Bifunctional Heterocyclic Spiro Derivatives for Organic Optoelectronic Devices

Abstract

A series of heterocyclic spiro derivatives has been successfully synthesized and characterized by photophysical and electrochemical studies. Taking advantage of their excellent hole-transporting properties, highly efficient small-molecular organic photovoltaic devices based on these heterocyclic compounds as donors with very low dopant concentrations have been prepared; particularly, a high open-circuit voltage of up to 1.10 V and a power conversion efficiency of up to 5.12% have been realized. In addition, most of these heterocyclic spiro derivatives are found to be highly emissive in solutions with photoluminescence quantum yields of up to 0.91, and high-performance deep-blue-emitting organic light-emitting diodes (OLEDs) have been achieved. Such devices exhibit a stable deep blue emission with CIE coordinates of (0.16, 0.04) and high external quantum efficiencies of up to 4.7%, which is one of the best values among the reported OLEDs with CIEy < 0.08.

Ultrasound-assisted transition-metal-free catalysis: a sustainable route towards the synthesis of bioactive heterocycles

“…Notwithstanding the tremendous pharmaceutical application, a diversified structural scaffold comprising a heterocyclic core has been demonstrated to be a crucial element in multiple materials science sectors. For instance, organic light-emitting diodes (OLEDs), 14 organic optoelectronic devices, 15 organic solar cells, 16 organic semiconductors, 17 potential fluorescent materials, 18 electroluminescent components, 19 and dye-sensitized solar cells are some of the promising applications of heterocyclic compounds in materials science, among others. 20 …”

Optical and Photosensitizing Properties of Spiro(dipyridinogermole)(dithienogermole)s with Eletron‐Donating Amino and Electron‐Withdrawing Pyridinothiadiazole Substituents

“…The applications of spiro‐condensed D−A compounds as host materials for phosphorescent OLEDs have been reported . Other high‐performance emissive materials for OLEDs have been also prepared on the basis of spiro‐condensed structures.…”

Design, Synthesis and Electronic Properties of Novel Spirobifluorene Derivatives

“…9,9′-Spirobifluorene derivatives are widely used as an efficient hole-transporting materials (HTM) in organic lightemitting devices (OLEDs) [1][2][3][4][5][6][7], organic field-effect transistors (OFETs), [7][8][9][10] solid state dye-sensitized solar cells (ssDSSCs) [11][12][13][14][15][16][17][18][19][20] and recently in perovskite-sensitized solar cell [21][22][23][24]. The shared sp3 hybridized carbon atom of two connected fluorene moieties in spirobifluorene derivatives leads to an unusual cross-shaped rigid structure.…”

“…Towards the synthesis of the desired spirobifluorene derivatives, first, different diaryl amines (5)(6)(7)(8) were synthesized with excellent yield of 80-90%, via the palladium catalyzed Buchwald-Hartwig C-N cross coupling [30] of various aryl bromides and primary aryl amines. The synthesized diaryl amines were purified by column chromatography and characterized by 1 H and 13 C NMR spectroscopy and mass spectrometry.…”

“…The synthesized diaryl amines were purified by column chromatography and characterized by 1 H and 13 C NMR spectroscopy and mass spectrometry. Next, the target spirobifluorene derivatives were synthesized starting from 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene (9) via palladium catalyzed C-N cross coupling [31] with various diaryl amine (5)(6)(7)(8). The synthesized spirobifluorene derivatives (1-4) were purified by column chromatography with an average yield of around 60%.…”