Chiral iridium(iii) complexes with four-membered Ir–S–P–S chelating rings for high-performance circularly polarized OLEDs

Abstract

CP-OLEDs with two series of chiral iridium(iii) complexes based on four-membered Ir–S–P–S chelating rings and chiral BINOL-based derivatives show excellent electroluminescence performances with obvious CPEL properties.

Beyond Chiral Organic (p-Block) Chromophores for Circularly Polarized Luminescence: The Success of d-Block and f-Block Chiral Complexes

“…(A) Homoleptic fac -[Ir(pppy) 3 ] complex (Schaffner-Hamann et al, 2004 ). Heteroleptic complexes [Ir(C ∧ N) 2 (X ∧ Y)] n+ holding (B) achiral C ∧ N and chiral X ∧ Y ligands (Li et al, 2016 ; Mazzeo et al, 2016 ; Li L.-P. et al, 2017 ; Manguin et al, 2019 ; Yan et al, 2019a ), (C) chiral C ∧ N and achiral X ∧ Y ligands (Yang et al, 2009 ), (D) chiral C ∧ N and X ∧ Y ligands (Yan et al, 2018 ), and (E) helicenic–NHC chiral ligand X ∧ Y (Hellou et al, 2017 ; Macé et al, 2019 ).…”

“…Apart from 13 , the chemical attention usually focused on heteroleptic [Ir(C ∧ N) 2 (X ∧ Y)] n+ complexes probably because they are obtained by the simple reaction of the aforementioned Ir III intermediates ([Ir(C ∧ N) 2 Cl 2 ] − or [(Ir(C ∧ N) 2 Cl) 2 ]) with enantiopure ligands, a versatile strategy which produces a library of complexes with various chiral ligands. In particular, the combination of achiral C ∧ N ligands with a chiral X ∧ Y one afforded the most important library of [Ir(C ∧ N) 2 (X ∧ Y)] n+ complexes for CPL, mainly based on central chirality ( 14 – 17 ) (Li et al, 2016 ; Mazzeo et al, 2016 ; Li L.-P. et al, 2017 ; Manguin et al, 2019 ), albeit axial chirality was occasionally exploited with ligands containing 1,1′-bi-2-naphthol derivatives ( 18 – 19 ) ( Figure 8B ) (Han et al, 2017b ; Yan et al, 2019a ). Although a few examples report on full chiral induction ( 14 ) (Li L.-P. et al, 2017 ), in most cases the separation of the formed diastereoisomer pair was achieved by selective diasteroisomer precipitation ( 15 ) (Mazzeo et al, 2016 ), by HPLC ( 16 ) (Li et al, 2016 ), or by silica column chromatography ( 17 – 19 ) (Manguin et al, 2019 ; Yan et al, 2019a ).…”

Rational Design of the Platinahelicene Enantiomers for Deep-Red Circularly Polarized Organic Light-Emitting Diodes

“…fluorescence materials (Feuillastre et al, 2016;Han et al, 2017;Wu et al, 2019) exhibit increasingly satisfactory results in term of the electroluminescence properties. Nevertheless, most of these materials used in efficient OLEDs exhibit poor CPL properties with the |g PL | value in the range of 10 −5 to 10 −3 (Han et al, 2018;Yan et al, 2019b) and mostly <5 × 10 −3 . Hence, it is important to provide a design strategy to improve their CPL properties.…”

Enhanced Circularly Polarized Luminescence Activity in Chiral Platinum(II) Complexes With Bis- or Triphenylphosphine Ligands

“…Especially these phosphorescent transition metal complexes, which have remarkable metal-center chirality, tunable emission properties, and unusually high phosphorescence efficiency, are receiving increasing interests in recent years (Han et al, 2018). Such CPL-active materials as Pt (Shen et al, 2014), Ir (Han et al, 2017;Hellou et al, 2017;Yan et al, 2019a), Au (Yang et al, 2020;Zhu et al, 2020), Cu (Jin et al, 2019;Deng et al, 2020;Yao et al, 2020), Zn (Aoki et al, 2017;Chen Y. et al, 2019) Cd (Deng et al, 2019), and Cr (Jiménez et al, 2019) complexes can exhibit various emission colors from blue to red. The dissymmetry factor g lum (g lum = 2 I/I = 2(I L -I R )/(I L + I R ), where I L and I R indicate, respectively, the intensity of the left and right circularly polarized light), can reach up to 10 −2 order.…”