Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11239434-B2
Application number	US-201916243655-A
Country	US
Kind code	B2
Filing date	Jan 9, 2019
Priority date	Feb 9, 2018
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

A compound including a first ligand L A of Formula I

is disclosed.

First claim

We claim:

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

wherein,
Ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 , Z 2 , and Z 3 are each independently selected from the group comprising C and N;
Y is selected from the group consisting of O, S, Se, NR 3 , CRR′, SiRR′, GeRR′, and a single bond;
Y is not CRR′ when Z 1 , Z 2 , and Z 3 are C;
if Y is a single bond, then Z 3 is C and Ring A is not pyridine or if Y is a single bond and Ring A is pyridine, then at least one of Z 1 , Z 2 , or Z 3 is N;
a metal M forms a direct bond to Ring A or Ring B;
M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au;
R A and R B each independently represents mono to a maximum possible number of substitutions, or no substitution;
R A , R B , R 1 , R 2 , R 3 , R, and R′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, 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;
one of R A or R B is a 5-membered or 6-membered aromatic ring that is bonded to M;
the ligand L A is optionally linked with other ligands to form a ligand having a denticity of tridentate to a maximum possible denticity to which M can coordinate;
any two substituents may be joined or fused together to form a ring, provided that R 1 and R 2 are not joined to form a 6-membered aromatic ring when Y is a single bond; and
M is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein R A , R B , R 1 , R 2 , R 3 , R, and R′ are each 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 M is selected from the group consisting of Ir and Pt.

4. The compound of claim 1 , wherein Y is a single bond or selected from the group consisting of O, S, and NR 3 .

5. The compound of claim 1 , wherein one of R A or R B comprises a benzene ring, that is bonded to M.

6. The compound of claim 1 , wherein one of R A or R B comprises a pyridine ring, that is bonded to M.

7. The compound of claim 1 , wherein one of Z 1 , Z 2 , or Z 3 is N and forms a dative bond to M, and the remaining two of Z 1 , Z 2 , and Z 3 are C.

8. The compound of claim 1 , wherein Ring A contains an N atom that forms a dative bond to M.

9. The compound of claim 1 , wherein Ring A is a 5-membered aromatic ring or a 6-membered aromatic ring.

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

wherein,
R C represents mono to a maximum possible number of substitutions, or no substitution; and
R C and R 4 are each 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.

11. The compound of claim 1 , wherein L A is selected from the group consisting of L A1 through L A294 having structures of Formula I

wherein R 1 , R 2 , R 5 , R 6 , and R 7 are defined as follows:

Ligand
R 1
R 2
R 7
R 6
R 5

L A1
H
H
H
H
H

L A2
R B1
H
H
H
H

L A3
R B1
R B1
H
H
H

L A4
R B1
R B1
R B1
H
H

L A5
R B1
H
R B1
H
H

L A6
H
H
R B1
H
H

L A7
H
H
H
R B1
R B1

L A8
R B1
H
H
R B1
R B1

L A9
R B1
R B1
H
R B1
R B1

L A10
R B1
R B1
R B1
R B1
R B1

L A11
R B1
H
R B1
R B1
R B1

L A12
H
H
R B1
R B1
R B1

L A13
H
H
H
R B44
R B44

L A14
R B1
H
H
R B44
R B44

L A15
R B1
R B1
H

Assignees

• Universal Display Corp

Inventors

• Joseph Scott
• Boudreault Pierre-Luc T

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/185

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

• H01L2251/552

  Electricity · mapped topic