Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12250875-B2
Application number	US-202318504375-A
Country	US
Kind code	B2
Filing date	Nov 8, 2023
Priority date	Aug 15, 2019
Publication date	Mar 11, 2025
Grant date	Mar 11, 2025

Abstract

Provided are compounds comprising a ligand L A of Formula I

where the ligand L A is coordinated to Ir.

First claim

What is claimed is:

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

wherein:
A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 3 and Z 2 are each independently C or N;
K 3 and Ware each independently a direct bond, O, or S;
X 1 , X 2 , and X 3 are each independently C or N, at least one of X′, X 2 , and X 3 is C;
X is O or NR′;
R A and R B each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
each of R, R′, R A , and R B 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
two adjacent groups can be joined or fused to form a ring wherever chemically feasible,

wherein the ligand L A is complexed to a metal M to form a chelate ring as indicated by the two dotted lines;
the metal M can be coordinated to other ligands;
the metal M is Ir; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

2. The compound of claim 1 , wherein each R, R′, R A and R B are independently 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 Z 1 is N, and Z 2 is C.

4. The compound of claim 1 , wherein Z 1 is C, and Z 2 is N.

5. The compound of claim 1 , wherein X 1 -X 3 are all C.

6. The compound of claim 1 , wherein ring A is pyridine, pyrimidine, pyrazine, imidazole, pyrazole, oxazole, thiazole, or imidazole derived carbene.

7. The compound of claim 1 , wherein X is NR′.

8. The compound of claim 7 , wherein R′ and R can be joined to form a ring wherever chemically feasible.

9. The compound of claim 1 , wherein Z 2 and X 1 -X 3 are all C.

10. The compound of claim 1 , wherein each of K 3 and K 4 is a direct bond.

11. The compound of claim 1 , wherein one of K 3 and K 4 is O.

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

wherein:
R G for each occurrence represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and
each of R″ and R G 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
two adjacent R G groups can be joined together to form a ring wherever chemically feasible.

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

Ligand naming convention
Structure

L A 1-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A 1-(1)(1)(1)(1) to L A 1-(55)(55)(55)(55) having the structure

wherein Rj = Bj, Rk = Bk, Rp = Bp, and Rz = Bz, and

L A 2-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A 2-(1)(1)(1) to L A 2-(55)(55)(55) having the structure

wherein Rj = Bj, Rk = Bk, and Rp = Bp, and

L A 3-(j)(z), wherein each of j, and z is independently an integer from 1 to 55, wherein L A 3-(1)(1) to L A 3-(55)(55) having the structure

wherein Rj = Bj, and Rz = Bz, and

L A 4-(j), wherein j is an integer from 1 to 55, wherein L A 4-(1) to L A 4-(55) having the structure

wherein Rj = Bj, and

L A 5-(j)(k), wherein each of j, and k is independently an integer from 1 to 55, wherein L A 5-(1)(1) to L A 5-(55)(55) having the structure

wherein Rj = Bj, and Rk = Bk, and

L A 6-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A 6-(1)(1)(1)(1) to L A 6-(55)(55)(55)(55) having the structure

wherein Rj = Bj, Rk = Bk, Rp = Bp, and Rz = Bz, and

L A 7-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A 7-(1)(1)(1) to L A 7-(55)(55)(55) having the structure

wherein Rj = Bj, Rk = Bk, and Rp = Bp, and

L A 8-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A 8-(1)(1)(1) to L A 8-(55)(55)(55) having the structure

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Fitzgerald George
• Fleetham Tyler
• Wolohan Peter
• Macor Joseph A
• Macinnis Morgan C
• Palmer Wystan Neil
• Szigethy Geza
• Horwitz Noah

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/624

  containing six or more rings · CPC title

• H10K85/626

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

• H10K85/40

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

• H10K85/622

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