Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11239433-B2
Application number	US-201816038878-A
Country	US
Kind code	B2
Filing date	Jul 18, 2018
Priority date	Jul 26, 2017
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

A compound comprising a ligand L A having the formula:

is disclosed.

Such a compound is suitable for use an emitter in organic light emitting devices.

First claim

We claim:

1. A compound comprising a first ligand L A of

wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein X is NR, O, or S;
wherein R A and R B each represents mono to a maximum possible number of substitutions, or no substitution;

wherein R A and R B are each independently selected from the group consisting of hydrogen, 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 R is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein any adjacent substitutions in R, R A and R B can be joined or fused into a ring;
wherein Z 1 is an anionic coordinating atom selected from the group consisting of C and N;
wherein the ligand L A is coordinated to Ir or Pt;
wherein L A is a bidentate ligand when it is coordinated to Ir;
wherein Ir or Pt can be coordinated to other ligands.

2. The compound of claim 1 , wherein R A and R B are each independently selected from the group consisting of hydrogen, 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 ring A is a 6-membered aromatic ring.

4. The compound of claim 1 , wherein ring A is a 5-membered aromatic ring.

5. The compound of claim 1 , wherein A is benzene.

6. The compound of claim 1 , wherein the anionic coordinating carbon is an sp2 carbon atom of a 5- or 6-membered carbocyclic or heterocyclic ring selected from the group consisting of benzene, pyridine, furan, thiophene, and pyrrole; or
wherein the anionic coordinating nitrogen is an sp2 nitrogen atom of an N-heterocyclic ring selected from the group consisting of imidazole, benzoimidazole, pyrazole, pyrrole, and triazole.

7. The compound of claim 1 , wherein R and an adjacent R B are joined together to form a 5-membered or 6-membered heterocyclic ring.

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

wherein R 1 , R 3 and R 4 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and
wherein R 3 and R 4 can be joined to one another to form a ring.

9. The compound of claim 1 , wherein the first ligand L A has Formula II

wherein A 1 , A 2 , A 3 , and A are each independently C or N;
wherein at least two adjacent ones among A 1 , A 2 , A 3 , and A 4 are C and are fused to a structure of Formula III

wherein Y is NR′, O, or S;
wherein A 5 , A 6 , A 7 , and A 8 are each independently C or N;
wherein R C has the same definition as R A ; and
wherein R′ has the same definition as R.

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

Assignees

• Universal Display Corp

Inventors

• Macinnis Morgan C
• Drennan Diana
• Lu Tongxiang
• Silverstein Daniel W
• Chen Hsiao-Fan
• Fitzgerald George
• Brooks Jason
• Lahti Paul M

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• C09K2211/185

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