Comparison of charge transport and opto-electronic properties of pyrene and anthracene derivatives for OLED applications

K Uzun,U Çevik,S Sayın,Ö Tamer

doi:10.1007/s00894-021-04793-2

Abstract

In this paper, three organic semiconductors such as 9-[(5-nitropyridin-2-aminoethyl)iminiomethyl]-anthracene (a), N'-((pyren-4-yl)methylene)isonicotinohydrazide (b), and novel organic semiconductor N-(2-((pyren-4-yl)methyleneamino)ethyl)-5-nitropyridin-2-amine (c) were prepared. Their structures were assessed using NMR and elemental analysis techniques. While compound (a) and compound (c) have the same wing unit ([(5-nitropyridin-2-aminoethyl) iminiomethyl]), compounds (b) and (c) have the same core unit (5-nitropyridin-2-amine). Based on TD-DFT and Marcus theories, we have explored the effects of molecular structure on the opto-electronic properties for OLED applications. Our results show that wing units of molecules impact more on the opto-electronics properties than on core units. The compounds (a) and (c) with the same wing unit have exhibited quite similar behaviors in terms of both structural and opto-electronic parameters. However, a similar situation has not been observed for compounds (b) and (c) with the same core unit. In conclusion, our results indicate that compounds (a) and (c) exhibit obvious advantages for OLEDs in terms of calculated opto-electronic and charge transport properties such as better absorption and emission parameters, lower energy gaps and reorganisation energies and higher charge mobility.

Highlights

In 2000, Shirakawathe, MacDiarmid and Heeger [1] has awarded by Nobel Chemistry Prize for their discovery of some organic molecules showing semiconductor properties and this has attracted the interest of scientists in organic semiconductors and revealed an area called “organic electronics” [2]
Compound a (9-[(5nitropyridin-2-aminoethyl) iminiomethyl]- anthracene) which has anthracene as central core and compound b (N-[2-((Pyren-4-yl)methyleneamino)ethyl-5-nitropyridin-2-amine) and compound c (N’-[((Pyren-4-yl)methylene) isonicotinohydrazide)) which have pyrene as central core which are shown in Scheme 1
Theoretical calculations, allowed us to assess the role of the wing unit and core unit of the organic molecules on the optoelectronic properties of these materials

Summary

Introduction

In 2000, Shirakawathe, MacDiarmid and Heeger [1] has awarded by Nobel Chemistry Prize for their discovery of some organic molecules showing semiconductor properties and this has attracted the interest of scientists in organic semiconductors and revealed an area called “organic electronics” [2]. A theoretical investigations about the effect of molecular structure on the vibrational, opto-electronic and charge transport properties of molecules based on anthracene and pyrene. Computational Methods All quantum chemical calculations interested in geometric parametres, opto-electronic and charge transport properties, vibrational wave numbers of the compounds have been carried out using the Gaussian 09w programme [12].

Results

Conclusion