Composition, polymer thereof, electrode and electrolyte membrane for fuel cell, and fuel cell including the same

Patent metadata

Field	Value
Publication number	US-9680156-B2
Application number	US-201514791588-A
Country	US
Kind code	B2
Filing date	Jul 6, 2015
Priority date	Feb 5, 2010
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

A composition including a compound having a fluorine functional group, a polymer as a polymerization product of the composition, an electrode and an electrolyte membrane for a fuel cell, which include the composition or the polymer thereof, and a fuel cell including at least one of the electrode and the electrolyte membrane.

First claim

What is claimed is:

1. A composition comprising a compound represented by Formula 1, a compound represented by Formula 2, or a compound represented by Formula 1 and a compound represented by Formula 2,
wherein the compound represented by Formula 2 comprises one compound selected from among the compounds represented by Formulae 8, 9, 10 and 11:

wherein, in Formulae 1 and 2, R 1 through R 4 are each independently a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic oxy group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a substituted or unsubstituted C 2 -C 20 heterocyclicoxy group, a halogen atom, a hydroxyl group, or a cyano group,
R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 2 -C 20 alkynylene group, a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, —C(═O)—, —O— and —SO 2 —, and
R 5 and R 5 ′ are each independently —(CF 2 ) n —CF 3 wherein n is an integer from 7 to 15, or the group represented by Formula 3 below, and

wherein, in Formula 3, n is an integer from 5 to 15, and b is an integer from 1 to 5, and
R 7 is identical or different from each other and is selected from among a hydrogen atom, fluorine, a C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 6 -C 20 aryl group, and a fluorinated C 6 -C 20 aryl group,

2. The composition of claim 1 , further comprising a cross-linkable compound.

3. The composition of claim 2 , wherein the cross-linkable compound comprises at least one material selected from the group consisting of a polyazole-based material, polyimide and polyoxazole.

4. The composition of claim 2 , wherein the amount of the cross-linkable compound is in the range of about 5 parts to about 210 parts by weight, based on 100 parts by weight of at least one of the compound of Formula 1 and the compound of Formula 2.

5. The composition of claim 2 , wherein the cross-linkable compound comprises at least one compound selected from the group consisting of the compounds represented by Formulae 12, 13 and 14 below:

wherein, in Formula 12, n 1 is an integer of 10 or greater;

wherein, in Formula 13, n 2 is an integer of 10 or greater;

wherein, in Formula 14, R 9 and R 10 are each independently a hydrogen atom, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 alkoxy group, an unsubstituted or substituted C 6 -C 20 aryl group, an unsubstituted or substituted C 6 -C 20 aryloxy group, an unsubstituted or substituted C 3 -C 20 heteroaryl group, or an unsubstituted or substituted C 3 -C 20 heteroaryloxy group; or R 9 and R 10 may be linked to form a C 4 -C 20 carbocyclic or a C 3 -C 20 hetero ring,
Ar 12 is a substituted or unsubstituted C 6 -C 20 aryl group or a substituted or unsubstituted C 3 -C 20 heteroaryl group,

R 11 through R 13 are each independently a mono- or a multi-substituted substituent selected from the group consisting of a hydrogen atom, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 alkoxy group, an unsubstituted or substituted C 6 -C 20 aryl group, an unsubstituted or substituted C 6 -C 20 aryloxy group, an unsubstituted or substituted C 3 -C 20 heteroaryl group, or an unsubstituted or substituted C 3 -C 20 heteroaryloxy group; or R 1 and R 2 may be linked to form a C 4 -C 20 carbocyclic or a C 3 -C 20 hetero ring,
L represents a linker,
m 1 is a number from 0.01 from 1,
a 1 is 0 or 1,
n 3 is a number from 0 to 0.99, and
k is a number from 10 to 250.

6. An electrode for a fuel cell, the electrode comprising the composition of claim 1 .

7. A fuel cell comprising:
a cathode;
an anode; and
an electrolyte membrane disposed between the cathode and the anode,
wherein at least one of the cathode, the anode and the electrolyte membrane comprises the composition of claim 1 .

8. An electrolyte membrane for a fuel cell, the electrolyte membrane comprising a composition comprising a compound represented by Formula 1, a compound represented by Formula 2, or a compound represented by Formula 1 and a compound represented by Formula 2, wherein the compound represented by Formula 2 comprises one compound selected from among the compounds represented by Formulae 8, 9, 10 and 11:

wherein, in Formulae 1 and 2, R 1 through R 4 are each independently a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic oxy group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a substituted or unsubstituted C 2 -C 20 heterocyclicoxy group, a halogen atom, a hydroxyl group, or a cyano group,
R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 2 -C 20 alkynylene group, a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, —C(═O)—, —O— and —SO 2 —, and
R 5 and R 5 ′ are each independently —(CF 2 ) n —CF 3 wherein n is an integer from 7 to 15, or the group represented by Formula 3 below, and

wherein, in Formula 3, n is an integer from 5 to 15, and b is an integer from 1 to 5, and
R 7 is identical or different from each other and is selected from among a hydrogen atom, fluorine, a C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 6 -C 20 aryl group, and a fluorinated C 6 -C 20 aryl group;

Assignees

• Samsung Electronics Co Ltd
• Samsung Electronics Co Ltd

Inventors

• Choi Seong-Woo
• Park Jung-Ock

Classifications

• Y02E60/521

  Cross-Sectional Technologies · mapped topic

• H01M2300/0082

  Organic polymers · CPC title

• C07D265/16 Primary

  with only hydrogen or carbon atoms directly attached in positions 2 and 4 · CPC title

• H01M8/103

  having nitrogen, e.g. sulfonated polybenzimidazoles [S-PBI], polybenzimidazoles with phosphoric acid, sulfonated polyamides [S-PA] or sulfonated polyphosphazenes [S-PPh] · CPC title

• H01M4/8668

  Binders · CPC title