Tandem-carbene phosphors

Patent metadata

Field	Value
Publication number	US-12342716-B2
Application number	US-202117539382-A
Country	US
Kind code	B2
Filing date	Dec 1, 2021
Priority date	Dec 9, 2020
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

Compounds comprising a first ligand and a second ligand; wherein the first ligand coordinates to a first metal through a first metal-carbene bond; the second ligand coordinates to a second metal through a second metal-carbene bond; the second ligand also coordinates to the first metal; the first ligand can link to the second ligand to form a multidentate ligand; and the first metal and the second metal are each independently selected from the group consisting of Au, Ag, and Cu can act as electron acceptors in tandem to increase the energy separation between the ground and excited state, which is higher than those found in analogous monometallic complexes. These compounds should find application as luminescent materials in organic light emitting diodes (OLEDs).

First claim

We claim:

1. A compound comprising a first ligand and a second ligand;
wherein:
the first ligand coordinates to a first metal through a first metal-carbene bond;
the second ligand coordinates to a second metal through a second metal-carbene bond;
the second ligand also coordinates to the first metal;
the first ligand can link to the second ligand to form a multidentate ligand; and
the first metal and the second metal are each independently selected from the group consisting of Au, Ag, and Cu.

2. The compound of claim 1 , wherein the compound is represented by the following Formula I:

wherein M 1 and M 2 are independently selected from the group consisting of Au(I), Ag(I), and Cu(I);
E 1 is a carbene coordinated to the metal M 1 ;
E 2 is an anionic carbene coordinated to the metal M 1 and the metal M 2 ;
Z is a monoanionic ligand;
E 1 , E 2 , and Z may each be substituted with one or more substituents independently selected from the group consisting of hydrogen, 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 substituents may together join to form a ring; and
E 1 is optionally linked to E 2 though one or more substituents or through one or more fused ring fusions.

3. The compound of claim 2 , wherein Z is selected from the group consisting of an alkyl anion, aryl anion, halide, trifluoromethylsulfonate, amide, alkoxide, sulfide, or phosphide.

4. The compound of claim 2 , wherein Z is represented by one of the following structures:

wherein the dashed line indicates the bond to M 2 ; and
each occurrence Y is selected from the group consisting of N and CR.

5. The compound of claim 2 , wherein Z is represented by one of the following structures:

wherein the dashed line indicates the bond to M 2 .

6. The compound of claim 2 , wherein E 1 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; 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 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 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 occurrence of X 1 to X 8 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 1 or 2;
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, het

Assignees

• Univ Southern California

Inventors

• Li tian-yi
• Djurovich Peter I
• Thompson Mark E

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title