Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12325718-B2
Application number	US-202217749733-A
Country	US
Kind code	B2
Filing date	May 20, 2022
Priority date	Apr 13, 2018
Publication date	Jun 10, 2025
Grant date	Jun 10, 2025

Abstract

A compound having a first ligand L A of Formula I

is disclosed, where Z 1 to Z 4 are each independently C or N; at least one of Z 1 to Z 4 is N; and ring A is a structure of Formula II

First claim

We claim:

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

wherein Z 1 to Z 4 are each independently C or N;
two of Z 1 to Z 4 are N, and the remainder are C;
wherein ring A is Formula II

wherein each R A and R 4 independently represents mono substitution to a maximum possible number of substitutions, or no substitution;
wherein Z 5 to Z 8 are each independently C or N;
wherein R 3 is a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, aryl, and heteroaryl;
wherein each R A and R 4 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two substituents can be joined or fused together to form a ring;
wherein R 3 and ring A do not have identical formulas;
wherein the ligand L A is complexed to a metal M;
wherein M is optionally coordinated to other ligands;
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein if Z 1 is N, the compound is homoleptic, or M is complexed to at least one substituted or unsubstituted acetylacetonate ligand.

2. The compound of claim 1 , wherein each R A and R 4 is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein R A represents a fused ring.

4. The compound of claim 1 , wherein Z 6 is C and is attached to an alkyl group.

5. The compound of claim 1 , wherein R 3 is a 5-membered heteroaryl group or a 6-membered aryl or heteroaryl group.

6. The compound of claim 1 , wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au.

7. The compound of claim 1 , wherein the compound further comprises a substituted or unsubstituted acetylacetonate ligand.

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

wherein R 1 and R 2 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

9. The compound of claim 1 , wherein the first ligand L A is selected from the group consisting of
ligands L XII-Ai that are based on a structure of Formula XII

ligands L XIV-Ai that are based on a structure of Formula XIV

ligands L XVI-Ai that are based on a structure of Formula XVI

and
ligands L XVIII-Ai that are based on a structure of Formula XVIII

wherein i is an integer from 1 to 840 and for each i, R 1 , R 2 , R 3 , and R 4 in Formula XII, Formula XIV, Formula XVI, and Formula XVIII are defined as follows:

i
R 1
R 2
R 3
R 4
i
R 1
R 2
R 3
R 4

1.
R B1
R B1
R B3
H
421.
R B1
R B6
R B3
H

2.
R B1
R B1
R B6
H
422.
R B1
R B6
R B6
H

3.
R B1
R B1
R B7
H
423.
R B1
R B6
R B7
H

4.
R B1
R B1
R B12
H
424.
R B1
R B6
R B12
H

5.
R B1
R B1
R B20
H
425.
R B1
R B6
R B20
H

6.
R B1
R B1
R B25
H
426.
R B1
R B6
R B25
H

7.
R B1
R B1
RB1
H
427.
R B1
R B6
RB1
H

8.
R B1
R B1
R A37
H
428.
R B1
R B6
R A37
H

9.
R B1
R B1
R A43
H
429.
R B1
R B6
R A43
H

10.
R B1

Assignees

• Universal Display Corp

Inventors

• Joseph Scott
• Ma Bin
• Boudreault Pierre-Luc T

Classifications

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title