Synthesis of donor–acceptor copolymer using benzoselenadiazole as acceptor for OTFT

Shaik, Baji; Han, Jin‐Hee; Song, Dong Jin; Kang, Hun-Min; Kim, Ye Beyeol; Park, Jin Young; Lee, Sang‐Gyeong

doi:10.1039/c5ra23805f

Cited by 12 publications

(5 citation statements)

References 34 publications

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“…These values are translated into quite low-lying HOMO energy levels, conferring stability against atmospheric oxygen to the structure while also being suitable for hole injection. The energy of the optical band gaps (E gap ) was estimated to be 3.22 eV in all three cases, which is smaller than that of the bare triindole system (3.53 eV [20]) because of the more extended π-conjugation of the system. The ionization potentials were also estimated in the solid state though the photoelectron emission technique as a closer Coatings 2023, 13, 896 6 of 13 approximation of the device conditions.…”

Section: Physical Characterizationmentioning

confidence: 68%

“…Apart from the key 2 of 13 role of the main aromatic nucleus, however, additional structural features can be equally decisive in governing the semiconductor characteristics of a material. A prime example of this is the inclusion of flexible alkyl chains, which not only improve the solubility but also influence the intermolecular interactions in the solid state [16][17][18][19][20]. Therefore, the alkylation patterning in a particular core should be carefully addressed to extract its full potential in terms of charge carrier mobility.…”

Section: Introductionmentioning

confidence: 99%

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Role of the Alkylation Patterning in the Performance of OTFTs: The Case of Thiophene-Functionalized Triindoles

et al. 2023

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Organic semiconductors have emerged as potential alternatives to conventional inorganic materials due to their numerous assets and applications. In this context, the star-shaped triindole core stands as a promising system to design new organic materials with enticing charge-transporting properties. Herein, we present the synthesis of three thiophene-containing triindole derivatives that feature N-alkyl chains of different lengths, from methyl to decyl. The impact of the alkylation patterning on the crystallinity of the thin films and their resultant performance as semiconductor have been analyzed. All derivatives displayed p-type semiconductor properties, as demonstrated via both TOF measurements and integration in organic thin-film transistor (OTFT) devices. The attachment of longer alkyl chains and the functionalization of the silicon substrate with octadecyltrichlorosilane (OTS) prompted better OTFT characteristics, with a hole mobility value up to 5 × 10−4 cm2 V−1 s−1. As elucidated from the single crystal, this core is arranged in a convenient cofacial packing that maximizes the π-overlapping. The analysis of the thin films also corroborates that derivatives possessing longer N-alkyl chains confer a higher degree of order and a more adequate morphology.

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Section: Physical Characterizationmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Role of the Alkylation Patterning in the Performance of OTFTs: The Case of Thiophene-Functionalized Triindoles

et al. 2023

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“…The donor–acceptor molecules have a low energy gap between the HOMO and LUMO levels. The common electron acceptor molecules are benzothiadiazole [ 28 ], benzoselenadiazole [ 29 ], and diketopyrrolopyrrole [ 30 ], while the common electron donor molecules are thiophene [ 31 ], 3,4-ethylenedioxythiophene [ 32 ], and thienothiophene [ 33 ]. Although many acceptor molecules have been explored for OFETs, diketopyrrolopyrrole remains one of the most versatile and widely used molecules.…”

Section: Introductionmentioning

confidence: 99%

A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units

et al. 2021

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A-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-T) and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-EDOT) have been designed and synthesized. The diketopyrrolopyrrole acts as an electron acceptor, while the thiophene or 3,4-ethylenedioxythiophene acts as an electron donor. The donor–acceptor groups are connected by an ethynyl bridge to further enhance the conjugation. The optoelectronics, electrochemical, and thermal properties have been investigated. Organic thin film transistor (OTFT) devices prepared from TDPP-T and TDPP-EDOT have shown p-type mobility. In as cast films, TDPP-T and TDPP-EDOT have shown a hole mobility of 5.44 × 10−6 cm2 V−1 s−1 and 4.13 × 10−6 cm2 V−1 s−1, respectively. The increase in the mobility of TDPP-T and TDPP-EDOT OTFT devices was observed after annealing at 150 °C, after which the mobilities were 3.11 × 10−4 cm2 V−1 s−1 and 2.63 × 10−4 cm2 V−1 s−1, respectively.

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“…Recently, selenium-based electron-rich heteroaromatic building blocks such as selenophene, benzodiselenophene, and selenolo[3,2- b ]thiophene were employed to build conjugated polymers for polymer solar cells [ 23 ] and organic field-effect transistors [ 24 ]. The incorporation of Se atom in polymer backbone reduces the bandgap and absorbs red light region of the solar spectrum.…”

Section: Introductionmentioning

confidence: 99%

Novel Two-Dimensional Conjugated Polymer Containing Fluorinated Bithiophene as Donor and Benzoselenodiazole as Acceptor Units with Vinyl-Terthiophene Pendants for Polymer Photovoltaic Cells

et al. 2017

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Novel two-dimensional conjugated copolymer, abbreviated as PDTBSeVTT-2TF, containing electron-deficient 4,7-di(thiophen-2-yl)benzo[c][1,2,5]selenodiazole (DTBSe) unit, conjugated vinyl-terthiophene (VTT) side chain and 3,3′-difluoro-2,2′-bithiophene (2TF) was designed and synthesized using microwave-assisted Stille cross-coupling polymerization. UV–visible absorption and cyclic voltammetry studies revealed that this copolymer possesses a strong and broad absorption in the range of 300–800 nm and a narrow optical bandgap (Eg) of 1.57 eV with low-lying HOMO and LUMO energy levels. Further, the bulk heterojunction polymer solar cells (PSCs) were fabricated using PDTBSeVTT-2TF as donor and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptor with an inverted device structure of ITO/ZnO/PDTBSeVTT-2TF:PC71BM/V2O5/Ag. The processing temperature of blend solution for preparing PDTBSeVTT-2TF:PC71BM active layer showed obvious impact on the photovoltaic performance of solar devices. The cell fabricated from the blend solution at 65 °C exhibited enhanced power conversion efficiencies (PCE) of 5.11% with a Jsc of 10.99 mA/cm−2 compared with the one at 50 °C, which had a PCE of 4.69% with a Jsc of 10.10 mA/cm−2. This enhancement is due to the dissolution of PDTBSeVTT-2TF clusters into single molecules and small aggregates, improving the miscibility between the polymer and PC71BM and thus increasing the donor/acceptor interface.

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Synthesis of donor–acceptor copolymer using benzoselenadiazole as acceptor for OTFT

Abstract: The synthesized copolymer has a low band gap and exhibits a hole mobility of around 0.1 cm2 V−1 s−1.

Cited by 12 publications

References 34 publications

Role of the Alkylation Patterning in the Performance of OTFTs: The Case of Thiophene-Functionalized Triindoles

Role of the Alkylation Patterning in the Performance of OTFTs: The Case of Thiophene-Functionalized Triindoles

A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units

Novel Two-Dimensional Conjugated Polymer Containing Fluorinated Bithiophene as Donor and Benzoselenodiazole as Acceptor Units with Vinyl-Terthiophene Pendants for Polymer Photovoltaic Cells

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