Bicarbzole containing compounds for OLEDs
Novel organic compounds comprising a bicarbazole core are provided. In particular, the compound has a 3;3′-bicarbazole core substituted at the 9 th position with at least one of dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene and azadibenzoselenophene. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and improved lifetime.
1. A compound comprising a bicarbazole, wherein the compound has the formula:
wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitutions;
wherein R a , R b , R c , R d , R 1 , and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl;
wherein at least one of R 1 and R 2 has the formula:
wherein A and B are independently 5 or 6 membered carbocyclic or heterocyclic rings;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein X is S, O or Se.
2. The compound of claim 1 , wherein R 1 and R 2 are independently selected from aryl and heteroaryl.
3. The compound of claim 1 , wherein only one of R 1 and R 2 has the formula:
4. The compound of claim 1 , wherein both R 1 and R 2 have the formula:
5. The compound of claim 1 , wherein at least one of R 1 and R 2 has the formula:
wherein R A and R B may represent mono, di, tri, or tetra substitutions;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , and Y 8 are independently selected from nitrogen and carbon.
6. The compound of claim 1 , wherein A and B are independently selected from phenyl and pyridine.
7. The compound of claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of:
wherein R′ 1 and R′ 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl.
8. The compound of claim 1 , wherein the compound has the formula:
wherein R A and R B may represent mono, di, tri, or tetra substitutions;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , and Y 8 are independently selected from nitrogen and carbon.
9. The compound of claim 1 , wherein the compound is selected from the group consisting of:
10. A first device comprising an organic light emitting device further 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 bicarbazole, wherein the compound has the formula:
wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitutions;
wherein R a , R b , R c , R d , R 1 , and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl;
wherein at least one of R 1 and R 2 has the formula:
wherein A and B are independently 5 or 6 membered carbocyclic or heterocyclic rings;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein X is S, O or Se.
11. The device of claim 10 , wherein R 1 and R 2 are independently selected from aryl and heteroaryl.
12. The first device of claim 10 , wherein only one of R 1 and R 2 has the formula:
13. The device of claim 10 , wherein both R 1 and R 2 have the formula:
14. The first device of claim 10 , wherein at least one of R 1 and R 2 has the formula:
wherein R A and R B may represent mono, di, tri, or tetra substitutions;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , and Y 8 are independently selected from nitrogen and carbon.
15. The first device of claim 10 , wherein A and B are independently selected from phenyl and pyridine.
16. The first device of claim 10 , wherein R 1 and R 2 are independently selected from the group consisting of:
wherein R′ 1 and R′ 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl.
17. The first device of claim 10 , wherein the compound has the formula:
wherein R A and R B may represent mono, di, tri, or tetra substitutions;
wherein R A and R B are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , and Y 8 are independently selected from nitrogen and carbon.
18. The first device of claim 10 , wherein the compound is selected from the group consisting of:
19. The first device of claim 10 , wherein the organic layer is a blocking layer and the compound having Formula I is a blocking material.
20. The first device of claim 10 , wherein the organic layer is an emissive layer and the compound having Formula I is a host.
21. The device of claim 20 , wherein the emissive layer further comprises a phosphorescent emissive dopant having the formula:
22. The first device of claim 10 , wherein the first device is a consumer product.
23. The first device of claim 10 , wherein the first device is an organic light emitting device.