Organic electroluminescent materials and devices

• US 9,540,329 B2
• Filed: 07/19/2012
• Issued: 01/10/2017
• Est. Priority Date: 07/19/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Beers, Scott, Xia, Chuanjun, Layek, Suman, Wendt, Harvey
• Primary Examiner(s): Chriss, Jennifer
• Assistant Examiner(s): KERSHNER, DYLAN CLAY
• Application Number:
  US13/553,495
• Publication Number:
  US 20140021447A1
• Time in Patent Office: 1,636 Days
• Field of Search: 428/690, 428/917, 257/40, 257/E51.041, 257/E51.044, 257/E51.043, 313/504, 313/505, 313/506, 546/4, 546/10, 548/103, 548/108
• US Class Current: 1/1
• CPC Class Codes: C07D 213/74 Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• 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

Heteroleptic complexes having at least one diarylamino or carbazole group, as shown in Formula (I), are provided:

• • wherein R₁, R₂, R₃, R₄, R₅, and R₆ each represent mono, di, tri, tetra, or penta substitutions or no substitution; wherein Z is a single bond connecting the two phenyl rings, or is absent, wherein when Z is absent, the positions on the phenyl rings may be substituted by R₅ or R₆; wherein any two adjacent substituents are optionally joined together to form a ring, which may be further substituted; wherein each of R₁, R₂, R₃, R₄, R₅, and R₆ is independently selected from various substituents; and wherein m is 1 or 2. Devices, such as organic light emitting devices (OLEDs) that comprise phosphorescent light emitting materials are also provided.

Claims

1. A first device comprising a first organic light emitting device, the first organic light emitting device further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a heteroleptic metal complex of Formula (V);

2. The first device of claim 1, wherein the heteroleptic metal complex is a compound of Formula (VI):

3. The first device of claim 1, wherein m is 1.

4. The first device of claim 1, wherein m is 2.

5. The first device of claim 1, wherein the heteroleptic metal complex is selected from the group consisting of:

6. The first device of claim 1, wherein the heteroleptic metal complex is selected from the group consisting of:

7. The first device of claim 1, wherein each of R₁, R₂, R₃, and R₄ is selected from the group consisting of:

hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, and partially or fully deuterated variations thereof.

8. The first device of claim 1, wherein each of R₁, R₂, R₃, and R₄ is selected from the group consisting of:

hydrogen, deuterium, alkyl, and combinations thereof.

9. The first device of claim 1, wherein each of R₁, R₂, R₃, and R₄ is selected from the group consisting of:

hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, and combinations thereof.

10. The first device of claim 1, wherein the first device is a consumer product.

11. The first device of claim 1, wherein the first device is an organic light-emitting device.

12. The first device of claim 1, wherein the first device comprises a lighting panel.

13. The first device of claim 1, wherein the organic layer is an emissive layer and the complex is an emissive dopant.

14. The first device of claim 1, wherein the organic layer is an emissive layer and the complex is a non-emissive dopant.

15. The first device of claim 1, wherein the organic layer further comprises a host.

16. The first device of claim 15, 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;

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.

17. The first device of claim 15, wherein the host is selected from the group consisting of:

18. The first device of claim 15, wherein the host comprises a metal complex.