Organic electrolytic solution and lithium battery including the same

Patent metadata

Field	Value
Publication number	US-12597640-B2
Application number	US-202217887636-A
Country	US
Kind code	B2
Filing date	Aug 15, 2022
Priority date	Feb 12, 2016
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

An organic electrolytic solution includes a first lithium salt; an organic solvent; a bicyclic sulfate-based compound represented by Formula 1 below; and a nitrile group-containing compound, wherein the nitrile group-containing compound includes a plurality of nitrile groups:

in Formula 1, each of A 1 , A 2 , A 3 , and A 4 is independently a covalent bond, a substituted or unsubstituted C 1 -C 5 alkylene group, a carbonyl group, or a sulfinyl group, wherein both A 1 and A 2 are not a covalent bond and both A 3 and A 4 are not a covalent bond.

First claim

What is claimed is:

1 . An organic electrolytic solution, comprising:
a first lithium salt; an organic solvent; a bicyclic sulfate-based compound represented by Formula 1 below; and a nitrile group-containing compound, wherein: the nitrile group-containing compound includes a plurality of nitrile groups:

in Formula 1, each of A 1 , A 2 , A 3 , and A 4 is independently a covalent bond, a substituted or unsubstituted C 1 -C 5 alkylene group, a carbonyl group, or a sulfinyl group,
both A 1 and A 2 are not a covalent bond and both A 3 and A 4 are not a covalent bond,
the nitrile group-containing compound is represented by Formula L1 or L2 below:

in Formulae L1 and L2, a is an integer of 0 to 10, each of b, c, and d is independently an integer of 0 to 10, and e is an integer of 1 to 5,
an amount of the bicyclic sulfate-based compound is from about 0.1 wt % to about 5 wt % based on a total weight of the organic electrolytic solution, and
an amount of the nitrile group-containing compound is from about 0.1 wt % to about 5 wt % based on the total weight of the organic electrolytic solution.

2 . The organic electrolytic solution as claimed in claim 1 , wherein at least one of A 1 , A 2 , A 3 , and A 4 is an unsubstituted or substituted C 1 -C 5 alkylene group, wherein a substituent of the substituted C 1 -C 5 alkylene group is a halogen-substituted or unsubstituted C 1 -C 20 alkyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen-substituted or unsubstituted C 3 -C 20 cycloalkenyl group, a halogen-substituted or unsubstituted C 3 -C 20 heterocyclic group, a halogen-substituted or unsubstituted C 6 -C 40 aryl group, a halogen-substituted or unsubstituted C 2 -C 40 heteroaryl group, or a polar functional group having at least one heteroatom.

3 . The organic electrolytic solution as claimed in claim 2 , wherein the substituted C 1 -C 5 alkylene group is substituted with a polar functional group including at least one heteroatom, wherein the polar functional group is —F, —Cl, —Br, —I, —CN, —N═C═S, —(CH 2 CH 2 O) n —R 12 (n is an integer of 1 to 10), —C(═O)OR 16 , —OR 16 , —OC(═O)OR 16 , —R 15 OC(═O)OR 16 , —C(═O)R 16 , —R 15 C(═O)R 16 , —OC(═O)R 16 , —R 15 OC(═O)R 16 , —C(═O)—O—C(═O)R 16 , —R 15 C(═O)—O—C(═O)R 16 , —SR 16 , —R 15 SR 16 , —SSR 16 , —R 15 SSR 16 , —S(═O)R 16 , —R 15 S(═O)R 16 , —R 15 C(═S)R 16 , —R 15 C(═S)SR 16 , —R 15 SO 3 R 16 , —SO 3 R 16 , —NNC(═S)R 16 , —R 15 NNC(═S)R 16 , —R 15 N═C═S, —NCO, —R 15 —NCO, —NO 2 , —R 15 NO 2 , —R 15 SO 2 R 16 , —SO 2 R 16 ,

wherein, in the formulae above, each of R 11 and R 15 is independently a halogen-substituted or unsubstituted C 1 -C 20 alkylene group, a halogen-substituted or unsubstituted C 2 -C 20 alkenylene group, a halogen-substituted or unsubstituted C 2 -C 20 alkynylene group, a halogen-substituted or unsubstituted C 3 -C 12 cycloalkylene group, a halogen-substituted or unsubstituted C 6 -C 40 arylene group, a halogen-substituted or unsubstituted C 2 -C 40 heteroarylene group, a halogen-substituted or unsubstituted C 7 -C 15 alkylarylene group, or a halogen-substituted or unsubstituted C 7 -C 15 aralkylene group; and
each of R 12 , R 13 , R 14 and R 16 is independently hydrogen, a halogen, a halogen-substituted or unsubstituted C 1 -C 20 alkyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen-substituted or unsubstituted C 3 -C 12 cycloalkyl group, a halogen-substituted or unsubstituted C 6 -C 40 aryl group, a halogen-substituted or unsubstituted C 2 -C 40 heteroaryl group, a halogen-substituted or unsubstituted C 7 -C 15 alkylaryl group, a halogen-substituted or unsubstituted C 7 -C 15 trialkylsilyl group, or a halogen-substituted or unsubstituted C 7 -C 15 aralkyl group.

4 . The organic electrolytic solution as claimed in claim 1 , wherein at least one of A 1 , A 2 , A 3 , and A 4 is an unsubstituted or substituted C 1 -C 5 alkylene group, wherein a substituent of the substituted C 1 -C 5 alkylene group is a halogen, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group.

5 . The organic electrolytic solution as claimed in claim 1 , wherein the bicyclic sulfate-based compound represented by Formula 1 is represented by Formula 2 or 3:

wherein, in Formulae 2 and 3, each of B 1 , B 2 , B 3 , B 4 , D 1 , and D 2 is independently —C(E 1 )(E 2 )-, a carbonyl group, or a sulfinyl group; and
each of E 1 and E 2 is independently hydrogen, a halogen, a halogen-substituted or unsubstituted C 1 -C 20 alkyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen-substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen-substituted or unsubstituted C 3 -C 20 cycloalkenyl group, a halogen-substituted or unsubstituted C 3 -C 20 heterocyclic group, a halogen-substituted or unsubstituted C 6 -C 40 aryl group, or a halogen-substituted or unsubstituted C 2 -C 40 heteroaryl group.

6 . The organic electrolytic solution as claimed in claim 5 , wherein each of E 1 and E 2 is independently hydrogen, a halogen, a halogen-substituted or unsubstituted C 1 -C 10 alkyl group, a halogen-substituted or unsubstituted C 6 -C 40 aryl group, or a halogen-substituted or unsubstituted C 2 -C 40 heteroaryl group.

7 . The organic electrolytic solution as claimed in claim 5 , wherein each of E 1 and E 2 is independently hydrogen, fluorine (F), chlorine (Cl), bromine (Br), iodine (I), a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group.

8 . The organic electrolytic solution as claimed in claim 1 , wherein the bicyclic sulfate-based compound represented by Formula 1 is represented by Formula 4 or 5:

wherein, in Formulae 4 and 5, each of R 1 , R 2 , R 3 , R 4 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , and R 28 is independently hydrogen, a halogen, a halogen-substituted or unsubstituted C 1 -C 20 alkyl group, a halogen-substituted or unsubstituted C 6 -C 40 aryl group, or a halogen-substituted or unsubstituted C 2 -C 40 heteroaryl group.

9 . The organic electrolytic solution as claimed in claim 8 , wherein each of R 1 , R 2 , R 3 , R 4 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , and R 28 is independently hydrogen, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group.

10 . The organic electrolytic solution as

Assignees

• Samsung Sdi Co Ltd

Inventors

• Koh Sujeong
• Kim Yunhee
• Lee Seungtae
• Choi Sunjoo
• Cha Siyoung
• Son Miyoung
• Lee Minju
• Lim Jinhyeok
• Seo Jinah
• Lee Harim
• Cho Erang

Classifications

• H01M4/131

  Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx · CPC title

• H01M10/0525

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

• H01M4/525 Primary

  of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy · CPC title

• H01M2004/028

  Positive electrodes · CPC title

• C07D327/10

  two oxygen atoms and one sulfur atom, e.g. cyclic sulfates · CPC title