Organic electroluminescent materials and devices
Provided are compounds comprising a ligand L A of Formula I where the ligand L A is coordinated to Ir.
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 3 and Z 2 are each independently C or N;
K 3 and Ware 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′, 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;
the metal M is Ir; 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 each R, R′, R A and R B are independently 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.
3. The compound of claim 1 , wherein Z 1 is N, and Z 2 is C.
4. The compound of claim 1 , wherein Z 1 is C, and Z 2 is N.
5. The compound of claim 1 , wherein X 1 -X 3 are all C.
6. The compound of claim 1 , wherein ring A is pyridine, pyrimidine, pyrazine, imidazole, pyrazole, oxazole, thiazole, or imidazole derived carbene.
7. The compound of claim 1 , wherein X is NR′.
8. The compound of claim 7 , wherein R′ and R can be joined to form a ring wherever chemically feasible.
9. The compound of claim 1 , wherein Z 2 and X 1 -X 3 are all C.
10. The compound of claim 1 , wherein each of K 3 and K 4 is a direct bond.
11. The compound of claim 1 , wherein one of K 3 and K 4 is O.
12. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
wherein:
R G for each occurrence represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and
each of R″ and R G 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 R G groups can be joined together to form a ring wherever chemically feasible.
13. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the following structures:
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
wherein Rj = Bj, Rk = Bk, Rp = Bp, and Rz = Bz, and
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
wherein Rj = Bj, Rk = Bk, and Rp = Bp, and
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
wherein Rj = Bj, and Rz = Bz, and
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
wherein Rj = Bj, and
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
wherein Rj = Bj, and Rk = Bk, and
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
wherein Rj = Bj, Rk = Bk, Rp = Bp, and Rz = Bz, and
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
wherein Rj = Bj, Rk = Bk, and Rp = Bp, and
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
wherein Rj = Bj, Rk = Bk, and Rz = Bz, and
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
wherein Rj = Bj, and Rk = Bk, and
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
wherein Rj = Bj, and
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
wherein Rj = Bj, Rk = Bk, and Rz = Bz, and
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
wherein Rj = Bj, Rk = Bk, and Rz = Bz, and
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
wherein Rj = Bj, Rk = Bk, Rp = Bp, and Rz = Bz, and
wherein B1 to B55 have the following structures:
14. The compound of claim 13 , wherein L A is selected from the group consisting of only those ligands whose Ri, Rj, and Rk are one of the following structures: B1, B2, B3, B9, B10, B16, B18, B20, B22, B24, B25, B27, B29, B31, B32, B33, B34, B34, B40, B44, B45, and B46.
15. The compound of claim 13 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ); wherein L A , L B , and L C are different from each other, and L B and L C are each a bidentate ligand.
16. The compound of claim 15 , wherein L B and L C are each independently selected from the group consisting of:
wherein T is selected from the group consisting of B, Al, Ga, and In; each of Y 1 to Y 13 is independently selected from the group consisting of C and N; Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ; R e and R f can be fused or joined to form a ring; each R a , R b , R c , and R d independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; each of R a1 , R b1 , R c1 , R a1 , 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 the general substituents defined herein; and any two adjacent substituents can be fused or joined to form a ring or form a multidentate ligand.
17. The compound of claim 1 , wherein the compound is selected from the group consisting of:
18. An organic light emitting device 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;
the metal M is Ir; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.
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;
the metal M is Ir; 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 .