Study of Photoelectric Conversion in Benzotrithiophene-Based Conjugated Semiconducting Polymers

Al-Naamani, Eman; Ide, Marina; Gopal, Anesh; Saeki, Akinori; Osaka, Itaru; Seki, Shu

doi:10.2494/photopolymer.28.605

Cited by 6 publications

(11 citation statements)

References 35 publications

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“…[ 26 ] Seki et al., reported three conjugated polymers (P9–P11) (Figure 3) that contain BTT5 as an electron donor and several thiadiazole acceptors, including TP, FBT and NTz, sandwiched between two octyldecyl(C8/C10) thiophenes. [ 47 ] By increasing the acceptor strength in the polymer backbone, E opt g can be fine‐tuned. The polymers' E opt g values are 1.68 eV for P9, 1.78 eV for P10, and 1.75 eV for P11.…”

Section: Btt‐based Polymers For Oscsmentioning

confidence: 99%

Solution Processable Benzotrithiophene (BTT)‐Based Organic Semiconductors: Recent Advances and Review

Patra

Park

2022

Macromol. Rapid Commun.

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Conjugated polymers and small molecules (SMs) with fused electron‐rich and electron‐deficient building blocks are promising materials for low‐cost organic electronic devices. Benzotrithiophene (BTT) is one such electron‐rich hybrid building block composed of three fused thiophene moieties with an extended π‐system that has been widely used to synthesize a variety of electronic materials. Additionally, BTT has a planar and sulfur‐rich core with a number of distinct advantages, including structural diversity, tunable electro‐optical properties and exceptional hole‐transport behavior. So far, four BTT‐based isomers have been synthesized on a gram scale from seven isomeric structures, three of which are symmetric (BTT1‐3) and one of which is asymmetric (BTT5), for use in a variety of optoelectronic applications. However, no report summarizing the progress of BTT‐based semiconductors for electronic applications is available. The current review presents an overview of the recent developments in BTT‐based monomers, polymers and SMs, as well as their applications in energy harvesting. Additionally, recent advances on charge transport devices, most notably organic solar cells (OSCs), organic thin field‐effect transistors (OTFTs), and perovskite solar cells (Pero‐SCs) are also surveyed and summarized. It is anticipated that this comprehensive review will stimulate further research and development of future BTT‐based electronic materials, particularly for low‐cost and high‐performance organic electronic devices.

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Section: Btt‐based Polymers For Oscsmentioning

confidence: 99%

Solution Processable Benzotrithiophene (BTT)‐Based Organic Semiconductors: Recent Advances and Review

Patra

Park

2022

Macromol. Rapid Commun.

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“…Very recently, the same group synthesized a thienothiophene–NTz polymer system (NT812 and NT1014) . Furthermore, naphthodithiophene (PNNTs, PαNDTDTNT, and PβNDTDTNT), cyclopentadithienothiophene (PCDTT‐NT), and benzotrithiophene (BTT‐NTz) were also incorporated in the NTz polymer system . In addition, a triarylamine unit was incorporated into the NTz polymer system …”

Section: Ntz Polymers With Donor Unitsmentioning

confidence: 99%

“…Saeki and co‐workers synthesized an NTz copolymer with a benzotrithiphene (BTT) moiety, BTT‐NTz (Figure ), and fabricated the solar cell . Although the performance was modest, most likely due to the unoptimized film morphology, the BTT‐NTz cell showed the higher performance than the cell that used BTT polymers with difluorinated BTz and thiadiazolopyridine.…”

Section: Ntz Polymers With Donor Unitsmentioning

confidence: 99%

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

Osaka

Takimiya

2017

Advanced Materials

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Semiconducting polymers can function as both p-type (hole-transporting) and n-type (electron-transporting) materials in those devices. [17][18][19] In OFETs, holes and electrons are injected into the semiconducting polymer at the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), respectively. [10] Those charge carriers are then transported between the source and drain electrodes through the assembled polymer backbones. [20,21] In OPVs, [22] the semiconducting polymer absorbs the sunlight within the polymer absorption range (or the sunlight energy above the polymer bandgap (E g )), generating excitons where the hole and electron are strongly bounded. These excitons then diffuse into the interface of the p-type semiconducting polymer and the n-type material (typically methanofullerenes, [23] but can also be n-type semiconducting polymers [24] or small molecules [25] ), at which the excitons dissociate into free holes and electrons. [23,26,27] Those charge carriers are then transported to the electrodes through the materials domains. Therefore, regardless of the device types, the electronic properties and the charge transport properties are the most important characteristics of the polymers.With respect to the electronic structure, E g and HOMO and LUMO energy levels (E HOMO and E LUMO ) are important parameters for semiconducting polymers. [28] As E g qualitatively indicates the extent of π-electron delocalization along the conjugated backbone, a narrow E g is supposed to be preferable for charge transport, especially along the backbone. E g is more important for OPVs, i.e., a narrow E g is highly desired in order to maximize sunlight harvesting. Deep E HOMO , which refers to large ionization potential (IP), is essential for the p-type semiconducting polymer. This provides oxidative stability of the material [29] as well as higher open-circuit voltage (V OC ) in OPVs that is proportional to the energy difference between the HOMO of the p-type material and LUMO of the n-type material. [30] On the other hand, deep E LUMO , which refers to large electron affinity (EA), is essential for the n-type semiconducting polymer since this offers stable electron transport in ambient conditions. [31] The E LUMO is also important for p-type semiconducting polymers when they are used in OPVs. As narrow E g and deep E HOMO are required for p-type semiconducting poly mers in OPVs, their E LUMO must be deepened. It should be noted, however, the E LUMO of the p-type semiconducting π-Conjugated polymers are an important class of materials for organic electronics. In the past decade, numerous polymers with donor-acceptor molecular structures have been developed and used as the active materials for organic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). The choice of the building unit is the primary step for designing the polymers. Benzochalcogenadiazoles (BXzs) are one of the most familiar acceptor building units studied in this area. As their doubl...

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“…In this work, we report on the effects of the alkyl chains in new conjugated polymers composed of benzobisthiazole (BBT) and NTz (PBBT-NTz). NTz is an analogue of the benchmark BT acceptor in which the π-plane has been extended with a naphthalene unit, and has been copolymerized with various donor moieties for OPV applications. − On the other hand, the weak BBT donor, when incorporated in a BBT-BT polymer , and its difluorinated analogue (PBBT-FBT), exhibited PCEs of 6.5% and 6.4%, respectively. Our interest in this work is the systematic investigation of the role that alkyl chains play in the OPV performance and associated properties of PBBT-NTz polymers.…”

Section: Introductionmentioning

confidence: 99%

Exploring Alkyl Chains in Benzobisthiazole-Naphthobisthiadiazole Polymers: Impact on Solar-Cell Performance, Crystalline Structures, and Optoelectronics

Al-Naamani

Gopal

Ide

et al. 2017

ACS Appl. Mater. Interfaces

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The shapes and lengths of the alkyl chains of conjugated polymers greatly affect the efficiencies of organic photovoltaic devices. This often results in a trade-off between solubility and self-organizing behavior; however, each material has specific optimal chains. Here we report on the effect of alkyl side chains on the film morphologies, crystallinities, and optoelectronic properties of new benzobisthiazole-naphthobisthiadiazole (PBBT-NTz) polymers. The power conversion efficiencies (PCEs) of linear-branched and all-branched polymers range from 2.5% to 6.6%; the variations in these PCEs are investigated by atomic force microscopy, two-dimensional X-ray diffraction (2D-GIXRD), and transient photoconductivity techniques. The best-performing linear-branched polymer, bearing dodecyl and decyltetradecyl chains (C12-DT), exhibits nanometer-scale fibers along with the highest crystallinity, comprising predominant edge-on and partial face-on orientations. This morphology leads to the highest photoconductivity and the longest carrier lifetime. These results highlight the importance of long alkyl chains for inducing intermolecular stacking, which is in contrast to observations made for analogous previously reported polymers.

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Study of Photoelectric Conversion in Benzotrithiophene-Based Conjugated Semiconducting Polymers

Abstract: Benzotrithiophene (BTT), where three thiophenes are fused to a central benzene, was polymerized with three kinds of electron accepting units, thiadiazolopyridine (TP), difluorobenzothiadiazole (FT), or naphthobisthiadiazole (NTz).

Cited by 6 publications

References 35 publications

Solution Processable Benzotrithiophene (BTT)‐Based Organic Semiconductors: Recent Advances and Review

Solution Processable Benzotrithiophene (BTT)‐Based Organic Semiconductors: Recent Advances and Review

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

Exploring Alkyl Chains in Benzobisthiazole-Naphthobisthiadiazole Polymers: Impact on Solar-Cell Performance, Crystalline Structures, and Optoelectronics

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