Reactive dendrimers
View Patent ↗A process for modifying at least one dendron that is intended to form part of a dendrimer is disclosed. One reacts at least one reactable unsaturated group in a chemoselective manner to form a less unsaturated group. Also disclosed is a process for modifying dendrimers in a similar manner.
1. A process for modifying at least one dendron intended to form part of a dendrimer, said dendron having the formula:
FO(dendrite−Q a ) y
wherein FO is a functional group attached, either directly or via a linking group which can contain one or more reactable unsaturated units, to the first branching atom or group of the dendrite, each “dendrite” which may be the same or different is a dendrite which contains branching atoms or groups and optionally linking groups and comprises at least said first branching atom or group which must have, in addition to FO, 2 or more groups attached and in which the distal group of each arm of the dendrite is an aryl or heteroaryl group, at least one of said dendrite or, if present, the linking group to FO containing one or more reactable unsaturated units, y is 1 or more, Q is a surface group and a is 0 or an integer, which comprises reacting at least one said reactable unsaturated group in a chemoselective manner to form a less unsaturated group, with the proviso that the process does not comprise hydrogenating a dendron of the formula
where R is 2-ethylhexyloxy.
2. A process for modifying a dendrimer of the formula:
CORE−[dendrite−Q a ] x
wherein Q and a are as defined above, x is one or 2 or more such that when x is more than one each dendrite−Qa can be the same or different and CORE represents an atom or group and CORE terminates at the single bond to the first branching atom or group in the or each “dendrite”, each “dendrite” which may be the same or different and is a dendrite which contains branching atoms or groups and optionally linking groups, at least one of CORE and dendrite comprising at least one reactable unsaturated group, provided that the distal group of each arm of the or each dendrite
is an aryl or heteroaryl group, which comprises reacting at least one reactable unsaturated group to form a less unsaturated group in a chemoselective manner.
3. A process according to claim 2 wherein the reactable unsaturated group becomes fully saturated.
4. A process according to claim 2 wherein only linking groups are reacted.
5. A process according to claim 2 wherein the reactable unsaturated group is a vinylene or acetylenyl group.
6. A process according to claim 2 where the first branching point in the dendrite is a (hetero)aryl group or fused (hetero)aryl group.
7. A process according to claim 6 wherein all the branching points in the dendrite are aryl, heteroaryl or fused (hetero) aryl.
8. A process according to claim 2 wherein the first branching point in the dendrite is a 1,3,5-substituted phenyl group or a 3,6-N-substituted carbazole group.
9. A process according to claim 2 wherein the reactable unsaturated group is part of the core and directly bonded to the first branching group of a dendrite.
10. A process according to claim 2 wherein the dendrimer is asymmetric.
11. A process according to claim 2 wherein the dendrimer is an organometallic dendrimer.
12. A process according to claim 2 wherein the group which has been reacted by a chemoselective reaction is subsequently reacted further.
13. A process according to claim 2 wherein the chemoselective reaction is an addition reaction.
14. A process according to claim 2 wherein the chemoselective reaction is a hydrogenation.
15. A process according to claim 2 wherein the chemoselective reaction involves hydrohalogenation, halogenation, hydrosilylation or hydroboration followed by oxidation.
16. A process according to claim 2 wherein the chemoselective reaction is a cycloaddition.
17. A process according to claim 2 wherein the said reactable unsaturated group is part of a dendrimer that has one at least inherently partially conjugated dendrite.
18. A process according to claim 2 wherein the said reactable unsaturated group is part of a dendrimer that comprises more than one at least inherently conjugated dendrite and the dendrites are attached to at least two ligands complexed to the metal cation which forms part of the core and the chemoselective reaction takes place in the core.
19. A process according to claim 2 wherein the dendrimer has one or more surface groups which allows patterning.
20. A process according to claim 2 wherein the film is capable of emitting visible light.
21. A process for making a dendrimer which involves reacting at least one dendron with a dendrimer precursor wherein the dendron is one which has been modified by a process as claimed in claim 1 .
22. A dendron or dendrimer whenever obtained by a process as claimed in claim 2 .
23. An organic light emitting device comprising, in sequence, layers of a substrate, an electrode, a first optional charge-transporting layer, a light emissive layer, a second optional charge-transporting layer and a counter electrode, wherein at least one of the emissive layer, first optional charge-transporting layer and second optional charge-transporting layers is a film of a dendrimer as claimed in claim 22 .
24. A device according to claim 23 wherein the emissive layer is a film of a dendrimer.
25. A device according to claim 24 which comprises at least one charge-transporting layer.
26. A dendrimer of claim 22 in a photovoltaic device.