Compounds containing hydrido-tricyano-borate anions

Patent metadata

Field	Value
Publication number	US-9518068-B2
Application number	US-201214119893-A
Country	US
Kind code	B2
Filing date	May 23, 2012
Priority date	May 31, 2011
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The present invention relates to compounds containing hydrido-tricyano-borate anions, their preparation and their use, in particular as part of electrolyte formulations for electrochemical or optoelectronic devices.

First claim

The invention claimed is:

1. Compounds of formula I
[Kt] z+ z [BH(CN) 3 ] −   I

in which [Kt] z+ denotes an inorganic or organic cation and z is 1, 2, 3 or 4, where sodium hydrido-tricyano-borate, potassium hydrido-tricyano-borate, silver hydrido-tricyano-borate and PPN[HB(CN) 3 ] are excluded.

2. A compound according to claim 1 , wherein [Kt] z+ is an organic cation selected from the group comprising iodonium, tritylium, sulfonium, oxonium, ammonium, phosphonium, uronium, thiouronium, guanidinium cations or heterocyclic cations.

3. A compound according to claim 1 , in which Kt z+ denotes
an inorganic cation selected from the group of H + , NO + , Li + , Mg 2+ , Cu + , Cu 2+ , Zn 2+ , Ca 2+ , Y +3 , Yb +3 , La +3 , Sc +3 , Ce +3 , Nd +3 , Tb +3 , Sm +3 and complex (ligands containing) metal cations
an organic cation, which is a tritylium cation, in which the phenyl groups are optionally 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)
[(R o ) 3 O] +   (1)

[(R o ) 3 S] +   (2),

where
R o 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 R 1* , OR′, N(R′) 2 , CN or halogen and in case of sulfonium cations of formula (2) additionally denotes each independently (R′″) 2 N,
R′ is independently of each other H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C 1 - to C 18 -alkyl, saturated C 3 - to C 7 -cycloalkyl, non-substituted or substituted phenyl,
R 1* is independently of each other non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C 1 - to C 18 -alkyl, saturated C 3 - to C 7 -cycloalkyl, non-substituted or substituted phenyl and
R′″ is independently of each other straight-chain or branched C 1 to C 6 alkyl;
an ammonium cation of formula (3)
[NR 4 ] +   (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 is optionally substituted by straight-chain or branched alkyl groups having 1-6 C atoms,
where one or two R may be fully substituted by halogens, and one or more of R are optionally partially substituted by halogens, and/or by —OH, —OR′, —CN, —N(R′) 2 , —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′) 2 , —SO 2 N(R′) 2 , —C(O)X, —SO 2 OH, —SO 2 X, —NO 2 , —SR′, —S(O)R′, and/or —SO 2 R′ and where one or two non-adjacent carbon atoms in R which are not in the α-position are optionally replaced by atoms and/or atom groups selected from the group consisting of —O—, —S—, —S(O)—, —SO 2 —, —SO 2 O—, —C(O)—, —C(O)O—, —N + (R′) 2 —, —P(O)R′O—, —C(O)NR′—, —SO 2 NR′—, —OP(O)R′O—, —P(O)(N(R′) 2 )NR′—, —P(R′) 2 ═N— and —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C 1 - to C 18 -alkyl, saturated C 3 - to C 7 -cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen;
a phosphonium cation of formula (4)
[P(R 2 ) 4 ] +   (4),

where
R 2 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 is optionally substituted by straight-chain or branched alkyl groups having 1-6 C atoms,
where one or two R 2 are optionally fully substituted by halogens, and one or more of R 2 are optionally partially substituted by halogens, in particular and/or by —OH, —OR′, —CN, —N(R′) 2 , —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′) 2 , —SO 2 N(R′) 2 , —C(O)X, —SO 2 OH, —SO 2 X, —NO 2 , —SR′, —S(O)R′, —SO 2 R′ and where one or two non-adjacent carbon atoms in R 2 which are not in the α-position may be replaced by atoms and/or atom groups selected from the group consisting of —O—, —S—, —S(O)—, —SO 2 —, —SO 2 O—, —C(O)—, —C(O)O—, —N + (R′) 2 —, —P(O)R′O—, —C(O)NR′—, —SO 2 NR′—, —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 C 1 - to C 18 -alkyl, saturated C 3 - to C 7 -cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen;
a uronium cation of formula (5)
[C(NR 3 R 4 )(OR 5 )(NR 6 R 7 )] +   (5),

where
R 3 to R 7 each, independently of one another, denote
H, where H is excluded for R 5 ,
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 is optionally substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two of the substituents R 3 to R 7 are optionally fully substituted by halogens, and one or more of R 3 to R 7 are optionally partially substituted by halogens, and/or by —OH, —OR′, —N(R′) 2 , —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′) 2 , —SO 2 N(R′) 2 , —C(O)X, —SO 2 OH, —SO 2 X, —SR′, —S(O)R′, —SO 2 R′, and/or —NO 2 and where one or two non-adjacent carbon atoms in R 3 to R 7 which are not in the α-position are optionally replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO 2 —, —SO 2 O—, —C(O)—, —C(O)O—, —N + (R′) 2 —, —P(O)R′O—, —C(O)NR′—, —SO 2 NR′—, —OP(O)R′O—, —P(O)(N(R′) 2 )NR′—, —P(R′) 2 ═N— and —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C 1 - to C 18 -alkyl, saturated C 3 - to C 7 -cycloalkyl, non-substituted or substituted phenyl and X each independently is halogen;
a thiouronium cation of formula (6)
[C(NR 3 R 4 )(SR 5 )(NR 6 R 7 )] +   (6),

where
R 3 to R 7 each, independently of one another, denote
H, where H is excluded for R 5 ,
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 is optionally substituted by straight-chain or branched alkyl groups having 1-6 C atoms, where one or two of R 3 to R 7 are optionally fully substituted by halogens, and one or more of the substituents R 3 to R 7 are optionally partially substituted by halogens, and/or by —OH, —OR′, —N(R′) 2 , —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′) 2 , —SO 2 N(R′) 2 , —C(O)X, —SO 2 OH, —SO 2 X, —SR′, —S(O)R′, —SO 2 R′, and/or —NO 2 and where one or two non-adjacent carbon atoms in R 3 to R 7 which are not in the α-position are optionally replaced by atoms and/or atom groups selected from the group —O—, —S—, —S(O)—, —SO 2 —, —SO 2 O—, —C(O)—, —C(O)O—, —N + (R′) 2 —, —P(O)R′O—, —C(O)NR′—, —SO 2 NR′—, —OP(O)R′O—, —P(O)(N(R′) 2 )NR′—, —P(R′) 2 ═N— and —P(O)R′— where R′ each independently is H, non-fluorinated, partially fluorinated or perfl

Assignees

• Ignatyev Nikolai (Mykola)
• Schulte Michael
• Kawata Kentaro
• Goto Tomohisa
• Bernhardt Eduard
• Bernhardt-Pitchougina Vera
• Willner Helge
• Merck Patent Gmbh

Inventors

• Ignatyev Nikolai (Mykola)
• Schulte Michael
• Kawata Kentaro
• Goto Tomohisa
• Bernhardt Eduard
• Bernhardt-Pitchougina Vera
• Willner Helge

Classifications

• C07F5/027

  Organoboranes and organoborohydrides · CPC title

• C07F5/022

  without C-boron linkages · CPC title

• C07F5/006

  Chemistry & Metallurgy · mapped topic

• H01M10/0563

  Liquid materials, e.g. for Li-SOCl2 cells · CPC title

• C07F5/025 Primary

  Boronic and borinic acid compounds · CPC title