Functionalized polyfluorenes for use in optoelectronic devices

1. A polyfluorene comprising at least one structural group of formula V

wherein

R 6 is a group of formula VI

R 3 , R 4 and R 7 are independently hydrogen, alkyl, substituted alkyl, aryl substituted aryl, and combinations thereof; and

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;

W is —X′—NH—Y′—, —X′—N═Y″—, —X″═N—Y′—, or a combination thereof;

X′ is selected from a direct bond, alkylene, substituted alkylene, or combinations thereof;

Y′ is alkylene, substituted alkylene, arylene, substituted arylene, oxaalkylene, substituted oxaalkylene, or a combination thereof;

X″ is alkylidene, substituted alkylidene, or a combination thereof;

Y″ is alkylidene, substituted alkylidene, arylidene, substituted arylidene, or a combination thereof, and

p is 0, 1 or 2.

2. A polyfluorene according to claim 1 wherein Y′ is oxaalkylene, substituted oxaalkylene, or a combination thereof.

3. A polyfluorene according to claim 2 wherein Y′ is

4. A polyfluorene according to claim 1 wherein R 11 and R 12 taken together form a substituted or unsubstituted isoquinoline.

5. A polyfluorene according to claim 1 wherein X is a direct bond.

6. A polyfluorene according to claim 1 wherein R 6 additionally comprises at least one triarylamine group.

7. A polyfluorene according to claim 6 wherein the triarylamine group comprises at least one triarylamine substituted secondary amino group, triarylamine substituted imine group, or a combination thereof.

8. A polyfluorenes according to claim 6 wherein weight percentage of the group of formula VI to the triarylamine group is from about 0.5 to about 50 mol %.

9. An organic optoelectronic device comprising a polymer having at least one structural group of formula V

wherein

R 6 is a group of formula VI

R 3 , R 4 and R 7 are independently hydrogen, alkyl, substituted alkyl, aryl substituted aryl, and combinations thereof; and

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;

W is —X′—NH—Y′—, —X′—N═Y″—, —X″═N—Y′—, or a combination thereof;

X′ is selected from a direct bond, alkylene, substituted alkylene, or combinations thereof;

Y′ is alkylene, substituted alkylene, arylene, substituted arylene, oxaalkylene, substituted oxaalkylene, or a combination thereof;

X″ is alkylidene, substituted alkylidene, or a combination thereof;

Y″ is alkylidene, substituted alkylidene, arylidene, substituted arylidene, or a combination thereof, and

p is 0, 1 or 2.

10. An organic optoelectronic device according to claim 9 wherein Y′ is oxaalkylene, substituted oxaalkylene, or a combination thereof.

11. An organic optoelectronic device according to claim 10 wherein Y′ is

12. An organic optoelectronic device according to claim 9 wherein R 11 and R 12 taken together form a substituted or unsubstituted isoquinoline.

13. An organic optoelectronic device according to claim 9 wherein R 6 additionally comprises at least one triarylamine group.

14. An organic optoelectronic device according to claim 13 wherein the triarylamine group is a substituted secondary amino group, triarylamine substituted imine group, or a combination thereof.

15. An organic optoelectronic device according to claim 13 wherein the at least one triarylamine group is a compound of formula VII

wherein

R″ and R′″ are independently hydrogen, alkyl, substituted alkyl, alkenyl, alkynyl, substituted alkenyl, substituted alkynyl, alkyloxy, substituted alkoxy, alkenoxy, alkynoxy, substituted alkenoxy, substituted alkynoxy, taken together a heterocyclic ring or a combination thereof;

Ar 6 and Ar 7 are independently aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a combination thereof;

R′ is an alkyl, substituted alkyl, alkenyl, alkynyl, substituted alkenyl, substituted alkynyl, alkyloxy, substituted alkoxy, alkenoxy, alkynoxy, substituted alkenoxy, substituted alkynoxy, or a combination thereof;

W is —X′—NH—Y′—, —X′—N═Y″—, —X″═N—Y′—, or a combination thereof;

X′ is selected from a direct bond, alkylene, substituted alkylene, or combinations thereof;

Y′ is alkylene, substituted alkylene, arylene, substituted arylene, oxaalkylene, substituted oxaalkylene, or a combination thereof;

X″ is alkylidene, substituted alkylidene, or a combination thereof;

Y″ is alkylidene, substituted alkylidene, arylidene, substituted arylidene, or a combination thereof, and

n is an integer from 0 to 4.

16. An organic optoelectronic device according to claim 15 wherein Y′ is oxaalkylene, substituted oxaalkylene, or a combination thereof.

17. An organic optoelectronic device according to claim 16 wherein Y′ is

18. An organic optoelectronic device according to claim 13 wherein the at least one triarylamine group is a compound of formula VIII

wherein

R′ is an alkyl, substituted alkyl, alkenyl, alkynyl, substituted alkenyl, substituted alkynyl, alkyloxy, substituted alkoxy, alkenoxy, alkynoxy, substituted alkenoxy, substituted alkynoxy, or a combination thereof;

W is —X′—NH—Y′—, —X′—N═Y″—, —X″═N—Y′—, or a combination thereof;

X′ is selected from a direct bond, alkylene, substituted alkylene, or combinations thereof;

Y′ is alkylene, substituted alkylene, arylene, substituted arylene, oxaalkylene, substituted oxaalkylene, or a combination thereof;

X″ is alkylidene, substituted alkylidene, or a combination thereof;

Y″ is alkylidene, substituted alkylidene, arylidene, substituted arylidene, or a combination thereof, and

n is an integer from 0 to 4.

19. An organic optoelectronic device according to claim 18 wherein Y′ is oxaalkylene, substituted oxaalkylene, or a combination thereof.

20. An organic optoelectronic device according to claim 19 wherein Y′ is

21. An organic optoelectronic device according to claim 13 wherein weight percentage of the group of formula VI to the triarylamine group is from about 0.5 to about 50 mol %.

22. An organic optoelectronic device according to claim 9 comprising structural units of formula IX

wherein

R 3 , R 4 and R 7 are independently hydrogen, alkyl, substituted alkyl, aryl substituted aryl, and combinations 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; and

Ar is aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a combination thereof.