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 comprising:
a compound of formula (I);
wherein R is selected from the group consisting of formulas (II), (III), (IV), (V), (VIII), or (IX),
2 . The composition of claim 1 , wherein R has formula (II)
3 . The composition of claim 1 , wherein R has formula (III).
4 . The composition of claim 1 , wherein R has formula (IV).
5 . The composition of claim 1 , wherein R has formula (V).
6 . The composition of claim 1 , wherein R has formula (VIII).
7 . The composition of claim 1 , wherein R has formula (IX).
8 . 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.
9 . The method of claim 8 , wherein the organic solvent comprises dimethylformamide or imidazole.
10 . The method of claim 8 , wherein the amine compound comprises formula (VII); and
wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVI), and (XVIII);
11 . The method of claim 8 , wherein the amine compound comprises formula (VIII); and
wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVII), and (XVIII);
12 . The method of claim 8 , 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.
13 . The method of claim 8 , 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.
14 . The method of claim 13 , wherein the alcohol to precipitate or to wash the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof.
15 . The method of claim 8 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio.
16 . 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.
17 . The method of claim 16 , wherein the organic solvent comprises dimethylformamide or imidazole.
18 . The method of claim 16 , wherein the amine compound comprises formula (VII) or formula (VIII); and
wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVII), and (XVIII);
19 . The method of claim 16 , wherein the alcohol to precipitate the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof.
20 . The method of claim 16 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio.
21 . The method of claim 16 , 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 16 , 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.
23 . The method of claim 16 , wherein the organic non-fullerene electron transport compound comprises a compound of formula (XIX) or an enantiomer of formula (XIX)
24 . The method of claim 16 , wherein the organic non-fullerene electron transport compound comprises a compound of formula (XXI) or an enantiomer of formula (XXI)