Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12552986-B2
Application number	US-202217881372-A
Country	US
Kind code	B2
Filing date	Aug 4, 2022
Priority date	Jun 20, 2016
Publication date	Feb 17, 2026
Grant date	Feb 17, 2026

Abstract

Iridium complexes comprising three different bidentate ligands and their use in OLEDs to enhance the device efficiency and lifetime are disclosed. The complexes have a structure of the formula Ir(L A )(L B )(L C ), where ligand L A is selected from a variety of structures, ligand L B has the structure

and L C has the structure

In these structures rings A, B, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; R 1 , R 2 , R 3 , R A , R B , R C , and R D can be any of a variety of substituents, and Z 1 and Z 2 are each independently C or N.

First claim

The invention claimed is:

1 . A compound having a formula Ir(L A )(L B )(L C ) selected from

wherein L A is the ligand with substituents R 1 , R 2 , and R 3 ;
wherein L B is the ligand with substituents R A1 , R A2 , and R B ;
wherein L C is the ligand with substituents R C and R D ;
wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D each independently represents mono, to a maximum possible number of substitutions, or no substitution;
wherein L A , L B , and L C are different from each other, and can be connected to each other to form multidentate ligand;
wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two or more substituents among R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are optionally joined or fused into a ring; and
wherein at least one of the following is true:
(i) at least one R 1 , R 2 , R 3 , R A , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof; or
(ii) an R B is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and (a) the R B is joined with an adjacent R B that together with the ring coordinated to the Ir atom forms a dibenzofuran or aza-dibenzofuran moiety, or (b) at least one R A1 , R A2 , or R B is a partially or fully deuterated alkyl or partially or fully fluorinated alkyl.

2 . The compound of claim 1 , wherein at least two of R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D are independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.

3 . The compound of claim 1 , wherein at least one of L A , L B , and L C , is selected from the group consisting of:

where i in Ai is 1 to 212 and the substituents in L a Ai , L c Ai , and L d Ai are defined as,

L a Ai

L c Ai ,

and

L d Ai ,

where i

is
R 1a
R 1b
R 2
R 3a
R 3b
R 3c

1.
H
H
H
H
H
H

2.
H
CH3
H
H
H
H

3.
H
CD3
H
H
H
H

4.
H
C2H5
H
H
H
H

5.
H
CD2CH3
H
H
H
H

6.
H
CHMe2
H
H
H
H

7.
H
CDMe2
H
H
H
H

8.
H

H
H
H
H

9.
H

H
H
H
H

10.
H

H
H
H
H

11.
H

H
H
H
H

12.
H

H
H
H
H

13.
H

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Ji Zhiqiang
• Dyatkin Alexey Borisovich
• Xia Chuanjun
• Lin Chun
• Zeng Lichang
• Yeager Walter

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title