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CC BY-NC-ND 4.0 · Organic Materials 2021; 3(04): 469-476
DOI: 10.1055/a-1639-2383
Organic Materials in Electronics
Original Article

Incorporating Cyano Groups to a Conjugated Polymer Based on Double B←N-Bridged Bipyridine Units for Unipolar n-Type Organic Field-Effect Transistors

Xu Cao
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
b   University of Science and Technology of China, Hefei, 230023, P. R. of China
$   These authors contributed equally to this work.
,
Yang Min
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
c   University of Chinese Academy of Sciences, Beijing, 100049, P. R. of China
$   These authors contributed equally to this work.
,
Hongkun Tian
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
,
Jun Liu 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
b   University of Science and Technology of China, Hefei, 230023, P. R. of China
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Abstract

The development of n-type semiconductors lags far behind that of their p-type counterparts, demonstrating the exploration of exclusive n-type π-conjugated polymers is significant. The double B←N-bridged bipyridine (BNBP)-based polymers P-BNBP-TVT containing (E)-1,2-di(thiophen-2-yl)ethene (TVT) previously reported exhibits ambipolar character because of the electron-rich nature. Herein, we incorporated strong electron-withdrawing cyano groups into the 3,3′-positions of the TVT moiety to a copolymer P-BNBP-2CNTVT to develop n-type π-conjugated polymers. The LUMO/HOMO energy levels of P-BNBP-2CNTVT are −3.80/−5.95 eV, respectively, which are ~0.4 eV lower than that of P-BNBP-TVT without cyano groups. Unsurprisingly, compared with ambipolar P-BNBP-TVT, the organic field-effect transistors (OFETs) based on P-BNBP-2CNTVT showed unipolar n-type characteristics with an electron mobility of 0.026 cm2 · V−1 · s−1 and a lower threshold voltage of ~25 V as well as high I on/I off of ~105. This study demonstrates that organoboron π-conjugated polymers could be regarded as a tool for constructing exclusive n-type semiconducting polymers used in OFETs.

Key words

π-conjugated polymers - cyano-functionalization - organic field-effect transistors - electron transports - n-type polymer semiconductors

Supporting Information



Publication History

Received: 24 July 2021

Accepted: 02 September 2021

Accepted Manuscript online:
07 September 2021

Article published online:
15 October 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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  • References

  • 1 Arias AC, MacKenzie JD, McCulloch I, Rivnay J, Salleo A. Chem. Rev. 2010; 110: 3
    CrossrefPubMed
    • 3a Kang I, Yun H.-J, Chung DS, Kwon S.-K, Kim Y.-H. J. Am. Chem. Soc. 2013; 135: 14896
      CrossrefPubMed
    • 3b Back JY, Yu H, Song I, Kang I, Ahn H, Shin TJ, Kwon S.-K, Oh JH, Kim Y.-H. Chem. Mater. 2015; 27: 1732
      CrossrefPubMed
  • 4 Meijer EJ, de Leeuw DM, Setayesh S, van Veenendaal E, Huisman BH, Blom PW. M, Hummelen JC, Scherf U, Klapwijk TM. Nat. Mater. 2003; 2: 678
    CrossrefPubMed
    • 5a Zhao Z, Yin Z, Chen H, Zheng L, Zhu C, Zhang L, Tan S, Wang H, Guo Y, Tang Q, Liu Y. Adv. Mater. 2017; 29: 1602410
      CrossrefPubMed
    • 5b Fei Z, Han Y, Martin J, Scholes FH, Al-Hashimi M, AlQaradawi SY, Stingelin N, Anthopoulos TD, Heeney M. Macromolecules 2016; 49: 6384
      CrossrefPubMed
    • 6a Gao Y, Zhang X, Tian H, Zhang J, Yan D, Geng Y, Wang F. Adv. Mater. 2015; 27: 6753
      CrossrefPubMed
    • 6b Gruber M, Jung S.-H, Schott S, Venkateshvaran D, Kronemeijer AJ, Andreasen JW, McNeill CR, Wong WW. H, Shahid M, Heeney M, Lee J.-K, Sirringhaus H. Chem. Sci. 2015; 6: 6949
      CrossrefPubMed
    • 6c Yang J, Liu Q, Hu M, Ding S, Liu J, Wang Y, Liu D, Gao H, Hu W, Dong H. Sci. China Chem. 2021; 64: 1410
      CrossrefPubMed
    • 6d Liu L.-N, Li Y.-P, Khalil M, Xu Z.-W, Xie G, Zhang X, Li J, Li W.-S. Chin. J. Chem. 2020; 38: 1663
      CrossrefPubMed
    • 6e Yang J, Wang H, Chen J, Huang J, Jiang Y, Zhang J, Shi L, Sun Y, Wei Z, Yu G, Guo Y, Wang S, Liu Y. Adv. Mater. 2017; 29: 1606162
      CrossrefPubMed
    • 7a Gao Y, Deng Y, Tian H, Zhang J, Yan D, Geng Y, Wang F. Adv. Mater. 2017; 29: 1606217
      CrossrefPubMed
    • 7b Yang J, Zhao Z, Geng H, Cheng C, Chen J, Sun Y, Shi L, Yi Y, Shuai Z, Guo Y, Wang S, Liu Y. Adv. Mater. 2017; 29: 1702115
      CrossrefPubMed
    • 7c Kim M, Park W.-T, Park SA, Park CW, Ryu SU, Lee DH, Noh Y.-Y, Park T. Adv. Funct. Mater. 2019; 29: 1805994
      CrossrefPubMed
    • 7d Lei T, Cao Y, Fan Y, Liu C.-J, Yuan S.-C, Pei J. J. Am. Chem. Soc. 2011; 133: 6099
      CrossrefPubMed
    • 7e Xue G, Zhao X, Qu G, Xu T, Gumyusenge A, Zhang Z, Zhao Y, Diao Y, Li H, Mei J. ACS Appl. Mater. Interfaces 2017; 9: 25426
      CrossrefPubMed
    • 7f Lei T, Dou J.-H, Pei J. Adv. Mater. 2012; 24: 6457
      CrossrefPubMed
    • 8a Chen Z, Wei X, Huang J, Zhou Y, Zhang W, Pan Y, Yu G. ACS Appl. Mater. Interfaces 2019; 11: 34171
      CrossrefPubMed
    • 8b Chen Z, Zhang W, Huang J, Gao D, Wei C, Lin Z, Wang L, Yu G. Macromolecules 2017; 50: 6098
      CrossrefPubMed
    • 8c Sui Y, Shi Y, Deng Y, Li R, Bai J, Wang Z, Dang Y, Han Y, Kirby N, Ye L, Geng Y. Macromolecules 2020; 53: 10147
      CrossrefPubMed
    • 8d Wei C, Zhang W, Huang J, Li H, Zhou Y, Yu G. Macromolecules 2019; 52: 2911
      CrossrefPubMed
    • 8e Zheng Y.-Q, Lei T, Dou J.-H, Xia X, Wang J.-Y, Liu C.-J, Pei J. Adv. Mater. 2016; 28: 7213
      CrossrefPubMed
    • 9a Shi S, Wang H, Chen P, Uddin MA, Wang Y, Tang Y, Guo H, Cheng X, Zhang S, Woo HY, Guo X. Polym. Chem. 2018; 9: 3873
      PubMed
    • 9b Iguchi K, Mikie T, Saito M, Komeyama K, Seo T, Ie Y, Osaka I. Chem. Mater. 2021; 33: 2218
      CrossrefPubMed
    • 9c Wei C, Tang Z, Zhang W, Huang J, Zhou Y, Wang L, Yu G. Polym. Chem. 2020; 11: 7340
      PubMed
    • 9d Yang M, Du T, Zhao X, Huang X, Pan L, Pang S, Tang H, Peng Z, Ye L, Deng Y, Sun M, Duan C, Huang F, Cao Y. Sci. China Chem. 2021; 64: 1219
      CrossrefPubMed
    • 9e Han W, Wang Z, Hu Y, Yang X, Ge C, Gao X. Sci. China Chem. 2020; 63: 1182
      CrossrefPubMed
    • 9f Casey A, Han Y, Fei Z, White AJ. P, Anthopoulos TD, Heeney M. J. Mater. Chem. C 2015; 3: 265
      CrossrefPubMed
    • 9g Kim HG, Kim M, Clement JA, Lee J, Shin J, Hwang H, Sin DH, Cho K. Chem. Mater. 2015; 27: 6858
      CrossrefPubMed
  • 10 Kim HS, Huseynova G, Noh Y.-Y, Hwang D.-H. Macromolecules 2017; 50: 7550
    CrossrefPubMed
    • 11a Yu H, Park KH, Song I, Kim M.-J, Kim Y.-H, Oh JH. J. Mater. Chem. C 2015; 3: 11697
      CrossrefPubMed
    • 11b Choi HH, Baek JY, Song E, Kang B, Cho K, Kwon S.-K, Kim Y.-H. Adv. Mater. 2015; 27: 3626
      CrossrefPubMed
    • 11c Zhu C, Zhao Z, Chen H, Zheng L, Li X, Chen J, Sun Y, Liu F, Guo Y, Liu Y. J. Am. Chem. Soc. 2017; 139: 17735
      CrossrefPubMed
    • 12a Shin J, Um HA, Lee DH, Lee TW, Cho MJ, Choi DH. Polym. Chem. 2013; 4: 5688
      PubMed
    • 12b Chen H, Guo Y, Yu G, Zhao Y, Zhang J, Gao D, Liu H, Liu Y. Adv. Mater. 2012; 24: 4618
      CrossrefPubMed
  • 13 Long X, Gao Y, Tian H, Dou C, Yan D, Geng Y, Liu J, Wang L. Chem. Commun. 2017; 53: 1649
    CrossrefPubMed
    • 14a Sui Y, Deng Y, Han Y, Zhang J, Hu W, Geng Y. J. Mater. Chem. C 2018; 6: 12896
      CrossrefPubMed
    • 14b Lei T, Dou J.-H, Ma Z.-J, Yao C.-H, Liu C.-J, Wang J.-Y, Pei J. J. Am. Chem. Soc. 2012; 134: 20025
      CrossrefPubMed
    • 15a Newman CR, Frisbie CD, da Silva Filho DA, Brédas J.-L, Ewbank PC, Mann KR. Chem. Mater. 2004; 16: 4436
      CrossrefPubMed
    • 15b Nicolai HT, Kuik M, Wetzelaer GA. H, de Boer B, Campbell C, Risko C, Brédas JL, Blom PW. M. Nat. Mater. 2012; 11: 882
      CrossrefPubMed
    • 15c Chua L.-L, Zaumseil J, Chang J.-F, Ou EC. W, Ho PK. H, Sirringhaus H, Friend RH. Nature 2005; 434: 194
      PubMed
    • 15d Hauschild M, Borkowski M, Dral PO, Marszalek T, Hampel F, Xie G, Freudenberg J, Bunz UH. F, Kivala M. Org. Mater. 2020; 02: 204
      PubMed
    • 16a Lei T, Wang J.-Y, Pei J. Acc. Chem. Res. 2014; 47: 1117
      CrossrefPubMed
    • 16b Chochos CL, Economopoulos SP, Deimede V, Gregoriou VG, Lloyd MT, Malliaras GG, Kallitsis JK. J. Phys. Chem. C 2007; 111: 10732
      PubMed
    • 16c Wang H, Huang J, Uddin MA, Liu B, Chen P, Shi S, Tang Y, Xing G, Zhang S, Woo HY, Guo H, Guo X. ACS Appl. Mater. Interfaces 2019; 11: 10089
      CrossrefPubMed
    • 16d Yun H.-J, Kang S.-J, Xu Y, Kim SO, Kim Y.-H, Noh Y.-Y, Kwon S.-K. Adv. Mater. 2014; 26: 7300
      CrossrefPubMed
    • 17a Wang X.-Y, Zhuang F.-D, Zhou X, Yang D.-C, Wang J.-Y, Pei J. J. Mater. Chem. C 2014; 2: 8152
      CrossrefPubMed
    • 17b Zhan X, Zhang J, Gong Y, Tang S, Tu J, Xie Y, Peng Q, Yu G, Li Z. Mater. Chem. Front. 2017; 1: 2341
      CrossrefPubMed
  • 18 Zhao R, Min Y, Dou C, Lin B, Ma W, Liu J, Wang L. ACS Appl. Polym. Mater. 2020; 2: 19
    PubMed