Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9859510-B2
Application number	US-201615076022-A
Country	US
Kind code	B2
Filing date	Mar 21, 2016
Priority date	May 15, 2015
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

Novel ligands for metal complexes containing five-membered ring fused on pyridine or pyrimidine ring combined with partially fluorinated side chains exhibiting improved external quantum efficiency and lifetime are disclosed.

First claim

We claim:

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

wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R is fused to ring B and has a structure of Formula II:

wherein the wave lines indicate bonds to ring B;
wherein R 1 represents mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono or di substitution, or no substitution;
wherein X 1 , X 2 , X 3 , and X 4 are each independently carbon or nitrogen;
wherein at least two adjacent of X 1 , X 2 , X 3 , and X 4 are carbon and fuse to R;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R 1 , R 2 , R 3 , R 4 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents are optionally joined to form into a ring;
wherein at least one of R 3 and R 4 comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
wherein the ligand L A is coordinated to a metal M;
wherein the ligand 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 M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

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

4. The compound of claim 1 , wherein the ligand L A is:

5. The compound of claim 1 , wherein at least one of R 3 and R 4 is a chemical group selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof.

6. The compound of claim 1 , wherein R 3 and R 4 are not hydrogen.

7. The compound of claim 1 , wherein at least one of X 1 , X 2 , X 3 , and X 4 is nitrogen.

8. The compound of claim 1 , wherein at least one of R 3 and R 4 is selected from the group consisting of:

9. The compound of claim 1 , wherein R 3 and R 4 are joined to form a ring structure selected from the group consisting of:

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

11. The compound of claim 8 , wherein the ligand L A is selected from the group consisting of L A1 through L A750 defined as follows:
L A1 through L A375 are based on a structure of Formula IV,

in which R 3 , R 4 , and X are defined as:

Ligand
R 3
R 4
X

L A1
H
R A2
O

L A2
R A2
R A2
O

L A3
R A3
R A2
O

L A4
R A14
R A2
O

L A5
R A22
R A2
O

L A6
R A28
R A2
O

L A7
H
R A3
O

L A8
R A2
R A3
O

L A9
R A3
R A3
O

L A10
R A14
R A3
O

L A11
R A22
R A3
O

L A12
R A28
R A3
O

L A13
H
R A14
O

L A14
R A2
R A14
O

L A15
R A3
R A14
O

L A16
R A14
R A14
O

L A17
R A22
R A14
O

L A18
R A28
R A14
O

L A19
H
R A22
O

L A20
R A2
R A22
O

L A21

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Wendt Harvey
• Xia Chuanjun

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

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

• C07D491/048 Primary

  the oxygen-containing ring being five-membered · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title