Fluorinated porphyrin derivatives for optoelectronic applications
View Patent ↗Porphyrins and porphyrin derivatives of General Formulas I-V are suitable for use as donor-type materials for photovoltaic cells, absorbers for dye-sensitized solar cells, emitters for red and near infra-red organic light-emitting diodes (OLEDs), absorbers and re-emitters for organic concentrators (e.g., large area organic film for collection of sunlight) for small-size and high efficiency inorganic photovoltaics, and absorbers for hydrogeneration.
1. A complex represented by one of General Formulas I-V:
wherein:
M represents Pt 2+ , Pd 2+ , Zn 2+ , or Mg 2+ ;
each R 1 , R 2 , R 3 , and R 4 independently represents hydrogen, deuterium, halide, nitro, nitrile, hydroxyl, thiol, methyl-d 3 , phenyl-d 5 , amino, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, aryl, or amino;
each R 5 , R 6 , R 7 , and R 8 , when present, independently represents hydrogen, deuterium, fluoride, chloride, nitrile, methyl-d 3 , phenyl-d 5 , or substituted or unsubstituted C 1 -C 4 alkyl or aryl; and
each n is independently an integer, valency permitting;
wherein when the complex is represented by General Formula I, then at least one of the following conditions (i) and (ii) is satisfied:
(i) at least one of R 5 to R 8 is present and represents a substituent selected from the group consisting of chloride, methyl-d3, and phenyl-d5; or
(ii) two occurrences of R 5 are present as fluoride at the 3- and 5-positions.
2. The complex of claim 1 , represented by one of the following structures:
3. The complex of claim 1 , represented by one of the following structures:
4. The complex of claim 1 , represented by one of the following structures.
5. The complex of claim 1 , represented by one of the following structures:
6. The complex of claim 1 , represented by one of the following structures:
7. An optoelectronic device comprising the complex of claim 1 .
8. The optoelectronic device of claim 7 , wherein the optoelectronic device is an organic light-emitting diode.
9. The complex of claim 1 , wherein the complex is represented by General Formula I and at least one of R 5 to R 8 is present and represents a substituent selected from the group consisting of chloride, methyl-d3, and phenyl-d5.
10. The complex of claim 1 , wherein the complex is represented by General Formula I and at least one occurrence of n is 2 and the corresponding substituents are fluoride at the 3- and 5-positions.
11. The complex of claim 1 , wherein the complex is represented by General Formula II, General Formula III, General Formula IV, or General Formula V.