# US 10,312,448 B2 · Process of manufacturing an electron transport material

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- Number: US 10,312,448 B2
- Document ID: US10312448B2
- Status: Granted
- Kind: B2
- Application number: 15/245,648
- Filed: 2016-08-24
- Published: 2017-04-06
- Granted: 2019-06-04
- Earliest claimed: 2015-10-01
- Assignees: Phillips 66 Company
- Applicants: Phillips 66 Company
- Inventors: Joseph Bullock; Brian Worfolk
- Web page: https://patentgrep.com/patent/US10312448B2

## CPC

- C07C 231/02: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- C01B 32/152: Fullerenes
- C01B 32/156: After-treatment
- C07C 233/22: having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 85/215: {comprising substituents, e.g. PCBM}
- C07C 2604/00: Fullerenes, e.g. C60 buckminsterfullerene or C70
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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

## Claims

### Claim 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 H2N—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, CH3, carbonate, SH, F, Cl, Br, I, CN, OH, NH2, substituted alkyl chains and unsubstituted alkyl chains; R′ is —(CH2)n—, wherein n is any integer of one or greater; R″ is selected from the group consisting of: NH2 and OH; and the reagent is capable of cleaving the R group.

### Claim 2 (depends on 1)

The process of claim 1, wherein
is [6,6]-phenyl-C60-butyric acid methyl ester.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

The process of claim 1, wherein the substitutions for the substituted alkyl chains are selected from the group consisting of: halogens, NH2, Br, OH and combinations thereof.

### Claim 8 (depends on 1)

The process of claim 1, wherein
is selected from the group consisting of: [6,6]-phenyl-C60-butyric-N-(2-aminoethyl)acetamide, and [6,6]-phenyl-C60-butyric-N-(2-hydroxyethyl) acetamide.

### Claim 9 (depends on 1)

The process of claim 1, wherein
is used as an electron transport material in an organic photovoltaic device.

### Claim 10

A process comprising:
a) dissolving [6,6]-phenyl-C60-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-C60-butyric-N-(2-aminoethyl)acetamide.

### Claim 11

A process comprising:
a) dissolving [6,6]-phenyl-C60-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-C60-butyric-N-(2-hydroxyethyl)acetamide.