Organic electroluminescent materials and devices

• US 9,484,541 B2
• Filed: 10/20/2014
• Issued: 11/01/2016
• Est. Priority Date: 10/20/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Boudreault, Pierre-Luc T., Elshenawy, Zeinab, Xia, Chuanjun
• Primary Examiner(s): Lee, Kyoung
• Application Number:
  US14/518,552
• Publication Number:
  US 20160111661A1
• Time in Patent Office: 743 Days
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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

Abstract

A compound having a formula M(L_A)_x(L_B)_y(L_C)_z, where ligand L_A is

ligand L_B is

and ligand L_C is

is disclosed. In the structure of M(L_A)_x(L_B)_y(L_C)_z, M is a metal; x is 1, or 2; y and z are 0, 1, or 2; X¹, X², X³, X⁴, X⁵, X⁶, X⁷, and X⁸ are each independently C or N; rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; two adjacent R^B form a six-member aromatic carbocyclic or heterocyclic ring E fused to ring B and, when ring E is heterocyclic, the only heteroatom is nitrogen; and ring E can be further substituted by R^E. Additionally, any adjacent substituents R¹¹, R¹², R^B, R^C, R^D, R^E, R¹, R², R³, R⁴, R′ and R″ are optionally joined to form a ring. Formulations and devices that include the compound of formula M(L_A)_x(L_B)_y(L_C)_z, are also described.

Claims

1. A compound having a formula M(L_A)_x(L_B)_y(L_C)_z:

wherein ligand L_A is

2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1, wherein M is Ir.

4. The compound of claim 1, wherein R′

and R″

are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof.

5. The compound of claim 1, wherein R′

and R″

are joined to form a ring.

6. The compound of claim 1, wherein the compound has the formula M(L_A)₂(L_B).

7. The compound of claim 1, wherein the compound has the formula M(L_A)(L_C)₂.

8. The compound of claim 1, wherein R¹¹ is selected from the group consisting of alkyl, and partially or fully deuterated variants thereof.

9. The compound of claim 1, wherein X⁵, X⁶, X⁷, and X⁸ are C.

10. The compound of claim 1, wherein X¹, X², X³, and X⁴ are C;

and ring E is benzene.

11. The compound of claim 1, wherein (a) at least one of X¹, X², X³, and X⁴ is N, (b) ring E is heterocylic, or (c) both (a) and (b).

12. The compound of claim 1, wherein L_A has the formula selected from the group consisting of:

13. The compound of claim 1, wherein L_B has the formula:

14. The compound of claim 1, wherein ring C is benzene, and ring D is pyridine.

15. The compound of claim 1, wherein L_A is selected from the group consisting of L_A1 to L_A252 listed below:

16. The compound of claim 15, wherein the compound is selected from the group consisting of Compound 1 through Compound 3,276;

wherein each Compound x has the formula Ir(L_Ak)₂(L_Bj), wherein x=252j+k−

252, k is an integer from 1 to 252, and j is an integer from 1 to 13, wherein L_B is selected from the group consisting of;

17. The compound of claim 1, wherein L_B is selected from the group consisting of L_B1 to L_B13:

18. A first device comprising a first organic light emitting device, the 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 a formula M(L_A)_x(L_B)_y(L_C)_z;

wherein ligand L_A is

19. The first device of claim 18, wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

20. The first device of claim 18, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

21. The first device of claim 18, wherein the organic layer further comprises a host, 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, C_nH_2n—

Ar₁, or no substitution;

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.

22. The first device of claim 18, wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

23. The first device of claim 18, wherein the organic layer further comprises a host and the host is selected from the group consisting of:

24. A formulation comprising a compound having a formula M(L_A)_x(L_B)_y(L_C)_z:

wherein ligand L_A is