Abstract
A low bandgap copolymer poly(3,5-didecanyldithieno[3,2-b:2′,3′-d]thiophene-alt-9-fluorenone) (PDTTFO) consisting of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and 9-fluorenone (FO) was synthesized as the donor material for the polymer solar cells via Stille coupling polymerization. Both donor and acceptor units were confirmed by FT-IR and 1H-NMR. Optoelectronic properties of the PDTTFO copolymer were investigated and observed by UV-vis, photoluminescence (PL) spectrum, and cyclic voltammogram (CV). UV-vis spectrum of the film exhibited two absorption peaks centered at 358, 474 nm with a broad absorption band in the range of 300–700 nm and showed a low bandgap of 1.68 eV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the polymer were estimated to be −5.09 and −3.41 eV, respectively. Based on the ITO/PEDOT:PSS/PDTTFO:PCBM/Al device structure, the power conversion efficiency (PCE) under the illumination of AM 1.5 (100 mW/cm2) was 0.374 %. The effects of annealing temperature on the device performance were studied. At annealing temperature of 175 °C/30 min, the device demonstrated an optimal efficiency of 0.923 %. The improved device efficiency under the optimal condition was confirmed by the higher light harvest in UV-vis spectra, the enhanced quenching of photoluminescence (PL) emission, the improved nanoscale morphology by atomic force microscopy (AFM) examination, and the increase in external quantum efficiency.
Similar content being viewed by others
References
Krebs FC, Jorgensen M, Norrman K, Hagemann O, Alstrup J, Nielsen TD, Fyenbo J, Larsen K, Kristensen J (2009) Sol Energy Mater Sol Cells 93:422
Krebs FC (2009) Sol Energy Mater Sol Cells 93:465
Krebs FC, Gevorgyan SA, Alstrup J (2009) J Mater Chem 19:5442
Nielsen TD, Cruickshank C, Foged S, Thorsen J, Krebs FC (2010) Sol Energy Mater Sol Cells 94:1553
Inganäs O, Svensson M, Zhang F, Gadisa A, Persson NK, Wang X, Andersson MR (2004) J Appl Phys A 79:31
Zhang F, Mammo W, Andersson LM, Admassie S, Andersson MR, Inganäs O (2006) Adv Mater 18:2169
Green MA, Emery K, Hishikawa Y, Warta W, Dunlop ED (2011) Prog Photovolt Res Appl 19:565
Ma W, Yang C, Gong X, Lee K, Heeger AJ (2005) Adv Funct Mater 15:1617
Yang X, Van Duren JKJ, Rispens MT, Hummelen JC, Janssen RAJ, Michels MAJ, Loos J (2004) Adv Mater 16:802
Savenije TJ, Kroeze JE, Yang X, Loos J (2005) Adv Funct Mater 15:1260
Bavel V, Sourty SS, De With E, Loos GJ (2009) Nano Lett 9:507
Coffey DC, Reid OG, Rodovsky DB, Bartholomew GP, Ginger DS (2007) Nano Lett 7:738
Chu C, Yang H, Hou W, Huang J, Li G, Yang Y (2008) Appl Phys Lett 92:103306
Peet J, Kim JY, Coates NE, Ma WL, Moses D, Heeger AJ, Bazan GC (2007) Nat Mater 6:497
Wang EG, Wang L, Lan LF, Luo C, Zhuang WL, Peng JB, Cao Y (2008) Appl Phys Lett 92:033307/1
Zhan X, Tan Z, Domercq B, An Z, Zhang X, Barlow S, Li Y, Zhu D, Kippelen B, Marder SR (2007) J Am Chem Soc 129:7246
Zhou E, Yamakawa S, Tajima K, Yang C, Hashimoto K (2009) Chem Mater 21:4055
Brédas JL (1985) J Chem Phys 82:3808
Cheng YJ, Yang SH, Hsu CS (2009) Chem Rev 109:5868
Brocks G, Tol A (1996) J Phys Chem 100:1838
Hou J, Chen HY, Zhang S, Li G, Yang Y (2008) J Am Chem Soc 130:16144
Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP (2009) J Am Chem Soc 131:56
Park SH, Roy A, Beaupre S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ (2009) Nat Photonics 3:297
Patil AV, Lee WH, Kim K, Park H, Kang IN, Lee SH (2011) Polym Chem 2:2907
Pomerantz M, Chalonner-Gill B, Harding MO, Tseng JJ, Pomerantz WJ (1992) J Chem Soc Chem Commun 1672
Wudl F, Kobayashi M, Heeger AJ (1984) J Org Chem 49:3382
Chen GY, Chiang CM, Kekuda D, Lan SC, Chu CW, Wei KH (2010) J Polym Sci A Polym Chem 48:1669
Yuan MC, Chiu MY, Liu SP, Chen CM, Wei KH (2010) Macromolecules 43:6936
Patil AV, Lee WH, Lee E, Kim K, Kang IN, Lee SH (2011) Macromolecules 44:1238
Jung JW, Liu F, Russell TP, Jo WH (2012) Energy Environ Sci 5:6857
Lee K, Sotzing GA (2001) Macromolecules 34:5746
Sotzing GA, Lee K (2002) Macromolecules 35:7281
Lee B, Yavuz MS, Sotzing GA (2006) Macromolecules 39:3118
Chen HY, Hou JH, Zhang SQ, Liang YY, Yang GW, Yang Y, Yu LP, Wu Y, Li G (2009) Nat Photonics 3:649
Liang Y, Xu Z, Xia J, Tsai ST, Wu Y, Li G, Ray C, Yu L (2010) Adv Mater 22:E135
Hou J, Chen HY, Zhang S, Chen RI, Yang Y, Wu Y, Li G (2009) J Am Chem Soc 131:15586
Liang Y, Wu Y, Feng D, Tsai ST, Li G, Ray C, Yu L (2009) J Am Chem Soc 131:7792
Osaka I, Sauve G, Zhang R, Kowalewski T, McCullough RD (2007) Adv Mater 19:4160
Sun Y, Ma Y, Liu Y, Lin Y, Wang Z, Wang Y, Di C, Xiao K, Chen X, Qiu W, Zhang B, Yu G, Hu W, Zhu D (2006) Adv Funct Mater 16:426
Sun Y, Liu Y, Ma Y, Di C, Wang Y, Wu W, Yu G, Hu W, Zhu D (2006) Appl Phys Lett 88:242113
Li J, Ong KH, Lim SL, Ng GM, Tan HS, Chen ZK (2011) Chem Commun 47:9480–9482
Barbarella G, Favaretto L, Sotgiu G, Antolini L, Gigli G, Cingolani R, Bongini A (2001) Chem Mater 13:4112
Sotgiu G, Favaretto L, Barbarella G, Antolini L, Gigli G, Mazzeo M, Bongini A (2003) Tetrahedron 59:5083
Sotgiu G, Zambianchi M, Barbarella G, Aruffo F, Cipriani F, Ventola A (2003) J Org Chem 68:1512
Frey J, Bond AD, Holmes AB (2002) Chem Commun 20:2424
He M, Zhang F (2007) J Org Chem 72:442
Arbizzani C, Catellani M, Mastragostino M, Cerroni MG (1997) J Electroanal Chem 423:23
Catellani M, Lazzarom R, Luzzati S, Brédas JL (1999) Synth Met 101:175
Tauc J (1974) Amorphous and liquid semiconductors. Plenum, New York
Cervini R, Holmes AB, Moratti SC, Köhler A, Friend RH (1996) Synth Met 76:169
Li Y, Xue L, Li H, Li Z, Xu B, Wen S, Tian W (2009) Macromolecules 42:4491
Li G, Shrotriya V, Yao Y, Yang Y (2005) J Appl Phys 98:043704/1
Li G, Yao Y, Yang H, Shrotriya Y, Yang G, Yang Y (2007) Adv Funct Mater 17:1636
Chen LM, Hong Z, Li G, Yang Y (2009) Adv Mater 21:1434
Yao Y, Hou J, Xu Z, Li G, Yang Y (2008) Adv Funct Mater 18:1783
Acknowledgments
We gratefully acknowledge the support of the National Science Council of Republic of China with Grant NSC 99-2221-E-390-001-MY3.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wang, TL., Shieh, YT., Yang, CH. et al. A new low band gap donor–acceptor alternating copolymer containing dithienothiophene and fluorenone unit. J Polym Res 20, 213 (2013). https://doi.org/10.1007/s10965-013-0213-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-013-0213-6