Perylene-Based Liquid Crystals as Materials for Organic Electronics Applications

Abstract

Columnar phases formed by the stacking of disclike molecules with an intimate π-π overlap forms a 1D pathway for the anisotropic charge migration along the columns. Columnar phases have great potential in organic electronic devices to be utilized as active semiconducting layers in comparison to organic single crystals or amorphous polymers in terms of processability, ease of handling, and high charge carrier mobility. Intelligent molecular engineering of perylene and its derivatives provided access to tune the physical properties and self-assembly behavior. The columnar phase formed by perylene derivatives has great potential in the fabrication of organic electronic devices. There are several positions on the perylene molecule, which can be functionalized to tune its self-assembly, as well as optoelectronic properties. Thus, many liquid-crystalline molecules stabilizing the columnar phase, which are based on perylene tetraesters, perylene diester imides, and perylene bisimides, have been synthesized over the years. Their longitudinal and laterally extended derivatives, bay-substituted derivatives exhibiting a columnar phase, are reported. In addition, several liquid-crystalline oligomers and polymers based on perylene derivatives were also reported. All such modifications provide an option to tune the energy levels of frontier molecular orbitals with respect to the work function of the electrodes in devices and also the processability of such materials. In this feature article, we attempt to provide an overview of the molecular design developed to tune the applicable properties and self-assembly of perylene derivatives as well as recent developments related to their application in the fabrication of organic solar cells, organic light-emitting diodes, and organic field-effect transistors.

Novel Solid-State Emissive Polymers and Polymeric Blends from a T-Shaped Benzodifuran Scaffold: A Comparative Study

“…For application, the amorphous status could be an advantage. As their PL performance is independent of the crystalline order, attention should not be paid to the deposition methods [35,36].…”

Facile Synthetic Route for Direct Access of Perylenediimide Single Crystals in High Yield through In Situ Crystallization

“…Self‐assembly of π‐conjugated organic molecules into one‐dimensional (1D) materials are of special interest due to their potential applications in optical, electronic and optoelectronic devices . Molecular organization of π‐conjugated organic molecules strongly influence on the material properties and performance of the devices, such as field effect transistor, organic photovoltaics, organic light emitting diodes (OLED) and electrical conductivity . For instance, self‐assembly of polyaromatic molecules via aromatic stacking into infinite columnar structures resulted in the formation of 1D columnar liquid crystals .…”

Synthesis and helical supramolecular organization of discotic liquid crystalline dibenzo[hi,st]ovalene

“…A wide range of applications has thus been proposed for PAHs, not only as semiconductor materials in organic field-effect transistors and light-emitting devices, but also as fluorescent dyes in bioimaging. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] The supramolecular organization of the disc-shaped PAH molecules is of particular interest, leading to various self-assembled structures such as columns, nanotubes, and micelles. [15][16][17][18][19][20][21][22][23] The combination of the rigid PAH cores with flexible aliphatic chains at the peripheral positions can induce a phase separation between these two components at the molecular level, resulting in the formation of columnar structures due to the strong intermolecular p-p interactions, and discotic liquid crystalline (LC) properties.…”