Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12534485-B2
Application number	US-202117515778-A
Country	US
Kind code	B2
Filing date	Nov 1, 2021
Priority date	Nov 24, 2020
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

Provided are organometallic compounds having a formula Ir(L A )(L B )(L C ), wherein:
ligand L A is

 ligand L B is

 and

ligand L C is

Also provided are formulations including these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

First claim

What is claimed is:

1 . A compound having a formula Ir(L A )(L B )(L C ), wherein:
ligand L A is

 ligand L B is

 and
ligand L C is

wherein:
ring A and ring B are each independently monocyclic or polycyclic structures comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
Z 1 and Z 2 are each independently C or N;
R has a structure of either Formula I

 or Formula II

L is a direct bond or an organic linking group;
each of R 1 , R 2 , R 3 , and R 4 is independently hydrogen or a substituent selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof,
at least two of R 1 , R 2 , and R 3 are not hydrogen, and R 1 , R 2 , and R 3 include a total of at least three carbon atoms;
each of R A , R B , R C , R D , and R F independently represents mono to the maximum allowable substitution, or no substitution;
each of R A , R B , R C , R D , R F , R X , R Y , and R Z is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two of R 1 , R 2 , R 3 , R 4 , R A , R B , R C , R D , R F , R X , R Y , and R Z can be joined or fused together to form a ring.

2 . The compound of claim 1 , wherein each of R A , R B , R C , R D , R F , R X , R Y , and R Z is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein Ring A is selected from the group consisting of pyridine, imidazole, phenyl, quinoline, isoquinoline, benzimidazole, pyrimidine, pyrazine and triazines.

4 . The compound of claim 1 , wherein Ring B is selected from the group consisting of pyridine, imidazole, phenyl, quinoline, isoquinoline, benzimidazole, pyrimidine, naphthalene, phenanthrene, dibenzofuran, fluorene, and dibenzothiophene.

5 . The compound of claim 1 , wherein R has a structure of Formula I.

6 . The compound of claim 5 , wherein each of R 1 , R 2 , and R 3 is independently hydrogen or a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

7 . The compound of claim 1 , wherein R has a structure of Formula II.

8 . The compound of claim 7 , wherein R 4 is a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

9 . The compound of claim 1 , wherein L is a direct bond; or an organic linker selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.

10 . The compound of claim 1 , wherein two R C are joined to form a fused ring.

11 . The compound of claim 1 , wherein at least two of R X , R Y , and R Z are independently a substituent selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, and combinations thereof; or R X , R Y , and R Z include a total of at least 6 carbon atoms.

12 . The compound of claim 1 , wherein ligand L C is selected from the group consisting of:

13 . The compound of claim 1 , wherein L A is selected from the group consisting of:

wherein:
T is selected from the group consisting of B, Al, Ga, and In;
each of Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R d independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.

14 . The compound of claim 1 , wherein L B is selected from the group consisting of

15 . The compound of claim 14 , wherein
when the compound has formula Ir(L Ai-k )(L Bm )(L Cj-I ), i is an integer from 1 to 200; k is an integer from 1 to 44; j is an integer from 1 to 1416; m is an integer from 1 to 15; and the compound is selected from the group consisting of Ir(L A1-1 )(L B1 )(L C1-I ) to Ir(L A200-44 )(L B15 )(L C1416-I ); and when the compound has formula Ir(L Ai-k )(L Bm )(L Cj-II ), i is an integer from 1 to 200; k is an integer from 1 to 44; j is an integer from 1 to 1416; m is an integer from 1 to 15; and the compound is selected from the group consisting of Ir(L A1-1 )(L B1 )(L C1-II ) to Ir(L A200-44 )(L B15 )(L C1416-II ); wherein each L Ai-k has the structure defined as follows when k is 1, L A1-1 to L A200-1 have the structure,

when k is 2, L A1-2 to L A200-2 have the structure,

when k is 3, L A1-3 to L A200-3 have the structure,

when k is 4, L A1-4 to L A200-4 have the structure,

when k is 5, L A1-5 to L A200-5 have the structure,

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Fitzgerald George
• Dyatkin Alexey Borisovich
• Ji Zhiqiang
• Boudreault Pierre-Luc T

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/658

  Organoboranes · CPC title