Carbene Metal Complexes as OLED Materials

Patent metadata

Field	Value
Publication number	US-2016268518-A1
Application number	US-201615074676-A
Country	US
Kind code	A1
Filing date	Mar 18, 2016
Priority date	May 18, 2004
Publication date	Sep 15, 2016
Grant date	—

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. In another aspect, the organic layer comprises a carbene compound, including the following:

In another aspect, the organic layer comprises a carbene compound, including:

In another aspect, the organic layer comprises a carbene compound that includes a triazole ring and has the structure:

In another aspect, the organic layer comprises a carbene compound that includes a tetrazole ring and has the structure:

First claim

1 - 15 . (canceled)

16 . A composition comprising a compound having at least one carbene atom coordinated to iridium, the compound 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 with at least one carbon atom coordinated to Ir, wherein ring A can be optionally substituted with one or more substituents Ra;
R 1 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R 2 -R 5 , and Ra 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; 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, 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 halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
b is 0, 1, 2, or 3.

17 . The composition of claim 16 , wherein the compound has the structure:

18 . The composition of claim 17 , wherein at least one of Ra 1 and Ra 3 is F.

19 . The composition of claim 18 , wherein the compound has the structure:

20 . The composition of claim 17 , wherein the compound has the structure:

wherein 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 Rb;
Rb is 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; and additionally or alternatively, two Rb 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, 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 halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
b is 0, 1, 2, or 3.

21 . The composition of claim 20 , wherein the compound is selected from the group consisting of:

22 . The composition of claim 16 , wherein ring A of the compound comprises a nitrogen heteroatom.

23 . The composition of claim 22 , wherein the compound has the structure:

wherein, additionally or alternatively, R 3 and Ra 1 and two adjacent Ra 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.

24 . The composition of claim 23 , wherein the compound is selected from the group consisting of:

25 . The composition of claim 23 , wherein the compound has the structure:

wherein ring C is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring, wherein ring C can be optionally substituted with one or more substituents Rc;
Rc is 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; and additionally or alternatively, two Rc 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, 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 halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
b is 0, 1, 2, or 3.

26 . The composition of claim 25 , wherein the compound is selected from the group consisting of:

27 . A composition comprising 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;
R 1 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R 2 -R 5 , and Ra 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; 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, 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 halo, H, alkyl, alke

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

• C07F15/0033

  Iridium compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• Y10S428/917

  Electroluminescent · CPC title