Asymmetric Alkylthienyl Thienoacenes Derived from Anthra[2,3-b]thieno[2,3-d]thiophene for Solution-Processable Organic Semiconductors

作者：Ogawa Yuta; Yamamoto Kazuhiro; Miura Chiyo; Tamura Shigeki; Saito Mitsuki; Mamada Masashi; Kumaki Daisuke; Tokito Shizuo; Katagiri Hiroshi^*

来源：ACS Applied Materials & Interfaces, 2017, 9(11): 9902-9909.

DOI：10.1021/acsami.6b15793

• organic semiconductor
• organic field-effect transistor
• thienoacene
• asymmetric oligomer
• solution process
• alkyl chain effect
• high mobility
• structure-property relationship

Anthra[2,3-b]thieno[2,3-d]thiophene (ATT), which is readily accessed from thieno[3,2-b]thiophene and 2,3naphthalenedicarboxylic anhydride, allows for selective substitution at the terminal thiophene ring, thereby providing asymmetric monoalkyl and monoalkylthienyl thienoacenes. Alkyl-substituted ATT (CnATT, n = 6, 8, 10, 12) has characteristics of a p-type field-effect transistor (FET), with mobility on the order of 0.01 cm(2) V-1 s(-1), which is the same as ATT. Conversely, alkylthienylsubstituted ATT (CnTATT, n = 6, 8, 10, 12) exhibits FET mobility of 0.15-1.9 cm(2) V-1 s(-1), which is up to 2 orders of magnitude greater than that of ATT and CnATT. Moreover, CnTATT forms crystalline thin films both by spin coating and drop casting, and C8TATT in particular exhibits a mobility of up to 1.6 cm(2) s(-1) in the drop-cast film. X-ray diffraction patterns of CnTATT thin films indicate that the molecules become oriented edge-on at the substrate surface with a highly ordered structure in the in-plane direction. Accordingly, CnTATT serves as a solution-processable p-type organic field-effect transistor, where the additional thiophene ring contributes significantly to the highly ordered thin-film structure and the high carrier mobility.

• 出版日期2017-3-22