# US 2026/0146110 A1 · Fluorinated polyaromatics with linear, branched or crosslinked structure for anion exchange membranes and ionomers

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- Number: US 2026/0146110 A1
- Document ID: US20260146110A1
- Status: Published application
- Kind: A1
- Application number: 19/127,117
- Filed: 2023-11-06
- Published: 2026-05-28
- Earliest claimed: 2022-11-04
- Assignees: Ecole Polytechnique Federale De Lausanne (Epfl)
- Applicants: Ecole Polytechnique Federale De Lausanne (Epfl)
- Inventors: Xile HU; Nanjun CHEN; Xingyu WU
- Web page: https://patentgrep.com/patent/US20260146110A1

## CPC

- C08F 26/06: by a heterocyclic ring containing nitrogen
- C08G 10/00: Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08F 26/02: by a single or double bond to nitrogen
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 5/2262: {containing fluorine}
- C08J 2361/18: Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or their halogen derivatives only
- H01M 8/1039: halogenated, e.g. sulfonated polyvinylidene fluorides
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY

## Abstract

The present specification relates to a fluorinated polyaromatic polymer comprising at least one fluorinated unit FU of formula I and at least one cationic unit CU of formula B or C

## Claims

### Claim 1

A fluorinated polyaromatic polymer comprising
at least one fluorinated unit FU of formula I
wherein
X is C or N,
Y is C,
R1, R2, R5 and R6 are independently selected from
H,
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
wherein at least one of R1, R2, R5 and R6 is
Ra3, Rb4 and Rd7 are independently selected from
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
a and b are independently 0, 1, 2, or 3, particularly 0 or 1, more particularly 0,
d is 0, 1, 2, 3 or 4, particularly 0 or 1, more particularly 0,
n is 0 or 1,
r is, 1, 2, 3, 4, 5 or 6, particularly, 1, 2, or 3, more particularly 1 or 2,
p is independently between 1 and 20, particularly 1 and 15, more particularly 1 and 9, and
q is independently between 0 and 20, particularly 0 and 15, more particularly 0 and 9,
and
at least one cationic unit CU of formula B or C
wherein
R8 is a partially or fully fluorinated C1-C6 alkyl, particularly CF3,
R9 is selected from
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
—(CH2)s—N(R12)2,
—(CH2)s—NHR12,
—(CH2)s—N+(R12)3,
wherein R12 is independently selected from
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
s is between 0 and 20
-Ph-Rf13,
R10 and R11 are independently selected from
H
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
or R10 and R11 are connected to each other to form a cycloalkyl comprising 4 to 10 C atoms,
z is 0 or 1,
A− is an anion.

### Claim 2 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, comprising at least one bifunctional aromatic moiety BA, wherein the BA is independently selected from a moiety comprising 2 to 5, particularly 2 to 3 cyclic hydrocarbon moieties, wherein the BA is unsubstituted or substituted by one or more substituents independently selected from —C1-C10-alkyl, —C1-C10-alkenyl or —C1-C10-alkynyl, wherein the one or more substituent is unsubstituted or further substituted with one or more halogen atoms or one or more quaternary amines.

### Claim 3 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, comprising at least one linear unit LU comprising
the one or more FU and the one or more CU, and/or
the one or more FU, the one or more CU and the one or more BA, particularly
the one or more FU, the one or more CU and the one or more BA,
wherein the LU is arranged [FU-CU]x-[BA-CU]y,
wherein the ratio of x and y is 1:99 to 50:50.

### Claim 4 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein three or more linear units LU form at least one branched unit BU, wherein the three or more linear units LU are connected through at least one branching unit reagent BUR, wherein the at least one BUR is independently selected from a moiety comprising 3 to 6, cyclic hydrocarbon moieties.

### Claim 5 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein two or more linear units LU form at least one crosslinked unit CU, wherein the two or more linear units LU are crosslinked through at least one crosslinker CL, wherein the at least one crosslinker CL is independently selected from an aliphatic or aromatic quaternary diamine.

### Claim 6 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein the at least one fluorinated unit FU is independently selected from
wherein
A is independently selected from —(CH2)p—(CF2)q—CF3,
B, R3 and R4 are independently selected from—
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl, Rd7
C is independently selected from
wherein Rd7 is independently selected from
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
d is 0, 1, 2, 3 or 4,
r is, 1, 2, 3, 4, 5 or 6, particularly 1, 2 or 3, more particularly 1 or 2,
p is independently between 1 and 20, particularly 1 and 15, more particularly 1 and 9, and
q is independently between 0 and 20, particularly 0 and 15, more particularly 0 and 9,
a and b are independently 0, 1, 2, or 3.

### Claim 7 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein the at least one bifunctional aromatic moiety BA is independently selected from
wherein
R14, R15, R16, R17 and R18 are independently selected from
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
l and m are independently 0, 1, 2, 3 or 4,
k is 0 to 4, particularly 1 to 4, more particularly 1 or 2.

### Claim 8 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein the at least one branching unit BU is independently selected from

### Claim 9 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein the at least one crosslinking unit CLU is independently selected from
wherein
Z1 is R19R20 or NR21R22,
Z2 is R19R20 or N+R21R22R23,
R19 and R20 are independently selected from
the group of halogens
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
R21, R22 and R23 are independently selected from
H
—C1-C10 alkyl, wherein the —C1-C10 alkyl is substituted or unsubstituted, particularly —C1-C6 alkyl,
—C2-C10 alkenyl, wherein the —C2-C10 alkenyl is substituted or unsubstituted, particularly —C2-C6 alkenyl,
—C2-C10 alkynyl, wherein the —C2-C10 alkynyl is substituted or unsubstituted, particularly C2-C6 alkynyl,
t is between 0 and 20, particularly 0 to 12, more particularly 0 to 6.

### Claim 10 (depends on 1)

The fluorinated polyaromatic polymer according to claim 1, wherein the fluorine content is 2.5% to 80%, particularly 5% to 60%, more particularly 5 to 30%.

### Claim 11

A method for preparing a fluorinated polyaromatic polymer comprising one or more linear units LU comprising reacting at least one fluorinated unit precursor FUP and optionally at least one cationic unit precursor CUP and optionally at least one bifunctional aromatic moiety precursor BAP.

### Claim 12 (depends on 11)

The method for preparing a fluorinated polyaromatic polymer of claim 11, wherein the fluorinated polyaromatic polymer comprises a branched unit BU comprising three or more linear units LU connected through a branching unit reagent BUR, the method comprising comprising reacting at least one fluorinated unit precursor FUP and optionally at least one cationic unit precursor CUP and optionally at least one bifunctional aromatic moiety precursor BAP and a branching unit precursor BUP.

### Claim 13

A method for preparing a fluorinated polyaromatic polymer comprising a crosslinking unit CU comprising two or more linear units LU connected through one or more crosslinkers CL comprising
reacting at least one fluorinated unit precursor FUP and at least one cationic unit precursor CUP and optionally at least one bifunctional aromatic moiety precursor BAP yielding an intermediate polymer, and
reacting the intermediate polymer with at least one crosslinking unit precursor CLU.