Tert-butylphenyl sulfonate compound, nonaqueous electrolyte solution for lithium secondary battery using the same, and lithium secondary battery using the same
View Patent ↗The disclosed subject matter relate to a di-tert-butylphenyl alkylsulfonate compound, tert-butylphenyl alkylsulfonate compound, di-tert-butylphenyl arylsulfonate compound or tert-butylphenyl arylsulfonate compound useful as an intermediate raw material of a pharmaceutical, agricultural chemical, electronic material or polymer material and the like, or as a battery material, and also provides a nonaqueous electrolytic solution for a lithium secondary battery having superior cycle performance and other battery properties through the use thereof, and a lithium secondary battery. The disclosed embodiments further relate to a nonaqueous electrolytic solution for use as in a lithium secondary battery containing, in a nonaqueous electrolytic solution in which an electrolyte salt is dissolved in a nonaqueous solvent, 0.01 to 10% by weight of a di-tert-butylphenyl alkylsulfonate compound, tert-butylphenyl alkylsulfonate compound, di-tert-butylphenyl arylsulfonate compound or tert-butylphenyl arylsulfonate compound, and to a lithium secondary battery and a compound.
1. A tert-butylphenyl alkylsulfonate compound or tert-butylphenyl arylsulfonate compound represented by general formula (I):
[C1]
(wherein, R 1 represents (i) a fluoro-substituted alkyl group, (ii) a non-substituted alkyl group or (iii) a substituted or non-substituted phenyl group, and n represents an integer of 1 to 2, provided that in the case n=1, the substitution position of the t Bu group is the 2 position or 3 position, in the case the substitution position of the t Bu group is the 2 position, R 1 represents a non-substituted alkyl group having 2 to 4 carbon atoms, in the case the substitution position of the t Bu group is the 3 position, R 1 represents a non-substituted alkyl group having 1 to 4 carbon atoms, and in the case n=2, the substitution positions of the t Bu group are any of the 2,4 position, 2,5 position, 2,6 position or 3,5 position, and in the case t Bu groups are present at the 3,5 position, R 1 represents a non-substituted alkyl group having 1 to 4 carbon atoms or a non-substituted phenyl group).
2. The tert-butylphenyl alkylsulfonate compound or the tert-butylphenyl arylsulfonate compound according to claim 1 , wherein the compound represented by the general formula (I) is one type of compound selected from 2,4-di-tert-butylphenyl methanesulfonate, 2,6-di-tert-butylphenyl methanesulfonate, 3,5-di-tert-butylphenyl methanesulfonate, 2,5-di-tert-butylphenyl methanesulfonate, 2,4-di-tert-butylphenyl ethanesulfonate, 2,6-di-tert-butylphenyl ethanesulfonate, 3,5-di-tert-butylphenyl ethanesulfonate and 2,4-di-tert-butylphenyl trifluoromethanesulfonate.
3. The tert-butylphenyl alkylsulfonate compound or the tert-butylphenyl arylsulfonate compound according to claim 1 , wherein the compound represented by the general formula (I) is 2,4-di-tert-butylphenyl benzenesulfonate or 2,4-di-tert-butylphenyl p-toluenesulfonate.
4. The tert-butylphenyl alkylsulfonate compound or the tert-butylphenyl arylsulfonate compound according to claim 1 , wherein the compound represented by the general formula (I) is one type of tert-butylphenyl alkylsulfonate compound selected from 3-tert-butylphenyl methanesulfonate, 2-tert-butylphenyl ethanesulfonate and 3-tert-butylphenyl ethanesulfonate.
5. A nonaqueous electrolytic solution for a lithium secondary battery comprising an electrolyte salt dissolved in a nonaqueous solvent comprising the compound of claim 1 .
6. The nonaqueous electrolytic solution for a lithium secondary battery of claim 5 , wherein the nonaqueous solvent comprises 0.01 to 10% by weight of the compound of claim 1 .
7. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 5 , wherein the electrolyte salt is at least one type selected from LiPF 6 , LiBF 4 , LiN(SO 2 CF 3 ) 2 , and LiN(SO 2 C 2 F 5 ) 2 .
8. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 5 , wherein the electrolyte salt comprises LiPF 6 and additionally comprises at least one type selected from LiBF 4 , LiN(SO 2 CF 3 ) 2 , and LiN(SO 2 C 2 F 5 ) 2 .
9. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 5 , wherein the nonaqueous solvent contains a cyclic carbonate and a chain carbonate.
10. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 9 , wherein the cyclic carbonate is at least one type selected from ethylene carbonate, propylene carbonate, butylene carbonate, fluoroethylene carbonate, vinylene carbonate, and vinylethylene carbonate and wherein the chain carbonate contains an asymmetric carbonate selected from methyl ethyl carbonate, methyl propyl carbonate, methyl isopropyl carbonate, methyl butyl carbonate, and ethyl propyl carbonate.
11. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 9 , wherein the ratio between the cyclic carbonate and chain carbonate is 10:90 to 40:60 as the volume ratio.
12. A lithium secondary battery comprising a positive electrode, a negative electrode and the nonaqueous electrolytic solution of claim 5 .
13. A tert-butylphenyl alkylsulfonate compound or tert-butylphenyl arylsulfonate compound represented by general formula (I):
[C1]
wherein, R 1 represents a substituted or non-substituted alkyl group or substituted or non-substituted phenyl group, and n represents an integer of 1 to 2, provided that in the case n=1, the substitution position of the t Bu group is the 2 position or 3 position, in the case the substitution position of the t Bu group is the 2 position, R 1 represents a non-substituted alkyl group having 2 to 4 carbon atoms, in the case the substitution position of the t Bu group is the 3 position, R 1 represents a non-substituted alkyl group having 1 to 4 carbon atoms, and in the case n=2, the substitution positions of the t Bu group are any of the 2,4 position, 2,5 position, 2,6 position or 3,5 position, and in the case t Bu groups are present at the 2,4 position or 3,5 position, R 1 represents a non-substituted alkyl group having 1 to 4 carbon atoms or a non-substituted phenyl group.
14. A nonaqueous electrolytic solution for a lithium secondary battery comprising an electrolyte salt dissolved in a nonaqueous solvent comprising the compound of claim 13 .
15. The nonaqueous electrolytic solution for a lithium secondary battery of claim 14 , wherein the nonaqueous solvent comprises 0.01 to 10% by weight of the compound of claim 13 .
16. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 14 , wherein the electrolyte salt is at least one type selected from LiPF 6 , LiBF 4 , LiN(SO 2 CF 3 ) 2 , and LiN(SO 2 C 2 F 5 ) 2 .
17. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 14 , wherein the electrolyte salt comprises LiPF 6 and additionally comprises at least one type selected from LiBF 4 , LiN(SO 2 CF 3 ) 2 , and LiN(SO 2 C 2 F 5 ) 2 .
18. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 14 , wherein the nonaqueous solvent contains a cyclic carbonate and a chain carbonate.
19. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 18 , wherein the cyclic carbonate is at least one type selected from ethylene carbonate, propylene carbonate, butylene carbonate, fluoroethylene carbonate, vinylene carbonate, and vinylethylene carbonate and wherein the chain carbonate contains an asymmetric carbonate selected from methyl ethyl carbonate, methyl propyl carbonate, methyl isopropyl carbonate, methyl butyl carbonate, and ethyl propyl carbonate.
20. The nonaqueous electrolytic solution for a lithium secondary battery according to claim 18 , wherein the ratio between the cyclic carbonate and chain carbonate is 10:90 to 40:60 as the volume ratio.
21. A lithium secondary battery comprising a positive electrode, a negative electrode and the nonaqueous electrolytic solution of claim 15 .
22. 2,4-di-tert-butylphenyl trifluoromethanesulfonate.