Photoactive devices including porphyrinoids with coordinating additives

Patent metadata

Field	Value
Publication number	US-9029837-B2
Application number	US-201113271993-A
Country	US
Kind code	B2
Filing date	Oct 12, 2011
Priority date	Oct 12, 2010
Publication date	May 12, 2015
Grant date	May 12, 2015

Abstract

Coordinating additives are included in porphyrinoid-based materials to promote intermolecular organization and improve one or more photoelectric characteristics of the materials. The coordinating additives are selected from fullerene compounds and organic compounds having free electron pairs. Combinations of different coordinating additives can be used to tailor the characteristic properties of such porphyrinoid-based materials, including porphyrin oligomers. Bidentate ligands are one type of coordinating additive that can form coordination bonds with a central metal ion of two different porphyrinoid compounds to promote porphyrinoid alignment and/or pi-stacking. The coordinating additives can shift the absorption spectrum of a photoactive material toward higher wavelengths, increase the external quantum efficiency of the material, or both.

First claim

The invention claimed is:

1. An organic photoactive device, comprising:
a substrate;
first and second electrodes supported by the substrate; and
a donor material and an acceptor material arranged together to form a heterojunction between the first and second electrodes, wherein at least one of the donor or acceptor materials includes a metallated porphyrinoid and at least one coordinating additive.

2. The organic photoactive device of claim 1 , wherein the porphyrinoid comprises a porphyrin or a phthalocyanine or both.

3. The organic photoactive device of claim 1 , wherein the porphyrinoid comprises a covalent porphyrin dimer or trimer.

4. The organic photoactive device of claim 3 , wherein the dimer or trimer further comprises fused aromatic terminal groups.

5. The organic photoactive device of claim 1 , wherein the porphyrinoid is metallated with zinc.

6. The organic photoactive device of claim 1 , wherein the at least one coordinating additive comprises a fullerene compound.

7. The organic photoactive device of claim 6 , wherein the fullerene compound is PCBM.

8. The organic photoactive device of claim 1 , wherein the at least one coordinating additive includes a bidentate ligand.

9. The organic photoactive device of claim 1 , wherein the at least one coordinating additive includes a compound having at least one nitrogen free electron pair.

10. The organic photoactive device of claim 9 , wherein the at least one coordinating additive further includes a fullerene compound.

11. The organic photoactive device of claim 9 , wherein the compound having at least one nitrogen free electron pair is pyrrole, imidazole, pyridine, pyrazine, triazine, pyridine-4-carbonitrile, 4-trifluoromethylpyridine, dimethyl amino pyridine, quinoline, an amine, a naphthyridine, a dipyridyl, or any combination thereof.

12. The organic photoactive device of claim 9 , wherein the compound having at least one nitrogen free electron pair is 4,4′-bipyridyl, 1,4-diaminobenzene, 2,6-naphthyridine, or any combination thereof.

13. The organic photoactive device of claim 1 , wherein the donor material includes the metallated porphyrinoid and the at least one coordinating additive, and the acceptor material comprises a fullerene compound.

14. The organic photoactive device of claim 1 , wherein the heterojunction comprises a bulk heterojunction.

15. The organic photoactive device of claim 1 , wherein the heterojunction comprises a planar-mixed heterojunction.

16. The organic photoactive device of claim 1 , wherein the heterojunction comprises a planar heterojunction formed at an interface between a layer of the donor material and a layer of the acceptor material.

17. The organic photoactive device of claim 16 , wherein the layer of donor material comprises:
a covalent porphyrin dimer or trimer having fused pyrene terminal groups;
PCBM; and
a bidentate ligand.

18. An organic photoresponsive device comprising the photoactive device of claim 1 .

19. An organic light emitting device comprising the photoactive device of claim 1 .

20. A photoactive device, comprising:
a substrate;
first and second electrodes supported by the substrate; and
a fullerene compound and a material arranged together between the electrodes as a heterojunction, said material having a supramolecular structure comprising metal ions coordinated with both macrocyclic ligands and bidentate axial ligands, wherein the axial ligands form coordination bonds with the metal ions of adjacent macrocyclic ligands.

21. The photoactive device of claim 20 , wherein the macrocyclic ligands include porphyrins or phthalocyanines or both.

22. The photoactive device of claim 20 , wherein the macrocyclic ligands include covalent porphyrin oligomers coordinated with a plurality of metal ions.

23. The photoactive device of claim 20 , wherein the coordination bonds each include a nitrogen atom interacting with one of the metal ions.

24. The photoactive device of claim 20 , wherein the axial ligands include diamines, dipyridyls, pyrazine, naphthyridines, or any combination thereof.

25. The photoactive device of claim 20 , wherein the supramolecular structure further comprises fullerene compounds that axially coordinate at least some of the macrocyclic ligands.

26. The photoactive device of claim 20 , wherein said material is formed as a donor layer in surface contact with an acceptor layer comprising the fullerene compound.

27. The photoactive device of claim 26 , wherein the acceptor layer comprises C 60 .

28. A photoactive device including a pair of electrodes with a photoactive material arranged between the electrodes, wherein the photoactive material is modified according to the steps of:
providing a photoactive material comprising a metallated porphyrin dimer or trimer and having a characteristic EQE spectrum with at least one EQE peak when paired with another material to form a heterojunction; and
adding at least one coordinating additive to the material that either shifts the at least one EQE peak toward higher wavelengths or increases a maximum value of the at least one EQE peak, or both.

Assignees

• Forrest Stephen R
• Zimmerman Jeramy
• Yu Eric K
• Thompson Mark E
• Trinh Cong
• Whited Matthew
• Diev Vlacheslav
• Univ Michigan

Inventors

• Forrest Stephen R
• Zimmerman Jeramy
• Yu Eric K
• Thompson Mark E
• Trinh Cong
• Whited Matthew
• Diev Vlacheslav

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/381

  Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc · CPC title

• H01L51/424

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic