Highly conductive boron-containing polymer electrolytes, as well as methods and compositions thereof.

Abstract

Disclosed herein are highly conductive polymer boron-containing compounds of formulas I and II, as well as electrolytes and their use in lithium batteries. To address the need for improved electrolytes for lithium batteries, highly conductive polymer electrolytes were developed. Computational modeling was used to assist in the selection of certain molecular elements (Figure 8). The electrolytes contain both acidic boron and basic oxygen atoms within their molecular structure. The presence of boron and oxygen atoms within the structure allows them to interact with both the anions and cations of the dissolved salt, functioning as ion separators by increasing the bond length between the anions and cations.

Description

Background Art

[0001] Clean and renewable energy sources that are used at a higher level than currently in use will minimize the adverse effects of fossil fuel use by reducing overall carbon emissions. (1 - 5) Therefore, the need to reduce dependence on fossil fuels and mitigate CO2 emissions has gathered global interest and requires the development of effective and efficient high-energy density power sources. (6 - 8). Promising energy storage devices are lithium-ion batteries (LIBs) and Li-air batteries (LABs), both of which use lithium ions as the main component of electrochemistry. Li batteries are rechargeable batteries commonly used in portable electronic devices, electric vehicles, and aerospace applications. (5, 6, 9 - 13) The electrolyte is an essential component of a Li-ion battery that facilitates the movement of lithium ions between the cathode and anode during charge-discharge cycles. Conventional electrolytes consist of lithium salts dissolved in organic solvents, but these electrolytes have safety issues such as leakage, flammability, and dendrite formation. There is a need for new electrolytes with improved ionic conductivity for use in Li batteries.

Brief Description of the Drawings

[0002] [Figure 1] Illustrates three interactions within an electrolyte containing both acidic and basic atoms in a polymer structure. [Figure 2] Illustrates the dispersion mechanism of Li-TFSI into a polymer matrix with or without a boron center. Insert: Ion coordination of conventional PEO and Lewis acidic polymers, and calculated charge density at the HOMO and LUMO levels. The brown circles indicate the position of the boron center and the position of charge complex formation. [Figure 3] Illustrates the 500 MHz 1H NMR spectrum of TPB350 in CDCl3. [Figure 4] Illustrates the glass transition temperatures of TB-based systems with various Li salt ratios. [Figure 5]The graph illustrates the change in CB bond elongation in Lewis acidic (boron-centered PEO) polymer matrices with (a) Li-TFSI and (b) Li-TFSI. Pink, green, white, and blue represent boron, carbon, hydrogen, and nitrogen, respectively. [Figure 6] The simulated IR spectra showing the CB binding peaks at 1040 cm⁻¹ in (a) pure triglymeboron and (b) blended triglymeboron, as well as the experimental FT-IR spectra showing the CB peaks at 1045 cm⁻¹ in (c) pure TPB350 and (d) TPB350 / LiTFSI, respectively. [Figure 7] The synthesis of boron tripegide (TPB350) is illustrated. [Figure 8] This shows schematic diagrams of conceptual, computational, and experimental designs for highly conductive boron-containing electrolytes. [Figure 9] The ionic conductivity of the TPB350 / LiTFSI electrolyte as a function of temperature is shown for [EO]:[Li+] ratios of 5, 15, 25, and 35. The PEO / P2VP / LiClO4 data is from reference 22. [Figure 10] (a) A molecular model of the top view and (b) the structure of the β-CD molecule are shown. [Figure 11] The IR spectrum of allyl-β-cyclodextrin (A-β-CD) is shown, indicating that the OH group of β-CD disappears to form A-β-CD. [Figure 12] The 1H NMR spectra of the β-CD starting material and the A-β-CD product are shown. [Figure 13] The IR spectra showing the differences between A-β-CD and β-CD-GB-MPEG are shown. [Figure 14] The 1H NMR spectra of A-β-CD and β-CD-GB-MPEG are shown. [Figure 15] The Nyquist plot of the GPE, which shows the bulk resistance used to determine ionic conductivity, is shown. [Figure 16](a) GPE-4 and (b) GPE-5 show their lithium transport fractions (LTN). [Figure 17] The results of linear sweep voltammetry (LSV) of GPE samples are shown. [Figure 18] (a) Thermal analysis by thermogravimetric analysis (TGA) and (b) thermal analysis by differential scanning calorimetry (DSC) using GPE-4 and GPE-5 are shown. [Modes for carrying out the invention]

[0003] To address the need for improved electrolytes for lithium batteries, a highly conductive polymer electrolyte was developed. Computational modeling was used to assist in the selection of certain molecular elements (Figure 8). The electrolyte contains both acidic boron and basic oxygen atoms in its molecular structure. The presence of boron and oxygen atoms in the structure allows them to interact with both the anions and cations of the dissolved salt, acting as an ion separator by increasing the bond length between the anions and cations. As a result of the increased bond length, the electrostatic interaction between the anions and cations is weakened, reducing aggregation within the electrolyte matrix and resulting in higher ionic conductivity. The new electrolyte exhibits a conductivity of 10 at 25°C. -3 S cm -1 The ionic conductivity value is shown, which is suitable for use in lithium batteries. The methods described herein demonstrate the use of computational modeling combined with experimental studies for designing and developing promising electrolytes for lithium batteries.

[0004] Herein, the subject matter of this disclosure is described more completely below. However, many modifications and other embodiments of the subject matter of this disclosure described herein will be conceivable to those skilled in the art who are interested in the teachings presented in the preceding description. Therefore, it should be understood that the subject matter of this disclosure is not limited to the specific embodiments disclosed, and that modifications and other embodiments are intended to be included within the scope of the appended claims. In other words, the subject matter described herein encompasses all alternative forms, modifications, and equivalents. If one or more incorporated documents, patents, and similar materials differ from or conflict with this application (including, but not limited to, defined terms, use of terms, and described technology), this application shall prevail. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art. All publications, patent applications, patents, and other references referred herein are invoked by reference in their entirety.

[0005] definition Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as generally understood by those skilled in the art to which the present invention belongs. Terms as defined in commonly used dictionaries should be interpreted as having the meaning consistent with their meaning in the context of this application and related art, and it will be further understood that they should not be interpreted in an ideal or overly formal sense unless expressly defined herein. The terms used herein to describe the present invention are for the sole purpose of describing specific aspects and are not intended to limit the invention. In case of any inconsistency in terminology, the foregoing shall prevail.

[0006] As used herein, the term "alkyl" refers to branched or unbranched saturated hydrocarbon groups comprising 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, and hexyl.

[0007] As used herein, the term “alkoxy” means an alkyl group linked via a single terminal ether linkage, i.e., the “alkoxy” group may be defined as -OR, where R is the alkyl group as defined above.

[0008] As used herein, the terms "and / or" include any and all possible combinations of one or more of the related enumerated items, as well as the absence of any combination when interpreted as alternative ("or").

[0009] As used herein, the terms “residue” or “residue of” a chemical moiety or compound mean a chemical moiety or compound that is attached to a molecule, thereby, through the bond, at least one covalent bond replaces at least one atom of the original chemical moiety or compound, resulting in a residue of the chemical moiety or compound within the molecule.

[0010] The term "or" refers to any one member of a given list.

[0011] Unless otherwise indicated by the context, the term “approximately” encompasses values ​​within the standard error range (e.g., SEM) of the measurement, which is a variation of ±0.5%, 1%, 5%, or 10% from the given value.

[0012] The singular forms "a," "an," and "the" refer to multiple objects unless the context explicitly indicates otherwise. For example, the terms "protein" or "at least one protein" can refer to multiple proteins, including mixtures of them.

[0013] A composition or method that "comprising" or "including" one or more of the listed elements may include other elements not specifically listed. For example, a composition that "comprises" or "includes" protein may contain protein alone or in combination with other components.

[0014] PEG-based compounds and compositions Polymer electrolytes used in lithium-ion polymer batteries exhibit relatively low ionic conductivity for several reasons, including salt aggregation within the polymer matrix. In liquid and solid solutions of the electrolyte, the majority of dissolved salts exist as dimers, tetramers, and higher-order aggregates. Aggregates are nonpolar compared to individually charged anions and cations and exist at higher concentrations within the electrolyte matrix (14-15). Due to the formation of aggregates, only a small portion of the dissolved salts functions as mobile charge carriers. Furthermore, increasing the salt content increases aggregation, which does not necessarily contribute to additional charge carriers within the matrix. Multiple interactions exist within the polymer electrolyte. To simplify the complex set of interactions, three interactions shown in Figure 1 can be considered. The three interactions are the interactions between anions and cations and the polymer backbone, as well as the electrostatic interactions between anions and cations. Optimizing these three interactions may contribute to the design and development of new electrolytes with higher conductivity. Conceptually, the electrostatic interactions between anions and cations can be sufficiently weakened by controlling the interactions between anions and cations and the polymer backbone.

[0015] Most polymer electrolytes are based on poly(ethylene oxide). Interest in ion-conducting polymer electrolytes began in 1973 when Wright et al. demonstrated ion transport in poly(ethylene oxide) / alkali metal salt blends. (16, 17) Wright's publication led to the design and development of many innovative and highly conductive electrolytes in the 1980s. (18-24) The reported electrolytes contained oxygen atoms that interacted with lithium cations, forming polymer salt complexes. In the 1980s, it was found that segmental motion of polymers facilitated ion transport within the electrolyte matrix. Thus, polymers with short oligo-oxyethylene side chains and low glass transition temperatures were synthesized. Two such polymers were comb-type polymers of oligo-oxyethylene with polysiloxane and polyphosphazene backbones. (25, 26) Since then, modified siloxane polymers have been reported. (27-29) One of the key problems with these electrolytes was that the anion transport rate was high, and anion movement was the main contributor to the overall ionic conductivity value. (30-32). Therefore, to minimize the contribution of anions to the observed ionic conductivity values, single ion (cation) conductive polymers in which anions are covalently bonded to the polymer backbone have been reported. (33-35)

[0016] To develop newer electrolytes, we prepared structures that allow control of the interactions shown in Figure 1. In ethylene oxide-based polymers, the basic oxygen atom coordinates to the lithium ion. In these polymers, since the anion is not coordinated to the polymer backbone, the anion becomes the dominant species contributing to the overall ionic conductivity. Recent studies have shown that cation diffusion can be increased by suppressing anion diffusion through the presence of Lewis acid moieties. (36) The addition of different boron structures to electrolytes has been reported to fix anions and increase cation mobility. (37, 38) Oligo(ethylene glycol) borate (OEGB), used as anion-trapping material, has the boron atom of OEGB and ClO4 -Dissociation of LiClO4 was brought about by Lewis acid-Lewis base interaction with anions. (39)

[0017] Three design requirements for developing new electrolytes are disclosed herein. (i) Ion transport is a function of the segmental motion of the polymer, and thus a polymer with a low glass transition temperature is required, (ii) the polymer needs to have the ability to dissolve salts by acid-base interaction, and (iii) the polymer contains both acids and major sites.

[0018] The method described herein utilizes computational methods to assist in identifying electrolytes with the desired properties described herein. As a first step, the method uses a model molecule having three oligo-oxyethylene arms connected to a central boron or carbon atom to utilize a first-principles study on the effect of boron centers in polymer electrolytes (Figure 2). The energetic results of ion pair dissociation and anion complexation at the boron center were calculated for Li-TFSI. Force-field-based molecular dynamics (MD) and first-principles density functional calculations were used to understand the interfacial chemistry and dispersion mechanisms. Calculations were performed to determine the 1:1 molecular ratio of the model complex between the polymer and the salt. The initial exploration of stable structures was carried out via force-field-based MD to obtain the optimal shape and characterize the electronic interaction between PEO and Li-TFSI. These energy minimizations were performed in vacuo. The resulting structures were further optimized by first-principles calculations. The binding energy was extracted from the first-principles analysis.

[0019] After introducing the boron center, the calculation results show a reduction in the binding energy between Li + and TFSI - (about 29 Kcal / mol per Li + ), that is, the ionic bond strength between Li + and TFSI - decreased from 133 kcal / mol to 104 kcal / mol. As shown in Figure 2, Li + and TFSI -The bond length between them increased from 1.8 to 2.1 Å after the addition of the boron center. In addition, Li + The interaction between the nearest oxygen atom and Li increased. + The distance to the ion decreased from 2.5 Å to 1.9 Å after the introduction of the boron center. The increase in bond length between the anion and cation and the decrease in electrostatic interaction suggest that a structure containing both basic and acidic sites can function as an ion separator.

[0020] The charge density was calculated using first-principles density functional theory. As seen in Figure 2, the dashed brown circles for LUMO and LUMO+1 highlight the locations where charge complexes are formed. The charge density distribution of LUMO+1 is shown after introducing the boron center, Li + TFSI - This indicates the formation of a charge complex between the nearest oxygen atom in the polymer matrix and the LUMO. Therefore, the charge density of the LUMO illustrates the strengthening of the interaction between the anion (TFSI) and the boron center. It is noteworthy that the aforementioned changes in the charge density distribution are not present in pure PEO polymers.

[0021] Cyclodextrin-based compounds and compositions To overcome these problems, polymers containing polyethylene oxide (PEO) are being used as liquid, gel, and slide electrolytes due to their potential, such as their ability to dissolve lithium salts. Another material being used to develop electrolytes is beta-cyclodextrin (β-CD). This material is a naturally occurring cyclic oligosaccharide composed of seven glucose units arranged in a toroidal structure, as shown in Figure 10. Researchers have been exploring its potential use as an electrolyte additive in lithium-ion batteries due to its unique properties. The beta-cyclodextrin molecule has a hydrophobic lumen and a hydrophilic outer surface, allowing it to form inclusion complexes with various guest molecules, including lithium salts.

[0022] As described herein, we use methoxy polyethylene glycol (M wA β-CD-grafted boron-polyethylene glycol (β-CD-GB-MPEG) polymer electrolyte was introduced, in which β-CD-grafted boron atoms were grafted onto 21 arms of β-CD using conjugated bonds. Then, a gel polymer electrolyte was prepared by solution casting by blending β-CD-GB-MPEG with a lithium salt using a THF solvent. Finally, the chemical, electrochemical, and thermal properties of these electrolytes were characterized.

[0023] The subject matter described herein includes, but is not limited to, the following embodiments: 1. Equation I: [ka] A compound having the structure, During the ceremony, a, b, and c are each independent integers between 1 and 15. x, y, and z are each independent integers between 1 and 6. R x , R y , and R z Each of them is independently a C1-C6 alkyl group. compound. 2. The compound according to Embodiment 1, wherein a, b, and c are each independently integers between 5 and 10. 3. The compound according to Embodiment 2, wherein a, b, and c are each 7. 4. The compound according to any one of Embodiments 1 to 3, wherein x, y, and z are each independently integers between 2 and 5. 5. The compound according to Embodiment 4, wherein x, y, and z are each 3. 6.R x , R y , and R z However, each is independently a C1-C3 alkyl compound as described in any one of Embodiments 1 to 5. 7.R x , R y , and R z The compound according to Embodiment 6, wherein each of the compounds is methyl. 8. An electrolyte composition comprising the compound and lithium salt described in any one of Embodiments 1 to 7. 9. The electrolyte composition according to Embodiment 8, wherein the lithium salt is a hydrophilic salt. 10. The electrolyte composition according to Embodiment 9, wherein the lithium salt is LiTFSI. 11. The ionic conductivity of the electrolyte composition is approximately 1.0 × 1 at approximately 25°C. -3 The electrolyte composition described above is one of any one of embodiments 8 to 10. 12. A lithium battery comprising an anode, a cathode, a lithium salt, and the compound described in Embodiment 1. 13. A lithium battery comprising an anode, a cathode, a lithium salt, and the electrolyte composition described in Embodiment 8. 14. The process involves contacting a boron / solvent complex with an allyl-alkoxyPEG polymer containing an alkene bond while stirring. A method for preparing the compound described in Embodiment 1. 15. The method according to Embodiment 14, wherein the boron / solvent is boron / THF. 16. The method according to Embodiment 14 or 15, wherein the allyl-alkoxy PEG polymer is an allyl-methoxy PEG polymer. 17. The method according to any one of Embodiments 14 to 16, wherein the allyl-methoxyPEG polymer has a molecular weight of about 100 to about 4000. 18. The method according to any one of Embodiments 14 to 17, wherein the allyl-methoxyPEG polymer has a molecular weight of about 350. 19. The method according to any one of embodiments 14 to 18, wherein the contact is made in the absence of the catalyst. 20. The method according to any one of embodiments 14 to 19, wherein the contact occurs at a temperature of approximately 22°C to approximately 0°C. 21. Structure: [ka] The compound according to Embodiment 1, having the following characteristics. 22.Structural formula II: [ka] A cyclodextrin raft boron polymer comprising a monomer having, During the ceremony, a is an integer between 6 and 8. G x , G y , and G z Each is independently selected from the group consisting of hydrogen and Q, G x , G y , and G z At least one of them is Q, Q is, [ka] And, During the ceremony, x, y, and z are each independent integers between 1 and 6. b and c are each independent integers between 1 and 15. R x and R y Each of them is independently a C1-C6 alkyl group. Cyclodextrin raft boron polymer. 23.G x , G y , and G z The cyclodextrin raft boron polymer according to Embodiment 22, wherein one or two of the atoms are hydrogen. 24. The cyclodextrin raft boron polymer according to Embodiment 22 or 23, wherein b and c are each independently integers between 5 and 10. 25. The cyclodextrin raft boron polymer according to Embodiment 24, wherein b and c are each 7. 26. A cyclodextrin raft boron polymer according to any one of embodiments 22 to 25, wherein x, y, and z are each independently integers between 2 and 5. 27. A cyclodextrin raft boron polymer according to Embodiment 26, wherein x, y, and z are each 3. 28.R x and Ry However, each is independently a C1-C3 alkyl group, as described in any one of embodiments 22 to 27, for the cyclodextrin raft boron polymer. 29.R x and R y A cyclodextrin raft boron polymer according to any one of embodiments 22 to 28, wherein each of the atoms is methyl. A cyclodextrin raft boron polymer according to any one of Embodiments 22 to 29, wherein 30.a is 7 and the cyclodextrin is β-cyclodextrin. 31. G in the cyclodextrin raft boron polymer x , G y , and G z More than 50% of the total number is Q, or G in the cyclodextrin raft boron polymer. x , G y , and G z More than 70% of the total number is Q, or G in the cyclodextrin raft boron polymer. x , G y , and G z More than 90% of the total number is Q, or G in the cyclodextrin raft boron polymer. x , G y , and G z A cyclodextrin raft boron polymer according to any one of embodiments 22 to 30, wherein more than 95% of the total number of elements is Q. 32.Q is, [ka] A cyclodextrin raft boron polymer according to any one of embodiments 22 to 31. 33. An electrolyte composition comprising the compound and lithium salt described in any one of embodiments 22 to 32. 34. The electrolyte composition according to Embodiment 33, wherein the lithium salt is a hydrophilic salt. 35. The electrolyte composition according to Embodiment 34, wherein the lithium salt is LiTFSI. 36. The ionic conductivity of the electrolyte composition is approximately 1.0 × 1 at approximately 25°C. -4 The electrolyte composition described above is one of any one of embodiments 33 to 35. 37. A lithium battery comprising an anode, a cathode, a lithium salt, and a cyclodextrin raft boron polymer as described in Embodiment 22. 38. A lithium battery comprising an anode, a cathode, a lithium salt, and the electrolyte composition described in Embodiment 33. [Examples]

[0024] This subject matter will be described in further detail with specific examples. The following examples are provided solely for illustrative purposes and are not intended to limit the invention in any way. Those skilled in the art will readily recognize various non-essential parameters that can be changed or modified to produce essentially the same results. While efforts have been made to ensure accuracy with respect to the numerical values ​​used (e.g., quantities, temperatures, etc.), some degree of experimental error and deviation may exist. Unless otherwise indicated, the practice of the subject matter described herein uses conventional chemical methods within the scope of the skill of the art. Such techniques are well described in the literature.

[0025] Example 1: Synthesis of tripegrated boron (TPB350) The tripegrated boron structure shown in Figure 7 was synthesized. Allyl-methoxypolyethylene glycol 350 (abbreviated as AMPEG350) was synthesized using the reaction shown in Figure 7. The synthesis of tripegrated boron, abbreviated as TPB350, was carried out by adding an excess amount of boron / THF complex dropwise at 0°C to a mixture of THF solution and allyl-methoxypolyethylene glycol 350 (AMPEG350). The reaction mixture was then stirred overnight at room temperature under N2 gas. Subsequently, the reaction mixture was filtered and the THF solvent was evaporated and removed. These steps were repeated two more times to confirm that each BH bond of BH3 reacted successfully with the alkene group of AMPEG to form TPB350, as shown in Figure 7. One advantage of this reaction was that it could be carried out under mild conditions without any catalysts. FT-IR spectroscopy of the obtained product showed a reaction length of 1045 cm, corresponding to the elongation of the BC bond. -1 This indicates nearby bands.

[0026] The synthesized product 1 The 1H NMR spectrum shows a peak around 1.35 ppm corresponding to (B-CH2) and a peak around 1.57 ppm corresponding to (BCC-H2C). The singlet peak at 3.37 ppm corresponds to the methyl group (CH3-). As shown in Figure 3, the peak around 3.55 ppm corresponds to (BCCCH2O-), while the peak around 3.64 ppm corresponds to the ethylene oxide (CH2CH2O) repeating unit.

[0027] Example 2: Preparation and testing of boron-containing TPB350 / LiTFSI polymer electrolyte The polymer electrolyte was prepared by mixing TPB350 and LiTFSI salt in THF solvent for 4 hours. The THF solvent was evaporated at room temperature under an N2 atmosphere. The blend was then dried in a vacuum oven at 50°C for 48 hours. + Four different electrolyte compositions were prepared with different ratios of ethylene oxide (EO) repeating units.

[0028] The electrical resistivity of all sample batches was measured using the two-terminal method, and their current (I)-voltage (V) characteristic curves (IV curves) were obtained. A Keithley Model 6430 SMU with Remote PreAmp was used and controlled by Lab Tracer software (Keithley Instruments, Inc.). Lab Tracer is powerful graphical software that runs on a PC and communicates with the instrument using a GPIB interface. A fluctuating current was passed through the outer terminal to induce a voltage in the internal voltage terminal ranging from -2.0V to +2.0V. The resistance of the samples was measured using the Keithley 6430. The resistance of the samples was determined using the two-terminal method under nitrogen gas at 25°C, 40°C, 55°C, and 70°C. Measurements were performed in both heating and cooling cycles. Each resistance measurement was repeated eight times. Conductivity was measured using copper electrodes with the sample in between. Conductivity was calculated from the bulk resistance according to the following formula. σ = (D / A) × R

[0029] In the formula, σ is conductivity, D is the thickness of the sample, A is the cross-sectional area of ​​the sample, and R is the bulk resistance.

[0030] Table 1 lists the ionic conductivity values ​​for the TPB350 / LiTFSI complex. [Table 1]

[0031] Interestingly, across a wide range of salt content, the ionic conductivity is 10 at 25°C. -3 S cm -1It was higher. Furthermore, the ionic conductivity behavior of the TPB350 / LiTFSI system differs from other electrolytes in that the conductivity value is hardly dependent on the salt content. As shown in Figure 9, the TPB350 / LiTFSI electrolyte is compared with the previous system (22). In the PEO / P2VP / LiClO4 system, the initial increase in ionic conductivity with increasing salt content is due to an initial increase in charge carriers, and further increases in salt content lead to pseudo-crosslinking of polymer chains, resulting in a reduction in segment motion and an increase in the glass transition (Tg) value. The increase in Tg value reduces ion mobility within the matrix. The initial increase in ionic conductivity, followed by a decrease, has been observed for several electrolytes, including poly(siloxane) and poly(phosphazene) electrolytes (25, 26). In the TPB350 / LiTFSI electrolyte, the ionic conductivity at 25°C is 10 over a wide range of salt content. -3 S cm -1 Because their properties were higher, they were very promising as electrolytes for lithium batteries.

[0032] The behavior of the TPB350 / LiTFSI electrolyte may be due to the role that boron atoms play within the matrix. As shown in Figure 1, in the TPB350 / LITFSI system, both anions and cations interact with the polymer structure, effectively increasing the distance between anions and cations. Therefore, TPB350 functions as an ion separator, which in turn can reduce ion aggregation. The modeling study shown in Figure 2 illustrates the effect of incorporating boron atoms into the structure, i.e., Li + It can be clearly shown that the bond length between and TFSI will increase. The increase in bond length reduces electrostatic interaction, and therefore reduces aggregation, increasing the proportion of dissolved ions that act as charge carriers. Modeling studies showed that the boron-containing structure yielded a decrease of approximately 29 kcal / mol in electrostatic interaction compared to the boron-free structure.

[0033] Figure 4 shows the DSC thermogram of the TPB350 / LiTFSI electrolyte, and Table 2 lists the glass transition temperatures. The ion separator function is possible because both anions and cations interact with TPB350. TFSI to TPB350 - The interaction was predicted by computational methods and verified by FT-IR experiments. [Table 2]

[0034] Pure TPB350 exhibits a glass transition temperature of -71°C. The Tg increases with increasing salt content. This increase in Tg can be attributed to the formation of pseudo-bridged structures due to ion-dipole interactions (25, 26). However, the effect of the Tg increase in TPB350 / LiTFSI is relatively small compared to poly(siloxane) and poly(phosphazene) electrolytes (25, 26).

[0035] The infrared spectrum of TPB350 / LiTFSI was simulated using first-principles density functional theory within the electric field linear response formulation in the CASTEP code. (40) Theoretically, the infrared absorption intensity is described in terms of a dynamic matrix known as the Hessian and Born effective charges. The Born effective charge of an ion is the partial derivative of the macropolarization with respect to the periodic displacement at zero macroscopic electric field of all periodic images of that ion. The Born effective charge tensor is calculated within the linear response formulation by applying the Gonz approximation. (41, 42) The Perdew-Burke-Ernzerhof (PBE) parameterization of the generalized gradient approximation (GGA) was used for the calculations. A kinetic energy cutoff of 630 eV at the plane wave basis and a suitable Monk-horst-Pack k-point 6×6×1 were sufficient to converge the lattice integrals of the charge density and stable conformation. An initial search for stable structures was performed by classical molecular dynamics methods. The obtained local energy minimum structure was optimized by first-principles calculations with forces less than 0.001 eV / A. A norm-conserving pseudopotential was used for IR spectroscopy calculations. Atomic position optimization was performed with an energy change of 1 × 10⁻¹⁶ per cell. -6 The process continues until the energy level drops below eV. The interaction between the boron center and the anion (TFSI) results in a strong electron supply, increasing the BC bond strength. The change in stretching frequency occurs along with the strength of the BC bond during interaction with the donor. Our results, as shown in Figure 5, show that the BC bond stretched from its initial value of 1.46 Å to 1.59 Å after interacting with TFSI, while the BC bond stretched from its initial value of 1.46 Å to 1.61 Å in the absence of TFSI. Wavenumber is proportional to energy, and angstroms are inversely proportional to energy. In IR, a blue shift in the bond frequency corresponds to an increased frequency or a shift to a higher wavenumber. A red shift indicates a decrease in frequency or a shift to a lower wavenumber. A change in absorption into the blue region of the spectrum (blue shift) is observed, indicating a transition to a higher frequency (1040 cm⁻¹). -1 From 1053cm -1The group is shown (Figure 6). Vibration analysis was performed by importing the Hessian matrix from calculations. By requesting electric field response calculations, the vibration mode frequencies and infrared intensities were displayed.

[0036] The experimental FT-IR spectrum of pure TPB350 corresponds to the extension of the CB bond at 1045 cm⁻¹. -1 The bands in the vicinity are shown. On the other hand, in the TPB350 / LiTFSI electrolyte, the band corresponding to CB binding is 1054 cm. -1 It was detected in the vicinity (Figure 6). These findings suggest that polymers without LiTFSI salts were 1040 cm². -1 Nearby, and 1052cm -1 The simulated IR spectrum showed CB extension coupling in the vicinity, which was consistent with the observed spectrum.

[0037] In conclusion, we demonstrated that computational modeling can be used to focus on specific design requirements for synthesizing novel structures to develop promising electrolytes for lithium batteries. Incorporating acidic boron and basic oxygen atoms into the design of the novel TPB350 structure, as suggested by the computational results, proved particularly useful. Within the TPB350 / LiTFSI matrix, both cations and anions interact with the TPB structure, resulting in TPB350 acting as an ion separator, i.e., increasing the bond length between anions and cations, and thus reducing electrostatic interactions. - Anion interactions were predicted by computational modeling and validated by experimental FT-IR studies. The observed ionic conductivity of the TPB / LiTFSI electrolyte was 10 over high salt content at room temperature. -3 S cm -1 The results exceeded [a certain threshold], and the system was very promising as an electrolyte for lithium batteries. This finding suggests great potential for structures containing both acidic and basic sites as effective electrolytes for lithium batteries.

[0038] Example 3: Synthesis of allyl-β-cyclodextrin (A-β-CD) The allylation of β-cyclodextrin (β-CD) was carried out based on a published protocol with slight modifications. (44) 10 g (0.0088 mol) of β-CD was dried in a vacuum oven at 100°C for 24 hours, and then dissolved by heating and stirring in a 100 mL beaker containing 50 mL of DMSO. While dissolving the β-CD, 4.5 g (0.18 mol) of NaH was added to a 500 mL three-necked round-bottom flask containing 150 mL of DMSO, and the solution mixture was stirred for 30 minutes. The β-CD solution was then added dropwise to the flask using a separatory funnel at room temperature and stirred overnight to form a highly viscous orange liquid. Subsequently, 16 mL (22.9 g, 0.18 mol) of allyl bromide was dissolved in 50 mL of DMSO and added dropwise to the flask, generating a vigorous generation of H2 gas. The reaction was allowed to proceed for 24 hours, converting the orange liquid into a golden liquid. The reaction mixture was quenched with 500 mL of distilled water. The desired product was then extracted three times from the aqueous solution with 50 mL of chloroform. The separated organic portion was washed three times again with 500 mL of dihydrate and dried overnight over calcium sulfate. The calcium sulfate was then filtered, and the solvent was removed using a rotary evaporator. After removing the chloroform solvent by flash column analysis, 8 g (46%) of the desired product was obtained, which showed the following spectral results: FT-IR: 1648 cm⁻¹ -1 (C=C), 3073cm -1 (=CH) Please refer to Figure 11. 1 H NMR(500MHz,CDCl3δppm):a,b&c)3.60-3.38ppm(m);d)3.79-3.62ppm(m);e)3.9 3-3.81ppm(d);f)4.20-4.10ppm(d);g)4.36-4.33ppm(d);h)6.02-6.00ppm(m);h * )5.88-5.83ppm(m);j)5.29-5.25ppm(d);j * ) 5.21-5.04 ppm(d) See Figure 12.

[0039] Example 4: Synthesis of β-CD-grafted boron-polyethylene glycol (β-CD-GB-MPEG) electrolyte In a suitable reactor containing 100 mL of anhydrous THF, 8.25 g (7.3 mL, 0.004 mol) of A-β-CD and 11.3 g (10.33 mL, 0.02 mol) of AMPEG were stirred while purging with N2 gas for 1 hour. Then, 0.4 g (28.8 mL, 0.028 mol) of BH3-THF was injected into the reaction mixture using a syringe, and the reaction mixture was stirred overnight at room temperature. After that, the reaction was stopped, the mixture was filtered, and the solvent was removed using a rotary evaporator to obtain 30.63 g (34 mL, 21%) of the desired product, which shows the following spectrum: FT-IR: 1030 cm⁻¹ -1 (BC) Please refer to Figure 13. 1 H NMR(500MHz,CDCl3δppm):a,b&c)3.85-3.71ppm(m);d,e&f 3.69-3.59ppm(m);j)3.48-3.36ppm(d);g)1.60-1.55ppm(d);h)1.49-1.43ppm(m),h * );i) 0.95-0.67 ppm (m) See Figure 14.

[0040] Example 5: Preparation and testing of β-CD-GB-MPEG gel polymer electrolyte Gel polymer electrolytes were prepared by blending G-β-CD with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI). As shown in Table 3, five systems were prepared, each containing a specific weight ratio of G-β-CD to LiTFSI. [Table 3]

[0041] To characterize the electrolyte system, several analyses were performed using the Admiral instrument Squidstat Plus, including electrochemical impedance spectroscopy (EIS), DC polarization (DC), and linear sweep voltammetry (LSV).

[0042] The ionic conductivity (σ) was calculated using the following formula: (Formula 1)

number

number

[0043] Bulk impedance was measured using electrochemical impedance spectroscopy (EIS) techniques. b This can usually be determined by the X-intercept (Z') at Y(Z'')=0 in the low-frequency region of the Nyquist plot, as shown in Figure 15. b To measure the properties of stainless steel (SST), each sample was placed in a symmetrical Swagelok coin cell using stainless steel (SST) as both the cathode and anode.

[0044] After measuring the bulk resistance of the samples, the ionic conductivity was measured using Equation 1, as shown in Table 4. Based on the ionic conductivity results, GPE-4 and GPE-5 were used for further electrochemical characterization due to their high ionic conductivity. [Table 4]

[0045] Lithium transport rate

number

number

Table 5

[0047] Thermal analysis was performed to investigate the thermal stability of the electrolyte system. First, thermogravimetric analysis (TGA) was performed to examine the stability of GPE-4 and GPE-5, which begin to decompose at approximately 150°C. Secondly, as shown in Figure 18, differential scanning calorimetry (DSC) was also used to investigate the thermal properties of the electrolyte system.

[0048] In conclusion, β-CD-grafted boron-polyethylene glycol (β-CD-GB-MPEG) was synthesized and characterized. Several polymer electrolytes were then prepared using it. The electrochemical and thermal properties of these electrolytes were investigated. Of the five gel polymer electrolyte systems prepared, GPE-4 and GPE-5 were found to exhibit promising performance.

[0049] Many modifications and other embodiments of the invention described herein will be apparent to those skilled in the art, who have an interest in the teachings presented in the foregoing description and the accompanying drawings. Therefore, it should be understood that the invention is not limited to the specific embodiments disclosed, and that modifications and other embodiments are intended to be included within the scope of the appended claims. Specific terms are used herein, but they are used in a general and descriptive sense only and not for limiting purposes.

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Claims

1. Formula I: 【Chemistry 1】 A compound having the structure, During the ceremony, a, b, and c are each independent integers between 1 and 15. x, y, and z are each independent integers between 1 and 6. R ｘ , R ｙ , and R ｚ Each of them is independent of C １ -C ６ It is alkyl. compound.

2. The compound according to claim 1, wherein a, b, and c are each independently integers between 5 and 10.

3. The compound according to claim 1, wherein a, b, and c are each 7.

4. The compound according to claim 1, wherein x, y, and z are each independently integers between 2 and 5.

5. The compound according to claim 4, wherein x, y, and z are each 3.

6. R ｘ , R ｙ , and R ｚ are each independently C １ -C ３ alkyl, the compound according to any one of claims 1 to 5.

7. R ｘ , R ｙ , and R ｚ The compound according to claim 6, wherein each of them is methyl.

8. An electrolyte composition comprising the compound and lithium salt described in claim 1.

9. The electrolyte composition according to claim 8, wherein the lithium salt is a hydrophilic salt.

10. The electrolyte composition according to claim 9, wherein the lithium salt is LiTFSI.

11. The ionic conductivity of the electrolyte composition is approximately 1.0 × 1 at approximately 25°C. －３ The electrolyte composition according to any one of claims 8 to 10.

12. A lithium battery comprising an anode, a cathode, a lithium salt, and the compound described in claim 1.

13. A lithium battery comprising an anode, a cathode, a lithium salt, and the electrolyte composition according to claim 8.

14. The process involves contacting a boron / solvent complex with an allyl-alkoxyPEG polymer containing an alkene bond while stirring. A method for preparing the compound described in claim 1.

15. The method according to claim 14, wherein the boron / solvent is boron / THF.

16. The method according to claim 14, wherein the allyl-alkoxyPEG polymer is an allyl-methoxyPEG polymer.

17. The method according to any one of claims 14 to 16, wherein the allyl-methoxyPEG polymer has a molecular weight of about 100 to about 4000.

18. The method according to claim 17, wherein the allyl-methoxyPEG polymer has a molecular weight of about 350.

19. The method according to claim 14, wherein the contact occurs in the absence of a catalyst.

20. The method according to claim 14, wherein the contact occurs at a temperature of approximately 22°C to approximately 0°C.

21. structure: 【Chemistry 2】 The compound according to claim 1, having the following characteristics.

22. Structural formula II: 【Transformation 3】 A cyclodextrin raft boron polymer comprising a monomer having, During the ceremony, a is an integer between 6 and 8. G ｘ G ｙ , and G ｚ Each is independently selected from the group consisting of hydrogen and Q, G ｘ G ｙ , and G ｚ At least one of them is Q, Q is, 【Chemistry 4】 The following: During the ceremony, x, y, and z are each independent integers between 1 and 6. b and c are each independent integers between 1 and 15. R ｘ and R ｙ Each of them is independent of C １ -C ６ A cyclodextrin raft boron polymer, which is alkyl.

23. G ｘ G ｙ , and G ｚ The cyclodextrin raft boron polymer according to claim 22, wherein one or two of the atoms are hydrogen.

24. The cyclodextrin raft boron polymer according to claim 22, wherein b and c are each independently integers between 5 and 10.

25. The cyclodextrin raft boron polymer according to claim 24, wherein b and c are each 7.

26. The cyclodextrin raft boron polymer according to claim 22, wherein x, y, and z are each independently integers between 2 and 5.

27. The cyclodextrin raft boron polymer according to claim 26, wherein x, y, and z are each 3.

28. R ｘ and R ｙ However, each is independent of C １ -C ３ The cyclodextrin raft boron polymer according to claim 22, wherein the polymer is alkyl.

29. R ｘ and R ｙ The cyclodextrin raft boron polymer according to claim 28, wherein each of the atoms is methyl.

30. The cyclodextrin raft boron polymer according to claim 22, wherein a is 7 and the cyclodextrin is β-cyclodextrin.

31. G in the cyclodextrin raft boron polymer ｘ G ｙ , and G ｚ More than 50% of the total number is Q, or G in the cyclodextrin raft boron polymer. ｘ G ｙ , and G ｚ More than 70% of the total number is Q, or G in the cyclodextrin raft boron polymer. ｘ G ｙ , and G ｚ More than 90% of the total number is Q, or G in the cyclodextrin raft boron polymer. ｘ G ｙ , and G ｚ The cyclodextrin raft boron polymer according to claim 22, wherein 95% or more of the total number of elements is Q.

32. Q is, 【Transformation 5】 The cyclodextrin raft boron polymer according to any one of claims 22 to 31.

33. An electrolyte composition comprising the compound and lithium salt described in claim 22.

34. The electrolyte composition according to claim 33, wherein the lithium salt is a hydrophilic salt.

35. The electrolyte composition according to claim 34, wherein the lithium salt is LiTFSI.

36. The ionic conductivity of the electrolyte composition is approximately 1.0 × 1 at approximately 25°C. －４ The electrolyte composition according to claim 33.

37. A lithium battery comprising an anode, a cathode, a lithium salt, and the cyclodextrin raft boron polymer according to claim 22.

38. A lithium battery comprising an anode, a cathode, a lithium salt, and the electrolyte composition according to claim 33.

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