Process of manufacturing an electron transport material

Patent metadata

Field	Value
Publication number	US-10312448-B2
Application number	US-201615245648-A
Country	US
Kind code	B2
Filing date	Aug 24, 2016
Priority date	Oct 1, 2015
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

A process of dissolving

in a solvent to produce a first mixture. To the first mixture a reagent is added to produce a second mixture. A H—N—R′—R″ is then added to the second mixture to produce a third mixture. The third mixture is then refluxed to produce

First claim

The invention claimed is:

1. A process comprising:
a) dissolving

in a solvent to produce a first mixture;
b) adding a reagent to the first mixture to produce a second mixture;
c) adding a H 2 N—R′-R″ to the second mixture to produce a third mixture; and
d) refluxing the third mixture to produce

wherein throughout the process R is selected from the group consisting of: H, CH 3 , carbonate, SH, F, Cl, Br, I, CN, OH, NH 2 , substituted alkyl chains and unsubstituted alkyl chains; R′ is —(CH 2 ) n —, wherein n is any integer of one or greater; R″ is selected from the group consisting of: NH 2 and OH; and the reagent is capable of cleaving the R group.

2. The process of claim 1 , wherein

is [6,6]-phenyl-C 60 -butyric acid methyl ester.

3. The process of claim 1 , wherein the solvent is an organic solvent.

4. The process of claim 1 , wherein the solvent is selected from the group consisting of: dichlorobenzene, chlorobenzene, xylene, toluene, chloroform, tetrahydronaphthalene, carbon disulfide, dichloromethane, ethyl acetate, ethanol, hexane, cyclohexane, tetrahydrofuran and isopropanol.

5. The process of claim 1 , wherein the reagent is a metal oxide.

6. The process of claim 1 , wherein the reagent is selected from the group consisting of: dibutyltin (IV) oxide, hydrochloric acid, sulfuric acid, nitric acid, acetic acid and combinations thereof.

7. The process of claim 1 , wherein the substitutions for the substituted alkyl chains are selected from the group consisting of: halogens, NH 2 , Br, OH and combinations thereof.

8. The process of claim 1 , wherein

is selected from the group consisting of: [6,6]-phenyl-C 60 -butyric-N-(2-aminoethyl)acetamide, and [6,6]-phenyl-C 60 -butyric-N-(2-hydroxyethyl) acetamide.

9. The process of claim 1 , wherein

is used as an electron transport material in an organic photovoltaic device.

10. A process comprising:
a) dissolving [6,6]-phenyl-C 60 -butyric acid methyl ester in 1,2-dichlorobenzene, under an oxygen free environment, to produce a first mixture;
b) adding dibutyltin(IV) oxide to the first mixture to produce a second mixture;
c) adding ethylenediamine to the second mixture to produce a third mixture; and
d) refluxing the third mixture to produce [6,6]-phenyl-C 60 -butyric-N-(2-aminoethyl)acetamide.

11. A process comprising:
a) dissolving [6,6]-phenyl-C 60 -butyric acid methyl ester in 1,2-dichlorobenzene, under an oxygen free environment, to produce a first mixture;
b) adding dibutyltin(IV) oxide to the first mixture to produce a second mixture;
c) adding 1-ethanol-2-amine to the second mixture to produce a third mixture; and
d) refluxing the third mixture to produce [6,6]-phenyl-C 60 -butyric-N-(2-hydroxyethyl)acetamide.

Assignees

• Phillips 66 Co

Inventors

• Bullock Joseph
• Worfolk Brian

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/4253

  Electricity · mapped topic

• C07C233/22

  having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings · CPC title

• C01B32/152

  Fullerenes · CPC title

• C07C2604/00

  Fullerenes, e.g. C60 buckminsterfullerene or C70 · CPC title