TY - JOUR
T1 - A-D-A Type Semiconducting Small Molecules with Bis(alkylsulfanyl)methylene Substituents and Control of Charge Polarity for Organic Field-Effect Transistors
AU - Cho, Sung Joon
AU - Kim, Min Je
AU - Wu, Ziang
AU - Son, Jae Hoon
AU - Jeong, Sang Young
AU - Lee, Sungjoo
AU - Cho, Jeong Ho
AU - Woo, Han Young
N1 - Funding Information:
This work was supported by the National Research Foundation (NRF) of Korea (grants NRF-2020M3H4A3081814, 2019R1A2C2085290, 2019R1A6A1A11044070, and 2020R1A4A2002806).
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/9/16
Y1 - 2020/9/16
N2 - In this study, we synthesize four different kinds of bis(alkylsulfanyl)methylene-substituted 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene (IDT)-based acceptor-donor-acceptor (A-D-A) type small molecules (IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC) by incorporating electron-withdrawing halogen atoms or electron-releasing thiophene spacers. Herein, enhanced structural planarity and crystalline intermolecular packing are induced by the sp2-hybridized C=C double bond side chains and sulfur-sulfur chalcogen interactions. The fine control of intramolecular charge transfer modulates the electrochemical characteristics and the resulting carrier polarity in organic field-effect transistors (OFETs). Well-balanced ambipolar, n-dominant, and p-dominant charge transport properties are successfully demonstrated in OFETs by modulating the electron-donating or withdrawing strength based on the A-D-A structural motif, resulting in hole/electron mobilities of 0.599/0.553, 0.003/0.019, 0.092/0.897, and 0.683/0.103 cm2/V·s for IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC respectively, after thermal annealing at 200 °C. Thermal annealing of the as-cast films improves the intermolecular packing in an edge-on fashion, which is investigated in detail by grazing incidence X-ray scattering. Finally, complementary logic circuits, i.e., NOT, NAND, and NOR, are fabricated by assembling p-dominant IDSTIC and n-dominant IDSIC-4Cl OFETs. Therefore, a simple and efficient molecular design strategy for fine tuning the charge polarity and charge transport properties of OFET devices is presented.
AB - In this study, we synthesize four different kinds of bis(alkylsulfanyl)methylene-substituted 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene (IDT)-based acceptor-donor-acceptor (A-D-A) type small molecules (IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC) by incorporating electron-withdrawing halogen atoms or electron-releasing thiophene spacers. Herein, enhanced structural planarity and crystalline intermolecular packing are induced by the sp2-hybridized C=C double bond side chains and sulfur-sulfur chalcogen interactions. The fine control of intramolecular charge transfer modulates the electrochemical characteristics and the resulting carrier polarity in organic field-effect transistors (OFETs). Well-balanced ambipolar, n-dominant, and p-dominant charge transport properties are successfully demonstrated in OFETs by modulating the electron-donating or withdrawing strength based on the A-D-A structural motif, resulting in hole/electron mobilities of 0.599/0.553, 0.003/0.019, 0.092/0.897, and 0.683/0.103 cm2/V·s for IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC respectively, after thermal annealing at 200 °C. Thermal annealing of the as-cast films improves the intermolecular packing in an edge-on fashion, which is investigated in detail by grazing incidence X-ray scattering. Finally, complementary logic circuits, i.e., NOT, NAND, and NOR, are fabricated by assembling p-dominant IDSTIC and n-dominant IDSIC-4Cl OFETs. Therefore, a simple and efficient molecular design strategy for fine tuning the charge polarity and charge transport properties of OFET devices is presented.
KW - A-D-A structure
KW - OFET
KW - ambipolar transistor
KW - charge polarity
KW - organic field-effect transistor
UR - http://www.scopus.com/inward/record.url?scp=85091191912&partnerID=8YFLogxK
U2 - 10.1021/acsami.0c11561
DO - 10.1021/acsami.0c11561
M3 - Article
C2 - 32819095
AN - SCOPUS:85091191912
VL - 12
SP - 41842
EP - 41851
JO - ACS applied materials & interfaces
JF - ACS applied materials & interfaces
SN - 1944-8244
IS - 37
ER -