Aryl-aryl dendrimers
View Patent ↗Light emitting devices are described which incorporate, as the light emitting element, a dendrimer of which the constituent dendrons include a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring atoms of said aryl or heteroaryl groups.
1. A semiconductor device, which is not a light emitting device, incorporating as an active element at least one compound having the formula (I):
CORE−[DENDRITE(−Q) a ] n (I)
in which CORE represents an atom or group, n represents an integer of at least 1, Q is a proton or a surface group, a is an integer and DENDRITE, which may be the same or different if n is greater than 1, represents a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring atoms of said aryl or heteroaryl groups, CORE terminating in the first single bond which is connected to an sp 2 hybridized ring atom of an aryl group or heteroaryl group to which more than one conjugated dendritic branch is attached, said atom forming part of DENDRITE, at least one of CORE and DENDRITE being luminescent; provided that the compound is not
wherein each Z is a group of formula:
2. A semiconductor device, which is not a light emitting device, incorporating as an active element at least one compound having the formula (II):
CORE−[DENDRITE(−Q) a ] n (II)
in which CORE represents an atom or group other than a nitrogen atom or a group of tetrahedral shape, n represents an integer of at least 1, Q is a proton or a surface group, a is an integer and DENDRITE, which may be the same or different if n is greater than 1, represents a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring atoms of said aryl or heteroaryl groups, CORE terminating in the first single bond which is connected to an sp 2 hybridized ring atom of an aryl group or heteroaryl group to which more than one conjugated dendritic branch is attached, said atom forming part of DENDRITE, at least one of CORE and DENDRITE being luminescent.
3. A semiconductor device according to claim 1 , wherein at least one DENDRITE comprises a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring carbon atoms of said aryl or heteroaryl groups.
4. A semiconductor device according to claim 1 , wherein at least one DENDRITE contains a phenyl branching group linked directly to at least one aryl branching group which is not phenyl.
5. A semiconductor device according to claim 1 , wherein at least one DENDRITE contains a phenyl branching group linked to one or more phenyl branching groups via an aryl linker.
6. A semiconductor device according claim 1 , wherein the active element is deposited by solution processing.
7. A semiconductor device according to claim 1 , herein distal aryl groups of DENDRITE are substituted by one or more Q which are surface groups and which may be the same or different.
8. A semiconductor device according to claim 1 , wherein a HOMO-LUMO energy gap of the active element decreases from distal aryl groups to CORE.
9. A semiconductor device according to claim 1 , wherein CORE is not luminescent.
10. A semiconductor device according to claim 1 , wherein CORE is not luminescent and a HOMO-LUMO energy gap of DENDRITE decreases from distal aryl groups to the attachment point to CORE.
11. A semiconductor device according to claim 1 , wherein the active element is prepared by a convergent route.
12. A semiconductor device according to claim 1 , comprising a layer of said active element together with at least one layer of another material.
13. A semiconductor device according to claim 1 , comprising a film formed of a compound having the formula (I).
14. A semiconductor device according to claim 1 , wherein the compound having the formula (I) is blended with at least one of another dendrimer, a polymer, and a molecular compound.
15. A semiconductor device according to claim 1 , wherein at least one Q is a surface group selected from branched and unbranched alkyl, alkoxy, hydroxy, alkylsilane, carboxy, carbalkoxy, and vinyl; a further-reactable alkene, (meth)acrylate, sulphur-containing, or silicon-containing group; a sulphonyl group; a polyether group; a C 1 to C 15 alkyl group; an amine group; a mono-, di- or tri-C 1 to C 15 alkyl amine group; a —COOR group wherein R is hydrogen or C 1 to C 15 alkyl; an —OR group wherein R is hydrogen, aryl, or C 1 to C 15 alkyl or alkenyl; an —O 2 SR group wherein R is C 1 to C 15 alkyl or alkenyl; an —SR group wherein R is aryl, or C 1 to C 15 alkyl or alkenyl; an —SiR 3 group wherein the R groups are the same or different and are hydrogen, C 1 to C 15 alkyl or alkenyl, or —SR′ group wherein R′ is aryl or C 1 to C 15 alkyl or alkenyl, aryl, and heteroaryl.
16. A semiconductor device according to claim 1 , wherein CORE is at least one moiety selected from the group consisting of benzene, pyridine, pyrimidine, triazine, thiophene, fluorene, divinylbenzene, distyrylethylene, divinylpyridine, divinylthiophene, oxadiazole, coronene, fluorescent dye and marker compounds, and metallic compounds.
17. A method of manufacturing semiconductor device, which is not a light emitting device, comprising the steps of providing a film of at least one compound as defined in claim 1 and, optionally, one or more other films to provide a laminate, adhering to one surface of said film or laminate a substantially transparent electrode, and depositing on another surface of said film or laminate a metallic cathode.
18. A film formed of a compound as defined in claim 1 .
19. A semiconductor device according to claim), wherein the device is a photodiode.
20. A semiconductor device according to claim 1 , wherein the device is a solar cell.
21. A semiconductor device according to claim 1 , wherein the device is a transistor.
22. A semiconductor device according to claim 12 , comprising a layer of said active element together with at least one hole-transporting or electron-transporting layer.
23. A semiconductor device according to claim 16 , wherein CORE is selected from lanthanides, iridium complexes, and metalloporphyrins.
24. A method according to claim 17 , wherein said substantially transparent electrode is ITO.
25. A method according to claim 17 , wherein said metallic cathode comprises Al, Mg/Ag, or Ca.
26. A film according to claim 18 having a thickness of 20 nm to 200 nm.
27. A film according to claim 26 having a thickness of 50 nm to 150 nm.
28. A semiconductor device according to claim), wherein the device is selected from the group consisting of photodiodes, solar cells, FETs, and solid state triodes.
29. A semiconductor device according to claim 2 , wherein at least one DENDRITE comprises a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring carbon atoms of said aryl or heteroaryl groups.
30. A semiconductor device according to claim 2 , wherein at least one DENDRITE contains a phenyl branching group linked directly to at least one aryl branching group which is not phenyl.
31. A semiconductor device according to claim 2 , wherein at least one DENDRITE contains a phenyl branching group linked to one or more phenyl branching groups via an aryl linker.
32. A semiconductor device according to claim 2 , wherein the active element is deposited by solution processing.
33. A semiconductor device according to claim 2 , wherein distal aryl groups of DENDRITE are substituted by one or more Q which are surface groups and which may be the same or different.
34. A semiconductor device according to claim 2 , wherein a HOMO-LUMO energy gap of the active element decreases from distal aryl groups to CORE.
35. A semiconductor device according to claim 2 , wherein CORE is not luminescent.
36. A semiconductor device according to claim 2 , wherein CORE is not luminescent and a HOMO-LUMO energy gap of DENDRITE decreases from distal aryl groups to the attachment point to CORE.
37. A semiconductor device according to claim 2 , wherein the active element is prepared by a convergent route.
38. A semiconductor device according to claim 2 , comprising a layer of said active element together with at least one layer of another material.
39. A semiconductor device according to claim 38 , comprising a layer of said active element together with at least one hole-transporting or electron-transporting layer.
40. A semiconductor device according to claim 2 , comprising a film formed of a compound having the formula (II).
41. A semiconductor device according to claim 2 , wherein the compound having the formula (II) is blended with at least one of another dendrimer, a polymer, and a molecular compound.
42. A semiconductor device according to claim 2 , wherein at least one Q is a surface group selected from branched and unbranched alkyl, alkoxy, hydroxy, alkylsilane, carboxy, carbalkoxy, and vinyl; a further-reactable alkene, (meth)acrylate, sulphur-containing, or silicon-containing group; a sulphonyl group; a polyether group; a C 1 to C 15 alkyl group; an amine group; a mono-, di- or tri-C 1 to C 15 alkyl amine group; a —COOR group wherein R is hydrogen or C 1 to C 15 alkyl; an —OR group wherein R is hydrogen, aryl, or C 1 to C 15 alkyl or alkenyl; an —O 2 SR group wherein R is C 1 to C 15 alkyl or alkenyl; an —SR group wherein R is aryl, or C 1 to C 15 alkyl or alkenyl; an —SiR 3 group wherein the R groups are the same or different and are hydrogen, C 1 to C 15 alkyl or alkenyl, or —SR′ group where R′ is aryl or C 1 to C 15 alkyl or alkenyl, aryl, and heteroaryl.
43. A semiconductor device according to claim 2 , wherein CORE is at least one moiety selected from the group consisting of benzene, pyridine, pyrimidine, triazine, thiophene, fluorene, divinylbenzene, distyrylethylene, divinylpyridine, divinylthiophene, oxadiazole, coronene, fluorescent dye and marker compounds, and metallic compounds.
44. A semiconductor device according to claim 42 , wherein CORE is selected from lanthanides, iridium complexes, and metalloporphyrins.
45. A method of manufacturing a light emitting device comprising the steps of providing a film of at least one compound as defined in claim 2 and, optionally, one or more other films to provide a laminate, adhering to one surface of said film or laminate a substantially transparent electrode, and depositing on another surface of said film or laminate a metallic cathode.
46. A method according to claim 43 , wherein said substantially transparent electrode is ITO.
47. A method according to claim 43 , wherein said metallic cathode comprises Al, Mg/Ag, or Ca.
48. A film formed of a compound as defined in claim 2 .
49. A film according to claim 48 having a thickness of 20 nm to 200 nm.
50. A film according to claim 48 having a thickness of 50 nm to 150 nm.
51. A semiconductor device according to claim 1 , wherein the device is a photodiode.
52. A semiconductor device according to claim 2 , wherein the device is a solar cell.
53. A semiconductor device according to claim 2 , wherein the device is a transistor.
54. A semiconductor device according to claim 2 , wherein the device is selected from the group consisting of photodiodes, solar cells, FETs, and solid state triodes.