Easily Synthesized Naphthalene Tetracarboxylic Diimide Semiconductors with High Electron Mobility in Air

Abstract

New N,N′-substituted 1,4,5,8-naphthalene tetracarboxylic diimides (NTCDIs) were synthesized in one step reactions, resulting in excellent electron mobilities in air as measured in organic field effect transistors (OFETs). Two perfluoroalkyl-benzyl N,N′ substituents were used, differing in the length of the perfluoroalkyl moieties on the benzyl portion of the molecule. Single crystals of the short chain compound 2 were successfully grown by horizontal vapor deposition, and crystal structures were obtained and analyzed. Devices from both compounds were fabricated on untreated and silane treated Si/SiO2 substrates. The longer chain compound 1 gives the largest field effect mobility, reaching 0.57 cm2/(V s) in air. This is competitive with the best air stable n-channel materials to date. In contrast to previously studied high mobility materials, 1 achieved mobilities near 0.4 cm2/(V s) without the use of dielectric substrate treatments. Additionally, 1 displays exemplary ordering regardless of surface treatment, as determined from X-ray diffraction, while 2 displays significant improvement in mobility and film structure when deposited on surface treated substrates.

Air‐Operable, High‐Mobility Organic Transistors with Semifluorinated Side Chains and Unsubstituted Naphthalenetetracarboxylic Diimide Cores: High Mobility and Environmental and Bias Stress Stability from the Perfluorooctylpropyl Side Chain

“…This discrepancy is thus due to the experimental uncertainty of the laboratory X-ray source at low angles. [ 45 ] 8-3-NTCDI has a 3 carbons longer side chain than the reported F15-NTCDI with C 7 F 15 CH 2 -side chain, but the d-spacing of 8-3-NTCDI is only 1 Å longer than that of F15-NTCDI, [ 42 ] and is similar to that of 8-1-NTCDI and smaller than that of 8-2-NTCDI. The layer spacing of 8-3-NTCDI is lower than predicted from the trend from 8-1-NTCDI to 8-4-NTCDI with increasing carbon number, as shown in Table 4 .…”

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

“…142 The efficient charge transport properties of 1j were attributed to its superior molecular ordering in the thin film. Similarly, perfluorophenyl substituted NDI derivative 1k exhibits significantly higher mobilities of 0.87 and 0.31 cm 2 V À1 s À1 under vacuum and in air, respectively, along with a high current on/off ratio of 10 7 , corroborating that n-type mobility is influenced simultaneously by thermodynamic and kinetic factors.…”

Semiconducting Organic Molecular Materials

“…5 (13, PDIs). Among NDIs, the highest mobility in inert atmosphere was found to be 6.2 cm 2 V −1 s −1 for 12a [21], while the highest mobility under ambient condition was found to be 0.57 cm 2 V −1 s −1 for 12b [22]. OFETs based on Fig.…”