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US-12623919-B2 - Organic electroluminescent materials and devices

US12623919B2US 12623919 B2US12623919 B2US 12623919B2US-12623919-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.

Inventors

  • Hsiao-Fan Chen
  • Peter Wolohan

Assignees

  • UNIVERSAL DISPLAY CORPORATION

Dates

Publication Date
20260512
Application Date
20210111

Claims (20)

  1. 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. 2 . The compound of claim 1 , wherein X is C and ring B is a 6-membered aromatic ring.
  3. 3 . The compound of claim 1 , wherein X is N and ring B is a 5-membered ring.
  4. 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. 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. 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. 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. 8 . The compound of claim 7 , wherein X is C and ring B is a 6-membered aromatic ring.
  9. 9 . The compound of claim 7 , wherein X is N and ring B is a 5-membered ring.
  10. 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. 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. 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. 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. 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. 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. 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. 17 . The compound of claim 7 , wherein the compound is selected from the group consisting of the following structures:
  18. 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. 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. 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.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 62/969,220, filed on Feb. 3, 2020, the entire contents of which are incorporated herein by reference. FIELD The present disclosure generally relates to organometallic compounds and formulations and their various uses including as emitters in devices such as organic light emitting diodes and related electronic devices. BACKGROUND Opto-electronic devices that make use of organic materials are becoming increasingly desirable for various reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively, the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single emissive layer (EML) device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art. SUMMARY In one aspect, the present disclosure provides a compound comprising a ligand LA of wherein, Z1-Z2 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 X1—X7 is independently C or N; at least two of adjacent X1—X3 are C, and are fused to a structure of Formula II through the two wavy lines; each of K1 and K2 is independently a direct bond, O, or S; Y is selected from the group consisting of O, S, Se, BR, NR, CRR′, and SiRR′; each of RA, RB, RC, and RD independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; each of R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined herein; any two adjacent R, R′, RA, RB, RC, or RD can be joined or fused together to form a ring; wherein the ligand LA is coordinated through the two dashed lines to a metal M selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au; and wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. In another aspect, the present disclosure provides a compound of wherein, M is Pd or Pt; Z1-Z2 are each independently C or N with one being N and the other C; Z3-Z4 are each independently C or N with one being N and the other C; X is C or N; each of X1—X6, and X12—X13 is independently C or N; at least two adjacent X1—X4 are C, and are fused to a structure of Formula II through the two wavy lines; 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; L1 is selected from the group consisting of O, S, NR, CRR′, and SiRR′; and L2 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 RA, RB, RC, RD, RE, and RF independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; each of R, R′, RA, RB, RC, RD, RE, and RF is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and any two adjacent R, R′, RA, RB, RC, RD, RE, or RF can be joined or fused together to form a ring. In yet another aspect, the present disclosure provides a formulation of a compound comprising a ligand LA of Formula I or a compound of formula V as described herein. In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound comprising a ligand LA of Formula I or a compound of Formula V as described herein. In yet another aspect, the presen