Naphthodithiophene-Based Donor–Acceptor Polymers: Versatile Semiconductors for OFETs and OPVs

Osaka, Itaru; Abe, Toru; Shimawaki, Masafumi; Koganezawa, Tomoyuki; Takimiya, Kazuo

doi:10.1021/mz300065t

Cited by 133 publications

(103 citation statements)

References 34 publications

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“…In particular, for semiconducting polymers with donor-acceptor backbones that have strong intermolecular interactions, branched alkyl groups are necessary for solubility in organic solvents. 19,20 Although such bulky branched alkyl groups efficiently increase the solubility, they suppress the aggregation or close interchain π-π stacking of the polymers relative to the linear alkyl groups, resulting in inefficient charge transport. 20 A recent study demonstrated that moving the branching position in the branched alkyl group away from the conjugated backbone reduced the steric effect and π-π stacking distances, which enhanced the charge carrier mobilities in OFET devices.…”

Section: Introductionmentioning

confidence: 99%

Effects of branching position of alkyl side chains on ordering structure and charge transport property in thienothiophenedione- and quinacridone-based semiconducting polymers

Kawabata

Saito

Takemura

et al. 2016

Polym J

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To investigate the effect of the branching position of the alkyl groups on the side chain of semiconducting polymers, we synthesized two series of semiconducting polymers based on thienothiophene-2,5-dione (PTTD4Ts) and quinacridone (PQA2Ts). 2-Decyltetradecyl, 3-decylpentadecyl, 4-decylhexadecyl, and 5-decylheptadecyl groups were used, and the branching position was systematically varied from the second carbon from the backbone to the fifth carbon. These branched side chains are introduced into the thiophene ring for PTTD4Ts and the quinacridone unit for PQA2Ts. The polymer thin films exhibited small but clear differences in their optical absorption spectra, suggesting that the intermolecular interaction in the solid state varied based on the branching position. The grazing incident X-ray diffraction study revealed that the π-π stacking d-spacing of both polymers decreased when the branching position was moved away from the backbones, indicating that the intermolecular interaction was enhanced. Therefore, regardless of the core where the alkyl groups were introduced, the branching position effectively improved the ordering structure of the polymers, which was most likely due to suppressed steric hindrance. Although PTTD4Ts did not exhibit a clear correlation between the branching position and charge carrier mobility, the mobility of PQA2Ts gradually increased as the branching position moved away from the backbone.

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Section: Introductionmentioning

confidence: 99%

Effects of branching position of alkyl side chains on ordering structure and charge transport property in thienothiophenedione- and quinacridone-based semiconducting polymers

Kawabata

Saito

Takemura

et al. 2016

Polym J

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“…Benzothiadiazole (BTz) and naphthobisthiadiazole (NTz), a doubly BTz-fused heteroaromatic ring, are chosen as the acceptor units to create two polymer semiconductors M9 and M10 (Figure 4), respectively. Polymers were synthesized under Stille coupling and show good solubilities in common organic solvents when appropriate side chains were used on the bridging thiophene units [81]. Using naphthobisthiadiazole as acceptor unit, the polymer M10 shows broader absorption and red-shifted λmax of 632 nm compared to the benzothiadiazole-based polymer analogue M9.…”

Section: Naphtho[23-b:67-b′] Dithiophene-based Organic Semiconductorsmentioning

confidence: 99%

Naphthodithiophene-Based Semiconducting Materials for Applications in Organic Solar Cells

Wu¹,

Yang²,

Ong³

et al. 2014

Organic Photonics and Photovoltaics

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“…P41 exhibits not only high field-effect transistor (FET) mobility of about 0.56 cm 2 /Vs, but also a high PCE of 6.3 %, both of which are significantly higher than that of the BT-based analogues [53]. Combined naphthodithiophenes with NT, polymer P42 including highly π-extended (four-ring fused) heteroarenes both as the donor and acceptor units were synthesized by Osaka et al By virtue of this large π-extended system, a very close π-π stacking of 3.5 Å showed up in the solid state and it was found to be one of the few examples of versatile polymers that exhibit both high FET mobility of ~0.5 cm/ Vs and high PCE of ~5 % [54]. However, due to the highly π-extended system along the backbone, the Achilles' heel of P42 is its low solubility, which will severely hinder its processability.…”

Section: Nt-based Donor Polymers For Photovoltaic Applicationmentioning

confidence: 99%

Donor Materials for Organic Solar Cell (OSC)

Song

2014

Organic and Hybrid Solar Cells

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In the past 10 years, the highest efficiency obtained from organic photovoltaics (OPVs), such as bulk heterojunction (BHJ) polymer solar cells (PSCs), has risen from 2.5 to 11 %, while the solution-processed small molecule (SM) BHJ solar cells arrived at competitive level of 10 %. This rapid progress was achieved by the development of both materials synthesis and device fabrication. With the better understanding of the mechanism of the photon-to-electron conversion process in OPV, the commercialization of PSCs could be realized soon. Nowadays, a lot of efforts have been devoted to developing of new donor, acceptor, and interfacial layer materials, optimizing nanostructures of the active layer, fabricating new device architectures, and so on.The development of new donor materials for PSCs is one of the most popular research topics in the field of PSCs and many excellent results have been published. A variety of polymers and SMs have been reported as donor materials for OPVs and some of them might be candidates for the commercialization later. From the reported structures, the conjugated backbones of polymers for OPV can be arbitrarily classified into a few categories based on the constitution of the repeating unit, namely, (a) homopolymers, (b) donor-acceptor polymers, (c) quinoid polymers, and (d) other types of polymers; whereas the SM donors can be classified into the following categories based on their main structures, (a) donor-acceptor type molecules, (b) squaraine dyes, and (c) oligomer and dendrimers.

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Naphthodithiophene-Based Donor–Acceptor Polymers: Versatile Semiconductors for OFETs and OPVs

Cited by 133 publications

References 34 publications

Effects of branching position of alkyl side chains on ordering structure and charge transport property in thienothiophenedione- and quinacridone-based semiconducting polymers

Effects of branching position of alkyl side chains on ordering structure and charge transport property in thienothiophenedione- and quinacridone-based semiconducting polymers

Naphthodithiophene-Based Semiconducting Materials for Applications in Organic Solar Cells

Donor Materials for Organic Solar Cell (OSC)

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