Compounds, complexes, solid electrolytes containing them, and all-solid-state batteries

Abstract

The present invention aims to improve the conventional low lithium-ion conductivity and address the performance and stability problems of all-solid-state batteries, and relates to a compound comprising a repeating unit represented by chemical formula 1 as described herein, a compound that is a lithium salt thereof, a composite comprising the compound and a lithium compound, a solid electrolyte comprising the same, and an all-solid-state battery.

Description

[Technical Field]

[0001] This application claims priority rights under Korean Patent Application No. 10-2023-0057976 dated May 3, 2023, Korean Patent Application No. 10-2023-0057984 dated May 3, 2023, and Korean Patent Application No. 10-2023-0094880 dated July 20, 2023, and all content disclosed in the documents of said Korean Patent Applications is incorporated herein by reference.

[0002] The present invention relates to compounds, composites, solid electrolytes, and all-solid-state batteries for improving the ion conductivity of all-solid-state batteries and suppressing the growth of dendritic crystals of lithium that occur on the surface of a lithium metal anode. [Background technology]

[0003] Currently, high-energy-density lithium-ion batteries, primarily used in laptops and smartphones, consist of a lithium oxide positive electrode, a carbon-based negative electrode, a separator, and a liquid or solid electrolyte. However, lithium-ion batteries with flammable liquid electrolytes have stability issues such as leakage, ignition, and explosion, which necessitates complex battery design to prevent these problems.

[0004] Therefore, in order to solve the problems of such liquid electrolytes, research is being conducted on solid electrolytes that have non-flammable or flame-retardant properties, and these solid electrolytes can be classified into sulfide-based electrolytes, oxide-based electrolytes, and polymer electrolytes.

[0005] While the aforementioned sulfide-based electrolyte has advantages such as high ionic conductivity, low interfacial resistance, and stability over a wide voltage range, it has the problem of being less stable because trace amounts of impurities, such as moisture mixed inside the battery, can react with the sulfide-based electrolyte, generating hydrogen sulfide inside the battery, and there is a risk of hydrogen sulfide generation during charging and discharging of the battery.

[0006] Furthermore, while the oxide-based electrolyte has high chemical stability, it has the disadvantage of having lower ionic conductivity compared to the sulfide-based electrolyte, requiring high-temperature sintering, and making it difficult to manufacture large-area batteries.

[0007] Therefore, because the aforementioned polymer electrolytes possess characteristics such as low cost, ductility, and ease of processing, and thus offer advantages as solid electrolyte materials, research on these polymer electrolytes is being actively conducted.

[0008] The aforementioned polymer electrolytes are broadly classified into gel type and solid type. Gel-type polymer electrolytes impregnate a polymer film with a liquid electrolyte that has a high boiling point, fix it together with a lithium salt, and contain a large amount of liquid electrolyte as the electrolyte that exhibits conductivity. Although they have ionic conductivity similar to that of pure liquid electrolytes, problems with electrochemical stability still remain.

[0009] In contrast, solid polymer electrolytes do not contain liquid electrolytes, thus improving stability issues related to leakage, and they also have the advantage of high chemical and electrochemical stability. However, their ionic conductivity at room temperature is lower than that of liquid electrolytes, and much research is being conducted to improve this.

[0010] Currently, the most widely used material for solid polymer electrolytes is polyethylene oxide (PEO), which, despite being a solid, possesses the ability to conduct lithium ions. However, in the case of linear PEO polymer electrolytes, high crystallinity limits the fluidity of the chains, resulting in a low dielectric constant (5.0) that prevents the dissociation of large amounts of lithium ions. Consequently, the ionic conductivity at room temperature is very low, making it difficult to apply to lithium secondary batteries. [Prior art documents] [Patent Documents]

[0011] [Patent Document 1] Japanese Patent Publication No. 60-069140 [Overview of the project] [Problems that the invention aims to solve]

[0012] The problem that this invention aims to solve is to provide a compound for improving the ionic conductivity of a solid electrolyte and improving the performance and stability of an all-solid-state battery, a solid electrolyte containing the same, and an all-solid-state battery.

[0013] Furthermore, the problem that the present invention aims to solve is to provide a compound for suppressing the growth of lithium dendritic crystals, i.e., dendrites, that occur on the surface of a lithium metal anode, as well as a solid electrolyte and an all-solid-state battery containing the same. [Means for solving the problem]

[0014] The present invention provides compounds, composites, solid electrolytes containing the same, and all-solid-state batteries.

[0015] (1) The present invention provides a compound comprising a repeating unit represented by the following chemical formula 1 or a lithium salt thereof. [ka] In the above chemical formula 1, Each of the aforementioned X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-1, b, and c-1. The aforementioned n is an integer between 1 and 100. The aforementioned q is an integer between 1 and 100. The above o is an integer between 0 and 100. The aforementioned * is a connecting portion or terminal portion between repeating units, [ka] In the aforementioned chemical formulas a-1, b, and c-1, R1, R2, and R3 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C10 an alkoxy group; a substituted or unsubstituted C2-C 10 alkenyl group; a substituted or unsubstituted C2-C 10 alkynyl group; -C(=O)R5; -P(=O)(OR5)2; -P(OR5)(OR6); -OP(=O)(OR5)(OR6); -S(=O)R5; or -S(=O)2R5, and wherein R4 is a hydrogen element; or a substituted or unsubstituted C1-C 10 alkyl group, wherein R5 and R6 are each independently a hydrogen element; a substituted or unsubstituted C1-C 10 alkyl group; or a substituted or unsubstituted C2-C[[ID=十四年]] 10 alkenyl group, wherein L1, L2 and L3 are each independently a direct bond; or a substituted or unsubstituted C1-C 10 alkylene group, wherein X1 and X2 are each independently a hydrogen element; a halogen element; -CN; -NO2; a substituted or unsubstituted C1-C 10 alkyl group; or a substituted or unsubstituted C6-C 12 aryl group, wherein m is an integer from 1 to 40, wherein p is an integer from 1 to 200.

[0016] (2) The present invention provides a compound in which at least one of X, Y and Z contains the compound of Chemical Formula a-1 in (1) above.

[0017] (3) The present invention provides a compound in which R2 and R4 are each independently a C1-C5 alkyl group in (1) or (2) above.

[0018] ]> (4) The present invention provides a compound in which L1, L2 and L3 are each independently a C1-C5 alkylene group in any one of (1) to (3) above.

[0019] (5) The present invention provides a compound in which, in any one of (1) to (4) above, X1 and X2 are each independently a hydrogen element; or a halogen element.

[0020] (6) The present invention provides a compound in any one of (1) to (5) above, wherein n is an integer from 1 to 20, q is an integer from 1 to 20, o is an integer from 0 to 20, m is an integer from 1 to 10, and p is an integer from 1 to 50.

[0021] (7) The present invention provides a compound that, in any one of (1) to (6) above, contains the repeating unit represented by chemical formula 1, which is represented by the following chemical formula 1-a or 1-b. [ka] [ka] In the chemical formulas 1-a and 1-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0022] (8) The present invention provides a compound in which, in any one of (1) to (7) above, at least one of the terminal portions contains one or more functional groups selected from the group consisting of the following chemical formulas d to g. [ka] In the above chemical formulas d to g, The aforementioned R7 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said R8~R 11 These are, independently, direct bonds; substituted or unsubstituted C1-C bonds. 10 an alkylene group; or -R 12 -OR 13 -and, The aforementioned R 12 and R 13These are, independently, directly joined; or substituted or unsubstituted C1-C. 10 It is an alkylene group, The * indicates the bonding position.

[0023] (9) In the present invention, in (8) above, R7 is a C1-C6 alkyl group, and R8~R 11 These are, independently, directly bonded; fluorine-substituted or unsubstituted C1-C6 alkylene groups; or -R 12 -OR 13 - and the R 12 and R 13 Each of these independently provides compounds in which the C1-C6 alkylene group is directly bonded, or substituted or unsubstituted with a fluorine element.

[0024] (10) In the present invention, the compound in (8) or (9) above is a compound represented by the following chemical formula 1-c. [ka] In the chemical formula 1-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0025] (11) The present invention provides a compound in which the lithium salt comprises a repeating unit represented by the following chemical formula 2, in any one of (1) to (10) above. [ka] In the aforementioned chemical formula 2, Each of the aforementioned X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-1, b, and c-1. The aforementioned n is an integer between 1 and 100. The aforementioned q is an integer between 1 and 100. The above o is an integer between 0 and 100. The aforementioned * is a connecting portion or terminal portion between repeating units, [ka] In the aforementioned chemical formulas a-1, b, and c-1, R1, R2, and R3 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; substituted or unsubstituted C2-C 10 The alkynyl group is -C(=O)R5;-P(=O)(OR5)2;-P(OR5)(OR6);-OP(=O)(OR5)(OR6);-S(=O)R5; or -S(=O)2R5. The aforementioned R4 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, R5 and R6 are, independently, hydrogen; substituted or unsubstituted C1-C 10 alkyl groups; or substituted or unsubstituted C2-C 10 It is an alkenyl group, L1, L2, and L3 are each independently directly bonded; or substituted or unsubstituted C1-C 10 It is an alkylene group, The above X1 and X2 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl alkyl groups; or substituted or unsubstituted C6-C 12 It is an aryl group, The aforementioned m is an integer between 1 and 40. The aforementioned p is an integer between 1 and 200.

[0026] (12) The present invention provides a compound represented by the following chemical formula 2-a or 2-b, which, in (11) above, contains the repeating unit represented by chemical formula 2. [ka] [ka] In the chemical formulas 2-a and 2-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0027] (13) The present invention provides a compound in which, in (11) or (12) above, at least one of the terminal portions contains one or more functional groups selected from the group consisting of the following chemical formulas d to g. [ka] In the above chemical formulas d to g, The aforementioned R7 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said R8~R 11 These are, independently, direct bonds; substituted or unsubstituted C1-C bonds. 10 an alkylene group; or -R 12 -OR 13 -and, The aforementioned R 12 and R 13 These are, independently, directly joined; or substituted or unsubstituted C1-C. 10 It is an alkylene group, The * indicates the bonding position.

[0028] (14) The present invention provides a compound represented by the following chemical formula 2-c, which, in (13) above, contains the repeating unit represented by chemical formula 2. [ka] In the chemical formula 2-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0029] (15) The present invention provides a composite comprising a compound and a lithium compound comprising at least one of the above (1) to (14).

[0030] (16) In the present invention, in (15) above, the lithium compound is LiCl, LiBr, LiI, LiBF4, LiClO4, LiB 10 Cl 10 The present invention provides a composite that is one or more selected from the group consisting of LiAlCl4, LiAlO4, LiPF6, LiCF3SO3, LiCH3CO2, LiCF3CO2, LiAsF6, LiSbF6, LiCH3SO3, LiFSI (Lithium bis(fluorosulfonyl)imide, LiN(SO2F)2), LiBETI (lithium bisperfluoroethanesulfonimide, LiN(SO2CF2CF3)2), and LiTFSI (lithium(bis)trifluoromethanesulfonimide, LiN(SO2CF3)2).

[0031] (17) The present invention provides a complex in which, in (15) or (16) above, the complex is represented by one or more complexes selected from the group consisting of the following chemical formulas 3-a, 4-a, and 4-b. [ka] [ka] [ka] In the chemical formulas 3-a, 4-a, and 4-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0032] (18) The present invention provides a solid electrolyte comprising one or more selected from the group consisting of compounds according to (1) to (14) and complexes according to (15) to (17).

[0033] (19) The present invention provides a solid electrolyte further comprising a crosslinkable compound as described in (18) above.

[0034] (20) The present invention provides an all-solid-state battery comprising a solid electrolyte according to (19) above.

[0035] (21) The present invention provides a compound represented by the following chemical formula A. [ka] In the aforementioned chemical formula A, The aforementioned R 21 , R 22 and R 23 These are, independently, hydrogen; halogen; and substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 It is an alkynyl group, The aforementioned R 24 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said L 21 and L 22 These are, independently, substituted or non-substituted C1-C 10 The alkylene group; -P(=O)(OR 25 )-;-(C=O)-;-(S=O)-; or -S(=O)²-, The aforementioned X 21 and X 22 These are, independently, halogen elements; -NH2; phosphate (-OP(=O)(OR 25 )2); Nitrate (-ON (=O) (OR 25 )); Tosylate (-OTs); Sulfonate (-OS(=O)2R 25 ); or carboxylate (-OC(=O)CH3), The aforementioned R 25 C1-C is either substituted or non-substituted. 10 Alkyl group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 It is an alkynyl group.

[0036] (22) In the present invention, in (21) above, R 22 , R 24 and R 25 Each of these independently provides a compound that is a C1-C5 alkyl group.

[0037] (23) The present invention relates to the L in (21) or (22) above. 21 and L 22 This provides a compound that is -S(=O)2-.

[0038] (24) The present invention relates to any one of the above (21) to (23), the X 21 and X 22 Each of these independently provides a compound that is a halogen element or -NH2.

[0039] (25) The present invention provides a compound in which, in any one of (21) to (24) above, the compound represented by chemical formula A is one or more selected from the group consisting of the following chemical formulas Aa, Ab, and Ac. [ka] [ka]

[0040] (26) The present invention provides a composite comprising a compound according to any one of (21) to (25) above and a lithium compound.

[0041] (27) The present invention provides a complex represented by the following chemical formula B in (26) above. [ka] In the aforementioned chemical formula B, The aforementioned R 21 , R 22 and R 23 These are, independently, hydrogen; halogen; and substituted or unsubstituted C1-C 10an alkyl group; substituted or unsubstituted C1-C 10 an alkoxy group; substituted or unsubstituted C2-C 10 an alkenyl group; or substituted or unsubstituted C2-C 10 an alkynyl group, wherein R 24 is a hydrogen element; or substituted or unsubstituted C1-C 10 alkyl group, wherein L 21 and L 22 are each independently a substituted or unsubstituted C1-C 10 alkylene group; -P(=O)(OR 25 ); -(C=O)-; -(S=O)-; or -S(=O)2-, wherein X 21 and X 22 are each independently a halogen element; -NH2; phosphate (-OP(=O)(OR 25 )2); nitrate (-ON(=O)(OR 25 )); tosylate (-OTs); sulfonate (-OS(=O)2R 25 ); or carboxylate (-OC(=O)CH3), wherein R 25 is a substituted or unsubstituted C1-C 10 alkyl group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 alkynyl group, wherein Y - is a halogen anion, BF4 - , ClO4 - , AlCl4 - , AlO4 - , PF6 - , CF3SO3 - , CH3CO2 - , CF3CO2 - , AsF6 - , SbF6 - , CH3SO3 - , FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 -), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - It is one or more selected from the group consisting of ).

[0042] (28) The present invention provides a complex in which, in (26) or (27) above, the complex is one or more selected from the group consisting of the following chemical formulas Ba, Bb, and Bc. [ka] [ka] [ka]

[0043] (29) The present invention provides polymers comprising repeating units derived from a compound according to any one of (21) to (25), repeating units derived from a complex according to any one of (26) to (28), or a combination thereof.

[0044] (30) The present invention provides a polymer in which the repeating unit derived from any one of the compounds in (21) to (25) above is represented by the following chemical formula Wa or Wb. [ka] In the aforementioned chemical formulas Wa and Wb, The aforementioned n is an integer between 1 and 300. The * above represents a connection point between repeating units.

[0045] (31) The present invention provides a polymer in which the repeating unit derived from a composite of any one of (26) to (28) in (29) above is represented by the following chemical formula Xa or Xb. [ka] In the aforementioned chemical formulas Xa and Xb, The aforementioned Y - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - One or more selected from the group consisting of ) The aforementioned n is an integer between 1 and 300. The * above represents a connection point between repeating units.

[0046] (32) The present invention provides a polymer in which, in (29) above, the combination of repeating units derived from a compound according to any one of (21) to (25) above and repeating units derived from a composite according to any one of (26) to (28) above is represented by the following chemical formula Y or Z. [ka] In the aforementioned chemical formulas Y and Z, The aforementioned Y - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3- CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - One or more selected from the group consisting of ) The aforementioned n and m are each independent integers between 1 and 300. The * above represents a connection point between repeating units.

[0047] (33) The present invention provides a solid electrolyte comprising a polymer according to any one of (29) to (32) above. [Effects of the Invention]

[0048] According to the present invention, when a compound having a lithium-affinity structure that can chelate to lithium ions, and a lithium salt of the same compound, are applied to an all-solid-state battery, it is possible to improve ionic conductivity and ion transportability.

[0049] According to the present invention, when a compound with a high lithium ion transport fraction and a compound that is a lithium salt are applied to the electrolyte, it is possible to suppress the growth of lithium dendritic crystals that occur on the surface of the negative electrode. [Modes for carrying out the invention]

[0050] The present invention will be described in more detail below to facilitate understanding of it.

[0051] Herein, terms and words used in this specification and in the claims should not be interpreted in a manner limited to their ordinary or dictionary meanings, but rather in a manner consistent with the technical idea of ​​the present invention, in accordance with the principle that inventors may define the concepts of terms as appropriate to best describe their invention.

[0052] The terms used herein are for illustrative purposes only and are not intended to limit the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise.

[0053] In this specification, terms such as “includes,” “equip,” or “have” indicate the presence of implemented features, figures, steps, components, or combinations thereof, but should be understood not to preclude the existence or possibility of adding one or more different features, figures, steps, components, or combinations thereof.

[0054] As used herein, the term "all-solid-state battery" refers to a battery in which all components are solid, and is distinguished from liquid electrolyte secondary batteries, which use a liquid electrolyte such as an electrolyte solution, and gel polymer secondary batteries, which use a polymer electrolyte instead of a separator and also use a liquid electrolyte.

[0055] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, halogen groups, hydroxyl groups, amino groups, thiol groups, nitro groups, nitrile groups, silyl groups, and linear or branched C1-C6 alkoxy groups, or having no substituents at all.

[0056] As used herein, the term “alkyl group” may mean, unless otherwise specified, a linear or branched acyclic group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms; a cyclic group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms; or a saturated hydrocarbon in which these groups are bonded.

[0057] As used herein, the term "alkenyl group" may mean, unless otherwise specified, a linear or branched acyclic group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 6 carbon atoms with one or more double bonds; a cyclic group having 3 to 20, 3 to 16, 3 to 12, 3 to 8, or 3 to 6 carbon atoms with one or more double bonds; or an unsaturated hydrocarbon in which these groups are bonded.

[0058] As used herein, the term "alkynyl group" may mean, unless otherwise specified, a linear or branched acyclic group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 6 carbon atoms having one or more triple bonds; a cyclic group having 3 to 20, 3 to 16, 3 to 12, 3 to 8, or 3 to 6 carbon atoms having one or more triple bonds; or an unsaturated hydrocarbon in which these groups are bonded.

[0059] In this specification, "*" indicates a bonding position, which is the position where a functional group is bonded to a linking site between repeating units or to a terminal. If it is a terminal, it may be a hydrogen element; -CN; -NH2; a halogen element; or a substituted or unsubstituted C1-C. 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 This can mean one or more selected from the group consisting of alkynyl groups.

[0060] compound The present invention provides a compound containing a repeating unit represented by the following Chemical Formula 1 or a lithium salt thereof.

[0061]

Chem.

[0062] In the Chemical Formula 1, X, Y, and Z are each independently one or more selected from the group consisting of the following Chemical Formulas a-1, b, and c-1; n is an integer from 1 to 100; q is an integer from 1 to 100; o is an integer from 0 to 100; * is a linking site or a terminal site between repeating units;

[0063]

Chem.

[0064]

Chem.

[0065]

Chem.

[0066] In the Chemical Formulas a-1, b, and c-1, R1, R2, and R3 are each independently a hydrogen element; a halogen element; -CN; -NO2; a substituted or unsubstituted C1-C 10 alkyl group; a substituted or unsubstituted C1-C 10 alkoxy group; a substituted or unsubstituted C2-C 10 alkenyl group; a substituted or unsubstituted C2-C 10an alkynyl group; -C(=O)R5; -P(=O)(OR5)2; -P(OR5)(OR6); -OP(=O)(OR5)(OR6); -S(=O)R5; or -S(=O)2R5, and wherein R4 is a hydrogen element; or a substituted or unsubstituted C1-C 10 alkyl group, wherein R5 and R6 are each independently a hydrogen element; a substituted or unsubstituted C1-C 10 alkyl group; or a substituted or unsubstituted C2-C 10 alkenyl group, wherein L1, L2 and L3 are each independently a direct bond; or a substituted or unsubstituted C1-C 10 alkylene group, wherein X1 and X2 are each independently a hydrogen element; a halogen element; -CN; -NO2; a substituted or unsubstituted C1-C 10 alkyl group; or a substituted or unsubstituted C6-C 12 aryl group, wherein m is an integer from 1 to 40, wherein p is an integer from 1 to 200.

[0067] In the case of conventional liquid electrolytes, problems of stability such as ignition occurred because they were flammable. In the case of solid electrolytes, problems of liquid leakage of the liquid did not occur, excellent process stability, and excellent process convenience because thinning and film-forming processing were possible. However, as described above, there is a demerit that the ionic conductivity is significantly lower than that of conventional liquid electrolytes. Therefore, the present inventors have developed a compound having a lithium ion-affine structure according to the present invention and a solid electrolyte containing the same.

[0068] The compound containing the repeating unit represented by Chemical Formula 1 and its lithium salt are compounds having a lithium-affinity structure that can chelate to lithium ions. Because the compound containing the repeating unit represented by Chemical Formula 1 and its lithium salt contain sulfonimide or an anion of sulfonimide from which a proton bonded to the nitrogen element in sulfonimide has been removed, they can have a high affinity for lithium ions when used as a material for solid electrolytes. Furthermore, in the process of manufacturing a solid electrolyte containing the compound containing the repeating unit represented by Chemical Formula 1, a proton bonded to the nitrogen element in sulfonimide can be removed. Also, the sulfonimide anion has a relatively low electron density compared to anions of other organic groups such as carboxylate, and therefore has a weak electrostatic attraction with lithium ions, thus increasing the lithium ion transport number in the solid electrolyte. In particular, the lithium salt can have the effect of improving the lithium ion transport number compared to conventional ethylene oxide-based substances that have been hydrogenated or substances that have a lithium salt separately mixed in, for example, a PEO mixture mixed with a lithium salt.

[0069] Furthermore, since the compound containing the repeating unit represented by chemical formula 1 and its lithium salt contain one or more selected from the group consisting of chemical formulas a-1, b, and c-1, the electrons of the sulfonimide anion are made non-uniform, and the ionic conductivity of the solid electrolyte can be further improved. In addition, since the compound according to the present invention also performs the role of a conventional lithium salt in the solid electrolyte, it can replace a conventional lithium salt, thereby reducing the manufacturing cost of all-solid-state batteries.

[0070] Furthermore, lithium metal anodes, which are attracting attention as next-generation batteries including conventional all-solid-state batteries, suffer from chronic problems such as shortened lifespan and side reaction phenomena due to the formation of lithium dendrites, i.e., lithium dendritic crystals. However, the solid electrolyte containing the compound of the present invention has a high lithium ion transference number, which suppresses the dendrite phenomenon and improves the battery life. In addition, in a rapid charging environment, the formation of lithium dendrites is accelerated, making it difficult to introduce rapid charging with the composition of conventional lithium metal batteries. However, in the case of an all-solid-state battery containing the compound of the present invention, rapid charging is possible because the dendrite phenomenon is suppressed. The compound of the present invention can be a compound containing a repeating unit represented by chemical formula 1 and a lithium salt thereof, and the lithium salt can be a compound containing a repeating unit represented by chemical formula 2, which will be described below. In particular, the results of the experiments described below show that the lithium salt has a considerably high lithium ion transference number, which can more effectively suppress the formation of dendrites.

[0071] Furthermore, according to one embodiment of the present invention, X, Y, and Z can each be independently one or more selected from the group consisting of the following chemical formulas a-1, b, and c-1, and at least one of X, Y, and Z may contain chemical formula a-1. The compound containing the repeating unit represented by chemical formula 1 and its lithium salt are ion-conducting polymers and can have a lithium-affinity structure that can chelate to lithium ions by including a structure that includes an aromatic ring in which an alkoxy group is substituted at one carbon position of a benzene ring and alkyl groups substituted with sulfonyl groups are located at both ortho positions. The present invention provides a lithium-ion conductive compound that can increase the mobility of lithium ions due to the lithium-affinity structure, and when the compound is used as a material for a solid electrolyte, it can have the effect of improving ionic conductivity.

[0072] Furthermore, according to one embodiment of the present invention, R2 and R4 can be C1-C5 alkyl groups.

[0073] Furthermore, according to one embodiment of the present invention, L1, L2, and L3 can be C1-C5 alkylene groups.

[0074] Furthermore, according to one embodiment of the present invention, X1 and X2 can each be independently a hydrogen element or a halogen element, and the halogen element can be one or more selected from the group consisting of F, Cl, Br, and I. The compound containing the repeating unit represented by chemical formula 1 and its lithium salt can contain an alkylene group substituted with a halogen element, preferably the halogen element is fluorine. When the halogen element is fluorine, the high electronegativity of fluorine can delocalize the anions of adjacent sulfonimides, thereby lowering the electron density of the sulfonimides, and as a result, the electrostatic attraction between lithium ions and the solid electrolyte can be relaxed. This allows for more efficient movement of dissociated lithium ions within the electrolyte, can have higher ionic conductivity compared to conventional alkylene oxide polymers, and can have electrochemical stability even at high voltages when used in all-solid-state batteries.

[0075] Furthermore, according to one embodiment of the present invention, in chemical formula 1, chemical formulas a-1, b, and c-1, n can be an integer from 1 to 20, q can be an integer from 1 to 20, o can be an integer from 1 to 20, m can be an integer from 1 to 10, and p can be an integer from 1 to 50.

[0076] Furthermore, according to one embodiment of the present invention, a compound containing the repeating unit represented by chemical formula 1 can be represented by the following chemical formula 1-a or 1-b.

[0077] [ka]

[0078]

Chem.

[0079] In the chemical formulas 1-a and 1-b, n is an integer from 1 to 20, q is an integer from 1 to 20, and o is an integer from 1 to 20.

[0080] When the compound containing the repeating unit represented by the chemical formula 1 is represented by the chemical formula 1-a or 1-b, it can have a higher lithium ion conductivity than the polymer materials of the solid electrolytes used conventionally.

[0081] According to one embodiment of the present invention, at least one of the terminal sites can contain one or more functional groups selected from the group consisting of the following chemical formulas d to g.

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086] <000099​​​​​​​​​​an alkylene group; or -R 12 -OR 13 -and, The aforementioned R 12 and R 13 These are, independently, directly joined; or substituted or unsubstituted C1-C. 10 It is an alkylene group, The * indicates the bonding position.

[0087] The compound contains one or more functional groups selected from the group consisting of chemical formulas d to g at at least one of the ends of the repeating units, which facilitates the formation of a network between the repeating units within the compound. This network formation significantly increases the weight-average molecular weight of the polymer, thereby improving the mechanical strength of the solid electrolyte when the compound or its salt is applied to it.

[0088] Furthermore, according to one embodiment of the present invention, in the chemical formulas d to g, R7 is a C1-C6 alkyl group, and R8 to R 11 These are, independently, directly bonded; fluorine-substituted or unsubstituted C1-C6 alkylene groups; or -R 12 -OR 13 - and the R 12 and R 13 Each of these can independently be a directly bonded, fluorine-substituted, or unsubstituted C1-C6 alkylene group. Specifically, the functional groups of chemical formulas d-g can be one or more selected from the group consisting of acrylate, vinyl, isocyanate, and alcohol structures.

[0089] On the other hand, in the process of polymerizing the compounds contained in the solid electrolyte of the present invention, in addition to the repeating unit represented by chemical formula 1 and the compound having one or more functional groups selected from the group consisting of the following chemical formulas d to g at at least one of the ends of the repeating unit, and its lithium salt, further crosslinkable compounds may be included. The crosslinkable compounds may be one or more selected from the group consisting of polyfunctional acrylates, vinyl groups, isocyanates, and alcohol structures.

[0090] For example, if a functional group of chemical formula d or e having an acrylate or vinyl group structure is located at the end of the repeating unit, a network between the repeating units can be formed by adding a crosslinkable compound containing pentaerythritol tetraacrylate (PETA). Here, since the acrylate, vinyl group and PETA contain a double bond structure, radical polymerization can be formed between the functional group of chemical formula d or e and the double bond of the crosslinkable compound.

[0091] Furthermore, for example, if the functional group of chemical formula g having an alcohol structure (-OH) is located at the end of the repeating unit, a network between the repeating units can be formed by adding a crosslinking compound containing hexamethylene diisocyanate (1,6-diisocyanatohexane). Also, if the functional group of chemical formula f having an isocyanate structure (-NCO) is located at the end of the repeating unit, a network between the repeating units can be formed by adding a crosslinking compound containing glycerol or propane-1,2,3-tricarboxylic acid. Here, the -OH group and the -NCO group can form a bond of the -NHCOO- structure through an addition polymerization reaction.

[0092] Furthermore, according to one embodiment of the present invention, the compound can be represented by the following chemical formula 1-c.

[0093] [ka]

[0094] In the chemical formula 1-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0095] Specifically, when the compound containing the repeating unit represented by chemical formula 1 is represented by chemical formula 1-c, it can have a higher lithium ion conductivity compared to conventionally used polymer materials for solid electrolytes.

[0096] According to one embodiment of the present invention, the lithium salt of a compound containing the repeating unit represented by chemical formula 1 may be a compound containing the repeating unit represented by the following chemical formula 2.

[0097] [ka]

[0098] In the aforementioned chemical formula 2, Each of the aforementioned X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-1, b, and c-1. The aforementioned n is an integer between 1 and 100. The aforementioned q is an integer between 1 and 100. The above o is an integer between 0 and 100. The * above represents a connection point between repeating units.

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] In the aforementioned chemical formulas a-1, b, and c-1, R1, R2, and R3 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; substituted or unsubstituted C2-C 10 The alkynyl group is -C(=O)R5;-P(=O)(OR5)2;-P(OR5)(OR6);-OP(=O)(OR5)(OR6);-S(=O)R5; or -S(=O)2R5. The aforementioned R4 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, R5 and R6 are, independently, hydrogen; substituted or unsubstituted C1-C 10 Alkyl group of; or substituted or unsubstituted C2-C 10 It is an alkenyl group, L1, L2, and L3 are each independently directly bonded; or substituted or unsubstituted C1-C 10 It is an alkylene group, The above X1 and X2 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl alkyl groups; or substituted or unsubstituted C6-C 12 It is an aryl group, The aforementioned m is an integer between 1 and 40. The aforementioned p is an integer between 1 and 200.

[0103] The compound containing the repeating unit represented by chemical formula 2 is a compound containing the repeating unit represented by chemical formula 1 that has been lithified, and can have the effect of improving the lithium ion transference number.

[0104] Furthermore, according to one embodiment of the present invention, the compound containing the repeating unit represented by chemical formula 2 may be a compound represented by the following chemical formula 2-a or 2-b.

[0105] [ka]

[0106] [ka]

[0107] In the chemical formulas 2-a and 2-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0108] When a compound containing the repeating unit represented by chemical formula 2 is represented by chemical formula 2-a or 2-b, it can have higher lithium ion conductivity compared to conventionally used polymer materials for solid electrolytes.

[0109] According to one embodiment of the present invention, the lithium salt compound may contain at least one of the terminal sites one or more functional groups selected from the group consisting of the following chemical formulas d to g.

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] In the above chemical formulas d to g, The aforementioned R7 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said R8~R 11 These are, independently, direct bonds; substituted or unsubstituted C1-C bonds. 10 an alkylene group; or -R 12 -OR 13 -and, The aforementioned R 12 and R 13 These are, independently, directly joined; or substituted or unsubstituted C1-C. 10 It is an alkylene group, The * indicates the bonding position.

[0115] Furthermore, according to one embodiment of the present invention, a compound containing the repeating unit represented by chemical formula 2 can be represented by the following chemical formula 2-c.

[0116] [ka]

[0117] In the chemical formula 2-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0118] Specifically, when the compound containing the repeating unit represented by chemical formula 2 is represented by chemical formula 2-c, it can have a higher lithium ion conductivity compared to conventionally used polymer materials for solid electrolytes.

[0119] complex The present invention provides a compound according to the present invention; and a complex comprising a lithium compound.

[0120] Specifically, the present invention provides compounds comprising one or more compounds selected from the group consisting of the compound of chemical formula 1 and its lithium salt; and complexes comprising lithium compounds.

[0121] The aforementioned complex may be a complex containing a repeating unit represented by the following chemical formula 3 or a repeating unit represented by the chemical formula 4.

[0122] [ka]

[0123] [ka]

[0124] In the aforementioned chemical formulas 3 and 4, Each of X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-2, b, c-1, and c-2, but at least one of X, Y, and Z must contain either chemical formula a-2 or c-2. The aforementioned n is an integer between 1 and 100. The aforementioned q is an integer between 1 and 100. The above o is an integer between 0 and 100. The * above is a connecting part between repeating units,

[0125] [ka]

[0126] [ka]

[0127] [ka]

[0128] [ka]

[0129] In the aforementioned chemical formulas a-2, b, c-1, and c-2, R1, R2, and R3 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; substituted or unsubstituted C2-C 10 The alkynyl group is -C(=O)R5;-P(=O)(OR5)2;-P(OR5)(OR6);-OP(=O)(OR5)(OR6);-S(=O)R5; or -S(=O)2R5, The aforementioned R4 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, R5 and R6 are, independently, hydrogen; substituted or unsubstituted C1-C 10 Alkyl group of; or substituted or unsubstituted C2-C 10 It is an alkenyl group, L1, L2, and L3 are each independently directly bonded; or substituted or unsubstituted C1-C 10 It is an alkylene group, The above X1 and X2 are, independently, hydrogen; halogen; -CN; -NO2; substituted or unsubstituted C1-C 10 Alkyl alkyl groups; or substituted or unsubstituted C6-C 12 It is an aryl group, A - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2- CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - One or more selected from the group consisting of ) The aforementioned m is an integer between 1 and 40. The aforementioned p is an integer between 1 and 200.

[0130] According to one embodiment of the present invention, the composite comprising the repeating unit represented by chemical formula 3 or the repeating unit represented by chemical formula 4 may comprise one or more compounds comprising the repeating unit represented by chemical formula 1 or its lithium salts and a lithium compound, wherein the one or more compounds comprising the repeating unit represented by chemical formula 1 or its lithium salts and the lithium compound are bonded by electrostatic attraction. By further comprising the lithium compound, the composite of the present invention can increase the transport rate of lithium ions, thereby improving ionic conductivity, reducing the diffusion resistance of lithium ions, and achieving the effect of improving the cycle capacity characteristics of a lithium secondary battery.

[0131] According to one embodiment of the present invention, X, Y, and Z are each independently one or more selected from the group consisting of the following chemical formulas a-2, b, c-1, and c-2, but at least one of X, Y, and Z must contain chemical formula a-2 or c-2. L1, L2, and L3 can be C1-C5 alkylene groups, and X1 to X4 can each independently be a hydrogen element or a halogen element, and the halogen element can be one or more selected from the group consisting of F, Cl, Br, and I. Furthermore, n can be an integer from 1 to 20, q can be an integer from 1 to 20, o can be an integer from 1 to 20, m can be an integer from 1 to 10, and p can be an integer from 1 to 50. The effect of the substituent is the same as the effect of the compound containing the repeating unit represented by the above chemical formula 1 and its lithium salt.

[0132] The lithium compound is Li + Y - It can be expressed as the anion (Y) of the lithium compound. - ) is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - It can be one or more selected from the group consisting of ), specifically the anion (Y) of the lithium compound. -) can be a halogen anion.

[0133] According to one embodiment of the present invention, R2 and R4 may be C1-C5 alkyl groups. In the structure of chemical formula 3 or chemical formula 4, if R4 is substituted with a C1-C5 alkyl group and the complex contains an alkoxy group, the lithium compound may be located in close proximity to the alkoxy group by electrostatic attraction, specifically, the lithium compound may be Li + Y - It can be positioned in the form of.

[0134] Furthermore, the lithium compound contained in the composite can be present in an amount of 1 to 40% by weight. By including the lithium compound in the composite within this range, the lithium ion transport rate can be increased, battery resistance can be reduced, and the effect of improving cycle capacity characteristics can be achieved.

[0135] According to one embodiment of the present invention, the complex may contain at least one of the terminal sites one or more functional groups selected from the group consisting of the following chemical formulas d to g.

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] [ka]

[0140] In the above chemical formulas d to g, The aforementioned R7 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said R8~R 11 These are, independently, direct bonds; substituted or unsubstituted C1-C bonds. 10 an alkylene group; or -R 12 -OR 13 -and, The aforementioned R 12 and R 13 These are, independently, directly joined; or substituted or unsubstituted C1-C. 10 It is an alkylene group, The * indicates the bonding position.

[0141] According to one embodiment of the present invention, the complex may be a complex represented by one or more selected from the group consisting of the following chemical formulas 3-a, 4-a, and 4-b.

[0142] [ka]

[0143] [ka]

[0144] [ka]

[0145] In the chemical formulas 3-a, 4-a, and 4-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0146] When a composite containing repeating units represented by chemical formula 3 or chemical formula 4 is a composite represented by one or more selected from the group consisting of chemical formulas 3-a, 4-a, and 4-b, it can have higher lithium ion conductivity than conventionally used polymer materials for solid electrolytes.

[0147] Compounds (monomers) The present invention provides a compound represented by the following chemical formula A.

[0148] [ka]

[0149] In the aforementioned chemical formula A, The aforementioned R 21 , R 22 and R 23 These are, independently, hydrogen; halogen; and substituted or unsubstituted C1-C 10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 It is an alkynyl group, The aforementioned R 24 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said L 21 and L 22 These are, independently, substituted or non-substituted C1-C 10 The alkylene group; -P(=O)(OR 25 )-;-(C=O)-;-(S=O)-; or -S(=O)²-, The aforementioned X 21 and X 22 These are, independently, halogen elements; -NH2; phosphate (-OP(=O)(OR 25 )2); Nitrate (-ON (=O) (OR 25 )); Tosylate (-OTs); Sulfonate (-OS(=O)2R 25 ); or carboxylate (-OC(=O)CH3), The aforementioned R 25 C1-C is either substituted or non-substituted. 10 Alkyl group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10It is an alkynyl group.

[0150] The compound represented by chemical formula A may be a monomer. The compound represented by chemical formula A may be an aromatic ring substance in which an alkoxy group is substituted at one carbon position of a benzene ring, and alkyl groups substituted with sulfonyl groups are located at both ortho positions. Based on structural properties that allow the compound to chelate to lithium ions, such as crown ether compounds to which the molecular recognition concept of Supramolecular Chemistry is applied, the target substance is Li + The present invention provides a lithium-ion conductive compound that can increase the mobility of lithium ions (lithium-ion transport fraction) due to its lithium-affinity structure, and when the compound is used as a material for a solid electrolyte, it can have the effect of improving ionic conductivity.

[0151] According to one embodiment of the present invention, in the chemical formula A, the R 22 , R 24 and R 25 This can be a C1-C5 alkyl group.

[0152] According to one embodiment of the present invention, in the chemical formula A, the X 21 and X 22 Each of these elements can independently be a halogen element or -NH2. The compound represented by chemical formula A can form an ion-conducting polymer as a monomer, and if the compound represented by chemical formula A contains one or more halogen elements, such as F, Cl, I, and Br, or NH2, a condensation reaction can occur between the halogen element and NH2 to form the ion-conducting polymer.

[0153] According to one embodiment of the present invention, in the chemical formula A, the L 21 and L 22 can be -S(=O)2-. Specifically, the compound represented by the chemical formula A is L 21 and L 22 The X contains a sulfonyl group, 21 and X 22 When the compound contains -NH2, the compound represented by chemical formula A contains sulfonimide or an anion of sulfonimide from which a proton bonded to the nitrogen element in the sulfonimide has been removed, thus allowing for a high affinity with lithium ions when used as a material for a solid electrolyte. On the other hand, in the process of manufacturing a solid electrolyte containing a compound with repeating units represented by chemical formula A, a proton bonded to the nitrogen element in the sulfonimide can be removed. In this case, the electron density of the sulfonimide anion is relatively low compared to anions of other organic groups such as carboxylate, resulting in a weaker electrostatic attraction with lithium ions, thus improving the lithium ion transport efficiency, i.e., ionic conductivity. Furthermore, when the compound represented by chemical formula A contains an alkoxy group, the oxygen of the alkoxy group, along with two sulfonyl groups adjacent to the ortho position, can chelate to lithium, improving lithium affinity, and as a result, improving the lithium ion conductivity of the solid electrolyte to which this material is applied. In particular, the lithium salt can have the effect of improving the lithium ion transference number compared to conventional ethylene oxide-based substances that have been hydrogenated or substances that have a lithium salt separately mixed in, for example, a PEO mixture mixed with a lithium salt.

[0154] Furthermore, according to one embodiment of the present invention, the compound represented by chemical formula A may be one or more compounds selected from the group consisting of the following chemical formulas Aa, Ab, and Ac.

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] When the compound represented by chemical formula A is one or more selected from the group consisting of chemical formulas Aa, Ab, and Ac, it can have higher lithium ion conductivity compared to conventionally used polymer materials for solid electrolytes.

[0159] complex (monomer) The present invention provides a composite comprising a compound represented by the chemical formula A and a lithium compound. The composite of the present invention can increase the transport rate of lithium ions by further comprising the lithium compound, thereby improving ionic conductivity and reducing the diffusion resistance of lithium ions, thereby achieving the effect of improving the cycle capacity characteristics of a lithium secondary battery.

[0160] According to one embodiment of the present invention, the composite can be a composite represented by the following chemical formula B. In the composite represented by chemical formula B, the compound represented by chemical formula A and the lithium compound are bonded together by electrostatic attraction.

[0161] [ka]

[0162] In the aforementioned chemical formula B, The aforementioned R 21 , R 22 and R 23 These are, independently, hydrogen; halogen; and substituted or unsubstituted C1-C10 Alkyl group; substituted or unsubstituted C1-C 10 Alkoxy group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 It is an alkynyl group, The aforementioned R 24 is the element hydrogen; or substituted or unsubstituted C1-C 10 It is an alkyl group, Said L 21 and L 22 These are, independently, substituted or non-substituted C1-C 10 The alkylene group; -P(=O)(OR 25 )-;-(C=O)-;-(S=O)-; or -S(=O)²-, The aforementioned X 21 and X 22 These are, independently, halogen elements; -NH2; phosphate (-OP(=O)(OR 25 )2); Nitrate (-ON (=O) (OR 25 )); Tosylate (-OTs); Sulfonate (-OS(=O)2R 25 ); or carboxylate (-OC(=O)CH3), The aforementioned R 25 C1-C is either substituted or non-substituted. 10 Alkyl group; substituted or unsubstituted C2-C 10 alkenyl group; or substituted or unsubstituted C2-C 10 It is an alkynyl group, The aforementioned Y - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 -), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - It is one or more selected from the group consisting of ).

[0163] According to one embodiment of the present invention, in the chemical formula B, the R 22 , R 24 and R 25 can be a C1-C5 alkyl group. Also, in the above chemical formula B, the L 21 and L 22 can be -S(=O)2-, and the above X 21 and X 22 Each of these elements can independently be a halogen element or -NH2. The halogen element can be any one of F, Cl, I, and Br. The effects of the substituents are the same as those of the compound represented by chemical formula A.

[0164] The lithium compound is Li + Y - It can be expressed as the anion (Y) of the lithium compound. - ) is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 -) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - It can be one or more selected from the group consisting of ), specifically the anion (Y) of the lithium compound. - ) can be a halogen anion.

[0165] According to one embodiment of the present invention, in the structure of chemical formula B, R 24 When is substituted with an alkyl group and the complex contains an alkoxy group, the lithium compound can be positioned in close proximity to the alkoxy group by electrostatic attraction, specifically, the lithium compound is Li + Y - It can be positioned in the form of.

[0166] Furthermore, the lithium compound contained in the composite can be present in an amount of 1 to 75% by weight of the composite. When the lithium compound is present in an amount within this range, 1 to 4 moles of lithium cations can be present per mole of the composite, which can increase the lithium ion transport fraction, reduce the lithium ion diffusion resistance, and improve the cycle capacity characteristics.

[0167] According to one embodiment of the present invention, the composite can be one or more composites selected from the group consisting of the following chemical formulas: Ba, Bb, and Bc.

[0168] [ka]

[0169] [ka]

[0170] [ka]

[0171] When the composite represented by the chemical formula B is one or more composites selected from the group consisting of the chemical formulas Ba, Bb, and Bc, it can have higher lithium ion conductivity compared to conventionally used polymer materials for solid electrolytes.

[0172] polymer The present invention provides polymers comprising repeating units derived from a compound represented by chemical formula A, repeating units derived from a composite represented by chemical formula B, or combinations thereof.

[0173] According to one embodiment of the present invention, the compound and the composite can be monomers, and the monomers can be polymerized to form a polymer which is an ionic conductive solid electrolyte material. Specifically, the compound represented by chemical formula A and the composite represented by chemical formula B are X 21 and X 22 The position may contain a halogen element or -NH2, for example, the halogen element may be one or more of F, Cl, I, and Br. In this case, the compound represented by chemical formula A and the composite represented by chemical formula B can undergo polymerization by a condensation reaction between the contained halogen element and the -NH2 to form a polymer containing sulfonylimide.

[0174] Furthermore, according to one embodiment of the present invention, the polymer may further contain, in addition to the repeating units derived from the compound and the composite, one or more repeating units derived from fluorine-based compounds and alkylene oxide monomers.

[0175] According to one embodiment of the present invention, the repeating unit derived from the compound can be represented by the following chemical formulas Wa or Wb.

[0176] [ka]

[0177] [ka]

[0178] In the aforementioned chemical formulas Wa and Wb, The aforementioned n is an integer between 1 and 300. The * above represents a connection point between repeating units.

[0179] The chemical formula Wb is a repeating unit derived from the lithium salt of the compound represented by the chemical formula A, and compounds containing this repeating unit can have the effect of further improving the lithium ion transference number.

[0180] Furthermore, according to one embodiment of the present invention, the repeating unit derived from the composite can be represented by the following chemical formula Xa or Xb.

[0181] [ka]

[0182] [ka]

[0183] In the aforementioned chemical formulas Xa and Xb, The aforementioned Y - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI - (bis(fluorosulfonyl)imide, N(SO2F)2 -), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - One or more selected from the group consisting of ) The aforementioned n is an integer between 1 and 300. The * above represents a connection point between repeating units.

[0184] The aforementioned chemical formula Xb includes a lithified compound and can have the effect of further improving the lithium ion transference number of the solid electrolyte.

[0185] Furthermore, according to one embodiment of the present invention, a combination of repeating units derived from the compound and repeating units derived from the complex can be represented by the following chemical formula Y or Z.

[0186] [ka]

[0187] [ka]

[0188] In the aforementioned chemical formulas Y and Z, The aforementioned Y - is a halogen anion, BF4 - ClO4 - AlCl4 - AlO4 - PF6 - CF3SO3 - CH3CO2 - CF3CO2 - AsF6 - SbF6 - CH3SO3 - FSI -(bis(fluorosulfonyl)imide, N(SO2F)2 - ), BETI(lithium bisperfluoroethanesulfonimide, N(SO2CF2CF3)2 - ) and TFSI((bis)trifluoromethanesulfonimide, N(SO2CF3)2 - One or more selected from the group consisting of ) The aforementioned n and m are each independent integers between 1 and 300. The * above represents a connection point between repeating units.

[0189] The aforementioned chemical formula Z includes a lithified compound and can have the effect of further improving the lithium ion transference number of the solid electrolyte.

[0190] solid electrolyte The present invention provides a solid electrolyte comprising one or more selected from the group consisting of the compound and the composite. Specifically, the compound may be a compound comprising a repeating unit represented by chemical formula 1 or a repeating unit represented by chemical formula 2, and the composite may be a composite comprising a repeating unit represented by chemical formula 3 or chemical formula 4. The present invention also provides a solid electrolyte comprising the polymer. Here, the polymer may include repeating units derived from the compound which is the compound represented by chemical formula A, repeating units derived from the composite, or a combination thereof. Since the solid electrolyte comprises a polymer with a lithium-ion-affinity structure, it can have the effect of improving lithium ion mobility and ionic conductivity.

[0191] According to one embodiment of the present invention, the solid electrolyte may further contain a crosslinkable compound, which may be one or more selected from the group consisting of polyfunctional acrylates, vinyl groups, isocyanates, and alcohol structures. At least one of the ends of the repeating unit may have one or more functional groups selected from the group consisting of the following chemical formulas d to g, and the crosslinkable compound can form a network between the repeating units by radical polymerization or addition polymerization. Details regarding the crosslinkable compound are as described in the compound index.

[0192] On the other hand, the present invention allows for the production of a mixed solution by mixing a solvent with one or more substances selected from the group consisting of the aforementioned compound and the aforementioned complex, and the formation of an ion-conducting polymer electrolyte film by a film manufacturing process using the mixed solution. The solvent can be one or more substances selected from the group consisting of methanol, ethanol, 2-propanol, butanol, 2-ethoxyethanol, isopropyl alcohol, ethyl acetate, butyl acetate, acetone, dichloroethane, acetonitrile, tetrahydrofuran, N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosamide, 1,3-dimethyl-2-imidazolidinone, triethyl phosphate, and gamma-butyrolactone. The content of the solvent can be determined considering the viscosity of the mixed solution, etc.

[0193] Furthermore, the manufacturing process of the film can be a solution casting method (solution casting method), a melt extrusion method, a calendering method, or a compression molding method, and more specifically, a solution casting method. The solution casting method can be carried out by coating on another substrate, separating it, and bonding it to the positive and negative electrodes. The substrate can be a glass substrate or a plastic substrate. Examples of plastic substrates include various plastic films such as polyethylene terephthalate, polyethylene naphthalate, polypropylene, polyethylene, cellulose triacetate, cellulose diacetate, alkyl poly(meth)acrylate, poly(meth)acrylate copolymer, polyvinyl chloride, polyvinyl alcohol, polycarbonate, polystyrene, cellophane, polyvinylidene chloride copolymer, polyamide, polyimide, vinyl chloride / vinyl acetate copolymer, polytetrafluoroethylene, and polytrifluoroethylene. The thickness of the support is preferably 5 to 150 μm, and more preferably 10 to 50 μm. Furthermore, the coating can be applied using methods such as spin coating, dip coating, solvent casting, slot die coating, spray coating, roll coating, extrusion coating, curtain coating, die coating, wire bar coating, or knife coating.

[0194] All solid state battery The present invention provides an all-solid-state battery containing the solid electrolyte.

[0195] According to one embodiment of the present invention, the all-solid-state battery includes a positive electrode, a negative electrode (or anode-less), and a solid electrolyte layer containing a solid electrolyte disposed between the positive electrode and the negative electrode. The all-solid-state battery according to the present invention exhibits excellent initial efficiency, life characteristics, and output characteristics because it has less ionic conductivity degradation and low electronic conductivity of the contained solid electrolyte. Herein, the all-solid-state battery of the present invention can be manufactured according to conventional methods well known in the art. For example, it can be manufactured by laminating and pressurizing such that a solid electrolyte layer exists between the positive electrode and the negative electrode.

[0196] (1) Positive electrode The positive electrode can be manufactured by coating a positive electrode slurry containing a positive electrode active material, a binder, a conductive material, and a solvent onto a positive electrode current collector.

[0197] The positive electrode current collector is not particularly limited as long as it does not cause chemical changes in the battery and is conductive. For example, stainless steel, aluminum, nickel, titanium, calcined carbon, or aluminum or stainless steel with surface treatment using carbon, nickel, titanium, silver, etc., can be used. Furthermore, fine irregularities can be formed on the surface to strengthen the bonding force of the positive electrode active material, and it can be used in various forms such as films, sheets, foils, meshes, porous materials, foams, and nonwoven fabrics.

[0198] The positive electrode active material may include, specifically, a lithium metal oxide containing lithium and one or more metals such as cobalt, manganese, nickel, or aluminum, as a compound capable of reversible intercalation and deintercalation of lithium. More specifically, the lithium metal oxide may be a lithium-manganese oxide (e.g., LiMnO2, LiMn2O4, etc.), a lithium-cobalt oxide (e.g., LiCoO2, etc.), a lithium-nickel oxide (e.g., LiNiO2, etc.), or a lithium-nickel-manganese oxide (e.g., LiNi 1-Y Mn YO2 (where 0 < Y < 1), LiMn 2-z Ni z O4 (where 0 < Z < 2), etc.), lithium-nickel-cobalt-based oxides (e.g., LiNi 1-Y1 Co Y1 O2 (where 0 < Y1 < 1), etc.), lithium-manganese-cobalt-based oxides (e.g., LiCo 1-Y2 Mn Y2 O2 (where 0 < Y2 < 1), LiMn 2-z1 Co z1 O4 (where 0 < Z1 < 2), etc.), lithium-nickel-manganese-cobalt-based oxides (e.g., Li(Ni p Co q Mn r1 )O2 (where 0 < p < 1, 0 < q < 1, 0 < r1 < 1, p + q + r1 = 1) or Li(Ni p1 Co q1 Mn r2 )O4 (where 0 < p1 < 2, 0 < q1 < 2, 0 < r2 < 2, p1 + q1 + r2 = 2), etc.), or lithium-nickel-cobalt-transition metal (M) oxides (e.g., Li(Ni p2 Co q2 Mn r3 M S2 )O2 (where M is selected from the group consisting of Al, Fe, V, Cr, Ti, Ta, Mg, and Mo, and p2, q2, r3, and s2 are the atomic fractions of the respective independent elements, 0 < p2 < 1, 0 < q2 < 1, 0 < r3 < 1, 0 < s2 < 1, and p2 + q2 + r3 + s2 = 1), etc.), and any one or two or more of these compounds can be included.

[0199] Among them, in terms of being able to enhance the capacity characteristics and stability of the battery, the lithium metal oxide is LiCoO2, LiMnO2, LiNiO2, lithium nickel manganese cobalt oxide (e.g., Li(Ni 1 / 3 Mn 1 / 3 Co 1 / 3 )O2, Li(Ni 0.6 Mn 0.2 Co 0.2 )O2, Li(Ni 0.5 Mn 0.3 Co0.2 )O2, Li(Ni 0.7 Mn 0.15 Co 0.15 )O2, and Li(Ni 0.8 Mn 0.1 Co 0.1 )O2 etc.), or lithium nickel cobalt aluminum oxide (e.g., Li(Ni 0.8 Co 0.15 Al 0.05 It can be Li(Ni)(O2, etc.), and considering the remarkable improvement effect by controlling the type and content ratio of constituent elements that form the lithium composite metal oxide, the lithium composite metal oxide is Li(Ni)(O2, etc.). 0.6 Mn 0.2 Co 0.2 )O2, Li(Ni 0.5 Mn 0.3 Co 0.2 )O2, Li(Ni 0.7 Mn 0.15 Co 0.15 )O2, and Li(Ni 0.8 Mn 0.1 Co 0.1 ) These can be O2, etc., and one or more of these, or a mixture of two or more, can be used.

[0200] The positive electrode active material may be present in an amount of 60% or more, 70% or more, 80% or more, or 99% or less, or 98% or less, relative to the total weight of the solid content other than the solvent in the positive electrode slurry.

[0201] The aforementioned binder is a component that helps to bond the conductive material, active material, and current collector. Examples of such binders include polyvinylidene fluoride, polyvinyl alcohol, carboxymethylcellulose, starch, hydroxypropylcellulose, regenerated cellulose, polyvinylpyrrolidone, tetrafluoroethylene, polyethylene, polypropylene, ethylene-propylene-diene monomer, sulfonated ethylene-propylene-diene monomer, styrene-butadiene rubber, fluororubber, and various copolymers thereof.

[0202] Typically, the binder can be present in the cathode slurry at an amount of 1% to 20% by weight, preferably 1% to 15% by weight, and more preferably 1% to 10% by weight, relative to the total weight of the solids other than the solvent.

[0203] The aforementioned conductive material is a component that further improves the conductivity of the positive electrode active material.

[0204] The conductive material is not particularly limited as long as it does not cause a chemical change in the battery and is conductive. For example, graphite; carbon-based materials such as carbon black, acetylene black, Ketjen black, channel black, furnace black, lamp black, and thermal black; conductive fibers such as carbon fibers and metal fibers; metal powders such as carbon fluoride, aluminum, and nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; and conductive materials such as polyphenylene derivatives can be used.

[0205] Typically, the conductive material can be included in the positive electrode slurry in an amount of 1% or more, 20% or less by weight, 15% or less by weight, or 10% or less by weight, relative to the total weight of solid matter other than the solvent.

[0206] The solvent may include organic solvents such as NMP (N-methyl-2-pyrrolidone) and can be used in an amount that results in a desirable viscosity when the positive electrode active material and, selectively, a binder and conductive material are included. For example, the solid content containing the positive electrode active material and, selectively, the binder and conductive material can be included in amounts of 50% by weight or more, 60% by weight or more, 70% by weight or more, 95% by weight or less, 90% by weight or less, and 85% by weight or less.

[0207] (2) Negative electrode The negative electrode can be manufactured, for example, by coating a negative electrode slurry containing a negative electrode active material, binder, conductive material, and solvent onto a negative electrode current collector, or by using a graphite electrode made of carbon (C) or lithium metal itself with a thickness of 50 μm or less as the negative electrode, or the negative electrode can be eliminated by anode-less design.

[0208] For example, when a negative electrode is manufactured by coating a negative electrode slurry onto the negative electrode current collector, the negative electrode current collector generally has a thickness of 3 to 500 μm. Such a negative electrode current collector is not particularly limited as long as it does not cause chemical changes in the battery and has high conductivity. For example, copper, stainless steel, aluminum, nickel, titanium, calcined carbon, copper or stainless steel with surface treatment using carbon, nickel, titanium, silver, etc., and aluminum-cadmium alloys can be used. Also, similar to the positive electrode current collector, fine irregularities can be formed on the surface to strengthen the bonding force of the negative electrode active material, and it can be used in various forms such as films, sheets, foils, meshes, porous materials, foams, and nonwoven fabrics.

[0209] The negative electrode active material may be natural graphite, artificial graphite, carbonaceous material; lithium-containing titanium composite oxide (LTO), Si, SiO x Metals (Me) that are Sn, Li, Zn, Mg, Cd, Ce, Ni, or Fe; alloys composed of the aforementioned metals (Me); oxides (MeO) of the aforementioned metals (Me) x Examples of negative electrode active materials include silicon (Si), silicon oxide (SiO2), and one or more selected from the group consisting of the aforementioned metals (Me) and carbon composites. Specifically, negative electrode active materials include silicon (Si), silicon oxide (SiO2), and silicon oxide (SiO2). x A silicon-based negative electrode active material or lithium metal, including silicon alloy, can be used. In the case of a silicon-based negative electrode active material, a thin, stable SEI layer containing siloxane bonds is formed, which can further improve the high-temperature stability and lifespan characteristics of the battery.

[0210] Furthermore, the lithium metal can be a conventional material containing lithium metal or lithium alloy (for example, an alloy of lithium with a metal such as aluminum, zinc, vizmus, cadmium, antimony, silicon, lead, tin, gallium, or indium). The lithium metal anode active material can be in foil form, and by depositing the lithium metal anode active material onto one surface of the anode current collector, the lithium metal anode active material can form a separate layer from the anode current collector.

[0211] The negative electrode active material may be present in the negative electrode slurry in an amount of 60% or more, 70% or more, 80% or more, 99% or less, or 98% or less, relative to the total weight of the solid content other than the solvent.

[0212] The aforementioned binder is a component that helps to bond the conductive material, active material, and current collector. Examples of such binders include polyvinylidene fluoride, polyvinyl alcohol, carboxymethylcellulose, starch, hydroxypropylcellulose, regenerated cellulose, polyvinylpyrrolidone, tetrafluoroethylene, polyethylene, polypropylene, ethylene-propylene-diene monomer, sulfonated ethylene-propylene-diene monomer, styrene-butadiene rubber, fluororubber, and various copolymers thereof.

[0213] Typically, the binder can be included in the negative electrode slurry in an amount of 1% by weight or more, 20% by weight or less, 15% by weight or less, or 10% by weight or less, relative to the total weight of the solids other than the solvent.

[0214] The conductive material is a component for further improving the conductivity of the negative electrode active material. Such a conductive material is not particularly limited as long as it does not cause a chemical change in the battery and is conductive. Examples of such materials that can be used include graphite such as natural graphite or artificial graphite; carbon black such as acetylene black, Ketjen black, channel black, furnace black, lamp black, and thermal black; conductive fibers such as carbon fibers and metal fibers; metal powders such as carbon fluoride, aluminum, and nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; and conductive materials such as polyphenylene derivatives.

[0215] The conductive material may be included in the negative electrode slurry in an amount of 1% by weight or more, 20% by weight or less, 15% by weight or less, or 10% by weight or less, relative to the total weight of the solids other than the solvent.

[0216] The solvent may include water or an organic solvent such as NMP (N-methyl-2-pyrrolidone), and can be used in an amount that results in a desirable viscosity when the negative electrode active material and, selectively, a binder and conductive material are included. For example, the solid content including the negative electrode active material and, selectively, the binder and conductive material may be included in amounts of 50% by weight or more, 60% by weight or more, 70% by weight or more, 95% by weight or less, 90% by weight or less, and 85% by weight or less.

[0217] When using a metal itself as the negative electrode, it can be manufactured by physically bonding, rolling, or vapor-depositing the metal onto the metal thin film itself or onto the negative electrode current collector. The vapor deposition method can be either electro-deposition or chemical vapor deposition.

[0218] For example, the metal bonded / rolled / deposited onto the metal thin film itself or onto the negative electrode current collector may include one metal or an alloy of two metals selected from the group consisting of lithium (Li), nickel (Ni), tin (Sn), copper (Cu), and indium (In).

[0219] (3) Solid electrolyte layer The solid electrolyte layer may further contain a binder in addition to the solid electrolyte containing the compound according to the present invention.

[0220] The aforementioned binder is a component that helps to bond solid electrolyte particles together. Examples of such binders include polyvinylidene fluoride, polyvinyl alcohol, carboxymethylcellulose, starch, hydroxypropylcellulose, regenerated cellulose, polyvinylpyrrolidone, tetrafluoroethylene, polyethylene, polypropylene, ethylene-propylene-diene monomer, sulfonated ethylene-propylene-diene monomer, styrene-butadiene rubber, fluororubber, and various copolymers thereof.

[0221] The binder may be included in an amount of 0.1% by weight or more, 5% by weight or less, 3% by weight or less, or 2% by weight or less, relative to the total weight of the solid electrolyte layer.

[0222] The present invention provides a battery module and a battery pack containing the all-solid-state battery as a unit cell. Since the battery module and battery pack include the secondary battery having high capacity, high rate-limiting characteristics and cycle characteristics, they can be used as a power source for medium to large devices selected from the group consisting of electric vehicles, hybrid electric vehicles, plug-in hybrid electric vehicles and power storage systems.

[0223] Hereinafter, embodiments of the present invention will be described in detail so that they can be easily implemented by a person with ordinary skill in the art to which the present invention pertains. However, the present invention can be realized in a variety of different forms, and the following embodiments are illustrative to aid in understanding the present invention and do not limit the scope of the present invention. It will be obvious to a person of ordinary skill that various changes and modifications are possible within the scope of the scope and technical idea described herein, and it goes without saying that such variations and modifications fall within the claims of this specification.

[0224] Synthesis Example 1. Preparation of the compound represented by chemical formula a-1-1 A solution containing 1 equivalent of 4-methylanisole, 1.3 equivalents of p-formaldehyde, and 50 equivalents of HCl (6N aqueous solution) was heated and stirred at 80°C for 5 hours. After cooling to room temperature, the precipitate was separated and dried under reduced pressure to obtain the crude substance. The crude substance was purified by silica gel column chromatography, and the primary intermediate obtained was 1,3-bis(chloromethyl)-2-methoxy-5-methylbenzene.

[0225] A 3-neck round bottom flask (3-RBF) was mixed with an ACN (Acetonitrile) / H2O solution containing 2 equivalents of Na2S2O4 and 4 equivalents of NaHCO3, and the mixture was stirred. The primary intermediate was added dropwise to the stirred mixture at a temperature of 45°C, and the reaction was terminated after confirming that the conversion was complete by TLC (Thin Layer Chromatography). After the reaction was terminated, stirring was stopped, and the aqueous layer was separated from the phase-separated mixture. The aqueous layer was then removed using a rotary evaporator under high temperature and reduced pressure conditions to obtain a salt. The salt was completely dissolved in a small amount of water and then added dropwise to MeOH to obtain a precipitate. The precipitate was dispersed in a DCE (Dichloroethane) solution, and 3 equivalents of PCl5 were added. After stirring under reflux conditions for approximately 12 hours, the resulting crude solution was filtered to remove any remaining salts. The filtered DCE solution was washed with H2O and then dried over MgSO4 to remove the solvent, yielding the compound (2-methoxy-5-methyl-1,3-phenylene)dimethanesulfonylchloride, represented by the following chemical formula a-1-1.

[0226] [ka]

[0227] Whether or not the compound represented by chemical formula a-1-1 has been synthesized is: 1 Confirmed by 1H-NMR spectroscopy (Bruker AVANCE NEO). 1 The H-NMR data is as follows:

[0228] 1H-NMR (400 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 2H), 4.67(s, 4H), 3.78(s, 3H), 2.17(s, 3H)

[0229] Synthesis Example 2 Preparation of the compound represented by chemical formula b-1 A 3-Neck Round Bottom Flask (3-Neck RBF) was mixed with an ACN / H2O solution containing 2 equivalents of Na2S2O4 and 4 equivalents of NaHCO3, and the mixture was stirred. To the stirred mixture, 1,4-bromooctafluorobutane was added dropwise at a temperature of 45°C. 19 After confirming the completion of the conversion by 1F NMR, the reaction was terminated. After the reaction was terminated, stirring was stopped and the aqueous layer was separated from the phase-separated mixture. The water was removed from this using a rotary evaporator under high temperature and reduced pressure conditions to obtain the salt. The salt was completely dissolved in a small amount of water and then added dropwise to MeOH to obtain a precipitate. This precipitate was dispersed in a DCE (Dichloroethane) solution and 3 equivalents of PCl5 were added. After stirring under reflux conditions for about 12 hours, the resulting crude solution was filtered to remove the residual salt. The filtered DCE solution was washed with H2O and dried over MgSO4 to remove the solvent, yielding 1,1,2,2,3,3,4,4-octafluorobutane-1,4-disulfonyl dichloride, represented by the following chemical formula b-1.

[0230] [ka]

[0231] Whether or not the compound represented by chemical formula b-1 has been synthesized is: 19Confirmed by 1F-NMR spectroscopy (Bruker, AVANCE NEO). The compound represented by the above chemical formula b-1. 19 The F-NMR data is as follows:

[0232] 19 F-NMR (400 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = -104.2(t, 13Hz, 4F), -118.8(t, J = 12Hz, 4F)

[0233] Synthesis Example 3 Preparation of the compound represented by the chemical formula c-1-1 Three equivalents of NaH were dissolved in a tetrahydrofuran (THF) solution containing 1 equivalent of polyethylene glycol (number average molecular weight: 200) dispersed in a 3-neck round bottom flask (RBF), and the mixture was stirred. To the stirred mixture, a THF solution containing 1,3-propane sultone was added dropwise at a temperature of 45°C. After stirring under reflux heating conditions, 1 After confirming the completion of the conversion by 1H NMR, the solution was cooled to room temperature. Then, methanol (MeOH) was added and the remaining NaH was quenched. The solvent was removed under reduced pressure using a rotary evaporator to obtain the crude substance, which was then purified by washing with hexane and ether to obtain the primary intermediate (poly(ethylene glycol)bis(sodium propane-1-sulfonate)).

[0234] The primary intermediate was dispersed in DCM (dichloromethane) solvent, and then 3 equivalents of PCl5 were added. The mixture was stirred at 40°C for approximately 12 hours to obtain a crude solution. The solvent was removed under reduced pressure using a rotary evaporator, and the solution was purified by washing with hexane and ether to obtain the secondary intermediate, (Poly(ethylene glycol)bis(Sodium propane-1-sulfonyl chloride)).

[0235] After adding 7 equivalents of an aqueous NH4OH solution to 3-Neck RBF under a nitrogen atmosphere, the mixture was stirred at room temperature. The secondary intermediate was dispersed in acetonitrile, and the dispersed solution was gradually added to the stirred mixture over 7 hours, after which the solution was stirred at 40°C for approximately 12 hours. Next, water was added, and the mixture was extracted several times with ethyl acetate. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure using a rotary evaporator, washed and purified with ether, and then dried to obtain poly(ethylene glycol)bis(propane-1-sulfonamide), a compound represented by chemical formula c-1-1.

[0236] [ka]

[0237] Whether or not the compound represented by chemical formula c-1-1 has been synthesized is: 1 Confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). 1 The H-NMR data is as follows:

[0238] 1H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.87(broad S, 4H), 3.43(m, 23H), 3.03(m, 4H), 1.89(m, 4H)

[0239] Synthesis Example 4 Preparation of the compound represented by chemical formula d-1 One equivalent of 3-sulfopropyl methacrylate potassium salt (TCI), 0.1 equivalents of DMF and THF (tetrahydrofuran) were added to a 1-Neck Round Bottom Flask (RBF), and 5.5 equivalents of thionyl chloride were gradually added dropwise while stirring. After 3 hours, the reaction was complete, and the mixture was quenched with water. The organic layer was extracted three times with dichloromethane (DCM) to obtain the organic layer. The solvent was removed under reduced pressure using a rotary evaporator to obtain 3-(chlorosulfonyl)propyl methacrylate.

[0240] [ka]

[0241] Whether or not the compound represented by chemical formula d-1 has been synthesized is: 1 Confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). 1 The H-NMR data is as follows:

[0242] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.13-5.63(s, 2H), 4.34(m, 2H), 3.79(m, 2H), 2.45(m, 2H), 1.96(s,3H)

[0243] Synthesis Example 5 Preparation of compounds represented by the chemical formula Aa A solution containing 1 equivalent of 4-methylanisole, 1.3 equivalents of p-formaldehyde, and 50 equivalents of HCl (6N aqueous solution) was heated and stirred at 80°C for 5 hours. After cooling to room temperature, the precipitate was separated and dried under reduced pressure to obtain the crude substance. The crude substance was purified by silica gel column chromatography, and the primary intermediate obtained was 1,3-bis(chloromethyl)-2-methoxy-5-methylbenzene.

[0244] A 3-neck round bottom flask (3-RBF) was mixed with an ACN (Acetonitrile) / H2O solution containing 2 equivalents of Na2S2O4 and 4 equivalents of NaHCO3, and the mixture was stirred. The primary intermediate was added dropwise to the stirred mixture at a temperature of 45°C, and the reaction was terminated after confirming that the conversion was complete by TLC (Thin Layer Chromatography). After the reaction was terminated, stirring was stopped, and the aqueous layer was separated from the phase-separated mixture. The aqueous layer was then removed using a rotary evaporator under high temperature and reduced pressure conditions to obtain a salt. The salt was completely dissolved in a small amount of water and then added dropwise to MeOH to obtain a precipitate. The precipitate was dispersed in a DCE (Dichloroethane) solution, and 3 equivalents of PCl5 were added. After stirring under reflux conditions for approximately 12 hours, the resulting crude solution was filtered to remove residual salts. The filtered DCE solution was washed with H2O and then dried over MgSO4 to remove the solvent, yielding (2-methoxy-5-methyl-1,3-phenylene)dimethanesulfonylchloride, represented by the following chemical formula Aa (similar to the compound represented by chemical formula a-1-1 produced in Synthesis Example 1).

[0245] [ka]

[0246] Whether or not a compound represented by the chemical formula Aa has been synthesized is, 1 Confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). 1 The H-NMR data is as follows:

[0247] 1H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 2H), 4.67(s, 4H), 3.78(s, 3H), 2.17(s, 3H)

[0248] Synthesis Example 6 Preparation of compounds represented by the chemical formula Ab. Under a nitrogen atmosphere, 5 equivalents of NH3 (7M in MeOH) were added to 3-Neck RBF, and the mixture was stirred at room temperature. One equivalent of the compound represented by chemical formula Aa, prepared in Synthesis Example 1, was dispersed in acetonitrile, and the dispersed solution was gradually added to the stirred substance over 7 hours. The solution was then stirred at 40°C for approximately 12 hours. Next, water was added, and the mixture was extracted several times with ethyl acetate. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure using a rotary evaporator, washed and purified with ether, and then dried to obtain (2-methoxy-5-methyl-1,3-phenylen)dimethanesulfonamide, represented by the following chemical formula Ab.

[0249] [ka]

[0250] Whether or not a compound represented by the chemical formula Ab has been synthesized is, 1 Confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). The compound represented by the chemical formula Ab. 1 The H-NMR data is as follows:

[0251] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 7.12(broad s, 4H), 6.98(s, 2H), 4.35(s, 4H), 3.78(s, 3H), 2.17(s, 3H)

[0252] Synthesis Example 7 Preparation of compounds represented by the chemical formula Ac Under a nitrogen atmosphere, 1 equivalent of NH3 (7M in MeOH) was added to 3-Neck RBF, and the mixture was stirred at room temperature. 1 equivalent of the compound represented by chemical formula Ab, prepared in Synthesis Example 2, was dispersed in acetonitrile, and the dispersed solution was gradually added to the stirred substance over 1 hour. The solution was then stirred at room temperature for approximately 24 hours. Next, water was added, and the mixture was extracted several times with ethyl acetate. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure using a rotary evaporator, washed and purified with ether, and then dried to obtain (2-methoxy-5-methyl-3-(sulfamoylmethyl)phenyl)methanesulfonylchloride, represented by the following chemical formula Ac.

[0253] [ka]

[0254] Whether or not a compound represented by the chemical formula Ac has been synthesized is: 1 Confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). 1 The H-NMR data is as follows:

[0255] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 7.12(broad s, 2H), 6.97(s, 2H), 4.67(s, 2H), 4.35(s, 2H), 3.78(s, 3H), 2.16(s, 3H)

[0256] Synthesis Example 8 Preparation of compounds represented by the chemical formula Ba Under a nitrogen atmosphere, an acetonitrile solution containing 1 equivalent of the compound represented by chemical formula Aa, prepared in Synthesis Example 1, was stirred. To this mixture, an aqueous solution containing 5 equivalents of lithium bis(trifluoromethyl)sulfonylimide was gradually added over 1 hour, and the solution was stirred at room temperature for approximately 24 hours. Next, water was added, and the mixture was extracted several times with ethyl acetate. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure using a rotary evaporator, washed and purified with ether, and then dried to obtain (2-methoxy-5-methyl-1,3-phenylene)dimethanesulfonyl chloride and lithium bis(trifluoromethyl)sulfonylimide, represented by the following chemical formula Ba.

[0257] [ka]

[0258] Whether or not a compound represented by the chemical formula Ba has been synthesized is, 1 This was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO). 1 The H-NMR data is as follows:

[0259] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 7.08(s, 2H), 4.67(s, 4H), 3.90(s, 3H), 2.17(s, 3H)

[0260] Manufacturing Example 1 Preparation of the compound represented by chemical formula 1-a Three equivalents of trimethylamine, one equivalent of the compound represented by chemical formula c-1-1, 0.2 equivalents of the compound represented by chemical formula a-1-1, and 0.8 equivalents of the compound represented by chemical formula b-1 were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding water and dichloromethane. Next, the obtained solid was washed with methanol and then vacuum dried. The vacuum-dried solid and three equivalents of ammonia solution (7M in MeOH, manufactured by Sigma-Aldrich) were dispersed in a DMF (Dimethylformamide) solution and stirred at 50°C for 24 hours. Next, the stirred solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding dichloromethane to obtain the compound represented by the following chemical formula 1-a.

[0261] [ka]

[0262] In the chemical formula 1-a, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0263] Whether or not the compound represented by the aforementioned chemical formula 1-a has been synthesized is, 1 The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 11200 g / mol, with a PDI of 1.8. 1 The H-NMR data is as follows:

[0264] 1H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 0.4H), 4.29(s, 0.8H), 3.78(s. 0.6H), 3.43(m, 23H), 3.02(m, 4H), 2.17(s, 0.6H), 1.89(m, 4H) 19 F-NMR (470 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = -113.2(t, 4F), -119.1(t, 4F)

[0265] Manufacturing Example 2 Preparation of the compound represented by chemical formula 1-b Three equivalents of trimethylamine, one equivalent of the compound represented by chemical formula c-1-1, and one equivalent of the compound represented by chemical formula a-1-1 were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding water and dichloromethane. Next, the obtained solid was washed with methanol and then vacuum dried. The vacuum-dried solid and three equivalents of ammonia solution (7M in MeOH, manufactured by Sigma-Aldrich) were dispersed in a DMF (Dimethylformamide) solution and stirred at 50°C for 24 hours. Next, the stirred solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding dichloromethane to obtain the compound represented by the following chemical formula 1-b.

[0266] [ka]

[0267] In the chemical formula 1-b, n is an integer between 1 and 20, and q is an integer between 1 and 20.

[0268] Whether or not the compound represented by the aforementioned chemical formula 1-b has been synthesized is, 1The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 7100 g / mol, with a PDI of 1.6. 1 The H-NMR data is as follows:

[0269] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 2H), 4.29(s, 4H), 3.78(s, 3H), 3.43(m, 23H), 2.43(m, 4H), 2.17(s, 3H), 1.89(m, 4H)

[0270] Manufacturing Example 3 Preparation of the compound represented by chemical formula 2-a Three equivalents of trimethylamine, one equivalent of the compound represented by chemical formula c-1-1, 0.2 equivalents of the compound represented by chemical formula a-1-1, and 0.8 equivalents of the compound represented by chemical formula b-1 were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and water and dichloromethane were added to obtain a mixture from which the precipitate was filtered off. Next, the obtained solid material was washed with methanol and then vacuum dried. The vacuum-dried solid material was dispersed in anhydrous DMF, and five equivalents of lithium hydride were gradually added and stirred at room temperature for 24 hours. Next, the unreacted lithium hydride was filtered off, and the precipitate was filtered off the filtrate using an excess amount of tetrahydrofuran (THF).

[0271] The precipitate obtained by the aforementioned filtration separation and 3 equivalents of ammonia solution (7M in MeOH, manufactured by Sigma-Aldrich) were dispersed in DMF (Dimethylformamide) solution and stirred at 50°C for 24 hours. Next, the stirred solution was cooled to room temperature, and dichloromethane was added to obtain a mixture from which the precipitate was separated by filtration to obtain the compound represented by the following chemical formula 2-a.

[0272] [ka]

[0273] In the chemical formula 2-a, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0274] Whether or not the compound represented by the aforementioned chemical formula 2-a has been synthesized is, 1 The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 12400 g / mol, and the PDI was 1.9. 1 The H-NMR data is as follows:

[0275] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 0.4H), 4.64(s, 0.4H), 3.78(s. 0.6H), 3.43(m, 23H), 3.32(m, 4H), 2.17(s, 0.6H), 1.89(m, 4H) 19 F-NMR (470 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = -114.1(t, 4F), -119.1(t, 4F)

[0276] Manufacturing Example 4 Preparation of the compound represented by chemical formula 2-b Three equivalents of trimethylamine, one equivalent of the compound represented by chemical formula c-1-1, and one equivalent of the compound represented by chemical formula a-1-1 were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and water and dichloromethane were added to obtain a mixture from which the precipitate was filtered off. Next, the obtained solid material was washed with methanol and then vacuum dried. The vacuum-dried solid material was dispersed in anhydrous DMF, and five equivalents of lithium hydride were gradually added and stirred at room temperature for 24 hours. Next, the unreacted lithium hydride was filtered out, and the precipitate was filtered off the filtrate using an excess amount of tetrahydrofuran (THF).

[0277] The precipitate obtained by the aforementioned filtration separation and 3 equivalents of ammonia solution (7M in MeOH, manufactured by Sigma-Aldrich) were dispersed in DMF (Dimethylformamide) solution and stirred at 50°C for 24 hours. Next, the stirred solution was cooled to room temperature, and dichloromethane was added to obtain a mixture from which the precipitate was separated by filtration to obtain the compound represented by the following chemical formula 2-b.

[0278] [ka]

[0279] In the aforementioned chemical formula 2-b, n is an integer between 1 and 20, and q is an integer between 1 and 20.

[0280] Whether or not the compound represented by the aforementioned chemical formula 2-b has been synthesized is, 1The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 7300 g / mol, with a PDI of 1.6. 1 The H-NMR data is as follows:

[0281] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 2H), 4.29(s, 4H), 3.78(s, 3H), 3.43(m, 23H), 3.33(m, 4H), 2.17(s, 3H), 1.89(m, 4H)

[0282] Manufacturing Example 5 Preparation of compounds represented by chemical formula 1-c After producing the compound represented by chemical formula 1-a in the above production example 1, 3 equivalents of TEA, 1 equivalent of the compound represented by chemical formula 1-a, and 2.5 equivalents of the compound represented by chemical formula d-1 were dispersed in a DMF solution and stirred at room temperature for 24 hours. Next, dichloromethane was added, and the precipitate from the resulting mixture was filtered to obtain the compound represented by the following chemical formula X.

[0283] [ka]

[0284] In the chemical formula 1-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0285] Whether or not the compound represented by the aforementioned chemical formula 1-c has been synthesized is, 1The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 15,000 g / mol, and the PDI was 1.9. 1 The H-NMR data is as follows:

[0286] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 0.4H), 6.0(s, 2H), 5.6(s, 2H), 4.29(s, 0.8H), 3.78(s. 0.6H), 3.43(m, 31H), 3.02(m, 8H), 2.1(s, 6.6H), 1.89(m, 4H) 19 F-NMR (470 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = -113.2(t, 4F), -119.1(t, 4F)

[0287] Manufacturing Example 6 Preparation of the compound represented by chemical formula 2-c After producing the compound represented by chemical formula 2-a in the above production example 3, 3 equivalents of TEA, 1 equivalent of the compound represented by chemical formula 2-a, and 2.5 equivalents of the compound represented by chemical formula d-1 were dispersed in a DMF solution and stirred at room temperature for 24 hours. Next, dichloromethane was added, and the precipitate from the resulting mixture was filtered to obtain the compound represented by the following chemical formula 2-c.

[0288] [ka]

[0289] Whether or not the compound represented by the aforementioned chemical formula 2-c has been synthesized is, 1The compound was confirmed by 1H-NMR spectroscopy (Bruker, AVANCE NEO) and GPC (Waters, e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 15200 g / mol, with a PDI of 1.9. 1 The H-NMR data is as follows:

[0290] 1 H-NMR (500 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = 6.99(s, 0.4H), 6.0(s, 2H), 5.6(s, 2H), 4.64(s, 0.4H), 3.78(s. 0.6H), 3.43(m, 27H), 3.32(m, 8H), 2.4(m, 4H), 2.17(s, 6.6H), 1.89(m, 4H) 19 F-NMR (470 MHZ. d6-Dimethyl sulfoxide): δ(ppm) = -114.1(t, 4F), -119.1(t, 4F)

[0291] Manufacturing example 7 Preparation of the compound represented by the chemical formula W-1 Three equivalents of trimethylamine, one equivalent of the compound represented by chemical formula Aa, and one equivalent of the compound represented by chemical formula Ab were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding water and dichloromethane. Next, the obtained solid was washed with methanol and then vacuum dried. The vacuum-dried solid and three equivalents of ammonia solution (7M in MeOH, manufactured by Sigma-Aldrich) were dispersed in a DMF (Dimethylformamide) solution and stirred at 50°C for 24 hours. Next, the stirred solution was cooled to room temperature, and the precipitate was filtered off from the mixture obtained by adding dichloromethane to obtain the compound represented by the following chemical formula W-1.

[0292] [ka]

[0293] In the chemical formula W-1, n is an integer between 1 and 300.

[0294] The presence or absence of the compound represented by the chemical formula W-1 was confirmed by GPC (Waters e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 9600 g / mol, and the PDI was 1.9.

[0295] Manufacturing Example 8 Preparation of the compound represented by chemical formula X-1 Under a nitrogen atmosphere, an acetonitrile solution containing 1 equivalent of the compound represented by chemical formula W-1, prepared in Production Example 1, was stirred. An aqueous solution containing 5 equivalents of lithium bis(trifluoromethyl)sulfonylimide was gradually added to the mixture over 1 hour, and the solution was stirred at room temperature for approximately 24 hours. Next, water was added, and the mixture was extracted several times with ethyl acetate. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure using a rotary evaporator, washed and purified with ether, and then dried to obtain the compound represented by the following chemical formula X-1.

[0296] [ka]

[0297] In the chemical formula X-1, n is an integer between 1 and 300.

[0298] The presence or absence of the compound represented by the aforementioned chemical formula X-1 was confirmed by GPC (Waters e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 9900 g / mol, and the PDI was 1.9.

[0299] Manufacturing Example 9 Preparation of the compound represented by chemical formula Z-1 Under a nitrogen atmosphere, the substance represented by chemical formula X-1, prepared in Production Example 1, was dispersed in anhydrous DMF. Then, 5 equivalents of lithium hydride were gradually added, and the solution was stirred at room temperature for approximately 24 hours. Next, the unreacted lithium hydride was filtered out, and the precipitate was separated from the resulting filtrate using an excess amount of tetrahydrofuran (THF) to obtain the compound represented by the following chemical formula Z-1.

[0300] [ka]

[0301] In the chemical formula Z-1, n and m are each an integer between 1 and 300, independently of each other.

[0302] The presence or absence of the compound represented by the chemical formula Z-1 was confirmed by GPC (Waters e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 10200 g / mol, and the PDI was 1.9.

[0303] Manufacturing Example 10 Preparation of compounds represented by chemical formula Q Three equivalents of trimethylamine, one equivalent of (2,5-dimethyl-1,3-phenylene)dimethanesulfonamide, and one equivalent of (2,5-dimethyl-1,3-phenylene)dimethanesulfonyl chloride were dispersed in a DMF (Dimethylformamide) solution and stirred at 120°C for 24 hours. Next, the solution was cooled to room temperature, and water and dichloromethane were added to obtain a mixture from which the precipitate was separated by filtration. The obtained solid was then washed with methanol and vacuum-dried to obtain the compound represented by the following chemical formula Q.

[0304] [ka]

[0305] In the chemical formula Q, n is an integer between 1 and 300.

[0306] The presence or absence of the compound represented by the aforementioned chemical formula Q was confirmed by GPC (Waters e2695 GPC). The number-average molecular weight (Mn) was analyzed to be 6100 g / mol, and the PDI was 1.7.

[0307] Example 1 Three g of the compound represented by chemical formula 1-a, produced in Production Example 1, was dispersed in 30 mL of N-methyl-2-pyrrolidone solvent to obtain a clear solution. This solution was then uniformly cast onto a flat glass plate. Next, it was dried at 40°C for approximately 12 hours, and then dried in a vacuum oven at 70°C for 24 hours. This produced an ion-conductive polymer electrolyte film with a thickness of 20-40 μm.

[0308] Example 2 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 1, except that 3 g of the compound represented by chemical formula 1-b, which was produced from Manufacturing Example 2, was used.

[0309] Example 3 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 1, except that 3 g of the compound represented by chemical formula 2-a, which was produced from Manufacturing Example 3, was used.

[0310] Example 4 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 1, except that 3 g of the compound represented by chemical formula 2-b, which was produced from Manufacturing Example 4, was used.

[0311] Example 5 Lithium bis(trifluoromethyl)sulfonylimide (EO:Li +After dissolving the compound (molar ratio = 20:1) in N-methyl-2-pyrrolidone, 3 g (20 wt% vs n-methyl-2-pyrrolidone) of the compound represented by chemical formula 1-a prepared in Production Example 1 was added. The mixture was stirred for 2 hours at room temperature using an overhead stirrer. Next, the mixture was sonicated for 20 minutes using a bath sonicator (exposed to sonication conditions) to remove bubbles and obtain a solution in which the compound represented by the following chemical formula 3-a was dissolved.

[0312] [ka]

[0313] In the chemical formula 3-a, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0314] Subsequently, the solution was uniformly spread on a flat glass plate, and solution casting was performed. Next, it was dried at a temperature of 40°C for about 12 hours, and then dried again at a temperature of 70°C in a vacuum oven for 24 hours to produce an ion-conducting polymer electrolyte film with a thickness of 20-40 μm.

[0315] Example 6 An ion-conducting polymer electrolyte film containing the compound represented by the following chemical formula 4-a was produced in the same manner as in Example 5, except that 3 g of the compound represented by chemical formula 2-a, produced from Production Example 3, was used instead of the compound represented by chemical formula 1-a.

[0316] [ka]

[0317] In the chemical formula 4-a, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

[0318] Example 7 Three g of the compound represented by chemical formula 1-c, produced in Production Example 5, was dispersed in 30 mL of N-methyl-2-pyrrolidone solvent to obtain a clear solution, to which 0.1 g of AINB was added. Next, the solution was uniformly cast onto a flat glass plate. Then, it was dried at 40°C for about 12 hours, and subsequently dried in a vacuum oven at 70°C for 24 hours. This produced an ion-conductive polymer electrolyte film with a thickness of 20-40 μm.

[0319] Example 8 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 7, except that instead of adding 0.1 g of AINB as in Example 7, 0.1 g of AINB and 0.5 g of PETA were added.

[0320] Example 9 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 7, except that 3 g of the compound represented by chemical formula 2-c, which was produced from Manufacturing Example 6, was used.

[0321] Example 10 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 8, except that 3 g of the compound represented by chemical formula 2-c, which was produced from Manufacturing Example 6, was used.

[0322] Example 11 Three g of the compound represented by chemical formula W-1, produced in Production Example 7, was dispersed in 30 mL of N-methyl-2-pyrrolidone solvent to obtain a clear solution. This solution was then uniformly cast onto a flat glass plate. Next, it was dried at 40°C for approximately 12 hours, and then dried in a vacuum oven at 70°C for 24 hours. This produced an ion-conducting polymer electrolyte film with a thickness of 20-40 μm.

[0323] Example 12 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 11, except that 3 g of the compound represented by chemical formula X-1, which was produced from Manufacturing Example 8, was used.

[0324] Example 13 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 11, except that 3 g of the compound represented by chemical formula Z-1, which was produced from Manufacturing Example 9, was used.

[0325] Comparative Example 1 Lithium bis(trifluoromethyl)sulfonylimide (EO:Li +After dissolving a molar ratio of 20:1 in acetonitrile, 3 g of PEO (20 wt% vs acetonitrile) was added. Here, the PEO had a composition of mixing PEO with Mw=100,000 (manufactured by Sigma-Aldrich) and PEO with Mw=600,000 (manufactured by Sigma-Aldrich) in a weight ratio of 9:1. The mixture was stirred for 2 hours at room temperature using an overhead stirrer. Next, it was sonicated for 20 minutes using a bath sonicator (exposed to sonication conditions) to remove air bubbles and obtain a PEO-LiTFSI solution. Next, the PEO-LiTFSI solution was dropwise added to an MRF-38 shaped film using a film applicator and coated. First, the material was dried at room temperature for approximately 12 hours, and then vacuum-dried in a vacuum oven at 40°C for 8 hours. This process produced PEO-LiTFSI polymer electrolyte films with a thickness of 10-50 μm.

[0326] Comparative Example 2 An ion-conducting polymer electrolyte film was manufactured in the same manner as in Example 11, except that 3 g of the compound represented by chemical formula Q, which was produced from Manufacturing Example 10, was used.

[0327] Experimental Example 1 - Measurement of Ionic Conductivity Inside a glove box, the polymer electrolyte films produced in the above examples and comparative examples were immersed in an EC / PC (1:1 volume ratio) solvent, and the polymer electrolyte films were interposed between two stainless steel electrodes (used as the negative and positive electrodes) inside a battery case to produce a coin cell containing the electrode assembly.

[0328] The impedance of the manufactured coin cell was measured using a potentiostat (Biologics SP-200) at room temperature (25°C) with an amplitude of 10 mV and a measurement frequency range of 0.1 Hz to 7 MHz. The ionic conductivity was then measured by substituting the values ​​into the formula L = I / RS (L = ionic conductivity, I = electrode thickness, R = measured impedance value, S = electrode area). The measured ionic conductivity values ​​are shown in Table 1 or Table 2 below.

[0329] Experimental Example 2 - Measurement of Lithium Ion Transport Saturation In a glove box, the polymer electrolyte film produced in the above examples and comparative examples was immersed in an EC / PC (1:1 volume ratio) solvent. A coin cell was then produced containing an electrode assembly in which the polymer electrolyte film was interposed between 200 μm thick lithium foil electrodes (used as the negative and positive electrodes) in a battery case and stored at a temperature of 60°C for approximately 12 hours.

[0330] The resistance of the passivation layer of the manufactured coin cell was measured before and after chronoamperometry experiments using a potentiostat (Biologics SP-200). Li+ =I s (△VI o R o ) / I o (△VI S R S )(△V = voltage applied to cell = 3mV, I o =Initial current, I S = Steady-state current, R o = Initial resistance of the passivation layer on the lithium electrode surface, R S Substitute the following into the equation for the steady-state resistance of the passivation layer on the lithium electrode surface: lithium ion transport fraction (t Li+ The lithium ion transport fraction was measured. The measured lithium ion transport fraction is shown in Table 1 or Table 2 below.

[0331] Experimental Example 3 - Tensile Strength and Tensile Strain Rate The tensile strength and tensile strain of the films produced in Examples 7-10 and Comparative Example 1 were measured using static materials testing machines (measuring instruments) manufactured by ZwickiLine, and the results are shown in Table 2 below. Specifically, test pieces cut to a width of 10 mm and a length of 30 mm were fixed to the measuring instruments, and the force at the moment of breakage and the change in the length of the test piece were measured while the test piece was pulled at a speed of 5 mm per minute. Tensile strength refers to the value obtained by dividing the force at which strain or fracture occurs by the cross-sectional area of ​​the test piece before strain occurs, and tensile strain refers to the change in the length of the test piece in response to the applied force.

[0332] [Table 1]

[0333] Referring to Table 1, it can be confirmed that Examples 3 to 6 exhibit higher levels of lithium ion conductivity and ion transportability compared to Comparative Example 1. Furthermore, it can be confirmed that Examples 1 and 2 exhibit lithium ion conductivity and ion transportability at a level equivalent to or higher than Comparative Example 1. The above examples include ion-conducting polymers in which sulfonimide anions, which are affinity for lithium ions and have low electron density, are fixed to the main chain. Since such ion-conducting polymers can transport dissociated lithium ions within the electrolyte with higher efficiency, the above examples can have higher ion conductivity and ion transportability characteristics compared to the comparative example containing a conventional alkylene oxide polymer.

[0334] Furthermore, it can be confirmed that Example 1, which uses the compound represented by chemical formula 1-a, has higher ionic conductivity and ionic transportability than Example 2, which uses the compound represented by chemical formula 1-b, and that Example 3, which uses the compound represented by chemical formula 2-a, has higher ionic conductivity and ionic transportability than Example 4, which uses the compound represented by chemical formula 2-b. This is thought to be because the highly electronegative fluorine delocalizes the anions of adjacent sulfonimides, lowering the electron density of the sulfonimides, which in turn relaxes the electrostatic attraction between lithium ions and the solid electrolyte, and consequently allows the dissociated lithium ions to move more efficiently within the electrolyte.

[0335] Furthermore, referring to Table 1, it can be confirmed that Examples 11-13 exhibit superior ionic conductivity and lithium ion transportability compared to Comparative Examples 1 and 2. In particular, Example 13 is confirmed to be at a far superior level compared to Comparative Examples 1 and 2. The compounds contained in the solid electrolytes of Examples 11-13 have an aromatic ring structure in which an alkoxy group is substituted at one carbon position of the benzene ring, and alkyl groups substituted with sulfonyl groups are located at both ortho positions, thus possessing a lithium-friendly structure, and thus exhibiting superior ionic conductivity and ion transportability. In particular, the compound contained in the solid electrolyte of Example 13 has an ionic conductive structure in which a sulfonimide anion is fixed to the main chain, allowing for more efficient transport of dissociated lithium ions. As a result, Examples 11-13 can have higher ionic conductivity and ion transportability compared to Comparative Example 2, which does not contain the alkoxy group, and Comparative Example 1, which contains a conventional alkylene oxide polymer.

[0336] [Table 2]

[0337] Referring to Table 2, it can be confirmed that Examples 9 and 10 exhibit higher levels of lithium ion conductivity and ion transport fraction compared to Comparative Example 1. Furthermore, Examples 7 and 8 also exhibit higher levels of lithium ion transport fraction compared to Comparative Example 1. The above examples include ion-conducting polymers in which sulfonimide anions, which are affinity for lithium ions and have low electron density, are fixed to the main chain. Such ion-conducting polymers can transport dissociated lithium ions within the electrolyte with greater efficiency. Therefore, the above examples can exhibit higher ion conductivity and ion transport fraction characteristics compared to comparative examples containing conventional alkylene oxide polymers.

[0338] Furthermore, it can be confirmed that Example 9, which uses the compound represented by chemical formula 2-c, has higher ionic conductivity and ionic transportability than Example 7, which uses the compound represented by chemical formula 1-c, and that Example 10, to which the crosslinking compound PETA was added, has a slightly lower lithium ion transportability than Example 9, to which PETA was not added. This is because a network was formed by radical reactions between double bonds, and by forming a solid electrolyte structure, the durability of physical strength such as tensile strength and tensile strain rate was increased, while maintaining structural uniformity and not significantly reducing the ionic conductivity and transportability of lithium ions.

[0339] Experimental Example 4 - Evaluation of Battery Life Characteristics In a glove box, the polymer electrolyte film produced in the above examples and comparative examples was immersed in an EC / PC (1:1 volume ratio) solvent. A coin cell was then produced containing an electrode assembly in which the polymer electrolyte film was interposed between 200 μm thick lithium foil electrodes (used as the negative and positive electrodes) in a battery case and stored at 60°C for approximately 12 hours.

[0340] The aforementioned coin cell was charged and discharged in a charger / discharger at 25°C, producing a discharge rate of 0.2 mA / cm². 2The coin cell was charged to cutoff at a current density of 1.0 mA / cm² for 1 hour, and then discharged for 1 hour, which constituted one cycle. Three such charge-discharge cycles were performed. Subsequently, the coin cell was charged and discharged using a charger at 1.0 mA / cm². 2 The charge-discharge process was performed 400 times, with one cycle consisting of charging to cutoff for 1 hour at a current density of 1.0 mA / cm² and then discharging for 1 hour. 2 At that time, measure the voltage generated in the first cycle, and the current density is 1.0 mA / cm². 2 Table 3 below shows the cycle number in which a voltage 1.5 times higher than the voltage generated in the first cycle is generated.

[0341] [Table 3]

[0342] Referring to Table 3, it can be confirmed that Examples 1 to 13 suppress the voltage rise compared to Comparative Examples 1 and 2, that is, the lifespan of batteries to which lithium metal negative electrodes are applied is improved. In particular, in Examples 3 to 6, 9, 10 and 13, in which lithiumization or the application of an ion-conducting polymer containing a lithium compound was performed, the effect of improving lifespan was found to be remarkably superior. This is thought to be due to the improvement of ion conductivity and ion transportability, as well as the effect of the compound containing the ion-conducting polymer according to the present invention suppressing the increase in electrode surface resistance and preventing the formation of dendritic crystals on the lithium metal electrode surface.

Claims

1. A compound that contains a repeating unit represented by the following chemical formula 1, or a lithium salt thereof. 【Chemistry 1】 In the aforementioned chemical formula 1, Each of the aforementioned X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-1, b, and c-1. The aforementioned n is an integer from 1 to 100. The aforementioned q is an integer between 1 and 100. The above o is an integer from 0 to 100, The aforementioned * is a connecting portion or terminal portion between repeating units, 【Chemistry 2】 In the aforementioned chemical formulas a-1, b, and c-1, The aforementioned R １ , R ２ and R ３ These are, independently, hydrogen; halogens; -CN; -NO ２ ; substituted or unsubstituted C １ -C １０ alkyl group; substituted or unsubstituted C １ -C １０ alkoxy group; substituted or unsubstituted C ２ -C １０ alkenyl group; substituted or unsubstituted C ２ -C １０ alkynyl group; -C(=O)R ５ ; -P(=O)(OR ５ ) ２ ; -P(OR ５ )(OR ６ ); -OP(=O)(OR ５ )(OR ６ ); -S(=O)R ５ ; or -S(=O) ２ R ５ and is The aforementioned R ４ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, The aforementioned R ５ and R ６ These are, independently, the element hydrogen; and substituted or unsubstituted C. １ -C １０ alkyl groups; or substituted or unsubstituted C ２ -C １０ It is an alkenyl group, Said L １ , L ２ and L ３ Each is independently a direct bond; or a substitution or non-substitution of C １ -C １０ It is an alkylene group, The aforementioned X １ and X ２ These are, independently, hydrogen; halogens; -CN; -NO ２ ; Substitute or non-substitute C １ -C １０ alkyl groups; or substituted or unsubstituted C ６ -C １２ It is an aryl group, The aforementioned m is an integer from 1 to 40. The value of p is an integer between 1 and 200.

2. The compound according to claim 1, wherein at least one of X, Y, and Z comprises the chemical formula a-1.

3. The aforementioned R ２ and R ４ Each of them is independent of C １ -C ５ The compound according to claim 1, wherein the alkyl group is...

4. Said L １ , L ２ and L ３ Each of them is independent of C １ -C ５ The compound according to claim 1, wherein the alkylene group is...

5. The aforementioned X １ and X ２ The compound according to claim 1, wherein each is independently a hydrogen element; or a halogen element.

6. The aforementioned n is an integer from 1 to 20. The aforementioned q is an integer from 1 to 20. The above o is an integer from 0 to 20, The aforementioned m is an integer from 1 to 10, The compound according to claim 1, wherein p is an integer from 1 to 50.

7. The compound containing the repeating unit represented by the chemical formula 1 is the compound according to claim 1, represented by the following chemical formula 1-a or 1-b. 【Transformation 3】 【Chemistry 4】 In the chemical formulas 1-a and 1-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

8. The compound according to claim 1, wherein at least one of the terminal sites contains one or more functional groups selected from the group consisting of the following chemical formulas d to g. 【Transformation 5】 In the above chemical formulas d to g, The aforementioned R ７ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, The aforementioned R ８ ~R １１ These are, independently, direct bonds; substitutional or non-substitutional C. １ -C １０ an alkylene group; or -R １２ -O-R １３ - and The aforementioned R １２ and R １３ Each is independently a direct bond; or a substitution or non-substitution of C １ -C １０ It is an alkylene group, The asterisk (*) indicates the bonding position.

9. The aforementioned R ７ C １ -C ６ It is an alkyl group, The aforementioned R ８ ~R １１ Each is independently directly bonded; C is substituted or unsubstituted with fluorine. １ -C ６ an alkylene group; or -R １２ -O-R １３ - and The aforementioned R １２ and R １３ Each is independently directly bonded: or substituted or unsubstituted with fluorine. １ -C ６ The compound according to claim 8, wherein the alkylene group is...

10. The compound is the compound according to claim 8, represented by the following chemical formula 1-c. 【Transformation 6】 In the chemical formula 1-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

11. The compound according to claim 1, wherein the lithium salt comprises a repeating unit represented by the following chemical formula 2. 【Transformation 7】 In the aforementioned chemical formula 2, Each of the aforementioned X, Y, and Z is independently selected from the group consisting of the following chemical formulas a-1, b, and c-1. The aforementioned n is an integer from 1 to 100. The aforementioned q is an integer between 1 and 100. The above o is an integer from 0 to 100, The aforementioned * is a connecting portion or terminal portion between repeating units, 【Transformation 8】 In the aforementioned chemical formulas a-1, b, and c-1, The aforementioned R １ , R ２ and R ３ These are, independently, hydrogen; halogens; -CN; -NO ２ ; substituted or unsubstituted C １ -C １０ alkyl group; substituted or unsubstituted C １ -C １０ alkoxy group; substituted or unsubstituted C ２ -C １０ alkenyl group; substituted or unsubstituted C ２ -C １０ alkynyl group; -C(=O)R ５ ; -P(=O)(OR ５ ); -P(OR ２ )(OR ５ ); -OP(=O)(OR ６ )(OR ５ ); -S(=O)R ６ ; or -S(=O) ５ R ２ R ５ wherein The aforementioned R ４ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, The aforementioned R ５ and R ６ These are, independently, the element hydrogen; and substituted or unsubstituted C. １ -C １０ alkyl groups; or substituted or unsubstituted C ２ -C １０ It is an alkenyl group, Said L １ , L ２ and L ３ Each is independently a direct bond; or a substitution or non-substitution of C １ -C １０ It is an alkylene group, The aforementioned X １ and X ２ These are, independently, hydrogen; halogens; -CN; -NO ２ ; Substitute or non-substitute C １ -C １０ alkyl groups; or substituted or unsubstituted C ６ -C １２ It is an aryl group, The aforementioned m is an integer from 1 to 40. The value of p is an integer between 1 and 200.

12. The compound containing the repeating unit represented by the chemical formula 2 is the compound according to claim 11, represented by the following chemical formula 2-a or 2-b. 【Chemistry 9】 【Chemistry 10】 In the chemical formulas 2-a and 2-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

13. The compound according to claim 11, wherein at least one of the terminal portions contains one or more functional groups selected from the group consisting of the following chemical formulas d to g. 【Chemistry 11】 In the above chemical formulas d to g, The aforementioned R ７ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, The aforementioned R ８ ~R １１ These are, independently, direct bonds; substitutional or non-substitutional C. １ -C １０ an alkylene group; or -R １２ -O-R １３ - and The aforementioned R １２ and R １３ Each is independently a direct bond; or a substitution or non-substitution of C １ -C １０ It is an alkylene group, The asterisk (*) indicates the bonding position.

14. The compound containing the repeating unit represented by the chemical formula 2 is the compound according to claim 13, represented by the following chemical formula 2-c. 【Chemistry 12】 In the chemical formula 2-c, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

15. A complex comprising the compound described in claim 1 and a lithium compound.

16. The lithium compounds mentioned above are LiCl, LiBr, LiI, and LiBF. ４ LiClO ４ LiB １０ Cl １０ LiAlCl ４ LiAlO ４ LiPF ６ LiCF ３ SO ３ LiCH ３ CO ２ LiCF ３ CO ２ LiAsF ６ LiSbF ６ LiCH ３ SO ３ , LiFSI (Lithium bis(fluorosulfonyl)imide, LiN(SO ２ F) ２ ), LiBETI (lithium bisperfluoroethanesulfonimide, LiN(SO ２ CF ２ CF ３ ) ２ and LiTFSI(lithium(bis)trifluromethanesulfonimide, LiN(SO ２ CF ３ ) ２ The composite according to claim 15, which is one or more selected from the group consisting of ).

17. The composite according to claim 15, wherein the composite is represented by one or more selected from the group consisting of the following chemical formulas 3-a, 4-a, and 4-b. 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 In the chemical formulas 3-a, 4-a, and 4-b, n is an integer between 1 and 20, q is an integer between 1 and 20, and o is an integer between 1 and 20.

18. A solid electrolyte comprising one or more selected from the group consisting of the compound described in claim 1 and the complex described in claim 15.

19. The solid electrolyte according to claim 18, further comprising a crosslinkable compound.

20. An all-solid-state battery comprising the solid electrolyte described in claim 19.

21. A compound represented by the following chemical formula A. 【Chemistry 16】 In the aforementioned chemical formula A, The aforementioned R ２１ , R ２２ and R ２３ These are, independently, hydrogen; halogens; and substituted or unsubstituted C. １ -C １０ alkyl groups; substituted or unsubstituted C １ -C １０ Alkoxy groups of; substituted or unsubstituted C ２ -C １０ alkenyl group of; or substituted or unsubstituted C ２ -C １０ It is an alkynyl group, The aforementioned R ２４ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, Said L ２１ and L ２２ These are, independently, substitutional or non-substitutional C. １ -C １０ The alkylene group; -P(=O)(OR ２５ )-;-(C=O)-;-(S=O)-; or -S(=O) ２ - and The aforementioned X ２１ and X ２２ These are, independently, halogen elements; -NH ２ ;phosphate(-OP(=O)(OR ２５ ) ２ ); Nitrate (-ON (=O) (OR ２５ )); Tosylate (-OTs); Sulfonate (-OS (=O) ２ R ２５ ); or carboxylate (-OC(=O)CH ３ ) and The aforementioned R ２５ C is either substituted or non-substituted. １ -C １０ alkyl groups; substituted or unsubstituted C ２ -C １０ alkenyl group of; or substituted or unsubstituted C ２ -C １０ It is an alkynyl group.

22. The aforementioned R ２２ , R ２４ and R ２５ Each of them is independent of C １ -C ５ The compound according to claim 21, wherein the alkyl group is...

23. Said L ２１ and L ２２ is -S (=O) ２ - The compound according to claim 21.

24. The aforementioned X ２１ and X ２２ Each is independently a halogen element or -NH ２ The compound according to claim 21.

25. The compound according to claim 21, wherein the compound represented by the chemical formula A is one or more selected from the group consisting of the following chemical formulas A-a, A-b, and A-c. 【Chemistry 17】 [Chemistry 18]

26. A complex comprising the compound described in claim 21 and a lithium compound.

27. The composite is the composite according to claim 26, represented by the following chemical formula B. 【Chemistry 19】 In the aforementioned chemical formula B, The aforementioned R ２１ , R ２２ and R ２３ These are, independently, hydrogen; halogens; and substituted or unsubstituted C. １ -C １０ alkyl groups; substituted or unsubstituted C １ -C １０ Alkoxy groups of; substituted or unsubstituted C ２ -C １０ alkenyl group of; or substituted or unsubstituted C ２ -C １０ It is an alkynyl group, The aforementioned R ２４ is the element hydrogen; or substituted or unsubstituted C １ -C １０ It is an alkyl group, Said L ２１ and L ２２ These are, independently, substitutional or non-substitutional C. １ -C １０ The alkylene group; -P(=O)(OR ２５ )-;-(C=O)-;-(S=O)-; or -S(=O) ２ - and The aforementioned X ２１ and X ２２ These are, independently, halogen elements; -NH ２ ;phosphate(-OP(=O)(OR ２５ ) ２ ); Nitrate (-ON (=O) (OR ２５ )); Tosylate (-OTs); Sulfonate (-OS (=O) ２ R ２５ ); or carboxylate (-OC(=O)CH ３ ) and The aforementioned R ２５ C is either substituted or non-substituted. １ -C １０ alkyl groups; substituted or unsubstituted C ２ -C １０ alkenyl group of; or substituted or unsubstituted C ２ -C １０ It is an alkynyl group, The aforementioned Y － is a halogen anion, BF ４ － , ClO ４ － AlCl ４ － AlO ４ － , PF ６ － CF ３ SO ３ － ,CH ３ CO ２ － CF ３ CO ２ － AsF ６ － SbF ６ － ,CH ３ SO ３ － FSI － (bis(fluorosulfonyl)imide, N(SO ２ F) ２ － ), BETI (lithium bisperfluoroethane sulfonimide, N (SO ２ CF ２ CF ３ ) ２ － ) and TFSI ((bis)trifluromethanesulfonimide, N(SO ２ CF ３ ) ２ － It is one or more selected from the group consisting of the following:

28. The composite according to claim 26, wherein the composite is one or more selected from the group consisting of the following chemical formulas B-a, B-b, and B-c. 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】

29. A polymer comprising repeating units derived from the compound described in claim 21, repeating units derived from the composite described in claim 26, or a combination thereof.

30. The polymer according to claim 29, wherein the repeating units derived from the compound according to claim 21 are represented by the following chemical formula W-a or W-b. 【Chemistry 23】 In the aforementioned chemical formulas W-a and W-b, The aforementioned n is an integer from 1 to 300. The * above indicates a connection point between repeating units.

31. The polymer according to claim 29, wherein the repeating units derived from the composite according to claim 26 are represented by the following chemical formula X-a or X-b. 【Chemistry 24】 In the aforementioned chemical formulas X-a and X-b, The aforementioned Y － is a halogen anion, BF ４ － , ClO ４ － AlCl ４ － AlO ４ － , PF ６ － CF ３ SO ３ － ,CH ３ CO ２ － CF ３ CO ２ － AsF ６ － SbF ６ － ,CH ３ SO ３ － FSI － (bis(fluorosulfonyl)imide, N(SO ２ F) ２ － ), BETI (lithium bisperfluoroethane sulfonimide, N (SO ２ CF ２ CF ３ ) ２ － ) and TFSI ((bis)trifluromethanesulfonimide, N(SO ２ CF ３ ) ２ － One or more selected from the group consisting of ) The aforementioned n is an integer from 1 to 300. The * above indicates a connection point between repeating units.

32. The polymer according to claim 29, wherein the combination of repeating units derived from the compound according to claim 21 and repeating units derived from the composite according to claim 26 is represented by the following chemical formula Y or Z. 【Chemistry 25】 In the aforementioned chemical formulas Y and Z, The aforementioned Y － is a halogen anion, BF ４ － , ClO ４ － AlCl ４ － AlO ４ － , PF ６ － CF ３ SO ３ － ,CH ３ CO ２ － CF ３ CO ２ － AsF ６ － SbF ６ － ,CH ３ SO ３ － FSI － (bis(fluorosulfonyl)imide, N(SO ２ F) ２ － ), BETI (lithium bisperfluoroethane sulfonimide, N (SO ２ CF ２ CF ３ ) ２ － ) and TFSI ((bis)trifluromethanesulfonimide, N(SO ２ CF ３ ) ２ － One or more selected from the group consisting of ) The aforementioned n and m are each independent integers between 1 and 300. The * above indicates a connection point between repeating units.

33. A solid electrolyte comprising the polymer described in claim 29.

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