Oligomer additive and lithium battery
US-2017210855-A1 · Jul 27, 2017 · US
US11264644B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11264644-B2 |
| Application number | US-201816135342-A |
| Country | US |
| Kind code | B2 |
| Filing date | Sep 19, 2018 |
| Priority date | Feb 12, 2016 |
| Publication date | Mar 1, 2022 |
| Grant date | Mar 1, 2022 |
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A lithium battery includes a cathode including a cathode active material, an anode including an anode active material, and an organic electrolytic solution between the cathode and the anode. The organic electrolytic solution includes a first lithium salt, a second lithium salt different from the 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.
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What is claimed is: 1. A lithium battery, comprising: a cathode including a cathode active material; an anode including an anode active material; and an organic electrolytic solution between the cathode and the anode, wherein the organic electrolytic solution includes a first lithium salt, a second lithium salt different from the first lithium salt, an organic solvent, and about 0.4 wt % to about 5 wt % of a bicyclic sulfate-based compound represented by Formula 1 below, 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 and provided that A 3 and A 4 are not simultaneously a covalent bond, wherein the first lithium salt in the organic electrolytic solution consists of LiPF 6 , or consists of LiPF 6 and LiBF 4 , LiSbF 6 , LiAsF 6 , LiClO 4 , LiCF 3 SO 3 , LiC 4 F 9 SO 3 , LiAlO 2 , LiAlCl 4 , LiCl, or LiI, wherein the second lithium salt includes a compound represented by Formula 19, below: and wherein an amount of the second lithium salt is from about 0.1 wt % to about 3 wt % based on a total weight of the organic electrolytic solution. 2. The lithium battery as claimed in claim 1 , wherein: the first lithium salt consists of LiPF 6 . 3. The lithium battery 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. 4. The lithium battery as claimed in claim 3 , 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, —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. 5. The lithium battery 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. 6. The lithium battery 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. 7. The lithium battery as claimed in claim 6 , 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. 8. The lithium battery as claimed in claim 6 , 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. 9. The lithium battery 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. 10. The lithium battery as claimed in claim 9 , 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. 11. The lithium ba
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