Copolymers Comprising 2,7-Carbazole and Bis-benzothiadiazole Units for Bulk-Heterojunction Solar Cells

• Published in: Chemistry : a European journal Vol. 17; no. 51; pp. 14681 - 14688
• Main Authors: Kim, Jonggi, Yun, Myoung Hee, Anant, Piyush, Cho, Shinuk, Jacob, Josemon, Kim, Jin Young, Yang, Changduk
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 16.12.2011; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: bis-benzothiadiazole; carbazole; Chemistry; Chemistry, Multidisciplinary; Copolymers; Derivatives; donor-acceptor systems; Energy conversion efficiency; Energy gaps (solid state); Molecular orbitals; Photovoltaic cells; Physical Sciences; Polymers; Science & Technology; Solar cells; Solar energy; OPEN-CIRCUIT VOLTAGE; CARRIER MOBILITY; BAND-GAP POLYMER; FIELD-EFFECT TRANSISTORS; INTRAMOLECULAR CHARGE-TRANSFER; DONOR-ACCEPTOR SUBSTITUTION; PHOTOVOLTAIC CELLS; bis-benzothiadiazole; donor-acceptor systems; carbazole; polymers; solar cells; HETEROCYCLIC POLYMERS; NONLINEAR-OPTICAL-MATERIALS; PI-CONJUGATED SYSTEMS
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201101258

On the basis of theoretical considerations of the intramolecular charge transfer (ICT) effect, we have designed a series of donor (D)–acceptor (A) conjugated polymers based on bis‐benzothiadiazole (BBT). A PPP‐type copolymer of electron‐rich 2,7‐carbazole (CZ) and electron‐deficient BBT units poly[N‐(2‐decyltetradecyl)‐2,7‐carbazole‐co‐7,7′‐{4,4′‐bis‐(2,1,3‐benzothiadiazole)}] (PCZ‐BBT), a PPV‐type copolymer poly[N‐(2‐decyltetradecyl)‐2,7‐carbazolevinylene‐co‐7,7′‐{4,4′‐bis‐(2,1,3‐benzothiadiazolevinylene)}] (PCZV‐BBTV), and a tercopolymer based on carbazole, thiophene, and BBT poly[N‐(2‐decyltetradecyl)‐2,7‐(di‐2‐thienyl)carbazole‐co‐7,7′‐{4,4′‐bis‐(2,1,3‐benzothiadiazole)}] (PDTCZ‐BBT) have been synthesized to understand the influence of BBT acceptor structure and linkage on the photovoltaic characteristics of the resulting materials. Both the HOMO and LUMO of the resulting polymers are found to be deeper‐lying than those of benzothiadiazole‐based polymers. The measured electrochemical band gaps (eV) are in the following order: PDTCZ‐BBT (1.65 eV) < PCZV‐BBTV (1.69 eV) < PCZ‐BBT (1.75 eV). All the polymers provide a photovoltaic response when blended with a fullerene derivative as an electron acceptor. The best cell reaches a power conversion efficiency of 2.07 % estimated under standard solar light conditions (AM1.5G, 100 mW cm−2). We demonstrate for the first time that BBT‐based polymers are promising materials for use in bulk‐heterojunction solar cells. Influence on photovoltaic characteristics: A family of donor (D)–acceptor (A) conjugated polymers based on bis‐benzothiadiazole (BBT), namely PCZ‐BBT, PCZV‐BBTV, and PDTCZ‐BBT, are presented for use in bulk‐heterojunction solar cells. Both the HOMO and LUMO of the resulting polymers are found to be deeper lying than those of benzothiadiazole‐based polymers.