Naphthodithiophene-Based Semiconducting Materials for Applications in Organic Solar Cells

Wu, Ziqi; Yang, Tingbin; Ong, Beng S.; Liang, Yongye; Guo, Xugang

doi:10.2478/oph-2014-0002

Cited by 7 publications

(6 citation statements)

References 86 publications

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“…The power conversion efficiencies (PCEs) of PSCs are driven by materials development in combination with device engineering, now the highest PCEs of bulk heterojunction (BHJ) PSCs have surpassed 11% . In the course of developing high‐performance polymers, the design and synthesis of novel building blocks plays a critical role, such as dithienosilole/dithienogermole and benzodithiophene/naphthodithiophene derivatives . The building blocks should have appropriate geometry, favorable optoelectrical property, and good solubilizing capability.…”

Section: Methodsmentioning

confidence: 99%

Head‐to‐Head Linkage Containing Bithiophene‐Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells

et al. 2016

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Narrow bandgap (1.37-1.46 eV) polymers incorporating a head-to-head linkage containing 3-alkoxy-3'-alkyl-2,2'-bithiophene are synthesized. The head-to-head linkage enables polymers with sufficient solubility and the noncovalent sulfur-oxygen interaction affords polymers with high degree of backbone planarity and film ordering. When integrated into polymer solar cells, the polymers show a promising power conversion efficiency approaching 10%.

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Section: Methodsmentioning

confidence: 99%

Head‐to‐Head Linkage Containing Bithiophene‐Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells

et al. 2016

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“…26,28−32 For example, with TPD and BTI units as the acceptors, p-type mobilities of 0.6−1.3 cm 2 /(V s) and PCEs of 7−9% were demonstrated in OTFTs and PSCs, respectively. 6,33−35 Among possible in-chain electron donors, benzodithiophene, 21,22 naphthodithiophene, 36 and dithienosilole/germole 26,34,37 have recently played key roles in maximizing PCEs. However, despite this success, polymers composed of the above units typically exhibit low degrees of long-range order and modest mobilities.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Among possible in-chain electron donors, benzodithiophene, , naphthodithiophene, and dithienosilole/germole ,, have recently played key roles in maximizing PCEs. However, despite this success, polymers composed of the above units typically exhibit low degrees of long-range order and modest mobilities.…”

Section: Introductionmentioning

confidence: 99%

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

et al. 2015

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As effective building blocks for high-mobility transistor polymers, oligothiophenes are receiving attention for polymer solar cells (PSCs) because the resulting polymers can effectively suppress charge recombination. Here we investigate two series of in-chain donor-acceptor copolymers, PTPDnT and PBTInT, based on thieno[3,4-c]pyrrole-4,6-dione (TPD) or bithiopheneimide (BTI) as electron acceptor units, respectively, and oligothiophenes (nTs) as donor counits, for high-performance PSCs. Intramolecular S···O interaction leads to more planar TPD polymer backbones, however backbone torsion yields greater open-circuit voltages for BTI polymers. Thiophene addition progressively raises polymer HOMOs but marginally affects their band gaps. FT-Raman spectra indicate that PTPDnT and PBTInT conjugation lengths scale with nT catenation up to n = 3 and then saturate for longer oligomer. Furthermore, the effects of oligothiophene alkylation position are explored, revealing that the alkylation pattern greatly affects film morphology and PSC performance. The 3T with "outward" alkylation in PTPD3T and PBTI3T affords optimal π-conjugation, close stacking, long-range order, and high hole mobilities (0.1 cm(2)/(V s)). These characteristics contribute to the exceptional ∼80% fill factors for PTPD3T-based PSCs with PCE = 7.7%. The results demonstrate that 3T is the optimal donor unit among nTs (n = 1-4) for photovoltaic polymers. Grazing incidence wide-angle X-ray scattering, transmission electron microscopy, and time-resolved microwave conductivity measurements reveal that the terthiophene-based PTPD3T blend maintains high crystallinity with appreciable local mobility and long charge carrier lifetime. These results provide fundamental materials structure-device performance correlations and suggest guidelines for designing oligothiophene-based polymers with optimal thiophene catenation and appropriate alkylation pattern to maximize PSC performance.

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“…π-Conjugated polymers comprising electron accepting (A) and electron donating (D) units are widely investigated as semiconductors in organic electronic devices such as organic thin-film transistors (OTFTs) and polymer solar cells (PSCs). − The development of these new polymers relies on the creative design and synthesis of novel A/D building blocks combined with achieving desired structural and physical properties of the polymers such as backbone planarity, considerable π-conjugation, and solid-state chain interactions, as well as sufficient solubility for solution processing. − Furthermore, enabling physical properties specific to a particular device function is required . For instance, for OTFT applications, molecular orbital energies must be compatible with efficient charge injection from the contacts and stable charge transport.…”

Section: Introductionmentioning

confidence: 99%

New Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT)-Based Polymers for Application in Transistors and Solar Cells

et al. 2019

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In this paper we report the rationale and implementation of a new building block for organic electronics based on 4,8-di(2-thienyl)-benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT-T2) and realization of two alkyl-functionalized iso-BBT-tetrathiophene (T4) alternating copolymers (P1 with alkyl = 2DT and P2 with alkyl = 2DH). Compared to the previously investigated small molecules/polymers based on the conventional 4,8-di(2-thienyl)-benzo[l,2-c:4,5-c′]bis[ l,2,5]thiadiazole (BBT-T2), the use of the iso-BBT heterocycle widens the polymer band gap to a region (∼1.4 eV) compatible for use in single junction solar cells. The influence of iso-BBT vs BBT structural variation on the molecular structure, electronic characteristics, and optical properties was accessed by DFT computations, single-crystal determination, optical absorption, and electrochemical measurements. In-plane charge transport for P1 and P2 was investigated in an organic thin-film transistor (OTFT) structure demonstrating hole mobilities approaching 1 cm2 V–1 s–1 and further enhanced by off-center spin-coating method to 1.32 cm2 V–1 s–1. Using PC61BM as acceptor, a remarkable PCE of 10.28% was achieved for P1 along with a current density > 20 mA/cm2. The substantial PCEs of these devices, despite the relatively narrow donor energy gap, is due to retention of high open circuit voltages ( V oc > 0.8 V) as the result of the small energy loss (E loss < 0.6 eV). Atomic force microscopy, transmission electron microscopy, and X-ray diffraction characterization further support the solar cell trends and rationalize structure–property correlations. These results demonstrate that iso-BBT-T2-based polymers are promising candidates for both organic electronics and photonic applications.

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Naphthodithiophene-Based Semiconducting Materials for Applications in Organic Solar Cells

Cited by 7 publications

References 86 publications

Head‐to‐Head Linkage Containing Bithiophene‐Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells

Head‐to‐Head Linkage Containing Bithiophene‐Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

New Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT)-Based Polymers for Application in Transistors and Solar Cells

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