Organic electrolytic solution and lithium battery including the same

Patent metadata

Field	Value
Publication number	US-11127978-B2
Application number	US-201715422873-A
Country	US
Kind code	B2
Filing date	Feb 2, 2017
Priority date	Feb 12, 2016
Publication date	Sep 21, 2021
Grant date	Sep 21, 2021

Abstract

An organic electrolytic solution, including a first lithium salt, an organic solvent, and a bicyclic sulfate-based compound represented by Formula 1 below:wherein, in Formula 1, each of A1, A2, A3, and A4 is independently a covalent bond, a substituted or unsubstituted C1-C5 alkylene group, a carbonyl group, or a sulfinyl group, wherein both A1 and A2 are not a covalent bond and both A3 and A4 are not a covalent bond.

First claim

What is claimed is:

1. An organic electrolytic solution, comprising:
a first lithium salt;
an organic solvent; and
a bicyclic sulfate-based compound represented by Formula 1 or Formula 16 below, wherein an amount of the bicyclic sulfate-based compound is from about 0.01 wt % to about 10 wt % based on a total weight of the organic electrolytic solution:

wherein, 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, provided that A 1 and A 2 are not simultaneously a covalent bond, A 3 and A 4 are not simultaneously a covalent bond, and when A 1 or A 2 is a covalent bond, A 3 or A 4 is a covalent bond, and
wherein at least one of A 1 , A 2 , A 3 , and A 4 is a substituted C 1 -C 5 alkylene group, a carbonyl group, or a sulfinyl group.

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 a substituted C 1 -C 5 alkylene group, and
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:
at least one of A 1 , A 2 , A 3 , and A 4 is a substituted C 1 -C 5 alkylene group, and
the substituted C 1 -C 5 alkylene group is substituted with the polar functional group having at least one heteroatom, wherein the polar functional group is —F, —Cl, —Br, —I, —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 a substituted C 1 -C 5 alkylene group, and
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 is represented by Formula 1, and 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, at least one of E 1 and E 2 being 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:
at least one of B″ 1 , B″ 2 , B″ 3 , and B″ 4 is —C(E 1 )(E 2 )-, at least one of D 1 , and D 2 is —C(E 1 )(E 2 )-, and
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, at least one of E 1 and E2 being 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:
at least one of B″ 1 , B″ 2 , B″ 3 , and B″ 4 is —C(E 1 )(E 2 )-,
at least one of D 1 , and D 2 is —C(E 1 )(E 2 )-, and
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, at least one of E 1 and E 2 being 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 is represented by Formula 1, and the

Assignees

• Samsung Sdi Co Ltd

Inventors

• Son Miyoung
• Woo Myungheui
• Cha Siyoung
• Lee Minju
• Lee Seungtae
• Lee Harim
• Shin Woocheol

Classifications

• C07D497/10

  Spiro-condensed systems · CPC title

• Y02P70/50

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

• H01M10/0525

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

• H01M10/0567 Primary

  characterised by the additives · CPC title

• H01M4/525

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