Naphthodipyrrolidone (NDP) based conjugated polymers with high electron mobility and ambipolar transport properties

Zhang, Haichang; Zhang, Shuo; Mao, Yifan; Liu, Kewei; Chen, Yu Ming; Jiang, Zhang; Strzalka, Joseph; Yang, Wenjun; Wang, Chien‐Lung; Zhu, Yu

doi:10.1039/c7py00616k

Cited by 22 publications

(14 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Over the past several decades, organic conjugated polymers (CPs) with inorganic silicon‐like semiconducting behaviors have attracted more and more attentions from the scientific community due to their intriguing properties of mechanical flexibility and solution processability. [ 1–4 ] A great material library of new CPs have been established, which together with surface engineering of the device interfacial layers and optimization of device fabrication procedures, have led to significant improvements of device performances in many electronic applications such as organic thin‐film transistors (OFETs), organic solar cells (OSCs), and so on. [ 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.…”

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.

Self Cite

View full text Add to dashboard Cite

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.

show abstract

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.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Compared to the isoDPP, the BDP, and NDP showed similar chemical structures except the core are tri-and tera-cyclic (Deng et al, 2019). Rumer et al reported BDP based polymers with ambipolar behavior with µ h and µ e of 0.2 and 0.1 cm 2 V −1 s −1 , respectively (Rumer et al, 2013) (Figure 2F), while a similar polymer consisting of NDP based polymer exhibited n-type behavior with µ e of 0.67 cm 2 V −1 s −1 (Zhang et al, 2017b) (Figure 2G). The different properties of these semiconductors could be due to the fact that the π-conjugation extension could not only enlarge the charge transfer pathway, but also adjust the frontier molecular orbitals.…”

Section: Dpp-based Derivativesmentioning

confidence: 84%

Diketopyrrolopyrrole Based Organic Semiconductor Materials for Field-Effect Transistors

Zou

Cui

et al. 2021

Front. Chem.

View full text Add to dashboard Cite

Over the past several decades, organic conjugated materials as semiconductors in organic field effect transistors (OFETs) have attracted more and more attention from the scientific community due to their intriguing properties of mechanical flexibility and solution processability. However, the device fabrication technique, design, and synthesis of novel organic semiconductor materials with high charge carrier mobility is crucial for the development of high-performance OFETs. In the past few years, more and more novel materials were designed and tested in the OFETs. Among which, diketopyrrolopyrrole (DPP) and its derivatives, as the electron acceptors to build donor-acceptor (D-A) typed materials, are the perspective. In this article, recently reported molecules regarding the DPP and its derivatives for OFETs application are reviewed. In addition, the relationship between the chemical structures and the performance of the device are discussed. Furthermore, an outlook of DPP-based materials in OFETs with a future design concept and the development trend are provided.

show abstract

“…Soon after, the same group used P47 to construct OFET showing ambipolar semiconducting behavior with a μ h of 0.015 cm 2 V −1 s −1 and an μ e of 0.227 cm 2 V −1 s −1 . In this work, another polymer (P41) using bithiophene as donor unit was synthesized, which showed an μ e of even up to 0.667 cm 2 V −1 s −1 [83]. The charge carrier mobility was only one order magnitude lower when the device was exposed in air after one week.…”

Section: Polymersmentioning

confidence: 99%

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Deng

et al. 2019

Polymers

Self Cite

View full text Add to dashboard Cite

π-Conjugated organic donor–acceptor (D–A) type polymers are widely developed and used in electronic device. Among which, diketopyrrolopyrrole (DPP)-based polymers have received the most attention due to their high performances. The novel chromophores named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), benzodipyrrolidone (BDP) and naphthodipyrrolidone (NDP) are resemble DPP in chemical structure. IsoDPP is an isomer of DPP, with the switching position of carbonyl and amide units. The cores of BDP and NDP are tri- and tetracyclic, whereas isoDPP is bicyclic. π-Conjugation extension could result polymers with distinct optical, electrochemical and device performance. It is expected that the polymers containing these high-performance electron-deficient pigments are potential in the electronic device applications, and have the potential to be better than the DPP-based ones. IsoDPP, BDP, and NDP based polymers are synthesized since 2011, and have not receive desirable attention. In this work, the synthesis, properties (optical and electrochemical characteristics), electronic device as well as their relationship depending on core-extension or structure subtle optimization have been reviewed. The final goal is to outline a theoretical scaffold for the design the D–A type conjugated polymers, which is potential for high-performance electronic devices.

show abstract

Naphthodipyrrolidone (NDP) based conjugated polymers with high electron mobility and ambipolar transport properties

Abstract: Conjugated polymers based on NDP were synthesized and characterized. The polymer thin film organic field effect transistor exhibited ambipolar transport properties with an electron mobility up to 0.67 cm2 V−1 s−1.

Cited by 22 publications

References 39 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

Diketopyrrolopyrrole Based Organic Semiconductor Materials for Field-Effect Transistors

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Contact Info

Product

Resources

About