2,5-linked polyfluorenes for optoelectronic devices
View Patent ↗Polyfluorene polymers and copolymers having substantial amounts (10-100%) of fluorenes coupled at the 2 and 5 positions of fluorene are useful as active layers in OLED devices where triplet energies >2.10 eV are required.
1. A compound of formula I
wherein R 1 and R 2 are independently at each occurrence C 1-20 hydrocarbyl, C 1-20 hydrocarbyl containing one or more S, N, O, P or Si atoms, C 4-16 hydrocarbyl carbonyloxy, C 4-16 aryl(trialkylsiloxy) or R 1 and R 2 taken together with an intervening carbon atom form a C 5-20 hydrocarbyl ring or a C 4-20 hydrocarbyl ring containing at least one S, N or O heteroatom;
R 3 and R 4 are independently at each occurrence C 1-20 hydrocarbyl, C 1-20 hydrocarbyloxy, C 1-20 thioether, C 1-20 hydrocarbylcarbonyloxy or cyano;
X is independently at each occurrence halo, triflate, —B(OH) 2 , —B(OR) 2 , —BO 2 R, or a combination thereof;
R is alkyl or alkylene; and
a and b are independently 0 or 1.
2. A compound according to claim 1 , wherein X is halo.
3. A compound according to claim 1 , wherein X is bromo.
4. A compound according to claim 1 , wherein X is —B(OH) 2 , —B(OR) 2 , or —BO 2 R.
5. A compound according to claim 1 , wherein R 3 and R 4 are H.
6. A compound according to claim 1 , wherein R 1 and R 2 are alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl.
7. A compound according to claim 1 , wherein R 1 and R 2 are alkoxyphenyl.
8. A compound according to claim 1 , wherein R 1 and R 2 are alkyl.
9. A compound according to claim 1 , of formula
10. A compound according to claim 1 , of formula
11. A compound according to claim 1 , of formula
12. A compound according to claim 1 , of formula
13. A compound according to claim 1 , of formula
14. A compound of formula II
wherein R 1 and R 2 are independently at each occurrence H, C 1-20 hydrocarbyl, C 1-20 hydrocarbyl containing one or more S, N, O, P or Si atoms, C 4-16 hydrocarbyl carbonyloxy, C 4-16 aryl(trialkylsiloxy) or R 1 and R 2 taken together with an intervening carbon atom form a C 5-20 hydrocarbyl ring or a C 4-20 hydrocarbyl ring containing at least one S, N or O heteroatom;
R 3 and R 4 are independently at each occurrence H, C 1-20 hydrocarbyl, C 1-20 hydrocarbyloxy, C 1-20 thioether, C 1-20 hydrocarbylcarbonyloxy or cyano;
one of X and Y is halo or triflate and the other one of X and Y is —B(OH) 2 , —B(OR) 2 , or —BO 2 R;
R is alkyl or alkylene; and
a and b are independently 0 or 1.
15. A compound according to claim 14 , wherein X is halo and Y is —B(OH) 2 , —B(OR) 2 , or —BO 2 R.
16. A compound according to claim 14 , wherein X is —B(OH) 2 , —B(OR) 2 , or —BO 2 R and Y is halo.
17. A compound according to claim 14 , wherein one of X and Y is bromo and the other one of X and Y is —BO 2 R.
18. A compound according to claim 14 , wherein R 3 and R 4 are H.
19. A compound according to claim 14 , wherein R 1 and R 2 are alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl.
20. A compound according to claim 14 , wherein R 1 and R 2 are alkoxyphenyl.
21. A compound according to claim 14 , wherein R 1 and R 2 are alkyl.
22. A compound according to claim 14 , of formula
23. A compound according to claim 14 , of formula