Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
Compounds comprising a triphenylene moiety and a benzo- or dibenzo-moiety are provided. In particular, the benzo- or dibenzo-moiety has a fused substituent. These compounds may be used in organic light emitting devices, particularly in combination with yellow, orange and red emitters, to provide devices with improved properties.
1. A compound comprising one of the formulae:
wherein X is S or Se;
wherein R 1 , R 2 , and R a are independently selected from hydrogen, deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R 1 and R 2 represent mono, di, tri or tetra substituents;
wherein at least two substituents of R 1 or R 2 are joined to form a fused ring;
wherein R a represents mono or di substituents which cannot fuse to form a benzo ring; and
wherein L represents a spacer or a direct connection to the benzothiophene, or benzoselenophene moiety with additional fused rings;
wherein R′ 1 , R′ 2 , and R′ 3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R′ 1 , R′ 2 , and R′ 3 may represent mono, di, tri, or tetra substituents.
2. The compound of claim 1 , wherein the at least two substituents of R 1 or R 2 are joined to form a 6-membered carbocyclic or heterocyclic ring.
3. The compound of claim 2 , the at least two substituents of R 1 or R 2 are joined to form a benzene ring.
4. The compound of claim 1 , wherein the compound has the formula:
5. The compound of claim 1 , wherein X is S.
6. The compound of claim 1 , wherein L is a direct connection.
7. The compound of claim 1 , wherein L has the formula:
wherein A, B, C and D are independently selected from the group consisting of:
wherein A, B, C and D are optionally further substituted with R a ;
wherein each of p, q, r and s are 0, 1, 2, 3, or 4; and
wherein p+q+r+s is at least 1.
8. The compound of claim 1 , wherein L is phenyl.
9. The compound of claim 1 , wherein the at least two substituents of R 1 or R 2 that are joined to form fused rings form a ring system selected from the group consisting of:
10. The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein X is S or Se;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R′ 1 , R′ 2 , and R′ 3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R′ 1 , R′ 2 , and R′ 3 may represent mono, di, tri or tetra substituents; and
wherein L is a spacer or a direct linkage.
11. The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein X is S, or Se.
12. 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 one of the formulae:
wherein X is S or Se;
wherein R 1 , R 2 , and R a are independently selected from hydrogen, deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R 1 and R 2 may represent mono, di, tri or tetra substituents;
wherein at least two substituents of R 1 or R 2 are joined to form a fused ring;
wherein R a represents mono or di substituents which cannot fuse to form a benzo ring; and
wherein L represents a spacer or a direct connection to the benzothiophene, or benzoselenophene moiety with additional fused rings;
wherein R′ 1 , R′ 2 , and R′ 3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R′ 1 , R′ 2 and R′ 3 may represent mono, di, tri, or tetra substituents.
13. The first device of claim 12 , wherein the compound is selected from the group consisting of:
wherein X is S or Se;
wherein R 1 , R 2 , and R a are independently selected from hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein each of R 1 and R 2 may represent mono, di, tri or tetra substituents;
wherein at least two substituents of R 1 or R 2 are joined to form a fused ring;
wherein R a represents mono or di substituents which cannot fuse to form a benzo ring; and
wherein L represents a spacer or a direct connection to the benzothiophene, or benzoselenophene moiety with additional fused rings.
14. The first device of claim 12 , wherein the organic layer is an emissive layer and the compound comprising one of Formulae 2-4 is the host.
15. The first device of claim 14 , wherein the organic layer further comprises an emissive compound.
16. The first device of claim 15 , wherein the emissive compound is a transition metal complex having at least one ligand selected from the group consisting of:
wherein each of R′ a , R′ b and R′ c may represent mono, di, tri, or tetra substituents;
wherein each of R′ a , R′ b and R′ c substituent are independently selected from a group consisting of hydrogen, deuterium, alkyl, heteroalkyl, aryl, or heteroaryl; and
wherein two adjacent substituents may form into a ring.
17. The first device of claim 12 , wherein the device comprises a second organic layer that is non-emissive, and the compound comprising Formula I is a non-emissive material in the second organic layer.
18. The first device of claim 12 , wherein the first device is an organic light emitting device.
19. The first device of claim 12 , wherein the first device is a consumer product.