Extended Conjugation Platinum(II) Porphyrins for use in Near-Infrared Emitting Organic Light Emitting Diodes

A family of π-extended platinum­(II) porphyrins has been synthesized and incorporated into solution processed polymer light emitting diodes (PLEDs) and vapor deposited multilayer organic light emitting diodes (OLEDs), giving rise to devices with peak emission ranging from 771 to 1005 nm. The longest wavelength emitter, platinum­(II)-5,10,15,20-(3,5-di-tert-butylphenyl)­tetraanthroporphyrin (Pt-Ar₄TAP), shows an emission maximum at 1005 nm, an external quantum efficiency (EQE) of 0.12%, and a maximum radiant emittance (R_max) of 0.23 mW/cm² in single layer PLED architectures, which is enhanced to an EQE of 0.20% with an R_max of 0.57 mW/cm² upon vapor deposition of an electron transport layer. In an effort to understand substituent effects and enhance the performance of π-extended Pt-porphyrins in PLEDs and OLEDs, a family of Pt-tetrabenzoporphyrins (Pt-TBPs) with varying functionality was investigated. The luminescent lifetimes of the Pt-TBPs in solution and in films were measured, and a strong correlation was demonstrated between the film lifetimes and the PLED and OLED efficiencies. An improvement in external quantum efficiency (EQE) from 2.07 to 2.49% for PLEDs and from 8.0 to 9.2% for OLEDs was observed between the less substituted Pt-tetraphenyltetrabenzoporphyrin and the more substituted Pt-5,10,15,20-(3,5-di-tert-butylphenyl)­tetrabenzoporphyrin. The PLED EQEs were further enhanced to 3.02% with the disubstituted Pt-5,15-(3,5-di-tert-butylphenyl)­tetrabenzoporphyrin; however, this increase was not observed for the OLEDs where an EQE of 7.8% was measured.