Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12317745-B2
Application number	US-201715792893-A
Country	US
Kind code	B2
Filing date	Oct 25, 2017
Priority date	Nov 9, 2016
Publication date	May 27, 2025
Grant date	May 27, 2025

Abstract

This present invention includes novel ligands for metal complexes, which include three fused cycles or heterocycles. The first ring may be either a pyridine or a pyrimidine ring, which coordinates with the iridium metal. The second ring may be a six-membered ring, which may or may not contain nitrogen atoms. The third ring may be either a five or six membered ring. The combination of these aromatic rings provides near infrared or infrared emission in PHOLEDs devices. The bottom ring of the ligand is an alkylated cycle or heterocycle which provides a good efficiency and emission line shape.

First claim

We claim:

1. A compound comprising a ligand L A , having a structure of

wherein:
the combination of ring A and R 1 has a structure selected from the group consisting of:

wherein each bond ------- is linked to the azaphenanthrene and each bond ″″″″″″ is linked to the metal;
wherein L A is coordinated to an Ir atom;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein Ir is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein the compound has a formula of M(L A ) n (L B ) m-n ;
wherein M is Ir;
L B is a bidentate ligand; and
wherein m is 3, and n is 1, 2, or 3.

3. The compound of claim 2 , wherein L B is selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
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′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, 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 substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or to form a multidentate ligand.

4. The compound of claim 1 , wherein the compound has the formula Ir(L A ) 2 (L Cj ); and
wherein L C is selected from the group consisting of:

5. The compound of claim 4 , wherein no two R 1 are joined to form a ring, the R 1 para to the Ir is not hydrogen, the R 1 ortho to the Ir is not hydrogen; and the remaining R 1 are hydrogen.

6. The compound of claim 4 , wherein the combination of ring A and R 1 have a structure selected from the group consisting of:

7. The compound of claim 4 , wherein the combination of ring A and R 1 have a structure of

8. The compound of claim 1 , wherein the compound has the formula Ir(L A )(L Bk ) 2 ; and
wherein L B is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Alleyne Bert

Classifications

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• H10K99/00

  Subject matter not provided for in other groups of this subclass · CPC title

• H10K59/00

  Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00 · CPC title

• C07D251/42

  One nitrogen atom · CPC title

• C07D239/70

  condensed with carbocyclic rings or ring systems · CPC title