Novel organometallic compounds for use in electroluminescent devices

• US 20050260448A1
• 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: Tsai, Jui-Yi, Thompson, Mark E., Lin, Chun, Djurovich, Peter, Walters, Robert, Brooks, Jason, Sajoto, Tissa, Tamayo, Arnold, Alleyne, Bert
• Granted Patent: US 7,534,505 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
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic light emitting device having an anode, a cathode and an organic layer between the anode and the cathode is provided. The organic layer comprises a carbene-metal complex having the structure:
where R may be halo, hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and additionally or alternatively, two or more R groups on the same ring form independently a 5 or 6-member cyclic group, which may be cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and which may be substituted by one or more substituents J; and J may be 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′ may be halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl and heteroaryl.

Claims

1. 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 further comprising one or more carbene ligands coordinated to a metal center, wherein the compound has the structure;

wherein M is a metal;

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

R₂, R₃, R₈, R₁₀, R₁₁, and R₁₂ 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, one or more of R₁ and R₂, and R₂ and R₃, and two R₈ groups, two R₁₀ groups, and two R₁₂ groups on the same 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;

(X—

Y) is selected from a photoactive ligand or an ancillary ligand;

d is 0, 1, 2, 3, or 4;

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.

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

3. The device of claim 2, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

4. The device of claim 3, wherein M is Ir.

5. The device of claim 4, wherein m is 3 and n is 0.

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 further comprises a carbene ligand having the structure;

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

R₂, R₃, R₈, R₁₀, R₁₁, and R₁₂ 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, one or more of R₁ and R₂, and R₂ and R₃, and two R₈ groups, two R₁₀ groups, and two R₁₂ groups on the same 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;

(X—

Y) is selected from a photoactive ligand or an ancillary ligand,

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

7. The device of claim 6, wherein the ligand is selected from the group consisting of:

8. A compound selected from the group consisting of:

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

10. The compound of claim 9, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

11. The compound of claim 10, wherein M is Ir.

12. The compound of claim 11, wherein m is 3 and n is 0.