Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12369487-B2
Application number	US-202117378350-A
Country	US
Kind code	B2
Filing date	Jul 16, 2021
Priority date	Aug 5, 2020
Publication date	Jul 22, 2025
Grant date	Jul 22, 2025

Abstract

A compound comprising a ligand L A of Formula I,

where G has a structure of

is disclosed. In ligand L A , Ring C is a 5-membered or 6-membered ring; K is a direct bond, O, or S; when K is O or S, X 6 is C; each of R A , R B , and R C is H or a substituent, and can be joined together to form a ring; each of X 1 to X 6 is independently C or N; X 1 is C if it is connected to ring C; the R B substituents of at least two adjacent ones of X 2 to X 5 are joined to form a ring; and the ligand L A is complexed to Ir through the two indicated dash lines to form a 5-membered chelate ring. Organic light emitting devices, consumer products, formulations, and chemical structures containing the compounds are also disclosed.

First claim

What is claimed is:

1. A compound comprising a ligand L A of Formula I

wherein:
G has a structure of

Ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
K is selected from the group consisting of a direct bond, O, and S;
when K is O or S, X 6 is C;
R A , R B , and R C each independently represent mono to a maximum allowable substitution, or no substitution;
each of R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
each of X 1 to X 5 is independently C or N;
X 6 is C;
X 1 is C if it is connected to ring C;
the maximum number of N atoms that can be bonded together in Ring B is two;
at least two adjacent X 2 to X 5 are carbon atoms, and the R B substituents that are attached to the carbon atoms are joined to form a fused 5-membered or 6-membered carbocyclic or heterocyclic ring;
the ligand L A is complexed to Ir through the two indicated dash lines to form a 5-membered chelate ring;
Ir can be coordinated to other ligands;
the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
any two substituents can be joined or fused to form a ring.

2. The compound of claim 1 , wherein each R A , R B , and R C 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 X 1 is N, one of X 2 to X 5 is N, or both.

4. The compound of claim 1 , wherein K is O or S.

5. The compound of claim 1 , wherein two R B substituents are joined to form a fused 5-membered aromatic ring or a fused 6-membered aromatic ring.

6. The compound of claim 1 , wherein K is a direct bond and the ligand L A has a structure selected from the group consisting of:

and
wherein:
X is selected from the group consisting of O, S, CR′R″, and NR′;
Y is selected from the group consisting of CR′ and N;
each R 1 , R′, and R″ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and
G is a 5-membered or 6-membered aryl or heteroaryl ring, which can be further substituted.

7. The compound of claim 6 , wherein G is selected from the group consisting of phenyl, pyridine, naphthalene, quinoline, isoquinoline, thiophene, furan, benzothiophene, benzofuran, carbazole, dibenzofuran, and dibenzothiophene, which can be further substituted.

8. The compound of claim 1 , wherein ligand L A is selected from the group consisting of L A1-1 to L A780-80 , where each L Ai-m is defined as follows, where i is an integer from 1 to 780 and m is an integer from 1 to 80:
wherein L Ai-1 to L Ai-80 have the following structures:

where for each of LA1-m to LA780-m, R E and G are defined in the following list:

Ligand
R E
G

LA1-m
R 1
G 1

LA2-m
R 2
G 1

LA3-m
R 3
G 1

LA4-m
R 4
G 1

LA5-m
R 5
G 1

LA6-m
R 6
G 1

LA7-m
R 7
G 1

LA8-m
R 8
G 1

LA9-m
R 9
G 1

LA10-m
R 10
G 1

LA11-m
R 11
G 1

LA12-m
R 12
G 1

LA13-m
R 13
G 1

LA14-m
R 14
G 1

LA15-m
R 15
G 1

LA16-m
R 16
G 1

LA17-m
R 17
G 1

LA1

Assignees

• Universal Display Corp

Inventors

• Lu Tongxiang
• Ji Zhiqiang
• Fitzgerald George
• Boudreault Pierre-Luc T
• Tsai Jui-Yi

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1051

  with sulfur · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title