CARBENE CONTAINING METAL COMPLEXES AS OLEDS

• US 20090302754A1
• Filed: 08/18/2009
• Published: 12/10/2009
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Arnold Tamayo, Jui-Yi Tsai, Mark Thompson, Michael S. Barone
• Original Assignee: Arnold Tamayo, Jui-Yi Tsai, Mark Thompson, Michael S. Barone
• Inventors: TSAI, Jui-Yi, BARONE, Michael S., TAMAYO, Arnold, THOMPSON, Mark E.
• Granted Patent: US 7,956,192 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• 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

A process for preparing a compound having the formula L₂IrL′ is provided. The process comprises:

combining

and L′ in the presence of an organic solvent to form a mixture, wherein L is a suitable carbene ligand precursor coordinated to Ir; and L′ is a bidentate ligand or two monodentate ligands, and L is different from L′;

Also provided is a process for preparing a compound having the formula

The process comprises:

• • (a) combining L, a carbene ligand precursor, with an organic solvent;
  • (b) maintaining the mixture of step (a) at a temperature from about 175° C. to less than the boiling point of the organic solvent in (a).

A process for preparing a compound with the formula L₃Ir is also provided. This process comprises combining

and L in the presence of alcohol and a base to form a mixture, wherein L is a bidentate ligand that may form a five-membered chelate ring.

Claims

1-4. -4. (canceled)

5. A compound, having the structure:

prepared from the process comprising;

(a) combining

in the presence of an organic solvent to form a mixture;

(b) maintaining the mixture for sufficient time to obtain

and

(c) recovering

from the mixture.

6. An organic 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 compound having the formula;

7. A compound having the formula:

wherein L is a carbene ligand coordinated to Ir.

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

and

A is independently C or N;

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

R₂₁, R₂₂, and R₃ 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, R₂₁ and R₂₂, and/or two R₃ groups on adjacent ring atoms form a fused 4-7-membered aromatic group, wherein said aromatic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said aromatic 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 4-7-membered aromatic group;

each R′

is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;

a is 0, 1, 2, 3, or 4.

9. The compound of claim 8, wherein L has the structure:

wherein R₃₁-R₃₄ are each 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, R₂₁ and R₂₂, and two R₃ groups on adjacent ring atoms form a fused 4-7-membered aromatic group, wherein said aromatic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said aromatic 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 4-7-membered aromatic group;

each R′

is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl.

10. The compound of claim 9, wherein L has the structure:

11. A process for preparing a compound having the formula

comprising:

(a) combining L with an organic solvent, wherein L is a suitable carbene ligand precursor;

(b) maintaining the mixture of (a) for a sufficient time at a temperature from about 175°

C. to less than the boiling point of the organic solvent in (a) to obtain

and

(c) recovering

from the mixture.

12. The process of claim 11, wherein the temperature at (b) is at least about 185°

C.

13. A process for preparing a compound with the formula L₃Ir, wherein L is a bidentate ligand and L forms a five-membered metal chelate ring, comprising:

(a) combining

and L in the presence of alcohol and a base to form a mixture;

(b) maintaining the mixture for sufficient time to obtain L₃Ir; and

(c) recovering L₃Ir from the mixture.

14. The process of claim 13, wherein L has the structure:

wherein A is independently C or N;

X is an alkyl group;

Y is N, P, or C;

ring B is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring, wherein ring B can be optionally substituted with one or more substituents R₃; and

ring B2 is independently a cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents Ra₃;

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

R₂₁, R₂₂, R₃, Ra₁, Ra₂₁, Ra₂₂, Ra₂₃, and Ra₃ are each 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, R₂₁ and R₂₂, two R₃ groups, Ra₁ and Ra₂₁, Ra₂₁ and Ra₂₂, Ra₂₂ and Ra₂₃, and two Ra₃ groups on adjacent ring atoms form a fused 4-7-membered aromatic group, wherein said aromatic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said aromatic 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 4-7-membered aromatic group;

each R′

is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl; and

b is 0, 1, or 2.

15. The process of claim 14, wherein L has the structure:

wherein R₃₁-R₃₄ and Ra₃₁-Ra₃₄ are each 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, R₂₁ and R₂₂, two R₃ groups, Ra₁ and Ra₂₁, Ra₂₁ and Ra₂₂, Ra₂₂ and Ra₂₃, and two Ra₃ groups on adjacent ring atoms form a fused 4-7-membered aromatic group, wherein said aromatic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said aromatic 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 4-7-membered aromatic group;

each R′

is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl.

16. The process of claim 15, wherein L has the structure:

17. A compound L₃Ir selected from the group consisting of:

prepared from a process comprising;

(a) combining

and L in the presence of alcohol and a base to form a mixture, wherein L is selected from the group consisting of;

(b) maintaining the mixture for sufficient time to obtain L₃Ir; and

(c) recovering L₃Ir from the mixture.