Sulfonate-based compound and polymer electrolyte membrane using same

Patent metadata

Field	Value
Publication number	US-9782767-B2
Application number	US-201414652741-A
Country	US
Kind code	B2
Filing date	Jun 12, 2014
Priority date	Jun 14, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The present specification relates to a sulfonate-based compound and a polymer electrolyte membrane using the same, a membrane electrode assembly including the same, and a fuel cell including the same.

First claim

The invention claimed is:

1. A sulfonate-based compound of the following Formula 1:

wherein:
A1 to A4 are the same as or different from each other, and are each independently a halogen group;
R1 is hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
L is a linking group including one or more of O, S, and SO 2 ;
Z1 to Z4 are each independently a halogen;
R2 is one of the elements of Group 1 of the periodic table;
n is an integer of 0 or more;
m is an integer of 0 or more;
p is an integer of 1 or more; and
{(n×p)+(m×p)} is an integer of 1 to 20, and
wherein the sulfonate-based compound of Formula 1 is a compound of any one of the following Formulae 2-1 to 2-3:

2. The sulfonate-based compound of claim 1 , wherein Z1 to Z4 are each independently selected from the group consisting of F, Cl, Br.

3. A polymer electrolyte membrane comprising the sulfonate-based compound of claim 1 .

4. The polymer electrolyte membrane of claim 3 , wherein the polymer electrolyte membrane further comprises one or more polymers of a perfluorosulfonic acid polymer, a hydrocarbon-based polymer, polyimide, polyvinylidene fluoride, polyethersulfone, polyphenylene sulfide, polyphenylene oxide, polyphosphazine, polyethylene naphthalate, polyester, doped polybenzimidazole, polyether ketone, polysulfone, and acids or bases thereof.

5. A polymer electrolyte membrane comprising a polymer comprising a monomer derived from the sulfonate-based compound of claim 1 .

6. The polymer electrolyte membrane of claim 5 , wherein the polymer electrolyte membrane comprises a block-type copolymer comprising a hydrophilic block and a hydrophobic block.

7. The polymer electrolyte membrane of claim 6 , wherein the hydrophilic block has a weight average molecular weight of 1,000 to 500,000 (g/mol) and the hydrophobic block has a weight average molecular weight of 1,000 to 500,000 (g/mol).

8. The polymer electrolyte membrane of claim 6 , wherein the monomer derived from the sulfonate-based compound is included in a main chain of the hydrophilic block.

9. The polymer electrolyte membrane of claim 5 , wherein ionic conductivity of the polymer electrolyte membrane is 0.03 s/cm to 0.2 s/cm.

10. The polymer electrolyte membrane of claim 5 , wherein an ion exchange capacity value of the polymer electrolyte membrane is 0.5 to 3.

11. The polymer electrolyte membrane of claim 3 , wherein the polymer electrolyte membrane comprises a polymer comprising a repeating unit of the following Formula 3 and a repeating unit of the following Formula 4:

wherein in Formula 3;
a is an integer more than 0;
a′ is an integer of 0 or more;
a:a′=1,000:0 to 5:1; and
l is an integer of 1 to 10,000; and

in Formula 4:
Z is an integer more than 0;
Z′ is an integer of 0 or more;
z:z′=1,000:0 to 5:1; and
l′ is an integer of 1 to 100,000; and

in Formulae 3 and 4:
A, D, and V are the same as or different from each other, and are each independently one of the following Formulae 3-1 to 3-4:

wherein in Formulae 3-1 to 3-4:
X1 is a direct bond, or one of —C(Z5)(Z6)-, —CO—, —O—, —S—, —SO 2 —, and —Si(Z5)(Z6)-;
Z5 and Z6 are the same as or different from each other, and are each independently one of hydrogen, an alkyl group, a trifluoromethyl group (—CF 3 ), and a phenyl group;
S1 and S2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
b and b′ are the same as or different from each other, and are each independently an integer of 0 to 4,
S3 to S6 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
c, c′, d and d′ are the same as or different from each other, and are each independently an integer of 0 to 4;
S7 to S10 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
e, e′, f and f′ are the same as or different from each other, and are each independently an integer of 0 to 4;
S11 is hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or

Assignees

• Lg Chemical Ltd

Inventors

• Yoo Joungeun
• Shin Chong Kyu
• Jeong Seungpyo
• Kim Youngjea
• Lee Jong-Chan

Classifications

• C08J2371/00

  Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers · CPC title

• C08J2371/12

  Polyphenylene oxides · CPC title

• H01M2008/1095

  Fuel cells with polymeric electrolytes · CPC title

• C08J5/2262

  containing fluorine · CPC title

• H01M8/1048

  Ion-conducting additives, e.g. ion-conducting particles, heteropolyacids, metal phosphate or polybenzimidazole with phosphoric acid · CPC title