Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices

Imperial College London, London SW7 2AZ, UK.
Journal of the American Chemical Society (Impact Factor: 12.11). 02/2011; 133(10):3272-5. DOI: 10.1021/ja110619k
Source: PubMed


We report the synthesis and polymerization of a novel thieno[3,2-b]thiophene-diketopyrrolopyrrole-based monomer. Copolymerization with thiophene afforded a polymer with a maximum hole mobility of 1.95 cm(2) V(-1) s(-1), which is the highest mobility from a polymer-based OFET reported to date. Bulk-heterojunction solar cells comprising this polymer and PC(71)BM gave a power conversion efficiency of 5.4%.

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    • "However, their restricted absorption to below 600 nm limits their efficiency to also below 5%. Some of the most promising candidates that are being synthesized nowadays to enhance the light harvesting include carbazole–benzothiadiazole copolymers [38] [39] [40], diketopyrrolopyrrole (DPP) based copolymers [41] [42], benzodithiophene (BDT) derivatives [43] [44] [45] as well as indacenodithiophene (IDT) based copolymers [46]. This new generation of semiconducting copolymers combine electron rich segments with electron deficient units such as DPPs along the polymer backbone. "
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    ABSTRACT: Organic photovoltaics will become 30 years old relatively soon. In spite of the impressive development achieved throughout these years, especially in terms of reported power conversion efficiencies, there are still important technological and fundamental obstacles to circumvent before they can be implemented into reliable and long-lasting applications. Regarding device processing, the synthesis of highly soluble polymeric semiconductors first, and fullerene derivatives then, was initially considered as an important breakthrough that would definitely change the fabrication of photovoltaics once for all. Nowadays, the promise of printing solar cells by low-cost and high throughput mass production techniques still stands. However, the potential and the expectation raised by this technology is such that it is considerably difficult to keep track of the most significant progresses being now published in different and even monographic journals. There is therefore the need to compile the most remarkable advances in well-documented reviews than can be used as a reference for future ideas and works. In this letter, we review the development of polymeric solar cells from its origin to the most efficient devices published to date. After analyzing their fundamental limits, we separate these achievements into three different categories traditionally followed by the scientific community to push devices over 10% power conversion efficiency: Active materials, strategies -fabrication/processing procedures- that can mainly modify the active film morphology and result in improved efficiencies for the same starting materials, and all the different cell layout/architectures that have been used in order to extract as high photocurrent as possible from the Sun. The synthesis of new donors and acceptors, the use of additives and post-processing techniques, buffer interlayers, inverted and tandem designs are some of the most important aspects that are in detailed reviewed in this letter. All have equally contributed to develop this technology and leave it at doors of commercialization.
    Organic Electronics 04/2015; 19. DOI:10.1016/j.orgel.2015.01.014 · 3.83 Impact Factor
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    • "The bulk heterojunction solar cells (BHJSCs) with the simple architecture have been widely produced and investigated [7] [8] [9]. The active layers in BHJSCs typically consist of a blend of donor and acceptor materials which interpenetrate into conductive networks [10] [11] [12]. Diketopyrrolopyrrole (DPP) is commonly used as the acceptor material in conjugated polymers [13]. "
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    ABSTRACT: Extending conjugation length, involving strong π-π interactions and large electron-withdrawing functional groups have been experimentally proved to be the efficient strategies for performance enhancement of donor-acceptor (D-A) polymers used in organic solar cells. In this paper, considering above strategies, a series of novel D-A conjugated polymers have been designed and theoretically investigated on their electronic structures, energy levels, and optical absorption, using first principles calculation methods under the PBE0/6-311G∗∗ and TD-B3LYP/6-31G∗∗ level. The results show, compared with those base polymers, the newly designed polymers exhibit better performances including narrower band gaps, deeper HOMO energy levels (broadband optical absorption), and better theoretical power conversion efficiencies (PCEs) predicted by Scharber diagrams. These polymers can be used as the active layers in high performance organic solar cells.
    Computational and Theoretical Chemistry 01/2015; 1055. DOI:10.1016/j.comptc.2014.12.027 · 1.55 Impact Factor
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    • "Benzothiadiazoles and diketopyrrolopyrroles constitute popular electron accepting units in DA copolymers, especially with non-functionalized or functionalized oligothiophene D units [3]. Many of these polymers were tested as active components of such devices as field effect transistors (FETs) [5] [6] [7] [8] [9] [10] [11], photovoltaic cells (PC) [1,2,6,7,12–15], light emitting diodes [16] [17], and others. Copolymers of oligothiophenes and benzothiadiazoles or diketopyrrolopyrroles are electrochemically active both in oxidative and reductive regimes since the presence of an electron accepting center in the polymer repeating unit increases its electron affinity (|EA|) and diminishes the electrochemical gap [3]. "
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    ABSTRACT: A series of solution processable semiconducting donor-acceptor (DA) copolymers consisting of either diketopyrrolopyrrole or benzothiadiazole A units and alkoxy- or alkyl-substituted oligothiophene D units were synthesized. For all prepared copolymers the measured XPS spectra (C1s, S2p, N1s and O1s) were in a very good agreement with the expected chemical constitution. Spectroscopic studies of the synthesized copolymers showed that their optical band gaps were governed by the presence of the alkoxy substituents whose electron donating properties led to additional gap narrowing yielding semiconductors with band gaps of below 1.3 eV in the case of the polymers with the diketopyrrolopyrrole A unit. The same trend was observed with the electrochemical band gaps, whose values were however found to be ca. 0.4 eV superior to the corresponding optical band gaps values. Vibrational model was calculated for two of the synthesized copolymers with the goal to unequivocally attribute the observed Raman modes and to support the interpretation of the spectral changes induced by the electrochemical oxidation. It was established that the electrochemical oxidative doping of the copolymer with the benzothiadiazole A unit is limited to the oligothiophene segment in which the charge of the formed polycation is localized. To the contrary, in the case of the polymer with the diketopyrrolopyrrole A segment the charge imposed on the oligothiophene segment delocalizes towards the diketopyrrolopyrrole unit. These findings are in perfect agreement with the UV-vis-NIR spectroelectrochemistry data which show strong localization of electrochemically created charge carriers in the benzothiadiazole - oligothiophene copolymer and their metallic-like delocalization in the diketopyrrolopyrrole one. The latter seems to be very interesting not only as a potential low band gap component of organic photovoltaic cells but also, in the doped state, as electronic conductor of metallic character.
    Electrochimica Acta 10/2014; 144:211–220. DOI:10.1016/j.electacta.2014.07.147 · 4.50 Impact Factor
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