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Synthesis and Applications of Low-Bandgap Conjugated Polymers Containing Phenothiazine Donor and Various Benzodiazole Acceptors for Polymer Solar Cells
(2010-11-01)
Padhy, Harihara
;
Huang, Jen-Hsien
;
Sahu, Duryodhan
;
Patra, Dhananjaya
;
Kekuda, Dhananjay
A series of soluble donor-acceptor conjugated polymers comprising of phenothiazine donor and various benzodiazole acceptors (i.e., benzothiadiazole, benzoselenodiazole, and benzoxadiazole) sandwiched between hexyl-thiophene linkers were designed, synthesized, and used for the fabrication of polymer solar cells (PSC). The effects of the benzodiazole acceptors on the thermal, optical, electrochemical, and photovoltaic properties of these low-bandgap (LBG) polymers were investigated. These LBG polymers possessed large molecular weight (M(n)) in the range of 3.85-5.13 x 10(4) with high thermal decomposition temperatures, which demonstrated broad absorption in the region of 300-750 nm with optical bandgaps of 1.80-1.93 eV. Both the HOMO energy level (-5.38 to -5.47 eV) and LUMO energy level (-3.47 to -3.60 eV) of the LBG polymers were within the desirable range of ideal energy level. Under 100 mW/cm(2) of AM 1.5 white-light illumination, bulk heterojunction PSC devices containing an active layer of electron donor polymers mixed with electron acceptor [6,6]-phenyl-C(61)-butyric acid methyl ester (PC(61)BM) or [6,6]-phenyl-C(71)-butyric acid methyl ester (PC(71)BM) in different weight ratios were investigated. The best performance of the PSC device was obtained by using polymer PP6DHTBT as an electron donor and PC(71)BM as an acceptor in the weight ratio of 1:4, and a power conversion efficiency value of 1.20%, an open-circuit voltage (V(oc)) value of 0.75 V, a short-circuit current (J(sc)) value of 4.60 mA/cm(2), and a fill factor (FF) value of 35.0% were achieved. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 4823-4834, 2010
Synthesis and Applications of Cyano-Vinylene-Based Polymers Containing Cyclopentadithiophene and Dithienosilole Units for Photovoltaic Cells
(2011-08-01)
Padhy, Harihara
;
Sahu, Duryodhan
;
Patra, Dhananjaya
;
Pola, Murali Krishna
;
Huang, Jen-Hsien
Two beta-cyano-thiophenevinylene-based polymers containing cyclopentadithiophene (CPDT-CN) and dithienosilole (DTS-CN) units were synthesized via Stille coupling reaction with Pd(PPh(3))(4) as a catalyst. The effects of the bridged atoms (C and Si) and cyano-vinylene groups on their thermal, optical, electrochemical, charge transporting, and photovoltaic properties were investigated. Both polymers possessed the highest occupied molecular orbital (HOMO) levels of about -5.30 eV and the lowest unoccupied molecular orbital (LUMO) levels of about -3.60 eV, and covered broad absorption ranges with narrow optical band gaps (ca. 1.6 eV). The bulk heterojunction polymer solar cell (PSC) devices containing an active layer of electron-donor polymers (CPDT-CN and DTS-CN) blended with an electron-acceptor, that is, [6,6]-phenyl-C(61)-butyric acid methyl ester (PC(61)BM) or [6,6]-phenyl-C(71)-butyric acid methyl ester (PC(71)BM), in different weight ratios were explored under 100 mW/cm(2) of AM 1.5 white-light illumination. The PSC device based on DTS-CN:PC(71)BM (1:2 w/w) exhibited a best power conversion efficiency (PCE) value of 2.25% with V(oc) = 0.74 V, J(sc) = 8.39 mA/cm(2), and FF = 0.36. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3417-3425, 2011
Novel narrow-band-gap conjugated copolymers containing phenothiazine-arylcyanovinyl units for organic photovoltaic cell applications
(2008-07-01)
Li, Kuang-Chieh
;
Hsu, Ying-Chan
;
Lin, Jiann-T'Suen
;
Yang, Chang-Chung
;
Wei, Kung-Hwa
A series of novel narrow-band-gap copolymers (P1-P12) composed of alkyl-substituted fluorene (FO) units and six analogous mono- and bis(2-aryl-2-cyano-vinyl)- 10-hexylphenothiazine monomers (M1-M6) were synthesized by a palladium-catalyzed Suzuki coupling reaction with two different feed in ratios of FO to M1-M6 (molar ratio = 3:1 and 1:1). The absorption spectra of polymers P1-P12 exhibited broad peaks located in the UV and visible regions from 400 to 800 nm with optical band gaps at 1.55-2.10 eV, which fit near the wavelength of the maximum solar photon reflux. Electrochemical experiments displayed that the reversible p- and n-doping processes of copolymers were partially reversible, and the proper HOMO/LUMO levels enabled a high photovoltaic open-circuit voltage. As blended with [6,6]-phenyl C-61 butyric acid methyl ester (PCBM) as an electron acceptor in bulk heterojunction photovoltaic devices, narrow-band-gap polymers P1-P12 as electron donors showed significant photovoltaic performance which varied with the intramolecular donor-acceptor interaction and their mixing ratios to PCBM. Under 100 mW/cm(2) of AM 1.5 white-light illumination, the device of copolymer P12 produced the highest preliminary result having an open-circuit voltage of 0.64 V, a short-circuit current of 2.70 mA/cm(2), a fill factor of 0.29, and an energy conversion efficiency of 0.51%. (c) 2008 Wiley Periodicals, Inc.
Soluble Narrow-Band-Gap Copolymers Containing Novel Cyclopentadithiophene Units for Organic Photovoltaic Cell Applications
(2009-04-15)
Li, Kuang-Chieh
;
Hsu, Ying-Chan
;
Lin, Jiann-T'suen
;
Yang, Chang-Chung
;
Wei, Kung-Hwa
Five novel conjugated copolymers (P1-P5) containing coplanar cyclopentadithiophene (CPDT) units (incorporated with arylcyanovinyl and keto groups in different molar ratios) were synthesized and developed for the applications of polymer solar cells (PSCs). Polymers P1-P5 covered broad absorption ranges from U-V to near infrared (400-900 nm) with narrow optical band gaps of 1.38-1.70 eV, which are compatible with the maximum solar photon reflux. Partially reversible p- and n-doping processes of P1-P5 in electrochemical experiments were observed, and the proper molecular design for highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) levels of P1-P5 induced the highest photovoltaic open-circuit voltage in the PSC devices, compared with those previously reported CPDT-based narrow-band-gap polymers. Powder X-ray diffraction (XRD) analyses suggested that these copolymers formed self-assembled pi-pi stacking and pseudobilayered structures. Under 100 mW/cm(2) of AM 1.5 white-light illumination, bulk hetero-junction PSC devices containing an active layer of electron donor polymers P1-P5 mixed with electron acceptor [6,6]-phenyl C(61) butyric acid methyl ester (PCBM) in the weight ratio of 1:4 were investigated. The PSC device containing P1 gave the best preliminary result with an open-circuit voltage of 0.84 V, a short-circuit current of 2.36 mA/cm(2), and a fill factor of 0.38, offering an overall power conversion efficiency (PCE) of 0.77% as well as a maximal quantum efficiency of 23% from the external quantum efficiency (EQE) measurements. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2073-2092, 2009

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