Ionic organic compounds, compositions and electrolytes comprising same, and use thereof in electrochemistry

Abstract

The present technology relates to ionic organic compounds of formulas (I) and (II), the compositions and solid electrolytes comprising same, and optionally inorganic particles and a solid ionic bifunctional molecule, for use in electrochemical applications. Also described are electrochemical cells and electrochemical batteries comprising the solid electrolyte.

Description

[0001]IONIC ORGANIC COMPOUNDS, COMPOSITIONS AND ELECTROLYTES COMPRISING THEM, AND THEIR USE IN ELECTROCHEMISTRY RELATED APPLICATION The present application claims priority, under applicable law, from Canadian patent application number 3206622 filed on July 14, 2023, the content of which is incorporated herein by reference in its entirety and for all purposes. TECHNICAL FIELD The present application relates to the field of ionic organic compounds, compositions and solid electrolytes comprising them and their uses in electrochemical applications. More particularly, the present application relates to ionic organic compounds, their manufacturing processes and their uses in electrochemical cells, in particular in so-called all-solid-state batteries.STATE OF THE ART Liquid electrolytes used in lithium-ion batteries are flammable and slowly degrade to form a passivation layer on the surface of the lithium film or solid electrolyte interface (SEI) irreversibly consuming lithium, which decreases the Coulombic efficiency of the battery. In addition, lithium anodes undergo significant morphological changes during battery cycling and lithium dendrites are formed. As these generally migrate through the electrolyte, they can eventually cause short circuits.Safety concerns and the requirement for higher energy density have stimulated research for the development of an all-solid-state lithium rechargeable battery with a polymer, ceramic, or polymer-ceramic hybrid electrolyte, all three of which are more stable toward metallic lithium and reduce the growth of lithium dendrites. However, the application scope of solid electrolytes is still limited. Indeed, solid electrolytes have problems related to their limited electrochemical stability, limited interfacial stability, relatively low ionic conductivity, loss of reactivity, poor contact between solid interfaces, etc. Therefore, there is a need for the development of all-solid-state electrochemical systems excluding one or more of the disadvantages of conventional all-solid-state electrochemical systems.SUMMARY In some aspects, embodiments of the present technology comprise the following items: Item 1. Compound of Formula I or II:. in which, A- is a delocalized anion; R + is chosen from the groups -N + (R 1 R 2 R 3 ) and -P + (R 1 R 2 R 3 ); R 1 , R 2 and R 3 , when adjacent to N, are independently selected from a hydrogen atom and a C group 1-12 linear or branched alkyl or C6aryl, the alkyl or aryl group being substituted or unsubstituted, where when one of R 1 , R 2 and R 3 is a hydrogen atom then the other two are other than a hydrogen atom; R 1 , R 2 and R 3 , when adjacent to P, are independently chosen from a group C 1-12 alkyl, OC 1-12 alkyl or SC 1-12linear or branched alkyl, and a C6aryl, OC6aryl or SC6aryl group, the alkyl or aryl group being substituted or unsubstituted; or R 1 and R 2 with the nitrogen or phosphorus atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as previously defined, or R 1 , R 2 and R 3 with the nitrogen or phosphorus atom together form a partially unsaturated heteroaryl or heterocycloalkyl group with one or more rings and having from 5 to 12 members, the heteroaryl or heterocycloalkyl group being substituted or unsubstituted; L is, independently at each occurrence, a C 2-8linear or branched alkylene; X is a halogen atom; Y is O or S; m is a number greater than or equal to 1, or in the range 1 to 6; and n is an integer greater than or equal to 1, or in the range 1 to 11; preferably when the compound is of Formula I, X is Br, A- is bis(trifluoromethanesulfonyl)imide (TFSI-), R +is a 3-methyl-1-imidazolium group, then n is different from 5. Item 2. Compound according to item 1, in which A- is chosen from anions comprising a phosphate, an imide, a sulfonylimide, a sulfonate, a sulfate, a borate, a nitrate, an arsenate, or a triazolate. Item 3.Compound according to item 1 or 2, in which A- is selected from hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), 2-trifluoromethyl-4,5-dicyanoimidazolate (TDI-), 4,5-dicyano-1,2,3-triazolate (DCTA-), bis(pentafluoroethylsulfonyl)imide (BETI-), difluorophosphate (DFP-), tetrafluoroborate (BF4-), bis(oxalato)borate (BOB-), nitrate (NO3-), perchlorate (ClO4-), hexafluoroarsenate (AsF6-), trifluoromethanesulfonate (CF3SO3- or -OTf), fluoroalkylphosphate anions ([PF3(CF2CF3)3]- or FAP-), tetrakis(trifluoroacetoxy)borate ([B(OCOCF3)4]- or TFAB-), bis(1,2-benzenediolato(2-)-O,O')borate ([B(C6O2)2]- or BBB-), difluoro(oxalato)borate (BF2(C2O4)- or FOB-), and an anion of formula BF2O4R. x (R x= C2-4alkyl). Item 4. Compound according to item 3, wherein the delocalized anion is selected from hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), tetrafluoroborate (BF4-), and trifluoromethanesulfonate (CF3SO3- or -OTf). Item 5. Compound according to item 4, wherein the delocalized anion is bis(trifluoromethanesulfonyl)imide (TFSI-). Item 6. Compound one of items 1 to 5, wherein R + is a -N grouping + (R 1 R 2 R 3 ). Item 7. Compound according to item 6, in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched, substituted or unsubstituted alkyls. Item 8. Compound according to item 6, in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12linear or branched alkyls, where at least one of R 1 , R 2 , and R 3 is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group. Item 9. Compound according to item 6, in which R 1 and R 2 with the nitrogen atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as defined in item 1, preferably R 3 is a C1-12alkyl, or a C1-4alkyl. Item 10. Compound according to item 6, in which R 1 , R 2 and R 3 with the nitrogen atom together form a heteroaromatic or partially unsaturated heterocycle with one or more rings and having from 5 to 12 members. Item 11. Compound according to item 6, in which R + is chosen from the heterocycles: R 3 is as defined in item 1; R 4is a linear or branched, substituted or unsubstituted C1-12alkyl, C1-12alkenyl or C1-12alkynyl group; and R 5 is a hydrogen or halogen atom or a C group 1-12 alkyl, C 1- 12 alkenyl or C 1-12 linear or branched alkynyl, substituted or unsubstituted; the heterocycle being optionally substituted. Item 12. Compound according to item 11, in which R + is of formula: in which R 3 is such that Item 13. Compound according to one of items 1 to 9, 11 or 12, in which R 3 is a C group 1-4 unsubstituted alkyl. Item 14. Compound according to item 13, in which R 3 is selected from a methyl group, an ethyl group, an n- or i-propyl group, and an n-, i-, s- or t-butyl group. Item 15. Compound according to item 11, in which R 4 is a C group 1-4 alkyl. Item 16. Compound according to item 11 or 15, in which R 5is a hydrogen atom or a C group 1-4 alkyl. Item 17. Compound according to one of items 1 to 5, in which R + is a grouping - P + (R 1 R 2 R 3 ). Item 18. Compound according to item 17, in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched, substituted or unsubstituted alkyls. Item 19. Compound according to item 17, in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched alkyls, or at least one of R 1 , R 2 and R 3is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group. Item 20. A compound according to any of items 1 to 19, the compound being of Formula I. Item 21. A compound according to item 20, wherein n is a number in the range 2 to 10, or 3 to 8, or 4 to 6. Item 22. A compound according to any of items 1 to 19, the compound being of Formula II. Item 23. A compound according to item 22, wherein L is C 2-4 linear or branched alkylene or a C 2-3linear or branched alkylene. Item 24. Compound according to item 22 or 23, wherein Y is O. Item 25. Compound according to item 22 or 23, wherein Y is S. Item 26. Compound according to any of items 22 to 25, wherein m is a number from 1 to 4, or from 1 to 3. Item 27. Compound according to any of items 1 to 26, wherein X is Cl, Br or I, preferably Cl or Br, or X is Br. Item 28. Compound according to any of items 1 to 27, which has a melting point of 60°C or less, or 40°C or less, preferably 25°C or less. Item 29. Compound according to one of items 1 to 5, which is selected from the salts A- of 1-(6-bromohexyl)-1-methylpyrrolidinium, 1-(6-chlorohexyl)-1-methylpyrrolidinium, and 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium, preferably bis(trifluoromethanesulfonyl)imide of 1-(6-bromohexyl)-1-methylpyrrolidinium (Compound 1), of 1-(6-chlorohexyl)-1-methylpyrrolidinium (Compound 2), or of 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium (Compound 3). Item 30.Composition comprising a compound as defined in one of items 1 to 29 and an ionic bifunctional molecule. Item 31. Composition according to item 30, in which the ionic bifunctional molecule is of Formula III or IV:. in which A-, R +, L, Y, m and n are independently at each occurrence as defined in items 1 to 26. Item 32. Composition according to item 31, wherein the ionic bifunctional molecule is 1,1'-(1,6-hexamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide. Item 33. Composition according to item 31, wherein the ionic bifunctional molecule is 1,1'-(1,12-dodecamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide. Item 34. Composition according to item 31, wherein the ionic bifunctional molecule is 1,1'-(2,2′-(ethylenedioxy)diethane) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide. Item 35. Composition according to item 31, in which the ionic bifunctional molecule is 1,1'-(thiol bis(1,2-ethane)) bis(1-methylpyrrolidinum) bis(trifluoromethanesulfonyl)imide. Item 36.A composition according to item 31, wherein the ionic bifunctional molecule is 3,3'-(1,6-hexamethylene) bis(1,2-dimethylimidazolium)bis(trifluoromethanesulfonyl)imide. Item 37. A composition according to one of items 30 to 36, wherein the weight ratio of "compound:ionic bifunctional molecule" is from about 2:98 to about 50:50, or from about 5:95 to about 35:65, or from about 10:90 to about 30:70. Item 38. A composition according to one of items 30 to 37, which is solid at room temperature (e.g., 25°C ± 5°C). Item 39. Solid electrolyte comprising a compound as defined in one of items 1 to 29, or a composition as defined in one of items 30 to 38. Item 40. Solid electrolyte according to item 39, further comprising inorganic particles. Item 41.Solid electrolyte according to item 40, wherein the inorganic particles comprise a material selected from glasses, glass-ceramics, ceramics, nanoceramics and a combination of at least two of these. Item 42. Solid electrolyte according to item 41, wherein the inorganic particles comprise a ceramic, glass or glass-ceramic based on fluoride, phosphide, sulfide, oxysulfide or oxide. Item 43. Solid electrolyte according to item 41, wherein the inorganic particles comprise a compound of the LISICON, thio-LISICON, argyrodite, garnet, NASICON, perovskite, oxide, sulfide, oxysulfide, phosphide, fluoride type, in crystalline and / or amorphous form, or a combination of at least two of these. Item 44.The solid electrolyte of item 41, wherein the inorganic particles comprise a compound selected from inorganic compounds of formulae MLZO (e.g., M7La3Zr2O12, M(7-a)La3Zr2AlbO12, M(7-a)La3Zr2GabO12, M(7-a)La3Zr(2-b)TabO12, and M(7-a)La3Zr(2-b)NbbO12); MLTaO (e.g., M7La3Ta2O12, M5La3Ta2O12, and M6La3Ta1.5Y0.5O12); MLSnO (e.g., M7La3Sn2O12); MAGP (e.g., M1+aAlaGe2-a(PO4)3); MATP (e.g., M1+aAlaTi2-a(PO4)3,); MLTiO (e.g., M3aLa(2 / 3-a)TiO3); MZP (e.g., MaZrb(PO4)c); MCZP (e.g., MaCabZrc(PO4)d); MGPS (e.g., MaGebPcSd such as M10GeP2S12); MGPSO (e.g., MaGebPcSdOe); MSiPS (e.g., MaSibPcSd such as M10SiP2S12); MSiPSO (e.g., MaSibPcSdOe); MSnPS (e.g., MaSnbPcSd such as M10SnP2S12); MSnPSO (e.g., MaSnbPcSdOe); MPS (e.g., MaPbSc such as M7P3S11); MPSO (e.g., MaPbScOd); MZPS (e.g., MaZnbPcSd); MZPSO (e.g., MaZnbPcSdOe); xM2S-yP2S5; xM2S-yP2S5-zMX; xM2S-yP2S5-zP2O5; xM2S-yP2S5-zP2O5- wMX; xM2S-yM2O-zP2S5; xM2S-yM2O-zP2S5-wMX; xM2S-yM2O-zP2S5-wP2O5; xM2S-yM2O-zP2S5-wP2O5-vMX; xM2S-ySiS2; MPSX (e.g., MaPbScXd such as M7P3S11X, M7P2S8X, and M6PS5X); MPSOX (for example, MaPbScOdXe); MGPSX (MaGebPcSdXe); MGPSOX (MaGebPcSdOeXf); MSiPSX (MaSibPcSdXe); MSiPSOX (MaSibPcSdOeXf); MSnPSX (Mr.a Sn b P c S d X e ); MSnPSOX (M a Sn b P c S d O e X f ); MZPSX (M a Zn b P c S d X e ); MZPSOX (M a Zn b P c S d O e X f ); M3OX; M2HOX; M3PO4; M3PS4; et M a PO b N c(where a = 2b + 3c - 5); wherein, M is an alkali metal ion, an alkaline earth metal ion, or a combination of two or more thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality; X is selected from F, Cl, Br, I or a combination of two or more thereof and may be the same as or different from X present in the compound of Formula I or II; a, b, c, d, e and f are non-zero numbers and are, independently in each formula, selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are, independently in each formula, selected to obtain a stable compound. Item 45. Solid electrolyte according to item 44, wherein M is selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba or a combination of at least two thereof. Item 46. Solid electrolyte according to item 45, wherein M is Li. Item 47.Solid electrolyte according to one of items 44 to 46, wherein the inorganic particles comprise an inorganic compound of formula MATP. Item 48. Solid electrolyte according to one of items 44 to 46, wherein the inorganic particles comprise a sulfide or an oxysulfide. Item 49. Solid electrolyte according to one of items 44 to 46, wherein the inorganic particles comprise a compound selected from inorganic compounds of formula LiaPbScXd in which X is Cl, Br, I or a combination of at least two thereof, and a, b, c and d are such that (a + 5b) = (2c + d). Item 50. Solid electrolyte according to item 49, wherein the inorganic particles comprise Li6PS5Cl. Item 51.A solid electrolyte according to any one of items 44 to 46, wherein the inorganic particles comprise a compound selected from inorganic compounds of formula LiaPbScOdXe wherein X is Cl, Br, I or a combination of at least two thereof and a, b, c, d and e are such that (a + 5b) = (2c + 2d + e). Item 52. A solid electrolyte according to item 51, wherein a is selected from the range 5 to 6, b is 1, c is selected from the range 3.5 to 4.8, and e is selected from the range 1 to 2 (e.g. Li. 5.4 PS 4.1 O 0.3 X 1.6 or Li 5.4 PS 4.1 O 0.3 ClBr 0.5 I 0.1). Item 53. A solid electrolyte according to any one of items 40 to 52, wherein the inorganic particles are present at a concentration of about 20% to about 95%, or about 40% to about 95%, or about 60% to about 95%, by weight in the solid electrolyte. Item 54. A solid electrolyte according to any one of items 39 to 53, wherein the concentration of the compound in the electrolyte is in the range of about 0.2% to about 5% by weight, or about 0.3% to about 4% by weight, or about 0.4% to about 3% by weight. Item 55. A solid electrolyte according to any one of items 39 to 54, which further comprises a polymer. Item 56.Solid electrolyte according to item 55, wherein the polymer is a linear or branched polymer selected from polyethers, polythioethers, polyesters, polythioesters, poly(dimethylsiloxanes), poly(alkylene carbonate), poly(alkylene thiocarbonate), poly(alkylene sulfones), poly(alkylene sulfamides), polyimides, polyamides, polyphosphazenes, polyurethanes, poly(vinyl alcohols), polyacrylonitriles, polyethacrylates and polymethacrylates, and copolymers thereof. Item 57. Solid electrolyte according to item 56, wherein the polyether is poly(ethylene oxide) (PEO), poly(propylene oxide) (POP), or a copolymer (EO / PO). Item 58. Solid electrolyte according to item 56 or 57, in which the polymer comprises crosslinked units originating from crosslinkable functional groups or their crosslinked equivalents. Item 59.Solid electrolyte according to item 58, wherein the crosslinkable functional group is selected from acrylate, methacrylate, vinyl, glycidyl and mercapto functional groups. Item 60. Solid electrolyte according to item 55, wherein the polymer is the reaction product of at least one monomer comprising at least one polymerizable or crosslinkable function and a compound comprising at least one SH functional group. Item 61. Solid electrolyte according to one of items 55 to 60, wherein the polymer is present at a concentration of about 0.1% to about 20%, or about 1% to about 15%, or about 2% to about 13%, by weight in the solid electrolyte. Item 62. Solid electrolyte according to one of items 39 to 61, which further comprises an additive. Item 63. Solid electrolyte according to item 62, in which the additive is a fluorinated compound comprising an amide function. Item 64. Solid electrolyte according to item 63, in which the fluorinated compound is of formula R.6 X 6 C(O)N(H)X 7 R 7 , where R 6 and R 7 are independently alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl groups, X 6 is O, NH or absent, and X 7 is absent or is a C(O), S(O)2, or Si(R) group 8 R 9 ), where R 8 and R 9 alkyl groups, and where at least one of R 6 , R 7 , R 8 and R 9 is a group substituted by one or more fluorine atom(s). Item 65. Solid electrolyte according to item 64, in which R 6 is a perfluorinated group and X 6is absent. Item 66. An electrochemical cell comprising a negative electrode, a positive electrode, and an electrolyte, wherein the electrolyte is as defined in one of items 39 to 65. Item 67. An electrochemical cell according to item 66, wherein the positive electrode comprises a positive electrode material comprising an electrochemically active positive electrode material. Item 68. An electrochemical cell according to item 67, wherein the positive electrode material is on a current collector. Item 69. An electrochemical cell according to item 67 or 68, wherein the electrochemically active positive electrode material is selected from metal phosphates, lithium metal phosphates, metal oxides, and lithium metal oxides. Item 70.An electrochemical cell according to item 67 or 68, wherein the positive electrode electrochemically active material is LiM'PO4where M' is Fe, Ni, Mn, Co, or a combination of at least two thereof, LiV3O8, V2O5F, LiV2O5, LiMn2O4, LiM''O2, where M'' is Mn, Co, Ni, or a combination of at least two thereof (such as NMC, LiMn. x Co y Neither zO2with x+y+z = 1), Li(NiM''')O2(where M''' is Mn, Co, Al, Fe, Cr, Ti, Zr, or a combination of two or more thereof), sulfur, elemental selenium or iodine, iron(III) fluoride, copper(II) fluoride, lithium iodide, carbon-based active materials such as graphite, organic cathode active materials, or a combination of two or more thereof, when compatible with each other. Item 71. An electrochemical cell according to any one of items 67 to 70, wherein the positive electrode material further comprises an electronically conductive material, a binder, a salt, an ionic organic compound, an ionic bifunctional molecule, and / or inorganic particles. Item 72. An electrochemical cell according to any one of items 66 to 71, wherein the negative electrode comprises a negative electrode material comprising an electrochemically active negative electrode material. Item 73.An electrochemical cell according to item 72, wherein the negative electrode material is on a current collector. Item 74. An electrochemical cell according to item 72 or 73, wherein the electrochemically active negative electrode material comprises a metal film comprising an alkali or alkaline earth metal or an alloy comprising an alkali or alkaline earth metal. Item 75. An electrochemical cell of item 74, wherein the alkali metal is selected from lithium and sodium. Item 76.The electrochemical cell of item 72 or 73, wherein the negative electrode electrochemically active material comprises an intermetallic compound (e.g., SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2, and CoSn2), a metal oxide, a metal nitride, a metal phosphide, a metal phosphate (e.g., LiTi2(PO4)3), a metal halide (e.g., a metal fluoride), a metal sulfide, a metal oxysulfide, a carbon (e.g., graphite, graphene, reduced graphene oxide, hard carbon, soft carbon, exfoliated graphite, and amorphous carbon), silicon (Si), a silicon-carbon (Si-C) composite, a silicon oxide (SiO. x ), a silicon oxide-carbon composite (SiO x -C), tin (Sn), a tin-carbon composite (Sn-C), a tin oxide (SnO x), a tin oxide-carbon composite (SnOx-C), and combinations thereof, when compatible. Item 77. An electrochemical cell according to item 76, wherein the metal oxide is selected from compounds of formulae M''''bOc (where M'''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof; and b and c are numbers such that the c:b ratio is in the range of 2 to 3) (e.g., MoO3, MoO2, MoS2, V2O5, and TiNb2O7), spinel oxides (e.g., NiCo2O4, ZnCo2O4, MnCo2O4, CuCo2O4, and CoFe2O4) and LiM'''''O (where M''''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof) (e.g., a lithium titanate (such as Li4Ti5O12) or a lithium molybdenum oxide (such as Li2Mo4O13)). Item 78.An electrochemical cell according to item 76 or 77, wherein the negative electrode material further comprises an electronically conductive material, a binder, a salt, an ionic organic compound, an ionic bifunctional molecule, and / or inorganic particles. Item 79. An electrochemical accumulator comprising at least one electrochemical cell as defined in one of items 66 to 78. Item 80. An electrochemical accumulator according to item 79, wherein said electrochemical accumulator is selected from the group consisting of a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a potassium battery, a potassium-ion battery, a magnesium battery, and a magnesium-ion battery. Item 81. An electrochemical accumulator according to item 80, wherein said electrochemical accumulator is a lithium battery. Item 82.Electrochemical accumulator according to item 80, wherein said electrochemical accumulator is a lithium-ion battery. BRIEF DESCRIPTION OF THE FIGURES Figures 1(a) to 1(c) respectively present the proton NMR spectra of Compounds 1, 2 and 3, as described in Example 2. Figures 2(a) to 2(c) respectively present the results of differential scanning calorimetry (DSC) analysis obtained for Compounds 1, 2 and 3, as described in Example 3. Figures 3(a) to 3(c) respectively present the results of thermogravimetric analysis (TGA) obtained for Compounds 1, 2 and 3, as described in Example 3. Figure 4 presents the results of differential scanning calorimetry (DSC) analysis obtained for Compositions 1, 2 and A1 to A3, as described in Example 4.Figure 5 shows the measured ionic conductivity results as a function of temperature for Cells 1 (■), 2 (●), 3 (▲), 4 (▼), 5 (◄), 6 (►) and 7 ( ^), as described in Example 5(b). Figure 6 shows the measured ionic conductivity results as a function of temperature for Cells 1 (■), 3 (▲), 6 (►), 7 ( ^), 8 (∆) and 9 (♦), as described in Example 5(b). Figure 7 shows the measured ionic conductivity results as a function of temperature for Cells 1 (■), 2 (●), 10 ( ^) and 11 (▲), as described in Example 5(b). DETAILED DESCRIPTION All technical and scientific terms and expressions used herein have the same definitions as those generally understood by those skilled in the art of the present technology. Definitions of certain terms and expressions used are nevertheless provided below.When the term "about" is used herein, it means approximately, in the region of, or around. For example, when the term "about" is used in connection with a numerical value, it modifies it above and below by a variation of 10% from its nominal value. This term may also take into account, for example, the experimental error of a measuring device or rounding. When a range of values ​​is referred to in this application, the lower and upper bounds of the range are, unless otherwise indicated, always included in the definition. When a range of values ​​is referred to in this application, then all intermediate intervals and subintervals, as well as individual values ​​included in the ranges of values, are included in the definition.When the article "a" is used to introduce an element in the present application, it does not have the meaning of "a single one", but rather of "one or more". Of course, where the description states that a particular step, component, element or feature "may" or "could" be included, that particular step, component, element or feature is not required to be included in every embodiment. The chemical structures described herein are drawn following the conventions of the art. Also, where an atom, such as a carbon atom, as drawn appears to include an incomplete valency, then it is assumed that the valency is satisfied by one or more hydrogen atoms even if they are not explicitly drawn. As used herein, the term "alkyl" refers to saturated hydrocarbons having from 1 to 12 carbon atoms, including straight or branched alkyl groups.Non-limiting examples of alkyl groups may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, tert-butyl, sec-butyl, isobutyl, and so on. When the alkyl group is located between two functional groups, then the term alkyl also includes alkylene groups such as methylene, ethylene, propylene, and so on. The terms “C. m -C n alkyl" and "C m -C nalkylene" refer respectively to an alkyl or alkylene group having from the indicated number "m" to the indicated number "n" of carbon atoms. As used herein, the term "alkenyl" refers to optionally substituted unsaturated hydrocarbons having between two and twelve carbon atoms and having at least one double bond between two carbon atoms, including linear or branched alkenyl groups. Non-limiting examples of alkenyl groups may include vinyl, allyl, 1-propen-2-yl, 1-buten-3-yl, 1-buten-4-yl, 2-buten-4-yl, 1-penten-5-yl, 1,3-pentadien-5-yl, and so on. When the alkenyl group is located between two functional groups, then the term alkenyl also includes alkenylene groups such as vinylene, allylene, 1-propen-2-ylene, 1-buten-3-ylene, and so on.The terms "Cm-Cn-alkenyl" and "Cm-Cn-alkenylene" refer respectively to an alkenyl or alkenylene group having from the indicated number "m" to the indicated number "n" of carbon atoms. As used herein, the term "alkynyl" refers to unsaturated hydrocarbons having between two and twelve carbon atoms and having at least one triple bond between two carbon atoms, including straight or branched alkynyl groups. Non-limiting examples of alkynyl groups may include ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 2-butyn-4-yl, 1-pentyn-5-yl, 1,3-pentadiyn-5-yl. When the alkynyl group is located between two functional groups, then the term alkynyl also includes alkynylene groups such as ethynylene, 1-propyn-3-ylene, 1-butyn-4-ylene, and so on.The terms "Cm-Cn-alkynylene" and "Cm-Cn-alkynylene" refer, respectively, to an alkynyl or alkynylene group having from the indicated number "m" to the indicated number "n" of carbon atoms. Generally, the terms "ring" and "heterocycle" refer, respectively, to "cycloalkyl" and "aryl" groups, and to "heterocycloalkyl" and "heteroaryl" groups. As used herein, the term "cycloalkyl" as used herein refers to a group comprising one or more saturated or partially unsaturated (non-aromatic) carbocyclic rings comprising from 3 to 15 members in a monocyclic or polycyclic system, including spiro (sharing one atom), fused (sharing at least one bond), or bridged carbocycles and may be optionally substituted.Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-2-yl, cyclopenten-3-yl, cyclohexyl, cyclohexen-1-yl, cyclohexen-2-yl, cyclohexen-3-yl, cycloheptyl, and so on. When the cycloalkyl group is located between two functional groups, the term cycloalkylene may also be used. The terms “C. m -C n cycloalkyl" and "C m - C ncycloalkylene" refer to a cycloalkyl or cycloalkylene group having from the indicated number "m" to the indicated number "n" of carbon atoms, respectively. As used herein, the term "heterocycloalkyl" refers to a group comprising a saturated or partially unsaturated (non-aromatic) carbocyclic ring comprising from 3 to 15 members in a monocyclic or polycyclic ring system, including spiro (sharing one atom), fused (sharing at least one bond), or bridged carbocycles and may be optionally substituted, and having carbon atoms and from 1 to 4 heteroatoms (e.g., N, O, S, or P) or groups containing such heteroatoms (e.g., NH, NRx (Rx is an alkyl, acyl, aryl, heteroaryl, or cycloalkyl group), PO2, SO, SO2, and other similar groups). Heterocycloalkyl groups may be attached to a carbon atom or to a heteroatom (e.g. via a nitrogen atom) where possible.The term heterocycloalkyl includes both unsubstituted heterocycloalkyl groups and substituted heterocycloalkyl groups. When the heterocycloalkyl group is located between two functional groups, the term heterocycloalkylene may also be used. The terms "Cm-Cnheterocycloalkyl" and "Cm-Cnheterocycloalkylene" refer, respectively, to a heterocycloalkyl or heterocycloalkylene group having from the indicated number "m" to the indicated number "n" of ring atoms, including carbon atoms and heteroatoms. The terms "aryl" or "aromatic" refer to an aromatic group having 4n+2 conjugated π(pi) electrons in which n is a number from 1 to 3, in a monocyclic group, or a fused bicyclic or tricyclic system having a total of 6 to 15 ring members, in which at least one of the rings in a system is aromatic.The terms "aryl" or "aromatic" refer to both monocyclic and conjugated polycyclic systems. The terms "aryl" or "aromatic" also include substituted or unsubstituted groups. Examples of aryl groups include, but are not limited to, phenyl, benzyl, phenethyl, 1-phenylethyl, tolyl, naphthyl, biphenyl, terphenyl, indenyl, benzocyclooctenyl, benzocycloheptenyl, azulenyl, acenaphthylenyl, fluorenyl, phenanthrenyl, anthracenyl, perylenyl, and so on. The terms "C. m -C n aryl" and "C m -C narylene" refer respectively to an aryl or arylene group having from the indicated number "m" to the indicated number "n" of carbon atoms. The terms "heteroaryl", "heteroarylene", or "heteroaromatic" denote an aromatic group having 4n+2 conjugated π(pi) electrons in which n is a number from 1 to 3, for example having from 5 to 18 ring atoms, preferably 5, 6, or 9 ring atoms in a conjugated monocyclic or polycyclic system (fused or not); and having, in addition to carbon atoms, from 1 to 6 heteroatoms selected from oxygen, nitrogen and sulfur or groups containing such heteroatoms or groups containing such heteroatoms (for example, NH and NRx (Rx is an alkyl, acyl, aryl, heteroaryl or cycloalkyl group), SO, and other similar groups). A polycyclic ring system comprises at least one heteroaromatic ring.Heteroaryls may be directly attached, or connected through a C1-C3alkyl group (also referred to as heteroarylalkyl or heteroaralkyl). Heteroaryl groups may be attached to a carbon atom or a heteroatom of the ring (e.g., via a nitrogen atom), where possible. The terms "Cm-Cnheteroaryl" and "Cm-Cnheteroarylene" refer, respectively, to a heteroaryl or heteroarylene moiety having from the indicated number "m" to the indicated number "n" of ring atoms, including carbon atoms and heteroatoms. Generally, the term "substituted" means that one or more hydrogen atoms on the designated moiety is replaced by a suitable substituent. The substituents or combinations of substituents contemplated in this specification are those resulting in the formation of a chemically stable compound.Examples of substituents include halogen atoms (such as F, Cl, Br, I) and hydroxyl, oxo, alkyl, alkoxyl, alkoxyalkyl, nitrile, azido, aldehyde, carboxylic acid, metal or alkyl carboxylate, alkoxycarbonyl, alkylcarbonyl, primary, secondary or tertiary amine, amide, nitro, silane, siloxane, thiocarboxylate, thiol, alkylthiol, sulfonyl, sulfonic acid, metal or alkyl sulfonate, sulfonamide, metal or dialkyl phosphate, metal or dialkyl phosphonate, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, or a combination thereof. The present technology relates to an ionic organic compound of Formula I or II:. Formula I in which, A- is a delocalized anion; R + is chosen from the groups -N + (R 1 R 2 R 3 ) and -P + (R 1 R 2 R 3 ); R 1 , R 2 and R 3, when adjacent to N, are independently selected from a hydrogen atom and a C group 1-12 linear or branched alkyl or C6aryl, the alkyl or aryl group being substituted or unsubstituted, where when one of R 1 , R 2 and R 3 is a hydrogen atom then the other two are other than a hydrogen atom; R 1 , R 2 and R 3 , when adjacent to P, are independently chosen from a group C 1-12 alkyl, OC 1-12 alkyl or SC 1-12 linear or branched alkyl, and a C6aryl, OC6aryl or SC6aryl group, the alkyl or aryl group being substituted or unsubstituted; or R 1 and R 2 with the nitrogen or phosphorus atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as previously defined, or R 1 , R 2 and R 3with the nitrogen or phosphorus atom together form a 5- to 12-membered, single- or multi-ring, partially unsaturated heteroaryl or heterocycloalkyl group, the heteroaryl or heterocycloalkyl group being substituted or unsubstituted; L is, independently at each occurrence, a straight or branched C2-8alkylene; X is a halogen atom; Y is O or S; m is a number greater than or equal to 1, or in the range 1 to 6; and n is an integer greater than or equal to 1, or in the range 1 to 11. In some examples, when the compound is of Formula I, X is Br, A- is bis(trifluoromethanesulfonyl)imide (TFSI-), R +is a 3-methyl-1-imidazolium group, then n is other than 5. The compound of Formula I or II is preferably an ionic liquid at room temperature or near room temperature. For example, the compound of Formula I or II preferably has a melting point of 60°C or less, or 40°C or less, preferably 25°C or less. The delocalized anion A- is preferably selected from anions comprising a phosphate, an imide, a sulfonylimide, a sulfonate, a sulfate, a borate, a nitrate, an arsenate, or a triazolate.For example, the delocalized anion may be selected from the group consisting of hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), 2-trifluoromethyl-4,5-dicyanoimidazolate (TDI-), 4,5-dicyano-1,2,3-triazolate (DCTA-), bis(pentafluoroethylsulfonyl)imide (BETI-), difluorophosphate (DFP-), tetrafluoroborate (BF4-), bis(oxalato)borate (BOB-), nitrate (NO3-), perchlorate (ClO4-), hexafluoroarsenate (AsF6-), trifluoromethanesulfonate (CF3SO3- or -OTf), fluoroalkylphosphate ([PF3(CF2CF3)3]- or FAP-), tetrakis(trifluoroacetoxy)borate ([B(OCOCF3)4]- or TFAB-), bis(1,2-benzenediolato(2-)- O,O')borate ([B(C6O2)2]- or BBB-), difluoro(oxalato)borate (BF2(C2O4)- or FOB-), and an anion of formula BF2O4R. x (R x= C2-4alkyl). For example, the delocalized anion is selected from the group consisting of hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), tetrafluoroborate (BF4-), and trifluoromethanesulfonate (CF3SO3- or -OTf), preferably bis(trifluoromethanesulfonyl)imide (TFSI-). According to one example, R + is a group of formula -N + (R 1 R 2 R 3 ), in which R 1 , R 2 and R 3 are independently selected from linear or branched, substituted or unsubstituted C1-12alkyl groups. According to another example, R + is a group of formula -N + (R 1 R 2 R 3 ), in which R 1 , R 2 and R 3are independently selected from linear or branched C1-12alkyl groups, or at least one of R 1 , R 2 or R 3 is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group. In another example, R + is a group of formula -N + (R 1 R 2 R 3 ), in which R 1 and R 2 with the nitrogen atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as previously defined, preferably R3 is a C group 1-12 alkyl or a C group 1-4 alkyl. According to an example of interest, R 3 is a C group 1-4 unsubstituted alkyl (such as methyl, ethyl, n- or i-propyl, n-, i-, s-, and t-butyl), and preferably R 3 is a methyl group. In another example, R + is a group of formula -N + (R 1 R 2R 3 ), in which R 1 , R 2 and R 3 with the nitrogen atom together form a heteroaromatic or partially unsaturated heterocycle with one or more rings and having from 5 to 12 members. According to another example, R + is chosen from: R 3 is as defined above; R 4 is a linear or branched, substituted or unsubstituted C1-12alkyl, C1-12alkenyl or C1-12alkynyl group; and R 5 is a hydrogen or halogen atom or a linear or branched, substituted or unsubstituted C1-12alkyl, C1-12alkenyl or C1-12alkynyl group; the heterocycle being optionally substituted. According to a preferred example, R + is of formula: in which R 3 is as defined previously. The group R 3 when present in the above heterocycles, may be a C group 1-4unsubstituted alkyl, for example selected from a methyl group, an ethyl group, an n- or i-propyl group, and an n-, i-, s- or t-butyl group. When the group R 4 is present, this can be a C group 1-4 alkyl. R 5 , when present, can also be a hydrogen atom or a C group 1-4 alkyl. According to another example, R + is a group of formula -P + (R 1 R 2 R 3 ), in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched, substituted or unsubstituted alkyls. According to another example, R + is a group of formula -P + (R 1 R 2 R 3 ), in which R 1 , R 2 and R 3 are independently selected from linear or branched C1-12alkyl groups, or at least one of R 1, R 2 you R 3is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group. In some embodiments, the compound is of Formula I. In some examples, n may be a number in the range of 2 to 10, or 3 to 8, or 4 to 6, inclusive. In other embodiments, the compound is of Formula II. In some examples, L is a straight or branched C2-4alkylene or a straight or branched C2-3alkylene. In a preferred embodiment, the variable Y may be an oxygen atom. Alternatively, the variable Y may be a sulfur atom. In some examples, m is a number from 1 to 4, or 1 to 3. In some examples, X is a chlorine, bromine or iodine atom, or X is a chlorine or bromine atom, or X is a bromine atom.Examples of compounds as described herein include, but are not limited to, the delocalized anion A- of the 1-(6-bromohexyl)-1-methylpyrrolidinium, 1-(6-chlorohexyl)-1-methylpyrrolidinium, or 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium cation, e.g., 1-(6-bromohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 1), 1-(6-chlorohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 2), or 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 3). The present technology also includes compositions comprising at least one compound as described herein. Preferably, the composition further comprises an ionic solid such as an ionic bifunctional molecule. According to certain embodiments, the ionic bifunctional molecule is of Formula III or IV:. in which A-, R +, L, Y, m and n are independently at each occurrence as defined above for the compound, separately including each of the examples, embodiments and alternatives. It is noted that the variables A-, R +, L, Y, m and n of the compound can be independently different or identical to these variables in the ionic bifunctional molecule for the same composition. In some examples, the ionic bifunctional molecule is selected from 1,1'-(1,6-hexamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide, 1,1'-(1,12-dodecamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide, 1,1'-(2,2′-(ethylenedioxy)diethane) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide, 1,1'-(thiol bis(1,2-ethane)) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide and 3,3'-(1,6-hexamethylene) bis(1,2-dimethylimidazolium) bis(trifluoromethanesulfonyl)imide. In an example of interest, the ionic bifunctional molecule is 1,1'-(1,6-hexamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide. According to certain preferred embodiments, wherein the weight ratio of "compound:ionic bifunctional molecule" is from about 2:98 to about 50:50, or from about 5:95 to about 35:65, or from about 10:90 to about 30:70. For example, the composition is solid at room temperature (e.g., at about 25°C ± 5°C). The present technology also refers to a solid electrolyte comprising an ionic organic compound as defined herein, or a composition as defined above, preferably a composition as defined herein. According to certain examples, the solid electrolyte further comprises inorganic particles. For example, the inorganic particles may be selected from any known inorganic solid electrolyte material particles and may be selected according to their compatibility with the various elements of a possible electrochemical cell.For example, the inorganic particles may comprise a material selected from glasses, glass-ceramics, ceramics, nanoceramics, and a combination of two or more thereof. In one example, the inorganic particles may comprise a fluoride, phosphide, sulfide, oxysulfide, or oxide-based ceramic, glass, or glass-ceramic. In another example, the inorganic particles may comprise a LISICON, thio-LISICON, argyrodite, garnet, NASICON, perovskite, oxide, sulfide, oxysulfide, phosphide, or fluoride compound in crystalline and / or amorphous form, or a combination of two or more thereof. According to another example, the inorganic particles comprise a compound selected from inorganic compounds of formulae: - MLZO (e.g., M7La3Zr2O12, M(7-a)La3Zr2AlbO12, M(7-a)La3Zr2GabO12, M(7-a)La3Zr(2-b)TabO12, and M(7-a)La3Zr(2-b)NbbO12); - MLTaO (e.g., M7La3Ta2O12, M5La3Ta2O12, and M6La3Ta1.5Y0.5O12); - MLSnO (for example, M7La3Sn2O12); - MAGP (for example, M1+aAlaGe2-a(PO4)3); - MATP (for example, M1+aAlaTi2-a(PO4)3,); - MLTiO (par exemple, M. 3a There (2 / 3-a) TiO3); - MZP (for example, M a Zr b (PO4) c ); - MCZP (for example, M a Ca b Zr c (PO4) d ); - MGPS (par exemple, M a Ge b P c S d tel que M 10 GeP2S 12 ); - MGPSO (for example, M a Ge b P c S d OR e ); - MSiPS (for example, M a Yes b P c S d tel que M 10 SiP2S 12 ); - MSiPSO (for example, M a Yes b P c S d OR e ); - MSnPS (par exemple, M a Sn b P c S d tel que M 10 SnP2S 12 ); - MSnPSO (for example, M a Sn b P c S d OR e); - MPS (e.g., M a P b S c such as M7P3S 11 ); - MPSO (e.g., M a P b S c O d ); - MZPS (e.g., M a Zn b P c S d ); - MZPSO (e.g., MaZnbPcSdOe); - xM2S-yP2S5; - xM2S-yP2S5-zMX; - xM2S-yP2S5-zP2O5; - xM2S-yP2S5-zP2O5-wMX; - xM2S-yM2O-zP2S5; - xM2S-yM2O-zP2S5-wMX; - xM2S-yM2O-zP2S5-wP2O5; - xM2S-yM2O-zP2S5-wP2O5-vMX; - xM2S-ySiS2; - MPSX (e.g., MaPbScXd such as M7P3S11X, M7P2S8X, and M6PS5X); - MPSOX (e.g., MaPbScOdXe); - MGPSX (e.g., MaGebPcSdXe); - MGPSOX (e.g., MaGebPcSdOeXf); - MSiPSX (e.g., MaSibPcSdXe); - MSiPSOX (e.g., MaSibPcSdOeXf); - MSnPSX (e.g., MaSnbPcSdXe); - MSnPSOX (e.g., MaSnbPcSdOeXf); - MZPSX (e.g., MaZnbPcSdXe); - MZPSOX (e.g., M a Zn b P c S d O e X f ); - M3OX; - M2HOX; - M3PO4; - M3PS4; and - Ma P.O. b N c(where a = 2b + 3c - 5); wherein, M is an alkali metal ion, an alkaline earth metal ion or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality; X is selected from F, Cl, Br, I or a combination of two or more thereof and may be the same as or different from X present in the compound of Formula I or II; a, b, c, d, e and f are non-zero numbers and are, independently in each formula, selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are, independently in each formula, selected to obtain a stable compound. For example, M may be selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba or a combination of two or more thereof. According to a variant of interest, M is Li.According to one embodiment of interest, the inorganic particles comprise an inorganic compound of formula MATP as defined herein. According to another embodiment of interest, the inorganic particles comprise a sulfide or an oxysulfide. According to one example, the inorganic particles comprise an inorganic compound of formula LiaPbScXd wherein X is Cl, Br, I or a combination of at least two thereof, and a, b, c and d are such that (a + 5b) = (2c + d). For example, the inorganic particles may comprise an inorganic compound of formula Li6PS5Cl. The inorganic compound may be of argyrodite form. According to another example, the inorganic particles comprise a compound selected from inorganic compounds of formula LiaPbScOdXe wherein X is Cl, Br, I or a combination of at least two thereof and a, b, c, d and e are such that (a + 5b) = (2c + 2d + e).In some cases, a is selected from the range of 5 to 6, b is 1, c is selected from the range of 3.5 to 4.8, and e is selected from the range of 1 to 2 (e.g., Li5.4PS4.1O0.3X1.6 or Li5.4PS4.1O0.3ClBr0.5I0.1). The inorganic particles may be present in the solid electrolyte at a concentration in the range of about 20 wt.% to about 95 wt.%, inclusive. For example, the inorganic particles may be present in the solid electrolyte at a concentration in the range of about 40 wt.% to about 95 wt.%, or about 60 wt.% to about 95 wt.%, inclusive. The concentration of the compound in the electrolyte may be in the range of about 0.2% to about 5% by weight, or about 0.3% to about 4% by weight, or about 0.4% to about 3% by weight, inclusive.When the composition as defined above is present in the electrolyte, it may be present at a concentration of about 1% to about 15% by weight, or about 2% to about 10% by weight, or about 4% to about 8% by weight, in the total mass of solid electrolyte. The solid electrolyte as defined herein may further include a polymer. For example, the polymer may be chosen for its compatibility with the various elements of an electrochemical cell. Any known compatible polymer is contemplated. The polymer may be chosen from linear or branched polymers.Non-limiting examples of polymers include polyethers (e.g., a polyether based on polyethylene oxide (PEO), polypropylene oxide (POP), or a combination of both (such as an EO / PO copolymer)), polythioethers, polyesters, polythioesters, polydimethylsiloxanes, polyalkylene carbonates, polyalkylene thiocarbonates, polyalkylene sulfones, polyalkylene sulfonamides, polyimides, polyamides, polyphosphazenes, polyurethanes, polyvinyl alcohols, polyacrylonitriles, polyethacrylates and polymethacrylates, and copolymers thereof, optionally comprising crosslinked units derived from crosslinkable functional groups (such as acrylate, methacrylate, vinyl, glycidyl, mercapto, etc.) or their cross-linked equivalents.In one example, the polymer, if present in the electrolyte, may be the reaction product between at least one monomer comprising at least one polymerizable or crosslinkable functional group and a compound comprising at least one SH functional group. In another example, the polymer may be present in the solid electrolyte at a concentration in the range of about 0.1 wt% to about 20 wt%, inclusive. For example, the polymer may be present in the solid electrolyte at a concentration in the range of about 1 wt% to about 15 wt%, or from about 2 wt% to about 13 wt%, inclusive.For example, the ionic organic compound or composition as defined herein acts as binders between the inorganic particles in the present solid electrolyte, the binder thus also being able to further comprise the polymer as defined herein. The solid electrolyte as defined herein may also optionally include an additive. In one example, the additive, if present in the electrolyte, may be a fluorinated compound comprising an amide function. The fluorinated compound may be of formula R. 6 X 6 C(O)N(H)X 7 R 7 , where R 6 and R 7 are independently alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl groups, X 6 is O, NH or absent, and X 7 is absent or is a C(O), S(O)2, or Si(R) group 8 R 9 ), where R 8 and R 9 are alkyl groups, and where at least one of R 6 , R 7 , R 8 and R 9is a group substituted by one or more fluorine atom(s). For example, R 6 is a perfluorinated group and X 6is absent. The present technology also relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein at least one of the negative electrode, the positive electrode and the electrolyte comprises an ionic organic compound or composition as defined herein, preferably the electrolyte being as defined above. The positive electrode comprises a positive electrode material optionally on a current collector, the positive electrode material comprising a positive electrode electrochemically active material. Non-limiting examples of positive electrode electrochemically active materials include metal phosphates, lithiated metal phosphates, metal oxides, and lithiated metal oxides. For example, the metal of the electrochemically active material may be selected from titanium (Ti), iron (Fe), magnesium (Mg), manganese (Mn), vanadium (V), nickel (Ni),cobalt (Co), aluminum (Al), chromium (Cr), copper (Cu), antimony (Sb) and a combination of at least two of these, when compatible. According to a variant of interest, the metal of the electrochemically active material can be chosen from titanium (Ti), iron (Fe), magnesium (Mg), manganese (Mn), vanadium (V), nickel (Ni), cobalt (Co), aluminum (Al) and a combination of at least two of these, when compatible. Non-limiting examples of electrochemically active positive electrode materials generally include metal phosphates and lithium metal phosphates (e.g., LiM'PO4 and M'PO4, where M' is selected from Fe, Ni, Mn, Co and a combination of at least two thereof), vanadium oxides and lithium vanadium oxides (e.g., LiV3O8, V2O5F, LiV2O5 and other similar vanadium oxides and lithium vanadium oxides), and lithium metal oxides of the formulas LiMn2O4,LiM''O2 (where M'' is selected from Mn, Co, Ni, and a combination of at least two thereof) (such as NMC, LiMnxCoyNizO2 with x+y+z = 1), Li(NiM''')O2 (where M''' is selected from Mn, Co, Al, Fe, Cr, Ti, Zr, another similar metal and a combination of at least two thereof), elemental sulfur, selenium or iodine, iron(III) fluoride, copper(II) fluoride, lithium iodide, carbon-based active materials such as graphite, organic cathode active materials, or a combination of at least two of these electrochemically active materials, when compatible with each other. The positive electrode material as defined herein may further include an electronically conductive material, a binder, a salt, the present ionic organic compound, an ionic bifunctional molecule (e.g., an ionic bifunctional molecule as defined above),and / or inorganic particles. The negative electrode comprises a negative electrode material comprising a negative electrode electrochemically active material which is optionally on a current collector. In one example, the negative electrode electrochemically active material may comprise a metal film comprising an alkali or alkaline earth metal or an alloy comprising an alkali or alkaline earth metal. For example, the alkali metal may be selected from lithium and sodium. In another example, the negative electrode electrochemically active material may include an intermetallic compound (e.g., SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2, and CoSn2), a metal oxide, a metal nitride, a metal phosphide, a metal phosphate (e.g., LiTi2(PO4)3), a metal halide (e.g., a metal fluoride), a metal sulfide, a metal oxysulfide, a carbon (e.g., graphite, graphene,reduced graphene oxide, hard carbon, soft carbon, exfoliated graphite and amorphous carbon), silicon (Si), silicon-carbon composite (Si-C), silicon oxide (SiO, x ), a silicon oxide-carbon composite (SiO x -C), tin (Sn), a tin-carbon composite (Sn-C), a tin oxide (SnO x ), a tin oxide-carbon composite (SnO x -C), and a combination of at least two of these, when compatible. For example, the metal oxide may be chosen from compounds of formulas M'''' b O c(where M'''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof; and b and c are numbers such that the c:b ratio is in the range from 2 to 3) (e.g., MoO3, MoO2, MoS2, V2O5, and TiNb2O7), spinel oxides (e.g., NiCo2O4, ZnCo2O4, MnCo2O4, CuCo2O4, and CoFe2O4) and LiM'''''O (where M''''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof) (e.g., a lithium titanate (such as Li4Ti5O12) or a lithium molybdenum oxide (such as Li2Mo4O13)). In another example, the negative electrode material may further comprise an electronically conductive material, a binder, a salt, the present ionic organic compound, an ionic bifunctional molecule (e.g., an ionic bifunctional molecule as defined above), and / or inorganic particles. The present technology also relates to a method for preparing a solid electrolyte as described herein.This method may comprise mixing the compound or composition as defined herein with inorganic particles and optionally a polymer and / or a solvent. The resulting mixture is then applied to a surface and dried if the solvent is present. The surface may be a temporary inert surface which will eventually be removed, for example during the assembly of an electrochemical cell comprising the solid electrolyte. In this case, the solid electrolyte forms a film, which is then combined with at least one positive electrode and at least one negative electrode. Alternatively, the surface to which the mixture is applied is the surface of one electrode, this being the positive electrode or the negative electrode, the method being followed by the application of the other electrode to the free surface of the solid electrolyte.Another preparation method could include applying to a surface the powdery mixture comprising the inorganic particles followed by a step of applying a mixture comprising the compound or composition optionally in a solvent followed by evaporation of the latter. The present technology also relates to an electrochemical accumulator comprising at least one electrochemical cell as defined herein. For example, the electrochemical accumulator is selected from the group consisting of a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a potassium battery, a potassium-ion battery, a magnesium battery, and a magnesium-ion battery. According to a variant of interest, the electrochemical accumulator is a lithium battery or a lithium-ion battery.The presence of an ionic organic compound as defined herein in a solid electrolyte, for example, in an inorganic solid electrolyte or a polymer-ceramic hybrid solid electrolyte can significantly improve certain of its physical and / or electrochemical properties. For example, the present compound demonstrates a positive interaction with ionic solids such as ionic bifunctional molecules as described above. According to another example, the presence of the present compound, particularly in combination with an ionic bifunctional molecule, can substantially improve the ionic conductivity and / or electrochemical stability of the solid electrolyte film, as well as its mechanical strength. EXAMPLES The following examples are for illustrative purposes and should not be interpreted as further limiting the scope of the invention as contemplated. These examples will be better understood by referring to the attached Figures.Example 1 – Preparation of ionic organic compound (i) Preparation of 1-(6-bromohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 1). In a 100 mL flask closed with a septum, 1,6-dibromohexane (20.8 g, 85.6 mmol) is introduced and cooled to 0°C under N2. A solution of 1-methylpyrrolidine (3.6 g, 42.8 mmol) in 20 mL of tetrahydrofuran is added dropwise into the flask with stirring. The solution is then stirred at room temperature for 12 h. The precipitate is then separated by filtration and washed three times with tetrahydrofuran. The product, 1-(6-bromohexyl)-1-methylpyrrolidinium bromide, obtained is dried under vacuum at 50°C for 24 h. Anion exchange with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) is carried out in deionized water at room temperature for 3 h. The precipitate is removed by filtration, the organic phase is extracted with dichloromethane, then washed with deionized water. Once the washing is complete, the organic solution is then dried over sodium sulfate.The solvent is then evaporated and the final product is dried under vacuum at 60°C for 48 hours. Compound 1 (1-(6-bromohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide) is then obtained as an oil. (ii) Preparation of 1-(6-chlorohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 2). In a 100 mL flask with 1,6-dichlorohexane (13.3 g, 85.6 mmol) is introduced and cooled to 70°C under N2. A solution of 1-methylpyrrolidine (3.6 g, 42.8 mmol) in 20 mL of acetonitrile is added dropwise into the flask with stirring. The solution is then stirred at 70°C for 12 h. The solvent is evaporated. The solid is introduced into a mixture of acetone / methanol (20 mL with a volume ratio of 10 / 1.05). The precipitate is then removed by filtration, and the solvent is evaporated. This process is repeated twice. The product, 1-(6-chlorohexyl)-1-methylpyrrolidinium chloride, obtained is dried under vacuum at 50°C for 24 h. Anion exchange with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) is carried out in deionized water at room temperature for 3 hours. The organic phase is extracted with dichloromethane and then washed with deionized water.Once the washing is complete, the organic solution is then dried over sodium sulfate. The solvent is then evaporated and the final product is dried under vacuum at 60°C for 48 hours. Compound 2 (1-(6-chlorohexyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide) is then obtained in the form of a yellow liquid. (iii) Preparation of 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide (Compound 3). In a 100 mL flask with bis(2-chloroethoxy)ethane (20 g, 107 mmol) is introduced and cooled to 70°C under N2. A solution of 1-methylpyrrolidine (3.6 g, 42.8 mmol) in 20 mL of acetonitrile is added dropwise into the flask with stirring. The solution is then stirred at 70°C for 12 h. The solvent is evaporated. The viscous solid is washed three times with diethyl ether. The product, 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium chloride, obtained is dried under vacuum at 50°C for 24 h. Anion exchange with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) is carried out in deionized water at room temperature for 3 h. The organic phase is extracted with dichloromethane and then washed with deionized water. Once the washing is complete, the organic solution is then dried over sodium sulfate. The solvent is then evaporated and the final product is dried under vacuum at 60°C for 48 hours.Compound 3 (1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide) is then obtained in yellow liquid form. Example 2 – Characterization by nuclear magnetic resonance (NMR) Compounds 1, 2 and 3 prepared in Example 1 were characterized by proton nuclear magnetic resonance (. 1 H NMR). The spectra 1 H NMR of the compounds prepared in Example 1 were obtained in DMSO-d6 (deuterated dimethyl sulfoxide) as solvent. The spectra obtained are shown in Figures 1(a) to 1(c) and include the assignment of each of the peaks. 1H NMR in DMSO-d6(δ ppm): Compound 1.1,33 -CH2-C2H4-N; 1.45 -CH2-C2H4-Br; 1.72 -CH2-CH2-CH2-N; 1.84 -CH2-CH2- CH2-Br; 2.09 -CH2-C2H4-CH2-N cyclic; 2.98 -CH3; 3.25-3.34 CH2-CH2-N; 3.34-3.51 - CH2-N-CH2- cyclic; 3.55 -CH2-Br. (see Figure 1(a)) Compound 2.1,34 -CH2-C2H4-N; 1.45 -CH2-C2H4-Cl; 1.62-1.82 -CH2-CH2-CH2-N and -CH2- CH2-CH2-Cl; 2.09 -CH2-C2H4-CH2-N cyclic; 2.98 -CH3; 3.24-3.36 CH2-CH2-N; 3.36-3.55 -CH2-N-CH2- cyclic; 3.65 -CH2-Cl. (see Figure 1(b)) Compound 3.2.09 -CH2-C2H4-CH2-N cyclic; 3.05 -CH3; 3.47-3.58 -CH2-N-CH2- cyclic; 3.60 -O-CH2-CH2-N; 3.61 -O-CH2-CH2-O-; 3.66-3.78 -CH2-O-CH2-CH2-O-CH2-; 3.82-3.90 -CH2-Cl. (see Figure 1(c)) Example 3 – Thermal and Thermogravimetric Analysis Figures 2(a) to 2(c) present the results of Differential Scanning Calorimetry (DSC) analysis obtained for Compounds 1, 2 and 3 prepared in Example 1.The DSC analysis was carried out in a temperature range from about -80°C to about 150°C at a heating rate (or speed) of 10°C / min. As shown in Figure 4, Compound 1 has a crystallization temperature of -51°C and a melting temperature of -29°C. For Compound 2 and Compound 3, there is no crystallization between about -80°C and about 150°C. Figures 3(a) to 3(c) present the thermogravimetric analysis (TGA) results obtained for Compounds 1, 2 and 3 prepared in Example 1. The thermogravimetric analysis was carried out in a temperature range from about 30°C to about 600°C. As shown in Figure 3(a), Compound 1 has a decomposition point around 269 °C. Compound 2 and Compound 3 have a decomposition point around 296 °C (see Figures 3(b) and 3(c) respectively).Example 4 – Preparation and Characterization of Organic Compound Compositions with Ionic Solid Different compositions were prepared, these comprising Compound 1 or 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide (Compound IL) in combination with the ionic solid 1,1'-hexamethylene bis(1-methylpyrrolidinium) bis(trifluoromethylsulfonyl)imide (Compound SI) in the proportions described in Table 1. Table 1. Ionic Liquid and Ionic Solid Compositions C. omposition Composé 1 Compound IL Compound SI ts mass ratios. DSC analysis was carried out over a temperature range from about -80 °C to about 148 °C at a heating rate of 10 °C / min. Data extracted from the DSC measurements are shown in Table 2 below. Table 2. Data extracted from DSC of Compositions 1, 2 and A1-A3 Composition Crystallization Transition Point (°C) sion (°C) vitreous (°C) the melting point of Composition 1 with the same weight ratio is 57°C, which is 10°C higher. This difference indicates that the intermolecular interaction between Compound 1 and the ionic solid (Compound SI) is stronger than that of the mixture of Compound IL at the 20 / 80 ratio. In addition, a weak molecular interaction between Compound IL and Compound SI may lead to phase separation, thus disturbing the electrochemical properties of said mixture, as shown in Example 5. Example 5 – Preparation and Characterization of Composite Solid Electrolyte Films The crosslinkable polymer used in the following example is a multi-branched polyether comprising crosslinkable units, as described in U.S. Patent No. 7,897,674 (hereinafter referred to as “polymer US’674”).a) Preparation of ceramic-co-binder composite solid electrolyte films Composite solid electrolyte films comprising a sulfide-based ceramic, the ionic solid salt Compound SI as defined above, and Compound 1 were prepared with compositional variations. Composite solid electrolyte films comprising a sulfide-based ceramic and the ionic solid salt Compound SI with or without a halogen-free ionic liquid (Compound IL) were also prepared for comparison purposes. The halogen-free ionic liquid is Compound IL as defined above, thus having a similar structure to Compound 1 but with a four-carbon chain and without the halogen at the end of the chain.Other composite solid electrolyte films (E10 and E11) comprising a sulfide-based ceramic, the ionic solid salt SI, and the halogenated ionic liquid (Compounds 2 or 3) were prepared and compared to film E2 (equivalent with Compound 1) or composite solid electrolyte films comprising a sulfide-based ceramic and the ionic solid salt (SI) with or without halogen-free ionic liquid. All manipulations were carried out in a glove box under an argon atmosphere (0.1 ppm H2O; 0.1 ppm O2). Two sizes (about 3 μm and less than 1 μm) of sulfide-based ceramic-type inorganic solid electrolyte particles (Li6PS5Cl) were mixed in a 90:10 mass ratio using a vortex mixer.The binder is formed from a 40 / 60 mass mixture of (a) US'674 polymer containing 4.0 wt% TBT (4,4'-thiobisbenzenethiol) and (b) ionic solid Compound SI with or without the ionic liquid, halogenated (Compound 1, 2 or 3) or not (Compound IL), dissolved in dichloromethane. The weight ratio between sulfide-based ceramic and binder was 90 / 10 mass. The amount of dichloromethane was adjusted to obtain a mixture with an appropriate viscosity. The resulting mixture was coated onto a previously degreased aluminum foil. The film was dried in a glove box. The composition of ceramic-ionic co-binder composite solid electrolyte films is shown in Table 3. Table 3. Composition of ceramic-ionic co-binder composite solid electrolyte films Binder (b) Electrolyte SI compound Compound IL compound. b) Ionic Conductivity of Ceramic-Ionic Co-Binder Composite Solid Electrolyte Films Pellets of 10 mm diameter were taken from the ceramic-ionic co-binder composite solid electrolyte films prepared in Example 6(a). The pellets were placed in a 10 mm diameter mold and compressed under a pressure of 2.8 tons using a press. The pellets were then placed in a conductivity cell at a pressure of 5 MPa closed under an inert argon atmosphere. The electrodes are made of stainless steel. The configuration of each cell is shown as follows: Cell X: Electrode / Electrolyte / Electrode Cells 1 to 11 were prepared with the corresponding electrolytes E1 to E11 as described in (a) above. Ionic conductivity measurements of the cells assembled in this example were performed with a VMP-300 multichannel potentiostat (Bio-Logic MC). The measurements were carried out in a frequency range from 7 MHz to 200 mHz under an amplitude of 50 mV in a temperature interval from -20°C to 70°C (increasing every 10°C) and from 70°C to 20°C decreasing temperature (every 10°C). The impedance measurements were obtained after a stabilization of approximately one hour. Two impedance measurements were recorded at each temperature with 15 minutes between each measurement. Figure 5 presents the results of ionic conductivity measured as a function of temperature for Cells 1 (■), 2 (●), 3 (▲), 4 (▼), 5 (◄), 6 (►) and 7 ( ^). The ionic conductivity after passing to 70°C and returning to 20°C is higher due to the liquefaction and recrystallization of the ionic solid (Compound SI).It is possible to observe in Figure 5 that the ionic conductivity before and after passing 70°C increases with the increase in the addition of halogenated ionic liquid, demonstrating an interaction between the co-binder, formed of ionic solid and halogenated ionic liquid, and the sulfide ceramic particles. It should be noted that a stabilization of the ionic conductivity is observed from approximately 20% of halogenated ionic liquid vs. the ionic solid. In addition, only a straight line of activation energy appears in temperature rise and temperature fall, confirming the interaction of the halogenated ionic liquid which is liquid with the other solid constituents such as the ionic solid and the sulfide ceramic solid electrolyte. The halogenated ionic liquid therefore mixes with the other constituents without phase separation.Figure 6 presents the results of ionic conductivity measured as a function of temperature for Cells 1 (■), 3 (▲), 6 (►), 7 ( ^), 8 (∆) and 9 (♦) in order to compare the effect of adding halogenated ionic liquid to that of non-halogenated ionic liquid. It can be observed in Figure 6 that the ionic conductivity with the addition of halogenated or non-halogenated ionic liquid for the proportion around 10% is identical. For the 20% composition, a clear decrease in ionic conductivity is observed when using non-halogenated ionic liquid versus halogenated ionic liquid which at 20% allows reaching the maximum tested ionic conductivity. In addition, two activation energy slopes can be observed with a temperature rise with an intersection around 45°C. This temperature corresponds to the temperature observed in DSC in Figure 4 and Table 2 of Example 4.Thus, a phase separation occurs between the non-halogenated ionic liquid and the ionic solid leading to a differentiation of activation energy. This is not observed with the use of halogenated ionic liquid such as Compound 1, confirming its greater interaction and interest as a co-binder with the ionic solid for application with a ceramic in a solid electrolyte. In addition, a better mechanical resistance to cutting could be observed for the electrolyte films with the addition of halogenated ionic liquid. Figure 7 presents the results of ionic conductivity measured as a function of temperature for Cells 1 (■), 2 (●), 10 ( ^) and 11 (▲) in order to compare the effect of the addition of the halogenated ionic liquid of Compounds 1, 2 and 3, with that of the ionic solid only. Several modifications could be made to any of the embodiments described above without departing from the scope of the present invention as contemplated.The references, patents or scientific literature documents referred to in this application are incorporated herein by reference in their entirety and for all purposes.

Claims

CLAIMS 1. Compound of Formula I or II: in which, A- is a delocalized anion; R + is chosen from the groups -N + (R 1 R 2 R 3 ) and -P + (R 1 R 2 R 3 ); R 1 , R 2 and R 3 , when adjacent to N, are independently selected from a hydrogen atom and a linear or branched C1-12alkyl or C6aryl group, the alkyl or aryl group being substituted or unsubstituted, where when one of R 1 , R 2 and R 3 is a hydrogen atom then the other two are other than a hydrogen atom; R 1 , R 2 and R 3 , when adjacent to P, are independently selected from a linear or branched C1-12alkyl, OC1-12alkyl or SC1-12alkyl group, and a C6aryl, OC6aryl or SC6aryl group, the alkyl or aryl group being substituted or unsubstituted; or R 1and R 2 with the nitrogen or phosphorus atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as previously defined, or R 1 , R 2 and R 3 with the nitrogen or phosphorus atom together form a partially unsaturated heteroaryl or heterocycloalkyl group with one or more rings and having from 5 to 12 members, the heteroaryl or heterocycloalkyl group being substituted or unsubstituted; L is, independently at each occurrence, a C 2-8 linear or branched alkylene; X is a halogen atom; Y is O or S; m is a number greater than or equal to 1, or in the range 1 to 6; and n is an integer greater than or equal to 1, or in the range 1 to 11; preferably when the compound is of Formula I, X is Br, A- is bis(trifluoromethanesulfonyl)imide (TFSI-), R +is a 3-methyl-1-imidazolium group, then n is different from 5.

2. Compound according to claim 1, in which A- is chosen from anions comprising a phosphate, an imide, a sulfonylimide, a sulfonate, a sulfate, a borate, a nitrate, an arsenate, or a triazolate. 3.A compound according to claim 1 or 2, wherein A- is selected from hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), 2-trifluoromethyl-4,5-dicyanoimidazolate (TDI-), 4,5-dicyano-1,2,3-triazolate (DCTA-), bis(pentafluoroethylsulfonyl)imide (BETI-), difluorophosphate (DFP-), tetrafluoroborate (BF4-), bis(oxalato)borate (BOB-), nitrate (NO3-), perchlorate (ClO4-), hexafluoroarsenate (AsF6-), trifluoromethanesulfonate (CF3SO3- or -OTf), fluoroalkylphosphate ([PF3(CF2CF3)3]- or FAP-), tetrakis(trifluoroacetoxy)borate ([B(OCOCF3)4]- or TFAB-), bis(1,2-benzenediolato(2-)-O,O')borate ([B(C6O2)2]- or BBB-), difluoro(oxalato)borate (BF2(C2O4)- or FOB-), and an anion of formula BF2O4R. x (R x= C2-4alkyl).

4. A compound according to claim 3, wherein the delocalized anion is selected from hexafluorophosphate (PF6-), bis(trifluoromethanesulfonyl)imide (TFSI-), bis(fluorosulfonyl)imide (FSI-), (flurosulfonyl)(trifluoromethanesulfonyl)imide (FTFSI-), tetrafluoroborate (BF4-), and trifluoromethanesulfonate (CF3SO3- or - OTf).

5. A compound according to claim 4, wherein the delocalized anion is bis(trifluoromethanesulfonyl)imide (TFSI-).

6. A compound according to any one of claims 1 to 5, wherein R + is a -N grouping + (R 1 R 2 R 3 ).

7. Compound according to claim 6, in which R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched alkyls, substituted or unsubstituted.

8. A compound according to claim 6, wherein R 1 , R 2 and R 3are independently chosen from the groups C 1-12 linear or branched alkyls, where at least one of R 1 , R 2 , and R 3 is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group.

9. A compound according to claim 6, wherein R 1 and R 2 with the nitrogen atom together form a heterocycle with one or more rings and having from 3 to 12 members and R 3 is as defined in claim 1, preferably R 3 is a C 1- 12 alkyl, or a C 1-4 alkyl.

10. A compound according to claim 6, wherein R 1 , R 2 and R 3 with the nitrogen atom together form a heteroaromatic or partially unsaturated heterocycle with one or more rings and having from 5 to 12 members.

11. A compound according to claim 6, in which R + is chosen from the heterocycles: R 4is a linear or branched, substituted or unsubstituted C1-12alkyl, C1-12alkenyl or C1-12alkynyl group; and R 5 is a hydrogen or halogen atom or a C group 1-12 alkyl, C 1- 12-alkenyl or C1-12-alkynyl, linear or branched, substituted or unsubstituted; the heterocycle being optionally substituted.

12. A compound according to claim 11, wherein R + is of formula: in which R 3 is such that 1.

13. A compound according to any one of claims 1 to 9, 11 or 12, wherein R 3 is a C group 1-4 unsubstituted alkyl.

14. A compound according to claim 13, wherein R 3 is selected from a methyl group, an ethyl group, an n- or i-propyl group, and an n-, i-, s- or t-butyl group.

15. A compound according to claim 11, in which R 4 is a C group 1-4alkyl.

16. A compound according to claim 11 or 15, wherein R 5 is a hydrogen atom or a C group 1-4 alkyl.

17. A compound according to any one of claims 1 to 5, wherein R + is a -P grouping + (R 1 R 2 R 3 ).

18. A compound according to claim 17, wherein R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 19. A compound according to claim 17, wherein R 1 , R 2 and R 3 are independently chosen from the groups C 1-12 linear or branched alkyls, or at least one of R 1 , R 2 and R 3is substituted by a halogen atom or an alkoxyl, ether, ester or siloxy group.

20. A compound according to any one of claims 1 to 19, the compound being of Formula I.

21. A compound according to claim 20, wherein n is a number in the range 2 to 10, or 3 to 8, or 4 to 6.

22. A compound according to any one of claims 1 to 19, the compound being of Formula II.

23. A compound according to claim 22, wherein L is C 2-4 linear or branched alkylene or a C 2-3linear or branched alkylene.

24. A compound according to claim 22 or 23, wherein Y is O.

25. A compound according to claim 22 or 23, wherein Y is S.

26. A compound according to any one of claims 22 to 25, wherein m is a number from 1 to 4, or from 1 to 3.

27. A compound according to any one of claims 1 to 26, wherein X is Cl, Br or I, preferably Cl or Br, or X is Br.

28. A compound according to any one of claims 1 to 27, which has a melting point of 60°C or less, or 40°C or less, preferably 25°C or less. 29.A compound according to any one of claims 1 to 5, which is selected from the salts A- of 1-(6-bromohexyl)-1-methylpyrrolidinium, 1-(6-chlorohexyl)-1-methylpyrrolidinium, and 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium, preferably bis(trifluoromethanesulfonyl)imide of 1-(6-bromohexyl)-1-methylpyrrolidinium (Compound 1), 1-(6-chlorohexyl)-1-methylpyrrolidinium (Compound 2), or 1-(2-(2-(2-chloroethoxy)ethoxy)ethyl)-1-methylpyrrolidinium (Compound 3).

30. A composition comprising a compound as defined in any one of claims 1 to 29 and an ionic bifunctional molecule.

31. Composition according to claim 30, in which the ionic bifunctional molecule is of Formula III or IV:. in which A-, R +, L, Y, m and n are independently at each occurrence as defined in claims 1 to 26.

32. The composition of claim 31, wherein the ionic bifunctional molecule is 1,1'-(1,6-hexamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide.

33. The composition of claim 31, wherein the ionic bifunctional molecule is 1,1'-(1,12-dodecamethylene) bis(1-methylpyrrolidinium) bis(trifluoromethanesulfonyl)imide.

34. The composition of claim 31, wherein the bifunctional molecule >CB>EI: :GH @: 7>G"HF>;@ICFCANH=6B:GI@;CBL@#>A>9IF: 9: (%(S&")%)[& (ethylenedioxy)diethane) bis(1-methylpyrrolidinium).

35. The composition of claim 31, wherein the ionic bifunctional molecule is 1,1'-(thiol bis(1,2-ethane)) bis(1-methylpyrrolidinum) bis(trifluoromethanesulfonyl)imide. 36.The composition of claim 31, wherein the ionic bifunctional molecule is 3,3'-(1,6-hexamethylene) bis(1,2-dimethylimidazolium) bis(trifluoromethanesulfonyl)imide.

37. The composition of any one of claims 30 to 36, wherein the weight ratio of "compound:ionic bifunctional molecule" is from about 2:98 to about 50:50, or from about 5:95 to about 35:65, or from about 10:90 to about 30:

70.

38. The composition of any one of claims 30 to 37, which is solid at room temperature (e.g., 25°C ± 5°C).

39. Solid electrolyte comprising a compound as defined in any one of claims 1 to 29, or a composition as defined in any one of claims 30 to 38.

40. The solid electrolyte of claim 39, further comprising inorganic particles.

41. The solid electrolyte of claim 40, wherein the inorganic particles comprise a material selected from glasses, glass-ceramics, ceramics, nanoceramics, and a combination of at least two thereof.

42. The solid electrolyte of claim 41, wherein the inorganic particles comprise a fluoride, phosphide, sulfide, oxysulfide, or oxide-based ceramic, glass, or glass-ceramic.

43. The solid electrolyte of claim 41, wherein the inorganic particles comprise a compound of the LISICON, thio-LISICON, argyrodite, garnet, NASICON, perovskite, oxide, sulfide, oxysulfide, phosphide, fluoride type, in crystalline and / or amorphous form, or a combination of at least two of these. 44.The solid electrolyte of claim 41, wherein the inorganic particles comprise a compound selected from inorganic compounds of formulae MLZO (e.g., M7La3Zr2O12, M(7-a)La3Zr2AlbO12, M(7-a)La3Zr2GabO12, M(7-a)La3Zr(2-b)TabO12, and M(7-a)La3Zr(2-b)NbbO12); MLTaO (e.g., M7La3Ta2O12, M5La3Ta2O12, and M6La3Ta1.5Y0.5O12); MLSnO (for example, M7La3Sn2O12); MAGP (for example, M1+aAlaGe2-a(PO4)3); MATP (for example, M1+aAlaTi2-a(PO4)3,); MLTiO (for example, M3aLa(2 / 3-a)TiO3); MZP (for example, MaZrb(PO4)c); MCZP (for example, MaCabZrc(PO4)d); MGPS (for example, MaGebPcSd like M10GeP2S12); MGPSO (for example, MaGebPcSdOe); MSiPS (for example, MaSibPcSd like M10SiP2S12); MSiPSO (for example, MaSibPcSdOe); MSnPS (for example, MaSnbPcSd called M10SnP2S12); MSnPSO (par example, MaSnbPcSdOe); MPS (for example, MaPbSc tel que M7P3S11); MPSO (par example, MaPbScOd); MZPS (for example, MaZnbPcSd); MZPSO (for example, MaZnbPcSdOe); xM2S-yP2S5; xM2S-yP2S5-zMX; xM2S-yP2S5-zP2O5; xM2S-yP2S5-zP2O5-wMX; xM2S-yM2O-zP2S5; xM2S-yM2O-zP2S5-wMX; xM2S-yM2O-zP2S5-wP2O5; xM2S-yM2O-zP2S5-wP2O5-vMX; xM2S-ySiS2; MPSX (see example, M. a P b S c X d tel que M7P3S 11 X, M7P2S8X, et M6PS5X); MPSOX (see example, M a P b S c OR d Xe ); MGPSX (M a Ge b P c S d X e ); MGPSOX (M a Ge b P c S d O e X f ); MSiPSX (M a Si b P c S d X e ); MSiPSOX (M a Si b P c S d O e X f ); MSnPSX (M a Sn b P c S d X e ); MSnPSOX (M a Sn b P c S d O e X f ); MZPSX (M a Zn b P c S d X e ); MZPSOX (M a Zn b P c S d O e X f ); M3OX; M2HOX; M3PO4; M3PS4; et M a PO b N c(where a = 2b + 3c - 5); wherein, M is an alkali metal ion, an alkaline earth metal ion, or a combination of two or more thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality; X is selected from F, Cl, Br, I or a combination of two or more thereof and may be the same as or different from X present in the compound of Formula I or II; a, b, c, d, e and f are non-zero numbers and are, independently in each formula, selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are, independently in each formula, selected to obtain a stable compound.

45. The solid electrolyte of claim 44, wherein M is selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba or a combination of at least two thereof.

46. The solid electrolyte of claim 45, wherein M is Li. 47.A solid electrolyte according to any one of claims 44 to 46, wherein the inorganic particles comprise an inorganic compound of formula MATP.

48. A solid electrolyte according to any one of claims 44 to 46, wherein the inorganic particles comprise a sulfide or an oxysulfide.

49. A solid electrolyte according to any one of claims 44 to 46, wherein the inorganic particles comprise a compound selected from inorganic compounds of formula LiaPbScXd wherein X is Cl, Br, I or a combination of at least two thereof, and a, b, c and d are such that (a + 5b) = (2c + d).

50. A solid electrolyte according to claim 49, wherein the inorganic particles comprise Li6PS5Cl.

51. A solid electrolyte according to any one of claims 44 to 46, wherein the inorganic particles comprise a compound selected from the compounds. inorganic of formula Li a P b S cO d X e wherein X is Cl, Br, I or a combination of at least two thereof and a, b, c, d and e are such that (a + 5b) = (2c + 2d + e).

52. A solid electrolyte according to claim 51, wherein a is selected from the range 5 to 6, b is 1, c is selected from the range 3.5 to 4.8, and e is selected from the range 1 to 2 (e.g. Li 5.4 PS 4.1 O 0.3 X 1.6 or Li 5.4 PS 4.1 O 0.3 ClBr 0.5 I 0.1).

53. The solid electrolyte of any one of claims 40 to 52, wherein the inorganic particles are present at a concentration of about 20% to about 95%, or about 40% to about 95%, or about 60% to about 95%, by weight in the solid electrolyte.

54. The solid electrolyte of any one of claims 39 to 53, wherein the concentration of the compound in the electrolyte is in the range of about 0.2% to about 5% by weight, or about 0.3% to about 4% by weight, or about 0.4% to about 3% by weight.

55. The solid electrolyte of any one of claims 39 to 54, which further comprises a polymer. 56.The solid electrolyte of claim 55, wherein the polymer is a linear or branched polymer selected from polyethers, polythioethers, polyesters, polythioesters, poly(dimethylsiloxanes), poly(alkylene carbonate), poly(alkylene thiocarbonate), poly(alkylene sulfones), poly(alkylene sulfamides), polyimides, polyamides, polyphosphazenes, polyurethanes, poly(vinyl alcohols), polyacrylonitriles, polyethacrylates and polymethacrylates, and copolymers thereof.

57. The solid electrolyte of claim 56, wherein the polyether is poly(ethylene oxide) (PEO), poly(propylene oxide) (POP), or a (EO / PO) copolymer.

58. Solid electrolyte according to claim 56 or 57, wherein the polymer comprises crosslinked units originating from crosslinkable functional groups or their crosslinked equivalents.

59. The solid electrolyte of claim 58, wherein the crosslinkable functional group is selected from acrylate, methacrylate, vinyl, glycidyl, and mercapto functional groups.

60. The solid electrolyte of claim 55, wherein the polymer is the reaction product of at least one monomer comprising at least one polymerizable or crosslinkable function and a compound comprising at least one SH functional group.

61. The solid electrolyte of any one of claims 55 to 60, wherein the polymer is present at a concentration of about 0.1% to about 20%, or about 1% to about 15%, or about 2% to about 13%, by weight in the solid electrolyte.

62. The solid electrolyte of any one of claims 39 to 61, which further comprises an additive.

63. Solid electrolyte according to claim 62, in which the additive is a fluorinated compound comprising an amide function. 64.The solid electrolyte of claim 63, wherein the fluorinated compound is of formula R. 6 X 6 C(O)N(H)X 7 R 7 , where R 6 and R 7 are independently alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl groups, X 6 is O, NH or absent, and X 7 is absent or is a C(O), S(O)2, or Si(R) group 8 R 9 ), where R 8 and R 9 alkyl groups, and where at least one of R 6 , R 7 , R 8 and R 9 is a group substituted by one or more fluorine atom(s).

65. Solid electrolyte according to claim 64, in which R 6 is a perfluorinated group and X 6is absent.

66. An electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein the electrolyte is as defined in any one of claims 39 to 65.

67. An electrochemical cell according to claim 66, wherein the positive electrode comprises a positive electrode material comprising an electrochemically active positive electrode material.

68. An electrochemical cell according to claim 67, wherein the positive electrode material is on a current collector.

69. An electrochemical cell according to claim 67 or 68, wherein the electrochemically active positive electrode material is selected from metal phosphates, lithiated metal phosphates, metal oxides, and lithiated metal oxides. 70.An electrochemical cell according to claim 67 or 68, wherein the positive electrode electrochemically active material is LiM'PO4where M' is Fe, Ni, Mn, Co, or a combination of at least two thereof, LiV3O8, V2O5F, LiV2O5, LiMn2O4, LiM''O2, where M'' is Mn, Co, Ni, or a combination of at least two thereof (such as NMC, LiMnxCoyNizO2 with x+y+z = 1), Li(NiM''')O2 (where M''' is Mn, Co, Al, Fe, Cr, Ti, Zr, or a combination of at least two thereof), elemental sulfur, selenium or iodine, iron(III) fluoride, copper(II) fluoride, lithium iodide, carbon-based active materials such as graphite, active materials organic cathode, or a combination of at least two of these, when they are compatible with each other. 71.The electrochemical cell of any one of claims 67 to 70, wherein the positive electrode material further comprises an electronically conductive material, a binder, a salt, an ionic organic compound, an ionic bifunctional molecule, and / or inorganic particles.

72. The electrochemical cell of any one of claims 66 to 71, wherein the negative electrode comprises a negative electrode material comprising a negative electrode electrochemically active material.

73. The electrochemical cell of claim 72, wherein the negative electrode material is on a current collector.

74. The electrochemical cell of claim 72 or 73, wherein the negative electrode electrochemically active material comprises a metal film comprising an alkali or alkaline earth metal or an alloy comprising an alkali or alkaline earth metal.

75. The electrochemical cell of claim 74, wherein the alkali metal is selected from lithium and sodium. 76.The electrochemical cell of claim 72 or 73, wherein the negative electrode electrochemically active material comprises an intermetallic compound (e.g., SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2, and CoSn2), a metal oxide, a metal nitride, a metal phosphide, a metal phosphate (e.g., LiTi2(PO4)3), a metal halide (e.g., a metal fluoride), a metal sulfide, a metal oxysulfide, a carbon (e.g., graphite, graphene, reduced graphene oxide, hard carbon, soft carbon, exfoliated graphite, and amorphous carbon), silicon (Si), a silicon-carbon composite (Si-C), a silicon oxide (SiOx), a silicon oxide-carbon composite (SiOx-C), tin (Sn), a tin-carbon composite (Sn-C), a tin oxide (SnOx), a tin oxide-carbon composite (SnOx-C), and combinations thereof, when compatible. 77.The electrochemical cell of claim 76, wherein the metal oxide is selected from compounds of formulae M''''bOc (where M'''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof; and b and c are numbers such that the c:b ratio is in the range of 2 to 3) (e.g., MoO3, MoO2, MoS2, V2O5, and TiNb2O7), spinel oxides (e.g., NiCo2O4, ZnCo2O4, MnCo2O4, CuCo2O4, and CoFe2O4) and LiM'''''O (where M''''' is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof) (e.g., lithium titanate (such as Li4Ti5O12) or a lithium molybdenum oxide (such as Li2Mo4O13)).

78. The electrochemical cell of claim 76 or 77, wherein the negative electrode material further comprises an electronically conductive material, a binder, a salt, an ionic organic compound, an ionic bifunctional molecule, and / or inorganic particles. 79.Electrochemical accumulator comprising at least one electrochemical cell as defined in any one of claims 66 to 78.

80. Electrochemical accumulator according to claim 79, wherein said electrochemical accumulator is chosen from the group consisting of a lithium battery, a lithium-ion battery, a sodium battery, a sodium battery. ion, a potassium battery, a potassium-ion battery, a magnesium battery, and a magnesium-ion battery.

81. The electrochemical accumulator of claim 80, wherein said electrochemical accumulator is a lithium battery.

82. The electrochemical accumulator of claim 80, wherein said electrochemical accumulator is a lithium-ion battery.

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