Diketopyrrolopyrrole-Containing Quinoidal Small Molecules for High-Performance, Air-Stable, and Solution-Processable n-Channel Organic Field-Effect Transistors

Qiao, Yali; Guo, Yunlong; Yu, Chunmeng; Zhang, Fengjiao; Xu, Wei; Liu, Yunqi; Zhu, Daoben

doi:10.1021/ja3003183

Cited by 293 publications

(211 citation statements)

References 37 publications

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“…2. To help promote planarity of the derivatives, the electron-withdrawing moieties [18][19][20][21][22] were introduced using Sonogashira-coupling reactions of DPP-Br 2 and 4-ethynylbenzaldehyde. 23 Further, Knoevenagel condensation of DPP-BZ with 2-ethylhexyl-2-cyanoacetate and N-(2-ethylhexyl)-2-cyanoacetamide afforded DPP-ES and DPP-AM, respectively.…”

Section: Resultsmentioning

confidence: 99%

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

et al. 2015

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Abstract. The synthesis and characterization of three solution processable diketopyrrolopyrrole (DPP) derivatives featuring acceptor units attached to the core by alkyne linker units is reported. Cyclic voltammetry and density functional theory calculations indicate that the DPP derivatives possess similar HOMO and LUMO energies. Solar cells were fabricated by blending the synthesized DPP derivatives with [6,6]-phenyl-C71-butyrate methyl ester. The influence of donor: acceptor blend ratio, film thickness, annealing temperature, and annealing time on device performance was studied. Differences in device performance were related to atomic force microscopy measurements of the films. The highest power conversion efficiency of 1.76% was achieved for the DPP derivative functionalized with an aldehyde electron-withdrawing group with a 1∶0.7 donor:acceptor ratio when the active layer was annealed for 10 min at 110°C.

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Section: Resultsmentioning

confidence: 99%

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

et al. 2015

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“…Qiao et al have increased the DPP backbone planarity and electron affinity by covalently linking DPP with dicyanomethane to obtain electron mobilities of 0.55 cm 2 V -1 s -1 . 17 Semiconductor-dielectric interface modifications by self-assembly techniques and usage of low work function top electrodes can effectively extract electrons. 8,18 Side chain engineering has been shown to be pivotal in altering molecular packing and backbone torsional conformations.…”

Section: Introductionmentioning

confidence: 99%

Air-Stable n-channel Diketopyrrolopyrrole−Diketopyrrolopyrrole Oligomers for High Performance Ambipolar Organic Transistors

Mukhopadhyay

Puttaraju

Senanayak

et al. 2016

ACS Appl. Mater. Interfaces

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Abstract:N-type organic semiconductors are prone to oxidation upon exposed to ambient conditions. Herein, we report design and synthesis of diketopyrrolopyrrole (DPP) based oligomers for ambipolar organic thin film transistors (OFETs) with excellent air and bias stability at ambient conditions. The cyclic voltammetry measurements reveal exceptional electrochemical stability during the redox cycle of oligomers. Structural properties including aggregation, crystallinity and morphology in thin film were investigated by UV-visible spectroscopy, atomic force microscopy (AFM), thin film X-ray diffraction (XRD) and grazing incidence small angle X-ray scattering (GISAXS) measurements. AFM reveals morphological changes induced by different processing conditions whereas GISAXS measurements show increase in the population of face-on oriented crystallites in films subjected to a combination of solvent and thermal treatments. These measurements also highlight the significance of chalcogen atom from sulphur to selenium on the photophysical, optical, electronic and solid-state properties of DPP-DPP oligomers. Charge carrier mobilities of the oligomers were investigated by fabricating top-gate bottom-contact (TG-BC) thin-film transistors by annealing the thin films under various conditions. Combined solvent and thermal annealing of DPP-DPP oligomer thin films results in consistent electron mobilities as high as ~0.2 cm 2 V -1 s -1 with an on/off ratio exceeding 10 4 . Field-effect behaviour was retained for up to ~ 4 week which illustrates remarkable air and bias stability. This work paves the way towards the development of n-type DPP-DPP based oligomers exhibiting retention of field effect behaviour with superior stability at ambient conditions.

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“…DPP is a strong electron-withdrawing moiety with exceptional stability and has been coupled with a variety of electron-rich groups to provide low band gap polymers and small molecules for BHJ solar cells [18e20], organic field effect transistors (OFETs) [21,22], dye-sensitized solar cells (DSSCs) [23,24], and chemical sensors [25]. Furthermore, introducing planar heteroarene DPP units into p-conjugated system backbones has been shown to improve relational characteristics, such as higher charge mobility and broader light absorption due to increasing the effective conjugation length by facilitating p-electron delocalization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photovoltaic performance of DPP-based small molecules with tunable energy levels by altering the molecular terminals

Liu

Xiao

et al. 2016

Dyes and Pigments

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a b s t r a c tFour novel small molecules, Ph(DPP-Th) 2 , Ph(DPP-Py) 2 , Ph(DPP-ThCN) 2 and Ph(DPP-ThR) 2 were synthesized and characterized, in which diketopyrrolopyrrole-phenyl-diketopyrrolopyrrole was used as the core, donor units of 2-octylthiophene (Th), pyrene (Py), acceptor units octyl 2-cyano-3-(thiophen-2-yl)-acrylate (ThCN) and 3-octyl-5-(thiophen-2-ylmethylene)rodanine (ThR) were used as the terminals, respectively. By changing the terminals of small molecules, their corresponding thermal, absorptive, electro-chemical and photovoltaic properties were rationally adjusted for applications as donor materials in organic solar cells (OSCs). All of small molecules exhibit broad absorption spectra from the visible to near-infrared region, and Ph(DPP-ThR) 2 showed the minimum optical band gap of 1.48 eV. The small molecules with acceptor terminal units had much deeper HOMO energy levels than those with donor terminal units, which is important to increase the open-circuit voltage (V oc ). A maximum power conversion efficiency of 3.22%, short-circuit current density of 10.55 mA cm À2 , V oc of 0.85 V, and fill factor of 39% were obtained in the Ph(DPP-Py) 2 /PC 71 BM based cells under AM 1.5 G irradiation (100 mW cm À1 ).These results demonstrate valuable guidelines for the rational design of solution-processed small molecules for OSCs.

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Diketopyrrolopyrrole-Containing Quinoidal Small Molecules for High-Performance, Air-Stable, and Solution-Processable n-Channel Organic Field-Effect Transistors

Cited by 293 publications

References 37 publications

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

Air-Stable n-channel Diketopyrrolopyrrole−Diketopyrrolopyrrole Oligomers for High Performance Ambipolar Organic Transistors

Synthesis and photovoltaic performance of DPP-based small molecules with tunable energy levels by altering the molecular terminals

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