Effect of Fused Thiophene Bridges on the Efficiency of Non-Fullerene Polymer Solar Cells made with Conjugated Donor Copolymers Containing Alkyl Thiophene-3-Carboxylate

Su Hong Park; Jong-Soo Ahn; Na Yeon Kwon; Chau Hong Diem; Amit Kumar Harit; Han Young Woo; Min Ju Cho; Dong Hoon Choi

Macromolecular Research, Vol.29, No.6, 435-442, June, 2021

DOI10.1007/s13233-021-9053-0 Export Citation

Effect of Fused Thiophene Bridges on the Efficiency of Non-Fullerene Polymer Solar Cells made with Conjugated Donor Copolymers Containing Alkyl Thiophene-3-Carboxylate

Su Hong Park, Jong-Soo Ahn, Na Yeon Kwon, Chau Hong Diem, Amit Kumar Harit, Han Young Woo, Min Ju Cho^†, and Dong Hoon Choi^†

Department of Chemistry, Research Institute for Natural Sciences, Korea University, 145 Anam-Ro, Sungbuk-gu, Seoul 02841, Korea

E-mail:,

New wide-bandgap donor-acceptor-π type conjugated polymers, PBTTT and PBTDTT, containing different π-extended conjugated bridges between benzodithiophene (BDT) as a donating unit and 3-carboxylthiophene (3CT) as a weak electron- withdrawing group, were successfully synthesized and employed as donor polymers for polymer solar cells. Thienothiophene (TT) and dithienothiophene (DTT) were selected as fused thiophene bridges for inclusion in the polymer backbone instead of a single thiophene. As a control donor polymer, PBTT containing a single thiophene bridge was also prepared. Its properties were compared with those of PBTTT and PBTDTT. As the conjugation length of the p-extended bridge (i.e., from thiophene to DTT) increased, the bandgap of the polymer slightly decreased, and the highest occupied molecular orbital level shifted to a higher-lying level. Compared to PBTT, PBTTT and PBTDTT exhibited relatively low solubility and red-shifted absorption spectra in solution states. PBTTT and PBTDTT showed strong aggregation between polymer chains, even in solution states, which were similar to the film state. Among the three copolymers, PBTTT-based non-fullerene polymer solar cells (NF-PSCs) with ITIC-Me showed a high power conversion efficiency of 7.30% with a high short circuit current density of 14.05 mA/cm2. The superior performance of the NF-PSCs based on PBTTT may be attributed to their predominant face-on orientation of polymer chains and relatively more favorable surface morphology.

Keywords:3-carboxylthiophene;benzodithiophene;fused thiophene;polymer solar cells;power conversion efficiency

[References]

Ma Y, Kang Z, Zheng Q, J. Mater. Chem. A, 5, 1860 (2017)
Xu X, Zhang G, Li Y, Peng Q, Chin. Chem. Lett., 30, 809 (2019)
An C, Zheng Z, Hou J, Chem. Commun., 56, 4750 (2020)
Liu D, Yang B, Jang B, Xu B, Zhang S, He C, Woo HY, Hou J, Energy Environ. Sci., 10, 546 (2017)
Lee B, Jeong S, Cho Y, Jeong M, Lee SM, Oh J, Yang C, Adv. Funct. Mater., 30, 200503 (2020)
Jung S, Oh J, Yang UJ, Lee SM, Lee J, Jeong M, Cho Y, Kim S, Baik JM, Yang C, Nano Energy, 77, 105271 (2020)
Cho Y, Lee TH, Jeong S, Park SY, Lee B, Kim JY, Yang C, ACS Appl. Energy Mater., 3, 7689 (2020)
Yan C, Barlow S, Wang Z, Yan H, Jen AKY, Marder SR, Zhan X, Nat. Rev. Mater., 3, 18003 (2018)
Chen W, Zhang Q, J. Mater. Chem. C, 5, 1275 (2017)
Wadsworth A, Moser M, Marks A, Little MS, Gasparini N, Brabec CJ, Baran D, McCulloch I, Chem. Soc. Rev., 48, 1596 (2019)
Firdaus Y, Maffei LP, Cruciani F, Muller MA, Liu S, Lopatin S, et al., Adv. Energy Mater., 7, 170083 (2017)
Park GE, Choi S, Park SY, Lee DH, Cho MJ, Choi DH, Adv. Eng. Mater., 7, 170056 (2017)
Zhao B, Wang W, Xin J, Wu H, Liu H, Guo Z, Cong Z, Ma W, Cao C, ACS Sustain. Chem. Eng., 6, 2177 (2018)
Wen S, Li Y, Rath T, Li Y, Wu Y, Bao X, Han L, Ehmann H, Trimmel G, Zhang Y, Yang R, Chem. Mater., 31, 919 (2019)
Guo B, Li W, Guo X, MEng X, Ma W, Zhang M, Li Y, Nano Energy, 34, 556 (2017)
Xu X, Yu T, Bi Z, Ma W, Li Y, Peng Q, Adv. Mater., 30, 170397 (2018)
Xu X, Li Z, Bi Z, Yu T, Ma W, Feng K, Li Y, Peng Q, Adv. Mater., 30, 180073 (2018)
Pomerantz M, Cheng Y, Kasim RK, Elsenbaumer RL, J. Mater. Chem., 9, 2155 (1999)
Huo LJ, Chen TL, Zhou Y, Hou JH, Chen HY, Yang Y, Li YF, Macromolecules, 42(13), 4377 (2009)
An Y, Liao X, Chen L, Yin J, Ai Q, Xie Q, Huang B, Jen AKY, Chen Y, Adv. Funct. Mater., 28, 170651 (2018)
Cho MJ, Seo J, Luo K, Kim KH, Choi DH, Prasad PN, Polymer, 53(18), 3835 (2012)
Wang Q, Li M, Sui Y, Wang Z, Liang Z, Geng Y, J. Mater. Chem. C, 7, 9581 (2019)
Li SS, Ye L, Zhao WC, Yan HP, Yang B, Liu DL, Li WN, Ade H, Hou JH, J. Am. Chem. Soc., 140(23), 7159 (2018)
Lin HR, Chen SS, Li ZK, Lai JYL, Yang GF, McAfee T, Jiang K, Li YK, Liu YH, Hu HW, Zhao JB, Ma W, Ade H, Yan H, Adv. Mater., 27(45), 7299 (2015)
Wu QH, Zhao DL, Schneider AM, Chen W, Yu LP, J. Am. Chem. Soc., 138(23), 7248 (2016)
Gao L, Zhang Z, Bin H, Xue L, Yang Y, Wang C, Liu F, Russell TP, Li Y, Adv. Mater., 25, 8288 (2016)
Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H, Nat. Photonics, 9, 403 (2015)

[1] Ma Y, Kang Z, Zheng Q, J. Mater. Chem. A, 5, 1860 (2017)

[2] Xu X, Zhang G, Li Y, Peng Q, Chin. Chem. Lett., 30, 809 (2019)

[3] An C, Zheng Z, Hou J, Chem. Commun., 56, 4750 (2020)

[4] Liu D, Yang B, Jang B, Xu B, Zhang S, He C, Woo HY, Hou J, Energy Environ. Sci., 10, 546 (2017)

[5] Lee B, Jeong S, Cho Y, Jeong M, Lee SM, Oh J, Yang C, Adv. Funct. Mater., 30, 200503 (2020)

[6] Jung S, Oh J, Yang UJ, Lee SM, Lee J, Jeong M, Cho Y, Kim S, Baik JM, Yang C, Nano Energy, 77, 105271 (2020)

[7] Cho Y, Lee TH, Jeong S, Park SY, Lee B, Kim JY, Yang C, ACS Appl. Energy Mater., 3, 7689 (2020)

[8] Yan C, Barlow S, Wang Z, Yan H, Jen AKY, Marder SR, Zhan X, Nat. Rev. Mater., 3, 18003 (2018)

[9] Chen W, Zhang Q, J. Mater. Chem. C, 5, 1275 (2017)

[10] Wadsworth A, Moser M, Marks A, Little MS, Gasparini N, Brabec CJ, Baran D, McCulloch I, Chem. Soc. Rev., 48, 1596 (2019)

[11] Firdaus Y, Maffei LP, Cruciani F, Muller MA, Liu S, Lopatin S, et al., Adv. Energy Mater., 7, 170083 (2017)

[12] Park GE, Choi S, Park SY, Lee DH, Cho MJ, Choi DH, Adv. Eng. Mater., 7, 170056 (2017)

[13] Zhao B, Wang W, Xin J, Wu H, Liu H, Guo Z, Cong Z, Ma W, Cao C, ACS Sustain. Chem. Eng., 6, 2177 (2018)

[14] Wen S, Li Y, Rath T, Li Y, Wu Y, Bao X, Han L, Ehmann H, Trimmel G, Zhang Y, Yang R, Chem. Mater., 31, 919 (2019)

[15] Guo B, Li W, Guo X, MEng X, Ma W, Zhang M, Li Y, Nano Energy, 34, 556 (2017)

[16] Xu X, Yu T, Bi Z, Ma W, Li Y, Peng Q, Adv. Mater., 30, 170397 (2018)

[17] Xu X, Li Z, Bi Z, Yu T, Ma W, Feng K, Li Y, Peng Q, Adv. Mater., 30, 180073 (2018)

[18] Pomerantz M, Cheng Y, Kasim RK, Elsenbaumer RL, J. Mater. Chem., 9, 2155 (1999)

[19] Huo LJ, Chen TL, Zhou Y, Hou JH, Chen HY, Yang Y, Li YF, Macromolecules, 42(13), 4377 (2009)

[20] An Y, Liao X, Chen L, Yin J, Ai Q, Xie Q, Huang B, Jen AKY, Chen Y, Adv. Funct. Mater., 28, 170651 (2018)

[21] Cho MJ, Seo J, Luo K, Kim KH, Choi DH, Prasad PN, Polymer, 53(18), 3835 (2012)

[22] Wang Q, Li M, Sui Y, Wang Z, Liang Z, Geng Y, J. Mater. Chem. C, 7, 9581 (2019)

[23] Li SS, Ye L, Zhao WC, Yan HP, Yang B, Liu DL, Li WN, Ade H, Hou JH, J. Am. Chem. Soc., 140(23), 7159 (2018)

[24] Lin HR, Chen SS, Li ZK, Lai JYL, Yang GF, McAfee T, Jiang K, Li YK, Liu YH, Hu HW, Zhao JB, Ma W, Ade H, Yan H, Adv. Mater., 27(45), 7299 (2015)

[25] Wu QH, Zhao DL, Schneider AM, Chen W, Yu LP, J. Am. Chem. Soc., 138(23), 7248 (2016)

[26] Gao L, Zhang Z, Bin H, Xue L, Yang Y, Wang C, Liu F, Russell TP, Li Y, Adv. Mater., 25, 8288 (2016)

[27] Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H, Nat. Photonics, 9, 403 (2015)