发明名称 COMPOUNDS CONTAINING ALKYL-CYANO-BORATE OR ALKYL-CYANO-FLUOROBORATE ANIONS
摘要 The invention relates to new compounds containing alkyl/alkenyl-cyano-borate or alkyl/alkenyl-cyano-fluoroborate anions, their preparation and their use, in particular as part of electrolyte formulations for electrochemical or optoelectronic devices.
申请公布号 US2014155566(A1) 申请公布日期 2014.06.05
申请号 US201214131990 申请日期 2012.07.06
申请人 Ignatyen Nikolai (Mykola);Schulte Michael;Kawata Kentaro;Goto Tomohisa;Sprenger Jan;Finze Maik;Frank Walter 发明人 Ignatyen Nikolai (Mykola);Schulte Michael;Kawata Kentaro;Goto Tomohisa;Sprenger Jan;Finze Maik;Frank Walter
分类号 H01G9/20 主分类号 H01G9/20
代理机构 代理人
主权项 1. Compounds of formula I [Kt]z+z[(R1)4−x−y−vB(CN)x(NC)yFv]−  Iin which R1 each independently denotes a straight-chain or branched alkyl group having 1 to 20 C atoms, which optionally may contain at least one Cl, Br or I atom, at least one CN group and/or one or more oxygen or sulphur atoms, a straight-chain or branched alkenyl group having 2 to 20 C atoms having one or more double bonds, which optionally may contain at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms, a straight-chain or branched alkinyl group having 1 to 20 C atoms having one or more triple bonds, which optionally may contain at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms and optionally may have a double bond, or unsubstituted phenyl, z is 1, 2, 3 or 4, x is 1, 2 or 3, y is 0, 1 or 2, v is 0, 1 or 2 and the sum of x+y+v is 2 or 3 and in which Ktz+ denotes an inorganic cation selected from the group of NO+, H+, Li+, Na+, K+, Rb+, Cs+, or Mg2+, Cu+, Cu2+, Zn2+, Ag+, Ca2+, Y+3, Yb+3, La+3, Sc+3, Ce+3, Nd+3, Tb+3, Sm+3 or complex (ligands containing) metal cations which include rare-earths, transitions or noble metals like rhodium, ruthenium, iridium, palladium, platinum, osmium, cobalt, nickel, iron, chromium, molybdenum, tungsten, vanadium, titanium, zirconium, hafnium, thorium, uranium, gold, or an organic cation selected from the group of a tritylium cation, in which the phenyl groups may be substituted by straight-chain or branched alkyl groups having 1 to 20 C atoms, straight-chain or branched alkenyl having 2 to 20 C atoms and one or more double bonds or straight-chain or branched alkynyl having 2 to 20 C atoms and one or more triple bonds, an oxonium cation of formula (1) or a sulfonium cation of formula (2)) [(Ro)3O]+  (1))[(Ro)3S]+  (2),where Ro each independently of one another denotes a straight-chain or branched alkyl group having 1-8 C atoms, non-substituted phenyl or phenyl which is substituted by R1*, OR′, N(R′)2, CN or halogen and in case of sulfonium cations of formula (2) additionally denotes each independently (R′″)2N and R′ is independently of each other H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, R1* is independently of each other non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and R′″ is independently of each other straight-chain or branched C1 to C6 alkyl; an ammonium cation, which conforms to the formula (3) [NR4]+  (3),where R in each case, independently of one another, denotes H, OR′, N(R′)2, with the proviso that a maximum of one R in formula (3) is OR′ or N(R′)2, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two R may be fully substituted by halogens, in particular —F and/or —Cl, and one or more of the substituents R may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, —CN, —N(R′)2, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —NO2, —SR′, —S(O)R′, —SO2R′ and where one or two non-adjacent carbon atoms in R which are not in the α-position may be replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen; a phosphonium cation, which conforms to the formula (4) [P(R2)4]+  (4),where R2 in each case, independently of one another, denotes H, OR′ or N(R′)2, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two R2 may be fully substituted by halogens, in particular —F and/or —Cl, and one or more of the substituents R2 may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, —CN, —N(R′)2, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —NO2, —SR′, —S(O)R′, —SO2R′ and where one or two non-adjacent carbon atoms in R2 which are not in the α-position may be replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen; a uronium cation, which conforms to the formula (5) [C(NR3R4)(OR5)(NR6R7)]+  (5),where R3 to R7 each, independently of one another, denote H, where H is excluded for R5, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two of the substituents R3 to R7 may be fully substituted by halogens, in particular —F and/or —Cl, and one or more of the substituents R3 to R7 may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, —NO2 and where one or two non-adjacent carbon atoms in R3 to R7 which are not in the α-position may be replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen; a thiouronium cation, which conforms to the formula (6) [C(NR3R4)(SR5)(NR6R7)]+  (6),where R3 to R7 each, independently of one another, denote H, where H is excluded for R5, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two of the substituents R3 to R7 may be fully substituted by halogens, in particular —F and/or —Cl, and one or more of the substituents R3 to R7 may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, —NO2 and where one or two non-adjacent carbon atoms in R3 to R7 which are not in the α-position may be replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen; a guanidinium cation, which conforms to the formula (7) [C(NR8R9)(NR10R11)(NR12R13)]+  (7),where R8 to R13 each, independently of one another, denote H, —CN, N(R′)2, —OR′, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two of the substituents R8 to R13 may be fully substituted by halogens, in particular —F and/or —Cl, and one or more of the substituents R8 to R13 may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, —NO2 and where one or two non-adjacent carbon atoms in R8 to R13 which are not in the α-position may be replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—, where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen; a heterocyclic cation which conforms to the formula (8) [HetN]z+  (8)where HetNz+ denotes a heterocyclic cation selected from the groupwhere the substituents R1′ to R4′ each, independently of one another, denote H, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, and R2′ denote additionally F, Cl, Br, I, —CN, —OR′, —N(R′)2, —P(O)(R′)2, —P(O)(OR′)2, —P(O)(N(R′)2)2, —C(O)R′, —C(O)OR′, —C(O)X, —C(O)N(R′)2, —SO2N(R′)2, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′ and/or NO2, with the proviso that R1′, R3′, R4′ are in this case independently of each other H and/or a straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, where one to three substituents R1′ to R4′ may be fully substituted by halogens, in particular —F and/or —Cl, and one or more substituents R1′ to R4′ may be partially substituted by halogens, in particular —F and/or —Cl, and/or by —OH, —OR′, N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, —NO2, but where R1′ and R4′ cannot simultaneously be fully substituted by halogens and where, in the substituents R1′ to R4′, one or two non-adjacent carbon atoms which are not bonded to the heteroatom may be replaced by atoms and/or atom groups selected from the —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—, where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen or a iodonium cation which conforms to the formula (9)where the aryl group Ar denotes each independently of each other aryl with 6 to 30 C atoms which is non-substituted or substituted with at least a straight-chain or branched alkyl group having 1 to 20 C atoms, a straight-chain or branched alkenyl group having 2 to 20 C atoms and one or more double bonds, a straight-chain or branched alkynyl group having 2 to 20 C atoms and one or more triple bonds, R1*, NO2, SR′, N(R′)2, CN and/or halogen and where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and where R1* each independently is non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl and halogen is F, Cl, Br or I,with the proviso that potassium(18-crone-6)tricyano-n-octylborate and tetraethylammonium phenyl-tricyanoborate are excluded.
地址 Duisburg DE