# US 2017/0288288 A1 · Acrylonitrile derivatives as additive for electrolytes in lithium ion batteries

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- Number: US 2017/0288288 A1
- Document ID: US20170288288A1
- Status: Published application
- Kind: A1
- Application number: 15/623,205
- Filed: 2017-06-14
- Published: 2017-10-05
- Earliest claimed: 2013-07-15
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Frederick Francois Chesneau; Zoltan Baan; Boris Gaspar; Michael Schmidt; Arnd Garsuch; Hannes Wolf; Klaus Leitner; Christian Saffert; Wolfgang Klaus; Melanie Kuhl
- Web page: https://patentgrep.com/patent/US20170288288A1

## CPC

- H01M 10/0567: characterised by the additives
- H01M 4/131: Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx
- H01M 4/133: Electrodes based on carbonaceous material, e.g. graphite-intercalation compounds or CFx
- H01M 4/505: of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
- H01M 4/525: of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
- H01M 4/587: for inserting or intercalating light metals
- H01M 4/625: {Carbon or graphite}
- H01M 4/661: {Metal or alloys, e.g. alloy coatings (H01M4/669 take precedence)}
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- H01M 50/44: Fibrous material
- H01M 4/0404: {by coating on electrode collectors}
- H01M 4/1391: of electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx
- H01M 50/437: Glass
- H01M 2004/027: {Negative electrodes}
- H01M 2004/028: {Positive electrodes}
- H01M 2220/10: Batteries in stationary systems, e.g. emergency power source in plant
- H01M 2220/20: Batteries in motive systems, e.g. vehicle, ship, plane
- H01M 2220/30: Batteries in portable systems, e.g. mobile phone, laptop
- Y02E 60/10: Energy storage using batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An electrolyte composition (A) containing (i) at least one aprotic organic solvent; (ii) at least one conducting salt; (iii) at least one compound of formula (I) wherein X1 and X2 are independently from each other selected from N(R1), P(R1), O, and S, Y1 and Y2 are independently from each other selected from (O), (S), (PR2) and (NR2); and electrochemical cells containing electrolyte composition (A).

## Claims

### Claim at position 1

1: An electrolyte composition (A), comprising:
at least one aprotic organic solvent;
at least one conducting salt;
at least one compound of formula (I)
wherein
X1 and X2 are each independently N(R1), P(R1), O, or S;
R1 is H, C1-C10 alkyl, C3-C6 (hetero)cycloalkyl, C2-C10 alkenyl, C3-C6 (hetero)cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, C7-C13 aralkyl, OR3, C(O)R3, C(NR3)R4, or C(O)OR3, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7 (hetero)aryl, S(O)2OR3a, OS(O)2R3a, S(O)2R3a, OR3a, C(O)R3a, C(O)OR3a, NR3aR3b, and NC(O)R3aR3b;
Y1 and Y2 are each independently (O), (S), (PR2) and or (NR2),
R2 is H, C1-C10 alkyl, C3-C6 (hetero)cycloalkyl, C2-C10 alkenyl, (hetero)C3-C6 cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, C7-C13 aralkyl, OR2a or C(O)R2a, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7 (hetero)aryl, S(O)2OR2b, OS(O)2R2b, S(O)2R2b, OR2b, C(O)R2b, C(O)OR2b, NR2bR2c, and NC(O)R2bR2c; and
R2a, R2b and R2c are each independently H, C1-C10 alkyl, C3-C6 (hetero)cycloalkyl, C2-C10 alkenyl, or C5-C7 (hetero)aryl, wherein alkyl, (hetero)cycloakyl, alkenyl, and (hetero)aryl may be substituted by one or more substituents selected from F and CN,
R3, R4, R3a, and R3b are each independently H, C1-C10 alkyl, C3-C6 (hetero)cycloalkyl, C2-C10 alkenyl, C3-C6 (hetero)cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, or C7-C13 aralkyl, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7(hetero)aryl, S(O)2OR3c, OS(O)2R3c, S(O)2R3c, OR3c, C(O)R3c, C(O)OR3c, NR3cR3d, and NC(O)R3cR3d;
R3c and R3d are each independently H, C1-C10 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, or C5-C7 (hetero)aryl, wherein alkyl, (hetero)cycloalkyl, alkenyl, and (hetero)aryl may be substituted by one or more substituents selected from F and CN;
and
(iv) optionally, at least one further additive.

### Claim 2 (depends on 1)

The electrolyte composition (A) according to claim 1 wherein both Y1 and Y2 are the same and are (O) or NR1.

### Claim 3 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the at least one compound of formula (I) is compound (I. 1)

### Claim 4 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the at least one compound of formula (I) is a compound of formula (I) wherein X1 and X2 are each independently N(R1) or O.

### Claim 5 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the aprotic organic solvent (i) is selected from the group consisting of
(a) cyclic and noncyclic organic carbonates, which may be optionally partly halogenated,
(b) di-C1-C10-alkylethers, optionally partly halogenated,
(c) di-C1-C4-alkyl-C2-C6-alkylene ethers and polyethers, optionally partly halogenated,
(d) cyclic ethers, optionally partly halogenated.
(e) cyclic and acyclic acetals and ketals, optionally partly halogenated,
(f) orthocarboxylic acids esters, optionally partly halogenated,
(g) cyclic and noncyclic esters of carboxylic acids, optionally partly halogenated,
(h) cyclic and noncyclic sulfones, optionally partly halogenated,
(i) cyclic and noncyclic nitriles and dinitriles, optionally partly halogenated, and
(j) ionic liquids, optionally partly halogenated.

### Claim 6 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the electrolyte composition (A) comprises at least one aprotic solvent (i) selected from cyclic organic carbonates and at least one aprotic organic solvent (i) selected from noncyclic organic carbonates.

### Claim 7 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the conducting salt (ii) is selected from the group consisting of
Li[F6−xP(CyF2y+1)x], wherein x is an integer in the range from 0 to 6 and y is an integer in the range from 1 to 20;
Li[B(RI)4], Li[B(RI)2(ORIIO)] and Li[B(ORIIO)2] wherein each RI is independently F, Cl, Br, I, C1-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl, wherein alkyl, alkenyl, and alkynyl may be substituted by one or more ORIII, wherein RIII is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, and C2-C6 alkynyl and (ORIIO) is a bivalent group derived from a 1,2- or 1,3-diol, a 1,2- or 1,3-dicarboxlic acid or a 1,2- or 1,3-hydroxycarboxylic acid, wherein the bivalent group forms a 5- or 6-membered cycle via the both oxygen atoms with the central B-atom;
LiClO4; LiAsF6; LiCF3SO3; Li2SiF6; LiSbf6; LiAlCl4, lithium tetrafluoro (oxalato) phosphate; lithium oxalate; and
salts of formula Li[Z(CnF2n+1SO2)m], wherein
m=1 when Z is selected from oxygen and sulfur,
m=2 when Z is selected from nitrogen and phosphorus,
m=3 when Z is selected from carbon and silicon, and
n is an integer in the range from 1 to 20.

### Claim 8 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the electrolyte composition (A) further comprises at least one additive (iv) selected from the group consisting of vinylene carbonate and its derivatives, vinyl ethylene carbonate and its derivatives, methyl ethylene carbonate and its derivatives, lithium (bisoxalato) borate, lithium difluoro (oxalato) borate, lithium tetrafluoro (oxalato) phosphate, lithium oxalate, 2-vinyl pyridine, 4-vinyl pyridine, cyclic exo-methylene carbonates, sultones, organic esters of inorganic acids, acyclic and cyclic alkanes having a boiling point at 1 bar of at least 36° C., and aromatic compounds, optionally halogenated cyclic and acyclic sulfonylimides, optionally halogenated cyclic and acyclic phosphate esters, optionally halogenated cyclic and acyclic phosphines, optionally halogenated cyclic and acyclic phosphites, optionally halogenated cyclic and acyclic phosphazenes, optionally halogenated cyclic and acyclic silylamines, optionally halogenated cyclic and acyclic halogenated esters, optionally halogenated cyclic and acyclic amides, optionally halogenated cyclic and acyclic anhydrides, ionic liquids, and optionally halogenated organic heterocycles.

### Claim 9 (depends on 1)

The electrolyte composition (A) according to claim 1, wherein the concentration of the at least one compound of formula (I) is 0.001 to 10 wt-%, based on the total weight of the electrolyte composition (A).

### Claim 10 (depends on 1)

The electrolyte composition (A) according claim 1, wherein the concentration of the at least one compound of formula (I) is from 0.01 to 2 wt.-%, based on the total weight of the electrolyte composition (A).

### Claim 11

A method to prepare an electrolyte for an electrochemical cell, comprising:
adding a compound of formula (I) to the electrolyte:
wherein
X1 and X2 are each independently N(R1), P(R1), O, or S;
R1 is H, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C3-C6 (hetero)cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, C7-C13 aralkyl, OR3, C(O)R3, C(NR3)R4, or C(O)OR3, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7 (hetero)aryl, S(O)2OR3a, OS(O)2R3a, S(O)2R3a, OR3a, C(O)R3a, C(O)OR3a, NR3aR3b, and NC(O)R3aR3b;
Y1 and Y2 are each independently (O), (S), (PR2) or (NR2),
R2 is H, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, (hetero)C3-C6 cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, C7-C13 aralkyl, OR2a or C(O)R2a, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7 (hetero)aryl, S(O)2OR2b, OS(O)2R2b, S(O)2R2b, OR2b, C(O)R2b, C(O)OR10b, NR2bR2c, and NC(O)R2bR2c; and
R2a, R2b and R2c are each independently H, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, or C5-C7 (hetero)aryl, wherein alkyl, (hetero)cycloalkyl, alkenyl, and (hetero)aryl may be substituted by one or more substituents selected from F and CN,
R3, R4, R3a, and R3b are each independently H, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C3-C6 (hetero)cycloalkenyl, C2-C6 alkynyl, C5-C7 (hetero)aryl, or C7-C13 aralkyl, wherein alkyl, (hetero)cycloalkyl, alkenyl, (hetero)cycloalkenyl, alkynyl, (hetero)aryl, and aralkyl may be substituted by one or more substituents selected from the group consisting of F, CN, C1-C6 alkyl, C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, C5-C7 (hetero)aryl, S(O)2OR3c, OS(O)2R3c, S(O)2R3c, OR3c, C(O)R3c, C(O)OR3c, NR3cR3d, and NC(O)R3cR3d;
R3c and R3d are each independently H, C1-C6 alkyl C3-C6 (hetero)cycloalkyl, C2-C6 alkenyl, or C5-C7(hetero)aryl, wherein alkyl, (hetero)cycloalkyl, alkenyl, and (hetero)aryl may be substituted by one or more substituents selected from F and CN.

### Claim 12 (depends on 1)

An electrochemical cell comprising
(A) the electrolyte composition according to claim 1,
(B) at least one cathode comprising at least one cathode active material, and
(C) at least one anode comprising at least one anode active material.

### Claim 13 (depends on 12)

The electrochemical cell according to claim 12 wherein the electrochemical cell is a secondary lithium ion battery.

### Claim 14 (depends on 12)

The electrochemical cell according to claim 12 wherein the at least one cathode active material comprises a material selected from lithiated transition metal phosphates and lithium ion intercalating transition metal oxides.

### Claim 15 (depends on 12)

The electrochemical cell according to claim 12, wherein the at least one anode active material comprises a material selected from lithium ion intercalating carbonaceous material, lithium ion intercalating oxides of Ti, and lithium ion uptaking silicon.