marks . Chem Rev , 2014 . 114 8943 - 9021 . DOI:10.1021/cr500225dhttp://doi.org/10.1021/cr500225d.

C J Brabec , A Cravino , D Meissner , N S Sariciftci , T Fromherz , M T Rispens , L Sanchez , J C Hummelen . Adv Funct Mater , 2001 . 11 374 - 380 . DOI:10.1002/(ISSN)1616-3028http://doi.org/10.1002/(ISSN)1616-3028.

M D Perez , C Borek , S R Forrest , M E Thompson . J Am Chem Soc , 2009 . 131 9281 - 9286 . DOI:10.1021/ja9007722http://doi.org/10.1021/ja9007722.

W J Potscavage , A Sharma , B Kippelen . Acc Chem Res , 2009 . 42 1758 - 1767 . DOI:10.1021/ar900139vhttp://doi.org/10.1021/ar900139v.

A Maurano , R Hamilton , C G Shuttle , A M Ballantyne , J Nelson , B O'Regan , W M Zhang , I McCulloch , H Azimi , M Morana , C J Brabec , J R Durrant . Adv Mater , 2010 . 22 4987 - 4992 . DOI:10.1002/adma.v22.44http://doi.org/10.1002/adma.v22.44.

H J Snaith , N C Greenham , R H Friend . Adv Mater , 2004 . 16 1640 - 1645 . DOI:10.1002/(ISSN)1521-4095http://doi.org/10.1002/(ISSN)1521-4095.

J Liu , Y J Shi , Y Yang . Adv Funct Mater , 2001 . 11 420 - 424 . DOI:10.1002/1616-3028(200112)11:6<420::AID-ADFM420>3.0.CO;2-Khttp://doi.org/10.1002/1616-3028(200112)11:6<420::AID-ADFM420>3.0.CO;2-K.

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