Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells

Shi-fan Wang; Ya-nan Liu; Jie Yang; You-tian Tao; Yan Guo; Xu-dong Cao; Zhi-guo Zhang; Yong-fang Li; Wei Huang

doi:10.1007/s10118-017-1889-6

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Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells

Papers | Updated：2021-02-18

- Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells
- Chinese Journal of Polymer Science Vol. 35, Issue 2, Pages: 207-218(2017)
- Affiliations：
  
  a.Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University (Nanjing Tech), Nanjing 211816, China
  b.Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  c.Department of Biomedical Engineering, College of Engineering and Applied Sciences, Nanjing 210093, China
- Author bio：
  
  You-tian Tao (陶友田), E-mail:iamyttao@njtech.edu.cn
  Zhi-guo Zhang (张志国), E-mail:zgzhangwhu@iccas.ac.cn
  Wei Huang (黄维), E-mail:iamwhuang@njtech.edu.cn
- Funds：
- DOI：10.1007/s10118-017-1889-6
  CLC：
- Received：18 July 2016，
  
  Revised：2016-8-14，
  
  Accepted：15 August 2016，
  
  Published：2017-02
- Accepted：
Scan QR Code
Shi-fan Wang, Ya-nan Liu, Jie Yang, et al. Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells[J]. Chinese Journal of Polymer Science, 2017, 35(2): 207-218.
DOI：

Shi-fan Wang, Ya-nan Liu, Jie Yang, et al. Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells[J]. Chinese Journal of Polymer Science, 2017, 35(2): 207-218. DOI： 10.1007/s10118-017-1889-6.

摘要

Abstract

Donor-acceptor (D-A) type fully conjugated block copolymer systems have been rarely reported due to the challenges in synthetic approaches to prepare well-defined low-polydispersity products. In this work

fully conjugated block copolymers are synthesized in a one-pot reaction through Stille coupling polycondensation

by utilizing the end-functional polymer copolymerization method. End-functional P3HT are copolymerized with AA (2

7-dibromo-9-(heptadecan-9-yl)-9

-carbazole) and BB (4

7-bis (5-(trimethylstannyl) thiophen-2-yl) benzo[c] [1

thiadiazole

TBT) type monomers

respectively. The orthogonal solubility between the very soluble P3HT donor and the insoluble PCDTBT acceptor block improves the purity of block copolymers as well as distinct nano-scale phase-separation compared with other reports on miscibility of donor and acceptor polymer block. Further purification

via

preparative GPC is carried out to remove the excess of unreacted P3HT and free PCDTBT as well as to achieve low polydispersity of block copolymers. The chemical structure of the P3HT-

-PCDTBT block copolymers are verified

via

H-NMR

and further confirmed by FTIR spectra. The block copolymer shows broad absorption and moderate optical band gap of 1.8 eV. Furthermore

the fully conjugated block copolymer films exhibit significant fine structures

much smoother film morphology compared to P3HT/PCDTBT polymer blends. By adding a small amount of block copolymer P3HT-

-PCDTBT as a compatibilizer into the bulk-heterojunction of P3HT:PC

BM blends

polymer solar cells with an 8% increase of short circuit current (

) and 10% increase of power conversion efficiency (PCE) are achieved owing to the improvement of the active-layer film morphology. To the best of our knowledge

this is the first report on donor-acceptor type fully conjugated block copolymer as an effective ternary additive in polymer:fullerene bulk heterojunction solar cells.

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references

G. Yu , J. Gao , J.C. Hummelen , F. Wudl , A.J. Heeger . Science , 1995 . 270 1789 DOI: 10.1126/science.270.5243.1789 http://doi.org/10.1126/science.270.5243.1789 .

J.J. M.Halls , C.A. Walsh , N.C. Greenham , E.A. Marseglia , R.H. Friend , S.C. Moratti , A.B. Holmes . Nature , 1995 . 376 498 DOI: 10.1038/376498a0 http://doi.org/10.1038/376498a0 .

J. You , L. Dou , K. Yoshimura , T. Kato , K. Ohya , T. Moriarty , K. Emery , C.C. Chen , J. Gao , G. Li , Y. Yang . Nat. Commun. , 2013 . 4 1446 DOI: 10.1038/ncomms2411 http://doi.org/10.1038/ncomms2411 .

Z. He , C. Zhong , S. Su , M. Xu , H. Wu , Y. Cao . Nat. Photon. , 2012 . 6 593 DOI: 10.1038/nphoton.2012.190 http://doi.org/10.1038/nphoton.2012.190 .

M.L. Keshtov , D.V. Marochkin , Y. Fu , Z. Xie , Y. Geng , V.S. Kochurov , A.R. Khokhlov . Chinese J. Polym. Sci. , 2014 . 32 844 DOI: 10.1007/s10118-014-1458-1 http://doi.org/10.1007/s10118-014-1458-1 .

M. Qian , R. Zhang , J. Hao , W. Zhang , Q. Zhang , J. Wang , Y. Tao , S. Chen , J. Fang , W. Huang . Adv. Mater. , 2015 . 27 3546 DOI: 10.1002/adma.v27.23 http://doi.org/10.1002/adma.v27.23 .

S. Wang , J. Yang , Z. Zhang , Y. Hu , X. Cao , H. Li , Y. Tao , Y. Li , W. Huang . RSC Adv. , 2015 . 5 68192 DOI: 10.1039/C5RA07383A http://doi.org/10.1039/C5RA07383A .

J.E. Slota , X. He , W.T.S. Huck . Nano Today , 2010 . 5 231 DOI: 10.1016/j.nantod.2010.05.004 http://doi.org/10.1016/j.nantod.2010.05.004 .

I. Etxebarria , J. Ajuria , R. Pacios . Org. Electron. , 2015 . 19 34 DOI: 10.1016/j.orgel.2015.01.014 http://doi.org/10.1016/j.orgel.2015.01.014 .

S. Chan , C. Lai , H. Chen , C. Ting , C.P. Chen . Macromolecules , 2011 . 44 8886 DOI: 10.1021/ma201425d http://doi.org/10.1021/ma201425d .

M.K. Riede , K.O. Sylvester-Hvid , M. Glatthaar , N. Keegan , T. Ziegler , B. Zimmermann , M. Niggemann , A.W. Liehr , G. Willeke , A. Gombert . Prog. Photovolt:Res. Appl. , 2008 . 16 561 DOI: 10.1002/pip.v16:7 http://doi.org/10.1002/pip.v16:7 .

R.C. Mulherin , S. Jung , S. Huettner , K. Johnson , P. Kohn , M. Sommer , S. Allard , U. Scherf , N.C. Greenham . Nano Lett. , 2011 . 11 4846 DOI: 10.1021/nl202691n http://doi.org/10.1021/nl202691n .

L. Chang , H.W.A. Lademann , J.B. Bonekamp , K. Meerholz , A.J. Moulé . Adv. Funct. Mater. , 2011 . 21 1779 DOI: 10.1002/adfm.201002372 http://doi.org/10.1002/adfm.201002372 .

E. Pavlopoulou , C.S. Kim , S.S. Lee , Z. Chen , A. Facchetti , M.F. Toney , Y. Loo . Chem. Mater. , 2014 . 26 5020 DOI: 10.1021/cm502112z http://doi.org/10.1021/cm502112z .

S.J. Lou , J.M. Szarko , T. Xu , L. Yu , T.J. Marks , L.X. Chen . J. Am. Chem. Soc. , 2011 . 133 20661 DOI: 10.1021/ja2085564 http://doi.org/10.1021/ja2085564 .

F. Padinger , R.S. Rittberger , N.S. Sariciftci . Adv. Funct. Mater. , 2003 . 13 85 DOI: 10.1002/adfm.200390011 http://doi.org/10.1002/adfm.200390011 .

A. Saeki , S. Yoshikawa , M. Tsuji , Y. Koizumi , M. Ide , C. Vijayakumar , S. Seki . J. Am. Chem. Soc. , 2012 . 134 19035 DOI: 10.1021/ja309524f http://doi.org/10.1021/ja309524f .

M.J. Robb , S. Ku , C.J. Hawker . Adv. Mater. , 2013 . 25 5686 DOI: 10.1002/adma.v25.40 http://doi.org/10.1002/adma.v25.40 .

Lai, Y., Ohshimizu, K., Takahashi, A., Hsu, J., Higashihara, T., Ueda, M. And Chen, W., J. Polym. Sci., Part A:Polym. Chem., 2011, 49:2577

J. Wang , T. Higashihara . Polym. Chem. , 2013 . 4 5518 DOI: 10.1039/c3py00979c http://doi.org/10.1039/c3py00979c .

U. Scherf , A. Gutacker , N. Koenen . Acc. Chem. Res. , 2008 . 41 1086 DOI: 10.1021/ar7002539 http://doi.org/10.1021/ar7002539 .

Y. Lee , E.D. Gomez . Macromolecules , 2015 . 48 7385 DOI: 10.1021/acs.macromol.5b00112 http://doi.org/10.1021/acs.macromol.5b00112 .

S. Wang , Y. Guo , J. Yang , Y. Tao , W. Huang . Chin. J. Chem. , 2015 . 33 865 DOI: 10.1002/cjoc.201500257 http://doi.org/10.1002/cjoc.201500257 .

S.Y. Ku , M.A. Brady , N.D. Treat , J.E. Cochran , M.J. Robb , E.J. Kramer , M.L. Chabinyc , C.J. Hawker . J. Am. Chem. Soc. , 2012 . 134 16040 DOI: 10.1021/ja307431k http://doi.org/10.1021/ja307431k .

C. Guo , Y.H. Lin , M.D. Witman , K.A. Smith , C. Wang , A. Hexemer , J. Strzalka , E.D. Gomez , R. Verduzco . Nano Lett. , 2013 . 13 2957 DOI: 10.1021/nl401420s http://doi.org/10.1021/nl401420s .

A. Bolag , H. Hayashi , P. Charbonnaz , N. Sakai , S. Matile . Chemistry Open , 2013 . 2 55 .

L. Jea Uk , J. Jae Woong , E. Todd , P.R. Thomas , J. Won Ho . Nanotechnology , 2010 . 21 105201 DOI: 10.1088/0957-4484/21/10/105201 http://doi.org/10.1088/0957-4484/21/10/105201 .

S. Rajaram , P.B. Armstrong , B.J. Kim , J.M.J. Fréchet . Chem. Mater. , 2009 . 21 1775 DOI: 10.1021/cm900911x http://doi.org/10.1021/cm900911x .

S. Wang , Q. Yang , Y. Tao , Y. Guo , J. Yang , Y. Liu , L. Zhao , Z. Xie , W. Huang . New J. Chem. , 2016 . 40 1825 DOI: 10.1039/C5NJ02636A http://doi.org/10.1039/C5NJ02636A .

W. Mok , Y. Lin , K.G. Yager , A.D. Mohite , W. Nie , S.B. Darling , Y. Lee , E. Gomez , D. Gosztola , R.D. Schaller , R. Verduzco . Adv. Funct. Mater. , 2015 . 25 5578 DOI: 10.1002/adfm.201502623 http://doi.org/10.1002/adfm.201502623 .

K. Nakabayashi , H. Mori . Macromolecules , 2012 . 45 9618 DOI: 10.1021/ma302170e http://doi.org/10.1021/ma302170e .

Y.H. Lin , K.A. Smith , C.N. Kempf , R. Verduzco . Polym. Chem. , 2013 . 4 229 DOI: 10.1039/C2PY20830J http://doi.org/10.1039/C2PY20830J .

L.J. Bu , X.Y. Guo , B. Yu , Y. Qu , Z.Y. Xie , D.H. Yan , Y.H. Geng , F.S. Wang . J. Am. Chem. Soc. , 2009 . 131 13242 DOI: 10.1021/ja905980w http://doi.org/10.1021/ja905980w .

D. Gao , J. Hollinger , D.S. Seferos . ACS Nano , 2012 . 6 7114 DOI: 10.1021/nn3021844 http://doi.org/10.1021/nn3021844 .

L.M. Kozycz , D. Gao , J. Hollinger , D.S. Seferos . Macromolecules , 2012 . 45 5823 DOI: 10.1021/ma3009349 http://doi.org/10.1021/ma3009349 .

J. Hollinger , J. Sun , D. Gao , D. Karl , D.S. Seferos . Macromol. Rapid Commun. , 2013 . 34 437 DOI: 10.1002/marc.v34.5 http://doi.org/10.1002/marc.v34.5 .

C. Chi , M. Chen , D. Liaw , H. Wu , Y. Huang , Y. Tai . ACS Appl. Mater. Inter. , 2014 . 6 12119 DOI: 10.1021/am501209t http://doi.org/10.1021/am501209t .

J.F. Qu , B.R. Gao , H.K. Tian , X.J. Zhang , Y. Wang , Z.Y. Xie , H.Y. Wang , Y.H. Geng , F.S. Wang . J. Mater. Chem. A , 2014 . 2 3632 DOI: 10.1039/c3ta14701k http://doi.org/10.1039/c3ta14701k .

F. Lombeck , H. Komber , A.R. Sepe , H. Friend , M. Sommer . Macromolecules , 2015 . 48 7851 DOI: 10.1021/acs.macromol.5b01845 http://doi.org/10.1021/acs.macromol.5b01845 .

A. Salleo , R.J. Kline , D.M. DeLongchamp , M.L. Chabinyc . Adv. Mater. , 2010 . 22 3812 DOI: 10.1002/adma.200903712 http://doi.org/10.1002/adma.200903712 .

H. Sirringhaus , N. Tessler , R.H. Friend . Science , 1998 . 280 1741 DOI: 10.1126/science.280.5370.1741 http://doi.org/10.1126/science.280.5370.1741 .

D.T. Duong , H. Phan , D. Hanifi , P.S. Jo , T.Q. Nguyen , A. Salleo . Adv. Mater. , 2014 . 26 6069 DOI: 10.1002/adma.201402015 http://doi.org/10.1002/adma.201402015 .

N. Blouin , A. Michaud , M. Leclerc . Adv. Mater. , 2007 . 19 2295 DOI: 10.1002/(ISSN)1521-4095 http://doi.org/10.1002/(ISSN)1521-4095 .

Z. He , C. Zhong , X. Huang , W.Y. Wong , H. Wu , L. Chen , S. Su , Y. Cao . Adv. Mater. , 2011 . 23 4636 DOI: 10.1002/adma.201103006 http://doi.org/10.1002/adma.201103006 .

R.S. Ashraf , B.C. Schroeder , H.A. Bronstein , Z. Huang , S. Thomas , R.J. Kline , C.J. Brabec , P. Rannou , T.D. Anthopoulos , J.R. Durrant , I. McCulloch . Adv. Mater. , 2013 . 25 2029 DOI: 10.1002/adma.201300027 http://doi.org/10.1002/adma.201300027 .

M. Verswyvel , J. Steverlynck , S. Hadj Mohamed , M. Trabelsi , B. Champagne , G. Koeckelberghs . Macromolecules , 2014 . 47 4668 DOI: 10.1021/ma500610p http://doi.org/10.1021/ma500610p .

O. Dhibi , A. Ltaief , A. Bouazizi . Mater. Sci. Semicond. Process. , 2014 . 25 173 DOI: 10.1016/j.mssp.2013.11.004 http://doi.org/10.1016/j.mssp.2013.11.004 .

Y. Guo , L. Jiang , X. Ma , W. Hu , Z. Su . Polym. Chem. , 2013 . 4 4308 DOI: 10.1039/c3py00728f http://doi.org/10.1039/c3py00728f .

R. Verduzco , I. Botiz , D.L. Pickel , S.M. Kilbey , K. Hong , E. Dimasi , S.B. Darling . Macromolecules , 2011 . 44 530 DOI: 10.1021/ma102728z http://doi.org/10.1021/ma102728z .

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