Non-fullerene acceptors (NFAS) as interfacial layers in perovskite semiconductor devices
A method for producing an organic non-fullerene electron transport compound includes mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in dimethylformamide. The method also includes heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours. The method further includes isolating an organic non-fullerene electron transport compound reaction product.
1. A compound of formula (I);
wherein R is selected from the group consisting of formulas (VI), (VII), (X), or (XI)
2. The compound of claim 1 , where in R has formula (VI).
3. The compound of claim 1 , where in R has formula (VII).
4. The compound of claim 1 , where in R has formula (X).
5. The compound of claim 1 , where in R has formula (XI).
6. A method for producing an organic non-fullerene electron transport compound comprising:
mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in an organic solvent;
heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours; and
isolating an organic non-fullerene electron transport compound reaction product,
wherein the non-fullerene electron transport compound is selected from the group consisting of: formulas (XXIII), (XXV), or (XXVII) or enantiomers of formulas (XXIII), (XXV), or (XXVII)
7. The method of claim 6 , wherein the organic solvent comprises dimethylformamide or imidazole.
8. The method of claim 6 , wherein the amine compound comprises formula (VII) or formula (VIII); and
wherein R is selected from the group consisting of formulas of (XVI), (XVII), and (XVIII);
9. The method of claim 6 , wherein the mixture is heated to a temperature greater than or equal to 100° and less than or equal to 120° C. for an amount of time greater than or equal to 1 hour and less than or equal to 2 hours.
10. The method of claim 6 , wherein isolating the organic non-fullerene electron transport compound reaction product comprises:
cooling the mixture;
introducing an alcohol into the mixture after cooling to precipitate the non-fullerene electron transport compound reaction product;
collecting the precipitated organic non-fullerene electron transport compound reaction product by filtration;
washing the collected organic non-fullerene electron transport compound reaction product with alcohol; and
recrystallizing the washed organic non-fullerene electron transport compound reaction product or isolating the organic non-fullerene electron transport compound reaction product by column chromatography.
11. The method of claim 10 , wherein the alcohol to precipitate or to wash the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof.
12. The method of claim 6 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio.
13. A method for producing an organic non-fullerene electron transport compound comprising:
mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in an organic solvent;
heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours;
cooling the mixture;
introducing an alcohol into the mixture after cooling to precipitate the non-fullerene electron transport compound reaction product;
collecting the precipitated organic non-fullerene electron transport compound reaction product by filtration;
washing the collected organic non-fullerene electron transport compound reaction product with alcohol; and
isolating an organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate by recrystallization or by column chromatography,
wherein the non-fullerene electron transport compound selected from the group consisting of: formulas (XXIII), (XXV), or (XXVII) or enantiomers of formulas (XXIII), (XXV), or (XXVII)
14. The method of claim 13 , wherein the organic solvent comprises dimethylformamide or imidazole.
15. The method of claim 13 , wherein the amine compound comprises formula (VII) or formula (VIII); and
wherein R is selected from the group consisting of formulas of (XVI), (XVII), and (XVIII);
16. The method of claim 13 , wherein the alcohol to precipitate the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof.
17. The method of claim 13 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio.
18. The method of claim 13 , wherein the organic non-fullerene electron transport compound is a compound of formula (XXIII) or an enantiomer of formula (XXIII)
19. The method of claim 13 , wherein the organic non-fullerene electron transport compound is a compound of formula (XXV) or an enantiomer of formula (XXV)
20. The method of claim 13 , wherein the organic non-fullerene electron transport compound is a compound of formula (XXVII) or an enantiomer of formula (XXVII)
21. The method of claim 13 , wherein isolating the organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate comprises recrystallization.
22. The method of claim 13 , wherein isolating the organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate comprises column chromatography.