Polymer compound, solid electrolyte film including the same, and lithium-air battery including the solid electrolyte film

Patent metadata

Field	Value
Publication number	US-11499006-B2
Application number	US-201916441300-A
Country	US
Kind code	B2
Filing date	Jun 14, 2019
Priority date	Jun 14, 2018
Publication date	Nov 15, 2022
Grant date	Nov 15, 2022

Abstract

A polymer compound including a repeating unit represented by Formula:wherein R1, R2, R3, R4, a1, a2, and a11 in Formula 1 are as defined in the specification.

First claim

What is claimed is:

1. A polymer compound comprising a repeating unit represented by Formula 1:

wherein, in Formula 1,
R 1 and R 11 are each independently a single bond or a substituted or unsubstituted C 1 -C 30 alkylene group,
R 2 is a substituted or unsubstituted C 1 -C 10 alkylene group, a substituted or unsubstituted C 2 -C 10 alkenylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 6 -C 10 arylene group, or a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,
R 3 is hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 6 -C 10 aryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
R 4 is hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 6 -C 10 aryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or —N(R 5 )(R 6 ),
R 5 and R 6 are each independently hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 10 aryl group, a substituted or unsubstituted C 6 -C 10 aryloxy group, a substituted or unsubstituted C 6 -C 10 arylthio group, a substituted or unsubstituted C 1 -C 10 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
a1 and a11 are each independently an integer of 1 to 30, wherein, when a1 is 2 or greater, each R 1 is independently the same or different as another R 1 , and when a11 is 2 or greater, each R 11 is independently the same or different as another R 11 , and
a2 is an integer of 1 to 10, wherein, when a2 is 2 or greater, each R 2 is independently the same or different as another R 2 .

2. The polymer compound of claim 1 , wherein one of (R 11 ) a11 or (R 1 ) a1 is a methylene group.

3. The polymer compound of claim 1 , wherein R 2 is a substituted or unsubstituted C 1 -C 10 alkylene group.

4. The polymer compound of claim 1 , wherein R 3 is hydrogen or a substituted or unsubstituted C 1 -C 10 alkyl group.

5. The polymer compound of claim 1 , wherein R 4 is hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, or —N(R 5 )(R 6 ), and
R 5 and R 6 are each independently hydrogen or a substituted or unsubstituted C 1 -C 10 alkyl group.

6. The polymer compound of claim 1 , wherein R 4 is:
a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, or a hexyl group;
a substituted methyl group, a substituted ethyl group, a substituted n-propyl group, a substituted iso-propyl group, a substituted n-butyl group, a substituted sec-butyl group, a substituted iso-butyl group, a substituted tert-butyl group, a substituted pentyl group, or a substituted hexyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, or a hexyl group; or
—N(R 5 )(R 6 ), and
R 5 and R 6 are each independently a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, or a hexyl group.

7. The polymer compound of claim 1 , wherein R 4 is a fluorine-substituted methyl group or —N(R 5 )(R 6 ), and
R 5 and R 6 are each independently hydrogen, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group.

8. The polymer compound of claim 1 , wherein R 4 is —CF 3 or —N(CH 3 ) 2 .

9. The polymer compound of claim 1 , wherein the repeating unit represented by Formula 1 comprises at least one repeating unit represented by Formula 1-1 to Formula 1-4:

wherein, in Formula 1-1 to Formula 1-4, R 1 , R 2 , R 3 , R 13 , R 4 , R 5 , a1, and a2 are defined the same as in claim 1 , and R 11 , R 12 , a11, a12, and R 13 are defined the same as R 1 , R 2 , a1, a2, and R 3 of claim 1 , respectively.

10. The polymer compound of claim 9 , wherein the polymer compound comprises:
(i) the repeating unit represented by Formula 1-1 and the repeating unit represented by Formula 1-2,
(ii) the repeating unit represented by Formula 1-1 and the repeating unit represented by Formula 1-3,
(iii) the repeating unit represented by Formula 1-1 and the repeating unit represented by Formula 1-4,
(iv) the repeating unit represented by Formula 1-2 and the repeating unit represented by Formula 1-3,
(v) the repeating unit represented by Formula 1-2 and the repeating unit represented by Formula 1-4, or
(vi) the repeating unit represented by Formula 1-3 and the repeating unit represented by Formula 1-4.

11. The polymer compound of claim 9 , wherein R 1 and R 11 are each independently a substituted or unsubstituted C 1 -C 30 alkylene group.

12. The polymer compound of claim 9 , wherein R 1 and R 11 are each a hexylene group.

13. The polymer compound of claim 1 , wherein the polymer compound comprises a repeating unit represented by at least one of Formula 2-1 or Formula 2-2:

14. A solid electrolyte film comprising, the polymer compound according to claim 1 .

15. The solid electrolyte film of claim 14 , wherein the solid electrolyte film has an ionic conductivity of greater than or equal to about 4×10 −6 Siemens per centimeter at 60° C.

16. The solid electrolyte film of claim 14 , wherein the solid electrolyte film has an electrochemical window of about 2 volts to about 4.5 volts.

17. A lithium-air battery comprising:
a positive electrode;
a negative electrode; and
a solid electrolyte film between the positive electrode and the negative electrode,
wherein the solid electrolyte film comprises the polymer compound of claim 1 .

18. The lithium-air battery of claim 17 , wherein the solid electrolyte film and the positive electrode are in contact with each other.

19. The lithium-air battery of claim 17 , further comprising an oxygen blocking film between the solid electrolyte film and the negative ele

Assignees

• Samsung Electronics Co Ltd
• Massachusetts Inst Technology

Inventors

• Lee Dongjoon
• Johnson Jeremiah A
• Huang Mingjun
• Feng Shuting
• Zhang Wenxu
• Kwon Hyukjae
• Kim Mokwon
• Kim Taeyoung
• Shao-Horn Yang
• Giordano Livia

Classifications

• C08G2261/418

  Ring opening metathesis polymerisation [ROMP] · CPC title

• H01M2300/0094

  in the form of layered products, e.g. coatings · CPC title

• C08G2261/1452

  containing sulfonyl or sulfonate-groups · CPC title

• C08G2261/3322

  derived from cyclooctene · CPC title

• H01M12/06

  with one metallic and one gaseous electrode · CPC title