Tunable charge-transport polarity in thienothiophene–bisoxoindolinylidene-benzodifurandione copolymers for high-performance field-effect transistors

Chen, Zhihui; Huang, Jianyao; Zhang, Weifeng; Zhou, Yankai; Wei, Xuyang; Wei, Jinbei; Zheng, Yuanhui; Wang, Liping; Yu, Gui

doi:10.1039/d1tc02833b

Cited by 6 publications

(4 citation statements)

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“…127 Apart from the strong electron-deficient nature, the structure of IID is easy to be modified and derived in comparison with DPP, NDI, and BT units. 128–130 The structural feature of IID endows itself with multiple modification sites, such as the phenyl groups, the center carbon–carbon double bonds, and lactam nitrogen atoms. In order to further improve the performances of organic semiconductor materials, various IID derivatives have been synthesized by using some modification methods including the introduction of side chains on the lactam nitrogen atoms, the substitution of heterocycles for benzene rings, and conjugated extension of double bonds or benzene rings.…”

Section: Semiconducting Polymers Based On Diarylethylene Unitsmentioning

confidence: 99%

Synthetic strategies, molecular engineering and applications of semiconducting polymers based on diarylethylene units in electronic devices

Zhang

Wang

et al. 2022

J. Mater. Chem. C

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Section: Semiconducting Polymers Based On Diarylethylene Unitsmentioning

confidence: 99%

Synthetic strategies, molecular engineering and applications of semiconducting polymers based on diarylethylene units in electronic devices

Zhang

Wang

et al. 2022

J. Mater. Chem. C

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“…邱龙臻等 [36] 基于这种策略改造了 DAII 受体单元, 合成上通过溴代吡啶靛红( 17 于贵等 [37] 将 BABDF ( 56 于贵等 [38] 耿延候等 [39] 合成了双异靛蓝(bis-IID)受体单元, 并基于 DAII 合成了一系列聚合物主链中含氟和氮原子的聚合. P2N2F-BT (64)和 P2N2F-4FBT (65)的 HOMO/ LUMO 能级分别为-3.88/-5.67 eV 和-4.01/-6.06 eV [40] , F 原子的引入极大地降低了 HOMO/LUMO 能级.…”

Section: Daii 及其衍生物在光电材料领域的应用unclassified

“…由于 DAII 受体单元的 LUMO 能级相对较低, 对于其受体单元的改造主要集中在构筑 n 传输材料上, 通过对 DAII 受体单元有效共轭长度的增加, 以及强吸电子基团, 如氟原子的引入, 进一步将 DAII 受体单元的 LUMO 能级降低到了-4.0 eV 以下, 提升电子迁移率, 对于构筑 n 型传输材料均具有重要意义. 供电子基团的引入略微提升了 DAII 受体单元的 LUMO 能级, 将原本表现出 n 型传输的材料转变为了双极性传输 [38] .…”

Section: 联噻吩上引入的氟原子使得电荷传输类型从双极型传输向unclassified

Synthesis of Nitrogen-Containing Isoindigo Derivatives and Their Applications in Optoelectronic Materials

Luo¹,

Li²,

Mu³

et al. 2022

Chinese Journal of Organic Chemistry

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Isoindigo has played an important role in organic optoelectronic materials as an excellent acceptor building block due to its planarity and electron-withdrawing capability. The modification, of isoindigo has also become the focus of academia. Recently, great achievements have been made in the synthesis of nitrogen-containing isoindigo derivatives and their applications as optoelectronic materials. The incorporation of nitrogen atom can further adjust the electron push/pull ability and the planarity of isoindigo derivatives, thereby tune their optoelectronic properties. The development of nitrogen-containing isoindigo derivatives, as well as their applications in optoelectronic materials, which we hope would provide useful information for the design of conjugated optoelectronic materials, is summarized. Keywords nitrogen-containing isoindigo; organic optoelectronic materials; polymer field effect transistors 21 世纪初, 异靛蓝结构作为有机光电材料的受体单元首次映入人们眼帘, Reynolds 等异靛蓝具有良好的对称性, 该结构中所含有的两个内酰胺可形成较强的分子间氢键 [5] , 可作为构象锁来提升异靛蓝结构的平面性 [6] , 使得异靛蓝保持一个相对平面的结构. 目前, 基于异靛蓝作为受体的第三代聚合物

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“…In the majority of cases, they are low band gap semiconductors exhibiting appropriate ionization potential (IP) and electron affinity (EA) values to assure their ambipolarity. As a result, they can serve as components of active layers in various types of ambipolar organic field-effect transistors, characterized by well-balanced n-type and p-type electrical transport [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. Low ionization potential (IP) and high electron affinity (EA) of D–A and D–A–D polymers, together with the presence of several chromophore groups, promote their reversible electrochemical and spectroelectrochemical behavior [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Copolymers Containing 1-Methyl-2-phenyl-imidazole Moieties as Permanent Dipole Generating Units: Synthesis, Spectroscopic, Electrochemical, and Photovoltaic Properties

et al. 2022

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New donor–acceptor conjugated alternating or random copolymers containing 1-methyl-2-phenylbenzimidazole and benzothiadiazole (P1), diketopyrrolopyrrole (P4), or both acceptors (P2) are reported. The specific feature of these copolymers is the presence of a permanent dipole-bearing moiety (1-methyl-2-phenyl imidazole (MPI)) fused with the 1,4-phenylene ring of the polymer main chain. For comparative reasons, polymers of the same main chain but deprived of the MPI group were prepared, namely, P5 with diketopyrrolopyrrole and P3 with both acceptors. The presence of the permanent dipole results in an increase of the optical band gap from 1.51 eV in P3 to 1.57 eV in P2 and from 1.49 eV in P5 to 1.55 eV in P4. It also has a measurable effect on the ionization potential (IP) and electrochemical band gap (EgCV), leading to their decrease from 5.00 and 1.83 eV in P3 to 4.92 and 1.79 eV in P2 as well as from 5.09 and 1.87 eV in P5 to 4.94 and 1.81 eV in P4. Moreover, the presence of permanent dipole lowers the exciton binding energy (Eb) from 0.32 eV in P3 to 0.22 eV in P2 and from 0.38 eV in P5 to 0.26 eV in P4. These dipole-induced changes in the polymer properties should be beneficial for photovoltaic applications. Bulk heterojunction solar cells fabricated from these polymers (with PC71BM acceptor) show low series resistance (rs), indicating good electrical transport properties. The measured power conversion efficiency (PCE) of 0.54% is limited by the unfavorable morphology of the active layer.

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Tunable charge-transport polarity in thienothiophene–bisoxoindolinylidene-benzodifurandione copolymers for high-performance field-effect transistors

Abstract: N-type semiconducting polymers are important materials for modern electronics but limited in variety and performance. To design a new n-type polymer semiconductor requires a judicious trade-off between structural parameters involving...

Cited by 6 publications

References 40 publications

Synthetic strategies, molecular engineering and applications of semiconducting polymers based on diarylethylene units in electronic devices

Synthetic strategies, molecular engineering and applications of semiconducting polymers based on diarylethylene units in electronic devices

Synthesis of Nitrogen-Containing Isoindigo Derivatives and Their Applications in Optoelectronic Materials

Copolymers Containing 1-Methyl-2-phenyl-imidazole Moieties as Permanent Dipole Generating Units: Synthesis, Spectroscopic, Electrochemical, and Photovoltaic Properties

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