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Solution‐Processable n‐Type Semiconductors Based on Unsymmetrical Naphthalene Imides: Synthesis, Characterization, and Applications in Field‐Effect Transistors
Author(s) -
Shao Jinjun,
Chang Jingjing,
Chi Chunyan
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300895
Subject(s) - materials science , thermal stability , naphthalene , electron mobility , homo/lumo , organic semiconductor , imide , thin film transistor , solubility , field effect transistor , electrochemistry , semiconductor , crystal structure , transistor , analytical chemistry (journal) , optoelectronics , chemistry , organic chemistry , polymer chemistry , nanotechnology , molecule , electrode , layer (electronics) , physics , voltage , quantum mechanics
A series of unsymmetrical naphthalene imide derivatives ( 1a , 1b , 2 , 3 , 4 , 5 ) with high electron affinity was synthesized and used in n‐channel organic field‐effect transistors (OFETs). They have very good solubility in common organic solvents and good thermal stability up to 320 °C. Their photophysical, electrochemical, and thermal properties were investigated in detail. They showed low‐lying LUMO energy levels from −3.90 to −4.15 eV owing to a strong electron‐withdrawing character. Solution‐processed thin‐film OFETs based on 1a , 1b , 2 , 3 , 4 were measured in both N 2 and air. They all showed n‐type FET behavior. The liquid‐crystalline compounds 1a , 1b , and 3 showed good performance owing to the self‐healing properties of the film in the liquid‐crystal phase. Compound 3 has an electron mobility of up to 0.016 cm 2 V −1 s −1 and current on/off ratios of 10 4 –10 5 .