Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
OwnerVladimir Grushin, Viacheslav A. Petrov +1inventors
InventorsVladimir Grushin, Viacheslav A. Petrov, Ying Wang
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Abstract
The present invention is generally directed to electroluminescent Ir(III) compounds, the substituted 2-phenylpyridines, phenylpyrimidines, and phenylquinolines that are used to make the Ir(III) compounds, and devices that are made with the Ir(III) compounds.
Claims22
An organic electronic device comprising an emitting layer wherein at least 20% by weight of the emitting layer comprises at least one compound having a formula below:
- IrLaLbLcxL′yL″z,
- where:
- x=0 or 1, y=0, 1 or 2, and z=0 or 1, with the proviso that:
- x=0 or y+z=0 and
- when y=2then z=0;
- L′=a bidentate ligand or a monodentate ligand, and is not a phenylpyridine, phenylpyrimidine, or phenylquinoline;
- with the proviso that:
- when L′ is a monodentate ligand, y+z=2, and when L′ is a bidentate ligand, z=0;
- L″=a monodentate ligand, and is not a phenylpyridine, and phenylpyrimidine, or phenylquinoline;
- and
- La, Lb and Lc are alike or different from each other and each of La, Lb and Lc has structure (I) below:
- 10
- wherein:
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring,
- at least one of R1-R8 is selected from F, CnF2n+1, OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and
- A=C or N, provided that when A=N, there is no R1.
An organic electronic device comprising an emitting layer wherein the emitting layer comprises a diluent and less than 20% by weight of at least one compound that has a formula below:
- IrLaLbLc,
- where:
- La, Lb and Lc are alike or different from each other and each of La, Lb and Lc has structure (I) below:
- 12
- wherein:
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring,
- at least one of R1-R8 is selected from F, CnF2n+1, OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and A=C or N, provided that when A=N, there is no R1.
A compound having a formula selected from fac-Ir(L)3, mer-Ir(L)3, and combinations thereof, where L is selected from group 1-a through 1-m and 1-q through 1-v, as shown in Table 1, and has structure (I) below:
- 13
- wherein:
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring, |at least one of R1-R8 is selected from F, CnF2n+1 , OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and
- A=C or N, provided that when A=N, there is no R1.
A compound having a structure selected from structures (IV), (V), (VI), (IX) and (X) below:
- F3C Ir CF3 (IV)
- 14 15
An organic electronic device comprising an emitting layer that comprises a compound selected from the following (i) and (ii):
- (i) a compound having a formula selected from fac-Ir(L)3, mer-Ir(L)3, and combinations thereof, where L is a group selected from 1-a through 1-m and 1-q through 1-v, as shown in Table 1 and has structure (I) below:
- 16
- wherein:
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring,
- at least one of R1-R8 is selected from F, CnF2n+1, OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and
- A=C or N, provided that when A N, there is no R1;
- (ii) a compound having one of structures (IV), (V), (VI), (IX), and (X) below:
- 17 18
A compound selected from compounds 2-a through 2-aa as shown in Table 2, having structure (II) below:
- 19
- wherein:
- R9 is H;
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring;
- at least one of R1-R8 is selected from F, CnF2n+1, OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and
- A=C or N, provided that when A=N, there is no R1.
A compound having structure (III) below:
- 20
- wherein R17=CF3 and R10-R16 and R18-R20=H.
A compound having structure VII below:
- 21
- wherein:
- B=H, CH3, or C2H5;
- La, Lb, Lc, and Ld are the same or different from each other;
- and
- each of La, Lb, Lc, and Ld has structure (I) below:
- 22
- wherein:
- adjacent pairs of R1-R4 and R5-R8 can be joined to form a five- or six-membered ring,
- at least one of R1-R8 is selected from F, CnF2n+1a, OCnF2n+1, and OCF2X, where n=1-6 and X=H, Cl, or Br, and
- A=C or N, provided that when A=N, there is no R1.
Dependencies are inferred from the claim text.