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We demonstrate tuning of hole injection barriers in bottom contact triisopropylsilylethynyl pentacene (TIPS-pentacene) organic thin film transistors (OTFTs) by forming the self-assembled monolayers (SAMs) of thiophenol, 4-fluorothiophenol, or pentafluorothiophenol on the pristine Ag electrode. The work functions of SAM-treated Ag electrodes are measured by Kelvin probe method. The TIPS-pentacene OTFT devices were fabricated by a drop-cast method with a micropipette like an inkjet printing. The OTFTs with pentafluorothiophenol-Ag electrodes as source and drain exhibit carrier mobility of 0.17 cm 2∕ V s and on/off current ratio of 10 5 because of almost no hole injection barrier to TIPS pentacenes. The SAM-treated Ag electrodes are robust over repeated electrical scans of 100 cycles⁠.