Organic electroluminescent materials and devices
Provided are compounds comprising a ligand L A of Formula I
1. A compound comprising a ligand L A of Formula I
wherein:
A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are each independently C or N;
K 3 and K 4 are each independently a direct bond, O, or S;
X 1 , X 2 , and X 3 are each independently C or N, at least one of X 1 , X 2 , and X 3 is C;
X is O or NR′;
R A and R B each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
each of R, R′, R A , and R B 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
two adjacent groups can be joined or fused to form a ring wherever chemically feasible, wherein the ligand L A is complexed to a metal M to form a chelate ring as indicated by the two dotted lines;
the metal M can be coordinated to other ligands; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.
2. The compound of claim 1 , wherein the compound has Formula II
wherein:
M 1 is Pd or Pt;
rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 3 and Z 4 are each independently C or N;
K 1 , K 2 , K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of them are direct bonds;
L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, absent a bond, O, S, CR″R′″, SiR″R′″, BR″, and NR″,
at least one of L 1 and L 2 is not absent a bond;
X 4 -X 6 are each independently C or N;
R C and R D each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each R″, R′″, R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
two adjacent substituents can be joined or fused together to form a ring wherever chemically feasible.
3. The compound of claim 2 , wherein ring C is a 6-membered aromatic ring.
4. The compound of claim 2 , wherein L 1 is O, CRR′, or NR″.
5. The compound of claim 2 , wherein L 2 is a direct bond.
6. The compound of claim 2 , wherein L 2 is NR″.
7. The compound of claim 2 , wherein K 1 , K 2 , K 3 , and K 4 are each a direct bond.
8. The compound of claim 2 , wherein X 4 -X 5 are both N, and X 6 is C.
9. The compound of claim 2 , wherein L 3 is absent a bond.
10. The compound of claim 2 , wherein L 1 is absent a bond.
11. The compound of claim 2 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L A ′)(Ly) with the following structure:
wherein L A ′ is selected from the group consisting of L A ′1-G to L A ′8-G whose structures are defined in LIST7A
below, L A ″ is selected from the group consisting of L A ″9-G to L A ″16-G whose structures are defined in LIST7A
below, L A ′″ is selected from the group consisting of L A ′″16-G whose structures are defined in LIST7A below,
L A ″″ is selected from the group consisting of L A ″″17-G whose structures are defined in LIST7A below, and
L A ′″″ is selected from the group consisting of L A ′″″18-G whose structures are defined in LIST7A below, and
L A ″″″ is selected from the group consisting of L A ″″″19-G to L A ″″″21-G whose structures are defined in LIST7A below:
LIST7A
Ligand naming convention and structure
L A ′1-G having the structure
L A ′8-G having the structure
L A ″15-G having the structure
L A ′2-G having the structure
L A ″9-G having the structure
L A ″16-G having the structure
L A ′3-G having the structure
L A ″10-G having the structure
L A ′′′16-G having the structure
L A ′4-G having the structure
L A ″11-G having the structure
L A ′′″17-G having the structure
L A ′5-G having the structure
L A ″12-G having the structure
L A ′′′′′18-G having the structure
L A ′6-G having the structure
L A ″13-G having the structure
L A ′′′′′′19-G having the structure
L A ′7-G having the structure
LA″14-G having the structure
L A ′′′′′′20-G having the structure
L A ′′′′′′21-G having the structure
wherein i, j, k, l, z, and y are independently an integer from 1 to 55, Ri=Bi, Rj=Bj, Rk=Bk, Rl=Bl, and Rz=Bz, and
B1 to B55 have the following structures:
wherein L y is selected from the group consisting of the structures shown in LIST7B below
LIST7B
L y
L y 1-G having the structure
L y 14-G having the structure
L y 27-G having the structure
L y 2-G having the structure
L y 15-G having the structure
L y 28-G having the structure
L y 3-G having the structure
L y 16-G having the structure
L y 29-G having the structure
L y 4-G having the structure
L y 17-G having the structure
L y 30-G having the structure
L y 5-G having the structure
L y 18-G having the structure
L y 31-G having the structure
L y 6-G having the structure
L y 19-G having the structure
L y 32-G having the structure
L y 7-G having the structure
L y 20-G having the structure
L y 33-G having the structure
L y 8-G having the structure
L y 21-G having the structure
L y 34-G having the structure
L y 9-G having the structure
L y 22-G having the structure
L y 35-G having the structure
L y 10-G having the structure
L y 23-G having the structure
L y 36-G having the structure
L y 11-G having the structure
L y 24-G having the structure
L y 37-G having the structure
L y 12-G having the structure
L y 25-G having the structure
L y 38-G having the structure
L y 13-G having the structure
L y 26-G having the structure
L y 39-G having the structure
wherein R, R C , R D , and R E each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; each R 1 , R 2 , R 3 , R 4 , R, R′, R A , and R B are independently a hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and two adjacent groups can be joined or fused to form a ring wherever chemically feasible.
12. The compound of claim 2 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L A )(Ly) having the following structures:
wherein L A ′ to L A ″″″ are selected from the group having the structures shown below:
Ligand naming convention
Structure
L A ′1-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′1-(1)(1)(1)(1) to L A ′1-(55)(55)(55)(55) having the structure
L A ′2-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A ′2-(1)(1)(1) to L A ′2- (55)(55)(55) having the structure
L A ′3-(j)(z), wherein each of j, and z is independently an integer from 1 to 55, wherein L A ′3-(1)(1) to L A ′3-(55)(55) having the structure
L A ′4-(j), wherein j is an integer from 1 to 55, wherein L A ′4-(1) to L A ′4-(55) having the structure
L A ′5-(j)(k), wherein each of j, and k is independently an integer from 1 to 55, wherein L A ′5-(1)(1) to L A ′5-(55)(55) having the structure
L A ″6-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ″6- (1)(1)(1)(1) to L A′ ″6-(55)(55)(55)(55) having the structure
L A ″7-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A ″7-(1)(1)(1) to L A ″7-(55)(55)(55) having the structure
L A ″8-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ″8-(1)(1)(1) to L A ″8- (55)(55)(55) having the structure
L A ″9-(j)(k), wherein each of j, and k is independently an integer from 1 to 55, wherein L A ″9-(1)(1) to L A ″9-(55)(55) having the structure
L A ″10-(j), wherein j is an integer from 1 to 55, wherein L A ″10-(1) to L A ″10- (55) having the structure
L A ′′′11-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ′′′11-(1)(1)(1) to L A ′′′11-(55)(55)(55) having the structure
L A ′′′′12-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ′′′′12-(1)(1)(1) to L A ′′′′12-(55)(55)(55) having the structure
L A ′′′′′13-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′′′′′13- (1)(1)(1)(1) to L A ′′′′′13- (55)(55)(55)(55) having the structure
L A ′′′′′′14-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′′′′′′14- (1)(1)(1)(1) to L A ′′′′′′14- (55)(55)(55)(55) having the structure
L A ′′′′′′15-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′′′′′′15- (1)(1)(1)(1) to L A ′′′′′′15- (55)(55)(55)(55) having the structure
L A ′′′′′′16-(j), wherein j is an integer from 1 to 55, wherein L A ′′′′′′16-(1) to L A ′′′′′′16-(55) having the structure
L A ′′′′′′17-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′′′′′′17- (1)(1)(1)(1) to L A ′′′′′′17- (55)(55)(55)(55) having the structure
L A ′18-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′18- (1)(1)(1)(1) to L A ′18-(55)(55)(55)(55) having the structure
L A ′19-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A ′19-(1)(1)(1) to L A ′19-(55)(55)(55) having the structure
L A ′20-(j)(z), wherein each of j, and z is independently an integer from 1 to 55, wherein L A ′20-(1)(1) to L A ′20-(55)(55) having the structure
L A ′21-(j), wherein j is an integer from 1 to 55, wherein L A ′21-(1) to L A ′21- (55) having the structure
L A ′22-(j)(k), wherein each of j, and k is independently an integer from 1 to 55, wherein L A ′22-(1)(1) to L A ′22-(55)(55) having the structure
L A ″23-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ″23- (1)(1)(1)(1) to L A′ ″23-(55)(55)(55)(55) having the structure
L A ″24-(j)(k)(p), wherein each of j, k, and p is independently an integer from 1 to 55, wherein L A ″24-(1)(1)(1) to L A ″24-(55)(55)(55) having the structure
L A ″25-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ″25-(1)(1)(1) to L A ″25-(55)(55)(55) having the structure
L A ″26-(j)(k), wherein each of j, and k is independently an integer from 1 to 55, wherein L A ″26-(1)(1) to L A ″26- (55)(55) having the structure
L A ″27-(j), wherein j is an integer from 1 to 55, wherein L A ″27-(1) to L A ″27- (55) having the structure
L A ′′′28-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ′′′28-(1)(1)(1) to L A ′′′28-(55)(55)(55) having the structure
L A ′′′′29-(j)(k)(z), wherein each of j, k, and z is independently an integer from 1 to 55, wherein L A ′′′′29-(1)(1)(1) to L A ′′′′29-(55)(55)(55) having the structure
L A ′′′′′30-(j)(k)(p)(z), wherein each of j, k, p, and z is independently an integer from 1 to 55, wherein L A ′′′′′30- (1)(1)(1)(1) to L A ′′′′′30- (55)(55)(55)(55) having the structure
wherein Rj=Bj, Rk=Bk, Rp=Bp, and Rz=Bz, and B1 to B55 have the following structures:
and Ly is selected from the group having the structures as shown below:
L y
Structure of L y
R B1 -R B17
L y 1-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 330, wherein L y 1- (1)(1)(1)(1) to L y 1- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,
L y 2-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 330, wherein L y 2-(1)(1)(1) to L y 2-(330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 3-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 3-(1)(1)(1)(1) to L y 3- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B7 = Rj, R B8 = Rk, and R B11 = Ro,
L y 4-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 4-(1)(1)(1) to L y 4- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 5-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 5-(1)(1)(1) to L y 5- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk
L y 6-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 6-(1)(1) to Ly6-(330)(330), having the structure
wherein R B6 = Ri and R B7 = Rj,
L y 7-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 7-(1)(1)(1) to L y 7- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 8-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 8-(1)(1) to L y 8-(330)(330), having the structure
wherein R B1 = Ri and R B6 = Rj,
L y 9-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 9-(1)(1)(1)(1) to L y 9- (330)(330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,
L y 10-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 10-(1)(1)(1) to L y 10- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 11-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 11-(1)(1)(1) to L y 11- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 12-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 12-(1)(1)(1)(1) to L y 12- (330)(330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,
L y 13-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 13-(1)(1)(1) to L y 13- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 14-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 14-(1)(1)(1) to L y 14- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 15-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 15-(1)(1)(1) to L y 15- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 16-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 16-(1)(1)(1)(1) to L y 16- (330)(330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,
L y 17-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 17-(1)(1)(1) to L y 17- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 18-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 18-(1)(1) to L y 18-(330)(330), having the structure
wherein R B1 = Ri and R B6 = Rj,
L y 19-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 19-(1)(1)(1) to L y 19- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 20-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 20-(1)(1)(1) to L y 20- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 21-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 21-(1)(1)(1) to L y 21- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 22-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 22-(1)(1)(1) to L y 22- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 23-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 23-(1)(1)(1) to L y 23- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 24-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 24-(1)(1)(1) to L y 24- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 25-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 25-(1)(1)(1) to L y 25- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 26-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 26-(1)(1)(1) to L y 26- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 27-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 27-(1)(1)(1)(1) to L y 27- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,
L y 28-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 28-(1)(1)(1)(1) to L y 28- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,
L y 29-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 29-(1)(1)(1) to L y 29- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 30-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 30-(1)(1)(1)(1) to L y 30- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,
L y 31-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 31-(1)(1)(1) to L y 31- (330)(330)(330), having the structure
wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,
L y 32-(i)(j)(k), wherein i, j, and k are each an integer from 1 to 330, wherein L y 32-(1)(1)(1) to L y 32- (330)(330)(330), having the structure
wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,
L y 33-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 33-(1)(1) to L y 33-(330)(330), having the structure
wherein R B1 = Ri and R B6 = Rj,
L y 34-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 34-(1)(1) to L y 34-(330)(330), having the structure
wherein R B1 = Ri and R B6 = Rj,
L y 35-(i)(j)(k)(o), wherein i, j, k, and o are each an integer from 1 to 330, wherein L y 35-(1)(1)(1)(1) to L y 35- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B6 = Rk, and R B7 = Ro,
L y 36-(i)(j), wherein i and j are each an integer from 1 to 330, wherein L y 36-(1)(1) to L y 36-(330)(330), having the structure
wherein R B1 = Ri and R B2 = Rj,
L y 37-(i)(j)(k) wherein each of i, j, and k is independently an integer from 1 to 330, wherein L y 37- (1)(1)(1) to L y 37-(330)(330)(330) having the structure
wherein R 1 = Ri, R 2 = Rj, and R 3 = Rk, and
L y 38-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L y 38-(1)(1) to L y 38- (330)(330) having the structure
wherein R 1 = Ri and R 2 = Rj, and
L y 39-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L y 39-(1)(1) to L y 39- (330)(330) having the structure
wherein R 1 = Ri and R 2 = Rj, and
L y 40-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L y 40-(1)(1) to L y 40- (330)(330) having the structure
wherein R 1 = Ri and R 2 = Rj, and
L y 41-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L y 41-(1)(1) to L y 41- (330)(330) having the structure
wherein R 1 = Ri and R 2 = Rj, and
L y 42-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 330, L y 42-(1)(1)(1)(1) to L y 42-(330)(330)(330)(330) having the structure
wherein R 1 = Ri, R 2 = Rj, R 3 = Rk, and R 4 = Rl, and
L y 43-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 330, wherein L y 43- (1)(1)(1)(1) to L y 43- (330)(330)(330)(330) having the structure
wherein R 1 = Ri, R 2 = Rj, R 3 = Rk, and R 4 = Rl.
L y 44-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 330, wherein L y 44- (1)(1)(1)(1)(1) to L y 44- (330)(330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, R B6 = Rl, and R B7 = Rm,
L y 45-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 330, wherein L y 45- (1)(1)(1)(1)(1) to L y 45- (330)(330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, R B6 = Rl, and R B7 = Rm,
L y 46-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 330, wherein L y 46- (1)(1)(1)(1)(1) to L y 46- (330)(330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, R B4 = Rl, and R B5 = Rm,
L y 47-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 330, wherein L y 47- (1)(1)(1)(1)(1) to L y 47- (330)(330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, R B4 = Rl, and R B5 = Rm,
L y 48-(i)(j)(k)(l) wherein i, j, k, and l are each independently an integer from 1 to 330, wherein L y 48- (1)(1)(1)(1) to L y 48- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, and R B4 = Rl,
L y 49-(i)(j)(k)(l) wherein i, j, k, and l are each independently an integer from 1 to 330, wherein L y 49- (1)(1)(1)(1) to L y 49- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, and R B4 = Rl,
L y 50-(i)(j)(k)(l) wherein i, j, k, and l are each independently an integer from 1 to 330, wherein L y 50- (1)(1)(1)(1) to L y 50- (330)(330)(330)(330), having the structure
wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, and R B4 = Rl,
wherein R1 to R330 have the following structures:
13. The compound of claim 12 , wherein the compound is selected from the group consisting of those compounds whose Ri, Rj, and Rk correspond to one of the following structures: B1, B2, B3, B9, B10, B16, B18, B20, B22, B23, B24, B25, B27, B29, B31, B32, B33, B34, B34, B40, B44, B45, and B46.
14. The compound of claim 12 , wherein the compound is selected from the group consisting of those compounds comprising ligand Ly, whose R 1 corresponds to one of the following structures: R1, R2, R3, R10, R12, R20, R21, R22, R23, R27, R28, R29, R37, R38, R40, R41, R42, R52, R53, R54, R66, R67, R73, R74, R93, R94, R96, R101, R106, R130, R134, R135, R136, R137, R316, R317, R321, R322, R328, R329, R330, and R331.
15. The compound of claim 2 , wherein the compound is selected from the group consisting of:
16. 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 Formula I
wherein:
A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are each independently C or N;
K 3 and K 4 are each independently a direct bond, O, or S;
X 1 , X 2 , and X 3 are each independently C or N, at least one of X 1 , X 2 , and X 3 is C;
X is O or NR′;
R A and R B each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
each of R, R′, R A , and R B 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
two adjacent groups can be joined or fused to form a ring wherever chemically feasible, wherein the ligand L A is complexed to a metal M to form a chelate ring as indicated by the two dotted lines;
the metal M can be coordinated to other ligands; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.
17. The OLED of claim 16 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group 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).
18. The OLED of claim 16 , wherein the host is selected from the group consisting of:
and combinations thereof.
19. A consumer product comprising 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 Formula I
wherein:
A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are each independently C or N;
K 3 and K 4 are each independently a direct bond, O, or S;
X 1 , X 2 , and X 3 are each independently C or N, at least one of X 1 , X 2 , and X 3 is C;
X is O or NR′;
R A and R B each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
each of R, R′, R A , and R B 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
two adjacent groups can be joined or fused to form a ring wherever chemically feasible, wherein the ligand L A is complexed to a metal M to form a chelate ring as indicated by the two dotted lines;
the metal M can be coordinated to other ligands; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.
20. A formulation comprising a compound according to claim 1 .