Conjoint use of Naphthalene Diimide and Fullerene Derivatives to Generate Organic Semiconductors for n–type Organic Thin Film Transistors

Abstract

In this paper, we described the design, synthesis, and characterization of two novel naphthalene diimide (NDI) core-based targets modified with terminal fullerene (C 60 ) yield -so called S4 and S5, in which NDI bearing 1 and 2 molecules of C 60 , respectively. The absorption, electrochemical and thin-film transistor characteristics of the newly developed targets were investigated in detail. Both S4 and S5 displayed broad absorption in the 450-500 nm region, owing to the effect of conjugation due to fullerene functionalities. The electrochem-ical measurement suggested that the HOMO and the LUMO energy levels can be altered with the number of C 60 units. Both S4 and S5 were employed as organic semiconductor materials in n-channel transistors. The thin film transistor based on S4 exhibited superior electron mobility (μe) values ranging from 1.20 × 10 À 4 to 3.58 × 10 À 4 cm 2 V À 1 s À 1 with a current on-off ratio varying from 10 2 to 10 3 in comparison with the performance of S5 based transistor, which exhibited μe ranging from 8.33 × 10 À 5 to 2.03 × 10 À 4 cm 2 V À 1 s À 1 depending on channel lengths.

Direct Arylation: A Greener Synthesis of Anthraquinone−Naphthalene diimide‐Based Small Chromophores for Applications in Organic Thin Film Transistors

“…The on current recorded at the 2.5 μm channel length was 10 −6 for all devices. These results are comparable to recently reported fullerene‐based NDI dimers and trimers [31] …”

“…Among aromatic diimides, naphthalene diimide (NDI) has proven to be an attractive option for the design and development of new n ‐type OSCs due to its planar π‐conjugated architecture [28,29] . NDI‐based OSCs now exhibit good to excellent n ‐type mobility characteristics [30,31] . Likewise, quinones display strong electron accepting properties and constitute promising candidates for n‐type air stable semiconductors [32] .…”

“…Although AQ [31–37] and NDI [38–39] exhibit good n‐type semiconducting properties. In continuation of our previous work [40] and aims to understand the influence of anthraquinone substituent on semiconducting properties of NDI and to achieve better air‐stability, the development of n ‐type OTFTs based on AQ in combination with NDI is a promising avenue.…”

Naphthalene diimide-based electron transport materials for perovskite solar cells

“…59 Some argue that organic small molecules are particularly attractive for use as ETLs as they: (1) possess welldefined chemical structures, (2) are easy to synthesize through simple and straightforward synthetic strategies, (3) hold monodisperse molecular weight, and (4) can be purified using convenient purification methods such as through simple column chromatography. [60][61][62] To improve the PCE of PSC devices, it is critical to choose the right ETL material whose energy levels complement those of both the electrodes and the light absorbing perovskite layer. A variety of organic HTL materials have been investigated in detail, and a number of reviews on their evolution and performance have been written.…”

“…For example, an ETL material based on planar coronene and fabricated in a conventional n-ip PSC architecture reported a high efficiency of >17% on a rigid and 14.2% on flexible devices. 66 The fullerenes, di(3-(pyridin-4yl)propyl) [60]fullerenyl malonate (PCP) and di(1methoxyethyl) [60]fullerenyl malonate) (MCM), possess almost identical optoelectronic properties as ETL materials, affording efficiencies beyond 19% with a planar absorber layer over 1 micrometre, yet display different passivation strength influence on the hysteresis of the device through the change in terminal Fig. 6 Structural diversity in organic ETL materials of both fullerene and non-fullerene types.…”