Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12520715-B2
Application number	US-202217811422-A
Country	US
Kind code	B2
Filing date	Jul 8, 2022
Priority date	Jul 16, 2021
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

The present disclosure provides coinage metal 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 represented by the following Formula I:

wherein M 1 is selected from the group consisting of Au(I), Ag(I), and Cu(I);
L is a carbene coordinated to the metal M 1 ;
Z is a monoanionic ligand;
E 1 is an electron accepting group;
n is an integer from 1 to the maximum allowable substitution on L, wherein when n is greater than 1, each E 1 may be the same or different;
E 1 , L, 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 E 1 is selected from the group consisting of a nitrogen-containing heterocyclic ring and a carbocyclic aromatic ring optionally having at least one electron-withdrawing substituent.

3 . The compound of claim 1 , wherein E 1 is a nitrogen-containing heterocyclic ring selected from the group consisting of aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-benzofuran, aza-benzothiophene, aza-benzoselenophene, aza-carbazole, aza-indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, aza-xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenophenodipyridine, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof; wherein E 1 is optionally further substituted.

4 . The compound of claim 1 , wherein E 1 is a nitrogen-containing heterocyclic ring fused to the carbene L.

5 . The compound of claim 1 , wherein E 1 is an aromatic ring having at least one electron-withdrawing substituent selected from the group consisting of halogen, pseudohalogen, haloalkyl, halocycloalkyl, heteroalkyl, amide, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitro, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein E 1 is optionally further substituted.

6 . The compound of claim 1 , wherein L 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 at least one substituent R 1 and R 2 comprises an electron accepting group;
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, CR 1 R 2 , SiR 1 , SiR 1 R 2 , 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 , N, P, B, 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 at least one substituent R 1 and R 2 comprises an electron accepting group;
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 at least one substituent R 1 and R 2 comprises an electron accepting group;
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 at least one substituent R 1 and R 2 comprises an electron accepting group; 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 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;
wherein at least one substituent R 1 and R 2 comprises an

Assignees

• Univ Southern California

Inventors

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

Classifications

• C09K2211/188

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F1/08 Primary

  Copper compounds · CPC title

• C07F1/005 Primary

  without C-Metal linkages · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title