IP Library › Granted Patent US 12,623,919
Granted Patent B2
US 12,623,919 · App. 17/145,668 · Granted May 12, 2026

Organic electroluminescent materials and devices

Inventors: Hsiao-Fan Chen (Lawrence Township, NJ); Peter Wolohan (Princeton Junction, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
C01G55/00H10K85/346H10K85/40H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,623,919
App. No.
17/145,668
Granted
May 12, 2026
Kind
B2
Abstract

Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

Claims (247)

1 . A compound comprising a ligand L A of

wherein:

ligand L A is coordinated to a metal M selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;

Z 1 -Z 2 are each independently C or N with one being N and the other C;

ring B is a 5-membered or 6-membered aromatic ring;

X is C or N;

each of X 1 —X 7 is independently C or N;

if metal M is Ir, Os, or Ru, then at least two of adjacent X 1 —X 3 are C, and are fused to a structure of Formula II

if metal M is Pt, Pd, Cu, Ag, or Au, then at least two of adjacent X 1 —X 4 are C, and are fused to a structure of Formula II;

each of K 1 and K 2 is independently a direct bond, O, or S;

Y is selected from the group consisting of O, S, Se, BR, NR, CRR′, and SiRR′;

L 1 is selected from the group consisting of O, S, NR, CRR′, and SiRR′;

each of R A , R B , R C , R D , R E , and R F independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R, R′, R A , R B , R C , R D , R E , R F , and R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

any two adjacent R, R′, R A , R B , R C , R D , R E , R F , or R X can be joined or fused together to form a ring;

wherein the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein, if the compound has a structure of

 where no two R E are joined or fused to form a ring, then at least one of the following is true: (i) R X comprises at least three aromatic moieties that are not fused to each other and at least one of the aromatic moieties is substituted, or (ii) R X comprises at least 5 aromatic rings and two are heteroaromatic rings, or (iii) R X comprises silyl and at least three aromatic moieties that are not fused to each other.

2 . The compound of claim 1 , wherein X is C and ring B is a 6-membered aromatic ring.

3 . The compound of claim 1 , wherein X is N and ring B is a 5-membered ring.

4 . The compound of claim 1 , wherein X 1 and X 2 are both C and are joined with Formula II to form a fused ring structure.

5 . The compound of claim 1 , wherein X 2 and X 3 are both C and are joined with Formula II to form a fused ring structure.

6 . The compound of claim 1 , wherein the compound comprises a ligand L A of

wherein:

each of X 8 —X 11 is independently C or N;

R H represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

R H for each occurrence is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

any two adjacent R A , R C , or R H can be joined to form a ring.

7 . A compound of

wherein:

M is Pd or Pt;

Z 1 -Z 2 are each independently C or N with one being N and the other C;

Z 3 -Z 4 are each independently C or N with one being N and the other C;

X is C or N;

each of X 1 —X 6 , and X 12 —X 13 is independently C or N;

at least two of adjacent X 1 —X 4 are C, and are fused to a structure of

each of K 1 , K 2 , K 3 , and K 4 is independently a direct bond, O, or S, with at least two of K 1 , K 2 , K 3 , and K 4 being direct bonds;

Y is selected from the group consisting of O, S, Se, BR, NR, CRR′, and SiRR′;

L is absent, a direct bond, or a linker selected from the group consisting of

 and combinations thereof;

L 1 is selected from the group consisting of O, S, NR, CRR′, and SiRR′; and

L 2 is selected from the group consisting of a direct bond, O, S, NR, CRR′, and SiRR′;

ring B, ring E, and ring F are each independently 5-membered or 6-membered aromatic rings;

each of R A , R B , R C , R D , R E , and R F independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R, R′, R A , R B , R C , R D , R E , and R F is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

any two adjacent R, R′, R A , R B , R C , R D , R E , or R F can be joined or fused together to form a ring.

8 . The compound of claim 7 , wherein X is C and ring B is a 6-membered aromatic ring.

9 . The compound of claim 7 , wherein X is N and ring B is a 5-membered ring.

10 . The compound of claim 7 , wherein the compound has a structure of

wherein:

each of X 8 —X 11 is independently C or N;

R H represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

R H for each occurrence is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

any two adjacent R, R′, R A , R B , R C , R D , R E , or R F can be joined to form a ring.

11 . The compound of claim 7 , wherein the compound is selected from the group consisting of:

wherein

L 1 is selected from the group consisting of O, S, NR, CRR′, and SiRR′;

each of R A , R B , R C , R D , R E , R F , and R G independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R, R′, R A , R B , R C , R D , R E , R F , R G , and R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

any two adjacent R, R′, R A , R B , R C , R D , R E , R F , or R G can be joined or fused together to form a ring.

12 . The compound of claim 7 , wherein the compound is selected from the group consisting of:

each of R G and R H independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

wherein each R G , R H , R a , R b , R c , and R d is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two adjacent R, R′, R A , R B , R C , R D , R E , R F , R G , R H , R a , R b , R c , and R d can be joined or fused together to form a ring.

13 . The compound of claim 7 , wherein the compound has a structure of

wherein L A is selected from the group consisting of L A 1-(Bi)(Bj), L A 2-(Bi)(Bj), L A 3-(Bi)(Bj), L A 4-(Bi)(Bj), L A 5-(Bi)(Bj), L A 6-(Bi)(Bj), L A 7-(Bi), L A 8-(Bi), L A 9-(Bi), L A 10-(Bi), L A 11-(Bi), L A 12-(Bi), L A 13-(Bi), L A 14-(Bi), L A 15-(Bi), L A 16-(Bi), L A 17-(Bi), L A 18-(Bi), L A 19-(Bi), L A 20-(Bi), L A 21-(Bi), L A 22-(Bi), L A 23-(Bi), L A 24-(Bi), L A 25-(Bi)(Bj), L A 26-(Bi)(Bj), L A 27-(Bi)(Bj), L A 28-(Bi)(Bj), L A 29-(Bi)(Bj), L A 30-(Bi)(Bj), L A 31-(Bi), L A 32-(Bi), L A 33-(Bi), L A 34-(Bi), L A 35-(Bi), L A 36-(Bi), L A 37-(Bi), L A 38-(Bi), L A 39-(Bi), L A 40-(Bi), L A 41-(Bi), L A 42-(Bi), L A 43-(Bi), L A 44-(Bi), L A 45-(Bi), L A 46-(Bi), L A 47-(Bi), and L A 48-(Bi), wherein i is an integer from 1 to 47, and j is an integer from 1 to 40, and each L A is as defined below:

L A

Structure of L A

for L A 1-(Bi)(Bj), L A 1-(B1)(B1) to L A 1-(B47)(B40) having the structure

for L A 2-(Bi)(Bj), L A 2-(B1)(B1) to L A 2-(B47)(B40) having the structure

for L A 3-(Bi)(Bj), L A 3-(B1)(B1) to L A 3-(B47)(B40) having the structure

for L A 4-(Bi)(Bj), L A 4-(B1)(B1) to L A 4-(B47)(B40) having the structure

for L A 5-(Bi)(Bj), L A 5-(B1)(B1) to L A 5-(B47)(B40) having the structure

for L A 6-(Bi)(Bj), L A 6-(B1)(B1) to L A 6-(B47)(B40) having the structure

for L A 7-(Bi), L A 7-(B1) to L A 7-(B47) having the structure

for L A 8-(Bi), L A 8-(B1) to L A 8-(B47) having the structure

for L A 9-(Bi), L A 9-(B1) to L A 9-(B47) having the structure

for L A 10-(Bi), L A 10-(B1) to L A 10-(B47) having the structure

for L A 11-(Bi), L A 11-(B1) to L A 11-(B47) having the structure

for L A 12-(Bi), L A 12-(B1) to L A 12-(B47) having the structure

for L A 13-(Bi), L A 13-(B1) to L A 13-(B47) having the structure

for L A 14-(Bi), L A 14-(B1) to L A 14-(B47) having the structure

for L A 15-(Bi), L A 15-(B1) to L A 15-(B47) having the structure

for L A 16-(Bi), L A 16-(B1) to L A 16-(B47) having the structure

for L A 17-(Bi), L A 17-(B1) to L A 17-(B47) having the structure

for L A 18-(Bi), L A 18-(B1) to L A 18-(B47) having the structure

for L A 19-(Bi), L A 19-(B1) to L A 19-(B47) having the structure

for L A 20-(Bi), L A 20-(B1) to L A 20-(B47) having the structure

for L A 21-(Bi), L A 21-(B1) to L A 21-(B47) having the structure

for L A 22-(Bi), L A 22-(B1) to L A 22-(B47) having the structure

for L A 23-(Bi), L A 23-(B1) to L A 23-(B47) having the structure

for L A 24-(Bi), L A 24-(B1) to L A 24-(B47) having the structure

for L A 25-(Bi)(Bj), L A 25-(B1)(B1) to L A 25-(B47)(B40) having the structure

for L A 26-(Bi)(Bj), L A 26-(B1)(B1) to L A 26-(B47)(B40) having the structure

for L A 27-(Bi)(Bj), L A 27-(B1)(B1) to L A 27-(B47)(B40) having the structure

for L A 28-(Bi)(Bj), L A 28-(B1)(B1) to L A 28-(B47)(B40) having the structure

for L A 29-(Bi)(Bj), L A 29-(B1)(B1) to L A 29-(B47)(B40) having the structure

for L A 30-(Bi)(Bj), L A 30-(B1)(B1) to L A 30-(B47)(B40) having the structure

for L A 31-(Bi), L A 31-(B1) to L A 31-(B47) having the structure

for L A 32-(Bi), L A 32-(B1) to L A 32-(B47) having the structure

for L A 33-(Bi), L A 33-(B1) to L A 33-(B47) having the structure

for L A 34-(Bi), L A 34-(B1) to L A 34-(B47) having the structure

for L A 35-(Bi), L A 35-(B1) to L A 35-(B47) having the structure

for L A 36-(Bi), L A 36-(B1) to L A 36-(B47) having the structure

for L A 37-(Bi), L A 37-(B1) to L A 37-(B47) having the structure

for L A 38-(Bi), L A 38-(B1) to L A 38-(B47) having the structure

for L A 39-(Bi), L A 39-(B1) to L A 39-(B47) having the structure

for L A 40-(Bi), L A 40-(B1) to L A 40-(B47) having the structure

For L A 41-(Bi), L A 41-(B1) to L A 41-(B47) having the structure

for L A 42-(Bi), L A 42-(B1) to L A 42-(B47) having the structure

for L A 43-(Bi), L A 43-(B1) to L A 43-(B47) having the structure

for L A 44-(Bi), L A 44-(B1) to L A 44-(B47) having the structure

for L A 45-(Bi), L A 45-(B1) to L A 45-(B47) having the structure

for L A 46-(Bi), L A 46-(B1) to L A 46-(B47) having the structure

for L A 47-(Bi), L A 47-(B1) to L A 47-(B47) having the structure

for L A 48-(Bi), L A 48-(B1) to L A 48-(B47) having the structure

wherein B1 to B47 have the following structures:

and

wherein L B is selected from the group consisting of L B 1-(Rk′)(Rl)(Rm)(Rn), L B 2-(Rk)(Rm)(Rm), L B 3-(Rk′)(Rl)(Rm)(Rn), L B 4-(Rk)(Rl)(Rm), L B 5-(Rk)(Rl)(Rm), L B 6-(Rk)(Rl), L B 7-(Rk)(Rl)(Rm), L B 8-(Rk)(Rl), L B 9-(Rg)(Rl)(Rm)(Rn), L B 10-(Rg)(Rl)(Rm), L B 11-(Rg)(Rl)(Rm), L B 12-(Rg)(Rl)(Rm)(Rn), L B 13-(Rg)(Rl)(Rm), L B 14-(Rg)(Rl)(Rm), L B 15-(Rg)(Rl)(Rm), L B 16-(Rg)(Rl)(Rm)(Rn), L B 17-(Rk)(Rl)(Rm), L B 18-(Rk)(Rl), L B 19-(Rk)(Rl)(Rm), L B 20-(Rk)(Rl)(Rm), L B 21-(Rk)(Rl)(Rm), L B 22-(Rk)(Rl)(Rm), L B 23-(Rk)(Rl)(Rm), L B 24-(Rk)(Rl)(Rm), L B 25-(Rk)(Rl)(Rm), L B 26-(Rk)(Rl)(Rm), L B 27-(Rk)(Rl)(Rm)(Rn), L B 28-(Rk)(Rl)(Rm)(Rn), L B 29-(Rg)(Rl)(Rm), L B 30-(Rk)(Rl)(Rm)(Rn), L B 31-(Rg)(Rl)(Rm), L B 32-(Rk′)(Rl)(Rm), L B 33-(Rk′)(Rl), L B 34-(Rk′)(Rl), L B 35-(Rk)(Rl)(Rm)(Rn), L B 36-(Rg)(Rl), L B 37-(Rg)(Rl)(Rm), L B 38-(Rg)(Rl), L B 39-(Rg)(Rl), L B 40-(Rg)(Rl), L B 41-(Rg)(Rl), L B 42-(Rg)(Rl)(Rm)(Rn), and L B 43-(Rg)(Rl)(Rm)(Rn), wherein k is an integer from 1 to 292, k′ is an integer from 113-115, 133, 138, 140-141, 146, 149, 154, 178-186, 188-190, 194-199, 201-212, 215-218, 221-224, 227-230, 233-237, 239-242, 251-253, 255-174, and 276-292, and g, l, m, and n are each independently an integer from 1 to 307, and each structure of L B is as defined below:

L B

Structure of L B

for L B 1-(Rk′)(Rl)(Rm)(Rn), L B 1-(R113)(R1)(R1)(R1) to L B 1- (R292)(R307)(R307)(R307) having the structure

for L B 2-(Rk)(Rl)(Rm), L B 2-(R1)(R1)(R1) to L B 2-(R292)(R307)(R307) having the structure

for L B 3-(Rk′)(Rl)(Rm)(Rn), L B 3-(R113)(R1)(R1)(R1) to L B 3- (R292)(R307)(R307)(R307) having the structure

for L B 4-(Rk)(Rl)(Rm), L B 4-(R1)(R1)(R1) to L B 4-(R292)(R307)(R307) having the structure

for L B 5-(Rk)(Rl)(Rm), L B 5-(R1)(R1)(R1) to L B 5-(R292)(R307)(R307) having the structure

for L B 6-(Rk)(Rl), L B 6-(R1)(R1) to L B 6-(R292)(R307) having the structure

for L B 7-(Rk)(Rl)(Rm), L B 7-(R1)(R1)(R1) to L B 7-(R292)(R307)(R307) having the structure

for L B 8-(Rk)(Rl), L B 8-(R1)(R1) to L B 8-(R292)(R307) having the structure

for L B 9-(Rg)(Rl)(Rm)(Rn), L B 9-(R1)(R1)(R1)(R1) to L B 9- (R307)(R307)(R307)(R307) having the structure

for L B 10-(Rg)(Rl)(Rm), L B 10-(R1)(R1)(R1) to L B 10- (R307)(R307)(R307) having the structure

for L B 11-(Rg)(Rl)(Rm), L B 11-(R1)(R1)(R1) to L B 11- (R307)(R307)(R307) having the structure

for L B 12-(Rg)(Rl)(Rm)(Rn), L B 12-(R1)(R1)(R1)(R1) to L B 12- (R307)(R307)(R307)(R307) having the structure

for L B 13-(Rg)(Rl)(Rm), L B 13-(R1)(R1)(R1) to L B 13- (R307)(R307)(R307) having the structure

for L B 14-(Rg)(Rl)(Rm), L B 14-(R1)(R1)(Rl) to L B 14- (R307)(R307)(R307)

for L B 15-(Rg)(Rl)(Rm), L B 15-(R1)(R1)(R1) to L B 15- (R307)(R307)(R307) having the structure

for L B 16-(Rg)(Rl)(Rm)(Rn), L B 16-(R1)(R1)(R1)(R1) to L B 16- (R307)(R307)(R307)(R307)

for L B 17-(Rk)(Rl)(Rm), L B 17-(R1)(R1)(R1) to L B 17- (R292)(R307)(R307) having the structure

for L B 18-(Rk)(Rl), L B 18-(R1)(R1) to L B 18-(R292)(R307) having the structure

for L B 19-(Rk)(Rl)(Rm), L B 19-(R1)(R1)(R1) to L B 19- (R292)(R307)(R307) having the structure

for L B 20-(Rk)(Rl)(Rm), L B 20-(R1)(R1)(R1) to L B 20- (R292)(R307)(R307) having the structure

for L B 21-(Rk)(Rl)(Rm), L B 21-(R1)(R1)(R1) to L B 21- (R292)(R307)(R307) having the structure

for L B 22-(Rk)(Rl)(Rm), L B 22-(R1)(R1)(R1) to L B 22- (R292)(R307)(R307) having the structure

for L B 23-(Rk)(Rl)(Rm), L B 23-(R1)(R1)(R1) to L B 23- (R292)(R307)(R307) having the structure

for L B 24-(Rk)(Rl)(Rm), L B 24-(R1)(R1)(R1) to L B 24- (R292)(R307)(R307) having the structure

for L B 25-(Rk)(Rl)(Rm), L B 25-(R1)(R1)(R1) to L B 25- (R292)(R307)(R307) having the structure

for L B 26-(Rk)(Rl)(Rm), L B 26-(R1)(R1)(R1) to L B 26- (R292)(R307)(R307) having the structure

for L B 27-(Rk)(Rl)(Rm)(Rn), L B 27-(R1)(R1)(R1)(R1) to L B 27- (R292)(R307)(R307)(R307) having the structure

for L B 28-(Rk)(Rl)(Rm)(Rn), L B 28-(R1)(R1)(R1)(R1) to L B 28- (R292)(R307)(R307)(R307) having the structure

for L B 29-(Rg)(Rl)(Rm), L B 29-(R1)(R1)(R1) to L B 29- (R307)(R307)(R307)

for L B 30-(Rk)(Rl)(Rm)(Rn), L B 30-(R1)(R1)(R1)(R1) to L B 30- (R292)(R307)(R307)(R307) having the structure

for L B 31-(Rg)(Rl)(Rm), L B 31-(R1)(R1)(R1) to L B 31- (R307)(R307)(R307) having the structure

for L B 32-(Rk′)(Rl)(Rm), L B 32-(R113)(R1)(R1) to L B 32- (R292)(R307)(R307) having the structure

for L B 33-(Rk′)(Rl), L B 33-(R113)(R1) to L B 33-(R292)(R307) having the structure

for L B 34-(Rk′)(Rl), L B 34-(R113)(R1) to L B 34-(R292)(R307) having the structure

for L B 35-(Rk)(Rl)(Rm)(Rn), L B 35-(R1)(R1)(R1)(R1) to L B 35- (R292)(R307)(R307)(R307) having the structure

for L B 36-(Rg)(Rl), L B 36-(R1)(R1) to L B 36-(R307)(R307) having the structure

for L B 37-(Rg)(Rl)(Rm), L B 37-(R1)(R1)(R1) to L B 37- (R307)(R307)(R307) having the structure

for L B 38-(Rg)(Rl), L B 38-(R1)(R1) to L B 38-(R307)(R307) having the structure

for L B 39-(Rg)(Rl), L B 39-(R1)(R1) to L B 39-(R307)(R307) having the structure

for L B 40-(Rg)(Rl), L B 40-(R1)(R1) to L B 40-(R307)(R307) having the structure

for L B 41-(Rg)(Rl), L B 41-(R1)(R1) to L B 41-(R307)(R307) having the structure

for L B 42-(Rg)(Rl)(Rm)(Rn), L B 42-(R1)(R1)(R1)(R1) to L B 42- (R307)(R307)(R307)(R307)

for L B 43-(Rg)(Rl)(Rm)(Rn), L B 43-(R1)(R1)(R1)(R1) to L B 43- (R307)(R307)(R307)(R307) having the structure

where R1 to R307 have the following structures:

and

wherein L C is selected from the group consisting of L C 1-(Bm)(Bn), L C 2-(Bm)(Bn), L C 3-(Bm)(Bn), L C 4-(Bm)(Bn), L C 5-(Bm)(Bn), L C 6-(Bm)(Bn), L C 7-(Bm), L C 8-(Bm), L C 9-(Bm), L C 10-(Bm), L C 11-(Bm), L C 12-(Bm), L C 13-(Bm), L C 14-(Bm), L C 15-(Bm), L C 16-(Bm), L C 17-(Bm), L C 18-(Bm), L C 19-(Bm), L C 20-(Bm), L C 21-(Bm), L C 22-(Bm), L C 23-(Bm), L C 24-(Bm), L C 25-(Bm)(Bn), L C 26-(Bm)(Bn), L C 27-(Bm)(Bn), L C 28-(Bm)(Bn), L C 29-(Bm)(Bn), L C 30-(Bm)(Bn), L C 31-(Bm), L C 32-(Bm), L C 33-(Bm), L C 34-(Bm), L C 35-(Bm), L C 36-(Bm), L C 37-(Bm), L C 38-(Bm), L C 39-(Bm), L C 40-(Bm), L C 41-(Bm), L C 42-(Bm), L C 43-(Bm), L C 44-(Bm), L C 45-(Bm), L C 46-(Bm), L C 47-(Bm), and L C 48-(Bm), wherein m is an integer from 1 to 47, and n is an integer from 1 to 40, and each L C is as defined below:

L C

Structure of L C

for L C 1-(Bm)(Bn), L C 1-(B1)(B1) to L C 1-(B47)(B40) having the structure

for L C 2-(Bm)(Bn), L C 2-(B1)(B1) to L C 2-(B47)(B40) having the structure

for L C 3-(Bm)(Bn), L C 3-(B1)(B1) to L C 3-(B47)(B40) having the structure

for L C 4-(Bm)(Bn), L C 4-(B1)(B1) to L C 4-(B47)(B40) having the structure

for L C 5-(Bm)(Bn), L C 5-(B1)(B1) to L C 5-(B47)(B40) having the structure

for L C 6-(Bm)(Bn), L C 6-(B1)(B1) to L C 6-(B47)(B40) having the structure

for L C 7-(Bm), L C 7-(B1) to L C 7-(B47) having the structure

for L C 8-(Bm), L C 8-(B1) to L C 8-(B47) having the structure

for L C 9-(Bm), L C 9-(B1) to L C 9-(B47) having the structure

for L C 10-(Bm), L C 10-(B1) to L C 10-(B47) having the structure

for L C 11-(Bm), L C 11-(B1) to L C 11-(B47) having the structure

for L C 12-(Bm), L C 12-(B1) to L C 12-(B47) having the structure

for L C 13-(Bm), L C 13-(B1) to L C 13-(B47) having the structure

for L C 14-(Bm), L C 14-(B1) to L C 14-(B47) having the structure

for L C 15-(Bm), L C 15-(B1) to L C 15-(B47) having the structure

for L C 16-(Bm), L C 16-(B1) to L C 16-(B47) having the structure

for L C 17-(Bm), L C 17-(B1) to L C 17-(B47) having the structure

for L C 18-(Bm), L C 18-(B1) to L C 18-(B47) having the structure

for L C 19-(Bm), L C 19-(B1) to L C 19-(B47) having the structure

for L C 20-(Bm), L C 20-(B1) to L C 20-(B47) having the structure

for L C 21-(Bm), L C 21-(B1) to L C 21-(B47) having the structure

for L C 22-(Bm), L C 22-(B1) to L C 22-(B47) having the structure

for L C 23-(Bm), L C 23-(B1) to L C 23-(B47) having the structure

for L C 24-(Bm), L C 24-(B1) to L C 24-(B47) having the structure

for L C 25-(Bm)(Bn), L C 25-(B1)(B1) to L C 25-(B47)(B40) having the structure

for L C 26-(Bm)(Bn), L C 26-(B1)(B1) to L C 26-(B47)(B40) having the structure

for L C 27-(Bm)(Bn), L C 27-(B1)(B1) to L C 27-(B47)(B40) having the structure

for L C 28-(Bm)(Bn), L C 28-(B1)(B1) to L C 28-(B47)(B40) having the structure

for L C 29-(Bm)(Bn), L C 29-(B1)(B1) to L C 29-(B47)(B40) having the structure

for L C 30-(Bm)(Bn), L C 30-(B1)(B1) to L C 30-(B47)(B40) having the structure

for L C 31-(Bm), L C 31-(B1) to L C 31-(B47) having the structure

for L C 32-(Bm), L C 32-(B1) to L C 32-(B47) having the structure

for L C 33-(Bm), L C 33-(B1) to L C 33-(B47) having the structure

for L C 34-(Bm), L C 34-(B1) to L C 34-(B47) having the structure

for L C 35-(Bm), L C 35-(B1) to L C 35-(B47) having the structure

for L C 36-(Bm), L C 36-(B1) to L C 36-(B47) having the structure

for L C 37-(Bm), L C 37-(B1) to L C 37-(B47) having the structure

for L C 38-(Bm), L C 38-(B1) to L C 38-(B47) having the structure

for L C 39-(Bm), L C 39-(B1) to L C 39-(B47) having the structure

for L C 40-(Bm), L C 40-(B1) to L C 40-(B47) having the structure

for L C 41-(Bm), L C 41-(B1) to L C 41-(B47) having the structure

for L C 42-(Bm), L C 42-(B1) to L C 42-(B47) having the structure

for L C 43-(Bm), L C 43-(B1) to L C 43-(B47) having the structure

for L C 44-(Bm), L C 44-(B1) to L C 44-(B47) having the structure

for L C 45-(Bm), L C 45-(B1) to L C 45-(B47) having the structure

for L C 46-(Bm), L C 46-(B1) to L C 46-(B47) having the structure

for L C 47-(Bm), L C 47-(B1) to L C 47-(B47) having the structure,

and for L C 48-(Bm), L C 48-(B1) to L C 48-(B47) having the structure

14 . An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand L A of

wherein:

ligand L A is coordinated to a metal M selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;

Z 1 -Z 2 are each independently C or N with one being N and the other C;

ring B is a 5-membered or 6-membered aromatic ring;

X is C or N;

each of X 1 —X 7 is independently C or N;

if metal M is Ir, Os, or Ru, then at least two of adjacent X 1 —X 3 are C, and are fused to a structure of Formula II

if metal M is Pt, Pd, Cu, Ag, or Au, then at least two of adjacent X 1 —X 4 are C, and are fused to a structure of Formula II;

each of K 1 and K 2 is independently a direct bond, O, or S;

Y is selected from the group consisting of O, S, Se, BR, NR, CRR′, and SiRR′;

L 1 is selected from the group consisting of O, S, NR, CRR′, and SiRR′;

each of R A , R B , R C , R D , R E , and R F independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R, R′, R A , R B , R C , R D , R E , R F , and R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any two adjacent R, R′, R A , R B , R C , R D , R E , R F , or R X can be joined or fused together to form a ring;

wherein the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein, if the compound has a structure of

 where no two R E are joined or fused to form a ring, then at least one of the following is true: (i) R X comprises at least three aromatic moieties that are not fused to each other and at least one of the aromatic moieties is substituted, or (ii) R X comprises at least 5 aromatic rings and two are heteroaromatic rings, or (iii) R X comprises silyl and at least three aromatic moieties that are not fused to each other.

15 . The OLED of claim 14 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

16 . The OLED of 14 for a consumer product wherein the consumer product is one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.

17 . The compound of claim 7 , wherein the compound is selected from the group consisting of the following structures:

18 . The compound of claim 1 , wherein the compound has a structure of

and R X comprises at least three aromatic moieties that are not fused to each other and at least one of the aromatic moieties is substituted.

19 . The compound of claim 1 , wherein the compound has a structure of

and R X comprises at least 5 aromatic rings and two are heteroaromatic rings.

20 . The compound of claim 1 , wherein the compound has a structure of

and R X comprises silyl and at least three aromatic moieties that are not fused to each other.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Mar 17, 2021
From: CHEN, HSIAO-FAN; WOLOHAN, PETER
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 055622/0485 →
Continuity (2)
Provisional Application 62969220 · Feb 3, 2020
Related Publication 20210253446A1 · Aug 19, 2021
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