Composite membrane for secondary battery, method of preparing the same, and secondary battery including the same

Patent metadata

Field	Value
Publication number	US-10978736-B2
Application number	US-201816224018-A
Country	US
Kind code	B2
Filing date	Dec 18, 2018
Priority date	Apr 20, 2018
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

A composite membrane for a secondary battery, including: a nanostructure including a cross-linked polymer including a repeating unit represented by Formula 1 and a unit derived from a crosslinking compound:

wherein, in Formula 1, Ar 1 , R 1 to R 3 , A,

and Y − are the same as described in the specification.

First claim

What is claimed is:

1. A composite membrane for a secondary battery, the composite membrane comprising:
a nanostructure comprising a cross-linked polymer comprising a repeating unit represented by Formula 1 and a unit derived from a crosslinking compound:

wherein, in Formula 1,
Ar 1 is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group,
R 1 , R 2 , and R 3 are each independently hydrogen, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C6-C20 aryl group, or an unsubstituted or substituted C3-C30 heteroaryl group,
A is a bond, an unsubstituted or substituted C1-C30 alkylene group, an unsubstituted or substituted C6-C30 arylene group, an unsubstituted or substituted C3-C30 heteroarylene group, an unsubstituted or substituted C4-C30 cycloalkylene group, or an unsubstituted or substituted C3-C30 heterocycloalkylene group,

is a 3-membered to 31-membered ring including 2 to 30 carbon atoms,
X is S, N, N(R), or P(R′),
R and R′ are each independently hydrogen, an unsubstituted or substituted C1-C30 alkyl group, an unsubstituted or substituted C1-C30 heteroalkyl group, an unsubstituted or substituted C1-C30 alkoxy group, an unsubstituted or substituted C6-C30 aryl group, an unsubstituted or substituted C7-C30 arylalkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C3-C30 heteroaryl group, an unsubstituted or substituted C4-C30 heteroarylalkyl group, an unsubstituted or substituted C3-C30 cycloalkyl group, an unsubstituted or substituted C2-C30 alkenyl group, or an unsubstituted or substituted C3-C30 alkynyl group, and
Y − is an anion.

2. The composite membrane of claim 1 , wherein the cross-linked polymer is a reaction product of a compound represented by Formula 3, a polymerization product, and then a compound comprising the anion Y − , wherein the polymerization product is a polymerization product of a monomer represented by Formula 2 and the crosslinking compound:

wherein, in Formula 2,
Ar 1 is a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group,
R 1 , R 2 , and R 3 are each independently hydrogen, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C6-C20 aryl group, or an unsubstituted or substituted C3-C30 heteroaryl group,
A is a bond, an unsubstituted or substituted C1-C30 alkylene group, an unsubstituted or substituted C6-C30 arylene group, an unsubstituted or substituted C3-C30 heteroarylene group, an unsubstituted or substituted C4-C30 cycloalkylene group, or an unsubstituted or substituted C3-C30 heterocycloalkylene group,
X 1 is a halogen atom,

wherein, in Formula 3,

is a 3-membered to 31-membered ring including 2 to 30 carbon atoms,
X is S, N, N(R), or P(R′),
R and R′ are each independently hydrogen, an unsubstituted or substituted C1-C30 alkyl group, an unsubstituted or substituted C1-C30 heteroalkyl group, an unsubstituted or substituted C1-C30 alkoxy group, an unsubstituted or substituted C6-C30 aryl group, an unsubstituted or substituted C7-C30 arylalkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C3-C30 heteroaryl group, an unsubstituted or substituted C4-C30 heteroarylalkyl group, an unsubstituted or substituted C3-C30 cycloalkyl group, an unsubstituted or substituted C2-C30 alkenyl group, or an unsubstituted or substituted C3-C30 alkynyl group.

3. The composite membrane of claim 1 , wherein the nanostructure comprises the cross-linked polymer.

4. The composite membrane of claim 1 , wherein the nanostructure comprises a polymeric nanostructure coated with the cross-linked polymer on a surface thereof.

5. The composite membrane of claim 1 , wherein the crosslinking compound comprises 1,2-divinylbenzene, 1,3-divinylbenzene, 1,4-divinylbenzene 1,2,4-trivinylbenzene, 1,3-divinylnaphthalene, 1,8-divinylnaphthalene, 1,3,5-trivinylnaphthalene, 2,4-divinylbiphenyl, 4,4′-divinylbiphenyl, 3,5,7-trivinylnaphthalene, 1,2-divinyl-3,4-dimethylbenzene, 1,5,6-trivinyl-3,7-diethylnaphthalene, 1,3-divinyl-4,5,8-tributylnaphthalene, 2,2′-divinyl-4-ethyl-4′-propylbiphenyl, or a combination thereof.

6. The composite membrane of claim 1 , wherein, the crosslinking compound is CH 2 ═CH—Ar 2 —CH═CH 2 , wherein Ar 2 is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group, and the cross-linked polymer is a polymer represented by Formula 4:

wherein, in Formula 4, Ar 1 , A, R 1 to R 3 ,

X, and Y are the same as defined for Formula 1.

7. The composite membrane of claim 1 , wherein the nanostructure comprises a nanosphere and has a size of about 1 nanometer to about 10 micrometer.

8. The composite membrane of claim 1 , wherein a content of the nanostructure is about 0.5 parts to about 90 parts by weight with respect to 100 parts by weight of the composite membrane.

9. The composite membrane of claim 1 , wherein, in Formula 1, Ar 1 is a phenylene group, a biphenylene group, a naphthalenylene group, a phenanthrenylene group, a triphenylenylene group, an anthracenylene group, a fluorenylene group, or a carbazolylene group.

10. The composite membrane of claim 1 , wherein, in Formula 1, Ar 1 is a group represented by Formula 5-1, Formula 5-2, Formula 5-3, Formula 5-4, or Formula 5-5:

wherein, in Formula 5-1, Formula 5-2, Formula 5-3, Formula 5-4, and Formula 5-5, * indicates a binding site, and R 8 to R 20 are each independently hydrogen, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C6-C20 aryl group, or an unsubstituted or substituted C3-C30 heteroaryl group.

11. The composite membrane of claim 1 , wherein, in Formula 1,

is a group represented by Formula 6-1, Formula 6-2, Formula 6-3, Formula 6-4, or Formula 6a:

wherein, in Formula 6-1, Formula 6-2, Formula 6-3, and Formula 6-4, Z is S, N, or P;
R 11 to R 25 are each independently hydrogen, an unsubstituted or substituted C1-C30 alkyl group, an unsubstituted or substituted C1-C30 alkoxy group, an unsubstituted or substituted C6-C30 aryl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C3-C30 heteroaryl group, an unsubstituted or substituted C3-C30 heteroaryloxy group, an unsubstituted or substituted C4-C30 cycloalkyl group, or an unsubstituted or substituted C3-C30 heterocycloalkyl group; and
R 11 is absent when Z is S, and

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Choi Hongsoo
• Lee Dongjin
• Chang Wonseok
• Im Dongmin

Classifications

• H01M50/443

  Particulate material · CPC title

• H01M50/489

  Separators, membranes, diaphragms or spacing elements inside the cells, characterised by their physical properties, e.g. swelling degree, hydrophilicity or shut down properties · CPC title

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title

• H01M2300/0082

  Organic polymers · CPC title

• H01M4/382

  Lithium (H01M4/405 takes precedence) · CPC title