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US 2021/0202992 A1Published application
Electrolyte composition comprising oligomeric silyl ester phosphonates
AssigneeBASF SE
InventorsManuel Alejandro MENDEZ AGUDELO, Johannes David HOECKER
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Abstract
An electrolyte composition containing (i) at least one aprotic organic solvent; (ii) at least one conducting salt; (iii) at least one silyl ester phosphonate containing the structure of formula (I), wherein T is selected from (Ia) and (Ib); and (iv) optionally one or more additives.
Claims15
1:
- An electrolyte composition, comprising:
- at least one aprotic organic solvent;
- at least one conducting salt;
- at least one silyl ester phosphonate containing having the structure of formula (I):
- and optionally one or more additives,
- wherein:
- T is selected from the group consisting of
- p is an integer from 0 to 6;
- and
- one or more CH2 groups of (CH2)p are optionally replaced by O;
- one or more H of (CH2)p are optionally replaced by C1-C4 alkyl;
- each R1 is independently selected from the group consisting of H, F, Cl, R4, OR4, OSi(R5)3, OSi(OR4)3, and OP(O)(OR4)R5;
- each R4 is independently selected from the group consisting of C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl;
- each R4 is independently and optionally substituted by one or more substituents selected from the group consisting of CN and F;
- one or more CH2-groups of alkyl, alkenyl, and alkynyl, if present in R4 and not directly bound to Si or O are optionally replaced by O;
- R3 and R5 are each independently selected from the group consisting of H, F, C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl;
- each optionally substituted by one or more substituents selected from the group consisting of CN and F;
- and
- one or more CH2-groups of alkyl, alkenyl, and alkynyl, if present in R3 and/or R5 and not directly bound to P, are optionally replaced by O.
16 more elements
2:
- The electrolyte composition of claim 1, wherein the at least one silyl ester phosphonate comprises the structure of formula (II):
- wherein Q1 is a chemical bond or a monomeric or oligomeric group comprising one or more monomeric units of formula (II.1), and Q2 is a chemical bond or a monomeric or oligomeric group comprising one or more monomeric units of formula (II.2):
- wherein each T* is independently Si or Si—(CH2)x—Si, wherein x is an integer of 0 to 6, one or more CH2 groups of Si—(CH2)x—Si are optionally replaced by O, and one or more H of Si—(CH2)—Si are optionally replaced by C1-C4 alkyl,
- wherein if T* is Si:
- q1 is an integer from zero to 2,
- q2 is an integer from zero to 2, and
- q1+q2=2,
- wherein if T* is Si—(CH2)x—Si:
- q1 is an integer from zero to 4,
- q2 is an integer from zero to 4, and
- q1+q2=4;
- and
- wherein—* is a continuation of the silylester phosphonate backbone by branching.
10 more elements
3:
- The electrolyte composition of claim 2, wherein the at least one silyl ester phosphonate has the formula (III):
- wherein R6 and R7 are each independently selected from the group consisting of R8, Si(OR8)3, and Si(R9)3;
- wherein each R8 is independently selected from the group consisting of C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl,
- wherein each R8 is optionally substituted by one or more substituents selected from CN and F, and wherein one or more CH2-groups of alkyl, alkenyl, and alkynyl which are not directly bound to O or Si are optionally replaced by O;
- and
- wherein each R9 is independently selected from the group consisting of H, F, Cl, C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl,
- wherein each R9 is optionally substituted by one or more substituents selected from CN and F, and wherein one or more CH2-groups of alkyl, alkenyl, and alkynyl which are not directly bound to O are optionally replaced by O.
4 more elements
4:
- The electrolyte composition of claim 2, wherein the at least one silyl ester phosphonate has the formula (IV):
- wherein r1 and r2 are each independently integers from 0 to 300.
5:
- The electrolyte composition of claim 3, wherein R6 and R7 are each independently selected from the group consisting of C1-C10 alkyl, Si(OC1-C10alkyl)3, and Si(R9)3, and
- wherein each R9 is independently selected from the group consisting of H, F, Cl, and C1-C10 alkyl.
6:
- The electrolyte composition of claim 1, wherein each R1 is independently selected from the group consisting of H, F, Cl, C1-C10 alkyl, and OC1-C10 alkyl, and
- wherein the C1-C10 alkyl and/or the OC1-C10 alkyl is optionally substituted by one or more substituents selected from the group consisting of CN and F, and wherein one or more CH2-groups of the C1-C10 alkyl and/or the OC1-C10 alkyl which are not directly bound to Si or O are optionally replaced by O.
7:
- The electrolyte composition of claim 1,
- wherein each R3 is independently selected from the group consisting of H and C1-C10 alkyl,
- wherein each R3 is optionally substituted by one or more F and/or CN, and
- wherein one or more CH2-groups of the C1-C10 alkyl which are not directly bound to P are optionally replaced by O.
1 more element
8:
- The electrolyte composition of claim 1, wherein the structure of formula (I) is selected from the group consisting of
9:
- The electrolyte composition of claim 1, wherein the at least one aprotic organic solvent is selected from the group consisting of
- a fluorinated cyclic organic carbonate, a non-fluorinated cyclic organic carbonate, a fluorinated acyclic organic carbonate, and a non-fluorinated acyclic organic carbonate,
- a fluorinated ether, a non-fluorinated ether, a fluorinated polyether, a non-fluorinated polyether,
- a fluorinated cyclic ether, a non-fluorinated cyclic ether,
- a fluorinated cyclic acetal, a non-fluorinated cyclic acetal, a fluorinated cyclic ketal, a non-fluorinated cyclic ketal, a fluorinated acyclic acetal, a non-fluorinated acyclic acetal, a fluorinated acyclic ketal, a non-fluorinated acyclic ketal,
- a fluorinated orthocarboxylic acid ester, a non-fluorinated orthocarboxylic acid ester,
- a fluorinated cyclic ester of a carboxylic acid, a non-fluorinated cyclic ester of a carboxylic acid, a fluorinated cyclic diester of a carboxylic acid, a non-fluorinated cyclic diester of a carboxylic acid, a fluorinated acyclic ester of a carboxylic acid, a non-fluorinated acyclic ester of a carboxylic acid, a fluorinated acyclic diester of a carboxylic acid, a non-fluorinated acyclic diester of a carboxylic acid,
- a fluorinated cyclic sulfone, a non-fluorinated cyclic sulfone, a fluorinated acyclic sulfone, a non-fluorinated acyclic sulfone,
- a fluorinated cyclic nitrile, a non-fluorinated cyclic nitrile, a fluorinated cyclic dinitrile, a non-fluorinated cyclic dinitrile, a fluorinated acyclic nitrile, a non-fluorinated acyclic nitrile, a fluorinated acyclic dinitrile, a non-fluorinated acyclic dinitrile,
- a fluorinated cyclic phosphate, a non-fluorinated cyclic phosphate, a fluorinated acyclic phosphate, and a non-fluorinated acyclic phosphate.
7 more elements
10:
- The electrolyte composition of claim 1, wherein the at least one aprotic organic solvent comprises at least one solvent selected from the group consisting of a fluorinated ether, a non-fluorinated ether, a fluorinated polyether, a non-fluorinated polyether, a fluorinated cyclic organic carbonate, a non-fluorinated cyclic organic carbonate, a fluorinated acyclic organic carbonate, and a non-fluorinated acyclic organic carbonate.
11:
- The electrolyte composition of claim 1, wherein the at least one conducting salt is at least one lithium salt.
12:
- The electrolyte composition of claim 1, wherein the electrolyte composition comprises 0.01 to 10 wt.-% of the at least one silyl ester phosphonate based on the total weight of the electrolyte composition.
13:
- A method of making an electrochemical cell, comprising:
- providing an electrolyte composition along with a positive electrode and a negative electrode,
- wherein the electrolyte composition comprises a silyl ester phosphonate comprising the structure of formula (I):
- wherein:
- T is selected from the group consisting of
- p is an integer from 0 to 6;
- one or more CH2 groups of (CH2)p are optionally replaced by O;
- one or more H of (CH2)p are optionally replaced by C1-C4 alkyl;
- each R1 is independently selected from the group consisting of H, F, Cl, R4, OR4, OSi(R5)3, OSi(OR4)3, and OP(O)(OR4)R5;
- each R4 is independently selected from the group consisting of C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl;
- each R4 is independently and optionally substituted by one or more substituents selected from the group consisting of CN and F;
- one or more CH2-groups of alkyl, alkenyl, and alkynyl, if present in R4 and not directly bound to Si or O are optionally replaced by O;
- R3 and R5 are each independently selected from the group consisting of H, F, C1-C10 alkyl, C3-C7 (hetero)cycloalkyl, C2-C10 alkenyl, C2-C 10 alkynyl, C5-C7 (hetero)aryl, and C6-C13 (hetero)aralkyl;
- each optionally substituted by one or more substituents selected from the group consisting of CN and F;
- and
- one or more CH2-groups of alkyl, alkenyl, and alkynyl, if present in R3 and/or R5 and not directly bound to P, are optionally replaced by O.
13 more elements
14:
- An electrochemical cell, comprising the electrolyte composition of claim 1.
15:
- The electrochemical cell of claim 14, wherein the electrochemical cell is a lithium battery, a double layer capacitor, or a lithium ion capacitor.