Tandem carbene phosphors

Patent metadata

Field	Value
Publication number	US-12331064-B2
Application number	US-202117528258-A
Country	US
Kind code	B2
Filing date	Nov 17, 2021
Priority date	Dec 9, 2020
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

Tandem carbene phosphors such as those of Formula I 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 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.

2. The compound of claim 1 , wherein Z is selected from the group consisting of an alkyl anion, aryl anion, halide, trifluoromethylsulfonate, amide, alkoxide, sulfide, or phosphide.

3. The compound of claim 1 , 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.

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

wherein the dashed line indicates the bond to M 2 .

5. The compound of claim 1 , 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, 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.

6. The compound of claim 1 , wherein E 1 is represented by one of the following structures:

wherein each X 1 and X 2 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 3 and X 4 independ

Assignees

• Univ Southern California

Inventors

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

Classifications

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/371

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

• H10K2101/10

  Triplet emission · CPC title

• C07F1/00 Primary

  Compounds containing elements of Groups 1 or 11 of the Periodic Table · CPC title