Tetracyanoanthraquinodimethane polymers and use thereof

Patent metadata

Field	Value
Publication number	US-9890230-B2
Application number	US-201515123071-A
Country	US
Kind code	B2
Filing date	Mar 6, 2015
Priority date	Mar 7, 2014
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

Novel tetracyanoanthraquinodimethane polymers and use thereof. The problem addressed was that of providing novel polymers which are preparable with a low level of complexity, with the possibility of controlled influence on the physicochemical properties thereof within wide limits in the course of synthesis, and which are usable as active media in electrical charge storage elements for high storage capacity, long lifetime and stable charging/discharging plateaus. Tetracyanoanthraquinodimethane polymers consisting of an oligomeric or polymeric compound of the general formula I have been found.

First claim

The invention claimed is:

1. A tetracyanoanthraquinodimethane polymer comprising an oligomeric or polymeric compound of formula I:

where
R 1 to R 7 : are each independently hydrogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkylthio groups, haloalkyl groups, haloalkoxy groups, cycloalkyl groups, cycloalkoxy groups, aryl groups, heteroaryl groups, aryloxy groups, aralkyl groups, carboxylic acid groups, sulphonic acid groups, amino groups, monoalkylamino groups, dialkylamino groups, nitro groups, cyano groups, hydroxyl groups, alkylcarbonyl groups, alkenylcarbonyl groups, alkynylcarbonyl groups, carboxylic ester groups, carboxamide groups, sulphonic ester groups, thiol groups, halogen atoms or a combination of these groups or atoms,
X: an organic group of one of the general formulae II-XIV:

wherein
R 8 to R 24 : are each independently hydrogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkylthio groups, haloalkyl groups, haloalkoxy groups, cycloalkyl groups, cycloalkoxy groups, aryl groups, heteroaryl groups, aryloxy groups, aralkyl groups, carboxylic acid groups, sulphonic acid groups, amino groups, monoalkylamino groups, dialkylamino groups, nitro groups, cyano groups, hydroxyl groups, alkylcarbonyl groups, alkenylcarbonyl groups, alkynylcarbonyl groups, carboxylic ester groups, carboxamide groups, sulphonic ester groups, thiol groups, halogen atoms or a combination of these groups or atoms,
R 30 to R 32 : are each independently hydrogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkylthio groups, haloalkyl groups, haloalkoxy groups cycloalkyl groups, cycloalkoxy groups, aryl groups, heteroaryl groups, aryloxy groups, aralkyl groups, carboxylic acid groups, sulphonic acid groups, amino groups, monoalkylamino groups, dialkylamino groups, nitro groups, cyano groups, hydroxyl groups, alkylcarbonyl groups, alkenylcarbonyl groups, alkynylcarbonyl groups, carboxylic ester groups, carboxamide groups, sulphonic ester groups, thiol groups, halogen atoms or a combination of these groups or atoms,
R 30 to R 32 : are each independently hydrogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkylthio groups, haloalkyl groups, haloalkoxy groups, cycloalkyl groups, cycloalkoxy groups, aryl groups, heteroacyl groups, aryloxy groups, aralkyl groups, carboxylic acid groups, sulphonic acid groups, amino groups, monoalkylamino groups, dialkylamino groups, nitro groups, cyano groups, alkylcarbonyl groups, alkenylcarbonyl group, alkynylcarbonyl groups, carboxylic ester groups, carboxamide groups, sulphonic ester groups, halogen atoms or a combination of these groups or atoms,
R 33 to R 35 : are each independently hydrogen atoms, alkyl groups, alkenyl groups, alkoxy groups, alkylthio groups, haloalkyl groups, haloalkoxy groups, cycloalkyl groups, cycloalkoxy group, aryl groups, heteroaryl groups, aryloxy groups, aralkyl groups, carboxylic acid groups, sulphonic acid groups, amino groups monoalkylamino groups, dialkylamino groups, nitro groups, cyano groups, hydroxyl groups, alkylcarbonyl groups, alkenylcarbonyl groups, alkylcarbonyl groups, carboxylic ester groups, carboxamide groups, sulphonic ester groups, thiol groups, halogen atoms or a combination of these groups or atoms,
A: is an oxygen atom, a sulphur atom or an —N(R 29 )— group, where R 29 is a hydrogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkylthio group, haloalkyl group, haloalkoxy group, cycloalkyl group, cycloalkoxy group, aryl group, heteroacyl group, aryloxy group, aralkyl group, carboxylic acid group, sulphonic acid group, nitro group, alkylcarbonyl group, alkenylcarbonyl group, alkynylcarbonyl group, carboxylic ester group, carboxamide group, or sulphonic ester group,
A 1 and A 2 : are each independently a covalent bond, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a haloalkyl group, a haloalkoxy group, a cycloalkyl group, a cycloalkoxy group, an aryl group, a heteroaryl group, an aryloxy group, an aralkyl group, a monoalkylamino group, a dialkylamino group, an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, a carboxylic ester group, a carboxamide group, or a sulphonic ester group,
A 3 and A 4 : are each independently a covalent bond, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkyl group, a cycloalkoxy group, an aryl group, a heteroaryl group, an aryloxy group, an aralkyl group, a dialkylamino group, an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, a carboxylic ester group, a carboxamide group, or a sulphonic ester group,
A 5 and A 6 : are each independently a covalent bond, an alkyl group, an alkenyl group, an alkoxy group, an alkylthio group, a haloalkyl group, a haloalkoxy group, a cycloalkyl group, a cycloalkoxy group, an aryl group, a heteroaryl group, an aryloxy group, an aralkyl group, a monoalkylamino group, a dialkylamino group, an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, a carboxylic ester group, a carboxamide group, a sulphonic ester group,
Ar: is an independently substituted cycloalkyl group, cycloalkoxy group, aryl group, heteroaryl group, aryloxy group, or aralkyl group, and
n: is an integer greater than or equal to 2.

2. The tetracyanoanthraquinodimethane polymer according to claim 1 , wherein at least five of R 1 to R 7 are hydrogen and zero to two of R 1 to R 7 are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen substitutents.

3. The tetracyanoanthraquinodimethane polymer according to claim 1 ,
wherein at least two of the R 8 to R 10 substituents are hydrogen atoms and zero to two of the R 8 to R 10 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein at least two of the R 11 to R 13 substituents are hydrogen atoms and zero to two of the R 11 to R 13 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein R 14 is a hydrogen atom, and/or
wherein at least two of the R 15 to R 17 substituents are hydrogen atoms and zero to two of the R 8 to R 10 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein at least two of the R 18 to R 20 substituents are hydrogen atoms and zero to two of the R 18 to R 20 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein R 21 is a hydrogen atom, and/or
wherein at least two of the R 22 to R 24 substituents are hydrogen atoms and zero to two of the R 22 to R 24 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein at least two of the R 26 to R 28 substituents are hydrogen atoms and zero to two of the R 26 to R 28 substituents are halogen atoms, alkyl groups, alkoxy groups, cyano groups, nitro groups and/or other non-hydrogen atom substituents, and/or
wherein at least two of the R 30 to R 32 substituents are hydrogen atoms and zero to two of the R 30 to R 32 substituents are halogen atoms, alkyl groups, alkoxy gro

Assignees

• Haeupler Bernhard
• Schubert Ulrich
• Wild Andreas
• Evonik Degussa Gmbh

Inventors

• Haeupler Bernhard
• Schubert Ulrich
• Wild Andreas

Classifications

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M4/602

  Polymers · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• C08F112/32 Primary

  containing two or more rings · CPC title

• H01M4/606

  containing aromatic main chain polymers · CPC title