2-azatriphenylene materials for organic light emitting diodes
Compounds containing 2-azatriphenylene are provided. In particular, compounds containing a 2-azatriphenylene core having an additional aromatic group are provided. The compounds provided may be emissive or non-emissive materials. The compounds may be used in organic light emitting devices, particularly as host materials, hole blocking layer materials, or emitting dopants. Devices comprising 2-azatriphenylene containing compounds may demonstrate improved stability and efficiency.
1. A compound including the structure;
wherein R 1 , R 2 , and R 3 may represent up to tetra substitutions;
wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein at least one of R 1 , R 2 , and R 3 comprises a heteroaryl.
2. The compound of claim 1 , herein the compound has the formula:
and
wherein the compound is not coordinated to a metal.
3. The compound of claim 1 , wherein R 3 is a substitution ortho to the nitrogen.
4. The compound of claim 1 , wherein R 1 comprises a heteroaryl.
5. The compound of claim 1 , wherein R 2 comprises a heteroaryl.
6. The compound of claim 1 , wherein R 3 comprises a heteroaryl.
7. The compound of claim 1 , wherein each of R 1 , R 2 , and R 3 comprises a heteroaryl.
8. A compound comprising a ligand L having a formula selected from the group consisting of:
wherein A is a 5-membered or 6-membered aryl or heteroaryl ring;
wherein R A may represent up to tetra substitutions;
wherein R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 may represent up to tetra substitutions;
wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein the ligand L is coordinated to a metal having an atomic number greater than 40.
9. The compound of claim 8 , wherein the metal is Ir.
10. The compound of claim 9 , wherein the ligand L is included in a homoleptic compound.
11. The compound of claim 9 , wherein the ligand L is included in a heteroleptic compound.
12. The compound of claim 11 , wherein the compound has the formula (L) n (L′) 3-n Ir:
wherein n is 1 or 2;
wherein L′ is selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R A , and Ring A independently have meanings as set forth for Formula II;
wherein R′ 1 and R′ 2 may represent up to tetra substitutions;
wherein R′ 1 and R′ 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein L has a different structure than L′.
13. The compound of claim 8 , wherein the ligand L is selected from the group consisting of:
wherein R 4 and R 5 may represent up to tetra substitutions;
wherein R 6 may represent up to penta substitutions; and
wherein each R 4 , R 5 , and R 6 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
14. The compound of claim 8 , wherein the ligand L is selected from the group consisting of:
15. The compound of claim 8 , wherein the compound is selected from the group consisting of:
wherein R′ 1 , R′ 2 , R 3 ′, and R 6 are independently up to penta substituted, and
wherein R′ 1 , R′ 2 , R 3 ′, and R 6 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
16. The compound of claim 8 , wherein the compound is selected from the group consisting of:
17. A first device comprising an organic light emitting device, comprising:
an anode;
a cathode; and
a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound that includes the structure:
wherein R 1 , R 2 , and R 3 may represent up to tetra substitutions;
wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein at least one of R 1 , R 2 , and R 3 comprises a heteroaryl.
18. The first device of claim 17 , wherein the compound has the formula:
and
wherein the compound is not coordinated to a metal.
19. The first device of claim 17 , wherein the first device is a consumer product.
20. A first device comprising an organic light emitting device, comprising:
an anode;
a cathode; and
a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound comprising
a ligand L having a formula selected from the group consisting of:
wherein A is a 5-membered or 6-membered aryl or heteroaryl ring;
wherein R A may represent up to tetra substitutions;
wherein R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 may represent up to tetra substitutions;
wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein the ligand L is coordinated to a metal having an atomic number greater than 40.
21. The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein R′ 1 , R′ 2 , R′ 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may represent up to tetra substitutions; and
wherein R′ 1 , R′ 2 , R′ 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.