Metal complexes of cyclometallated imidazo[1,2-ƒ]phenanthridine and diimidazo[1,2-a:1',2'-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof

• US 20070190359A1
• Filed: 02/09/2007
• Published: 08/16/2007
• Est. Priority Date: 02/10/2006
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Knowles, David, Beers, Scott, Yeager, Walter, Lin, Chun, Walters, Robert, Brown, Cory, MacKenzie, Peter
• Granted Patent: US 7,915,415 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• 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 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1055 with other heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1062 with oxygen
• CPC Class Codes: C09K 2211/1066 with sulfur
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1081 with sulfur
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur 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 2102/321 : Inverted OLED, i.e. having cathode between substrate and anode
• CPC Class Codes: H10K 50/11 : characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/346 : comprising platinum
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene

Abstract

Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting diode devices comprising these compounds are also described.

Claims

1. A compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand selected from Set 1, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein;

E^1a-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system;

provided that E^1a and E^1p are different; and

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

2. The compound according to claim 1, wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, Cu, and Au, and the bidentate ligand is selected from Set 2;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2aSR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

3. The compound according to claim 2, wherein the bidentate ligand is of the formula gs1-1.

4. The compound according to claim 1, wherein the metal is Ir or Pt and the bidentate ligand is selected from Set 2.

5. The compound according to claim 1, wherein the metal complex is a homoleptic Ir complex of a ligand selected from Set 2.

6. The compound according to claim 1, wherein the metal complex is a heteroleptic Ir complex comprising two bidentate ligands selected from Set 2 and a third monoanionic bidentate ligand.

7. The compound according to claim 6, wherein the third monoanionic bidentate ligand is acetylacetonate or a substituted acetylacetonate.

8. The compound according to claim 1, wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, Cu, and Au, and at least one of R^1a-i is a 2,6-di-substituted aryl group.

9. The compound according to claim 1, wherein the metal is selected from the group consisting of Ir and Pt, the ligand is of formula gs1-1 and R^1b is a 2,6-di-substituted aryl group.

10. The compound according to claim 9, wherein the 2,6-di-substituted aryl group is selected from the group consisting of 2,6-dimethylphenyl;

2,4,6-trimethylphenyl;

2,6-di-isopropylphenyl;

2,4,6-triisopropylphenyl;

2,6-di-isopropyl-4-phenylphenyl;

2,6-dimethyl-4-phenylphenyl;

2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl;

2,6-diphenylphenyl;

2,6-diphenyl-4-isopropylphenyl;

2,4,6-triphenylphenyl;

2,6-di-isopropyl-4-(4-isopropylphenyl)phenyl;

2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl;

2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl;

2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and

2,6-di-(3,5-dimethylphenyl)phenyl.

12. An OLED device comprising any of the compounds of claims 1 or 11.

11. A compound selected from Set 3, wherein acac is acetylacetonate;

13. A compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand selected from Set 4, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein;

E^1a-q are each, independently, selected from the group consisting of C and N, and collectively comprise an 18 pi-electron system;

provided that E^1a and E^1p are different; and

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

14. The compound according to claim 13, wherein the bidentate ligand is selected from Set 5;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a ring.

15. The compound according to claim 13, wherein the bidentate ligand is selected from Set 6;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a ring.

16. The compound according to claim 14, wherein the bidentate ligand is substituted by one or more 2,6-disubstituted aryl or heteroaryl groups.

17. The compound according to claim 16, wherein the 2,6-di-substituted aryl group is selected from the group consisting of 2,6-dimethylphenyl;

2,4,6-trimethylphenyl;

2,6-di-isopropylphenyl;

2,4,6-triisopropylphenyl;

2,6-di-isopropyl-4-phenylphenyl;

2,6-dimethyl-4-phenylphenyl;

2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl;

2,6-diphenylphenyl;

2,6-diphenyl-4-isopropylphenyl;

2,4,6-triphenylphenyl;

2,6-di-isopropyl-4-(4-isopropylphenyl)phenyl;

2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl;

2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl;

2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and

2,6-di-(3,5-dimethylphenyl)phenyl.

18. The compound according to claim 14, wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, Cu and Au.

19. The compound according to claim 14, wherein the metal is selected from the group consisting of Os, Ir and Pt.

20. The compound according to claim 14, wherein the metal is Ir.

21. An OLED device comprising a compound of claim 14.

22. A compound corresponding to a ligand of claim 14, wherein the metal has been replaced by H.

23. A compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand selected from Set 7, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand comprises a carbene donor and may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein;

E^1a-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system;

provided that E^1a and E^1p are both carbon; and

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

24. The compound according to claim 23, wherein the compound is selected from Set 8;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

25. An OLED device comprising a compound of claim 23.

26. A compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand selected from Set 9, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand comprises a carbene donor and may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein;

E^1a-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system;

provided that E^1a and E^1p are both carbon; and

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

27. The compound according to claim 26, wherein the compound is selected from Set 10;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

28. An OLED device comprising a compound of claim 26.

29. A compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand selected from Set 11, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein;

R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N.

30. An OLED device comprising a compound of claim 29.

31. A compound corresponding to a ligand of claim 29, wherein the metal has been replaced by H.

32. A compound comprising a metal complex selected from Table 1.

33. An OLED device comprising a compound of claim 32.