Journal
SYNTHETIC METALS
Volume 161, Issue 13-14, Pages 1336-1342Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.synthmet.2011.04.032
Keywords
Cyclopentaphenanthrene; 2H-Benzimidazole; Polymer solar cell; Internal charge transfer; Low-band gap
Funding
- Korea government (MEST) [2010-0015069]
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Two new low-band gap polymers, poly[(2,6-(4,4-bis(2'-ethylhexyl)-4H-cyclopenta[def]phenanthrene))alt-(5,5-(4',7'-di(thien-2-yl)-2H-benzimidazole-2'-spirocyclohexane))] (PCPP-DTCHBI) and poly[(2,6-(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[def]phenanthrene))-alt-(5,5-(4',7'-di(thien-2-yl)- 2H-benzimidazole-2'-spirocyclohexane))] (PBEHPCPP-DTCHBI), were synthesized and characterized for the photovoltaics. These polymers showed typical characteristics of low-band gap polymers through the internal charge transfer (ICT) between 4H-cyclopenta[def]phenanthrene as the electron-rich unit and di(thien-2-yl)-2H-benzimidazole-2'-spirocyclohexane as the electron-deficient unit. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels are -5.52 and -3.82 eV for PCPP-DTCHBI, and -5.36 and -3.76 eV for PBEHPCPP-DTCHBI, respectively. Optical band gaps of PCPP-DTCHBI and PBEHPCPP-DTCHBI are 1.70 and 1.60 eV, respectively. As compared to the case of poly[(2,6-(4,4-bis(2'-ethylhexyl)-4H-cyclopenta[def]phenanthrene))-alt-(5,5-(4',7'-di(thien-2-yl)-2,1,3-benzothiadiazole))] (PCPP-DTBT), PCPP-DTCHBI shows deeper HOMO energy levels by 0.12 eV and lower band gap by 0.3 eV. The FET mobilities of PCPP-DTCHBI and PBEHPCPP-DTCHBI are 1.19 x 10(-4) and 5.11 x 10(-5) cm(2)/V s, respectively, and the power conversion efficiencies of the solar cell devices of the PCPP-DTCHBI and PBEHPCPP-DTCHBI blended with [6.6]phenyl-C(71)-butyric acid methyl ester (PC(71)BM) are 1.01% and 0.53%, respectively. The newly designed DTCHBI unit can be used as the electron-deficient moiety inducing efficient ICT for low band gap generation while keeping deep HOMO energy level of the polymer. (C) 2011 Elsevier B.V. All rights reserved.
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