Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11515493-B2
Application number	US-201816216352-A
Country	US
Kind code	B2
Filing date	Dec 11, 2018
Priority date	Jan 11, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

Novel organic metal complexes containing fused isoquinoline type ligands useful as emitters for near infrared OLED devices are disclosed. Such a compound has a first ligand L A having the Formula:

First claim

We claim:

1. A compound comprising a first ligand L A having the Formula:

wherein ring A is a 5- or 6-membered aromatic ring;
wherein X 1 -X 8 are each independently selected from the group consisting of C and N;
wherein R A , R B , R C , and R D represent mono to a maximum possible number of substitutions, or no substitution;
wherein R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of 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 substituents may be joined or fused together to form a ring;
wherein L A is complexed to a metal M;
wherein M is optionally coordinated to other ligands;
wherein M is selected from the group consisting of Ir, Rh, Re, Os, Pt, Au, and Cu;
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and with a proviso that the following compound is excluded:

2. The compound of claim 1 , wherein R A , R B , R C , and R D 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 Ir or Pt.

4. The compound of claim 1 , wherein X 1 -X 8 are each C.

5. The compound of claim 1 , wherein at least one of X 5 -X 8 is N.

6. The compound of claim 1 , wherein ring A is a fused benzene ring.

7. The compound of claim 1 , wherein two adjacent R D forms a fused aromatic ring.

8. The compound of claim 1 , wherein R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof.

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

wherein R 1 and R 2 each represent mono to a maximum possible number of substitutions, or no substitution;
wherein R 1 and R 2 are each independently a hydrogen or a substituent selected from the group consisting of 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; and
wherein any two substituents can be joined or fused together to form a ring.

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

11. The compound of claim 10 , wherein the compound is the Compound Ax having the formula Ir(L Ai ) 3 , Compound By having the formula Ir(L Ai )(L Bk ) 2 , or Compound Cz having the formula Ir(L Ai ) 2 (L Cj );
wherein x=i, y=460i+k−460, and z=25i+j−25;
wherein i is an integer from 1 to 100, k is an integer from 1 to 460, and j is an integer from 1 to 25;
wherein L Bk has the following structures:

Assignees

• Universal Display Corp

Inventors

• Thompson Nicholas J
• Ma Bin
• Joseph Scott
• Boudreault Pierre-Luc T
• Ji Zhiqiang

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07C15/38

  containing four rings · CPC title

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title