Acyclic, Linear Oligo-meta-phenylenes as Multipotent Base Materials for Highly Efficient Single-layer Organic Light-emitting Devices.

Oligo-meta-phenylenes have been designed and synthesized as multipotent base materials of single-layer organic light-emitting devices. Simple molecular structures of oligo-meta-phenylenes composed of linear phenylene arrays benefited from the wealth of modern reactions available for biaryl couplings and were concisely synthesized in a series. Structure-performance relationship studies with the first seven congeners revealed key features important for the multipotent materials in single-layer devices. As a result, highly efficient phosphorescent electroluminescence was made possible in a highly simplified device architecture comprising one-region, single-layer configurations. Detailed investigations with hole-only devices disclosed that the hole mobility was effectively retarded by potent materials, which should facilitate hole/electron recombination for electroluminescence.

Periphery Design of Macrocyclic Materials for Organic Light-Emitting Devices with a Blue Phosphorescent Emitter.

Cyclo- meta-phenylenes were modified with trifluoromethyl groups at their periphery to create host materials suitable for use in blue phosphorescent organic light-emitting devices. The periphery design resulted in molecules with high triplet-state energies, which were required to support the blue emission from Ir phosphors. As a result, an external quantum efficiency of 9.9% was achieved. The most successful host, a pentameric congener, preferred CF-π/CH-π interactions in its crystalline packings, which could be beneficial for the host performance.

Efficient Blue Electroluminescence from a Single-layer Organic Device Composed Solely of Hydrocarbons.

An interesting physical phenomenon, electroluminescence, that was originally observed with a hydrocarbon molecule has recently been developed into highly efficient organic light-emitting devices. These modern devices have evolved through the development of multi-element molecular materials for specific roles, and hydrocarbon devices have been left unexplored. In this study, we report an efficient organic light-emitting device composed solely of hydrocarbon materials. The electroluminescence was achieved in the blue region by efficient fluorescence and charge recombination within a simple single-layer architecture of macrocyclic aromatic hydrocarbons. This study may stimulate further studies on hydrocarbons to uncover their full potential as electronic materials.

Aromatic hydrocarbon macrocycles for highly efficient organic light-emitting devices with single-layer architectures.

A modern electrophosphorescent organic light-emitting device (OLED) achieves quantitative electro-optical conversion by using multiple layers of molecular materials designed through role allotment for independent and specific functions. A unique, potentially innovative device architecture, i.e., a single-layer phosphorescent OLED, is currently being developed by designing multirole base materials via a structural combination of multiple functional components in single molecules. The multirole molecules, however, inevitably require multiple processes to synthesize their multiple components and, moreover, to assemble these components synthetically into one molecule. We herein show that the multirole base material for a highly efficient single-layer phosphorescent OLED can be designed and synthesized with a single, very simple aromatic hydrocarbon component of toluene merely through a one-pot macrocyclization. Without requiring the assembly tasks at the synthesis stage, the molecular design allows for a concise one-pot synthesis of, and a quantitative electro-optical conversion in, the single-layer device architecture with a single-component base material.

Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices.

A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices with a phosphorescent emitter, which is, notably, in a single-layer architecture consisting of two regions of doped and undoped materials. The highest external quantum efficiencies reached 24.8%, surpassing those of previous hydrocarbon base materials.

Cyclo-meta-phenylene revisited: nickel-mediated synthesis, molecular structures, and device applications.

From a one-pot nickel-mediated Yamamoto-type coupling reaction of m-dibromobenzene, five congeners of [n]cyclo-meta-phenylenes were synthesized and fully characterized. The [n]cyclo-meta-phenylenes possessed a commonly shared arylene unit and intermolecular contacts but varied in packing structures in the crystalline solid state. Columnar assembly of larger congeners yielded nanoporous crystals with carbonaceous walls to capture minor protic or aliphatic solvent molecules. The concise and scalable synthesis allowed exploration of the macrocyclic hydrocarbons as bipolar charge carrier transport materials in organic light-emitting diode devices.