Transition metal complexes containing triazole and tetrazole carbene ligands

• US 8,692,241 B1
• Filed: 11/08/2012
• Issued: 04/08/2014
• Est. Priority Date: 11/08/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Zeng, Lichang, Ma, Bin, Lin, Chun
• Primary Examiner(s): Mandala, Victor A
• Application Number:
  US13/671,994
• Time in Patent Office: 516 Days
• Field of Search: 257/40, 257/E51.018, 257/E51.027, 546/4
• US Class Current: 257/40
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

Novel iridium complexes containing triazole and tetrazole carbene ligands are described. These metal complexes additionally contain dibenzo moieties such as dibenzothiophene and dibenzofuran, and the complexes have overall improved properties such as more saturated blue emission when used as emissive compounds in OLED devices.

Claims

1. A compound having the formula:

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

3. The compound of claim 1, wherein X¹-X² is selected from the group consisting of:

4. The compound of claim 1, wherein Y¹-Y² is selected from the group consisting of:

5. The compound of claim 1, wherein X¹-X² is selected from the group consisting of:

6. The compound of claim 1, wherein X¹-X² is selected from the group consisting of:

7. The compound of claim 5, wherein R¹ is alkyl.

8. The compound of claim 7, wherein the alkyl is deuterated or partially deuterated.

9. The compound of claim 6, wherein the compound has the formula:

10. The compound of claim 9, wherein R⁸ and R⁹ are alkyl.

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

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

an anode;

a cathode; and

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

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≡

CHC_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.

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

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

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