Functionalized polyfluorenes for use in optoelectronic devices
View Patent ↗The present invention relates to process comprising reacting a polyfluorenes comprising at least one structural group of formula I with an iridium (III) compound of formula II wherein R 1 and R 2 are independently alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof; R 5 is H or CHO; R 3 and R 4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof; R 11 and R 12 taken together form a substituted or unsubstituted monocyclic or bicyclic heteroaromatic ring; R 13 is independently at each occurrence halo, nitro, hydroxy, amino, alkyl, aryl, arylalkyl, alkoxy, substituted alkoxy, substituted alkyl, substituted aryl, or substituted arylalkyl; Ar is aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a combination thereof; X is selected from a direct bond, alky, substituted alkyl, and combinations thereof; Y is CHO or NH 2 ; Z is CHO or NH 2 where Z does not equal Y; and p is 0, 1 or 2. The invention also relates to the polyfluorenes, which are products of the reaction, and the use of the polyfluorenes in optoelectronic devices.
1. A process comprising reacting a polyfluorene comprising at least one structural group of formula I
with an iridium (III) compound of formula II
wherein
R 1 and R 2 are independently alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof;
R 5 is H or CHO;
R 3 and R 4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof;
R 11 and R 12 taken together form a substituted or unsubstituted monocyclic or bicyclic heteroaromatic ring;
R 13 is independently at each occurrence halo, nitro, hydroxy, amino, alkyl, aryl, arylalkyl, alkoxy, substituted alkoxy, substituted alkyl, substituted aryl, or substituted arylalkyl;
Ar is aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a combination thereof;
X is a direct bond, alkyl, substituted alkyl, or a combination thereof;
Y is CHO or NH 2 ;
Z is CHO or NH 2 and does not equal Y; and
p is 0, 1 or 2.
2. A process according to claim 1 wherein R 11 and R 12 taken together form a substituted or unsubstituted isoquinoline.
3. A process according to claim 1 wherein X is a direct bond.
4. A process according to claim 1 wherein R 1 is oxaalkyl, substituted oxaalkyl, or a combination thereof.
5. A process according to claim 4 wherein R 1 is
6. A process according to claim 1 further comprising reducing the reaction product of the polyfluorenes of formula I and the iridium (III) compound of formula II.
7. A process according to claim 6 wherein said reducing the reaction product comprises adding NaBH 4 to the reaction product.
8. A process according to claim 1 further comprising reacting the polyfluorenes of formula I with a triarylamine having a primary amino group in addition to the iridium (III) compound of formula II and wherein Z is CHO and Y is NH 2 .
9. A process according to claim 8 further comprising reducing the reaction product of the polyfluorenes of formula I, the iridium (III) compound of formula II, and the triarylamine.
10. A process according to claim 9 wherein the said reducing the reaction product comprises adding NaBH 4 to the reaction product.
11. A process according to claim 8 wherein weight percentage of the iridium (III) compound of formula II relative to the triarylamine ranges from about 0.5 to about 50 mol %.
12. A process according to claim 1 further comprising reacting the polyfluorenes of formula I with a triarylamine having a CHO group in addition to the iridium (III) compound of formula II and wherein Z is NH 2 and Y is CHO.
13. A process according to claim 12 further comprising reducing the reaction product of the polyfluorenes of formula I, the iridium (III) compound of formula II, and the triarylamine.
14. A process according to claim 13 wherein the said reducing the reaction product comprises adding NaBH 4 to the reaction product.
15. A process according to claim 12 wherein weight percentage of the iridium (III) compound of formula II relative to the triarylamine ranges from about 0.5 to about 50 mol %.