Chlorination of low-band-gap polymers: Toward high-performance polymer solar cells

Mo, Daize; Wang, Huan; Chen, Hui; Qu, Shiwei; Chao, Pengjie; Yang, Zhen; Tian, Leilei; Su, Yu -An; Gao, Yu; Yang, Bing; Chen, Wei; He, Feng

doi:10.1021/acs.chemmater.6b04828

Chlorination of low-band-gap polymers: Toward high-performance polymer solar cells

Journal Article · Wed Mar 08 00:00:00 EST 2017 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.6b04828· OSTI ID:1352927

Mo, Daize ^[1]; Wang, Huan ^[1]; Chen, Hui ^[1]; Qu, Shiwei ^[1]; Chao, Pengjie ^[1]; Yang, Zhen ^[1]; ^[1]; Su, Yu -An ^[2]; Gao, Yu ^[3]; Yang, Bing ^[3]; ^[4]; ^[1]

South Univ. of Science and Technology of China, Shenzhen (People's Republic of China)
Argonne National Lab. (ANL), Lemont, IL (United States)
State Key Lab. of Supramolecular Structure and Materials College of Chemistry Jilin Univ., Changchun (People's Republic of China)
Argonne National Lab. (ANL), Lemont, IL (United States); The Univ. of Chicago, Chicago, IL (United States)

Here, halogenation is an effective way to tune the energy levels of organic semiconducting materials. To date, fluorination of organic semiconducting materials to fabricate polymer solar cells (PSCs) has been used far more than chlorination; however, fluorine exchange reactions suffer from low yields and the resulting fluorinated polymer always comes with higher price, which will greatly hinder their commercial applications. Herein, we designed and synthesized a series of chlorinated donor-acceptor (D-A) type polymers, in which benzo[1,2-b:4,5- b]dithiophene and chlorinated benzothiadiazole units are connected by thiophene π-bridges with an asymmetric alkyl chain. These chlorinated polymers showed deep highest occupied molecular orbital energy levels, which promoted the efficiency of their corresponding PSCs by increasing the device open circuit voltage. The asymmetric alkyl chain on the thiophene moieties gave the final polymer sufficient solubility for solution processing and strong π-π stacking in films allowed for high mobility. Although the introduction of a large chlorine atom increased the torsion angle of the polymer backbone, the chlorinated polymers maintained high crystallinity and a favorable backbone orientation in the blended films. These factors contributed to respectable device performances from thick-film devices, which showed PCEs as high as 9.11% for a 250 nm-thick active layer. These results demonstrate that chlorination is a promising method to fine tune the energy levels of conjugated polymers, and chlorinated benzothiadiazole may be a versatile building block in materials for efficient solar energy conversion.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1352927

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 7 Vol. 29; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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