Organic electroluminescent materials and devices

• US 9,663,544 B2
• Filed: 07/25/2012
• Issued: 05/30/2017
• Est. Priority Date: 07/25/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kottas, Gregg, Tsai, Jui-Yi
• Primary Examiner(s): Yamnitzky, Marie R.
• Application Number:
  US13/558,250
• Publication Number:
  US 20140027716A1
• Time in Patent Office: 1,770 Days
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• 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 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• 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

Abstract

Heteroleptic cyclometallated complexes having a 6-membered ring cyclometallated to the metal, as shown in Formula (I), are provided:

wherein ring A and ring B are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein L₁ is BR, NR, PR, O, S, Se, C═O, S═O, SO₂, CRR′, SiRR′, or GeRR; wherein Z₁ and Z₂ are independently carbon or nitrogen; wherein at least one of Z₁ and Z₂ is carbon; wherein

is a bidentate ligand selected from the group consisting of:

wherein R₁, R₂, R_a, R_b, R_c, and R_d may represent mono, di, tri, or tetra substitution, or no substitution; wherein R₁, R₂, R, R′, R_a, R_b, R_c, and R_d are each independently selected from various substituents; and wherein n is 1 or 2. Devices, such as organic light emitting devices (OLEDs) that comprise phosphorescent light emitting materials are also provided.

Claims

1. A compound of Formula (I):

2. The compound of claim 1, wherein

3. The compound of claim 1, wherein A-L₁-B is

4. The compound of claim 3, wherein L₁ is CRR′

, wherein R and R′

are alkyl.

5. The compound of claim 4, wherein CRR′

is C(CH₃)₂.

6. The compound of claim 1, wherein A-L₁-B is:

7. The compound of claim 1, wherein A-L₁-B is

8. The compound of claim 1, wherein the ring A is an imidazole ring, which may be substituted as indicated, and Z₁ is nitrogen.

9. The compound of claim 1, wherein A-L₁-B is

10. The compound of claim 1, wherein

11. The compound of claim 1, which is selected from the group consisting of:

12. 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 of Formula (I);

13. The first device of claim 12, wherein the first device is a consumer product.

14. The first device of claim 12, wherein the first device is an organic light-emitting device.

15. The first device of claim 12, wherein the first device comprises a lighting panel.

16. The first device of claim 12, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

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

18. The first device of claim 12, wherein the organic layer further comprises a host.

19. The first device of claim 18, 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_nH_2n+1, C≡

CC_nH_2n+1, Ar₁, Ar₁—

Ar₂, and C_nH_2n—

Ar₁, or the host has no substitutions;

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.

20. The first device of claim 18, wherein the host is selected from the group consisting of:

21. The first device of claim 18, wherein the host comprises a metal complex.

22. The first device of claim 18, wherein the host comprises at least one of the chemical groups selected from the group consisting of carbazole, dibenzothiophene dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.