Synthesis of novel conjugated polymers based on benzo[1,2-<i>d</i>:4,5-<i>d</i>′]-bis([1,2,3]triazole) for applications in organic field-effect transistors

Yeh, Yao Ming; Huang, Chiao Hui; Peng, Shih Hao; Chang, Chia Chih; Hsu, Chain‐Shu

doi:10.1039/c8py01526k

Cited by 12 publications

(6 citation statements)

References 49 publications

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“…[ 5–10 ] Among tremendous efforts to elevate their device performances, the material design of new CPs with novel molecular structures and ideal physicochemical properties serves as the cornerstone for the success of the organic electronic areas. [ 11–14 ] Specifically, the backbone structures of CPs, not only has a crucial effect on the intramolecular π‐orbital overlap and delocalization, but also play an important role for enhancing the inter‐(macro)molecular interactions via π–π stacking. [ 15,16 ] Therefore, numerous strategies of tailoring the backbone structures of CPs such as quinoidalization, ladderization, incorporation of non‐covalent interactions, or simply π‐extension of the building blocks within main chains have been applied for the ultimate purpose of delivering high performances in different organic electronic devices.…”

Section: Introductionmentioning

confidence: 99%

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Dai

Zheng

et al. 2021

Macromol. Rapid Commun.

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For polymer semiconductors, the backbone structure plays an essential role in determining their physicochemical properties and charge transport behaviors. In this work, two donor–acceptor‐type polymers (P‐BDF and P‐NDF) based on benzodifuranone (BDF) and naphthodifunarone (NDF) as electron‐deficient moieties and indaceno‐dithiophene as electron‐rich groups are designed, synthesized and, for the first time, applied in organic field‐effect transistor. P‐BDF and P‐NDF differ from their backbone structures while P‐BDF has a more planar backbone conformation due to its smaller conjugated core size and P‐NDF features a perpendicular‐extended main chain structure. As a result, P‐BDF polymer exhibits bathochromic optical absorption, deeper molecular orbital energy levels, and more importantly, closer π‐stacking and stronger aggregation in the solid state and thus affords a more promising hole mobility of up to 0.85 cm2 V−1 s−1 in OFET devices, while that of the P‐NDF‐based devices is only 0.55 cm2 V−1 s−1. The results suggest the great potential of BDF/NDF‐type chromophores in constructing novel organic semiconductors and also indicate that the main chain coplanarity of polymer semiconductors is more essential than the sole extension of π‐conjugations (especially at the perpendicular direction of polymer main chains) for the design of high‐performance OFET materials.

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Section: Introductionmentioning

confidence: 99%

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Dai

Zheng

et al. 2021

Macromol. Rapid Commun.

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“…Herein, we synthesized a series of polymers using the proquinoid 2,6-dialkyl-benzo[1,2- d ;4,5- d ′]bistriazole (BBTa26) moiety. According to density functional theory (DFT) calculations, the BBTa26 moiety is a weak acceptor with proquinoidal structure that can form highly coplanar geometry with thiophene π-spacer groups − and can be made highly soluble by the incorporation of solubilizing groups. Single-crystal X-ray diffraction of 2,6-dihexyl-4,8-bis(2-thienyl)-BBTa26 also revealed a small dihedral angle of 4.9° and a short C–C bond of 1.446 Å between the BBTa26 core and thiophene .…”

Section: Introductionmentioning

confidence: 99%

Proquinoidal-Conjugated Polymer as an Effective Strategy for the Enhancement of Electrical Conductivity and Thermoelectric Properties

Tam

Lim

et al. 2019

Chem. Mater.

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P-doping of conjugated polymers requires electron transfer from the conjugated polymer to the p-dopant. This implies that the highest occupied molecular orbital (HOMO) of the conjugated polymer has to be higher than the lowest unoccupied molecular orbital (LUMO) of the p-dopant. Although commonly used p-dopants such as 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ) have a low LUMO of −5.24 eV, most conjugated polymers used in high-performance field-effect transistors are donor–acceptor-type polymers with deep HOMO values, making them difficult to be effectively doped by F4TCNQ. Here, we utilized the proquinoidal 2,6-dialkyl-benzo[1,2-d;4,5-d′]bistriazole (BBTa26) moiety in conjugated polymers to destabilize HOMO, allowing effective p-doping using very dilute F4TCNQ solutions. The extent of the quinoidal character and hence their intrinsic conductivities and the ability to be doped are dependent on the dihedral angles and aromaticity of the aryl spacer groups along the polymer backbone. Intrinsic conductivities as high as 10–2 S cm–1 were achieved. Upon doping using F4TCNQ, highly delocalized polarons were observed. As such, electrical conductivities of over 100 S cm–1 and an enhancement of the Seebeck coefficient from carrier-induced softening can be achieved. A maximum power factor of 11.8 μW m–1 K–2 was achieved in thin-film thermoelectric devices. These results are among the highest for solution-phase p-doping using F4TCNQ without additional processing.

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“…This has been addressed by the fusion of additional heterocycles in the 5,6‐positions of the BTz ring. [ 25–29 ] Alternatively, additional electron‐withdrawing groups such as fluorine or nitrile can be added to the BTz to increase the acceptor strength. Such derivatives have been extensively used in the development of polymers for OPV devices, [ 30–34 ] while there has been comparatively less work on the use of BTz as a co‐monomer in materials for transistor applications.…”

Section: Introductionmentioning

confidence: 99%

A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

Aniés

Wang

Hodsden

et al. 2020

Adv Elect Materials

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A straightforward synthesis is reported for four structurally simple donor–acceptor conjugated polymers based on an alkylated difluorobenzotriazole and either unsubstituted bithiophene (T2) or thienylvinylthiophene (TVT) co‐monomers. Two solubilizing sidechains are investigated in which the position of the branching point is moved away from the conjugated backbone. Optoelectronic measurements and density functional theory calculations show very similar energetic properties between the polymers, with a slightly narrower bandgap for the vinylene incorporating TVT polymers as a result of extended conjugation. Transistor measurements demonstrate that the simplest polymer, containing a readily available 2‐decyltetradecyl sidechain with a T2 co‐monomer, exhibits the best device performance, with an average saturated mobility of 0.2 cm2 V−1 s−1.

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Synthesis of novel conjugated polymers based on benzo[1,2-d:4,5-d′]-bis([1,2,3]triazole) for applications in organic field-effect transistors

Abstract: New conjugated polymers based on 4,8-bis(5-bromothiophen-2-yl)-2,6-bis(2-octyldodecyl)-2H-benzo[1,2-d:4,5-d′]- bis([1,2,3]triazole)-6-ium-5-ide (BTBBTa) displayed the highest hole mobility of 0.21 cm2 V−1 s−1.

Cited by 12 publications

References 49 publications

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Proquinoidal-Conjugated Polymer as an Effective Strategy for the Enhancement of Electrical Conductivity and Thermoelectric Properties

A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

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