Fast phosphors utilizing HP2H ligands

Patent metadata

Field	Value
Publication number	US-12486288-B2
Application number	US-202117481543-A
Country	US
Kind code	B2
Filing date	Sep 22, 2021
Priority date	Oct 12, 2020
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

A compound is described as having a triplet excited state and a singlet excited state; wherein the triplet excited state comprises a lowest energy triplet sublevel, a middle energy triplet sublevel, and a highest energy triplet sublevel; and wherein an energy separation between the highest energy triplet sublevel and the lowest energy triplet sublevel (ZFS) is greater than an energy separation between the singlet excited state and a the lowest energy triplet sublevel. Also described is a compound represented by the following Formula I. 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 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 .

Assignees

• Univ Southern California

Inventors

• Thompson Mark E
• Djurovich Peter I

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/654

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

• H10K85/371

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

• H10K85/342

  comprising iridium · CPC title