Near-infrared emitting organic compounds and organic devices using the same

• US 20080061681A1
• Filed: 09/11/2006
• Published: 03/13/2008
• Est. Priority Date: 09/11/2006
• Status: Active Grant

• Current Assignee: The Trustees of Princeton University (Princeton University), Board of Regents of the University of Michigan (University of Michigan), University of Southern California
• Original Assignee: The Trustees of Princeton University (Princeton University), Board of Regents of the University of Michigan (University of Michigan), University of Southern California
• Inventors: Forrest, Stephen, Thompson, Mark E., Djurovich, Peter, Borek, Carsten, Hanson, Kenneth, Sun, Yiru
• Granted Patent: US 7,598,381 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Certain iridium compounds which may comprise an iridium(III)-ligand complex having the general formula: (ĈN)₂—Ir—(N̂N). (ĈN) and (N̂N) may each represent a ligand coordinated to an iridium atom. The iridium compounds may have a primary phosphorescent photoluminescence peak wavelength in the near-infrared (IR) range. Also, organic devices that use certain iridium compounds. The organic device may comprise an organic layer and the organic layer may comprise any of the iridium compounds disclosed herein. Also, organic devices that use certain metalloporphyrin compounds. The metalloporphyrin compounds may comprise a core porphyrin structure with four pyrrole rings. The metalloporphyrin compounds may have a primary phosphorescent photoluminescence peak wavelength in the near-IR range.

Claims

1. An iridium compound having the formula:

wherein G₂ is a hydrogen, phenyl, substituted phenyl, or alkyl;

wherein G₁ is a hydrogen, aryl moiety, or heteroaryl moiety on any position of the adjoining pyrrole ring;

wherein G₃ is a hydrogen, aryl moiety, or heteroaryl moiety on any position of the adjoining pyrrole ring;

wherein X is a nitrogen or carbon atom; and

wherein the ligand

contains a phenylpyrazole moiety, phenylpyridine moiety, or phenyloxazol moiety.

2. The iridium compound of claim 1, wherein the compound has a primary phosphorescent photoluminescence peak wavelength in the near-infrared range.

3. The iridium compound of claim 2, wherein the compound has a primary phosphorescent photoluminescence peak wavelength greater than about 680 nm.

4. The iridium compound of claim 1, wherein the compound has a primary phosphorescent photoluminescence peak with a bandwidth less than about 60 nm.

5. The iridium compound of claim 1, wherein each of G₁ and G₃ is independently selected from the group consisting of:

wherein Z is selected from the group consisting of S, O, NH, and NR_A; and

wherein R_A is any alkyl group.

6. The iridium compound of claim 1, wherein the ligand

is selected from the group consisting of:

7. The iridium compound of claim 1, wherein any of the rings in the ligand

is substituted with an oxygen-containing group at one or more positions on the ring.

8. The iridium compound of claim 1, wherein the compound has a formula selected from the group consisting of:

9. The iridium compound of claim 1, wherein the compound has a formula selected from the group consisting of:

10. An organic device comprising an iridium compound, wherein the iridium compound has the formula:

wherein G₂ is a hydrogen, phenyl, substituted phenyl, or alkyl;

wherein G₁ is a hydrogen, aryl moiety, or heteroaryl moiety on any position of the adjoining pyrrole ring;

wherein G₃ is a hydrogen, aryl moiety, or heteroaryl moiety on any position of the adjoining pyrrole ring;

wherein X is a nitrogen or carbon atom; and

wherein the ligand

contains a phenylpyrazole moiety, phenylpyridine moiety, or phenyloxazol moiety.

11. The organic device of claim 10, wherein the compound has a primary phosphorescent photoluminescence peak wavelength in the near-infrared range.

12. The organic device of claim 11, wherein the compound has a primary phosphorescent photoluminescence peak wavelength greater than about 680 nm.

13. The organic device of claim 10, wherein the compound has a primary phosphorescent photoluminescence peak with a bandwidth less than about 60 nm.

14. The organic device of claim 10, wherein each of G₁ and G₃ is independently selected from the group consisting of:

wherein Z is selected from the group consisting of S, O, NH, and NR_A; and

wherein R_A is any alkyl group.

15. The organic device of claim 10, wherein the ligand

is selected from the group consisting of:

16. The compound of claim 10, wherein any of the rings in the ligand

is substituted with an oxygen-containing group at one or more positions on the ring.

17. The organic device of claim 10, wherein the iridium compound has a formula selected from the group consisting of:

18. The organic device of claim 10, wherein the iridium compound has a formula selected from the group consisting of:

19. The device of claim 10, further comprising:

an anode;

a cathode;

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the iridium compound.

20. The organic device of claim 19, wherein the device is a light-emitting diode and wherein the organic layer is an emissive layer.

21. The organic device of claim 20, wherein the organic layer further comprises a host material, and wherein the absorption spectrum of the iridium compound overlaps with the electroluminescence emission spectrum of the host material.

22. The organic device of claim 21, wherein the iridium compound substantially quenches the electroluminescence emission spectrum of the host material.

23. An organic device comprising a metalloporphyrin compound, wherein the compound comprises a plurality of pyrrole rings and has a formula:

wherein M is a metal;

wherein each of R₁ to R₄ is independently selected from the group consisting of an aliphatic moiety, aryl moiety, heteroaryl moiety, and macrocycle moiety;

wherein each of R₁′

to R₄′

is independently selected from the group consisting of a hydrogen, phenyl, mesityl, and methyl; and

wherein the compound has a primary phosphorescent photoluminescence emission peak wavelength in the near-infrared range.

24. The organic device of claim 23, wherein the compound has a primary phosphorescent photoluminescence emission peak wavelength greater than about 680 nm.

25. The organic device of claim 23, wherein the compound has a primary phosphorescent photoluminescence emission peak with a bandwidth less than about 60 nm.

26. The organic device of claim 23, wherein each of R₁ to R₄ is an aryl moiety or heteroaryl moiety.

27. The organic device of claim 26, wherein each of R₁ to R₄ is independently selected from the group consisting of:

28. The organic device of claim 26, wherein each of R₁ to R₄ is fused to the adjoining pyrrole ring.

29. The organic device of claim 23, wherein M is platinum.

30. The organic device of claim 23, wherein each of R₁′

to R₄′

is a phenyl.

31. The organic device of claim 23, wherein the metalloporphyrin compound has the formula:

32. The organic device of claim 23, further comprising:

an anode,

a cathode, and

an organic layer disposed between the anode and the cathode, wherein organic layer comprises the metalloporphyrin compound.

33. The organic device of claim 23, wherein the device is a light-emitting diode and wherein the organic layer is an emissive layer.