Cyclometallated iridium carbene complexes for use as hosts

• US 20050260447A1
• Filed: 01/10/2005
• Published: 11/24/2005
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Thompson, Mark E., Djurovich, Peter, Brooks, Jason, Tamayo, Arnold, Alleyne, Bert, Li, Xiao-Chang
• Granted Patent: US 7,154,114 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as 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 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Abstract

An organic light emitting device is provided. The device has an anode, a cathode and an organic layer disposed between the anode and the cathode. The organic layer comprises a host and a dopant, and the host comprises a compound having at least one carbene atom coordinated to iridium, and the compound has the structure:

Claims

1. A light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a host and a dopant, and the host comprises a compound having at least one carbene atom coordinated to iridium, and the compound has the structure;

wherein the dotted lines represent optional double bonds;

ring A is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring with at least one carbon atom coordinated to Ir, wherein ring A can be optionally substituted with one or more substituents Ra;

R₁is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;

R₂—

R₅, and Ra are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, CO₂R′

, C(O)R′

, C(O)NR′

2, NR′

2, NO₂, OR′

, SR′

, SO₂, SOR′

, SO₃R′

, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and

additionally or alternatively, two R or Ra groups on the same or adjacent ring, together form independently 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, CF₃, C(O)OR′

, C(O)R′

, C(O)NR′

₂, NR′

₂, NO₂, OR′

, SR′

, SO₂, SOR′

, or SO₃R′

, 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 halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;

b is 0, 1, 2, or 3.

2. The device of claim 1, wherein the compound has the structure:

3. The device of claim 2, wherein at least one of Ra₁ and Ra₃ is F.

4. The device of claim 3, wherein the compound has the structure:

5. The device of claim 2, wherein the compound has the structure:

6. The device of claim 5, wherein the compound is selected from the group consisting of:

7. The device of claim 1, wherein ring A comprises a nitrogen heteroatom.

8. The device of claim 7, wherein the compound has the structure:

9. The device of claim 8, wherein the compound is selected from the group consisting of:

10. The device of claim 8, wherein the compound has the structure:

11. The device of claim 10, wherein the compound is selected from the group consisting of:

12. A light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a host and a dopant, and the host comprises a carbene ligand having the structure;

wherein the dotted lines represent optional double bonds;

ring A is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring,

wherein ring A can be optionally substituted with one or more substituents Ra;

R₁ is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;

R₂—

R₅, and Ra are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, CO₂R′

, C(O)R′

, C(O)NR′

2, NR′

2, NO₂, OR′

, SR′

, SO₂, SOR′

, SO₃R′

, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and

additionally or alternatively, two R or Ra groups on the same or adjacent ring, together form independently 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, CF₃, C(O)OR′

, C(O)R′

, C(O)NR′

₂, NR′

₂, NO₂, OR′

, SR′

, SO₂, SOR′

, or SO₃R′

, 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 halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;

b is 0, 1, 2, or 3.

13. The device of claim 12, wherein the ligand has the structure:

14. The device of claim 13, wherein at least one of Ra₁ and Ra₃ is F.

15. The device of claim 14, wherein the ligand has the structure:

16. The device of claim 13, wherein the ligand has the structure:

17. The device of claim 16, wherein the ligand is selected from the group consisting of:

18. The device of claim 12, wherein ring A comprises a nitrogen heteroatom.

19. The device of claim 18, wherein the ligand has the structure:

20. The device of claim 19, wherein the ligand is selected from the group consisting of:

21. The device of claim 19, wherein the ligand has the structure:

22. The device of claim 21, wherein the ligand is selected from the group consisting of: