Abstract
AbstractReported here is a new high electron affinity acceptor end group for organic semiconductors, 2,1,3‐benzothiadiazole‐4,5,6‐tricarbonitrile (TCNBT). An n‐type organic semiconductor with an indacenodithiophene (IDT) core and TCNBT end groups was synthesized by a sixfold nucleophilic substitution with cyanide on a fluorinated precursor, itself prepared by a direct arylation approach. This one‐step chemical modification significantly impacted the molecular properties: the fluorinated precursor, TFBT IDT, a poor ambipolar semiconductor, was converted into TCNBT IDT, a good n‐type semiconductor. The electron‐deficient end group TCNBT dramatically decreased the energy of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO) compared to the fluorinated analogue and improved the molecular orientation when utilized in n‐type organic field‐effect transistors (OFETs). Solution‐processed OFETs based on TCNBT IDT exhibited a charge‐carrier mobility of up to μe≈0.15 cm2 V−1 s−1 with excellent ambient stability for 100 hours, highlighting the benefits of the cyanated end group and the synthetic approach.
Highlights
The development of organic semiconductors (OSCs) for use in organic electronic devices, including field-effect transistors (OFETs), continues to attract interest because of their ease in film and device fabrication from solution
An n-type organic semiconductor with an indacenodithiophene (IDT) core and TCNBT end groups was synthesized by a sixfold nucleophilic substitution with cyanide on a fluorinated precursor, itself prepared by a direct arylation approach
The electron-deficient end group TCNBT dramatically decreased the energy of the highest occupied and lowest unoccupied molecular orbitals (HOMO/ LUMO) compared to the fluorinated analogue and improved the molecular orientation when utilized in n-type organic fieldeffect transistors (OFETs)
Summary
The development of organic semiconductors (OSCs) for use in organic electronic devices, including field-effect transistors (OFETs), continues to attract interest because of their ease in film and device fabrication from solution Such devices can be utilized for various applications, ranging from lightweight and flexible logic circuits to skin sensors.[1] These applications typically require a good balance of charge-carrier mobility between p-type (hole-transporting) and n-type (electron-transporting) OFETs to ensure high noise immunity and low static power consumption in the ensuing electronic circuits and systems.[2] While tremendous progress has been made in the development of high-performance p-type OSCs for such applications,[3] the performance of n-type OSCs lags significantly behind, both in terms of charge-carrier mobility and device stability.[4]. By comparing the optoelectronic properties and structural characteristics of the TCNBT IDT semiconductor with those of its fluorinated counterpart TFBT IDT, we demonstrate that TCNBT end groups deepen both the HOMO and LUMO of the semiconductor and induce a highly ordered molecular structure, leading to good ambient stability and electron transport characteristics, respectively
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