Granted Patent B2

US 12,486,288 · App. 17/481,543 · Granted Dec 2, 2025

Inventors: Mark E. Thompson (Anaheim, CA); Peter I. Djurovich (Long Beach, CA)

C07D513/04C07F1/12C07F15/0033H10K85/342H10K85/371H10K85/654H10K50/11H10K2101/10

Abstract

Claims (50)

1 . A compound represented by the following Formula I:

wherein X 1 to X 8 each independently represent N or C;

Y represents O, S, Se, NR, PR, CRR′, or SiRR′;

R A is represented by the following Formula A:

wherein the dashed line represents the bond to one of X 1 to X 8 ;

M is Ag(I), Au(I), or C (I);

ring B is a carbene coordinated to the metal M;

n and m are each 0 or 1, wherein n+m=1;

each R 1 and R 2 independently represents mono to the maximum allowable substitution; and

each occurrence of R, R′, R B , R 1 , and R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitro, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R, R′, R 1 , R 2 , 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 Y is S or O.

3 . The compound of claim 1 , wherein Y is NR.

4 . The compound of claim 1 , wherein wherein one of the following conditions is true:

(i) n is 1, m is 0, and at least one R 1 represents a substituent selected from the group consisting of deuterium, alkyl, aryl, amino, sulfanyl, hydroxyl, alkoxyl, and combinations thereof; or

(ii) n is 0, m is 1, and at least one R 2 represents a substituent selected from the group consisting of deuterium, alkyl, aryl, amino, sulfanyl, hydroxyl, alkoxyl, and combinations thereof.

5 . The compound of claim 1 , wherein ring B is represented by one of Formulae (Ba), Formula (Bb), or Formula (Bc):

wherein

the dashed line represents coordination to M;

each X 21 to X 24 independently represents NR, CRR′, C═O, C═S, O, or S;

each X 25 and X 26 independently represents NR, CRR′, O, or S;

each X 27 to X 30 independently represents N or C;

X A represents CRR′;

m represents 0 or 1;

the dashed line inside the ring represents zero or one double-bond;

R 3 represents mono to the maximum allowable substitution;

each occurrence of R, R′, and R 3 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, R′, and R 3 are optionally joined or fused together to form a ring which is optionally substituted.

6 . The compound of claim 1 , wherein the compound is represented by the following Formula II:

wherein X 1 to X 8 each independently represent N or C;

Y represents O, S, Se, NR, PR, CRR′, or SiRR′;

M is a transition metal selected from the group consisting of Ag(I), Au(I), and Cu(I);

Ring B is coordinated to M and is not covalently bound to any of X 1 to X 8 ;

n and m are each 0 or 1, wherein n+m=1;

each R 1 and R 2 independently represents mono to the maximum allowable substitution; and

each occurrence of R, R′R B , R 1 and R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, N-heterocyclic carbenyl; nitro, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R, R′, R B , R 1 , and R 2 are optionally joined or fused together to form a ring which is optionally substituted.

7 . The compound of claim 6 , wherein the compound is represented by the following structure:

8 . An organic electroluminescent device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound represented by the following Formula I:

wherein X 1 to X 8 each independently represent N or C;

Y represents O, S, Se, NR, PR, CRR′, or SiRR′;

R A is represented by the following Formula A:

wherein the dashed line represents the bond to one of X 1 to X 8 ;

M is Ag(I), Au(I), or Cu(I);

ring B is a carbene coordinated to the metal M;

n and m are each 0 or 1, wherein n+m=1;

each R 1 and R 2 independently represents mono to the maximum allowable substitution; and

each occurrence of R, R′, R B , R 1 , and R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitro, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R, R′, R 1 , R 2 , R A , and R B are optionally joined or fused together to form a ring which is optionally substituted.

9 . A formulation comprising the compound of claim 1 .

Assignments (1)

Continuity (2)

References Cited (203)