Issue 39, 2010

Effects of the silicon core structures on the hole mobility of star-shaped oligothiophenes

Abstract

Star-shaped compounds with three or four oligothiophene units linked by an organosilicon core were prepared and their hole-transport capabilities were studied. A top-contact type thin film transistor (TFT) with a vapour-deposited film of tris[(ethylterthiophenyl)dimethylsilyl]methylsilane (3T3Si4) showed field-effect mobility (μFET) of 4.4 × 10−5 cm2 V−1 s−1, while the device with the carbon centred analogue tris[(ethylterthiophenyl)dimethylsilyl]methane (3T3Si3C) showed no TFT activity. Intrinsic intramolecular hole mobility of 3T3Si4 and 3T3Si3C was determined by time-resolved microwave conductivity measurements to be 8 × 10−2 and 2 × 10−2 cm2 V−1 s−1, respectively, arising from higher degree of σ–π interaction in 3T3Si4. To know more about the effects of the organosilicon core structures on the intermolecular hole mobility, we calculated internal reorganization energies for hole transfer at the (U)B3LYP/6-311+G(d,p)//(U)B3LYP/6-31G(d) level, which suggested smoother intermolecular charge transfer in the silicon derivative than the carbon and germanium analogues. Star-shaped compounds with quarterthiophene units behave in a different manner from the terthiophene derivatives and tris[(ethylquarterthiophenyl)dimethylsilyl]methane (4T3Si3C) showed higher TFT mobility of μFET = 1.2 × 10−3 cm2 V−1 s−1 than its silicon analogue (4T3Si4: μFET = 5.4 × 10−4 cm2 V−1 s−1). This is probably due to the more condensed packing of 4T3Si3C in the film, arising from the shorter Si–C bonding. Compounds with four terthiophene units were also prepared and tetrakis[(ethylterthiophenyl)-dimethylsilyl]silane (3T4Si5) showed the mobility of μFET = 2.0 × 10−4 cm2 V−1 s−1, higher than that of 3T3Si4, indicating the potential of tetrakis(oligothiophenyl) compounds as the TFT materials. Tetrakis[(ethylterthiophenyl)dimethylsilyl]germane (3T4Si4Ge) was less thermally stable and could not be processed to a film by vapour-deposition, but was found to be TFT active in the spin-coated film, although the mobility was rather low (μFET = 7.7 × 10−7 cm2 V−1 s−1).

Graphical abstract: Effects of the silicon core structures on the hole mobility of star-shaped oligothiophenes

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2010
Accepted
07 Jun 2010
First published
04 Aug 2010

Dalton Trans., 2010,39, 9314-9320

Effects of the silicon core structures on the hole mobility of star-shaped oligothiophenes

J. Ohshita, Y. Hatanaka, S. Matsui, T. Mizumo, Y. Kunugi, Y. Honsho, A. Saeki, S. Seki, J. Tibbelin, H. Ottosson and T. Takeuchi, Dalton Trans., 2010, 39, 9314 DOI: 10.1039/C0DT00224K

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