Fluorodiphenylethene-Containing Donor–Acceptor Conjugated Copolymers with Noncovalent Conformational Locks for Efficient Polymer Field-Effect Transistors

Zhang, Weifeng; Shi, Kai; Huang, Jianyao; Gao, Dong; Mao, Zupan; Li, Dizao; Yu, Gui

doi:10.1021/acs.macromol.6b00144

Cited by 51 publications

(40 citation statements)

References 50 publications

(68 reference statements)

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“…The polymer exhibits typical dual band absorption. The lower energy band in the range of 300–500 nm can be attributed to the internal charge transfer transition and the higher energy band at the range of 500–900 nm is originated from the π–π * transition . The optical band gap of the polymer film is calculated to be 1.44 eV using thin films' absorption onsets.…”

Section: Resultsmentioning

confidence: 99%

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Ding

et al. 2018

Macromol. Rapid Commun.

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A new asymmetric furan and thieno[3,2-b]thiophene flanked diketopyrrolopyrrole (TTFDPP) building block for conjugated polymers is designed and used to generate a donor-acceptor semiconducting polymer, poly[3-(furan-2-yl)-2,5-bis(2-octyldodecyl)-6-(thieno[3,2-b]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-thieno[3,2-b]thiophene] (abbreviated to PTTFDPP-TT), consisting of TTFDPP unit copolymerized with thieno[3,2-b]thiophene comonomer (TT), which is further synthesized. Results demonstrate that PTTFDPP-TT-based thin-film transistors in a bottom-gate bottom-contact device configuration exhibit typical hole-transporting property, with weak temperature dependence for charge carrier mobility from room temperature to 200 °C. In addition, the good solubility of PTTFDPP-TT due to the incorporation of a polar furan unit and an asymmetric conjugated structure makes it able to be solution processed with a less toxic nonchlorinated solvent such as toluene, demonstrating comparable performance with that prepared from chlorinated solution. These results suggest PTTFDPP-TT as a promising organic semiconductor candidate for annealing-free, environmentally benign, and less energy-consuming applications in large-area flexible organic electronic devices.

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Section: Resultsmentioning

confidence: 99%

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Ding

et al. 2018

Macromol. Rapid Commun.

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“…25 The DPP-3FBVCNT-based devices showed almost similar threshold voltages to those of DPP-2FBVCNT-based devices, maybe because of their nearly similar HOMO/LUMO energy levels, which might be due to the similar conformational lock effects from the F…H bonds in the two compounds according to previous research performed by our group. 26,27 From the above results, it can be seen that in these DPP-DBVCNT-based organic conjugated small molecules, the substitution and the position of the F atoms introduced into the benzene rings of the donor units had significant effects on the charge carrier transport. It is interesting to note that the introduction of one F atom into each of the donor benzene rings on both sides of the DPP acceptor unit was beneficial to make the performance of the DPP-BVCNT-based compound be changed from p-type to ambipolar.…”

Section: Charge Carrier Transport Performancementioning

confidence: 86%

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Wang

et al. 2019

Organic Materials

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Based on diketopyrrolopyrrole (DPP) and (E)-3-phenyl-2-(thiophen-2-yl)acrylonitrile (BVCNT)-linked conjugated backbones, three donor–acceptor type conjugated organic small-molecule compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT were designed and synthesized. Among them, the 2-decyltetradecyl side chain on the DPP acceptor unit was used to ensure the solubility of the material. The fluorine (F) atoms combined with the nitrile on the BVCNT donor unit were used to adjust electronic structures and charge carrier transport properties of the conjugated system. All the three small molecules exhibited good solution dispersibility and thermal stability, providing an important guarantee for the solution processing and annealing optimization of organic field-effect transistors (OFETs). The top-gate-bottom-contact OFET devices based on these compounds showed good ambipolar or p-type performances. The relationship between molecular structures and OFET performances indicated that the F-substitution and its position significantly affected their charge carrier transport properties. The F-substitution could remarkably change the performance from p-type to ambipolar especially for the outer-side-F-substituted compound DPP-2FBVCNT, which showed the best OFET performances with the maximum hole/electron mobilities of 0.023/0.220 cm2 V−1 s−1. These results provided a promising idea for developing small-molecule OFET materials with good solution processability, good thermal stability, and high ambipolar performances.

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“…[ 6–8 ] However, the development of ambipolar semiconductors in terms of charge carrier mobility and quantity lags behind that of the unipolar polymer semiconductors. [ 9–12 ] Due to the advance of simplification of the circuit design in complementary circuits, the exploration of high‐performance ambipolar polymer semiconductors becomes one of the major research topics. [ 2,13,14 ]…”

Section: Introductionmentioning

confidence: 99%

Isoindigo (IID)‐Based Semiconductor with F⋯S Interaction Locked Conformation for High‐Performance Ambipolar Bottom‐Gate Top‐Contact Field‐Effect Transistors

Qiao

Wei

2020

Macro Chemistry & Physics

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The development of high‐performance ambipolar polymer semiconductors is critical to organic electronics. Herein, isoindigo (IID)‐based copolymers PIIDDTBT and PIIDDTffBT are synthesized and characterized. Both polymers have suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels for hole and electron injection. Density functional theory calculation reveals F⋯S intramolecular interactions are formed in PIIDDTffBT, which locks the molecular conformation and leads to a more planar backbone. Thin film transistor characterization shows both polymers display ambipolar charge carrier transport behavior. The hole/electron mobilities are 0.29/0.1 cm2 V−1 s−1 for PIIDDTffBT and 0.053/0.013 cm2 V−1 s−1 for PIIDDTBT in the bottom‐gate/top‐contact (BGTC) device structures. The hole/electron mobilities of PIIDDTffBT are one of the highest values for IID‐based ambipolar polymer transistors in BGTC device structure. Atomic force microscopy and X‐ray diffraction results reveal PIIDDTffBT films have higher film quality, crystallinity, and more ordered microstructures, being ascribed to the F⋯S interactions locked backbone. These results demonstrate that the introduction of F⋯S interactions is an effective strategy to design high‐performance ambipolar polymer semiconductors.

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Fluorodiphenylethene-Containing Donor–Acceptor Conjugated Copolymers with Noncovalent Conformational Locks for Efficient Polymer Field-Effect Transistors

Cited by 51 publications

References 50 publications

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Isoindigo (IID)‐Based Semiconductor with F⋯S Interaction Locked Conformation for High‐Performance Ambipolar Bottom‐Gate Top‐Contact Field‐Effect Transistors

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