Fluorescent isoindoline dyes
The present invention provides a new class of excited state intramolecular charge transfer (ESIPT) dye compounds based on mono or dihydroxy substituted 1,3-bisiminoisoindole motif and metal complexes containing such compounds as ligands. The present invention also provides OLEDs containing the compound and/or metal complex as the emissive material.
1. A compound of the following formula:
wherein Y 1 is NR 1 ; or a compound of the following formula:
wherein Y 3 is NR 3 ,
wherein X 1 , X 2 , and X 3 are independently N or CR 4 , N or CR 5 , and N or CR 6 , respectively, wherein R 4 and R 5 and/or R 5 and R 6 can optionally form a ring or R 4 and R 6 can optionally form a ring,
wherein R 1 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of H, a halogen, a hydroxy group, an amino group, a carboxyl group, an aliphatic group, a heteroaliphatic group, a cyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, and a combination thereof.
2. A compound selected from the group consisting of the following compounds:
wherein X 1 , X 2 , and X 3 are independently N or CR 4 , N or CR 5 , and N or CR 6 , respectively, wherein R 4 and R 5 and/or R 5 and R 6 can optionally form a ring or R 4 and R 6 can optionally form a ring,
wherein R 4 , R 5 , and R 6 are independently selected from the group consisting of H, a halogen, a hydroxy group, an amino group, a carboxyl group, an aliphatic group, a heteroaliphatic group, a cyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, and a combination thereof,
wherein n can be any number of repeating units.
3. A complex comprising a metal atom M and a ligand as shown by the following formula:
wherein - - - - - represents an optional coordination bond, at least one of which being present, wherein Y 1 and Y 3 are NR 1 and NR 3 , respectively, at least one containing an atom for forming a coordination bond, wherein R 1 and R 3 can optionally form a ring,
wherein R 1 and R 3 are the same functional group selected from the group consisting of 2-pyridyl and 1-isoquinolyl,
wherein X 1 is CR 4 , X 2 is CR 5 , R 4 and R 5 being OH or Cl, and
wherein X 3 is CR 6 , R 6 being OH or OEt.