Anion exchange resin, electrolyte membrane, binder for forming electrode catalyst layer, fuel cell electrode catalyst layer and fuel cell
Provided are an anion exchange resin being capable of producing an electrolyte membrane, a binder for forming an electrode catalyst layer and a battery electrode catalyst layer, which have improved electrical properties and chemical properties. For example, used is an anion exchange resin which has a hydrophobic unit being composed of bisphenol AF residues repeated via carbon-carbon bond and a hydrophilic unit being composed of hydrophilic groups repeated via carbon-carbon bond, in which the hydrophilic group is formed by connecting an anion exchange group to a fluorene backbone via a divalent saturated hydrocarbon group, and in which the hydrophobic unit and the hydrophilic unit are connected via carbon-carbon bond.
1. An anion exchange resin, comprising:
a divalent hydrophobic group as shown in the following formula (1); and
a divalent hydrophilic group being composed of one aromatic ring, or being composed of a plurality of aromatic rings which are connected to each other via a linking group and/or carbon-carbon bond, wherein the linking group is a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, or a divalent sulfur-containing group, and at least one of the linking group or aromatic ring is connected to an anion exchange group-containing group;
wherein the anion exchange resin comprises a hydrophobic unit being composed of the hydrophobic group alone, or being composed of a plurality of the hydrophobic groups repeated via ether bond, thioether bond, or carbon-carbon bond;
wherein the anion exchange resin comprises a hydrophilic unit being composed of the hydrophilic group alone, or being composed of a plurality of the hydrophilic groups repeated via ether bond, thioether bond, or carbon-carbon bond; and
wherein the hydrophobic unit and the hydrophilic unit are connected via ether bond, thioether bond, or carbon-carbon bond;
(In the formula, each X is the same or different and represents a halogen atom, a pseudohalide, or hydrogen atom; each Y is the same or different and represents an oxygen-containing group, a sulfur-containing group, or direct bond; each Z is the same or different and represents carbon atom or silicon atom; each R is the same or different and represents an aromatic group or direct bond; h, h′, h″, i, i′, and i″ are the same or different and represent an integer of 0 or more; and h′″ and i′″ represent an integer of 1 or more).
2. The anion exchange resin according to claim 1 , wherein, in the above formula (1), each X is the same or different and represents a halogen atom or a pseudohalide and each R is the same or different and represents an aromatic group.
3. The anion exchange resin according to claim 2 , wherein the divalent hydrophobic group is shown in the following formula (1a).
4. The anion exchange resin according to claim 1 , wherein the divalent hydrophilic group is composed of one polycyclic compound, or is composed of a plurality of polycyclic compounds which are connected to each other via a linking group and/or carbon-carbon bond, wherein the linking group is a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, or a divalent sulfur-containing group, and wherein at least one of the linking group or the polycyclic compound is connected to an anion exchange group via a divalent saturated hydrocarbon group having a carbon number of 2 or more.
5. The anion exchange resin according to claim 2 , wherein the divalent hydrophilic group is composed of one polycyclic compound, or is composed of a plurality of polycyclic compounds which are connected to each other via a linking group and/or carbon-carbon bond, wherein the linking group is a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, or a divalent sulfur-containing group, and wherein at least one of the linking group or the polycyclic compound is connected to an anion exchange group via a divalent saturated hydrocarbon group having a carbon number of 2 or more.
6. The anion exchange resin according to claim 3 , wherein the divalent hydrophilic group is composed of one polycyclic compound, or is composed of a plurality of polycyclic compounds which are connected to each other via a linking group and/or carbon-carbon bond, wherein the linking group is a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, or a divalent sulfur-containing group, and wherein at least one of the linking group or the polycyclic compound is connected to an anion exchange group via a divalent saturated hydrocarbon group having a carbon number of 2 or more.
7. The anion exchange resin according to claim 4 , wherein the divalent hydrophilic group is a fluorene residue, as shown in the following formula (2);
(In the formula, each A is the same or different and represents an anion exchange group-containing group, or represents an anion exchange group-containing cyclic structure).
8. The anion exchange resin according to claim 5 , wherein the divalent hydrophilic group is a fluorene residue, as shown in the following formula (2);
(In the formula, each A is the same or different and represents an anion exchange group-containing group, or represents an anion exchange group-containing cyclic structure).
9. The anion exchange resin according to claim 6 , wherein the divalent hydrophilic group is a fluorene residue, as shown in the following formula (2);
(In the formula, each A is the same or different and represents an anion exchange group-containing group, or represents an anion exchange group-containing cyclic structure.
10. An electrolyte membrane, comprising the anion exchange resin according to claim 1 .
11. A binder for forming an electrode catalyst layer, comprising the anion exchange resin according to claim 1 .
12. A fuel cell electrode catalyst layer, comprising the binder for forming an electrode catalyst layer according to claim 11 .