Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes

Patent metadata

Field	Value
Publication number	US-12565486-B2
Application number	US-202418758770-A
Country	US
Kind code	B2
Filing date	Jun 28, 2024
Priority date	Aug 15, 2014
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

Complexes and devices, such as organic light emitting devices and full color displays, including a compound of the formula:

wherein:
M is Pd 2+ , Ir + , Rh + , or Au 3+ ;
each of V 1 , V 2 , V 3 , and V 4 is coordinated to M and is independently N, C, P, B, or Si;
each of L 1 , L 2 , L 3 , and L 4 is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and
Z is O, S, NR, CR 2 , SiR 2 , BR, PR,

 where each R is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl.

First claim

What is claimed is:

1 . A compound of General Formula I:

wherein:
M is Pd 2+ , Ir + , Rh + , or Au 3+ ;
each of V 1 , V 2 , V 3 , and V 4 is coordinated to M and is independently N, C, P, B, or Si;
each of L 1 , L 2 , L 3 , and L 4 is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene;
wherein at least one of L 1 , L 2 , L 3 , and L 4 comprises the N-heterocyclic carbene of a formula:

that is bonded to M by way of the wavy line; and
Z is O, S, NR, CR 2 , SiR 2 , BR, PR,

where each R is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl.

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

wherein:
each R 1 , R 2 , R 3 , and R 4 represents a non-hydrogen substituent and is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl;
each n is independently an integer of 0 to 3, valency permitting; and
each of Y 1a , Y 2a , Y 1b , Y 2b , Y 3a , Y 3c , Y 3d , Y 4a , Y 4b , Y 4c , Y 4d is independently N, NR 4a , or CR 4b , where each R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl.

3 . The compound of claim 2 , wherein the compound has one of the following structures:

4 . The compound of claim 1 , wherein the compound has the following structure:

wherein:
each R 1 , R 2 , R 3 , and R 4 represents a non-hydrogen substituent and is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl;
each n is independently an integer of 0 to 4, valency permitting; and
each of Y 1a , Y 1b , Y 1c , Y 2a , Y 2b , Y 2c , Y 3a , Y 3b , Y 4a , Y 4b is independently N, NR 4a , or CR 4b , wherein each R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, or thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, substituted or unsubstituted aryl.

5 . The compound of claim 1 , wherein the compound has the following structure:

wherein:
each R 1 , R 2 , R 3 , and R 4 represents a non-hydrogen substituent and is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl;
each n is independently an integer of 0 to 4, valency permitting; and
each of Y 1a , Y 1b , Y 2a , Y 2b , Y 2c , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , and Y 4d is independently N, NR 4a , or CR 4b , wherein each R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl, hydroxyl, amino, nitro, or thiol.

6 . The compound of claim 5 , wherein the compound has one of the following structures:

7 . The compound of claim 1 , wherein the compound has the following structure:

wherein:
each R 1 , R 2 , R 3 , and R 4 represents a non-hydrogen substituent and is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl;
each n is independently an integer of 0 to 4, valency permitting; and
each of Y 1a , Y 1b , Y 2a , Y 2b , Y 2c , Y 3a , Y 3b , Y 4a , Y 4b , is independently N, NR 4a , or CR 4b , wherein each R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, or thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl.

8 . The compound of claim 1 , wherein the compound has the following structure:

wherein:
each R 1 , R 2 , R 3 , and R 4 represents a non-hydrogen substituent and is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl;
each n is independently an integer of 0 to 4, valency permitting; and
each of Y 1a , Y 1b , Y 2a , Y 2b , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , and Y 4d is independently N, NR 4a , or CR 4b , wherein each R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, or thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl.

9 . The compound of claim 8 , wherein the compound has one of the following structures:

10 . A light emitting device comprising the compound of claim 1 .

11 . An OLED device comprising the compound of claim 1 .

12 . The OLED device of claim 10 , wherein the device is a phosphorescent OLED device.

13 . A photovoltaic device comprising the compound of claim 1 .

14 . A luminescent display device comprising the compound of claim 1 .

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Huang Liang
• Fleetham Tyler

Classifications

• C09K2211/18

  Metal complexes · CPC title

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• C07F15/0073

  Rhodium compounds · CPC title

• H10K59/10

  OLED displays · CPC title

• H10K2101/10

  Triplet emission · CPC title