Cyclohexyl-Substituted Anthracene Derivatives for High Thermal Stability Organic Semiconductors.

Yicai Dong,Tao Li,Yuanping Yi,Jing Zhang,Lang Jiang,Yanjun Shi,Wenping Hu,Hantang Zhang,Haiyang Li,Xiuqiang Lu,Jie Liu,Yuan Guo

doi:10.3389/fchem.2019.00011

Abstract

A novel p-type organic semiconductor with high thermal stability is developed by simply incorporating cyclohexyl substituted aryl groups into the 2,6-position of anthracene, namely 2,6-di(4-cyclohexylphenyl)anthracene (DcHPA), and a similar compound with linear alkyl chain, 2,6-di(4-n-hexylphenyl)anthracene (DnHPA), is also studied for comparison. DcHPA shows sublimation temperature around 360°C, and thin film field-effect transistors of DcHPA could maintain half of the original mobility value when heated up to 150°C. Corresponding DnHPA has sublimation temperature of 310°C and the performance of its thin film devices decreases by about 50% when heated to 80°C. The impressing thermal stability of the cyclohexyl substitution compounds might provide guidelines for developing organic electronic materials with high thermal stability.

Highlights

Organic field-effect transistors (OFETs) with organic semiconductors as key elements have been extensively studied and believed to play a prominent role in future organic electronics, such as flexible displays (Tang et al, 2009), the radio frequency identity tags (RFID) (Subramanian et al, 2005), and various sensors (Huang et al, 2008, 2017; Knopfmacher et al, 2014; Lu et al, 2017b)
The highest occupied molecular orbital (HOMO) energy level of DcHPA was calculated from the onset of the oxidation peak with reference to Fc+/Fc (4.8 eV) using the equation of EHOMO = [4.8-EFc+Eonsetox] eV, and HOMO level of 5.6 eV was determined, which was similar to that of 2,6-diphenylanthracene (DPA) (Liu et al, 2015a,b)
The molecular geometric structures of DnHPA and DcHPA were optimized by density functional theory (DFT) at the B3LYP/6-31G∗∗ level

Summary

Introduction

Organic field-effect transistors (OFETs) with organic semiconductors as key elements have been extensively studied and believed to play a prominent role in future organic electronics, such as flexible displays (Tang et al, 2009), the radio frequency identity tags (RFID) (Subramanian et al, 2005), and various sensors (Huang et al, 2008, 2017; Knopfmacher et al, 2014; Lu et al, 2017b). The d-spacing of DcHPA obtained from the first diffraction peak was 1.67 nm based on the equation of 2d × sin θ = nλ, which was consistent with the single layer thickness shown in Figure 2C inset.

Results

Conclusion