Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2018375035-A1
Application number	US-201816009455-A
Country	US
Kind code	A1
Filing date	Jun 15, 2018
Priority date	Jun 23, 2017
Publication date	Dec 27, 2018
Grant date	—

Abstract

A compound comprising a first ligand L A of Formula I

is provided. In Formula I, A is a 5- or 6-membered aryl or heteroaryl ring; each of Z 1 -Z 11 is either C or N; each of Y 1 -Y 4 is selected from a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′; at least one of Y 1 and Y 2 is not a direct bond; at least one of Y 3 and Y 4 is not a direct bond; each R A , R B , R C , R, and R′ is independently hydrogen or a variety of substituents; any two adjacent substitutions in R A , R B and R C can be joined or fused into a ring; ligand L A is coordinated to a metal M; L A is optionally linked with other ligands; and M is optionally coordinated to other ligands. Organic light emitting devices and consumer products containing the compounds are also disclosed.

First claim

We claim:

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

wherein A is a 5- or 6-membered aryl or heteroaryl ring;
wherein R A , R B , and R C each represent mono to a maximum possible number of substitutions, or no substitution;
wherein Z 1 -Z 11 are each independently selected from the group consisting of C and N;
wherein Y 1 , Y 2 , Y 3 , and Y 4 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein at least one of Y 1 and Y 2 is not a direct bond;
wherein at least one of Y 3 and Y 4 is not a direct bond;
wherein R A , R B , R C , R, and R′ 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 any two adjacent substitutions in R A , R B and R C are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

2 . The compound of claim 1 , wherein one of Y 1 and Y 2 is O and the other one of Y 1 and Y 2 is a direct bond, and one of Y 3 and Y 4 is O and the other one of Y 3 and Y 4 is a direct bond, or
wherein one of Y 1 and Y 2 is S and the other one of Y 1 and Y 2 is a direct bond, and one of Y 3 and Y 4 is S and the other one of Y 3 and Y 4 is a direct bond.

3 . The compound of claim 1 , wherein each of Y 1 , Y 2 , Y 3 , and Y 4 is O or each of Y 1 , Y 2 , Y 3 , and Y 4 is S.

4 . The compound of claim 1 , wherein Z 1 is N, Z 2 is C, and Z 3 is C.

5 . The compound of claim 1 , wherein Z 1 is C, Z 2 is N, and Z 3 is C.

6 . The compound of claim 1 , wherein Z 1 is N, Z 2 is C, and Z 3 is N.

7 . The compound of claim 1 , wherein each one of Z 4 through Z 11 is C.

8 . The compound of claim 1 , wherein at least one of Z 4 through Z 11 is N.

9 . The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

10 . The compound of claim 1 , wherein ring A is selected from the group consisting of pyridine, pyrimidine, imidazole, pyrazole, and imidazole derived carbene.

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

wherein each of Z 12 through Z 14 is independently selected from the group consisting of C and N;
wherein R D is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substitutions of R A , R B , R C , and R D are optionally joined or fused into a ring.

12 . The compound of claim 1 , wherein ring A is pyridine, Z 1 is nitrogen, and R A para to Z 1 is not hydrogen or deuterium.

13 . The compound of claim 1 , wherein R A is at least a monosubstitution and at least one of R A substituent is selected from the group consisting of:

14 . The compound of claim 1 , wherein L A is selected from the group consisting of L A1 to L A544 , which are defined as follows:

Ligand L A1 through L A5 , each represented by the formula

wherein in ligand L A1 , Y 1 = O, Y 4 = O;

in ligand L A2 , Y 1 = S, Y 4 = S;

in ligand L A3 , Y 1 = C(CH 3 ) 2 , Y 4 = C(CH 3 ) 2 ;

in ligand L A4 , Y 1 = O, Y 4 = S;

in ligand L A5 , Y 1 = S, Y 4 = O;

Ligand L A6 through L A10 , each represented by the formula

wherein in ligand L A6 , Y 1 = O, Y 4 = O;

in ligand L A7 , Y 1 = S, Y 4 = S;

in ligand L A8 , Y 1 = C(CH 3 ) 2 , Y 4 = C(CH 3 ) 2 ;

in ligand L A9 , Y 1 = O, Y 4 = S;

in ligand L A10 , Y 1 = S, Y 4 = O;

Ligand L A11 through L A15 , each represented by the formula

Assignees

• Universal Display Corp

Inventors

• Ji Zhiqiang
• Dyatkin Alexey Borisovich
• Tsai Jui-Yi

Classifications

• H01L51/0085 Primary

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5016

  Electricity · mapped topic

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title