Organic electroluminescent materials and devices
New organometallic complexes having bis- or tris-heteroleptic ligands and large aspect ratio in one direction and their use in OLEDs to enhance the efficiency is disclosed.
1. A compound having a formula selected from the group consisting of:
wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein in Formula III:
L 1 and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
n 1 , n 2 each independently is 0 or 1;
when n 1 or n 2 is 1, L 2 or L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof; and
when n 1 or n 2 is 0, L 2 or L 4 is not present;
Q 1 , Q 2 , Q 3 and Q 4 each independently selected from the group consisting of direct bond and oxygen;
when any of Z 1 , Z 2 , Z 3 and Z 4 is nitrogen, the Q 1 , Q 2 , Q 3 and Q 4 attached thereto is a direct bond;
ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
wherein R 1 , R 2 , R 3 , and R 4 each represents mono to the maximum possible number of substitution, or no substitution;
wherein Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from the group consisting of carbon and nitrogen;
wherein M 2 is a metal selected from the group consisting of Pt and Pd;
wherein a fourth distance is the distance between the atom in R 1 that is the farthest away from M 2 to the atom in R 4 that is the farthest away from M 2 ;
wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M 2 to the atom in R 3 that is the farthest away from M 2 ;
wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
wherein R, R′, R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein (i) each of R 1 and R 4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R 1 and R 4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl; and
wherein any two substituents among R, R′, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring.
2. The compound of claim 1 , wherein M 2 is Pt.
3. The compound of claim 1 , wherein rings A, B, C, and D are each independently selected from the group consisting of phenyl, pyridine, imidazole, and imidazole-derived carbene.
4. The compound of claim 1 , wherein rings A and C are phenyl.
5. The compound of claim 1 , wherein rings B and D are selected from the group consisting of pyridine, pyrimidine, imidazole, imidazole-derived carbene, and pyrazole.
6. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, aryl, heteroaryl, and combinations thereof.
7. The compound of claim 1 , wherein the fourth distance is longer than the fifth distance by at least 5.9 Å.
8. The compound of claim 1 , wherein at least one of the rings A, B, C, and D is fused by another 5- or 6-membered ring.
9. The compound of claim 1 , wherein each of Q 1 , Q 2 , Q 3 , and Q 4 is a direct bond.
10. The compound of claim 1 , wherein one of Q 1 , Q 2 , Q 3 , and Q 4 is oxygen, the remaining three of Q 1 , Q 2 , Q 3 , and Q 4 are direct bonds.
11. The compound of claim 1 , wherein two of Z 1 , Z 2 , Z 3 , Z 4 are carbon atoms, and the remaining two of Z 1 , Z 2 , Z 3 , Z 4 are nitrogen atoms.
12. The compound of claim 1 , wherein three of Z 1 , Z 2 , Z 3 , Z 4 are carbon atoms, and the remaining one of Z 1 , Z 2 , Z 3 , Z 4 is a nitrogen atom.
13. The compound of claim 1 , wherein the compound has at least one Pt-carbene bond.
14. The compound of claim 1 , wherein the compound is selected from the group consisting of:
15. The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein R 1′ , R 2′ , R 3′ , and R 4′ each represents mono to the maximum possible number of substitution, or no substitution;
wherein R 1′ , R 2′ , R 3′ , and R 4′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two substituents among R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are optionally joined or fused into a ring.
16. The compound of claim 15 , wherein at least one of R 1 and R 1′ and at least one of R 4 and R 4′ is selected from the group consisting of:
17. The compound of claim 1 , wherein the compound is selected from the group consisting of:
18. An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the Formula selected from the group consisting of:
wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein in Formula III:
L 1 and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
n 1 , n 2 each independently is 0 or 1;
when n 1 or n 2 is 1, L 2 or L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof; and
when n 1 or n 2 is 0, L 2 or L 4 is not present;
Q 1 , Q 2 , Q 3 and Q 4 each independently selected from the group consisting of direct bond and oxygen;
when any of Z 1 , Z 2 , Z 3 and Z 4 is nitrogen, the Q 1 , Q 2 , Q 3 and Q 4 attached thereto is a direct bond;
ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
wherein R 1 , R 2 , R 3 , and R 4 each represents mono to the maximum possible number of substitution, or no substitution;
wherein Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from the group consisting of carbon and nitrogen;
wherein M 2 is a metal selected from the group consisting of Pt and Pd;
wherein a fourth distance is the distance between the atom in R 1 that is the farthest away from M 2 to the atom in R 4 that is the farthest away from M 2 ;
wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M 2 to the atom in R 3 that is the farthest away from M 2 ;
wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
wherein R, R′, R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein (i) each of R 1 and R 4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R 1 and R 4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl; and
wherein any two substituents among R, R′, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring.
19. The OLED of claim 18 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
20. A consumer product comprising an organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula selected from the group consisting of:
wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein in Formula III:
L 1 and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
n 1 , n 2 each independently is 0 or 1;
when n 1 or n 2 is 1, L 2 or L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, and combinations thereof; and
when n 1 or n 2 is 0, L 2 or L 4 is not present;
Q 1 , Q 2 , Q 3 and Q 4 each independently selected from the group consisting of direct bond and oxygen;
when any of Z 1 , Z 2 , Z 3 and Z 4 is nitrogen, the Q 1 , Q 2 , Q 3 and Q 4 attached thereto is a direct bond;
ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
wherein R 1 , R 2 , R 3 , and R 4 each represents mono to the maximum possible number of substitution, or no substitution;
wherein Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from the group consisting of carbon and nitrogen;
wherein M 2 is a metal selected from the group consisting of Pt and Pd;
wherein a fourth distance is the distance between the atom in R 1 that is the farthest away from M 2 to the atom in R 4 that is the farthest away from M 2 ;
wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M 2 to the atom in R 3 that is the farthest away from M 2 ;
wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
wherein R, R′, R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein (i) each of R 1 and R 4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R 1 and R 4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl; and
wherein any two substituents among R, R′, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring.