A new thieno-isoindigo derivative-based D–A polymer with very low bandgap for high-performance ambipolar organic thin-film transistors

Zhang, Guobing; Ye, Zhiwei; Guo, Jinghua; Wang, Qinghe; Tang, Longxiang; Lu, Hongbo; Qiu, Longzhen

doi:10.1039/c5py00161g

Cited by 37 publications

(23 citation statements)

References 39 publications

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“…Isoindigo was first utilized for constructing donor materials by Reynolds and co‐workers in 2010 and later the first isoindigo‐based copolymers with large charge mobilities (more than 0.7 cm 2 V −1 s −1 for holes) were put forward by Pei and co‐workers . During the past few years, scientists have created several novel isoindigo‐based acceptor units (namely, BDOPV, NBDOPV, INDF, and DIID) by inserting various functional groups inside isoindigos to extend their conjugation lengths and reduce LUMO levels and energy gaps . Zhou et al reported solution‐processable copolymers by employing BDOPV as strong acceptor units for lower LUMOs and thieno[3,2‐ b ]thiophene as donor moieties for regulating HOMOs ( Figure a) .…”

Section: Ambipolar Organic Semiconducting Materialsmentioning

confidence: 99%

Recent Advances in Ambipolar Transistors for Functional Applications

Ren

Yang

Zhou

et al. 2019

Adv Funct Materials

164

139

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Ambipolar transistors represent a class of transistors where positive (holes) and negative (electrons) charge carriers both can transport concurrently within the semiconducting channel. The basic switching states of ambipolar transistors are comprised of common off-state and separated on-state mainly impelled by holes or electrons. During the past years, diverse materials are synthesized and utilized for implementing ambipolar charge transport and their further emerging applications comprising ambipolar memory, synaptic, logic, and light-emitting transistors on account of their special bidirectional carrier-transporting characteristic. Within this review, recent developments of ambipolar transistor field involving fundamental principles, interface modifications, selected semiconducting material systems, device structures, ambipolar characteristics, and promising applications are highlighted. The existed challenges and prospective for researching ambipolar transistors in electronics and optoelectronics are also discussed. It is expected that the review and outlook are well timed and instrumental for the rapid progress of academic sector of ambipolar transistors in lighting, display, memory, as well as neuromorphic computing for artificial intelligence.

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Section: Ambipolar Organic Semiconducting Materialsmentioning

confidence: 99%

Recent Advances in Ambipolar Transistors for Functional Applications

Ren

Yang

Zhou

et al. 2019

Adv Funct Materials

164

139

View full text Add to dashboard Cite

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“…When the outer benzene rings in IBDT indolinone moieties were replaced by thiophene rings, the resulting monomer in P102 featured a more planar backbone due to the S/O interaction. 107 In comparison with its reference polymer and analog polymer P100, the thiophene replacement provided the P102 with a lowered LUMO energy level and enhanced HOMO energy level, leading to its ultra-narrow band gap of 0.71 eV. Besides, the annealed P102 lm showed a large and continuous nano-brillar structure, with an interconnected network, rather than clustered crystals in its as-cast lm (Fig.…”

Section: Chemical Science Reviewmentioning

confidence: 97%

Recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells

Zhou

Zhang

2021

Chem. Sci.

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“…Different from the unipolar electron transport characterization of its M5 counterpart, P22 exhibited ambipolar transport characterization. [ 100 ] Besides, aza‐ M5 was also synthesized to further improve the molecular planarity and lower the energy levels. Several polymers based on aza‐ M5 exhibited high charge carrier mobilities.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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A new thieno-isoindigo derivative-based D–A polymer with very low bandgap for high-performance ambipolar organic thin-film transistors

Abstract: A new thieno-isoindigo derivative was synthesized by replacing the outer benzene ring of the isoindigo derivative (BIBDF) with thiophene.

Cited by 37 publications

References 39 publications

Recent Advances in Ambipolar Transistors for Functional Applications

Recent Advances in Ambipolar Transistors for Functional Applications

Recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

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