Naphthalenetetracarboxylic Diimide-Based n-Channel Transistor Semiconductors:  Structural Variation and Thiol-Enhanced Gold Contacts

Abstract

The synthesis and field-effect transistor (FET) electron mobility of ten N-substituted naphthalene 1,4,5,8-tetracarboxylic diimide (NTCDI) derivatives deposited at ambient and elevated temperatures are reported. Mobilities >0.01 cm2/(V s) were measured in air for three NTCDIs with partially fluorinated substituents, and >0.001 cm2/(V s) for a hydroxy-terminated compound. Mobilities 0.001−0.1 cm2/(V s) were also found for three n-alkyl NTCDIs, but only under vacuum; FET operation with gold bottom contacts was enabled by specific thiol coatings of the contacts. The highest mobility in air, >0.1 cm2/(V s), was conferred by 4-trifluoromethylbenzyl substitution, while 1H,1H-perfluorooctyl substitution resulted in an on/off ratio in air >105. Solution electrochemistry and solid-state X-ray and electron diffraction were employed to partially explain the results, and applications of the materials to complementary circuits are considered.

Development of Conductive Organic Molecular Assemblies: Organic Metals, Superconductors, and Exotic Functional Materials

“…53 Interestingly, treatment of the device with tetrakis(dimethylamino)ethylene (TDAE) results in an increase of the mobility by a factor of 3. 50 Rather high mobilities have also been reported for some FETs fabricated from aromatic hydrocarbon derivatives such as N,N 0 -dialkyl-1,4,5,8-naphthalenetetracarboxylic diimide (NTCDI, > 0:1 cm 2 V À1 s À1 ), 54 and N,N 0 -dioctyl-3,4,9,10-perylenetetracarboxylic diimide (PTCDI, 0.6 cm 2 V À1 s À1 ). 55 However, these devices are highly oxygen-sensitive, and thus may not be suitable for practical applications.…”

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

“…[126][127][128][129][130] Among the diimide derivatives, perylenetetracarboxylic diimide (PDI) and naphthalenetetracarboxylic diimide (NDI) seem to be the most suitable for electron transporting OSCs. 129,[131][132][133][134][135] Meanwhile, additional strategies were adopted following basic Fig. 2 Single path mobilities predicted using Marcus theory.…”

C60thin-film transistors with high field-effect mobility, fabricated by molecular beam deposition

“…However, mobilities of n-type TFTs remains poor compared with p-type ones. In ntype TFTs, mobilities of fluorinated phthalocyanine [3], naphthalene and perylene derivatives such as N-substituted naphthalene 1,4,5,8-tetracarboxylic diimide (NTCDI) [4] or N,N 0 -dialkil-3,4,9,10-perylene tetracarboxylic diimide (PTCDI) has been recently found to be a promising group of materials. In 2002, mobilities up to 0.6 cm 2 /V s and current on/off ratio .…”