# US 2014/0194581 A1 · Polymer, a method of preparing the same, composite prepared from the polymer, and electrode and composite membrane each including the polymer or the composite

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- Number: US 2014/0194581 A1
- Document ID: US20140194581A1
- Status: Published application
- Kind: A1
- Application number: 14/067,288
- Filed: 2013-10-30
- Published: 2014-07-10
- Earliest claimed: 2013-01-10
- Assignees: Seoul National University R&Db Foundation; Samsung Electronics Co., Ltd.
- Applicants: Seoul National University R&DB Foundation; Samsung Electronics Co., Ltd.
- Inventors: Ki-hyun KIM; Pil-won HEO; Chan-ho PAK; Jong-chan LEE; Kihyun KIM; Sung-kon KIM
- Web page: https://patentgrep.com/patent/US20140194581A1

## CPC

- H01M 8/1027: having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
- C08G 75/23: Polyethersulfones
- C08G 79/04: Phosphorus linked to oxygen or to oxygen and carbon
- H01M 4/622: {being polymers}
- H01M 8/1032: having sulfur, e.g. sulfonated-polyethersulfones [S-PES]
- H01M 8/1034: having phosphorus, e.g. sulfonated polyphosphazenes [S-PPh]
- H01M 2008/1095: {Fuel cells with polymeric electrolytes}
- H01M 2300/0082: Organic polymers
- Y02E 60/10: Energy storage using batteries
- Y02E 60/50: Fuel cells
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A polymer comprising a first repeating unit represented by Formula 1: wherein R1 to R13 and Ar1 in Formula 1 are defined in the specification.

## Claims

### Claim 1

A polymer comprising a first repeating unit represented by Formula 1:
wherein, in Formula 1,
at least one of R1 to R13 is a proton-conducting group, and
the remaining R1 to R13 are each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C2-C40 alkynyl group, a substituted or unsubstituted C6-C40 aryl group, a substituted or unsubstituted C7-C40 arylalkyl group, a substituted or unsubstituted C6-C40 aryloxy group, a substituted or unsubstituted C2-C40 heteroaryl group, a substituted or unsubstituted C3-C40 heteroarylalkyl group, a substituted or unsubstituted C2-C40 heteroaryloxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkyl group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, a substituted or unsubstituted C5-C40 carbocyclic alkyloxy group, a substituted or unsubstituted C2-C40 heterocyclic group, a halogen atom, a hydroxy group, and a cyano group, and
Ar1 is a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C7-C40 arylalkylene group, a substituted or unsubstituted C6-C40 arylene oxy group, a substituted or unsubstituted C7-C40 arylalkylene oxy group, a substituted or unsubstituted C2-C40 heteroarylene group, a substituted or unsubstituted C3-C40 heteroarylalkylene group, a substituted or unsubstituted C2-C40 heteroarylene oxy group, a substituted or unsubstituted C2-C40 heteroarylalkylene oxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkylene group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, or a substituted or unsubstituted C4-C40 carbocyclic alkylene oxy group.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein the proton-conducting group is at least one of —SO2H, —CO2H, or —PO3H.

### Claim 3 (depends on 1)

The polymer of claim 1, wherein Ar1 is an arylene group, or an arylene group comprising a hetero atom.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein Ar1 is a unit represented by Structural Formula 1:
wherein, in Structural Formula 1,
X is —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —CH(CCl3)—, or a group represented by Formula 1a,
wherein, in Structural Formula 1a,
R′ is a hydrogen atom, a C1-C40 alkyl group, a C1-C40 alkoxy group, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C6-C40 aryl group, a C7-C40 arylalkyl group, a C6-C40 aryloxy group, a C2-C40 heteroaryl group, a hydroxy group, a cyano group, or a halogen atom.

### Claim 5 (depends on 1)

The polymer of claim 1, wherein the polymer further comprises
a second repeating unit represented by Formula 2, wherein
the first repeating unit and the second repeating unit each have a mole fraction from about 0.01 to about 0.99, and
a sum of the mole fractions of the first repeating unit and the second repeating unit is equal to 1:
wherein, in Formula 2,
A and Ar2 are each independently a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C7-C40 arylalkylene group, a substituted or unsubstituted C6-C40 arylene oxy group, a substituted or unsubstituted C7-C40 arylalkylene oxy group, a substituted or unsubstituted C2-C40 heteroarylene group, a substituted or unsubstituted C3-C40 heteroarylalkylene group, a substituted or unsubstituted C2-C40 heteroarylene oxy group, a substituted or unsubstituted C2-C40 heteroarylalkylene oxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkylene group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, or a substituted or unsubstituted C4-C40 carbocyclic alkylene oxy group.

### Claim 6 (depends on 5)

The polymer of claim 5, wherein A and Ar2 are each independently an arylene group, or an arylene group comprising a hetero atom.

### Claim 7 (depends on 5)

The polymer of claim 5, wherein A and Ar2 are each independently a unit represented by Structural Formula 2:
wherein in Structural Formula 2
X is —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —P(═O)C6H5—, —S(═O)2—, —CH(CCl3)—, or a group represented by Formula 1a;
wherein, in Structural Formula 1a,
R′ is a hydrogen atom, a C1-C40 alkyl group, a C1-C40 alkoxy group, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C6-C40 aryl group, a C7-C40 arylalkyl group, a C6-C40 aryloxy group, a C2-C40 heteroaryl group, a hydroxy group, a cyano group, or a halogen atom.

### Claim 8 (depends on 1)

The polymer of claim 1, wherein the polymer has a weight average molecular weight from about 5,000 to about 950,000.

### Claim 9 (depends on 1)

The polymer of claim 1, wherein the polymer is represented by Formula 3a, Formula 4a, or f Formula 5a:
wherein, in Formula 3a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000,
wherein, in Formula 4a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1;
n, which is a degree of polymerization, is from about 5 to about 5,000, and
wherein, in Formula 5a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000.

### Claim 10 (depends on 1)

The polymer of claim 1, wherein the polymer is represented by Formulae 6, 7, 7a, or 8:
wherein, in Formula 6,
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000,
wherein, in Formula 7,
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from 5 to 5,000,
wherein, in Formula 7a,
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from 5 to 5,000, and
wherein, in Formula 8,
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from 5 to 5,000.

### Claim 11 (depends on 1)

A composite, which is a polymerization product of a composition comprising the polymer of claim 1 and at least one selected from compounds represented by Formulae 14 to 19:
wherein, in Formula 14,
R1, R2, R3, and 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; and
R5 is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group,
wherein, in Formula 15,
R5′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group; and
R6 is selected from 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, in Formula 16,
A, B, C, D, and E are carbon atoms; or
one or two of A, B, C, D, and E are nitrogen atoms, and the remaining A, B, C, D, and E are carbon atoms,
R7 and R8 are linked to each other to form a ring, wherein the ring is a C6-C10 cycloalkyl group, a C3-C10 heteroaryl group, a fused C3-C10 heteroaryl group, a C3-C10 heterocyclic group, or a fused C3-C10 heterocyclic group,
wherein, in Formula 17,
A′ is a substituted or unsubstituted C1-C20 heterocyclic group, a substituted or unsubstituted C4-C20 cycloalkyl group, or a substituted or unsubstituted C1-C20 alkyl group; and
R9 to R16 are each independently a hydrogen atom, C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, a halogen atom, a cyano group, or a hydroxy group,
wherein, in Formula 18,
R17 and R18 are each independently a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, or a group represented by Formula 8A,
wherein, in Formulae 18 and 18a,
R19 and R19′ are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a halogenated C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19,
at least two groups selected from R20, R21, and R22 are linked to each other to form a group represented by Formula 19a,
the remaining R20, R21, and R22 are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
at least two adjacent groups selected from R23, R24, and R25 are linked to each other to form a group represented by Formula 19a, and
the remaining R23, R24, and R25 are each independently a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19a,
R1′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group, and
* indicates a binding site to at least two adjacent groups of R20, R21, and R22 in Formula 19, and a binding site to at least two adjacent groups of R23, R24, and R25 in Formula 19.

### Claim 12 (depends on 11)

The composite of claim 11, wherein the polymer further comprises a second repeating unit represented by Formula 2, wherein
the first repeating unit and the second repeating unit each have a mole fraction from about 0.01 to about 0.99, and
a sum of the mole fractions of the first repeating unit and the second repeating unit is equal to 1:
wherein, in Formula 2,
A and Ar2 are each independently a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C7-C40 arylalkylene group, a substituted or unsubstituted C6-C40 arylene oxy group, a substituted or unsubstituted C7-C40 arylalkylene oxy group, a substituted or unsubstituted C2-C40 heteroarylene group, a substituted or unsubstituted C3-C40 heteroarylalkylene group, a substituted or unsubstituted C2-C40 heteroarylene oxy group, a substituted or unsubstituted C2-C40 heteroarylalkylene oxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkylene group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, or a substituted or unsubstituted C4-C40 carbocyclic alkylene oxy group.

### Claim 13 (depends on 11)

The composite of claim 11, wherein the polymer is represented by Formula 3a, Formula 4a, or Formula 5a:
wherein, in Formula 3a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000,
wherein, in Formula 4a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000,
wherein, in Formula 5a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000.

### Claim 14 (depends on 1)

An electrode comprising the polymer of claim 1 or a composite that is a polymerization product of a composition comprising the polymer and at least one selected from compounds represented by Formulae 14 to 19:
wherein, in Formula 14,
R1, R2, R3, and 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; and
R5 is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group,
wherein, in Formula 15,
R5′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group; and
R6 is selected from 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, in Formula 16,
A, B, C, D, and E are carbon atoms; or
one or two of A, B, C, D, and E are nitrogen atoms, and the remaining A, B, C, D, and E carbon atoms,
R7 and R8 are linked to each other to form a ring, wherein the ring is a C6-C10 cycloalkyl group, a C3-C10 heteroaryl group, a fused C3-C10 heteroaryl group, a C3-C10 heterocyclic group, or a fused C3-C10 heterocyclic group,
wherein, in Formula 17,
A′ is a substituted or unsubstituted C1-C20 heterocyclic group, a substituted or unsubstituted C4-C20 cycloalkyl group, or a substituted or unsubstituted C1-C20 alkyl group; and
R9 to R16 are each independently a hydrogen atom, C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, a halogen atom, a cyano group, or a hydroxy group,
wherein, in Formula 18,
R17 and R18 are each independently a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, or a group represented by Formula 8A,
wherein, in Formulae 18 and 18a,
R19 and R19′ are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a halogenated C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19,
at least two groups selected from R20, R21, and R22 are linked to each other to form a group represented by Formula 19a,
the remaining R20, R21, and R22 are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
at least two adjacent groups selected from R23, R24, and R25 are linked to each other to form a group represented by Formula 19a, and
the remaining R23, R24, and R25 are each individually a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19a,
R1′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group, and
* indicates a binding site to at least two adjacent groups of R20, R21, and R22 in Formula 19, and a binding site to at least two adjacent groups of R23, R24, and R25 in Formula 19.

### Claim 15 (depends on 14)

The electrode of claim 14, wherein the polymer further comprises
a second repeating unit represented by Formula 2, wherein
the first repeating unit and the second repeating unit each have a mole fraction from about 0.01 to about 0.99, and
a sum of the mole fractions of the first repeating unit and the second repeating unit is equal to 1.
wherein, in Formula 2,
A and Ar2 are each independently a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C7-C40 arylalkylene group, a substituted or unsubstituted C6-C40 arylene oxy group, a substituted or unsubstituted C7-C40 arylalkylene oxy group, a substituted or unsubstituted C2-C40 heteroarylene group, a substituted or unsubstituted C3-C40 heteroarylalkylene group, a substituted or unsubstituted C2-C40 heteroarylene oxy group, a substituted or unsubstituted C2-C40 heteroarylalkylene oxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkylene group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, or a substituted or unsubstituted C4-C40 carbocyclic alkylene oxy group.

### Claim 16 (depends on 14)

The electrode of claim 14, wherein the polymer is represented by Formula 3a, Formula 4a, or Formula 5a:
wherein, in Formula 3a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000,
wherein, in Formula 4a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99, wherein a+b=1;
N, which is a degree of polymerization is from about 5 to about 5,000, and
wherein, in Formula 5a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000.

### Claim 17 (depends on 1)

A composite membrane comprising the polymer of claim 1 or a composite, which is a polymerization product of a composition comprising the polymer and at least one selected from compounds represented by Formulae 14 to 19:
wherein, in Formula 14,
R1, R2, R3, and 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; and
R5 is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group,
wherein, in Formula 15,
R5′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group; and
R6 is selected from 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, in Formula 16,
A, B, C, D, and E are carbon atoms; or
one or two of A, B, C, D, and E are nitrogen atoms, and the remaining A, B, C, D, and E are carbon atoms,
R7 and R8 are linked to each other to form a ring, wherein the ring is a C6-C10 cycloalkyl group, a C3-C10 heteroaryl group, a fused C3-C10 heteroaryl group, a C3-C10 heterocyclic group, or a fused C3-C10 heterocyclic group,
wherein, in Formula 17,
A′ is a substituted or unsubstituted C1-C20 heterocyclic group, a substituted or unsubstituted C4-C20 cycloalkyl group, or a substituted or unsubstituted C1-C20 alkyl group; and
R9 to R16 are each independently a hydrogen atom, C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, a halogen atom, a cyano group, or a hydroxy group,
wherein, in Formula 18,
R17 and R18 are each independently a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, or a group represented by Formula 8A,
wherein, in Formulae 18 and 18a,
R19 and R19′ are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 cycloalkyl group, a halogenated C4-C20 cycloalkyl group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19,
at least two groups selected from R20, R21, and R22 are linked to each other to form a group represented by Formula 19a,
the remaining R20, R21, and R22 are each independently a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
at least two adjacent groups selected from R23, R24, and R25 are linked to each other to form a group represented by Formula 19a, and
the remaining R23, R24, and R25 is each independently a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C6-C20 aryloxy group, a halogenated C6-C20 aryl group, a halogenated C6-C20 aryloxy group, a C1-C20 heteroaryl group, a C1-C20 heteroaryloxy group, a halogenated C1-C20 heteroaryl group, a halogenated C1-C20 heteroaryloxy group, a C4-C20 carbocyclic group, a halogenated C4-C20 carbocyclic group, a C1-C20 heterocyclic group, or a halogenated C1-C20 heterocyclic group,
wherein, in Formula 19a,
R1′ is 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted C2-C20 heteroaryloxy group, a substituted or unsubstituted C2-C20 heteroarylalkyl group, a substituted or unsubstituted C4-C20 carbocyclic group, a substituted or unsubstituted C4-C20 carbocyclic alkyl group, a substituted or unsubstituted C2-C20 heterocyclic group, or a substituted or unsubstituted C2-C20 heterocyclic alkyl group, and
* indicates a binding site to at least two adjacent groups of R20, R21, and R22 in Formula 19, and a binding site to at least two adjacent groups of R23, R24, and R25 in Formula 19.

### Claim 18 (depends on 17)

The composite membrane of claim 17, wherein the polymer further comprises
a second repeating unit represented by Formula 2, wherein
the first repeating unit and the second repeating unit each have a mole fraction from about 0.01 to about 0.99, and
a sum of the mole fractions of the first repeating unit and the second repeating unit is equal to 1.
wherein, in Formula 2,
A and Ar2 are each independently a substituted or unsubstituted C6-C40 arylene group, a substituted or unsubstituted C7-C40 arylalkylene group, a substituted or unsubstituted C6-C40 arylene oxy group, a substituted or unsubstituted C7-C40 arylalkylene oxy group, a substituted or unsubstituted C2-C40 heteroarylene group, a substituted or unsubstituted C3-C40 heteroarylalkylene group, a substituted or unsubstituted C2-C40 heteroarylene oxy group, a substituted or unsubstituted C2-C40 heteroarylalkylene oxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkylene group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, or a substituted or unsubstituted C4-C40 carbocyclic alkylene oxy group.

### Claim 19 (depends on 17)

The composite membrane of claim 17, wherein the polymer is represented by Formula 3a, Formula 4a, or Formula 5a:
wherein, in Formula 3a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization is from about 5 to about 5,000:
wherein, in Formula 4a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99, wherein a+b=1;
N, which is a degree of polymerization, is from about 5 to about 5,000, and
wherein, in Formula 5a,
X is a chemical bond, —CH2—, —C(CF3)2—, —C(═O)—, —C(CCl3)2—, —CH(CF3)—, —S(═O)—, —S(═O)2—, —P(═O)C6H5—, or —CH(CCl3)—;
0.01≦a≦0.99; and
0.01≦b≦0.99,
wherein a+b=1; and
n, which is a degree of polymerization, is from about 5 to about 5,000.