BODIPY platform: a tunable tool for green to NIR OLEDs

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The rapid appearance of organic optoelectronics as a promising alternative to conventional optoelectronics has been largely achieved through the design and development of new conjugated systems. The 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY)-based materials have recently emerged as platforms for many types of applications such as sensors, organic thin-film transistors and organic photovoltaics; however, their application as active materials in organic light-emitting diodes (OLEDs) has only been poorly explored. This review article provides an overview of the most important developments in the structural design and synthesis of BODIPY-based organic semiconductors for application in OLED devices. The results summarised and discussed here include the most relevant results starting from the first application of BODIPY-based materials in OLEDs in 2002 up to the recent discoveries as near-IR emitters also promoted by aggregation-induced emission (AIE). Therefore, this review should inspire new research for future developments of BODIPY-based materials, in particular as ‘metal-free’ infrared emitters.Abbreviations: ACQ: aggregation caused quenching; AIE: aggregation induced emission; Alq3: aluminium tris(8-hydroxyquinoline); BCP: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline); BDP-PPV: poly(bis(3″,7″-dimethyloctyloxy))p-phenylene vinylene; BF3OEt2: boron trifluoride diethyletherate; BPhen: bathophenanthroline; CBP: 4,40-bis[N-carbazolyl]-2,20-biphenyl; CIE: Commission Internationale de l’Eclairage; DDQ: dichloro-dicyano-quinone; EL: electroluminescence; F8BT: poly(9,9-dioctylfluorene-alt-benzothiadiazole); ITO: indium tin oxide; LEC: light-emitting electrochemical cell; m-MTDATA: 4,4ʹ,4ʹ’-tris[phenyl(m-tolyl)amino]triphenylamine; NPB: N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidine; NPD: N,N’-di(1-naphtyl)-N,N’-diphenylbenzidine; OLED: organic light-emitting diode; OPV: organic photovoltaic; OXD-7: 2,2′-(1,3-phenylene)-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole; PBD: 2-(4-biphenylyl)-5(4tert-butyl-phenyl)-1,3,4-oxadiazole; PEDOT: poly(3,4-ethylenedioxythiophene); PLED: polymeric light-emitting diodes; PMMA: polymethylmetacrilate; PPT: 2,8-bis(diphenylphosphoryl)dibenzo[b,d]thiophene; PSS: polystyrene sulphonic sodium salt; PVK: poly(9-N-vinylcarbazole); TPBi: 2,2ʹ,2”-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole); TPE: tetraphenylethylene; WOLED: white organic light-emitting diode; 3-TPyMB: tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane