Organic electroluminescent materials and devices

• US 9,548,462 B2
• Filed: 01/29/2016
• Issued: 01/17/2017
• Est. Priority Date: 02/10/2006
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Knowles, David, Lin, Chun, Mackenzie, Peter, Tsai, Jui-Yi, Walters, Robert W., Beers, Scott, Brown, Cory S., Yeager, Walter
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US15/010,560
• Publication Number:
  US 20160240798A1
• Time in Patent Office: 354 Days
• Field of Search: 546/10, 313/504
• US Class Current: 1/1
• 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 phosphorescent compound comprising a metal and a monoanionic, bidentate ligand as set forth below, 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;

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

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

4. The compound of claim 2, wherein the metal is Ir or Pt.

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

6. The compound of claim 5, wherein R^1b is a 2,6-di-substituted aryl group.

7. The compound of claim 6, wherein the metal is Ir or Pt.

8. The compound of claim 5, 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.

9. The compound of claim 1, wherein any two of R^1a-i may be linked to only form a saturated, or non-aromatic ring.

10. The compound of claim 2, wherein the compound is a homoleptic Ir complex.

11. The compound of claim 2, wherein the compound is a heteroleptic Ir complex.

12. The compound of claim 1, wherein R^1a-i are each independently H, fluoro, substituted or unsubstituted C₁-C₂₀ alkyl, substituted or unsubstituted C₃-C₈ cycloalkyl, or substituted or unsubstituted C₆-C₁₈ aryl;

and the metal is Ir or Pt.

13. The compound of claim 1, wherein the bidentate ligand is:

14. The compound of claim 13, wherein each of E^1e-o and E^1q is carbon.

15. The compound of claim 13, wherein at least one pair of R^1a-i are linked to form a saturated, or non-aromatic ring.

16. The compound of claim 15, wherein the compound is selected from the group consisting of:

17. An OLED device comprising the compound of claim 1.

18. An OLED device of claim 17, wherein the metal is Ir or Pt, and R^1b is a 2,6-di-substituted aryl group.

19. An OLED device of claim 17, wherein the bidentate ligand is

20. An OLED device comprising the compound of claim 3.