Organic light emitting materials

• US 9,748,500 B2
• Filed: 01/15/2015
• Issued: 08/29/2017
• Est. Priority Date: 01/15/2015
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Su, Mingjuan, Xia, Chuanjun
• Primary Examiner(s): Kollias, Alexander
• Application Number:
  US14/597,857
• Publication Number:
  US 20160211469A1
• Time in Patent Office: 957 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 2211/1088 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: H10K 85/342 comprising iridium
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Phosphorescent iridium complexes comprising multi-alkyl-substituted aza-DBF and 2-phenylpyridine ligands is disclosed. These complexes are useful as emitters for phosphorescent OLEDs.

Claims

1. A compound having the formula Ir(L_A)_n(L_B)_3-n, having the structure:

2. The compound of claim 1, wherein, when R¹, R³, and R⁴ are alkyl or cycloalkyl, each is independently selected from the group consisting of 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, wherein each group is optionally partially or fully deuterated.

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

4. The compound of claim 1, wherein X is O.

5. The compound of claim 1, wherein R¹ and R⁴ are each independently selected from the group consisting of alkyl, cycloalkyl, and combinations thereof, wherein each group is optionally partially or fully deuterated, and R² and R³ are hydrogen.

6. The compound of claim 1, wherein R¹, R³, and R⁴ are each independently selected from the group consisting of alkyl, cycloalkyl, and combinations thereof, wherein each group is optionally partially or fully deuterated and R² is hydrogen.

7. The compound of claim 1, wherein the total carbon number of R¹, R², R³, and R⁴ are at least 3.

8. The compound of claim 1, wherein R_a, R_b, and R_c are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

9. The compound of claim 1, wherein L_A has a structure according to the following formula:

10. The compound of claim 1, wherein L_B is selected from the group consisting of:

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

12. A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound having a formula Ir(L_A)_n(L_B)_3-n, having the structure;

13. The device of claim 12, wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

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

15. The device of claim 12, 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.

16. The device of claim 12, 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.

17. The device of claim 12, wherein the organic layer further comprises a host and the host is selected from the group consisting of:

18. A formulation comprising a compound having a formula Ir(L_A)_n(L_B)_3-n, having the structure: