Conductive composition and method of preparation, polymer thereof, and electrode, electrolyte membrane and fuel cell including the composition or polymer

A method of preparing a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below, the method comprising thermally treating a mixture of a phenol compound (A) below, formaldehyde, an amine compound (B) below, an aprotic polar solvent and an organic solvent to obtain the at least one of the compounds of Formulae 1 and 2:

• wherein, in Formulae 1 and 2 and in the formulae of the phenol compound (A) and the amine compound (B), R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxy group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• and
• R5 and R5′ are each independently one of the groups represented by Formulae 5A-5C below:
• wherein, in the Formula 5A, a is a number from 1 to 5;
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.

An electrode of a fuel cell, the electrode comprising a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below:

• wherein, in Formulae 1 and 2, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• wherein R5 and R5′ are each independently one of the groups represent by Formulae 5A-5C below:
• wherein, in Formula 5A, a is a number from 1 to 5;
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.

An electrode of a fuel cell, the electrode comprising a polymer that is a polymerization product of a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below:

• wherein, in Formulae 1 and 2, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• and
• wherein R5 and R5′ are each independently one of the groups represent by Formulae 5A-5C below:
• wherein, in Formula 5A, a is a number from 1 to 5;
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.

An electrolyte membrane of a fuel cell, the electrolyte membrane comprising a polymer obtained from polymerization of a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below:

• wherein, in Formulae 1 and 2, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• and
• R5 and R5′ are each independently selected from the group consisting of a group represented by Formula 3 below, a group represented by Formula 4 below, —S≡N, and —C≡CH,
• in Formulae 3 and 4, X1 and X2 are each independently a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C2-C20 heteroarylene group;
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.

A fuel cell comprising:

• a cathode;
• an anode;
• and
• an electrolyte membrane between the cathode and the anode,
• wherein at least one of the cathode, the anode and the electrolyte membrane comprises a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below:
• wherein, in Formulae 1 and 2, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• and
• R5 and R5′ are each independently selected from the group consisting of a group represented by Formula 3 below, a group represented by Formula 4 below, —S≡N, and —C≡CH,
• wherein, in Formulae 3 and 4, X1 and X2 are each independently a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C2-C20 heteroarylene group;
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.

A fuel cell comprising:

• a cathode;
• an anode;
• and
• an electrolyte membrane between the cathode and the anode,
• wherein at least one of the cathode, the anode and the electrolyte membrane comprising a polymer that is a polymerization product of a composition including at least one of a compound represented by Formula 1 below and a compound represented by Formula 2 below:
• wherein, in Formulae 1 and 2, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic oxy group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heteroarylene group, —C(═O)—, and —SO2—;
• R5 and R5′ are each independently selected from the group consisting of a group represented by Formula 3 below, a group represented by Formula 4 below, —S≡N, and —C≡CH,
• wherein, in Formulae 3 and 4, X1 and X2 are each independently a C1-C20 alkylene group, a C6-C20 arylene group, or a C2-C20 heteroarylene group,
• R7 and R8 are each independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, an amino group, or a cyano group;
• and
• m and n are each independently an integer from 0 to 3.