Blue luminescent compounds
View Patent ↗There is provided a compound having Formula I: In the formula: R 1 , R 1a , R 2 , and R 2a are the same or different and are H, D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, or deuterosiloxy, with the proviso that at least one of R 1 and R 1a is heteroaryl or deuterated heteroaryl; R 3 , R 3a , R 4 , R 4a , R 5 , and R 6 are the same or different at each occurrence and are D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, or deuterosiloxy, where adjacent groups selected from R 3 , R 3a , R 4 , and R 4a can be joined together to form a fused ring; R 7 is the same or different at each occurrence and is alkyl, aryl, or deuterated analogs thereof, where two alkyl R 7 groups can be joined together to make a cycloalkyl spiro ring, and where two R 7 phenyl groups can be joined to form a spiro fluorene group; a and b are the same or different and are 0 or 1, with the proviso that a+b≧1; x is an integer of 0-3; y is an integer of 0-4; and z is an integer of 0-5.
1. A compound having Formula I, Formula I-a, Formula I-b, Formula I-c, Formula I-d, Formula II-a, Formula II-c, Formula III, Formula III-a, Formula III-b, Formula III-c, Formula III-d, or Formula III-e:
wherein:
R 1 , R 1a , R 2 , R 2a and R 2b are the same or different at each occurrence and are selected from the group consisting of H, D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, with the proviso that at least one of R 1 and R 1a is heteroaryl or deuterated heteroaryl;
R 3 , R 3a , R 4 , R 4a , R 5 , and R 6 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, wherein adjacent groups selected from R 3 , R 3a , R 4 , and R 4a can be joined together to form a fused ring;
R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl, aryl, and deuterated analogs thereof, where two alkyl R 7 groups can be joined together to make a cycloalkyl spiro ring, and where two R 7 phenyl groups can be joined to form a spiro fluorene group;
R 10 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, where adjacent R 10 groups can be joined together to form a fused ring;
a and b are the same or different and are 0 or 1, with the proviso that a+b≧1;
w1 is an integer of 0-3, with the proviso that when a=1, w1 is 0-2;
x is an integer of 0-3;
x1 is an integer of 0-4, with the proviso that when a=1, x1 is 0-3;
y is an integer of 0-4;
y1 is an integer of 0-5, with the proviso that when b=1, y1 is 0-4;
z is an integer of 0-5; and
z1 is an integer of 0-6, with the proviso that when b=1, z1 is 0-5.
2. The compound of claim 1 having Formula I.
3. The compound of claim 1 having Formula I-a.
4. The compound of claim 1 having Formula I-b.
5. The compound of claim 1 , having Formula I-c.
6. The compound of claim 1 , having Formula I-d.
7. The compound of claim 1 having Formula II-a.
8. The compound of claim 1 having Formula II-c.
9. The compound of claim 1 having Formula III.
10. The compound of claim 1 having Formula III-a.
11. The compound of claim 1 having Formula III-b.
12. The compound of claim 1 having Formula III-c.
13. The compound of claim 1 having Formula III-d.
14. The compound of claim 1 having Formula III-e.
15. The compound of claim 1 , wherein at least one R 1 and R 1a is selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, oxazole, benzoxazole, thiazole, benzothiazole, substituted derivatives thereof, and deuterated analogs thereof.
16. The compound of claim 15 , wherein the carbazole is selected from the group consisting of Cz-1, Cz-2, Cz-3, and deuterated analogs thereof
wherein:
R 8 is the same or different at each occurrence and is selected from the group consisting of alkyl, silyl, aryl, and deuterated analogs thereof;
R 9 is selected from the group consisting of aryl and deuterated aryl; and
* represents the point of attachment.
17. The compound of claim 15 , wherein the dibenzothiophene is selected from the group consisting of DBT-1, DBT-2, and deuterated analogs thereof
wherein:
* represents the point of attachment.
18. The compound of claim 15 , wherein the dibenzofuran is selected from the group consisting of DBF-1, DBF-2, and deuterated analogs thereof
wherein:
* represents the point of attachment.
19. An electronic device comprising at least one photoactive layer, wherein the photoactive layer comprises a compound having Formula I, Formula I-a, Formula I-b, Formula I-c, Formula I-d, Formula II-a, Formula II-c, Formula III, Formula III-a, Formula III-b, Formula III-c, Formula III-d, or Formula III-e:
wherein:
R 1 , R 1a , R 2 , R 2a and R 2b are the same or different at each occurrence and are selected from the group consisting of H, D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, with the proviso that at least one of R 1 and R 1a is heteroaryl or deuterated heteroaryl;
R 3 , R 3a , R 4 , R 4a , R 5 , and R 6 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, wherein adjacent groups selected from R 3 , R 3a , R 4 , and R 4a can be joined together to form a fused ring;
R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl, aryl, and deuterated analogs thereof, where two alkyl R 7 groups can be joined together to make a cycloalkyl spiro ring, and where two R 7 phenyl groups can be joined to form a spiro fluorene group;
R 10 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy, where adjacent R 10 groups can be joined together to form a fused ring;
a and b are the same or different and are 0 or 1, with the proviso that a+b≧1;
w1 is an integer of 0-3, with the proviso that when a=1, w1 is 0-2;
x is an integer of 0-3;
x1 is an integer of 0-4, with the proviso that when a=1, x1 is 0-3;
y is an integer of 0-4;
y1 is an integer of 0-5, with the proviso that when b=1, y1 is 0-4;
z is an integer of 0-5; and
z1 is an integer of 0-6, with the proviso that when b=1, z1 is 0-5.
20. A compound having Formula II or Formula II-b:
wherein:
R 5 and R 6 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy;
R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl, aryl, and deuterated analogs thereof, where two alkyl R 7 groups can be joined together to make a cycloalkyl spiro ring, and where two R 7 phenyl groups can be joined to form a spiro fluorene group;
R 10 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy;
a and b are the same or different and are 0 or 1, with the proviso that a+b≧1;
x is an integer of 0-3;
x1 is an integer of 0-4;
z is an integer of 0-5; and
z1 is an integer of 0-6.
21. An electronic device comprising at least one photoactive layer, wherein the photoactive layer comprises a compound having Formula II or Formula II-b:
wherein:
R 5 and R 6 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy;
R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl, aryl, and deuterated analogs thereof, where two alkyl R 7 groups can be joined together to make a cycloalkyl spiro ring, and where two R 7 phenyl groups can be joined to form a spiro fluorene group;
R 10 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, silyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuteroalkoxy, deuteroaryloxy, deuterofluoroalkoxy, deuterosiloxane, and deuterosiloxy;
a and b are the same or different and are 0 or 1, with the proviso that a+b≧1,
x is an integer of 0-3;
x1 is an integer of 0-4;
z is an integer of 0-5; and
z1 is an integer of 0-6.