Synthesis of Narrow Bandgap Polymers based on Benzobis(thiadiazole) and their Application to Organic Transistor Devices

Mamada, Masashi; Uemura, Taisuke; Teraoka, Ryo; Kumaki, Daisuke; Tokito, Shizuo

doi:10.2494/photopolymer.27.321

Cited by 2 publications

(2 citation statements)

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“…Therefore, we first calculated the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) and the excited states of the first singlet and first triplet for the model oligomers F1-(BT-F1) n with n = 1–6, where F1 represents 9,9-dimethylfluorene, and the calculated values were then plotted versus 1/ n (Methods S1, Figure S1, and Table S2). The estimated properties of the polymer were then obtained by extrapolation to n = ∞. , The oligomer with n = 3 showed a small difference of ca. 0.1 eV for the HOMO–LUMO gap and the excited state energies versus the estimated results for the polymer.…”

Section: Results and Discussionmentioning

confidence: 99%

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F8BT Oligomers for Organic Solid-State Lasers

Mamada

Komatsu

Adachi

2020

ACS Appl. Mater. Interfaces

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The yellow-green emissive poly(9,9-dioctylfluorenealt-benzothiadiazole) (F8BT) polymer is widely used because of its suitability for a variety of applications. However, we have found that F8BT shows huge performance variations that depend on the chemical supplier, with photoluminescence quantum yields (PLQYs) ranging from 7 to 60% in neat films. Polymers generally face problems including purity, polydispersity, and reproducibility, which also affect F8BT polymers. Therefore, to overcome these problems, we investigated oligomers of F8BT, which can easily be purified and can thus be obtained in a high-purity form. In the three oligomers (M1−M3) that we synthesized, the PLQYs were much higher than those of conventional F8BT (>80% in their neat films) although their PL spectra were nearly the same as that of F8BT, and their amplified spontaneous emission (ASE) thresholds were lower than that of the polymer (e.g., 1.9 μJ cm −2 for M3 and 2.7 μJ cm −2 for F8BT) because of a higher net gain and better film morphology. Furthermore, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies of the oligomers were found to be similar to those of F8BT, making them candidate materials for use as hosts in light-emitting devices. The ASE using a near-infrared laser emitter doped in F8BT and oligomer hosts showed a clear difference despite nearly the same properties for steady-state emission.

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Section: Results and Discussionmentioning

confidence: 99%

“…The estimated properties of the polymer were then obtained by extrapolation to n = ∞. 31,32 The oligomer with n = 3 showed a small difference of ca. 0.1 eV for the HOMO−LUMO gap and the excited state energies versus the estimated results for the polymer.…”

Section: ■ Introductionmentioning

confidence: 99%

F8BT Oligomers for Organic Solid-State Lasers

Mamada

Komatsu

Adachi

2020

ACS Appl. Mater. Interfaces

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Polarity Engineering of Benzobisthiadiazole-Based Polymer Thin Film Transistors by Variation of Electron Affinity of the Comonomers

Wang

Hosokawa

Mori

et al. 2017

Bulletin of the Chemical Society of Japan

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Fine-tuning of the charge carrier polarity in organic transistors is a fundamental task in order to achieve high-performance organic complementary circuits and related devices. In this article, an efficient methodology for tuning the polarity via rational molecular design is reported. We systematically adjusted the electron affinity of the comonomers in semiconducting copolymers. Thus, three comonomer units, thiophene (T), vinylene (V), and benzothiadiazole (BT), were combined with the benzobisthiadiazole (BBT) unit, leading to three new BBT-based copolymers; i.e., pBBT-T, pBBT-V, and pBBT-BT, respectively. We found that the electron affinity of the comonomer unit decisively affects the absorption spectra, energy levels, thin-film microstructures, and, accordingly, the charge-carrier polarity of the copolymers. pBBT-T with the electron-rich thiophene comonomer showed balanced ambipolar transistor characteristics with the electron/hole mobility ratio (μe/μh) of 2. In contrast, the electron dominant ambipolar characteristics of μe/μh = 14 were achieved by combining BBT with the electron-neutral vinylene group for pBBT-V. Intriguingly, by further strengthening the electron-accepting properties by using the BT unit, unipolar n-type transistors were successfully fabricated based on pBBT-BT. As a result, our findings demonstrated a promising methodology for constructing organic complementary circuits by variation of the electron affinity of the comonomers in BBT-based semiconducting polymers.

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Synthesis of Narrow Bandgap Polymers based on Benzobis(thiadiazole) and their Application to Organic Transistor Devices

Cited by 2 publications

References 24 publications

F8BT Oligomers for Organic Solid-State Lasers

F8BT Oligomers for Organic Solid-State Lasers

Polarity Engineering of Benzobisthiadiazole-Based Polymer Thin Film Transistors by Variation of Electron Affinity of the Comonomers

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