Dithienylthienothiophenebisimide, a Versatile Electron‐Deficient Unit for Semiconducting Polymers

Saito, Masahiko; Osaka, Itaru; Suda, Yosuke; Yoshida, Hiroyuki; Takimiya, Kazuo

doi:10.1002/adma.201601373

Cited by 83 publications

(89 citation statements)

References 22 publications

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“…Recent studies of nonfullerene n‐type materials have further enhanced the performance of OPVs . In addition, semiconducting polymers as the n‐type material have also been intensively studied …”

Section: Introductionmentioning

confidence: 99%

Impact of Noncovalent Sulfur–Fluorine Interaction Position on Properties, Structures, and Photovoltaic Performance in Naphthobisthiadiazole‐Based Semiconducting Polymers

Saito

Fukuhara

Kamimura

et al. 2020

Advanced Energy Materials

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Controlling the energetics and backbone order of semiconducting polymers is essential for the performance improvement of polymer‐based solar cells. The use of fluorine as the substituent for the backbone is known to effectively deepen the molecular orbital energy levels and coplanarize the backbone by noncovalent interactions with sulfur of the thiophene ring. In this work, novel semiconducting polymers are designed and synthesized based on difluoronaphthobisthiadiazole (FNTz) as a new family of naphthobisthiadiazole (NTz)–quaterthiophene copolymer systems, which are one of the highest performing polymers in solar cells. The effect of the fluorination position on the energetics and backbone order is systematically studied. It is found that the dependence of the solar cell fill factor on the active layer thickness is very sensitive to the fluorination position. It is thus further investigated and discussed how the structural features of the polymers influence the photovoltaic parameters as well as the diode characteristics and bimolecular recombination. Further, the polymer with fluorine on both the naphthobisthiadiazole and quaterthiophene moieties exhibits a quite high power conversion efficiency of 10.8% in solar cells in combination with a fullerene. It is believed that the results would offer new insights into the development of semiconducting polymers.

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Section: Introductionmentioning

confidence: 99%

Impact of Noncovalent Sulfur–Fluorine Interaction Position on Properties, Structures, and Photovoltaic Performance in Naphthobisthiadiazole‐Based Semiconducting Polymers

Saito

Fukuhara

Kamimura

et al. 2020

Advanced Energy Materials

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“…In addition to these diimide‐functionalized NDI and PDI‐based polymers, it was found recently that a monoimide, thieno[3,4‐c]pyrrole‐4,6‐dione (TPD, Figure a) also enabled n‐type polymers with a promising all‐PSC performance, showing a PCE up to 4.4% . Inspired by the monoimide‐functionalized TPD‐based polymers, we recently reported an n‐type polymer based on a ladder‐type diimide‐functionalized building block f‐BTI2 (Figure b), and the polymer showed superior all‐PSC performance with a PCE of 6.8% . The results demonstrated the positive effects of increasing the imide number on promoting polymer n‐type characteristics and improving all‐PSC performance.…”

Section: Introductionmentioning

confidence: 99%

Triimide‐Functionalized n‐Type Polymer Semiconductors Enabling All‐Polymer Solar Cells with Power Conversion Efficiencies Approaching 9%

et al. 2019

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Two triimide‐functionalized n‐type acceptor polymers are designed and synthesized, which show narrower bandgap, lower‐lying frontier molecular orbital energy levels, and improved film morphology than the diimide‐functionalized analogue polymers. When blended with a p‐type donor polymer semiconductor PTB7‐Th, an outstanding power conversion efficiency of 8.98% with a remarkable open‐circuit voltage of 1.03 V is attained. This efficiency is among the highest values in all‐polymer solar cells (all‐PSCs) reported till today, surpassing that (6.85%) of the diimide‐functionalized analogue polymers by a big margin and even higher than that (8.69%) of the fullerene‐based solar cells. The results demonstrate that the triimide‐functionalized f‐BTI3 is an excellent building block for developing n‐type polymer semiconductors, and the polymer f‐BTI3‐T is among the best‐performing n‐type polymers for applications in all‐PSCs. The structure–property correlations of these imide‐functionalized polymer semiconductors offer important guides for developing high‐performance n‐type polymer semiconductors.

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“…[17] When incorporated into OTFTs,t he BTI homopolymer showed an encouraging m e value of 0.2 cm 2 V À1 s À1 . [23] Furthermore, aseries of fused BTI oligomers,BTI-BTI5, with different pconjugation lengths were synthesized. Recently,afused BTI dimer,f -BTI2, which can also be regarded as aquaterthiophene-baseddiimide,was developed by Osaka and co-workers,and the resulting polymers showed PCE values of 7-8 %when used as apolymer donor and 1.0 % when used as apolymer acceptor in all-PSCs.…”

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confidence: 99%

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

Wang,

Yan,

Guo

et al. 2017

Angew Chem Int Ed

156

106

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Two new bithiophene imide (BTI)-based n-type polymers were synthesized. f-BTI2-FT based on a fused BTI dimer showed a smaller band gap, a lower LUMO, and higher crystallinity than s-BTI2-FT containing a BTI dimer connected through a single bond. s-BTI2-FT exhibited a remarkable electron mobility of 0.82 cm V s , and f-BTI2-FT showed a further improved mobility of 1.13 cm V s in transistors. When blended with the polymer donor PTB7-Th, f-BTI2-FT-based all-polymer solar cells (all-PSCs) attained a PCE of 6.85 %, the highest value for an all-PSC not based on naphthalene (or perylene) diimide polymer acceptors. However, s-BTI2-FT all-PSCs showed nearly no photovoltaic effect. The results demonstrate that f-BTI2-FT is one of most promising n-type polymers and that ring fusion offers an effective approach for designing polymers with improved electrical properties.

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Dithienylthienothiophenebisimide, a Versatile Electron‐Deficient Unit for Semiconducting Polymers

Cited by 83 publications

References 22 publications

Impact of Noncovalent Sulfur–Fluorine Interaction Position on Properties, Structures, and Photovoltaic Performance in Naphthobisthiadiazole‐Based Semiconducting Polymers

Impact of Noncovalent Sulfur–Fluorine Interaction Position on Properties, Structures, and Photovoltaic Performance in Naphthobisthiadiazole‐Based Semiconducting Polymers

Triimide‐Functionalized n‐Type Polymer Semiconductors Enabling All‐Polymer Solar Cells with Power Conversion Efficiencies Approaching 9%

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

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