Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2025051366-A1
Application number	US-202318359080-A
Country	US
Kind code	A1
Filing date	Jul 26, 2023
Priority date	Jul 26, 2022
Publication date	Feb 13, 2025
Grant date	—

Abstract

The present disclosure provides amide M carbene emitters of Formula (I); organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer, disposed between the anode and the cathode, comprising a compound of Formula (I); and consumer products comprising an OLED comprising a compound of Formula (I):

First claim

We claim:

1 . A compound of formula (I):

wherein
M is a metal;
ring B is a carbene ligand;
R represents mono to the maximum allowable substitution;
each R is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted;
ring A is an amide ligand selected from the group consisting of formula (A-1) and formula (A-2);

wherein, in formula (A-1),
the dashed line represents coordination to M;
each X 3 , X 6 , X 7 , and X 8 independently represents N or C;
R A represents mono to the maximum allowable substitution;
wherein any two adjacent groups R A may optionally together form a fused ring having the following formula:

wherein each X 1 , X 2 , X 3 , and X 4 independently represents N or C;
n is 0 or 1; wherein when n is 0, then X 3 binds directly to formula (A-1);
R B represents mono to the maximum allowable substitution;
each occurrence of R A and R B is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein any two R B are optionally joined or fused together to form a ring which is optionally substituted;

wherein, in formula (A-2);
each X 11 to X 18 independently represents N or C;
R A and R B each represent mono to the maximum allowable substitution; and
each occurrence of R A and R B is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein any two adjacent R A and R B are optionally joined or fused together to form a ring which is optionally substituted.

2 . The compound of claim 1 , wherein M is selected from the group consisting of Cu, Ag, and Au.

3 . The compound of claim 1 , wherein ring A is represented by formula (A-2).

4 . The compound of claim 1 , wherein ring A is represented by one of the following structures:

5 . The compound of claim 1 , wherein ring B is selected from the group consisting of Formula A, Formula B, Formula C, Formula D, Formula E, and Formula F:

wherein
each X 1 to X 4 independently represents NR 1 , CR 1 R 2 , C═O, C═S, O, or S; and
each occurrence of R 1 and R 2 is 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
wherein any two adjacent R 1 and R 2 are optionally joined or fused together to form a ring which is optionally substituted.

wherein each X 1 and X 4 independently represents N, NR 1 , CR 1 , CR 1 R 2 , SiR 1 , SiR 1 R 2 , PR 1 , B, BR 1 , BR 1 R 2 , O, or S; and
each X 2 and X 3 independently represents CR 1 , CR 1 R 2 , SiR 1 , SiR 1 R 2 , N, NR 1 , P, PR 1 , B, BR 1 , O, or S;
each occurrence of R 1 and R 2 is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
wherein any two adjacent R 1 and R 2 are optionally joined or fused together to form a ring which is optionally substituted; and
the dashed line inside the five-member ring represents zero or one double-bond.

wherein each X 1 and X 2 independently represents NR 1 , CR 1 R 2 , O, or S;
each occurrence of R 1 and R 2 is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; and
wherein any two adjacent R 1 and R 2 are optionally joined or fused together to form a ring which is optionally substituted.

wherein
each X 1 to X 5 independently represents N, P, NR 1 , PR 1 , B, BR 1 , CR 1 , SiR 1 , CR 1 R 2 , SiR 1 R 2 , C═O, C═S, O, or S;
n is 0 or 1;
each occurrence of R 1 and R 2 is independently 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, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
wherein any two adjacent R 1 and R 2 are optionally joined or fused together to form a ring which is optionally substituted;

wherein
each X 1 and X 4 independently represents NR 1 , CR 1 , SiR 1 , CR 1 R 2 , SiR 1 R 2 , PR 1 , BR 1 , C═O, C═S, O, or S;
each X 2 and X 3 is independently present or absent, and if present, independently represents H, NR 1 R 2 , CR 1 , CR 1 R 2 , C═O, C═S, O, or S;
each occurrence of R 1 and R 2 is independently hydrogen or a substituent selected from the

Assignees

• Univ Southern California

Inventors

• Djurovich Peter I
• Muniz Collin
• Razgoniaev Anton
• Schaab Jonas
• Thompson Mark E

Classifications

• H10K85/371

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• C07F1/08

  Copper compounds · CPC title