DE102009049696A1 - New hole conductor material containing compounds useful e.g. as semiconductor material, preferably p-semiconductor in a solar cell, preferably dye photovoltaic cell, ionic liquid, solvent for chemical reaction and heat carriers - Google Patents

Abstract

Hole conductor material containing compounds (Q) are new. Hole conductor material containing compounds (Q) of formula ((IL) n-Linker-(HTM) n) (I), ((IL-Linker) p-HTM) (II) or (IL-(Linker-HTM) p) (III) are new. IL : a salt group having at least a cation and at least an anion, where at least one of the ion is organic, in (I) and (II) the salt group has binding site to the linker group, and in (III), the salt group q has a binding site to the left group of the linker group; n, m : at least 1; p, q : at least 2; linker : a chemical bond or (n+m) valent 1-50C-organic residue (in case of (I)), or a chemical bond or 1-50C-bivalent residue (in case of (II) and (III)); and HTM : hole conductor material (p-semiconductor) containing group.

Description

The The present invention relates to compounds containing at least one as a hole conductor material (p-type semiconductor) capable group and at least one salt group having at least one cation and at least having an anion, wherein at least one of the ions is organic and their use, especially as ionic liquids and in solar cells.

Ionic liquids are understood as meaning compounds which are completely composed of ions and which have low melting points, in particular of 100 ° C. or below. The remarkable properties of many ionic liquids include their extremely low vapor pressure and high thermal stability. Ionic liquids, which are already in a liquid state at room temperature, are used, for example, by KN Marsh et al., Fluid Phase Equilibria 219 (2004), 93-98 and JG Huddleston et al., Green Chemistry 2001, 3, 156-164 described.

It has now surprisingly been found that compounds, As defined above, is particularly advantageous as ionic Liquids are suitable. They are especially suitable as hole conductor materials for dye-sensitized solar cells.

worin
n für eine ganze Zahl von wenigstens 1 steht,
m für eine ganze Zahl von wenigstens 1 steht,
p für eine ganze Zahl von wenigstens 2 steht,
q für eine ganze Zahl von wenigstens 2 steht,
IL für eine Salzgruppe steht, die wenigstens ein Kation und wenigstens ein Anion aufweist, wobei wenigstens eines der Ionen organisch ist, und wobei
in den Verbindungen der Formeln (I) und (II) die Salzgruppen IL jeweils gleiche oder verschiedene Bedeutungen aufweisen können und jeweils eine Bindungsstelle zu der Linkergruppe aufweisen,
in den Verbindungen der Formel (III) die Salzgruppe IL q Bindungsstellen zu je einer der Linkergruppe aufweist,
Linker in den Verbindungen der Formel (I) für eine chemische Bindung oder einen (n + m)valenten organischen Rest steht, der vorzugsweise 1 bis 50 C-Atome aufweist und in den Verbindungen der Formeln (II) und (III) für eine chemische Bindung oder einen bivalenten organischen Rest steht, der vorzugsweise 1 bis 50 C-Atome aufweist,
HTM für eine als Lochleitermaterial (p-Halbleiter) befähigte Gruppe steht.A first subject of the invention is therefore an ionic liquid of the general formulas (I), (II) or (III)

wherein
n is an integer of at least 1,
m is an integer of at least 1,
p is an integer of at least 2,
q is an integer of at least 2,
IL is a salt group having at least one cation and at least one anion, wherein at least one of the ions is organic, and wherein
in the compounds of the formulas (I) and (II) the salt groups IL may each have identical or different meanings and in each case have a binding site to the linker group,
in the compounds of the formula (III) the salt group IL q has binding sites to one of the linker groups,
Linker in the compounds of the formula (I) is a chemical bond or an (n + m) valent organic radical which preferably has 1 to 50 C atoms and in the compounds of the formulas (II) and (III) for a chemical Bond or a divalent organic radical which preferably has 1 to 50 C atoms,
HTM stands for a group capable of hole conductor material (p-type semiconductor).

One Another object of the invention is a solar cell, in particular Dye solar cell containing at least one ionic liquid of the general formulas (I), (II) or (III).

One Another object of the invention is the use of at least an ionic liquid of the general formulas (I), (II) or (III) as a semiconductor material, preferably as a p-type semiconductor, in particular as p-type semiconductor in solar cells.

One Another object of the invention is the use of at least an ionic liquid of the general formulas (I), (II) or (III) as a solvent for chemical reactions, as an aid in the separation of mixtures, as auxiliaries for extractive rectification for the separation of more concentrated or azeotropic mixtures, as a heat carrier.

The Compounds according to the invention are preferably in the form of an ionic liquid.

Of the Term "ionic liquid" in the context of the present application, a salt containing at least one has organic cation or anion and that at normal pressure (= 101325 Pa = 1.01325 bar) even at temperatures below 200 ° C is liquid. Preferably, the ionic liquids have a Melting point of less than 180 ° C, more preferably less than 150 ° C, especially less than 100 ° C.

Preferably are used in solar cells ionic liquid of the general Formulas (I), (II) or (III) having a melting point in the range of about 40 to 200 ° C, more preferably from 60 to 180 ° C, especially from 80 to 120 ° C, used. The melting point is chosen so that the salts in the work area the solar cell are solid. For outdoor applications amounts hence the melting point of the ionic liquid of the general Formulas (I), (II) or (III) preferably at least 80 ° C.

In the context of the present invention, the term "alkyl" includes straight-chain or branched alkyl. Preferably it is straight-chain or branched C ₁ -C ₃₀ -alkyl, in particular C ₁ -C ₁₈ -alkyl and very particularly preferably C ₁ -C ₁₂ -alkyl. Examples of alkyl groups are in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 1-methyl-butyl, tert-pentyl, neopentyl, n-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4- Methyl 2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1 butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, n-heptyl, n-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4, 4-trimethyl-pentyl, 1,1,3,3-tetramethylbutyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n- Heptadecyl, n-octadecyl and n-eicosyl.

The term alkyl also includes alkyl radicals whose carbon chain is replaced by one or more nonadjacent heteroatoms or heteroatom-containing groups which are preferably selected from -O-, -S-, -NR ^a -, -PR ^a -, -SiR ^a R ^aa and / or -SO ₂ - can be interrupted. R ^a is preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. R ^aa is preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl or aryl.

Examples of alkyl radicals whose carbon chains may be interrupted by one or two nonadjacent heteroatoms -O- are the following:
Methoxymethyl, diethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, diethoxyethyl, 2-butoxyethyl, 2-octyloxyethyl, 2-methoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 2-isopropoxyethyl, 2-butoxypropyl, 3-butoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-propoxybutyl, 6-methoxyhexyl, 3,6-dioxa-heptyl (5-methoxy-3-oxa-pentyl), 3,6-dioxa-octyl (7-methoxy 4-oxa-heptyl), 4,8-dioxa-nonyl (7-methoxy-4-oxa-heptyl), 3,7-dioxa-octyl, 3,7-dioxa-nonyl, 4,7-dioxa-octyl , 4,7-Dioxanonyl, 2- and 4-butoxybutyl, 4,8-dioxadecyl, 9-ethoxy-5-oxa-nonyl.

Examples of alkyl radicals whose carbon chains may be interrupted by three or more than three nonadjacent heteroatoms -O- are also oligo- and polyoxyalkylenes, ie compounds having repeating units, which are preferably selected from (CH ₂ CH ₂ O) _x1 , (CH (CH ₃ ) CH ₂ O) _x2 and ((CH ₂ ) ₄ O) _x3 , where x1, x2 and x3 independently of one another represent an integer from 3 to 100, preferably from 3 to 80. The sum of x1, x2 and x3 is an integer from 3 to 300, especially 3 to 100. In polyoxyalkylenes having two or three different repeating units, the order is arbitrary, ie it may be random, alternating or block-shaped Repeat units act. Examples of these are 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9-trioxadodecyl, 4,8,12-trioxatridecyl (11-methoxy-4,8-dioxa-undecyl), 4, 8,12-trioxatetradecyl, 14-methoxy-5,10-dioxa-tetradecyl, 5,10,15-trioxaheptadecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 4,8, 12,16-tetraoxaheptadecyl (15-methoxy-4,8,12-trioxapentadecyl), 4,8,12,16-tetraoxa-octadecyl and the like.

Examples of alkyl radicals whose carbon chains by one or more, for. B. 1, 2, 3, 4 or more than 4, non-adjacent heteroatoms -S- may be interrupted, are the following:
Butylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-butylthio-ethyl, 2-dodecylthioethyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3-propylthiopropyl, 3-butylthiopropyl, 4-methylthiobutyl, 4-ethylthiobutyl, 4- Propylthiobutyl, 3,6-dithiaheptyl, 3,6-dithio-octyl, 4,8-dithia-nonyl, 3,7-dithio-octyl, 3,7-di-thia-nonyl, 2- and 4-butylthiobutyl, 4 , 8-dithia-decyl, 3,6,9-trithia-decyl, 3,6,9-trithia-undecyl, 3,6,9-trithia-dodecyl, 3,6,9,12-tetrathia-tridecyl and 3 , 6,9,12-tetrathia tetradecyl.

Examples of alkyl radicals whose carbon chains are interrupted by one or two non-adjacent heteroatom-containing groups -NR ^a - are the following:
2-monomethyl- and 2-monoethylaminoethyl, 2-dimethylaminoethyl, 3-methylaminopropyl, 2- and 3-dimethylaminopropyl, 3-monoisopropylaminopropyl, 2- and 4-monopropylaminobutyl, 2- and 4-dimethylaminobutyl, 6-methylaminohexyl, 6-dimethylaminohexyl, 6-methyl-3,6-diazaheptyl, 3,6-dimethyl-3,6-diazaheptyl, 3,6-diazaoctyl and 3,6-dimethyl-3,6-diazaoctyl.

Examples of alkyl radicals whose carbon chains may be interrupted by three or more than three non-adjacent heteroatom-containing groups -NR ^a - are also oligo- and polyalkyleneimines. The statements made above for the polyoxyalkylenes apply analogously to polyalkyleneimines, wherein the oxygen atom is replaced in each case by a group NR ^a , in which R ^{a is} preferably hydrogen or C ₁ -C ₄ -alkyl. Examples of these are 9-methyl-3,6,9-triazadecyl, 3,6,9-trimethyl-3,6,9-triazadecyl, 3,6,9-triazaundecyl, 3,6,9-trimethyl-3,6 , 9-triazaundecyl, 12-methyl-3,6,9,12-tetraazatridecyl, 3,6,9,12-tetramethyl-3,6,9,12-tetraazatridecyl, and the like.

Examples of alkyl radicals whose carbon chains by one or more, for. B. 1 or 2 non-adjacent groups -SO ₂ - are interrupted, are 2-methylsulfonylethyl, 2-ethylsulfonylethyl, 2-propylsulfonylethyl, 2-Isopropylsulfonylethyl, 2-Butylsulfonylethyl, 2-methylsulfonylpropyl, 3-methylsulfonylpropyl, 2-Ethylsulfonylpropyl, 3- Ethylsulfonylpropyl, 2-propylsulfonylpropyl, 3-propylsulfonylpropyl, 2-butylsulfonylpropyl, 3-butylsulfonylpropyl, 2-methylsulfonylbutyl, 4-methylsulfonylbutyl, 2-ethylsulfonylbutyl, 4-ethylsulfonylbutyl, 2-propylsulfonylbutyl, 4-propylsulfonylbutyl and 4-butylsulfonylbutyl.

The term alkyl also includes substituted alkyl radicals. Substituted alkyl groups may have one or more (eg 1, 2, 3, 4, 5 or more than 5) substituents depending on the length of the alkyl chain. These are preferably selected independently from among cycloalkyl, cycloalkyloxy, polycyclyl, polycycloxy, heterocycloalkyl, aryl, aryloxy, arylthio, hetaryl, halogen, hydroxy, SH, = O, = S, = NR ^a , COOH, carboxylate, SO ₃ H, sulfonate , NE ¹ E ² , nitro and cyano, wherein E ¹ and E ^{2 are} independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. Cycloalkyl, cycloalkyloxy, polycycloalkyl, polycycloalkyloxy, heterocycloalkyl, aryl and hetaryl substituents of the alkyl groups may themselves be unsubstituted or substituted; suitable substituents are those mentioned below for these groups.

The The above statements on alkyl also apply in principle for the alkyl moieties in alkoxy, alkylamino, dialkylamino, Alkylthio (alkylsulfanyl), alkylsulfinyl, alkylsulfonyl, etc.

Suitable substituted alkyl radicals are the following:
Alkyl substituted by carboxy, such as. Carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl, 7-carboxyheptyl, 8-carboxyctyl, 9-carboxynonyl, 10-carboxydecyl, 12-carboxydodecyl and 14-carboxytetradecyl;
Alkyl which is substituted by SO ₃ H, such as. Sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, 5-sulfopentyl, 6-sulfohexyl, 7-sulfoheptyl, 8-sulfooctyl, 9-sulfononyl, 10-sulfodecyl, 12-sulfododecyl and 14-sulfotetradecyl;
Alkyl which is substituted by carboxylate, such as. For alkoxycarbonylalkyl, e.g. Methoxycarbonylmethyl, ethoxycarbonylmethyl, n-butoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-methoxycarbonylpropyl, 2-ethoxycarbonylpropyl, 2- (n-butoxycarbonyl) propyl, 2- (4-n-butoxycarbonyl) propyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 3- (n-butoxycarbonyl) propyl, 3- (4-n-butoxycarbonyl) propyl, aminocarbonylalkyl, e.g. Aminocarbonylmethyl, aminocarbonylethyl, aminocarbonylpropyl and the like, alkylaminocarbonylalkyl such as methylaminocarbonylmethyl, methylaminocarbonylethyl, ethylcarbonylmethyl, ethylcarbonylethyl and the like, or dialkylaminocarbonylalkyl such as dimethylaminocarbonylmethyl, dimethylaminocarbonylethyl, dimethylcarbonylpropyl, diethylaminocarbonylmethyl, diethylaminocarbonylethyl, diethylcarbonylpropyl and the like.

alkyl, which is substituted by hydroxy, such as. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl, 4-hydroxybutyl, 2-hydroxy-2,2-dimethylethyl, 5-hydroxy-3-oxa-pentyl, 6-hydroxyhexyl, 7-hydroxy-4-oxa-heptyl, 8-hydroxy-4-oxo-octyl, 8-hydroxy-3,6-dioxo-octyl, 9-hydroxy-5-oxa-nonyl, 11-hydroxy-4,8-dioxaundecyl, 11-hydroxy-3,6,9-trioxa-undecyl, 14-hydroxy-5,10-dioxa-tetradecyl, 15-hydroxy-4,8,12-trioxa-pentadecyl and the like.

alkyl, which is substituted by amino, such as. 2-aminoethyl, 2-aminopropyl, 3-aminopropyl, 4-aminobutyl, 6-aminohexyl and the like.

Alkyl which is substituted by cyano, such as. 2-cyanoethyl, 3-cyanopropyl, 3-cyanobutyl and 4-cyanobutyl;
Alkyl, which is substituted by halogen, as defined below, wherein in the alkyl group, the hydrogen atoms may be partially or completely replaced by halogen atoms, such as C ₁ -C ₁₈ fluoroalkyl, z. Trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, and the like, C ₁ -C ₁₈ -chloroalkyl, e.g. Chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2- and 3-chloropropyl, 2-, 3- and 4-chlorobutyl, 1,1-dimethyl-2-chloroethyl and the like, C ₁ -C ₁₈ -bromoalkyl, e.g. , Bromoethyl, 2-bromoethyl, 2- and 3-bromopropyl and 2-, 3- and 4-bromobutyl and the like

alkyl, which is substituted by nitro, such as. For example, 2-nitroethyl, 2- and 3-nitropropyl and 2-, 3- and 4-nitrobutyl and the like.

alkyl, which is substituted by cycloalkyl, such as. Cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the like.

alkyl, which is substituted by = O (oxo group), such as. B. 2-oxopropyl, 2-oxobutyl, 3-oxobutyl, 1-methyl-2-oxopropyl, 2-oxopentyl, 3-oxopentyl, 1-methyl-2-oxobutyl, 1-methyl-3-oxobutyl, 2-oxohexyl, 3-oxohexyl, 4-oxohexyl, 2-oxoheptyl, 3-oxoheptyl, 4-oxoheptyl, 4-oxoheptyl and like.

alkyl, which is substituted by = S (thioxo), such as. For example, 2-thioxopropyl, 2-thioxobutyl, 3-thioxobutyl, 1-methyl-2-thioxopropyl, 2-thioxopentyl, 3-thioxopentyl, 1-methyl-2-thioxobutyl, 1-methyl-3-thioxobutyl, 2-thioxohexyl, 3-thioxohexyl, 4-thioxohexyl, 2-thioxoheptyl, 3-thioxoheptyl, 4-thioxoheptyl, 4-thioxoheptyl and the like.

Alkyl which is substituted by = NR ^a -, preferably those in which R ^{a is} hydrogen or C ₁ -C ₄ alkyl, such as. 2-iminopropyl, 2-iminobutyl, 3-iminobutyl, 1-methyl-2-iminopropyl, 2-iminopentyl, 3-iminopentyl, 1-methyl-2-iminobutyl, 1-methyl-3-imino-butyl, 2- Iminohexyl, 3-iminohexyl, 4-iminohexyl, 2-iminoheptyl, 3-iminoheptyl, 4-iminoheptyl, 4-iminoheptyl, 2-methyliminopropyl, 2-methyliminobutyl, 3-methyliminobutyl, 1-methyl-2-methyliminopropyl, 2-methyliminopentyl, 3-methyliminopentyl, 1-methyl-2-methyliminobutyl, 1-methyl-3-methyliminobutyl, 2-methyliminohexyl, 3-methyliminohexyl, 4-methyliminohexyl, 2-methyliminoheptyl, 3-methyliminoheptyl, 4-methyliminoheptyl, 4-methyliminoheptyl, 2- Ethyliminopropyl, 2-ethyliminobutyl, 3-ethyliminobutyl, 1-methyl-2-ethyliminopropyl, 2-ethyliminopentyl, 3-ethyliminopentyl, 1-methyl-2-ethyliminobutyl, 1-methyl-3-ethyliminobutyl, 2-ethyliminohexyl, 3-ethyliminohexyl, 4-ethyliminohexyl, 2-ethyliminoheptyl, 3-ethyliminoheptyl, 4-ethyliminoheptyl, 4-ethyliminoheptyl, 2-propyliminopropyl, 2-propyliminobutyl, 3-propyliminobutyl, 1-methyl-2-propyliminopropyl, 2-Pro pyliminopentyl, 3-propyliminopentyl, 1-methyl-2-propyliminobutyl, 1-methyl-3-propyliminobutyl, 2-propyliminohexyl, 3-propyliminohexyl, 4-propyliminohexyl, 2-propyliminoheptyl, 3-propyliminoheptyl, 4-propyliminoheptyl, 4-propyliminoheptyl, and the like like.

Alkoxy is an alkyl group bonded via an oxygen atom. Examples of alkoxy are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 , 1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy , 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -Ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy, hexoxy and R ^A O- (CH ₂ CH ₂ CH ₂ CH ₂ O) _n -CH ₂ CH ₂ CH ₂ CH ₂ O- with R ^{A is} hydrogen or C C ₁ -C ₄ -alkyl, preferably hydrogen, methyl or ethyl and n is 0 to 10, preferably 0 to 3.

alkylthio (Alkylsulfanyl) represents a via a sulfur atom bound alkyl group. Examples of alkylthio are methylthio, Ethylthio, propylthio, butylthio, pentylthio and hexylthio.

alkylsulfinyl for an alkyl group bonded via an S (= O) group.

Alkylsulfinyl is an alkyl group bonded via an S (= O) ₂ group.

Aryl substituted alkyl ("arylalkyl") groups have at least one unsubstituted or substituted aryl group as defined below. Suitable substituents on the aryl group are the following. In this case, the alkyl group in "arylalkyl" at least one further substituent, as defined above, and / or by one or more non-adjacent heteroatoms or heteroatom-containing groups selected from -O-, -S-, -NR ^a -, and / or -SO ₂ - be interrupted. Arylalkyl is preferably phenyl-C ₁ -C ₁₀ -alkyl, more preferably phenyl-C ₁ -C ₄ -alkyl, z. For benzyl, 1-phenethyl, 2-phenethyl, 1-phenprop-1-yl, 2-phenprop-1-yl, 3-phenprop-1-yl, 1-phenbut-1-yl, 2-phenbut-1 -yl, 3-phenbut-1-yl, 4-phenbut-1-yl, 1-phenbut-2-yl, 2-phenbut-2-yl, 3-phenbut-2-yl, 4-phenbut-2-yl , 1- (phen-meth) -eth-1-yl, 1- (phen-methyl) -1- (methyl) -eth-1-yl or - (phen-methyl) -1- (methyl) -prop-1-yl; preferably for benzyl and 2-phenethyl.

The term "alkenyl" in the context of the present invention comprises straight-chain and branched alkenyl groups which, depending on the chain length, may carry one or more double bonds (eg 1, 2, 3, 4 or more than 4). Preference is given to C ₂ -C ₁₈ -, more preferably C ₂ -C ₁₂ alkenyl groups. The term "alkenyl" also includes substituted alkenyl groups which may carry one or more (eg, 1, 2, 3, 4, 5 or more than 5) substituents. Suitable substituents are, for. B. selected from = O, = S, = NR ^a , cycloalkyl, cycloalkyloxy, polycyclyl, polycycloxy, heterocycloalkyl, aryl, aryloxy, arylthio, hetaryl, halogen, hydroxy, SH, COOH, carboxylate, SO ₃ H, sulfonate, alkylsulfinyl, Alkylsulfonyl, NE ³ E ⁴ , nitro and cyano, wherein E ³ and E ^{4 are} independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl.

The term "alkenyl" also includes alkenyl radicals whose carbon chain may be interrupted by one or more non-adjacent heteroatoms or heteroatom-containing groups, which are preferably selected from -O-, -S-, -NR ^a - and / or -SO ₂ - ,

alkenyl then stands, for example, ethenyl (vinyl), 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, hexa-1,4-dien-3-yl, Hexa-1,4-dien-6-yl, hexa-1,5-dien-1-yl, hexa-1,5-dien-3-yl, hexa-1,5-dien-4-yl, Hepta-1,4-dien-1-yl, hepta-1,4-dien-3-yl, hepta-1,4-dien-6-yl, hepta-1,4-dien-7-yl, Hepta-1,5-dien-1-yl, hepta-1,5-dien-3-yl, hepta-1,5-dien-4-yl, hepta-1,5-dien-7-yl, Hepta-1,6-dien-1-yl, hepta-1,6-dien-3-yl, hepta-1,6-dien-4-yl, hepta-1,6-dien-5-yl, Hepta-1,6-dien-2-yl, octa-1,4-dien-1-yl, octa-1,4-dien-2-yl, octa-1,4-dien-3-yl, Octa-1,4-dien-6-yl, octa-1,4-dien-7-yl, octa-1,5-dien-1-yl, octa-1,5-dien-3-yl, Octa-1,5-dien-4-yl, octa-1,5-dien-7-yl, octa-1,6-dien-1-yl, octa-1,6-dien-3-yl, Octa-1,6-dien-4-yl, octa-1,6-dien-5-yl, octa-1,6-dien-2-yl, deca-1,4-dienyl, Deca-1,5-dienyl, deca-1,6-dienyl, deca-1,7-dienyl, deca-1,8-dienyl, Deca-2,5-dienyl, deca-2,6-dienyl, deca-2,7-dienyl, deca-2,8-dienyl and the same.

The term "cycloalkyl" in the context of the present invention comprises unsubstituted as well as substituted monocyclic saturated hydrocarbon groups having generally 3 to 12 carbon ring members (C ₃ -C ₁₂ -cycloalkyl groups) such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl , Cycloundecyl or cyclododecyl, in particular C ₅ -C ₁₂ -cycloalkyl. Suitable sub stituents are usually selected under for alkyl, the substituents mentioned above for the alkyl groups, alkoxy and alkylthio. Substituted cycloalkyl groups may have one or more (eg 1, 2, 3, 4, 5 or more than 5) substituents, wherein in the case of halogen, the cycloalkyl radical is partially or completely substituted by halogen.

Examples of cycloalkyl groups are cyclopentyl, 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclopentyl, chloropentyl, dichloropentyl, dimethylcyclopentyl, cyclohexyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 3 and 4-propylcyclohexyl, 3- and 4-isopropylcyclohexyl, 3- and 4-butylcyclohexyl, 3- and 4-sec-butylcyclohexyl, 3- and 4-tert-butylcyclohexyl, chlorhexyl, dimethylcyclohexyl, diethylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl , Butoxycyclohexyl, methylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, cycloheptyl, 2-, 3- and 4-methylcycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 3- and 4-propylcycloheptyl, 3- and 4-isopropylcycloheptyl, 3- and 4- Butylcycloheptyl, 3- and 4-sec-butylcycloheptyl, 3- and 4-tert-butylcycloheptyl, cyclooctyl, 2-, 3-, 4- and 5-methylcyclooctyl, 2-, 3-, 4- and 5-ethylcyclooctyl, 3-, 4- and 5-propylcyclooctyl, partially fluorinated cycloalkyl and perfluorinated cycloalkyl of the formula C _n F _{2 ( n ) - (1-b)} H _2a-b mi t n = 5 to 12, 0 <= a <= n and b = 0 or 1.

cycloalkyloxy is an oxygen-bonded cycloalkyl group, as defined above.

Of the Expression "cycloalkenyl" includes unsubstituted and substituted mono- or diunsaturated hydrocarbon groups with 3 to 5, to 8, to 12, preferably 5 to 12 carbon ring members, such as cyclopent-1-en-1-yl, cyclopent-2-en-1-yl, cyclopent-3-en-1-yl, Cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl, cyclohexa-2,5-dien-1-yl and the same. Suitable substituents are those previously for Cycloalkyl mentioned.

cycloalkenyloxy represents an oxygen-bonded cycloalkenyl group, as defined above.

Of the Term "polycyclyl" as used herein Invention in the broadest sense compounds that have at least two rings regardless of how these rings are linked are. These may be carbocyclic and / or heterocyclic Trade rings. The rings can be saturated or be unsaturated. The rings can over Single or double bond linked ("polynuclear Compounds "), connected by annealing (" condensed Ring systems ") or bridges (" bridged over Ring systems "," cage connections ") be. Preferred polycyclic compounds are bridged Ring systems and fused ring systems. Condensed ring systems may be linked by annulation (condensed) be aromatic, hydroaromatic and cyclic compounds. condensed Ring systems consist of two, three or more than three rings. ever according to the type of linkage, a distinction is made in condensed Ring systems between an ortho-annulation, d. H. every ring has one edge or two atoms in common with each neighboring ring, and a peri-annulation in which one carbon atom more than belongs to two rings. Preferred among the condensed Ring systems are ortho-fused ring systems. To the bridged ring systems count in the context of the present invention, those not to the polynuclear ring systems and not to the condensed ones Ring systems count and where at least two ring atoms belong to at least two different rings. At the bridged Ring systems are distinguished according to the number of ring-opening reactions, which are formally required to become an open-chain connection to arrive, bi, tri-, tetracyclo compounds, etc., consisting of two, three, four, etc. rings exist. The term "bicycloalkyl" includes while bicyclic hydrocarbon radicals having preferably 5 to 10 C atoms such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, Bicyclo [2.2.1] hept-7-yl, bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, Bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl and the like. The term "bicycloalkenyl" includes monounsaturated, bicyclic hydrocarbon radicals preferably having 5 to 10 C atoms, such as bicyclo [2.2.1] hept-2-en-1-yl.

The term "aryl" in the context of the present invention comprises mononuclear or polynuclear aromatic hydrocarbon radicals which may be unsubstituted or substituted. Aryl is usually for hydrocarbon radicals having 6 to 10, to 14, to 18, preferably 6 to 10 carbon ring members. Aryl is preferably unsubstituted or substituted phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, etc., and more preferably phenyl or naphthyl. Substituted aryls may have one or more (eg 1, 2, 3, 4, 5 or more than 5) substituents depending on the number and size of their ring systems. These are preferably selected independently from among alkyl, alkoxy, cycloalkyl, cycloalkyloxy, heterocycloalkyl, aryl, aryloxy, arylthio, hetaryl, halogen, hydroxy, SH, alkylthio, alkylsulfinyl, alkylsulfonyl, COOH, carboxylate, SO ₃ H, sulfonate, NE ⁵ E ⁶ , nitro and cyano, wherein E ⁵ and E ⁶ independently of one another represent hydrogen, alkyl, cycloalkyl, cycloalkyloxy, polycyclylyl, polycycloxy, heterocycloalkyl, aryl, aryloxy or hetaryl. Aryl is particularly preferably phenyl, which in the case of a substitution can generally carry 1, 2, 3, 4 or 5, preferably 1, 2 or 3, substituents.

Aryl which carries one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl , 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3 , 5- and 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 2-, 3- and 4-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dibutylphenyl, 2 , 4,6-tributylphenyl, 2-, 3- and 4-isobutylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisobutylphenyl, 2,4,6-triisobutylphenyl, 2-, 3 and 4-sec-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-sec-butylphenyl, 2,4,6-tri-sec-butylphenyl, 2-, 3- and 4-tert-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-tert-butylphenyl, 2,4,6-tri-tert-butylphenyl and 2-, 3-, 4-dodecylphenyl; 2-, 3- and 4-methoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-, 3- and 4-ethoxyphenyl, 2 , 4-, 2,5-, 3,5- and 2,6-diethoxyphenyl, 2,4,6-triethoxyphenyl, 2-, 3- and 4-propoxyphenyl, 2,4-, 2,5-, 3, 5- and 2,6-dipropoxyphenyl, 2-, 3- and 4-isopropoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropoxyphenyl, 2-, 3- and 4-butoxyphenyl, 2-, 3-, 4-hexyloxyphenyl; 2-, 3-, 4-chlorophenyl, 2,4-, 2,5-, 3,5- and 2,6-dichlorophenyl, trichlorophenyl, 2-, 3-, 4-fluorophenyl, 2,4-, 2, 5-, 3,5- and 2,6-difluorophenyl, trifluorophenyl, such as. B. 2,4,6-trifluorophenyl, tetrafluorine orphenyl, pentafluorophenyl, 2-, 3- and 4-cyanophenyl; 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl; 4-dimethylaminophenyl; 4-acetylphenyl; Methoxyethylphenyl, ethoxymethylphenyl; Methylthiophenyl, isopropylthiophenyl or tert-butylthiophenyl; methylnaphthyl; Isopropylnaphthyl or ethoxynaphthyl. Examples of substituted aryl wherein two substituents attached to adjacent carbon atoms of the aryl ring form a fused ring or fused ring system are indenyl and fluorenyl.

Of the Expression "aryloxy" is within the scope of the present invention Invention for bonded via an oxygen atom Aryl.

Of the Term "Arylthio" is within the scope of the present Invention for bonded over a sulfur atom Aryl.

The term "heterocycloalkyl" in the context of the present invention comprises non-aromatic, unsaturated or fully saturated, cycloaliphatic groups having generally 5 to 8 ring atoms, preferably 5 or 6 ring atoms, in which 1, 2 or 3 of the ring carbon atoms by heteroatoms selected from oxygen , Nitrogen, sulfur and a group -NR ^a - are replaced and which is unsubstituted or substituted by one or more, for example 1, 2, 3, 4, 5 or 6, C ₁ -C ₆ alkyl groups. Exemplary of such heterocycloaliphatic groups are Pyrroli dinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, morpholidinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl, tetrahydrothienyl, dihydrothienyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydropyranyl, 1,2 Oxazolin-5-yl, 1,3-oxazolin-2-yl and dioxanyl. Nitrogen-containing heterocycloalkyl can in principle be bound both via a carbon atom and via a nitrogen atom.

The term "heteroaryl (hetaryl)" in the context of the present invention comprises unsubstituted or substituted, heteroaromatic, mononuclear or polynuclear groups having generally 5 to 14 ring atoms, preferably 5 or 6 ring atoms, in which 1, 2 or 3 of the ring carbon atoms one, two, three or four heteroatoms selected from O, N, -NR ^a and S are substituted, such as furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, benzofuranyl, benzthiazolyl, benzimidazolyl, pyridyl, quinolinyl, acridinyl, pyridazinyl , Pyrimidinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, indolyl, purinyl, indazolyl, benzotriazolyl, 1,2,3-triazolyl, 1,3,4-triazolyl and carbazolyl, these heterocycloaromatic groups in the case of a substitution generally 1, 2 or 3 substituents. The substituents are usually selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, hydroxy, carboxy, halogen and cyano.

5 to 7-membered nitrogen-containing heterocycloalkyl or heteroaryl radicals, which optionally contain further heteroatoms are, for example for pyrrolyl, pyrazolyl, imidazolyl, triazolyl, pyrrolidinyl, pyrazolinyl, Pyrazolidinyl, imidazolinyl, imidazolidinyl, pyridinyl, pyridazinyl, Pyrimidinyl, pyrazinyl, triazinyl, piperidinyl, piperazinyl, oxazolyl, Isooxazolyl, thiazolyl, isothiazolyl, indolyl, quinolinyl, isoquinolinyl or quinaldinyl which is unsubstituted or substituted as above can be called.

halogen is fluorine, chlorine, bromine or iodine.

Carboxylate and sulfonate in the context of this invention preferably represent a derivative of a carboxylic acid function or a sulfonic acid function, in particular a metal carboxylate or sulfonate, a carboxylic acid ester or sulfonic acid ester function or a carboxylic acid or sulfonic acid amide function. These include z. As the esters with C ₁ -C ₄ alkanols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol and tert-butanol.

Of the Expression "acyl" is within the meaning of the present Invention for alkanoyl, hetaroyl or aroyl groups with generally 1 to 11, preferably 2 to 8 carbon atoms, for example, the formyl, acetyl, propanoyl, butanoyl, Pentanoyl, hexa-noyl, heptanoyl, 2-ethylhexanoyl, 2-propylheptanoyl, Benzoyl or naphthoyl group.

The radicals E ¹ and E ² , E ³ and E ⁴ , E ⁵ and E ⁶ are independently selected from hydrogen, alkyl, cycloalkyl and aryl. The groups NE ¹ E ² , NE ³ E ⁴ and NE ⁵ E ⁶ are preferably N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-diisopropylamino, N, N-di-n -butylamino, N, N-di-tert-butylamino, N, N-dicyclohexylamino or N, N-diphenylamino.

In the context of the present invention, radicals "having two free valences" are derived formally from the respective parent compound by abstraction of two H atoms. Accordingly, residues "with three free valences "of the respective parent compound formally by abstraction of three H atoms. The free valences may be bound to the same or different atoms. The above applies accordingly for residues with more than three free valences. The term "divalent" or "trivalent" means that the moiety has two or three free valences to form bonds to IL and HTM. In the context of the present invention, therefore, the terms "radical with two free valences" and "bivalent radical" are used synonymously. The above applies analogously to residues with three free valences and the like.

in the Under the present invention is meant a polyvalent Organic residue is an organic residue with two, three, four or more more than four free valence. The organic radical can be straight-chain, branched or cyclic and usually has 1 to 50 atoms between the flanking bonds.

The term "alkylene" in the context of the present invention stands for a linear or branched saturated hydrocarbon chain having 1 to 50, preferably 1 to 30, for. B. linear alkylene having 2 to 30 carbon atoms, and in particular 1 to 10 carbon atoms, for. 1 to 4 carbon atoms, such as ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, hptane 1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1, 13-diyl and tetradecane-1,14-diyl. In the context of the present invention, the terms "alkylene" and "alkanediyl" are used synonymously. The alkanediyl group can simply be up to several times, for. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, phenyl or C ₃ -C ₁₀ cycloalkyl be substituted.

The term "cycloalkanediyl" in the context of the present invention is a cyclic, z. B. a monocyclic, bicylic or tricyclic, saturated hydrocarbon radical having two free valences and 3 to 30 carbon atoms, for. B. a monocyclic saturated hydrocarbon radical having two free valences and 3 to 10 carbon atoms, or a bicyclic, saturated hydrocarbon radical having two free valences and 7 to 30 carbon atoms. The cycloalkanediyl group can be monosubstituted to polyunsaturated, e.g. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

The term "arylene" in the context of the present invention is mono- or polynuclear aromatic hydrocarbon radicals having two free valences. Arylene usually has 6 to 10, to 14, to 18, preferably 6 to 10 carbon ring members. Examples of arylene include phenylene, e.g. For example, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, naphthylene, e.g. For example, 1,8-naphthylene, 1,5-naphthylene or 1,4-naphthylene. The arylene group can be simply up to several times, for. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkoxy.

The term "arylenealkylene" in the context of the present invention stands for an araliphatic radical having 7 to 50 carbon atoms and having two free valences, wherein in arylenealkylene the arylene group, as mentioned above, has a free valency on the ring carbon atom of the arylene group and the alkylene group, as above called, having a free valence on the alkylene group, for. As naphthylene alkyls and more preferably phenylene alkyls. The alkylene group in the arylenealkylene group preferably contains 1 to 12 carbon atoms. The arylene group and / or the alkylene group in arylenealkylene may contain one or more, e.g. One, two, three, four or more than four, bear substituents that are the same or different. Suitable substituents are fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxyl. In a first embodiment, one valence free of the valence on the arylene group forms a covalent bond to HTM and the other free valency on the alkylene group forms a covalent bond to IL. In a second embodiment, the free valency on the arylene group forms a covalent bond to IL and the other free valency on the alkylene group forms a covalent bond to HTM.

The term "cycloalkylene-alkylene" in the context of the present invention is an aliphatic-cycloaliphatic radical having 4 to 50 carbon atoms and having two free valences, wherein the cycloalkylene group as mentioned above, and the Alky lengruppe, as mentioned above, in cycloalkylene in each case have a free valence, z. For example, cyclopentylene-alkylene or cyclohexylene. The alkylene group in the cycloalkylene-alkylene group preferably contains 1 to 12 carbon atoms. The cycloalkylene group and / or the alkylene group in cycloalkylene-alkylene may contain one or more, e.g. One, two, three, four or more than four, bear substituents that are the same or different. Suitable substituents are fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxyl. In a ers In the embodiment, the free valency on the cycloalkylene group forms a covalent bond to HTM and the other free valency on the alkylene group forms a covalent bond to IL. In a second embodiment, the free valence on the cycloalkylene group forms a covalent bond to IL and the other free valence on the alkylene group forms a covalent bond to HTM.

The Salt groups IL can be used according to the invention include one or more cations or anions, wherein the salt groups are electrically neutral to the outside. The connection to a or more linker groups can have at least 1 cation or at least one anion or when connected to more than one linker Cations and anions take place.

Prefers the link to the linker group (s) is via a covalent bond between a cation and the linker group.

Preferably, the group IL is selected from salt groups of the general formula (IV.A) [A ⁺ ] _n [Y] ^n- (IV.A), where n is 1, 2, 3 or 4, [A ⁺ ] is a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and [Y] ^n- for a one-, two- or three-membered cation , tri- or tetravalent anion or mixtures of these anions;
Mixed salt groups of the general formulas (IV.B) [A1 ⁺ ] [A2 ⁺ ] [Y] ^n- (IV.Ba), where n = 2, [A1 ⁺ ] [A2 ⁺ ] [A3] ⁺ [Y] ^n- (IV.Bb), where n = 3, [A1 ⁺ ] [A2 ⁺ ] [A3 ⁺ ] [A4 ⁺ ] [Y] ^n- (IV.Bc), where n = 4, and where [A1 ⁺ ], [A2 ⁺ ], [A3 ⁺ ] and [A4 ⁺ ] are independently selected from the groups mentioned for [A ⁺ ] and [Y] ^{n- has} the meaning given under formula (IV.A) ; or
mixed salt groups of the general formulas (IV.C) [A1 ⁺ ] [A2 ⁺ ] [A3 ⁺ ] [M1 ⁺ ] [Y] ^n- (IV.Ca), where n = 4, [A1 ⁺ ] [A2 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] [Y] ^n- (IV.Cb), where n = 4, [A1 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] [M3 ⁺ ] [Y] ^n- (IV.Cc), where n = 4, [A1 ⁺ ] [A2 ⁺ ] [M1 ⁺ ] [Y] ^n- (IV.Cd), where n = 3, [A1 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] Y] ^n- (IV.Ce), where n = 3, [A1 ⁺ ] [M1 ⁺ ] [Y] ^n- (IV.Cf), where n = 2, [A1 ⁺ ] [A2 ⁺ ] [M4 ²⁺ ] [Y] ^n- (IV.Cg), where n = 4, [A1 ⁺ ] [M1 ⁺ ] [M4 ²⁺ ] [Y] ^n- (IV.Ch), where n = 4, [A1 ⁺ ] [M5 ³⁺ ] [Y] ^n- (IV.Ci), where n = 4, [A1 ⁺ ] ⁺ [M4 ²⁺ ] [Y] ^n- (IV.Cj), where n = 3, and where [A1 ⁺ ], [A2 ⁺ ] and [A3 ⁺ ] are selected, independently of one another, from the groups mentioned for [A ⁺ ], [Y] ^{n- has} the meaning given under formula (IV.A) and [M1 ⁺ ] , [M2 ⁺ ], [M3 ⁺ ] monovalent metal cations, [M4 ²⁺ ] divalent metal cations and [M5 ³⁺ ] trivalent metal cations.

Prefers are salts of groups IV.A and IV.B, more preferably of the group IV.A.

The metal cations [M1 ⁺ ], [M2 ⁺ ] [M3 ⁺ ], [M4 ²⁺ ] and [M5 ³ ] ⁺ mentioned in the formulas (IV.Ca) to (IV.Cj) are generally metal cations the 1st, 2nd, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th and 14th Grup pe of the periodic table. Suitable metal cations are, for example, Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , Cr ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ^{2 +} , Ag ⁺ , Zn ²⁺ and Al ³⁺ .

Suitable compounds which are suitable for forming the cation [A ⁺ ] of ionic liquids are, for. B. in the DE 102 02 838 A1 described. These compounds preferably contain at least one heteroatom, such as. B. 1 to 10 heteroatoms, which are preferably selected from nitrogen, oxygen, phosphorus and sulfur atoms. Preference is given to compounds which contain at least one nitrogen atom and, if appropriate, additionally at least one further heteroatom other than nitrogen. Preference is given to compounds which contain at least one nitrogen atom, particularly preferably 1 to 10 nitrogen atoms, in particular 1 to 5 nitrogen atoms, very particularly preferably 1 to 3 nitrogen atoms and especially 1 or 2 nitrogen atoms. The latter nitrogen compounds may contain other heteroatoms such as oxygen, sulfur or phosphorus atoms.

The nitrogen atom is z. B. a suitable carrier of the positive charge in the cation of the ionic liquid. In the event that the nitrogen atom is the carrier of the positive charge in the cation of the ionic liquid, in the synthesis of the ionic liquids, a cation can first be generated by quaternization on the nitrogen atom of, for example, an amine or nitrogen heterocycle. The quaternization can be carried out by protonation of the nitrogen atom. Depending on the protonation reagent used, salts with different anions are obtained. In cases where it is not possible to form the desired anion already during the quaternization, this can be done in a further synthesis step. Starting from, for example, an ammonium halide, the halide can be reacted with a Lewis acid to form a complex anion from halide and Lewis acid. Alternatively, replacement of a halide ion with the desired anion is possible. This can be done by adding a metal salt to precipitate the metal halide formed, via an ion exchanger, or by displacing the halide ion with a strong acid (to release the hydrohalic acid). Suitable methods are, for example, in Angew. Chem. 2000, 112, pp. 3926-3945 and the literature cited therein.

Prefers are such compounds that have at least a five- to six-membered heterocycle, in particular a five-membered Heterocycle, containing at least one nitrogen atom as well optionally having an oxygen or sulfur atom, especially preference is given to those compounds which have at least one to contain six-membered heterocycle, the one, two or three Has nitrogen atoms and a sulfur or an oxygen atom, most preferably those having two nitrogen atoms. Farther preferred are aromatic heterocycles.

Especially preferred compounds are those which have a molar mass of less than 1000 g / mol, most preferably less than 800 g / mol and in particular less than 500 g / mol.

sowie Oligomeren, die diese Strukturen enthalten, worin
R für Wasserstoff, Alkyl, Alkenyl, Cycloalkyl, Cycloalkenyl, Polycyclyl, Heterocycloalkyl, Aryl oder Heteroaryl stehen;
Reste R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ und R⁹, die an ein Ringkohlenstoffatom gebunden sind, unabhängig voneinander für Wasserstoff, eine Sulfogruppe, COOH, Carboxylat, Sulfonat, Acyl, Alkoxycarbonyl, Cyano, Halogen, Hydroxyl, SH, Nitro, NE¹E², Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkenyl, Cycloalkyl, Cycloalkyloxy, Cycloalkenyl, Cycloalkenyloxy, Polycyclyl, Polycyclyloxy, Heterocycloalkyl, Aryl, Aryloxy oder Heteroaryl stehen, wobei E¹ und E² unabhängig voneinander für Wasserstoff, Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl oder Hetaryl stehen,
Reste R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ und R⁹, die an ein Ringheteroatom gebunden sind, für Wasserstoff, SO₃H, NE¹E², Alkyl, Alkoxy, Alkenyl, Cycloalkyl, Cycloalkenyl, Polycyclyl, Heterocycloalkyl, Aryl oder Heteroaryl, stehen, wobei E¹ und E² unabhängig voneinander für Wasserstoff, Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl oder Hetaryl stehen, oder
zwei benachbarte Reste R¹ bis R⁹ auch zusammen mit den Ringatomen, an die sie gebunden sind, für wenigstens einen anellierten, gesättigten, ungesättigten oder aromatischen Ring oder ein Ringsystem mit 1 bis 30 Kohlenstoffatomen stehen können, wobei der Ring oder das Ringsystem 1 bis 5 nicht benachbarte Heteroatome oder heteroatomhaltige Gruppen aufweisen kann und wobei der Ring oder das Ringsystem unsubstituiert oder substituiert sein kann,
wobei zwei geminale Reste R¹ bis R⁹ auch gemeinsam für =O, =S oder =NR^b stehen können, wobei R^b für Wasserstoff, Alkyl, Cycloalkyl, Aryl oder Heteroaryl steht,
wobei in den Verbindungen der Formel (IV.x.1) R¹ und R³ oder R³ und R⁵ auch gemeinsam für den Bindungsanteil einer Doppelbindung zwischen den Ringatomen, die diese Reste tragen, stehen können,
wobei einer der Reste R, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ oder R⁹ für eine Bindungsstelle an die Linkergruppe stehen kann;
B in den Verbindungen der Formeln (IV.x.1) und (IV.x.2) zusammen mit der C-N-Gruppe, an die es gebunden ist, einen 4- bis 8-gliedrigen, gesättigten oder ungesättigten oder aromatischen Cyclus bildet, der gegebenenfalls substituiert ist. und/oder der gegebenenfalls weitere Heteroatome oder heteroatomhaltige Gruppen aufweisen kann und/oder der weitere anellierte gesättigte, ungesättigte oder aromatische Carbocyclen oder Heterocyclen umfassen kann.Preferred cations in the salt group are selected from the compounds of the formulas (IV.a) to (IV.w),

and oligomers containing these structures, wherein
R is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, polycyclyl, heterocycloalkyl, aryl or heteroaryl;
Radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ attached to a ring carbon atom independently of one another represent hydrogen, a sulfo group, COOH, carboxylate, sulfonate, acyl , Alkoxycarbonyl, cyano, halogen, hydroxyl, SH, nitro, NE ¹ E ² , alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, cycloalkyl, cycloalkyloxy, cycloalkenyl, cycloalkenyloxy, polycyclyl, polycycloxy, heterocycloalkyl, aryl, aryloxy or heteroaryl where E ¹ and E ² independently of one another are hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl,
Radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ , which are bonded to a ring heteroatom, for hydrogen, SO ₃ H, NE ¹ E ² , alkyl, alkoxy , Alkenyl, cycloalkyl, cycloalkenyl, polycyclyl, heterocycloalkyl, aryl or heteroaryl, wherein E ¹ and E ² independently of one another represent hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, or
two adjacent radicals R ¹ to R ⁹ together with the ring atoms to which they are attached may stand for at least one fused, saturated, unsaturated or aromatic ring or a ring system having 1 to 30 carbon atoms, the ring or the ring system 1 to 5 may have non-adjacent heteroatoms or heteroatom-containing groups and wherein the ring or the ring system may be unsubstituted or substituted,
where two geminal radicals R ¹ to R ^{9 can} also together stand for = O, = S or = NR ^b , where R ^{b is} hydrogen, alkyl, cycloalkyl, aryl or heteroaryl,
where in the compounds of the formula (IV.x.1) R ¹ and R ³ or R ³ and R ^{5 may} also together be the bond moiety of a double bond between the ring atoms which carry these radicals,
wherein one of R, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ or R ⁹ may be a linking site to the linker group;
B in the compounds of the formulas (IV.x.1) and (IV.x.2) together with the CN group to which it is attached forms a 4- to 8-membered, saturated or unsaturated or aromatic cycle, which is optionally substituted. and / or may optionally have further heteroatoms or heteroatom-containing groups and / or may comprise further fused saturated, unsaturated or aromatic carbocycles or heterocycles.

Preferably, at least one of the radicals, in particular one of the radicals R, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ or R ^{9 is} a binding site to the linker group. In the cations of formulas IV.a, IV.b, IV.c, IV.d, IV.e, IV.f, IV.g, IV.g., IV.h, IV.i, IV.j, IV.j ', IV.k, IV.k', IV.I, IV.m, IV.m ', IV.n, IV.n', IV.o, IV.o ', IV.p, IV .q, IV.q ', IV.q'', IV.r, IV.r'',IV.r'', IV.s, IV.t, IV.w and IV.x may be linked to the Linker group via a carbon ring atom or a nitrogen ring atom of the heterocycle. It is preferred that the attachment to the linker group is via a carbon ring atom of the heterocycle (correct?). In the cations of the formula IV.v the attachment to the linker group is preferably via one of the radicals R ¹ , R ² or R.

With regard to the general meaning of the abovementioned radicals carboxylate, sulfonate, acyl, alkoxycarbonyl, halogen, NE ¹ E ² , alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, cycloalkyl, cycloalkyloxy, cycloalkenyl, cycloalkenyloxy, polycyclyl, polycyclyloxy, heterocycloalkyl, aryl , Aryloxy or heteroaryl, reference is made in full to the statements made at the outset. Radicals R ¹ to R ⁹ which are bonded to a carbon atom in the abovementioned formulas (IV) and have a heteroatom or a heteroatom-containing group can also be bonded to the carbon atom directly via a heteroatom.

Two adjacent radicals R ¹ to R ^9, together with the ring atoms to which they are attached, form at least one fused, saturated, unsaturated or aromatic ring or a ring system having from 1 to 30 carbon atoms, the ring or the ring system not being adjacent to 1 to 5 Heteroatoms or heteroatom-containing groups may have and wherein the ring or the ring system may be unsubstituted or substituted, these radicals may together as fused building blocks preferably 1,3-propylene, 1,4-butylene, 1,5-pentylene, 2-oxa 1,3-propylene, 1-oxa-1,3-propylene, 2-oxa-1,3-propylene, 1-oxa-1,3-propenylene, 3-oxa-1,5-pentylene, 1-aza- 1,3-propenylene, 1-C ₁ -C ₄ -alkyl-1-aza-1,3-propenylene, 1,4-buta-1,3-dienylene, 1-aza-1,4-buta-1, 3-dienyls or 2-aza-1,4-buta-1,3-dienyls.

• – unsubstituiertes C₁- bis C₁₈-Alkyl wie Methyl, Ethyl, 1-Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4-Methyl-2-pentyl, 2-Methyl-3-pentyl, 3-Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, 1-Heptyl, 1-Octyl, 1-Nonyl, 1-Decyl, 1-Undecyl, 1-Dodecyl, 1-Tetradecyl, 1-Hexadecyl und 1-Octadecyl;
• – ein- bis mehrfach mit Hydroxy, Halogen, Phenyl, Cyano, C₁-C₆-Alkoxycarbonyl und/oder SO₃H substituiertes C₁- bis C₁₈-Alkyl, speziell Hydroxy-C₁-C₁₈-alkyl, wie z. B. 2-Hydroxyethyl oder 6-Hydroxyhexyl; Phenyl-C₁-C₁₈-alkyl, wie z. B. Benzyl, 3-Phenylpropyl; Cyano-C₁-C₁₈-alkyl, wie z. B. 2-Cyanoethyl; C₁-C₆-Alkoxy-C₁-C₁₈-alkyl, wie z. B. 2-(Methoxycarbonyl)-ethyl, 2-(Ethoxycarbonyl)-ethyl oder 2-(n-Butoxy-carbonyl)-ethyl; C₁-C₁₈-Fluoralkyl, wie Trifluormethyl, Difluormethyl, Fluormethyl, Pentafluorethyl, Heptafluorpropyl, Heptafluorisopropyl, Nonafluorbutyl, Nonafluorisobutyl, Undecylfluorpentyl, Undecylfluorisopentyl; Sulfo-C₁-C₁₈-alkyl, wie z. B. 3-Sulfopropyl;
• – Hydroxyethyloxyalkyl, Reste von Oligo- und Polyalkylenglycolen wie Polyethylenglycole und Polypropylenglycolen und deren Oligomere mit 2 bis 100 Einheiten und einem Wasserstoff oder einem C₁-C₈-Alkyl als Endgruppe, wie beispielsweise R^AO-(CHR^B-CH₂-O)_n-CHR^B-CH₂- mit R^A und R^B bevorzugt Wasserstoff, Methyl oder Ethyl und n bevorzugt 0 bis 3, insbesondere 3-Oxa-butyl, 3-Oxa-pentyl, 3,6-Dioxa-heptyl, 3,6-Dioxa-octyl, 3,6,9-Trioxa-decyl, 3,6,9-Trioxaundecyl, 3,6,9,12-Tetraoxa-tridecyl und 3,6,9,12-Tetraoxa-tetradecyl; und
• – C₂-C₆-Alkenyl, wie Vinyl oder Propenyl.

Preferably, the radical R, if it does not represent a binding site to the linker group, stands for

• Unsubstituted C ₁ - to C ₁₈ -alkyl, such as methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl ( tert -butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl 2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3- Dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1 Octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl and 1-octadecyl;
• - One to several times with hydroxy, halogen, phenyl, cyano, C ₁ -C ₆ alkoxycarbonyl and / or SO ₃ H substituted C ₁ - to C ₁₈ alkyl, especially hydroxy-C ₁ -C ₁₈ alkyl, such as , 2-hydroxyethyl or 6-hydroxyhexyl; Phenyl-C ₁ -C ₁₈ alkyl, such as. Benzyl, 3-phenylpropyl; Cyano-C ₁ -C ₁₈ alkyl, such as. For example, 2-cyanoethyl; C ₁ -C ₆ alkoxy-C ₁ -C ₁₈ alkyl, such as. B. 2- (methoxycarbonyl) -ethyl, 2- (ethoxycarbonyl) -ethyl or 2- (n-butoxycarbonyl) -ethyl; C ₁ -C ₁₈ fluoroalkyl, such as trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl; Sulfo-C ₁ -C ₁₈ -alkyl, such as. For example, 3-sulfopropyl;
• - Hydroxyethyloxyalkyl, residues of oligo- and polyalkylene glycols such as polyethylene glycols and polypropylene glycols and their oligomers having 2 to 100 units and a hydrogen or a C ₁ -C ₈ alkyl as an end group, such as R ^A O- (CHR ^B -CH ₂ -O ) _n -CHR ^B -CH ₂ - with R ^A and R ^B preferably hydrogen, methyl or ethyl and n preferably 0 to 3, in particular 3-oxa-butyl, 3-oxa-pentyl, 3,6-dioxa-heptyl, 3 , 6-dioxa-octyl, 3,6,9-trioxa-decyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxa-tridecyl and 3,6,9,12-tetraoxa-tetradecyl; and
• - C ₂ -C ₆ alkenyl, such as vinyl or propenyl.

Particularly preferably, the radical R is linear C ₁ - to C ₁₈ -alkyl, such as, for example, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, 1-decyl , 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, most preferably methyl, ethyl, 1-butyl and 1-octyl and CH ₃ O- (CH ₂ CH ₂ O) n -CH ₂ CH ₂ - and OH ₃ CH ₂ O- (CH ₂ CH ₂ O) _m -CH ₂ CH ₂ - with m being 0 to 3.

• – Wasserstoff;
• – Halogen;
• – eine funktionelle Gruppe ausgewählt unter Hydroxy, Alkoxy, Alkylthio, Carboxyl, -COOH, Sulfonat, Cyano, Acyl, Alkoxycarbonyl, NE¹E² und Nitro, wobei E¹ und E² wie zuvor definiert sind;
• – C₁-C₁₈-Alkyl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist und/oder, wie eingangs definiert, durch wenigstens ein Heteroatom oder eine heteroatomhaltige Gruppe unterbrochen sein kann;
• – C₂-C₁₈-Alkenyl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist und/oder, wie eingangs definiert, durch wenigstens ein Heteroatom unterbrochen sein kann;
• – C₆-C₁₀-Aryl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist;
• – C₅-C₁₂-Cycloalkyl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist;
• – Polycyclyl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist;
• – C₅-C₁₂-Cycloalkenyl, das unsubstituiert ist, oder, wie eingangs definiert, substituiert ist;
• – Heterocycloalkyl mit 5 oder 6 Ringatomen, wobei der Ring neben Kohlenstoffringgliedern 1, 2 oder 3 Heteroatome oder heteroatomhaltige Gruppen aufweist, die ausgewählt sind unter Sauerstoff, Stickstoff, Schwefel und NR^a, und das unsubstituiert ist oder, wie eingangs definiert, substituiert ist;
• – Heteroaryl mit 5 bis 10 Ringatomen, wobei der Ring neben Kohlenstoffringgliedern 1, 2 oder 3 Heteroatome oder heteroatomhaltige Gruppen aufweist, die ausgewählt sind unter Sauerstoff, Stickstoff, Schwefel und NR^a, und das unsubstituiert ist oder, wie eingangs definiert, substituiert ist;
• – wobei wenigstens einer der Reste R¹ bis R⁹, insbesondere einer der Reste R¹ bis R⁹ auch für eine Bindungsstelle zu der Linkergruppe stehen kann.

The radicals R ¹ to R ⁹ are preferably each independently

• - hydrogen;
• - halogen;
• A functional group selected from hydroxy, alkoxy, alkylthio, carboxyl, -COOH, sulfonate, cyano, acyl, alkoxycarbonyl, NE ¹ E ² and nitro, wherein E ¹ and E ^{2 are} as defined above;
• C ₁ -C ₁₈ -alkyl which is unsubstituted or, as defined above, is substituted and / or, as defined above, may be interrupted by at least one heteroatom or a heteroatom-containing group;
• - C ₂ -C ₁₈ alkenyl which is unsubstituted or, as defined above, is substituted and / or, as defined above, may be interrupted by at least one heteroatom;
• - C ₆ -C ₁₀ -aryl which is unsubstituted or substituted as defined above;
• - C ₅ -C ₁₂ cycloalkyl which is unsubstituted or substituted as defined above;
• - Polycyclyl, which is unsubstituted or, as defined above, is substituted;
• C ₅ -C ₁₂ cycloalkenyl which is unsubstituted or substituted as defined above;
• - Heterocycloalkyl having 5 or 6 ring atoms, wherein the ring in addition to carbon ring members 1, 2 or 3 heteroatom or heteroatom-containing groups which are selected from oxygen, nitrogen, sulfur and NR ^a , and which is unsubstituted or, as defined above, is substituted;
• - heteroaryl having 5 to 10 ring atoms, wherein the ring next to carbon ring members 1, 2 or 3 heteroatom or heteroatom-containing groups which are selected from oxygen, nitrogen, sulfur and NR ^a , and which is unsubstituted or, as defined above, is substituted;
• - Where at least one of the radicals R ¹ to R ⁹ , in particular one of the radicals R ¹ to R ^{9 can} also stand for a binding site to the linker group.

It is also preferred that two adjacent radicals R ¹ to R ⁹ together with the ring atoms to which they are attached may stand for at least one fused, saturated, unsaturated or aromatic ring or a ring system having 1 to 12 carbon atoms, said Ring or the ring system may have 1 to 5 non-adjacent heteroatoms or heteroatom-containing groups, which are preferably selected from oxygen, nitrogen, sulfur and NR ^a , and wherein the ring or the ring system is unsubstituted or may be substituted, wherein the substituents are preferably independently are selected from alkoxy, cycloalkyl, cycloalkoxy, polycyclyl, polycycloxy, heterocycloalkyl, aryl, aryloxy, arylthio, heteroaryl, halogen, hydroxy, SH, = O, SS, = NR ^a , COOH, carboxylate, -SO ₃ H, sulphonate, NE ¹ E ² , nitro and cyano, wherein E ¹ and E ² independently of one another represent hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl.

When R ¹ to R ^{9 are} alkoxy, R ¹ to R ^{9 are} preferably methoxy or ethoxy or R ^A O- (CH ₂ CH ₂ CH ₂ CH ₂ O) _n -CH ₂ CH ₂ CH ₂ CH ₂ O. with R ^A and R ^B preferably hydrogen, methyl or ethyl and n preferably 0 to 3.

When R ¹ to R ^{9 are} acyl, R ¹ to R ^{9 are} preferably formyl and C ₁ -C ₄ alkylcarbonyl, in particular formyl or acetyl.

When R ¹ to R ^{9 are} C ₁ -C ₁₈ -alkyl, R ¹ to R ^{9 are} preferably unsubstituted C ₁ -C ₁₈ -alkyl, such as methyl, ethyl, 1-propyl, 2-propyl, 1-butyl , 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-9-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl 1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3 pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2, 3-Dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, 1,1,3,3-tetramethylbutyl, 1-nonyl, 1- Decyl, 1-undecyl, 1-dodecyl, 1-tridecyl, 1-tetradecyl, 1-pentadecyl, 1-hexadecyl, 1-heptadecyl, 1-octadecyl;
C ₁ -C ₁₈ -haloalkyl, especially C ₁ -C ₁₈ -fluoroalkyl, for example trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonofluoroisobutyl, undecylfluoropentyl, undecylisopentyl, C ₆ F ₁₃ , C ₈ F ₁₇ , C ₁₀ F ₂₁ , C ₁₂ F ₂₅ , especially C ₁ -C ₁₈ -chloroalkyl, such as chloromethyl, 2-chloroethyl, trichloromethyl, 1,1-dimethyl-2-chloroethyl;
Amino-C ₁ -C ₁₈ -alkyl, such as 2-aminoethyl, 2-aminopropyl, 3-aminopropyl, 4-aminobutyl, 6-aminohexyl, C ₁ -C ₆ -alkylamino-C ₁ -C ₁₈ -alkyl, such as 2-aminoethyl Methylaminoethyl, 2-methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl;
Di (C ₁ -C ₆ alkyl) C ₁ -C ₁₈ alkyl such as 2-dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethylaminobutyl, 6-dimethylaminohexyl, cyano-C ₁ -C ₁₈ -alkyl such as 2-cyanoethyl, 2-cyanopropyl, C ₁ -C ₁₀ alkoxy-C ₁ -C ₁₈ alkyl such as methoxymethyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-methoxyisopropyl, 4-methoxybutyl, 6 Methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl, 6-ethoxyhexyl, 2-isopropoxyethyl, 2-butoxyethyl, 2-butoxypropyl, 2-octyloxyethyl, 5-methoxy-3-oxa-pentyl, 8 -Methoxy-3,6-dioxa-octyl, 7-methoxy-4-oxa-heptyl, 11-methoxy-4,8-dioxa-undecyl, 9-methoxy-5-oxa-nonyl, 9-methoxy-5-oxa nonyl, 14-methoxy-5,10-dioxa-tetradecyl, 5-ethoxy-3-oxapentyl, 8-ethoxy-3,6-dioxa-octyl, 7-ethoxy-4-oxa-heptyl, 11-ethoxy-4 , 8-dioxa-undecyl, 9-ethoxy-5-oxa-nonyl or 14-ethoxy-5,10-oxa-tetradecyl, 15-methoxy-4,8,12-trioxapentadecyl, 11-methoxy-3,6,9 trioxa-undecyl, 11-ethoxy-3,6,9-trioxa-undecyl, 15-ethoxy-4,8,12-trioxa-pentadecyl;
Di- (C ₁ -C ₁₀ -acoxy-C ₁ -C ₁₈ -alkyl), such as diethoxymethyl or diethoxyethyl, C ₁ -C ₆ -alkoxycarbonyl-C ₁ -C ₁₈ -alkyl, such as 2- (methoxycarbonyl) -ethyl, 2- (ethoxycarbonyl) -ethyl, 2- (n-butoxycarbonyl) -ethyl, di- (C ₁ -C ₆ -alkoxycarbonyl) -C ₁ -C ₁₈ -alkyl, such as 1,2-di- (methoxycarbonyl) -ethyl , Hydroxy-C ₁ -C ₁₈ -alkyl, such as 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2-hydroxy-2,2-dimethylethyl, 5-hydroxy-3-oxa pentyl, 8-hydroxy-3,6-dioxo-octyl, 11-hydroxy-3,6,9-trioxa-undecyl, 7-hydroxy-4-oxa-heptyl, 11-hydroxy-4,8-dioxa-undecyl, 15-hydroxy-4,8,12-trioxa-pentadecyl, 9-hydroxy-5-oxanonyl, 14-hydroxy-5,10-dioxa-tetradecyl;
C ₁ -C ₁₂ -alkylsulfanyl-C ₁ -C ₁₈ -alkyl, such as butylthiomethyl, 2-dodecylthioethyl, C ₅ -C ₁₂ -cycloalkyl-C ₁ -C ₁₈ -alkyl, such as cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, Cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, phenyl-C ₁ -C ₁₈ alkyl, wherein the phenyl moiety of phenyl-C ₁ -C ₁₈ alkyl is unsubstituted or mono-, di-, tri or tetra-substituted, and the Substituents are independently selected from C ₁ -C ₆ -alkyl, halogen, C ₁ -C ₆ -alkoxy and nitro, such as benzyl (phenylmethyl), 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, p-tolylmethyl, 1 (p-butylphenyl) -ethyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, phenyl-C (CH ₃ ) ₂ -, 2,6-dimethylphenylmethyl, diphenyl-C ₁ -C ₁₈ - alkyl, such as diphenylmethyl (benzhydryl);
Triphenyl-C ₁ -C ₁₈ -alkyl, such as triphenylmethyl;
Phenoxy-C ₁ -C ₁₈ -alkyl such as 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl;
Phenylthio-C ₁ -C ₁₈ -alkyl, such as 2-phenylthioethyl.

When R ¹ to R ^{9 are} C ₂ -C ₁₈ -alkenyl, R ¹ to R ^{9 are} preferably C ₂ -C ₆ -alkenyl, such as vinyl, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or C ₂ -C ₁₈ alkenyl which is partially or completely substituted by fluorine.

When R ¹ to R ^{9 are} C ₆ -C ₁₀ -aryl, R ¹ to R ^{9 are} preferably phenyl or naphthyl, wherein phenyl or naphthyl is unsubstituted or mono-, di-, tri- or tetra-substituted, wherein the substituents independently of one another are halogen, C ₁ -C ₁₅ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylsulfanyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ - C ₆ alkylcarbonyl, amino, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ dialkyl) amino and nitro are selected, such as phenyl, methylphenyl (tolyl), dimethylphenyl (xylyl), such as. B. 2,6-dimethylphenyl, trimethylphenyl, such as B. 2,4,6-trimethylphenyl, ethylphenyl, diethylphenyl, iso-propylphenyl, tert-butylphenyl, dodecylphenyl, chlorophenyl, di chlorophenyl, trichlorophenyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, 2,6-dichlorophenyl, 4- Bromophenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, 2,6-dimethoxyphenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl, 4-dimethylaminophenyl, 4-acetylphenyl, methoxyethylphenyl, ethoxymethylphenyl, methylthiophenyl, Isopropylthiophenyl, tert-butylthiophenyl, α-naphthyl, β-naphthyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, or partially fluorinated phenyl or perfluorinated phenyl.

When R ¹ to R ^{9 are} C ₅ -C ₁₂ -cycloalkyl, R ¹ to R ^{9 are} preferably unsubstituted cycloalkyl, such as cyclopentyl or cyclohexyl;
C ₅ -C ₁₂ -cycloalkyl which is monosubstituted or disubstituted, where the substituents are independently selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylsulfanyl or chlorine, z. Butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl;
C ₅ -C ₁₂ -cycloalkyl which is completely or completely fluorinated.

When R ¹ to R ^{9 are} polycyclyl, R ¹ to R ^{9 are} preferably C ₅ -C ₁₂ -bicycloalkyl, such as norbornyl or C ₅ -C ₁₂ -bicycloalkenyl, such as norbornenyl.

When R ¹ to R ^{9 are} C ₅ -C ₁₂ cycloalkenyl, R ¹ to R ^{9 are} preferably unsubstituted cycloalkenyl, such as cyclopent-2-en-1-yl, cyclopent-3-en-1-yl, cyclohex 2-en-1-yl, cyclohex-1-en-1-yl, cyclohexa-2,5-dien-1-yl or partially or completely fluorinated cycloalkenyl.

When R ¹ to R ^{9 are} heterocycloalkyl having 5 or 6 ring atoms, R ¹ to R ^{9 are} preferably 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1, 3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl.

When R ¹ to R ^{9 are} heteroaryl, R ¹ to R ^{9 are} preferably furyl, thienyl, pyrryl, pyridyl, indolyl, benzoxazolyl, benzimidazolyl, benzthiazolyl. In the case of substitution hetaryl carries 1, 2 or 3 substituents which are independently selected from C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy and halogen, for example dimethylpyridyl, methylquinolyl, dimethylpyrryl, methoxyfuryl, dimethoxypyridyl or difluoropyridyl.

• – Wasserstoff;
• – unverzweigtes oder verzweigtes, unsubstituiertes oder ein bis mehrfach mit Hydroxy, Halogen, Phenyl, Cyano, C₁-C₆-Alkoxycarbonyl und/oder Sulfogruppe substituiertes C₁-C₁₈-Alkyl, wie beispielsweise Methyl, Ethyl, 1-Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4-Methyl-2-pentyl, 2-Methyl-3-pentyl, 3-Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, 1-Heptyl, 1-Octyl, 1-Nonyl, 1-Decyl, 1-Undecyl, 1-Dodecyl, 1-Tetradecyl, 1-Hexadecyl, 1-Octadecyl, 2-Hydroxyethyl, Benzyl, 3-Phenylpropyl, 2-Cyanoethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n-Butoxycarbonylmethyl, tert-Butoxycarbonylmethyl, 2-(Methoxycarbonyl)-ethyl, 2-(Ethoxycarbonyl)-ethyl, 2-(n-Butoxy-carbonyl)-ethyl, Trifluormethyl, Difluormethyl, Fluormethyl, Pentafluorethyl, Heptafluorpropyl, Heptafluorisopropyl, Nonafluorbutyl, Nonafluorisobutyl, Undecylfluorpentyl, Undecylfluorisopentyl, 6-Hydroxyhexyl und 3-Sulfopropyl;
• – Hydroxyethyloxyalkyl, Reste von Oligo- und Polyalkylenglycolen wie Polyethylenglycole und Polypropylenglycolen und deren Oligomere mit 2 bis 100 Einheiten und einem Wasserstoff oder einem C₁-C₈-Alkyl als Endgruppe, wie beispielsweise R^AO-(CHR^B-CH₂-O)_n-CHR^B-CH₂- oder R^AO-(CH₂CH₂CH₂CH₂O)n-CH₂CH₂CH₂CH₂O- mit R^A und R^B bevorzugt Wasserstoff, Methyl oder Ethyl und n bevorzugt 0 bis 3, insbesondere 3-Oxabutyl, 3-Oxapentyl, 3,6-Dioxaheptyl, 3,6-Dioxaoctyl, 3,6,9-Trioxadecyl, 3,6,9-Trioxaundecyl, 3,6,9,12-Tetraoxatridecyl und 3,6,9,12-Tetraoxatetradecyl;
• – C₂-C₄-Alkenyl wie Vinyl und Allyl; und
• – N,N-Di-C₁-C₆-alkyl-amino, wie beispielsweise N,N-Dimethylamino und N,N-Diethylamino,
• – wobei wenigstens einer der Reste R¹ bis R⁹, insbesondere einer der Reste R¹ bis R⁹ auch für eine Bindungsstelle zu der Linkergruppe stehen kann.

Particularly preferably, the radicals R ¹ to R ⁹ are each independently

• - hydrogen;
• - C ₁ -C ₁₈ -alkyl which is unbranched or branched, unsubstituted or monosubstituted to polysubstituted by hydroxyl, halogen, phenyl, cyano, C ₁ -C ₆ -alkoxycarbonyl and / or sulpho group, such as, for example, methyl, ethyl, 1-propyl, 2 Propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2- Methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3 Hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl 1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1 Tetradecyl, 1-hexadecyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl, 2-cyanoethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-butoxycarbonylmethyl, tert-butoxycarbonylme ethyl, 2- (methoxycarbonyl) -ethyl, 2- (ethoxycarbonyl) -ethyl, 2- (n-butoxycarbonyl) -ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, 6-hydroxyhexyl and 3-sulfopropyl;
• - Hydroxyethyloxyalkyl, residues of oligo- and polyalkylene glycols such as polyethylene glycols and polypropylene glycols and their oligomers having 2 to 100 units and a hydrogen or a C ₁ -C ₈ alkyl as an end group, such as R ^A O- (CHR ^B -CH ₂ -O ) _n -CHR ^B -CH ₂ - or R ^A O- (CH ₂ CH ₂ CH ₂ CH ₂ O) n-CH ₂ CH ₂ CH ₂ CH ₂ O- with R ^A and R ^B preferably hydrogen, methyl or ethyl and n preferably 0 to 3, in particular 3-oxabutyl, 3-oxapentyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12 Tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl;
• C ₂ -C ₄ alkenyl, such as vinyl and allyl; and
• N, N-di-C ₁ -C ₆ -alkylamino, such as, for example, N, N-dimethylamino and N, N-diethylamino,
• - Where at least one of the radicals R ¹ to R ⁹ , in particular one of the radicals R ¹ to R ^{9 can} also stand for a binding site to the linker group.

Most preferably, the radicals R ¹ to R ⁹ are each independently hydrogen; C ₁ -C ₁₈ alkyl, such as methyl, ethyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl; phenyl; 2-hydroxyethyl; 2-cyano ethyl; 2- (alkoxycarbonyl) ethyl such as 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl or 2- (n-butoxycarbonyl) ethyl; N, N- (C ₁ -C ₄ -dialkyl) amino, such as N, N-dimethylamino or N, N-diethylamino; Chlorine, as well as residues of Oligoalkylenglycol, such as CH ₃ O- (CH ₂ CH ₂ O) n-CH ₂ CH ₂ - or CH ₃ CH ₂ O- (CH ₂ CH ₂ O) _n -CH ₂ CH ₂ - with n is the same 0 to 3. Equally particularly preferably given before at least one of the radicals R ¹ to R ⁹ , in particular one of the radicals R ¹ to R ^{9 is} also a binding site to the linker group.

• – einer der Reste R¹ bis R⁵ Methyl, Ethyl oder Chlor ist, ein weiterer der Reste R¹ bis R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff sind;
• – R³ Dimethylamino ist, einer der Reste R¹, R², R⁴ und R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹, R², R⁴ und R⁵ Wasserstoff sind;
• – einer der Reste R¹ bis R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff sind;
• – R² Carboxy oder Carboxamid ist, einer der Reste R¹, R³, R⁴ und R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹, R³, R⁴ und R⁵ Wasserstoff sind; oder
• – R¹ und R² oder R² und R³ 1,4-Buta-1,3-dienylen ist, einer der Reste R¹, R³, R⁴ und R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹, R³, R⁴ und R⁵ Wasserstoff sind; und insbesondere solche, bei denen
• – einer der Reste R¹ bis R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff sind; oder
• – einer der Reste R¹ bis R⁵ Methyl oder Ethyl ist, einer der Reste R¹ bis R⁵ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff sind.

Very particularly preferred pyridinium ions (IVa) are those in which

• One of the radicals R ¹ to R ^{5 is} methyl, ethyl or chlorine, another of the radicals R ¹ to R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{5 are} hydrogen;
• R ^{3 is} dimethylamino, one of the radicals R ¹ , R ² , R ⁴ and R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ , R ² , R ⁴ and R ^{5 are} hydrogen;
• - One of the radicals R ¹ to R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{5 are} hydrogen;
• R ^{2 is} carboxy or carboxamide, one of the radicals R ¹ , R ³ , R ⁴ and R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ , R ³ , R ⁴ and R ^{5 are} hydrogen; or
• - R ¹ and R ² or R ² and R ^{3 is} 1,4-buta-1,3-dienylene, one of the radicals R ¹ , R ³ , R ⁴ and R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ , R ³ , R ⁴ and R ^{5 are} hydrogen; and in particular those in which
• - One of the radicals R ¹ to R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{5 are} hydrogen; or
• - One of the radicals R ¹ to R ^{5 is} methyl or ethyl, one of the radicals R ¹ to R ^{5 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{5 are} hydrogen.

Especially preferred pyridinium ions (IVa) are derived from cations which are selected from pyridinium, 2-methylpyridinium, 2-ethylpyridinium, 5-ethyl-2-methylpyridinium and 2-methyl-3-ethylpyridinium as well 1-methylpyridinium, 1-ethylpyridinium, 1- (1-butyl) pyridinium, 1- (1-hexyl) pyridinium, 1- (1-octyl) -pyridinium, 1- (1-hexyl) -pyridinium, 1- (1-octyl) -pyridinium, 1- (1-dodecyl) -pyridinium, 1- (1-tetradecyl) -pyridinium, 1- (1-hexadecyl) -pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1- (1-butyl) -2-methylpyridinium, 1- (1-hexyl) -2-methylpyridinium, 1- (1-octyl) -2-methylpyridinium, 1- (1-dodecyl) -2-methylpyridinium, 1- (1-tetradecyl) -2-methylpyridinium, 1- (1-hexadecyl) -2-methylpyridinium, 1-methyl-2-ethylpyridinium, 1,2-diethylpyridinium, 1- (1-butyl) -2-ethylpyridinium, 1- (1-hexyl) -2-ethylpyridinium, 1- (1-octyl) -2-ethylpyridinium, 1- (1-dodecyl) -2-ethylpyridinium, 9- (1-tetradecyl) -2-ethylpyridinium, 1- (1-hexadecyl) -2-ethylpyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-diethyl-2-methylpyridinium, 1- (1-butyl) -2-methyl-3-ethylpyridinium, 1- (1-hexyl) -2-methyl-3-ethylpyridinium and 1- (1-octyl) -2-methyl-3-ethylpyridinium, 1- (1-dodecyl) -2-methyl-3-ethylpyridinium, 1- (1-Tetradecyl) -2-methyl-3-ethylpyridinium and 1- (1-hexadecyl) -2-methyl-3-ethylpyridinium and have a free valence on the pyridine ring.

• – einer der Reste R¹ bis R⁴ eine Bindungsstelle zu der Linkergruppe ist und die verbleibenden Reste R¹ bis R⁴ für Wasserstoff stehen, oder
• – einer der Reste R¹ bis R⁴ für Methyl oder Ethyl steht, ein weiterer der Reste R¹ bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R¹ bis R⁴ für Wasserstoff stehen.

Particularly preferred pyridazinium ions (IVb) are those in which

• - One of the radicals R ¹ to R ^{4 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{4 are} hydrogen, or
• - One of the radicals R ¹ to R ^{4 is} methyl or ethyl, another of the radicals R ¹ to R ^{4 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{4 are} hydrogen.

• – R¹ für Wasserstoff, Methyl oder Ethyl steht, einer der Reste R² bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R² bis R⁴ unabhängig voneinander Wasserstoff oder Methyl sind, oder
• – R¹ für eine Bindungsstelle zu der Linkergruppe steht und R² bis R⁴ unabhängig voneinander Wasserstoff oder Methyl sind oder
• – R¹ für Wasserstoff, Methyl oder Ethyl steht und R² und R⁴ für Methyl stehen und R³ für eine Bindungsstelle zu der Linkergruppe steht.

Particularly preferred pyrimidinium ions (IVc) are those in which

• R ^{1 is} hydrogen, methyl or ethyl, one of R ² to R ^{4 is} a linking site to the linker group and the remaining R ² to R ^{4 are} independently hydrogen or methyl, or
• - R ^{1 is} a binding site to the linker group and R ² to R ^{4 are} independently hydrogen or methyl or
• - R ^{1 is} hydrogen, methyl or ethyl and R ² and R ^{4 are} methyl and R ^{3 is} a point of attachment to the linker group.

• – R¹ für Wasserstoff, Methyl oder Ethyl steht, einer der Reste R² bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R² bis R⁴ unabhängig voneinander Wasserstoff oder Methyl sind, oder
• – R¹ für Wasserstoff, Methyl oder Ethyl steht und R² und R⁴ für Methyl stehen und R³ für eine Bindungsstelle zu der Linkergruppe steht, oder
• – einer der Reste R¹ bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R¹ bis R⁴ für Methyl stehen; oder
• – einer der Reste R¹ bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R¹ bis R⁴ für Wasserstoff stehen.

Particularly preferred pyrazinium ions (IVd) are those in which

• R ^{1 is} hydrogen, methyl or ethyl, one of R ² to R ^{4 is} a linking site to the linker group and the remaining R ² to R ^{4 are} independently hydrogen or methyl, or
• R ^{1 is} hydrogen, methyl or ethyl and R ² and R ^{4 are} methyl and R ^{3 is} a binding site to the linker group, or
• - One of the radicals R ¹ to R ^{4 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{4 are} methyl; or
• - One of the radicals R ¹ to R ^{4 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{4 are} hydrogen.

• – R¹ für Wasserstoff, Methyl, Ethyl, 1-Propyl, 1-Butyl, 1-Pentyl, 1-Hexyl, 1-Octyl, 2-Hydroxyethyl oder 2-Cyanoethyl steht, einer der Reste R² bis R⁴ für eine Bindungs stelle zu der Linkergruppe steht und die verbleibenden Reste R² bis R⁴ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen; oder
• – R¹ für eine freie Bindungsstelle zu der Linkergruppe steht und R² bis R⁴ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen.

Particularly preferred imidazolium ions (IVe) are those in which

• - R ^{1 is} hydrogen, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-octyl, 2-hydroxyethyl or 2-cyanoethyl, one of the radicals R ² to R ^{4 is} a bond represents the linker group and the remaining radicals R ² to R ⁴ independently of one another represent hydrogen, methyl or ethyl; or
• - R ^{1 is} a free binding site to the linker group and R ² to R ^{4 are} independently hydrogen, methyl or ethyl.

Especially suitable imidazolium ions (IVe) are derived from cations which are selected from 1-methylimidazolium, 1-ethylimidazolium, 1- (1-propyl) -imidazolium, 1- (1-allyl) -imidazolium, 1- (1-butyl) -imidazolium, 1- (1-octyl) -imidazolium, 1- (1-dodecyl) imidazolium, 1- (1-tetradecyl) -imidazolium, 1- (1-hexadecyl) imidazolium, 1,3-dimethyl imidazolium, 1,3-diethyl imidazolium, 1-ethyl-3-methylimidazolium, 1- (1-butyl) -3-methylimidazolium, 1- (1-butyl) -3-ethylimidazolium, 1- (1-hexyl) -3-methyl-imidazolium, 1- (1-hexyl) -3-ethylimidazolium, 1- (1-hexyl) -3-butylimidazolium, 1- (1-octyl) -3-methylimidazolium, 1- (1-Octyl) -3-ethylimidazolium, 1- (1-octyl) -3-butylimidazolium, 1- (1-dodecyl) -3-methylimidazolium, 1- (1-dodecyl) -3-ethylimidazolium, 1- (1-dodecyl) -3-butylimidazolium, 1- (1-dodecyl) -3-octylimidazolium, 1- (1-tetradecyl) -3-methylimidazolium, 1- (1-tetradecyl) -3-ethylimidazolium, 1- (1-tetradecyl) -3-butylimidazolium, 1- (1-tetradecyl) -3-octylimidazolium, 1- (1-hexadecyl) -3-methylimidazolium, 1- (1-hexadecyl) -3-ethylimidazolium, 1- (1-hexadecyl) -3-butylimidazolium, 1- (1-hexadecyl) -3-octylimidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1- (1-butyl) -2,3-dimethylimidazolium, 1- (1-hexyl) -2,3-dimethylimidazolium, 1- (1-octyl) -2,3-dimethylimidazolium, 1,4-dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-methylimidazolium, 3-ethylimidazolium, 3-n-propylimidazolium, 3-n-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium, 1,4,5-trimethyl-3-octylimidazolium, 1-Prop-1-en-3-yl-3-methylimidazolium and 1-prop-1-en-3-yl-3-butylimidazolium. Especially suitable imidazolium ions (IVe) are 1,3-diethylimidazolium, 1-ethyl-3-methylimidazolium, 1- (n-butyl) -3-methylimidazolium and have a free valence on the imidazole ring.

• – R¹ für Wasserstoff, Methyl oder Ethyl steht, einer der Reste R² bis R⁴ für eine freie Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R² bis R⁴ unabhängig voneinander Wasserstoff oder Methyl sind, oder
• – R¹ für eine Bindungsstelle zu der Linkergruppe steht und R² bis R⁴ unabhängig voneinander Wasserstoff oder Methyl sind

Particularly preferred pyrazolium ions (IVf), (IVg) or (IVg ') are those in which

• - R ^{1 is} hydrogen, methyl or ethyl, one of R ² to R ^{4 is} a free bond to the linker group and the remaining radicals R ² to R ^{4 are} independently hydrogen or methyl, or
• - R ^{1 is} a binding site to the linker group and R ² to R ^{4 are} independently hydrogen or methyl

• – einer der Reste R¹ bis R⁴ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R¹ bis R⁴ unabhängig voneinander für Wasserstoff oder Methyl stehen.

Particularly preferred pyrazolium ions (IVh) are those in which

• - One of the radicals R ¹ to R ^{4 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{4 are} independently hydrogen or methyl.

Especially preferred pyrazolium ions are derived from cations selected are among pyrazolium and 1,4-dimethylpyrazolium, and have one free valence on the pyrazole ring.

Particular preference is given to using as 1-pyrazolinium (IVi) those in which
one of the radicals R ¹ to R ^{6 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{6 are} independently hydrogen or methyl.

• – R¹ für Wasserstoff, Methyl, Ethyl oder Phenyl steht, einer der Reste R² bis R⁶ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R² bis R⁶ unabhängig voneinander Wasserstoff oder Methyl sind; oder
• – R¹ für einen Linker steht und R² bis R⁶ unabhängig voneinander Wasserstoff oder Methyl sind.

Particularly preferred as 2-pyrazolinium (IVj) or (IVj ') are those in which

• R ^{1 is} hydrogen, methyl, ethyl or phenyl, one of R ² to R ^{6 is} a linking site to the linker group and the remaining R ² to R ^{6 are} independently hydrogen or methyl; or
• - R ^{1 is} a linker and R ² to R ^{6 are} independently hydrogen or methyl.

• – R¹ und R² unabhängig voneinander für Wasserstoff, Methyl, Ethyl oder Phenyl stehen, einer der Reste R³ bis R⁶ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R³ bis R⁶ unabhängig voneinander Wasserstoff oder Methyl sind; oder
• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R² für Wasserstoff, Methyl, Ethyl oder Phenyl steht und R³ bis R⁶ unabhängig voneinander Wasserstoff oder Methyl sind.

Particular preference is given to using as 3-pyrazolinium (IVk) or (IVk ') such, in which

• - R ¹ and R ^{2 are} independently hydrogen, methyl, ethyl or phenyl, one of R ³ to R ^{6 is} a point of attachment to the linker group and the remaining radicals R ³ to R ^{6 are} independent each other are hydrogen or methyl; or
• - One of the radicals R ¹ or R ^{2 is} a binding site to the linker group, the remaining radical R ¹ or R ^{2 is} hydrogen, methyl, ethyl or phenyl and R ³ to R ^{6 are} independently hydrogen or methyl.

• – R¹ und R² unabhängig voneinander für Wasserstoff, Methyl, Ethyl, 1-Butyl oder Phenyl stehen; einer der Reste R³ und R⁴ steht für eine Bindungsstelle zu der Linkergruppe und der verbleibende Rest R³ oder R⁴ für Wasserstoff, Methyl oder Ethyl steht und R⁵ und R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen; oder
• – R¹ und R² unabhängig voneinander für Wasserstoff, Methyl, Ethyl, 1-Butyl oder Phenyl stehen und R³ und R⁴ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen, einer der Reste R⁵ und R⁶ steht für eine Bindungsstelle zu der Linkergruppe und der verbleibende Rest R⁵ oder R⁶ für Wasserstoff oder Methyl steht; oder
• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R² für Wasserstoff, Methyl, Ethyl, 1-Butyl oder Phenyl stehen und R³ und R⁴ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen und R⁵ und R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen.

Particularly preferred imidazolinium ions (IV I) are those in which

• - R ¹ and R ^{2 are} independently hydrogen, methyl, ethyl, 1-butyl or phenyl; one of R ³ and R ⁴ is a linking site to the linker group and the remaining R ³ or R ^{4 is} hydrogen, methyl or ethyl, and R ⁵ and R ^{6 are} independently hydrogen or methyl; or
• - R ¹ and R ^{2 are} independently hydrogen, methyl, ethyl, 1-butyl or phenyl and R ³ and R ^{4 are} independently hydrogen, methyl or ethyl, one of R ⁵ and R ⁶ is a binding site to the linker group and the remaining R ⁵ or R ^{6 is} hydrogen or methyl; or
• - One of the radicals R ¹ or R ^{2 is} a binding site to the linker group, the remaining radical R ¹ or R ^{2 is} hydrogen, methyl, ethyl, 1-butyl or phenyl and R ³ and R ^{4 are} independently hydrogen, methyl or ethyl and R ⁵ and R ^{6 are} independently hydrogen or methyl.

• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R² für Wasserstoff, Methyl oder Ethyl steht und R³ bis R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen; oder
• – R¹ und R² unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen, einer der Reste R³ bis R⁶ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Rest R³ bis R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen.

Particularly preferred imidazolinium ions (IVm) or (IVm ') are those in which

• - One of the radicals R ¹ or R ^{2 is} a binding site to the linker group, the remaining radical R ¹ or R ^{2 is} hydrogen, methyl or ethyl and R ³ to R ^{6 are} independently hydrogen or methyl; or
• - R ¹ and R ^{2 are} independently hydrogen, methyl or ethyl, one of R ³ to R ^{6 is} a binding site to the linker group and the remaining radicals R ³ to R ^{6 are} independently hydrogen or methyl.

• – einer der Reste R¹ bis R³ für eine Bindungsstelle zu der Linkergruppe steht, die verbleibenden Reste R¹ bis R³ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen und R⁴ bis R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen, oder
• – R¹ bis R³ unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen, einer der Reste R⁴ bis R⁶ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R⁴ bis R⁶ unabhängig voneinander für Wasserstoff oder Methyl stehen.

Particularly preferred imidazolinium ions (IVn) or (IVn ') are those in which

• - One of the radicals R ¹ to R ^{3 is} a binding site to the linker group, the remaining radicals R ¹ to R ^{3 are} independently hydrogen, methyl or ethyl and R ⁴ to R ^{6 are} independently hydrogen or methyl, or
• - R ¹ to R ^{3 are} independently hydrogen, methyl or ethyl, one of R ⁴ to R ^{6 is} a binding site to the linker group and the remaining radicals R ⁴ to R ^{6 are} independently hydrogen or methyl.

• – R¹ für eine Bindungsstelle zu der Linkergruppe steht und R² und R³ unabhängig voneinander für Wasserstoff oder Methyl stehen
• – R¹ für Wasserstoff, Methyl, Ethyl oder Phenyl steht, einer der Reste R² oder R³ für eine Bindungsstelle zu der Linkergruppe steht, und der verbleibende Rest R² oder R³ für Wasserstoff oder Methyl stehen.

Particular preference is given to using thiazolium ions (IVo) or (IVo ') and oxazolium ions (IVp) as those in which

• - R ^{1 is} a binding site to the linker group and R ² and R ^{3 are} independently hydrogen or methyl
• - R ^{1 is} hydrogen, methyl, ethyl or phenyl, one of R ² or R ^{3 is} a binding site to the linker group, and the remaining radical R ² or R ^{3 is} hydrogen or methyl.

• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R² für Wasserstoff, Methyl, Ethyl oder Phenyl stehen und R³ für Wasserstoff, Methyl oder Phenyl steht; oder
• – R¹ und R² unabhängig voneinander für Wasserstoff, Methyl, Ethyl oder Phenyl stehen und R³ für eine Bindungsstelle zu der Linkergruppe steht.

Particular preference is given in the process according to the invention as 1,2,4-triazolium (IVq), (IVq ') or (IVq'') such, in which

• - One of the radicals R ¹ or R ^{2 is} a binding site to the linker group, the remaining radical R ¹ or R ^{2 is} hydrogen, methyl, ethyl or phenyl and R ^{3 is} hydrogen, methyl or phenyl; or
• - R ¹ and R ^{2 are} independently hydrogen, methyl, ethyl or phenyl and R ^{3 is} a point of attachment to the linker group.

• – R¹ für eine Bindungsstelle zu der Linkergruppe steht, R² und R³ unabhängig voneinander für Wasserstoff oder Methyl stehen, oder R² und R³ zusammen für 1,4-Buta-1,3-dienylen stehen; oder
• – R¹ für Wasserstoff, Methyl oder Ethyl steht, einer der Reste R² oder R³ für eine Bindungsstelle zu der Linkergruppe steht und der verbleibende Rest R² oder R³ für Wasserstoff oder Methyl steht.

Particular preference is given to using 1,2,3-triazolium ions (IVr), (IVr ') or (IVr'') those in which

• R ^{1 is} a linking site to the linker group, R ² and R ^{3 are} independently hydrogen or methyl, or R ² and R ³ together are 1,4-buta-1,3-dienylene; or
• - R ^{1 is} hydrogen, methyl or ethyl, one of R ² or R ^{3 is} a binding site to the linker group and the remaining radical R ² or R ^{3 is} hydrogen or methyl.

• – R¹ für eine Bindungsstelle zu der Linkergruppe steht und R² bis R⁹ unabhängig voneinander für Wasserstoff oder Methyl stehen, oder
• – R¹ für Wasserstoff, Methyl, Ethyl oder Phenyl steht, einer der Reste R² bis R⁹ für eine Bindungsstelle zu der Linkergruppe steht und R² bis R⁹ unabhängig voneinander für Wasserstoff oder Methyl stehen.

Particularly preferred pyrrolidinium ions (IVs) are those in which

• - R ^{1 is} a linking site to the linker group and R ² to R ^{9 are} independently hydrogen or methyl, or
• - R ^{1 is} hydrogen, methyl, ethyl or phenyl, one of R ² to R ^{9 is} a binding site to the linker group and R ² to R ^{9 are} independently hydrogen or methyl.

• – einer der Reste R¹ oder R⁴ für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R⁴ für Wasserstoff, Methyl, Ethyl oder Phenyl steht und R², R³ und R⁵ bis R⁸ unabhängig für Wasserstoff oder Methyl stehen; oder
• – R¹ und R⁴ unabhängig voneinander für Wasserstoff, Methyl, Ethyl oder Phenyl stehen und einer der Reste R², R³ und R⁵ bis R⁸ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R², R³ und R⁵ bis R⁸ unabhängig für Wasserstoff oder Methyl stehen.

Particularly preferred imidazolidinium ions (IVt) are those in which

• - One of the radicals R ¹ or R ^{4 is} a binding site to the linker group, the remaining radical R ¹ or R ^{4 is} hydrogen, methyl, ethyl or phenyl and R ² , R ³ and R ⁵ to R ^{8 is} independently hydrogen or Methyl stand; or
• - R ¹ and R ^{4 are} independently hydrogen, methyl, ethyl or phenyl and one of R ² , R ³ and R ⁵ to R ^{8 is} a binding site to the linker group and the remaining radicals R ² , R ³ and R ⁵ to R ^{8 are} independently hydrogen or methyl.

• – einer der Reste R¹ bis R³ für eine Bindungsstelle zu der Linkergruppe steht, die verbleibenden Reste R¹ bis R³ unabhängig voneinander für C₁- bis C₁₈-Alkyl stehen, oder
• – R¹ und R² zusammen für 1,5-Pentylen oder 3-Oxa-1,5-pentylen stehen und R³ für eine Bindungsstelle zu der Linkergruppe steht.

Particular preference is given to ammonium ions (IVu) as those in which

• - One of the radicals R ¹ to R ^{3 is} a binding site to the linker group, the remaining radicals R ¹ to R ^{3 are} independently C ₁ - to C ₁₈ -alkyl, or
• - R ¹ and R ² together represent 1,5-pentylene or 3-oxa-1,5-pentylene and R ^{3 represents} a point of attachment to the linker group.

Examples for the tertiary amines, of which the quaternary Ammonium ions of the general formula (IVu) by quaternization with the remainder R derived and having a free valence, are diethyl-n-butylamine, diethyl-tert-butylamine, diethyl-n-pentylamine, Diethylhexylamine, diethyloctylamine, diethyl (2-ethylhexyl) -amine, Di-n-propylbutylamine, di-n-propyl-n-pentylamine, di-n-propylhexylamine, Di-n-propyloctylamine, di-n-propyl- (2-ethylhexyl) -amine, diisopropylethylamine, Di-isopropyl-n-propylamine, di-isopropyl-butylamine, diisopropylpentylamine, Diisopropylhexylamine, diisopropyloctylamine, di-isopropyl- (2-ethylhexyl) -amine, di-n-butylethylamine, Di-n-butyl-n-propylamine, di-n-butyl-n-pentylamine, di-n-butylhexylamine, Di-n-butyloctylamine, di-n-butyl (2-ethylhexyl) amine, N-n-butylpyrrolidine, N-sec-butylpyrrodidine, N-tert-butylpyrrolidine, N-n-pentylpyrrolidine, N, N-dimethylcyclohexylamine, N, N-diethylcyclohexylamine, N, N-di-n-butylcyclohexylamine, N-n-propylpiperidine, N-isopropylpiperidine, N-n-butylpiperidine, N-sec-butylpiperidine, N-tert-butylpiperidine, N-n-pentylpiperidine, N-n-butylmorpholine, N-sec-butylmorpholine, N-tert-butylmorpholine, N-n-pentylmorpholine, N-benzyl-N-ethylaniline, N-benzyl-N-n-propylaniline, N-benzyl-N-isopropylaniline, N-benzyl-N-n-butylaniline, N, N-dimethyl-p-toluidine, N, N-diethyl-p-toluidine, N, N-di-n-butyl-p-toluidine, diethylbenzylamine, Di-n-propylbenzylamine, di-n-butylbenzylamine, diethylphenylamine, Di-n-propylphenylamine and di-n-butylphenylamine.

preferred tertiary amines (IVu) are di-isopropylethylamine, diethyl-tert-butylamine, Di-iso-propylbutylamine, di-n-butyl-n-pentylamine, N, N-di-n-butylcyclohexylamine and tertiary amines of pentyl isomers.

Especially preferred tertiary amines are di-n-butyl-n-pentylamine and tertiary amines of pentyl isomers. Another preferred tertiary amine having three identical residues is Triallylamine.

• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht, der verbleibende Rest R¹ oder R² für Methyl, Ethyl, 1-Butyl oder 1-Octyl steht und R³ für Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH oder -PO(OH)₂ steht, oder
• – R¹ für eine Bindungsstelle zu der Linkergruppe steht, R² eine -CH₂-CH₂-OR⁴-Gruppe ist und R³ und R⁴ unabhängig voneinander für Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH oder -PO(OH)₂ stehen.

Particular preference is given to using as cholinium ions (IVv) those in which

• One of the radicals R ¹ or R ^{2 is} a binding site to the linker group, the remaining radical R ¹ or R ^{2 is} methyl, ethyl, 1-butyl or 1-octyl and R ^{3 is} hydrogen, methyl, ethyl, acetyl, -SO ₂ OH or -PO (OH) ₂ , or
• - R ^{1 is} a linking site to the linker group, R ^{2 is} a -CH ₂ -CH ₂ -OR ⁴ group and R ³ and R ^{4 are} independently hydrogen, methyl, ethyl, acetyl, -SO ₂ OH or -PO (OH) ₂ stand.

Particularly preferred cholinium ions (IVw) are those in which R ^{3 is} selected from hydrogen, methyl, ethyl, acetyl, 5-methoxy-3-oxa-pentyl, 8-methoxy-3,6-dioxo-octyl, 11-methoxy 3,6,9-trioxa-undecyl, 7-methoxy-4-oxa-heptyl, 11-methoxy-4,8-dioxa-undecyl, 15-methoxy-4,8,12-trioxa-pentadecyl, 9-methoxy 5-oxa-nonyl, 14-methoxy-5,10-oxa-tetradecyl, 5-ethoxy-3-oxa-pentyl, 8-ethoxy-3,6-dioxa-octyl, 11-ethoxy-3,6,9- trioxa undecyl, 7-ethoxy-4-oxa-heptyl, 11-ethoxy-4,8-dioxa-undecyl, 15-ethoxy-4,8,12-trioxa-pentadecyl, 9-ethoxy-5-oxa-nonyl or 14-ethoxy-5,10-oxa-tetradecyl.

Especially Preferably, the cations (IV.w) are derived from cations selected are among 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), and have a free valency on a ring atom.

• – einer der Reste R¹ bis R³ für eine Bindungsstelle zu der Linkergruppe steht und die verbleibenden Reste R¹ bis R³ unabhängig voneinander für C₁-C₁₈-Alkyl, insbesondere Butyl, Isobutyl, 1-Hexyl oder 1-Octyl, oder Phenyl, das unsubstituiert ist oder 1, 2, 3, 4 oder 5 Substituenten trägt, die unabhängig voneinander unter C₁-C₁₈-Alkyl, Carboxylat, Sulfonat, COOH und SO₃H ausgewählt sind

Particularly preferred phosphonium ions (IVy) are those in which

• - One of the radicals R ¹ to R ^{3 is} a binding site to the linker group and the remaining radicals R ¹ to R ^{3 are} independently C ₁ -C ₁₈ alkyl, in particular butyl, isobutyl, 1-hexyl or 1-octyl, or Phenyl which is unsubstituted or carries 1, 2, 3, 4 or 5 substituents which are independently selected from C ₁ -C ₁₈ alkyl, carboxylate, sulfonate, COOH and SO ₃ H.

• – einer der Reste R¹ oder R² für eine Bindungsstelle zu der Linkergruppe steht und der verbleibende Rest R¹ oder R² unabhängig voneinander für C₁-C₁₈-Alkyl, insbesondere Butyl, Isobutyl, 1-Hexyl oder 1-Octyl, stehtn.

Particularly preferred sulfonium ions (IVz) are those in which

• - One of the radicals R ¹ or R ^{2 is} a binding site to the linker group and the remaining radical R ¹ or R ^{2 is} independently C ₁ -C ₁₈ alkyl, in particular butyl, isobutyl, 1-hexyl or 1-octyl, standn ,

Under the above heterocyclic cations with a free Valence on a ring atom are the imidazolium ions, imidazolinium ions, Pyridiniumionen, Py razoliniumionen and pyrazolium ions are preferred. Particularly preferred are the imidazolium ions and cations of DBU and DBN.

When Anions are in principle all monatomic anions or polyatomic Anions, d. H. polyatomic anions (anions with two or more than two atoms), can be used.

The Linkage to the linker group (s) can in principle via a covalent bond between a polyatomic anion and the Linkergrupe done.

der Gruppe der Methide der allgemeinen Formel:

der Gruppe der Alkoxide und Aryloxide der allgemeinen Formel R^cO^–; der Gruppe der Hydrogensulfide, Polysulfide, Hydrogenpolysulfide und Thiolate der allgemeinen Formeln:
HS^–, [S_v]^2–, [HS_v]^–, [R^cS]^–,
wobei v eine ganze positive Zahl von 2 bis 10 ist.The anion [Y] ^{n of} the ionic liquid is for example selected from
the group of halides, pseudohalides and halogen-containing compounds of the formulas:
F ^- , Cl ^- , Br ^- , I ^- , BF ₄ ^- , PF ₆ ^- , AsF ₆ ^- , SbF ₆ ^- , SiF ₆ ^2- , ClO ₄ ^- , CF ₃ SO ₃ ^- , (CF ₃ SO ₃ ) ₂ N ^- , CF ₃ CO ₂ ^- , CCl ₃ CO ₂ ^- , CN ^- , SCN ^- , OCN ^- ;
the group of sulfates, sulfites and sulfonates of the general formulas:
SO ₄ ^2- , HSO ₄ ^- , SO ₃ ^2- , HSO ₃ ^- , R ^c OSO ₃ ^- , R ^c SO ₃ ^- ;
Nitrates: NO ₃ ^- ;
the group of phosphates of the general formulas:
PO ₄ ^3- , HPO ₄ ^2- , H ₂ PO ₄ ^- , R ^c PO ₄ ^2- , HR ^c PO ₄ ^- , R ^c R ^d PO ₄ ^- ;
the group of phosphonates and phosphinates of the general formulas:
R ^c HPO ₃ ^- , R ^c R ^d PO ₂ ^- , R ^c R ^d PO ₃ ^- ;
the group of phosphites of the general formulas:
PO ₃ ^3- , HPO ₃ ^2- , H ² PO ₃ ^- , R ^c PO ₃ ^2- , R ^c HPO ₃ ^- , R ^c R ^d PO ₃ ^- ;
the group of phosphonites and phosphinites of the general formulas:
R ^c R ^d PO ₂ ^- , R ^c HPO ₂ ^- , R ^c R ^d PO ^- , R ^c HPO ^- ;
Antimonates: SbO ₂ ^2- , SbO ₄ ^3- ;
the group of carboxylic acids of the general formula:
R ^c COO ^- ;
Anions of hydroxycarboxylic acids and sugar acids;
Saccharinates (salts of o-benzoic acid sulfimide);
the group of the bristles of the general formulas:
B (R ^c ) ₄ ^- , BO ₃ ^3- , HBO ₃ ^2- , H ₂ BO ₃ ^- , R ^c R ^d BO ₃ ^- , R ^c BO ₃ ^2- , R ^c BO ₃ ^2- , B (OR ^c ) (OR ^d ) (OR ^e ) (OR ^f ) ^- , B (HSO ₄ ) ₄ ^- , B (R ^c SO ₄ ) ₄ ^- ;
the group of boronates of the general formulas:
R ^c BO ₂ ^2- , R ^c R ^d BO ^- ;
the group of carbides:
C ^4- (methanide), C ₂ ^2- (acetylide), C ₃ ^4- (allenid);
the group of carbonates and carbonic esters of the general formulas:
HCO ₃ ^- , CO ₃ ^2- , R ^c CO ₃ ^- ;
the group of silicates and silicic acid esters of the general formulas:
SiO ₄ ^4- , HSiO ₄ ^3- , H ₂ SiO ₄ ^2- , H ₃ SiO ₄ ^- , R ^c SiO ₄ ^3- , R ^c R ^d SiO ₄ ^2- , R ^c R ^d R ^e SiO ₄ ^- , HR ^c SiO ₄ ^2- , H ₂ R ^c SiO ₄ ^- , HR ^c R ^d SiO ₄ ^- ;
the group of the alkyl or aryl silanolates of the general formulas:
R ^c SiO ₃ ^3-, R ^c R ^d SiO ₂ ^2-, R ^c R ^d R ^e SiO ^-, R ^c R ^d R ^e SiO ₃ ^-, R ^c R ^d R ^e SiO ₃ ^-, R ^c R ^d SiO ₃ ^2- ;
the group of carboximides, bis (sulfonyl) imides and sulfonylimides of the general formula:

the group of methides of the general formula:

the group of alkoxides and aryloxides of the general formula R ^c O ^- ; the group of hydrogen sulfides, polysulfides, hydrogen polysulfides and thiolates of the general formulas:
HS ^- , [S _v ] ^2- , [HS _v ] ^- , [R ^c S] ^- ,
where v is a whole positive number from 2 to 10.

• – Wasserstoff;
• – Alkyl, vorzugsweise C₁-C₃₀-Alkyl, besonders bevorzugt C₁-C₁₈-Alkyl, das unsubstituiert ist, oder wie eingangs definiert, substituiert ist, und/oder, wie eingangs definiert, durch wenigstens ein Heteroatom oder heteroatomhaltige Gruppe unterbrochen sein kann;
• – Aryl, vorzugsweise C₆-C₁₄-Aryl, besonders bevorzugt C₆-C₁₀-Aryl, das unsubstituiert ist, oder wie eingangs definiert, substituiert ist;
• – Cycloalkyl, vorzugsweise C₅-C₁₂-Cycloalkyl, das unsubstituiert ist, oder wie eingangs definiert, substituiert ist;
• – Heterocycloalkyl, vorzugsweise Heterocycloalkyl mit 5 oder 6 Ringatomen, wobei der Ring neben Kohlenstoffringatomen 1, 2 oder 3 Heteroatome oder heteroatomhaltige Gruppen aufweist, das unsubstituiert ist, oder wie eingangs definiert, substituiert ist;
• – Heteroaryl, vorzugsweise Heteroaryl mit 5 bis 10 Ringatomen, wobei der Ring neben Kohlenstoffringatomen 1, 2 oder 3 Heteroatome oder heteroatomhaltige Gruppen aufweist, die ausgewählt sind unter Sauerstoff, Stickstoff, Schwefel und NR^a, das unsubstituiert ist, oder wie eingangs definiert, substituiert ist; wobei in Anionen, die mehrere Reste R^c bis R^f aufweisen, auch jeweils zwei dieser Reste zusammen mit dem Teil des Anions, an das sie gebunden sind, für wenigstens einen gesättigten, ungesättigten oder aromatischen Ring oder ein Ringsystem mit 1 bis 12 Kohlenstoffatomen stehen können, wobei der Ring oder das Ringsystem 1 bis 5 nicht benachbarte Heteroatome oder heteroatomhaltige Gruppen aufweisen kann, die vorzugsweise ausgewählt sind unter Sauerstoff, Stickstoff, Schwefel und NR^a, und wobei der Ring oder das Ringsystem unsubstituiert ist oder substituierten sein kann; wobei wenigstens einer der Reste, vorzugsweise einer der Reste, R^e, R^d, R^e und R^f für eine Bindungsstelle an die Linkergruppe stehen kann.

The radicals R ^c , R ^d , R ^e and R ^f are preferably each independently

• - hydrogen;
• - Alkyl, preferably C ₁ -C ₃₀ -alkyl, more preferably C ₁ -C ₁₈ -alkyl, which is unsubstituted, or as defined above, is substituted, and / or, as defined above, interrupted by at least one heteroatom or heteroatom-containing group can be;
• - Aryl, preferably C ₆ -C ₁₄ -aryl, more preferably C ₆ -C ₁₀ -aryl, which is unsubstituted, or as defined above, is substituted;
• - Cycloalkyl, preferably C ₅ -C ₁₂ -cycloalkyl, which is unsubstituted, or as defined above, is substituted;
• - Heterocycloalkyl, preferably heterocycloalkyl having 5 or 6 ring atoms, wherein the ring in addition to carbon ring atoms 1, 2 or 3 heteroatoms or heteroatom-containing groups which is unsubstituted, or as defined above, is substituted;
• - Heteroaryl, preferably heteroaryl having 5 to 10 ring atoms, wherein the ring in addition to carbon ring atoms 1, 2 or 3 heteroatom or heteroatom-containing groups which are selected from oxygen, nitrogen, sulfur and NR ^a , which is unsubstituted, or as defined above, substituted is; wherein in anions which have a plurality of radicals R ^c to R ^f , in each case two of these radicals together with the part of the anion to which they are attached represent at least one saturated, unsaturated or aromatic ring or a ring system having 1 to 12 carbon atoms wherein the ring or ring system may have from 1 to 5 non-adjacent heteroatoms or heteroatom-containing groups, preferably selected from oxygen, nitrogen, sulfur and NR ^a , and wherein the ring or ring system may be unsubstituted or substituted; wherein at least one of the radicals, preferably one of the radicals R ^e , R ^d , R ^e and R ^{f may represent} a binding site to the linker group.

With regard to suitable and preferred C ₁ -C ₃₀ -alkyls, in particular C ₁ -C ₁₈ -alkyls, C ₆ -C ₁₄ -aryls, in particular C ₆ -C ₁₀ -aryls, C ₅ -C ₁₂ -cycloalkyls, heterocycloalkyls with 5 or 6 ring atoms and heteroaryls with 5 or 6 ring atoms are referred to the introductory remarks. With regard to suitable and preferred substituents on C ₁ -C ₃₀ -alkyl, especially C ₁ -C ₁₅ -alkyl, C ₆ -C ₁₄ -aryl, C ₅ -C ₁₂ -cycloalkyl, heterocycloalkyl having 5 or 6 ring atoms and heteroaryl with 5 or 6 ring atoms is also referred to the statements made at the outset to substituents.

If at least one of the radicals R ^c to R ^{f is} optionally substituted C ₁ -C ₁₈ -alkyl, then it is preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, Hexyl, heptyl, Octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, decyl, dodecyl, tetradecyl, heptadecyl, octadecyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,1,3,3-tetramethylbutyl, benzyl, 1 Phenylethyl, a, a-dimethylbenzyl, benzhydryl, p-tolylmethyl, 1- (p-butylphenyl) -ethyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2-di- (methoxycarbonyl) -ethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, diethoxymethyl, diethoxyethyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-isopropoxyethyl, 2-butoxypropyl, 2-octyloxyethyl, Chloromethyl, trichloromethyl, trifluoromethyl, 1,1-dimethyl-2-chloroethyl, 2-methoxyisopropyl, 2-ethoxyethyl, butylthiomethyl, 2-dodecylthioethyl, 2-phenylthioethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2-aminoethyl, 2-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-M ethylaminoethyl, 2-methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2-dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethylaminobutyl, 6-dimethylaminohexyl, 2-hydroxy-2,2-dimethylethyl, 2- Phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl or 6-ethoxyhexyl.

If at least one of R ^e to R ^{f is} C ₁ -C ₁₈ -alkyl interrupted by one or more non-adjacent heteroatoms or heteroatom-containing groups, it is preferably 5-hydroxy-3-oxapentyl, 8-hydroxy-3,6 dioxaoctyl, 11-hydroxy-3,6,9-trioxa-undecyl, 7-hydroxy-4-oxa-heptyl, 11-hydroxy-4,8-dioxaundecyl, 15-hydroxy-4,8,12-trioxa-pentadecyl , 9-hydroxy-5-oxa-nonyl, 14-hydroxy-5,10-oxa-tetradecyl, 5-methoxy-3-oxa-pentyl, 8-methoxy-3,6-dioxo-octyl, 11-methoxy-3 , 6,9-trioxa undecyl, 7-methoxy-4-oxa-heptyl, 11-methoxy-4,8-dioxa-undecyl, 15-methoxy-4,8,12-trioxa-pentadecyl, 9-methoxy-5 -oxa-nonyl, 14-methoxy-5,10-oxatetradecyl, 5-ethoxy-3-oxa-pentyl, 8-ethoxy-3,6-dioxa-octyl, 11-ethoxy-3,6,9-trioxaundecyl, 7 Ethoxy-4-oxaheptyl, 11-ethoxy-4,8-dioxa-undecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxa-nonyl or 14-ethoxy-5,10 oxa-tetradecyl.

If two radicals R ^c to R ^{f form} a ring, these radicals can be taken together, for example, as fused building blocks 1,3-propylene, 1,4-butylene, 2-oxa-1,3-propylene, 1-oxa-1,3- propylene, 2-oxa-1,3-propenylene, 1-aza-1,3-propenylene, 1-C ₁ -C ₄ -alkyl-1-aza-1,3-propenylene, 1,4-buta-1, 3-dienylene, 1-aza-1,4-buta-1,3-dienylene or 2-aza-1,4-buta-1,3-dienylene.

The number of non-adjacent heteroatoms or heteroatom-containing groups of the radicals R ^c to R ^f is basically not critical and is usually limited only by the size of the respective residue or ring building block. As a rule, it is not more than 5 in the respective radical, preferably not more than 4 or very particularly preferably not more than 3. Furthermore, at least one, preferably at least two, carbon atoms are generally present between two heteroatoms.

substituted and unsubstituted imino groups may be, for example Imino, methylimino, iso-propylimino, n-butylimino or tert-butylimino be.

Preferred functional groups of the radicals R ^c to R ^f are carboxy, carboxamide, hydroxy, di- (C ₁ -C ₄ -alkyl) -amino, C ₁ -C ₄ -alkyloxycarbonyl, cyano or C ₁ -C ₄ -alkoxy. Radicals R ^c to R ^f other than alkyl can also be monosubstituted or polysubstituted by C ₁ -C ₄ -alkyl, preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

If at least one of the radicals R ^c to R ^{f is} optionally substituted C ₆ -C ₁₄ -aryl, then it is preferably phenyl, methylphenyl (tolyl), xylyl, α-naphthyl, β-naphthyl, chlorophenyl, dichlorophenyl, trichlorophenyl, Dichlorophenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, iso-propylphenyl, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl , 2,6-dimethoxyphenyl, 2,6-dichlorophenyl, 4-bromophenyl, 2- or 4-nitrophenyl, 2,4- or 2,6-dinitrophenyl, 4-dimethylaminophenyl, 4-acetylphenyl, methoxyethylphenyl or ethoxymethylphenyl.

If at least one of the radicals R ^c to R ^{f is} optionally substituted C ₅ -C ₁₂ -cycloalkyl, it preferably represents cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl , Diethoxycyclohexyl, Butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl or for a saturated or unsaturated bicyclic system such as norbornyl or norbornenyl.

When at least one of R ^c to R ^{f is} an optionally substituted five or six is lower heterocycle, it preferably stands for furyl, thienyl, pyryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxy, benzimidazolyl, benzothiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyryl, methoxifuryl, dimethoxypyridyl, difluoropyridyl, methylthiophenyl, isopropylthiophenyl or tert-butylthiophenyl.

When in anions which have a plurality of radicals R ^c to R ^f , in each case two of these radicals together with the part of the anion to which they are attached represent at least one saturated, unsaturated or aromatic ring or a ring system having 1 to 12 carbon atoms where the ring or the ring system may have 1 to 5 non-adjacent heteroatoms or heteroatom-containing groups which are preferably selected from oxygen, nitrogen, sulfur and NR ^a , the ring or the ring system is unsubstituted or carries 1, 2, 3, 4, 5 or more than 5 substituents. The substituents are preferably independently selected from alkyl, alkoxy, alkylsulfanyl, cycloalkyl, cycloalkoxy, polycyclyl, heterocycloalkyl, aryl, aryloxy, arylthio and heteroaryl.

Preferred anions are, for example, selected from the group of halides and pseudohalides and halogen-containing compounds, the group of sulfates, sulfites and sulfonates, the group of phosphates, the group of phosphonates and phosphinates, the group of carboxylic acids, the group of bristles, antimonates, fluorosilicates , Nitrate, for example CF ₃ SO ₃ ^- . PF ₆ ^- , B (C ₆ H ₅ ) ₄ ^- , Cl ^- .

Preferably, in the compounds of formula (I), the linker is a chemical bond, usually a covalent bond, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-S-, -S-CO-, -CO-N (R ^a ) -, -N (R ^a ) -CO-, -N (R ^a ) -CO-O-, -O-CO-N (R ^a ) -, -N (R ^a ) -CO-N (R ^a ) -, -CH ₂ -O-, -O-CH ₂ -, or an (n + m) valent C ₁ -C ₅₀ - Hydrocarbon radical which is represented by -O-, -S-, -NR ^a -, -PR ^a -, -SiR ^a R ^aa and / or -SO ₂ - one or more times, for. B. single, double, triple, quadruple or more than four times, may be interrupted. R ^a is preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. R ^aa is preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl or aryl. The (n + m) -valent C ₁ -C ₅₀ hydrocarbon radical is derived formally by abstraction of n + m H atoms from the corresponding parent compound.

Preferably, in the compounds of formulas (II) and (III), the linker is a chemical bond, usually a covalent bond, -O-, -S-, -CO-O-, -O-CO-, -O-CO -O-, -CO-S-, -S-CO-, -CO-N (R ^a ) -, -N (R ^a ) -CO-, -N (R ^a ) -CO-O-, -O -CO-N (R ^a ) -, -N (R ^a ) -CO-N (R ^a ) -, -CH ₂ -O-, -O-CH ₂ - or a divalent C ₁ -C ₅₀ -hydrocarbon radical, by -O-, -S-, -NR ^a -, -PR ^a -, SiR ^a R ^aa and / or -SO ₂ - one or more times, z. B. single, double, triple, quadruple or more than four times, may be interrupted. R ^a and R ^aa have the meanings given above. The divalent C ₁ -C ₅₀ hydrocarbon radical is derived formally by abstraction of two H atoms from the corresponding parent compound.

Examples of divalent linkers include aliphatic, cycloaliphatic, aromatic, heteroaromatic, araliphatic, aliphatic-araliphatic, cycloaliphatic, aliphatic-cycloaliphatic radicals having 1 to 50 C atoms, -O-, -S-, -CO-O-, -O- CO, -O-CO-O-, -CO-S-, -S-CO-, -CO-N (R ^a ) -, -N (R ^a ) -CO-, N (R ^a ) -CO -O-, -O-CO-N (R ^a ) -, -N (R ^a ) -CO-N (R ^a ) -, -CH ₂ -O-, -O-CH ₂ -, wherein R ^{a is} the has previously mentioned meanings:
Suitable divalent linkers include:
C ₁ - to C ₃₀ -alkylene which is substituted by one or more nonadjacent groups selected from -O-, -S-, -NR ^a -, -C (= O) -, -S (= O) - , -S (= O) 2-, one or more times, e.g. B. may be interrupted once, twice, three times or more than three times. R ^a and R ^b are preferably independently of one another hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. C ₁ -C ₃₀ -alkylene can be simply up to several times, for. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, phenyl or C ₃ -C ₁₀ cycloalkyl be substituted.

C ₂ - to C ₃₀ -alkenediyl which is represented by one or more nonadjacent groups selected from -O-, -S-, -NR ^a -, -C (= O) -, -S (= O) - , -S (= O) ₂ -, one or more times, z. B. single, double, triple or more than three times, may be interrupted. R ^a and R ^b are preferably independently of one another hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. Depending on the number of chain lengths, alkenediyl may have one or more carbon-carbon double bonds. C ₂ -C ₃₀ -Alkendiyl can be simply up to several times, for. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, phenyl or C ₃ -C ₁₀ cycloalkyl be substituted.

C ₂ - to C ₃₀ -alkenyl which is substituted by one or more non-adjacent groups selected from -O-, -S-, -NR ^a -, -C (= O) -, -S (= O) - , -S (= O) ₂ -, one or more times, z. B. single, double, triple or more than three times, may be interrupted. R ^a and R ^b are preferably independently of one another hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl. Depending on the chain length, alkynediyl may have one or more carbon-carbon triple bonds. C ₂ -C ₃₀ -alkanol may be monosubstituted to polyunsaturated, e.g. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, phenyl or C ₃ -C ₁₀ cycloalkyl be substituted.

Arylene, for example, phenylene such as 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, naphthylene, for example, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene and the like. The arylene group can be simply up to several times, for. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkoxy be substituted cycloalkanediyl, z. B. C ₃ -C ₃₀ cycloalkanediyl, which can be monosubstituted to polyunsaturated, e.g. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Arylene-alkylene, z. For example, C ₆ -C ₁₈ -arylene-C ₁ -C ₁₂ -alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Alkylene-arylene-alkylene, e.g. B. C ₆ -C ₁₈ alkylene-C ₆ -C ₁₈ -arylene-C ₁ -C ₁₂ alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Arylene-alkylene, z. For example, C ₆ -C ₁₈ -arylene-C ₁ -C ₁₂ -alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Alkylene-arylene-alkylene, e.g. B. C ₁ -C ₁₂ alkylene-C ₆ -C ₁₈ -arylene-C ₁ -C ₁₂ alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Cycloalkylene-alkylene, e.g. B. C ₃ -C ₂₀ cycloalkylene-C ₁ -C ₁₂ alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Alkylene-cycloalkylene-alkylene, z. B. C ₁ -C ₁₂ alkylene-C ₃ -C ₂₀ cycloalkylene-C ₁ -C ₁₂ alkylene, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Heterocyclylene, e.g. B. heterocyclylene having 4 to 10 ring members, containing in addition to carbon ring atoms one, two, three or four selected from O, S and N heteroatoms as ring members, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

Heterocyclyl-C ₁ -C ₁₂ alkylene, wherein heterocycles z. B. 4 to 10 ring members, containing in addition to carbon ring atoms one, two, three or four selected from O, S and N heteroatoms as ring members, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

C ₁ -C ₁₂ alkylene-heterocyclylene C ₁ -C ₁₂ alkylene, e.g. B. heterocycles having 4 to 10 ring members, containing in addition to carbon ring atoms one, two, three or four selected from O, S and N heteroatoms as ring members, the simple to multiply, z. B. one, two, three, four times or more than four times, same or different by fluorine, chlorine, bromine, cyano, OH, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

In particular, the divalent linker is linear C ₂ -C ₃₀ alkylene, wherein one or more, e.g. B. 1, 2, 3, 4, 5 or 6 CH ₂ groups independently of each other by O-, -S-, -CO-O-, O-CO-, -O-CO-O-, -CO-S -, -S-CO-, -CO-N (R ^a ) -, -N (R ^a ) -CO-, -N (R ^a ) -CO-O-, O CO-N (R ^a ) - or -N (R ^a ) -CO-N (R ^a ) -, phenylene or C ₃ -C ₁₀ -cycloalkanediyl may be replaced, these interrupting groups may not be adjacent; wherein alkylene may be substituted by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkyl, phenyl or C ₃ -C ₁₀ cycloalkyl; wherein R ^{a is} hydrogen or C ₁ -C ₄ alkyl;

worin
R¹¹ bis R¹⁴ unabhängig voneinander für Wasserstoff, oder jeweils unsubstituiertes oder substituiertes Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl oder Hetaryl stehen, wobei die vier letztgenannten jeweils auch Teil eines kondensierten Ringsystems sein können, mit der Maßgabe, dass wenigstens einer der Reste R¹¹ bis R¹⁴ für eine Bindungsstelle zu einem Linker steht.In a suitable embodiment, the group HTM is selected from groups of the general formula (V)

wherein
R ¹¹ to R ¹⁴ independently of one another are hydrogen, or in each case unsubstituted or substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, where the four latter can each also be part of a fused ring system, with the proviso that at least one of the radicals R ¹¹ until R ^{14 is} a linker to a linker.

worin
* für eine Bindungsstelle zu einem Linker steht,
R²⁰ und R²¹ unabhängig voneinander für jeweils unsubstituiertes oder substituiertes Cycloalkyl, Heterocycloalkyl, Aryl oder Hetaryl stehen, die jeweils auch Teil eines kondensierten Ringsystems sein können.In a further suitable embodiment, the group HTM is selected from groups of the general formula (VI)

wherein
* represents a binding site to a linker,
R ²⁰ and R ²¹ independently of one another each represent unsubstituted or substituted cycloalkyl, heterocycloalkyl, aryl or hetaryl, each of which may also be part of a fused ring system.

worin
# für die Bindungsstelle zum Stickstoffatom steht,
die Reste R^h jeweils unabhängig voneinander ausgewählt sind unter C₁-C₆-Alkyl, C₁-C₆-Alkoxy, C₁-C₆-Alkylthio, Fluor, Chlor, Brom, NE⁵E⁶, Nitro und Cyano, wobei E⁵ und E⁶ unabhängig voneinander für Wasserstoff, Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl oder Hetaryl stehen,
x in der Formel 5 für 1, 2, 3, 4 oder 5 steht,
in der Formel 6 für 1, 2, 3 oder 4 steht,
in der Formel 7 für 1, 2 oder 3 steht,
in der Formel 8 für 1 oder 2 steht.R ²⁰ and R ²¹ are preferably selected from groups of the general formulas (1) to (8)

wherein
# represents the binding site to the nitrogen atom,
the radicals R ^{h are} each independently selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, fluorine, chlorine, bromine, NE ⁵ E ⁶ , nitro and cyano, wherein E ⁵ and E ⁶ independently of one another represent hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl,
x in formula 5 is 1, 2, 3, 4 or 5,
in formula 6 is 1, 2, 3 or 4,
in formula 7 is 1, 2 or 3,
in formula 8 stands for 1 or 2.

worin # für die Bindungsstelle zum Stickstoffatom steht.Preferably, R ²⁰ and R ^{21 are} both

where # is the binding site to the nitrogen atom.

The Compounds of the invention are particularly suitable advantageous for use in solar cells, especially in dye-sensitized solar cells. They serve in particular as hole conductor material (p-type semiconductor).

Preferably In solar cells, compounds with a melting point in the range from about 40 to 200 ° C, more preferably from 60 to 180 ° C, especially from 80 to 120 ° C, used. The melting point is chosen so that the salts in the work area the solar cell are solid. For outdoor applications amounts therefore, the melting point of the compounds is preferably at least 80 ° C.

preferred Anions of the salts for use in solar cells are for example, selected from the group of pseudohalides and halogen-containing compounds, the group of sulfates, sulfites and sulfonates, the group of phosphates, the group of phosphonates and phosphinates, the group of carboxylic acids, the group bristle, antimonates, fluorosilicates, nitrate.

Particularly preferred anions are SO ^{4 2-} , R ^c OSO ₃ ^- , R ^c SO ₃ ^- , CF ₃ SO ₃ ^- , C ⁴ , R ^c COO ^- , B (R ^c ) ₄ ^- , SCN ^- , OCN ^- , BF ₄ ^- , PF ₆ ^- , AsF ₆ ^- , SbF ₆ ^- , SiF ₆ ^2- , ClO ₄ , NO ₃ ^- , wherein R ^{c is} preferably hydrogen, alkyl or aryl.

Preferred carboxylates R ^c COO- are formate, acetate, propionate and butyrate.

Preferred as B (R ^c ) ₄ ^- is B (C ₆ H ₅ ) ₄ ^- .

• – ein zumindest teilweise lichtdurchlässiges Substrat,
• – eine erste Elektrode (Frontelektrode)
• – gegebenenfalls wenigstens eine Pufferschicht,
• – eine mit einem Farbstoff sensibilisierte Schicht eines n-Halbleiters,
• – eine Schicht mit wenigstens einem p-Halbleiter,
• – eine zweite Elektrode (Rückelektrode)

Dye-sensitized solar cells are also referred to as dye solar cells (DSC). Their structure is known in principle and z. B. from M. Grätzel in J. Photochem. Photobio. C: Photochemistry Reviews 4, 2003 pages 145-153 such as Chiba et al., Japanese Journal of Appl. Phys., 2006, 45, L638-L640 The structure of a dye-sensitized solar cell usually comprises the following components:

• An at least partially transparent substrate,
• A first electrode (front electrode)
• Optionally at least one buffer layer,
• A dye sensitized layer of an n-type semiconductor,
• A layer with at least one p-type semiconductor,
• A second electrode (return electrode)

The structure of a typical dye-sensitized solar cell is often based on a glass substrate which is coated with a transparent, conductive layer, the working electrode. On this electrode or in the vicinity of the same usually an n-type metal oxide is applied, for example, an approximately 10-20 microns thick, nanoporous layer of titanium dioxide (TiO ₂ ). On its surface, in turn, usually a monolayer of a light-sensitive dye (for example, a ruthenium complex) is adsorbed, which can be converted by light absorption in an excited state. On or at the counter electrode is often a few microns thick catalytic layer, such as platinum. The area between the two electrodes is z. B. with a redox electrolyte, such as a solution of iodine (I ₂ ) and lithium iodide (LiI) filled. The function of the dye solar cell is based on the fact that light is absorbed by the dye. From the excited dye, electrons are transferred to the n-type semiconducting metal oxide semiconductor and migrate therefrom to the anode, whereas the electrolyte provides for charge balance across the cathode.

First electrode and n-type semiconductor

As the n-type semiconductor, at least one n-type semiconductive metal oxide is generally used. As the n-type semiconducting metal oxide of the dye solar cell, a single metal oxide or a mixture of various oxides may be used. It is also possible to use mixed oxides. The n-semiconducting metal oxide can be used in particular as a nanoparticulate oxide, wherein nanoparticles in this Zusam Particles are understood to mean having an average particle size of less than 0.1 microns.

One Nanoparticulate oxide is usually by a sintering process as a thin porous film with large Surface onto a conductive substrate (i.e. a carrier with a conductive layer as the first Electrode) applied.

When Substrate (hereinafter also referred to as support) are suitable in addition to metal foils especially plastic sheets or films and especially glass plates. As electrode material, in particular for the first electrode according to the above-described, preferred structure, are particularly conductive Materials such. B. transparent conductive oxides (Transparent Conducting oxides, TCO), for example with fluorine and / or indium doped tin oxide (FTO or ITO) and / or aluminum-doped zinc oxide (AZO), carbon nanotubes or metal films. alternative or in addition, however, could also thin Metal films that still have sufficient transparency used become. The substrate can work with these conductive materials be occupied or coated.

There in the proposed construction usually only a single substrate is needed, the construction of flexible cells is possible. This allows a variety of uses with rigid substrates would not be feasible such as the use in bank cards, garments Etc.

The first electrode, in particular the TCO layer, can additionally be coated or coated with a (for example 10 to 200 nm thick) solid buffer layer, in particular a metal oxide buffer layer, in order to direct contact of the p-type semiconductor with the TCO layer avoid (see Peng et al., Coord. Chem. Rev. 248, 1479 (2004) ). The buffer metal oxide which may be employed in the buffer layer may comprise, for example, one or more of the following materials: vanadium oxide; a zinc oxide; a tin oxide; a titanium oxide.

thin Layers or films of metal oxides are known usually inexpensive solid semiconductor materials (n-type semiconductors), however, their absorption is due to large Band gaps usually not in the visible range of the solar spectrum, but mostly in the ultraviolet spectral range. For the application in solar cells must therefore the metal oxides usually, as is the case with the dye-sensitized solar cells, be combined with a dye as a photosensitizer, the in the wavelength range of sunlight, ie at 300 to 2000 nm, absorbed and in electronically excited state electrons injected into the conduction band of the semiconductor. With the help of an additional used in the cell solid p-type semiconductor as the electrolyte, the in turn is reduced at the counter electrode, electrons can be attributed to the sensitizer, so that this is regenerated.

From are of particular interest for use in solar cells the semiconductors zinc oxide, tin dioxide, titanium dioxide or mixtures of these metal oxides. The metal oxides can be in the form of nanocrystalline porous layers are used. These layers have a large surface on that with the sensitizer is coated, allowing a high absorption of sunlight is reached. Metal oxide layers that are structured as z. As nanorods (nanorods), offer benefits such as higher Electron mobility or improved pore filling through the dye and the p-type semiconductor.

The Metal oxide semiconductors may be used alone or in the form of mixtures be used. It is also possible to use a metal oxide coat with one or more other metal oxides. Farther The metal oxides can also be used as a coating on one other semiconductors, e.g. As GaP, ZnP or ZnS, be applied.

Especially preferred semiconductors are zinc oxide and titanium dioxide in the anatase modification, which is preferably used in nanocrystalline form.

Furthermore the sensitizers can be advantageously used with all n-semiconductors, commonly used in these solar cells, be combined. As preferred examples are in ceramics Metal oxides used, such as titanium dioxide, zinc oxide, tin (IV) oxide, Tungsten (VI) oxide, tantalum (V) oxide, niobium (V) oxide, cesium oxide, strontium titanate, Zinc stannate, complex perovskite type oxides, e.g. Barium titanate, and binary and ternary iron oxides called the can also be present in nanocrystalline or amorphous form.

Due to the strong absorption exhibited by common organic dyes and phthalocyanines and porphyrins, even thin layers or films of the n-type semiconducting metal oxide are sufficient. to take up the required amount of dye. Thin metal oxide films in turn have the advantage that the probability of undesired recombination processes decreases and that the internal resistance of the dye subcell is reduced. For the n-semiconducting metal oxide, it is preferable to use layer thicknesses of from 100 nm to 20 micrometers, more preferably in the range between 500 nm to about 5 micrometers.

dye

Numerous dyes that can be used in the context of the present invention are known from the prior art, so that for possible material examples, reference may also be made to the above description of the prior art for dye-sensitized solar cells. All listed and claimed dyes may in principle also be present as pigments. Dye-sensitized solar cells based on titanium dioxide as a semiconductor material are, for. In US-A-4 927 721 , Nature 353, pp. 737-740 (1991) and US-A-5,350,644 and Nature 395, pp. 583-585 (1998) and EP-A-1 176 646 described. The dyes described in these documents can in principle also be used advantageously in the context of the present invention. These dye-sensitized solar cells contain monomolecular films of transition metal complexes, in particular ruthenium complexes, which are bonded to the titanium dioxide layer via acid groups as sensitizers.

Sensitizers, not least for reasons of cost, have repeatedly been proposed metal-free organic dyes which can also be used in the context of the present invention. High efficiencies of over 4%, in particular in solid dye-dye solar cells, can be achieved, for example, with indoline dyes (see, for example, US Pat. Schmidt-Blende et al., Adv. Mater. 2005, 17, 813 ). US-A-6,359,211 describes the use of cyanine, oxazine, thiazine and acridine dyes, which can also be used in the context of the present invention, which have carboxyl groups bonded via an alkylene radical for attachment to the titanium dioxide semiconductor.

In JP-A-10-189065 . 2000-243463 . 2001-093589 . 2000-100484 and 10-334954 Various perylene skeleton unsubstituted perylene-3,4: 9,10-tetracarboxylic acid derivatives for use in semiconductor solar cells are described. Specifically, they are: perylenetetracarboxylic diimides which carry carboxyalkyl, carboxyaryl, carboxyarylalkyl or carboxyalkylaryl radicals on the imide nitrogen atoms and / or are imidated with p-diaminobenzene derivatives in which the nitrogen atom of the amino group is substituted in the p-position by two further phenyl radicals or Part of a heteroaromatic tricyclic system; Perylene-3,4: 9,10-tetracarboxylic monoanhydride monoimides which carry on the imide nitrogen the above-mentioned radicals or non-functionalized alkyl or aryl radicals, or semicondensates of perylene-3,4,9,10-tetracarboxylic dianhydride with 1,2-diaminobenzenes or 1,8-diaminonaphthalenes, which are converted by further reaction with primary amine into the corresponding diimides or double condensates; Condensates of perylene-3,4,9,10-tetracarboxylic dianhydride with 1,2-diaminobenzenes functionalized by carboxyl or amino groups; and perylene-3,4: 9,10-tetracarboxylic diimides which are imidated with aliphatic or aromatic diamines.

In New J. Chem. 26, pp. 1155-1160 (2002) the sensitization of titanium dioxide with perylene derivatives is investigated, which are unsubstituted in the perylene skeleton (bay positions). Specifically mentioned are 9-dialkylaminoperylene-3,4-dicarboxylic acid anhydrides, perylene-3,4-dicarboxylic acid imides which are substituted in the 9-position by dialkylamino or carboxymethylamino and at the imide nitrogen atom carboxymethyl. a 2,5-di (tert-butyl) phenyl radical, and called N-dodecylaminoperylene-3,4: 9,10-tetracarboxylic monoanhydride monoimide. However, the liquid-electrolyte solar cells based on these perylene derivatives showed significantly lower efficiencies than a solar cell sensitized for comparison with a ruthenium complex.

Particularly preferred as Sensibilisatorfabstoffe in the proposed dye solar cell are those in DE 10 2005 053 995 A1 or WO 2007/054470 A1 described perylene derivatives, Terrylenderivate and Quaterrylenderivate. The use of these dyes leads to photovoltaic elements with high efficiencies and high stabilities.

The rylenes show strong absorption in the wavelength range of sunlight and can, depending on the length of the conjugated system, a range of about 400 nm (perylene derivatives I out DE 10 2005 053 995 A1 ) up to about 900 nm (quaterrylene derivatives I out DE 10 2005 053 995 A1 ) cover. Depending on their composition, terrylene-based rylene derivatives I absorb in a solid state adsorbed to titanium dioxide in a range from about 400 to 800 nm. In order to maximize the utilization of the incident sunlight from the visible to the near-infrared region, it is advantageous to use Mi shingles of various Rylenderivate I use. Occasionally, it may also be advisable to use different Rylenhomologe.

The rylene derivatives I can be easily and permanently fixed on the metal oxide film. Binding takes place via the anhydride function (x1) or the carboxyl groups -COOH or -COO- formed in situ or via the acid groups A contained in the imide or condensate radicals ((x2) or (x3)) DE 10 2005 053 995 A1 Rylene derivatives I described are well suited for use in dye-sensitized solar cells in the context of the present invention.

Especially it is preferred if the dyes are at one end of the molecule have an anchor group that their fixation on the n-type semiconductor film guaranteed. Included at the other end of the molecule the dyes preferably electron donors Y, which is the regeneration of the dye after electron donation to the n-type semiconductor and also the recombination with already to the semiconductor Prevent emitted electrons.

For further details on the possible selection of a suitable dye, for example, turn on DE 10 2005 053 995 A1 to get expelled. Ruthenium complexes, porphyrins, other organic sensitizers and preferably rylenes can be used in particular for the solid-colorant solar cells described herein.

The Fixation of the dyes on the metal oxide films can be easier Done way. For example, the n-semiconducting Metal oxide films in a freshly sintered (still warm) state a sufficient period of time (eg, about 0.5 to 24 hours) with a Solution or suspension of the dye in a suitable organic solvents are brought into contact. This For example, by immersing the coated with the metal oxide Substrate in the solution of the dye happen.

If combinations of different dyes are to be used, they can be applied, for example, one after the other from one or more solutions or suspensions containing one or more of the dyes. Also possible is the use of two dyes separated by a layer of z. B. CuSCN are (see, eg. Tennakone, KJ, Phys. Chem B. 2003, 107, 13758 ). The most appropriate method can be determined comparatively easily in individual cases.

in principle the dye may be present as a separate element or in one Separate step are applied and separated on the rest Layers are applied. Alternatively or additionally however, the dye also with one or more of the other elements be summarized or applied together, for example with the solid p-type semiconductor. For example, a dye-p-semiconductor combination which contains an absorbing dye with p-type semiconducting Properties include or, for example, a pigment with absorbent and p-semiconducting properties.

In order to prevent recombination of the electrons in the n-type semiconducting metal oxide with the solid p-type conductor, a kind of passivating layer comprising a passivation material may be used. This layer should be as thin as possible and, if possible, should only cover the hitherto uncovered areas of the n-semiconducting metal oxide. The passivation material may also be applied to the metal oxide in time before the dye. As passivation materials in particular the following substances are preferred: Al ₂ O ₃ ; an aluminum salt; Silanes, such as For example, CH ₃ SiCl ₃ ; an organometallic complex, in particular an Al ³⁺ complex; Al ³⁺ in particular an Al ³⁺ complex; 4-tert-butylpyridine (TBP); MgO; 4-guanidinobutyric acid (GBA); an alkyl acid; Hexadecylmalonic acid (HDMA).

p-type semiconductor

Of the comprises p-type semiconductor used according to the invention or consists of at least one connection, as previously defined.

As described above, the solid-dye solar cell employs solid p-type semiconductors. Solid p-type semiconductors can also be used in the dye-sensitized soot cells according to the invention without a large increase in cell resistance, in particular if the dyes absorb strongly and therefore require only thin n-type semiconductor layers. In particular, the p-type semiconductor should essentially have a closed, dense layer, so that undesired recombination reactions resulting from contact between the n-semiconductive metal oxide (in particular in nanoporous form) with the second electrode or second half cell could be reduced.

An essential parameter which influences the quality of the p-type semiconductor is the hole mobility, since this determines the hole diffusion length (cf. Kumara, G., Langmuir, 2002, 18, 10493-10495 ). Here, the compounds of the invention are characterized by good results.

Examples of additionally suitable solid p-type semiconductors are inorganic solids such as copper (I) iodide and copper (I) thiocyanate. However, preference is given to using organic (ie low molecular weight, oligomeric or polymeric semiconductors or mixtures of such semiconductors) semiconductors. Examples here are p-type semiconductors based on polymers such as polythiophene and polyarylamines, or of amorphous, reversibly oxidizable, nonpolymeric organic compounds, such as the spirobifluorenes mentioned in the beginning (cf. US 2006/0049397 and the spiro compounds disclosed herein as p-type semiconductors which are also useful in the present invention). These solid p-type semiconductors can be used in both undoped and doped form.

The Salts of the invention are also particularly suitable for use as ionic liquid.

she are preferably suitable as solvents for chemical reactions, as an aid in the separation of mixtures, as auxiliaries for the extractive rectification for separation dense or azeotropic mixtures, as heat transfer.

The use of ionic liquids as solvents for chemical reactions is described, for example, by Peter Wasserscheid, Chemistry in Our Time, 37 (2003) No. 1, pages 52-63 described. They can also serve as aids for the separation of acids from chemical reaction mixtures, as described, for example, in US Pat DE 102 02 838 , The salts according to the invention are furthermore suitable as auxiliary substances for the extractive rectification for the separation of close-boiling or azeotropic mixtures ( WO 02/074718 and WO 2004/090066 ). They are suitable as heat transfer, z. B. in solar thermal systems, such as described in Proceeding of Solar Forum, April 21-25, 2001, Washington DC The use of ionic liquids as extractants for the separation of substances is further described in JG Huddleston et al., Chem. Commun. 1998, pages 1765-1766 mentioned.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

Cited patent literature

• - DE 10202838 A1 [0067]
• US 4927721 A [0177]
• - US 5350644 A [0177]
• EP 1176646A [0177]
• - US 6359211 A [0178]
• - JP 10-189065 A [0179]
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• - JP 2001-093589 [0179]
• - JP 2000-100484 [0179]
• JP 10-334954 [0179]
• - DE 102005053995 A1 [0181, 0182, 0182, 0183, 0185]
• WO 2007/054470 A1 [0181]
• US 2006/0049397 [0193]
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• WO 02/074718 [0196]
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Cited non-patent literature

• KN Marsh et al., Fluid Phase Equilibria 219 (2004), 93-98 [0002]
• JG Huddleston et al., Green Chemistry 2001, 3, 156-164 [0002]
• - Angew. Chem. 2000, 112, pp. 3926-3945 [0068]
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• - Kumara, G., Langmuir, 2002, 18, 10493-10495 [0192]
• - Peter Wasserscheid, Chemistry in Our Time, 37 (2003) No. 1, pages 52-63 [0196]
• - Proceeding of Solar Forum, April 21-25 , 2001, Washington DC [0196]
• JG Huddleston et al., Chem. Commun. 1998, pages 1765-1766 [0196]

Claims (15)

Compound of the general formulas (I), (II) or (III)

wherein n is an integer of at least 1, m is an integer of at least 1, p is an integer of at least 2, q is an integer of at least 2, IL is a salt group containing at least one Cation and at least one anion, wherein at least one of the ions is organic, and wherein in the compounds of formulas (I) and (II) the salt groups IL may each have the same or different meanings and each have a point of attachment to the linker group, in the Compounds of the formula (III) the salt group IL q has binding sites to each of the linker group, linker in the compounds of the formula (I) is a chemical bond or an (n + m) valent organic radical which is preferably 1 to 50 C Having atoms and in the compounds of formulas (II) and (III) is a chemical bond or a bivalent organic radical, which preferably has 1 to 50 carbon atoms, HTM for as Lo conductor material (p-type semiconductor) capable group. Compound of the general formulas (I), (II) or (III) according to claim 1, which is at ambient pressure at a temperature is liquid below 200 ° C. Compound of the general formulas (I), (II) or (III) according to one of claims 1 or 2, which has a melting point in the range of about 40 to 200 ° C, preferably from 60 to 180 ° C, more preferably from 80 to 120 ° C, having. A compound according to any one of the preceding claims, wherein the group IL is selected from salt groups of the general formula (IV.A) [A ⁺ ] _n , [Y] ^n- (IV.A), where n is 1, 2, 3 or 4, [A ⁺ ] is a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and [Y] ^n- for a one-, two- or three-membered cation , tri- or tetravalent anion or mixtures of these anions; Mixed salt groups of the general formulas (IV.B) [A1 ⁺ ] [A2 ⁺ ] [Y] ^n- (IV.Ba), where n = 2, [A1 ⁺ ] [A2 ⁺ ] [A3] ⁺ [Y] ^n- (IV.Bb), where n = 3, [A1 ⁺ ] [A2 ⁺ ] [A3 ⁺ ] [A4 ⁺ ] [Y] ^n- (IV.Bc), where n = 4, and where [A1 ⁺ ], [A2 ⁺ ], [A3 ⁺ ] and [A4 ⁺ ] are independently selected from the groups mentioned for [A ⁺ ] and [Y] ^{n- has} the meaning given under formula (IV.A) ; or mixed salt groups of the general formulas (IV.C) [A1 ⁺ ] [A2 ⁺ ] [A3 ⁺ ] [M1 ⁺ ] [Y] ^n- (IV.Ca), where n = 4, [A1 ⁺ ] [A2 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] [Y] ^n- (IV.Cb), where n = 4, [A1 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] [M3 ⁺ ] [Y] ^n- (IV.Cc), where n = 4, [Al +] [A2 ⁺ ] [M1 ⁺ ] [Y] ^n- (IV.Cd), where n = 3, [A1 ⁺ ] [M1 ⁺ ] [M2 ⁺ ] [Y] ^n- (IV.Ce), where n = 3, [A1 ⁺ ] [M1 ⁺ ] [[Y] ^n- (IV.Cf), where n = 2, [A1 ⁺ ] [A2 ⁺ ] [M4 ²⁺ ] [Y] ^n- (IV.Cg), where n = 4, [A1 ⁺ ] [M1 ⁺ ] [M4 ^{2 +} ] [Y] ^n- (IV.Ch), where n = 4, [A1 ⁺ ] [M5 ^{3 +} ] [Y] ^n- (IV.Ci), where n = 4, [A1 ⁺ ] ⁺ [M4 ^{2 +} ] [Y] ^n- (IV.Cj), where n = 3, and where [A1 ⁺ ], [A2 ⁺ ] and [A3 ⁺ ] are selected, independently of one another, from the groups mentioned for [A ⁺ ], [Y] ^{n- has} the meaning given under formula (IV.A) and [M1 ⁺ ] , [M2 ⁺ ], [M3 ⁺ ] monovalent metal cations, [M4 ²⁺ ] divalent metal cations and [M5 ³⁺ ] trivalent metal cations. A compound according to claim 4, wherein the cations in the salt groups are selected from the cations of the formulas (IV.a) to (IV.w),

and oligomers containing these structures wherein R is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, polycyclyl, heterocycloalkyl, aryl or heteroaryl; Radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ attached to a ring carbon atom independently of one another represent hydrogen, a sulfo group, COOH, carboxylate, sulfonate, acyl , Alkoxycarbonyl, cyano, halogen, hydroxyl, SH, nitro, NE ¹ E ² , alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, cycloalkyl, cycloalkyloxy, cycloalkenyl, cycloalkenyloxy, polycyclyl, polycycloxy, heterocycloalkyl, aryl, aryloxy or heteroaryl where E ¹ and E ² independently of one another are hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ which are bonded to a ring heteroatom, are hydrogen, SO ₃ H, NE ¹ E ² , alkyl, alkoxy, alkenyl, cycloalkyl, cycloalkenyl, polycyclyl, heterocycloalkyl, aryl or heteroaryl, where E ¹ and E ² independently of one another represent hydrogen , Alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, or two adjacent radicals R ¹ to R ^{9 can} also be together with the ring atoms to which they are attached, for at least one fused, saturated, unsaturated or aromatic ring or a ring system having 1 to 30 carbon atoms, wherein the ring or the ring system 1 to 5 non-adjacent heteroatoms or heteroatom-containing groups may have and wherein the ring or the ring system may be unsubstituted or substituted, wherein two geminal radicals R ¹ to R ^{9 may} also be taken together for = O, = S or = NR ^b , where R ^{b is} hydrogen, alkyl, cycloalkyl , Aryl or heteroaryl, wherein in the compounds of formula (IV.x.1) R ¹ and R ³ or R ³ and R ^{5 may} also be taken together for the bond portion of a double bond between the ring atoms which carry these radicals, where one of R, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ or R ⁹ may be a linking site to the linker group; B in the compounds of formulas (IV.x.1) and (IV.x.2) together with the CN group to which it is attached is a 4- to 8-membered, saturated or unsaturated or aromatic cycle which is optionally substituted and / or which may optionally have further heteroatoms or heteroatom-containing groups and / or may comprise further fused saturated, unsaturated or aromatic carbocycles or heterocycles , A compound according to any one of claims 4 or 5, wherein the anions in the salt groups are selected from the group of halides, pseudohalides and halogen-containing compounds of the formulas: F ^- , Cl ^- , Br ^- , I ^- , BF ₄ ^- , PF ₆ ^- , AsF ₆ ^- , SbF ₆ ^- , SiF ₆ ^2- , ClO ₄ ^- , CF ₃ SO ₃ ^- , (CF ₃ SO ₃ ) ₂ N ^- , CF ₃ CO ₂ ^- , CCl ₃ CO ₂ ^- , CN ^- , SCN ^- , OCN ^- ; the group of sulfates, sulfites and sulfonates of the general formulas: SO ₄ ^2- , HSO ₄ ^- , SO ₃ ^2- , HSO ₃ ^- , R ^c OSO ₃ ^- , R ^c SO ₃ ^- ; Nitrates: NO ₃ ^- ; the group of phosphates of the general formulas: PO ₄ ^3- , HPO ₄ ^2- , H ₂ PO ₄ ^- , R ^c PO ₄ ^2- , HR ^c PO ₄ ^- , R ^c R ^d PO ₄ ^- ; the group of phosphonates and phosphinates of the general formulas: R ^c HPO ₃ ^- , R ^c R ^d PO ₂ ^- , R _c R _d PO ₃ ^- ; the group of phosphites of the general formulas: PO ₃ ^3- , HPO ₃ ^2- , H ₂ PO ₃ ^- , R ^c PO ₃ ^2- , R ^c HPO ₃ ^- , R ^c R ^d PO ₃ ^- ; the group of phosphonites and phosphinites of the general formulas: R ^c R ^d PO ₂ ^- , R _c HPO ₂ ^- , R ^c R ^d PO ^- , R ^c HPO ^- ; Antimonates: SbO ₂ ^2- , SbO ₄ ^3- ; the group of carboxylic acids of the general formula: R ^c COO ^- ; Anions of hydroxycarboxylic acids and sugar acids; Saccharinates (salts of o-benzoic acid sulfimide); the group of bristles of the general formulas: B (R ^c ) ₄ ^- , BO ₃ ^3- , HBO ₃ ^2- , H ₂ BO ₃ ^- , R ^c R ^d BO ₃ ^- , R ^c HBO ₃ ^- , R ^c BO ₃ ^2- , B (OR ^c ) (OR ^d ) (OR ^e ) (OR ^f ) ^- , B (HSO ₄ ) ₄ ^- , B (R ^c SO ₄ ) ₄ ^- ; the group of boronates of the general formulas: R ^c BO ₂ ^2- , R ^c R ^d BO ^- ; the group of carbides: C ^4- (methanide), C ₂ ^2- (acetylide), C ₃ ^4- (allenide); the group of carbonates and carbonic esters of the general formulas: HCO ₃ ^- , CO ₃ ^2- , R ^c CO ₃ ^- ; the group of silicates and silicic acid esters of the general formulas: SiO ₄ ^4- , HSiO ₄ ^3- , H ₂ SiO ₄ ^2- , H ₃ SiO ₄ ^- , R ^c SiO ₄ ^3- , R ^c R ^d SiO ₄ ^2- , R ^c R ^d R ^e SiO ₄ ^- , HR ^c SiO ₄ ^2- , H ₂ R ^c SiO ₄ ^- , HR ^c R ^d SiO ₄ ^- ; the group of alkyl or arylsilanolates the general formulas: R ^c SiO ₃ ^3-, R ^c R ^d SiO ₂ ^2-, R ^c R ^d R ^e SiO ^-, R ^c R ^d R ^e SiO ₃ ^-, R ^c R ^d R ^e SiO ₂ ^- , R ^c R ^d SiO ₃ ^2- ; the group of carboximides, bis (sulfonyl) imides and sulfonylimides of the general formula:

the group of methides of the general formula:

the group of alkoxides and aryloxides of the general formula R ^c O ^- ; the group of hydrogen sulfides, polysulfides, hydrogen polysulfides and thiolates of the general formulas: HS ^- , [S _v ] ^2- , [HS _v ] ^- , [R ^c S] ^- , where v is a whole positive number from 2 to 10, the Radicals R ^c , R ^d , R ^e and R ^f independently of one another represent - hydrogen; - Alkyl, preferably C ₁ -C ₃₀ -alkyl, more preferably C ₁ -C ₁₈ -alkyl, which is unsubstituted, or as defined above, is substituted, and / or, as defined above, interrupted by at least one heteroatom or heteroatom-containing group can be; - Aryl, preferably C ₆ -C ₁₄ -aryl, more preferably C ₆ -C ₁₀ -aryl, which is unsubstituted, or as defined above, is substituted; - Cycloalkyl, preferably C ₅ -C ₁₂ -cycloalkyl, which is unsubstituted, or as defined above, is substituted; - Heterocycloalkyl, preferably heterocycloalkyl having 5 or 6 ring atoms, wherein the ring in addition to carbon ring atoms 1, 2 or 3 heteroatoms or heteroatom-containing groups which is unsubstituted, or as defined above, is substituted; - Heteroaryl, preferably heteroaryl having 5 to 10 ring atoms, wherein the ring in addition to carbon ring atoms 1, 2 or 3 heteroatom or heteroatom-containing groups which are selected from oxygen, nitrogen, sulfur and NR ^a , which is unsubstituted, or as defined above, substituted is; in which anions having a plurality of radicals R ^c to R ^f , in each case two of these radicals together with the part of the anion to which they are attached, for at least one saturated, unsaturated or aromatic ring or a ring system having 1 to 12 May be carbon atoms, wherein the ring or the ring system may have 1 to 5 non-adjacent heteroatoms or heteroatom-containing groups, which are preferably selected from oxygen, nitrogen, sulfur and NR ^a , and wherein the ring or the ring system is unsubstituted or may be substituted; wherein at least one of the radicals, preferably one of the radicals R ^c , R ^d , R ^e and R ^{f may represent} a binding site to the linker group. A compound according to any one of the preceding claims, wherein the linker is selected from a chemical bond, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-S- , -S-CO-, -CO-N (R ^a ) -, -N (R ^a ) -CO-, -N (R ^a ) -CO-O-, -O-CO-N (R ^a ) - , -N (R ^a ) -CO-N (R ^a ) -, -CH ₂ -O-, -O-CH ₂ -, or an (n + m) valent C ₁ -C ₅₀ -hydrocarbon radical which can be replaced by O-, -S-, -NR ^a -, -PR ^a -, -SiR ^a R ^aa and / or -SO ₂ - one or more times, for. Example, single, double, triple, quadruple or more than fourfold, and wherein R ^{a is} preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl and R ^{aa is} preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyl or aryl and the (n + m) -valent C ₁ -C ₅₀ hydrocarbon radical is derived formally by abstraction of n + m H atoms from the corresponding parent compound. A compound according to any one of claims 1 to 7, wherein the group HTM is selected from groups of the general formula (V)

wherein R ¹¹ to R ¹⁴ independently of one another are hydrogen, or in each case unsubstituted or substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, where the four latter can each also be part of a fused ring system, with the proviso that at least one of the radicals R ¹¹ to R ^{14 represents} a binding site to a linker. A compound according to any one of claims 1 to 7, wherein the group HTM is selected from groups of the general formula (VI)

wherein # is a linker to a linking site, R ²⁰ and R ²¹ are each independently unsubstituted or substituted cycloalkyl, heterocycloalkyl, aryl or hetaryl, each of which may also be part of a fused ring system. A compound according to claim 9, wherein R ²⁰ and R ^{21 are} independently selected from groups of the general formulas (1) to (8)

in which # is the point of attachment to the nitrogen atom, the radicals R ^{h are} each independently selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, fluorine, chlorine, bromine, NE ⁵ E ⁶ , nitro and cyano, wherein E ⁵ and E ⁶ independently of one another represent hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl, x in the formula 5 is 1, 2, 3, 4 or 5, in the formula 6 is 1, 2, 3 or 4 in which formula 7 is 1, 2 or 3 in which formula 8 is 1 or 2. A compound according to any one of claims 9 or 10 wherein R ²⁰ and R ^{21 are} both for

where # is the binding site to the nitrogen atom. Solar cell, in particular dye solar cell, the at least one compound as in one of claims 1 to 11 defines. Use of at least one compound as defined in any one of claims 1 to 11 as a halide termaterial, preferably as a p-type semiconductor, in particular as a p-type semiconductor in solar cells. Use of at least one compound as in one of claims 1 to 11, as an ionic liquid. Use according to claim 14, as a solvent for chemical reactions, as an aid to separation of mixtures, as excipients for extractive rectification for the separation of dense or azeotropic mixtures, as a heat carrier.