Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12575313-B2
Application number	US-202217585039-A
Country	US
Kind code	B2
Filing date	Jan 26, 2022
Priority date	Mar 31, 2017
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

A compound having a first ligand LA having the Formula: Formula I is disclosed, wherein rings A is a 5- or 6-membered carbocyclic or heterocyclic ring; wherein RA and RB each independently represent mono to the possible maximum number of substitution, or no substitution;wherein Z1 is carbon or nitrogen;wherein each RA and RB is 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;wherein any two substituents are optionally joined or fused into a ring;wherein X1 to X4 each independently represent a carbon or nitrogen;wherein at least one of X1 to X4 is nitrogen;wherein the ligand LA is coordinated to a metal M;wherein the metal M can be coordinated to other ligands; andwherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

First claim

The invention claimed is:

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

wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein R A and R B each independently represent mono to the maximum possible number of substitution, or no substitution;
wherein Z 1 is carbon or nitrogen;
wherein each R A and R B is 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;
wherein if ring A is pyridine and Z 1 is N, then each R A is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R B at X 5 is not aryl or heteroaryl;
wherein any two substituents are optionally joined or fused into a ring;
wherein X 1 to X 6 each independently represent a carbon or nitrogen;
wherein at least one of X 1 to X 6 is nitrogen;
wherein the ligand L A is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

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 M is Ir or Pt.

4 . The compound of claim 1 , wherein one of X 1 to X 4 is nitrogen, and the remaining X 1 to X 6 are carbon.

5 . The compound of claim 1 , wherein two of X 1 to X 4 are nitrogen, and the remaining X 1 to X 6 are carbon.

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

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

wherein R C is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

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

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

10 . The compound of claim 9 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , and Ir(L A ) 2 (L B ); and
wherein L B is different from L A .

11 . The compound of claim 9 , wherein the compound has a formula of Pt(L A )(L B ); and wherein L A and L B can be same or different.

12 . The compound of claim 9 , 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 substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

13 . The compound of claim 8 , wherein the compound is the Compound Ax having the formula Ir(L Ai ) 2 (L Cj );
wherein x=17i+j−17; i is an integer from 1 to 61, and j is an integer from 1 to 17; and wherein L C is selected from the group consisting of:

14 . The compound of claim 8 , wherein the compound is the Compound By having the formula Ir(L Ai )(L Bk ) 2 ;
wherein y=300i+k−300; i is an integer from 1 to 61, and k is an integer from 1 to 300; and wherein L B is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Dyatkin Alexey Borisovich
• Ji Zhiqiang
• Yeager Walter
• Barron Edward

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K50/12

  comprising dopants · CPC title