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. An optoelectronic device having a layer comprising a polymer having greater than 10% by weight of structural units derived from a compound of formula I
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 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 device according to claim 1 , wherein X is bromo.
3. A device according to claim 1 , wherein X is —B(OH) 2 , —B(OR) 2 , or —BO 2 R.
4. A device according to claim 1 , wherein R 1 and R 2 are alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl.
5. A device according to claim 1 , wherein the polymer additionally comprises structural units derived from a compound of formula III
6. A device according to claim 1 , wherein the polymer additionally comprises structural units derived from at least one arylene monomer.
7. A device according to claim 6 , wherein the arylene monomer is an aryl compound, a heteroaryl compound or a triarylamine.
8. A device according to claim 6 , wherein the arylene monomer is a triarylamine.
9. A device according to claim 1 , comprising greater than about 50% by weight of said structural units.
10. A device according to claim 1 , comprising greater than about 90% by weight of said structural units.
11. An optoelectronic device having a layer comprising a polymer having greater than 10% by weight of structural units derived from 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.
12. An optoelectronic device according to claim 1 , wherein said layer is light emissive.
13. An optoelectronic device according to claim 1 , additionally comprising at least one additional organic layer.
14. An optoelectronic device according to claim 1 , additionally comprising at least one other organic material.
15. The optoelectronic device according to claim 14 , wherein the other organic material is a polymer.
16. The optoelectronic device according to claim 14 , wherein the other organic material is a small molecule or oligomer.
17. The optoelectronic device according to claim 14 , wherein the other material contains at least one carbon-nitrogen bond.
18. The optoelectronic device according to claim 14 , wherein the other organic material comprises a triarylamine.
19. The optoelectronic device according to claim 14 , wherein the other material contains at least one carbon-sulfur bond.
20. An optoelectronic device according to claim 14 , wherein the other organic material comprises a metallic element.
21. An optoelectronic device according to claim 20 , wherein the metallic element is Ru, Rh, Pd, Ag, Os, Ir, Pt, Au, Cu, or a rare earth lanthanide element.
22. An optoelectronic device according to claim 14 , wherein the other organic material is light emissive.
23. An optoelectronic device according to claim 14 , wherein the other organic material emits light of a blue color.