Carbene metal complexes as OLED materials

Patent metadata

Field	Value
Publication number	US-9356245-B2
Application number	US-201313847597-A
Country	US
Kind code	B2
Filing date	Mar 20, 2013
Priority date	May 18, 2004
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

An organic light emitting device having an anode, a cathode and an organic layer disposed between the anode and the cathode is provided. In one aspect, the organic layer comprises a compound having at least one zwitterionic carbon donor ligand.

First claim

What is claimed is:

1. A compound comprising a metal center and a ligand coordinated to the metal center, wherein the ligand is selected from:

wherein R 1 and R 2 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF 3 , CO 2 R′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, SO 3 R′, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
R 3 is selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, two R groups on the same or adjacent ring, together form a 5 or 6-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl; and wherein said cyclic group is optionally substituted by one or more substituents J;
each substituent J is independently selected from the group consisting of R′, CN, CF 3 , C(O)OR′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, or SO 3 R′, and additionally, or alternatively, two J groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;
each R′ is independently selected from H, halo, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
a is 0, 1, 2, 3, or 4; and b is 0, 1, 2, or 3.

2. The compound of claim 1 , wherein the metal center is Ir or Pt.

3. The compound of claim 2 , wherein the metal center is Ir.

4. The compound of claim 1 , wherein each of R 1 is H or an alkyl having 1-15 carbons; each of R 2 is H or an alkyl having 1-15 carbons; each of R 3 is H or an alkyl having 1-15 carbons.

5. The compound of claim 1 , wherein the compound is:

wherein M is the metal center;
(X—Y) is a photoactive ligand or an ancillary ligand;
m is a value from 1 to the maximum number of ligands that may be attached to metal M;
m+n is the maximum number of ligands that may be attached to metal M.

6. The compound of claim 5 , wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Al, Ge, Au, and Ag.

7. The compound of claim 5 , wherein M is Ir or Pt.

8. The compound of claim 7 , wherein M is Ir.

9. The compound of claim 8 , wherein m is 3 and n is 0.

10. The compound of claim 5 , wherein each of R 1 is H or an alkyl having 1-15 carbons; each of R 2 is H or an alkyl having 1-15 carbons; each of R 3 is H or an alkyl having 1-15 carbons.

11. The compound of claim 5 , wherein the compound is:

and a is 0, 1, 2, or 3.

12. An organic light emitting device comprising:
an anode;
a cathode; and
an organic layer between the anode and the cathode, the organic layer comprising the compound of claim 1 .

13. The device of claim 12 , wherein the metal center is Ir or Pt.

14. The compound of claim 13 , wherein the metal center is Ir.

15. The compound of claim 12 , wherein each of R 1 is H or an alkyl having 1-15 carbons; each of R 2 is H or an alkyl having 1-15 carbons; each of R 3 is H or an alkyl having 1-15 carbons.

16. The device of claim 15 , wherein the organic layer is an emissive layer.

17. The compound of claim 1 , wherein the ligand is:

and a is 0, 1, 2, or 3.

Assignees

• Univ Southern California
• Universal Display Corp

Inventors

• Djurovich Peter
• Tsai Jui-Yi
• Lin Chun
• Brooks Jason
• Alleyne Bert
• Thompson Mark E
• Mackenzie Peter B
• Ma Bin

Classifications

• H01L51/5016

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• C07F15/0033

  Iridium compounds · CPC title