Heteroleptic iridium complexes as dopants

• US 8,709,615 B2
• Filed: 07/28/2011
• Issued: 04/29/2014
• Est. Priority Date: 07/28/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kottas, Gregg, Ansari, Nasrin, Elshenawy, Zeinab, DeAngelis, Alan, Xia, Chuanjun
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US13/193,221
• Publication Number:
  US 20130026452A1
• Time in Patent Office: 1,006 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• 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 2211/1088 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 50/00 Organic light-emitting devices integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/624 containing six or more rings
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein n is 2.

3. The compound of claim 1, wherein R₁ is selected from the group consisting of branched alkyl, cyclic alkyl, bicyclic alkyl, and multicyclic alkyl.

4. The compound of claim 1, wherein R₁ contains one or more deuterium atoms.

5. The compound of claim 1, wherein R₃, R₄, R₅ and R₆ are independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combinations thereof.

6. The compound of claim 1, wherein at least one of R₃, R₄, R₅ and R₆ comprises a branched alkyl, cyclic alkyl, bicyclic alkyl, or a multicyclic alkyl.

7. The compound of claim 1, wherein R₃, R₄, R₅ or R₆ contain one or more deuterium atoms.

8. A first device comprising a first organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula;

9. The first device of claim 8, wherein the first device is a consumer product.

10. The first device of claim 8, wherein the first device comprises a lighting panel.

11. The first device of claim 8, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

12. The first device of claim 8, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

13. The first device of claim 8, wherein the organic layer further comprises a host.

14. The first device of claim 13, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C_nH_2n+1, OC_nH_2n+1, OAr₁, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_n+1, C≡

CC_nH_2n+1, Ar₁, Ar₁—

Ar₂, and C_nH_2n—

Ar₁;

wherein n is from 1 to 10; and

wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

15. The first device of claim 14, wherein the host has the formula:

16. The first device of claim 13, wherein the host is selected from the group consisting of:

17. The first device of claim 13, wherein the host is a metal complex.