US 12,009,481 B2
Electrolytes for fast charging lithium ion batteries having four-carbon chain esters as linear components
Nir Kedem, Haifa (IL); Liron Amir, Ramat Gan (IL); Evgenia Liel (Jeny) Kuks, Ramat Gan (IL); Ido Herzog, Tel Aviv (IL); Shirel Cohen, Tel aviv (IL); Rony Schwarz, Kibbutz Ma'anit (IL); and Eran Sella, Tel Aviv (IL)
Assigned to StoreDot Ltd., Herzeliya (IL)
Filed by StoreDot Ltd., Herzeliya (IL)
Filed on Jan. 28, 2020, as Appl. No. 16/774,003.
Prior Publication US 2021/0242500 A1, Aug. 5, 2021
Int. Cl. H01M 10/0569 (2010.01); H01M 4/38 (2006.01); H01M 10/0525 (2010.01); H01M 10/0567 (2010.01)
CPC H01M 10/0569 (2013.01) [H01M 4/386 (2013.01); H01M 4/387 (2013.01); H01M 10/0525 (2013.01); H01M 10/0567 (2013.01); H01M 2300/0051 (2013.01)] 16 Claims
OG exemplary drawing
 
1. An electrolyte solution for a charging of a lithium ion battery at a rate of at least 4 C, comprising:
linear solvent comprising at least one four-carbon chain ester,
cyclic carbonate solvent comprising at least vinyl carbonate (VC) solvent, additives at an amount smaller than 5 wt %, wherein the additives comprise:
a first additive that is represented by tertamilbenzene (t-AmB):

OG Complex Work Unit Chemistry
and at least one second additive that comprises at least one of: compound 1a, compound 35, and compound 36; and
at least one lithium salt,
wherein the at least one four-carbon chain ester is represented by the structure of Formula (XVIa), Formula (XVIb) or any combination thereof:

OG Complex Work Unit Chemistry
wherein
R48′ is a C3-C10 alkyl, C3-C20 alkyl or C3-C30 alkyl;
R49′ is C4-C10 alkyl, C4-C20 alkyl or C4-C30 alkyl;
R48 is alkyl, haloalkyl, cycloalkyl, aryl, heteroalicyclic, benzyl or heteroaryl;
R49 is alkyl, haloalkyl, cycloalkyl, aryl, heteroalicyclic, benzyl or heteroaryl;
each of the alkyl, haloalkyl, cycloalkyl, aryl, heteroalicyclic, benzyl or heteroaryl of R48, R48′, R49 or R49′ is optionally substituted with one or more of alkyl, haloalkyl, alkenyl, alkynyl, heteroalicyclic, heteroaryl, O—P(═O)(OR48)2, trihalomethyl, cyano, S(═O)—R48, S(═O)2—R48, S(═O)2—NR48R49, halide, cycloalkyl, alkoxy, nitro, NR48R49, C(O)NR48R49, N(R48)C(═O)—R49, hydroxy, alkylthiol, thiol, arylthiol, heteroarylthiol, C(═O)—OR48, C(═O)—R48, aryl, aryloxy, heteroaryloxy, (CH2CH2O)n+1 or any combination thereof;

OG Complex Work Unit Chemistry
and
n is an integer between 0 and 10.
 
7. An electrolyte solution for a charging lithium ion battery at a rate of at least 4 C, comprising:
linear solvent comprising at least one four-carbon chain ester,
cyclic carbonate solvent comprising at least vinyl carbonate (VC) solvent,
wherein a weight percentage of the at least one four-carbon chain ester is larger than a weight percentage of the cyclic carbonate solvent,
at least one lithium salt, and
additives that comprise a first additive that is represented by tertamilbenzene (t-AmB):

OG Complex Work Unit Chemistry
the structure of Formula (I) or any combination thereof:

OG Complex Work Unit Chemistry
wherein:
Z1 is halide, alkyl, haloalkyl, aryl, alkenyl, alkynyl, cycloalkyl, heteroaryl, heteroalicyclic, hydroxyl, alkoxy, aryloxy, heteroaryloxy, NR1R2, P(═O)R1R2, benzyl, thiol, arylthiol, alkylthiol, heteroarylthiol, O(CH2)nC4H4S, amino pyridine, imidazole, cyclic amine, piperazine, N(CH2CH2)2N—C(═S)—S—Z2, a polymeric moiety or an oligomeric moiety;
Z2 is alkyl, haloalkyl, benzyl, aryl, cycloalkyl, alkenyl, alkynyl, heteroalicyclic, heteroaryl, a polymeric moiety, CH(P(═O)(OR1)2)((C═O)OR2), CH2C6H5, (CH2)n(CO)NR1R2, (CH2)nCOOR1, (CH2)n(CO)NH(C5H4N), (CH2)nSR1, (CH2)nS(═O)R1, (CH2)nS(═O)2R1,

OG Complex Work Unit Chemistry
an oligomeric moiety or S—C(═S)—Z1;
R1-R2 are each independently H, alkyl, haloalkyl, cycloalkyl, benzyl, aryl, heteroalicyclic, heteroaryl, polymeric moiety or an oligomeric moiety, wherein if nitrogen (N) is adjacent to R1 and R2 then R1, R2 and the adjacent nitrogen may form a heteroaryl or a heteroalicyclic ring;
each of the alkyl, haloalkyl, aryl, benzyl, alkenyl, alkynyl, cycloalkyl, heteroaryl, heteroalicyclic, alkoxy, aryloxy, heteroaryloxy, polymeric moiety, oligomeric moiety arylthiol, alkylthiol or heteroarylthiol of Z1, Z2, R1 or R2 is optionally substituted with one or more of alkyl, haloalkyl, alkenyl, alkynyl, heteroalicyclic, heteroaryl, O—P(═O)(OR1)2, trihalomethyl, S(═O)—R1, S(═O)2—R1, S(═O)2—NR1R2, halide, cycloalkyl, alkoxy, nitro, cyano, NR1R2, C(O)NR1R2, N(R1)C(═O)—R2, hydroxy, alkylthiol, thiol, arylthiol, heteroarylthiol, C(═O)—OR1, C(═O)—R1, aryl, aryloxy, heteroaryloxy, (CH2CH2O)n+1 or any combination thereof;
wherein the additives comprise at least one second additive out of compound 1a, compound or compound 36

OG Complex Work Unit Chemistry
and n is an integer between 0 and 10.