TW200821345A - Conductive polymer gels - Google Patents

Abstract

The present invention relates to conductive organic polymer gels, a process for preparing them, the use of the conductive organic polymer gels as solid electrolytes in electrochemical applications and also portable batteries, galvanic elements, accumulators or fuel cells which comprise these conductive organic polymer gels as solid electrolytes, as such. The present invention further relates to the production of nanoporous polymer foams comprising these conductive organic polymer gels.

Description

200821345 IX. Description of the invention: [Technical field of the invention] The invention relates to the use of a conductive organic polymer glue, a preparation method thereof, a conductive, stack-based adhesive for use as a solid electrolyte in electrochemical applications, and A portable battery, a current element, a battery or a fuel cell comprising the conductive organic polymer gel as a solid electrolyte as it is. The present invention is directed to the preparation of a nanoporous polymer foam comprising the conductive organic polymer gels.

[Prior Art] Solid electrolytes are generally known. For example, it is used as a leakage preventing electrolyte in a battery pack or a battery. A specific metal oxide containing a movable ion (for example, a doped acid ion, an indium oxide or a tin oxide doped with a hetero atom) can be used as the solid electrolyte. Further, a polymer electrolyte containing a polymer containing an ionic side group (e.g., a polycarboxylic acid, K propylene & or a polymer or a salt thereof) can be used as the solid electrolyte. The ionic group can be introduced into the polymer by mixing with a suitable polymer. A typical example is such as Up. The solid solution of the salt in the polyoxidation. The ion mobility of these polymer electrolytes is highly dependent on the local segment mobility of the polymer chain and is strongly influenced by the salt concentration of the polymer electrolyte and the break-through temperature. It is also possible to dissolve the high molecular weight crosslinked polymer in the 'washing into the conductive liquid and thus to produce the conductive polymer paste. 123766.doc 200821345 Pay particular attention to ionic liquids as conductive liquids. It is a salt with a low refining point. It has high ionic conductivity, wide electrochemical stability window, non-volatile, heat stable and non-flammable. + Ne0uze et al. (Chem c〇MMUN 2〇〇5, (7) and even (10) for the preparation of an inorganic porous ceria matrix comprising an ionic liquid 1 by polymerizing tetramethoxynonane in an ionic liquid a solid electrolyte of butyl-3-methyl oxime bis(difluoromethylsulfonimide).

2857GG4 discloses a method of preparing a conductive ionic rubber by mixing a hydrolyzable precursor molecule with an ionic liquid and a (right appropriate) acid and then allowing the mixture to stand for at least one day. The precursor molecules produce an inorganic polymer and, in the manner reported, obtain a cerium oxide containing ionic (d). N. A. Susan et al., j Am·Chem s〇c 2〇〇5, Η' Μ% to 4983 describes the i-ethyl _3 of a vinyl monomer and an ionic liquid in the presence of a small amount of a crosslinking agent. _ AA oxazole #雔^ ^, a monomer gel for the preparation of an ionic liquid by radical polymerization of a monomer in the sulphur oxazolidine bis(trifluoromethanesulfonimide). The radical polymerization is a chain-growth reaction in which only the molecular end of the active chain grows until the end of molecular growth is terminated by terminating or transferring the active site to another molecule. Individual macromolecules are formed in a very short time, so that phase separation may or may not occur depending on local concentration conditions. In the presence of a cross-linking agent, the distance between individual cross-linking points is very different in this way, and the polymer network becomes extremely uneven (V丄Raman and G.R. Palmese.

Langmuir 21(4)(10)5) 1539_1546). Therefore, the form of the polymer network (i.e., the aperture) cannot be set in a controlled manner. Because ionic conductivity is dependent on the rate at which anions or cations diffuse through the polymer network, 123766.doc 200821345 is therefore extremely disadvantageous. And therefore also depends on its pore size or morphology. [Inventive content] " The goal is to provide another solid electrolyte that is preferably configurable during preparation. The mesh is achieved by a conductive organic polymer gel which can be prepared by the following steps: a) providing a solution comprising the following:

Ο al· having a parental effect or a plurality of monomers or prepolymers, a2· ionic liquid or a mixture of a plurality of ionic liquids, =· right right, at least one component without cross-linking, b) borrowing The component u is polymerized with (if appropriate) components to form an organic polymer by condensation or addition polymerization in the presence of a mixture of an ionic liquid or a plurality of ionic liquids. The 'Electrical Organic Polymer Glue of this month is prepared by polycondensation or addition polymerization in a ionic liquid as a solvent from a monomer or a prepolymer and embedded in an ionic liquid in an organic crosslinked polymer. Organic three-dimensional crosslinked polymer. In other words, the organic crosslinked polymer swells in the ionic liquid. For the purposes of the present invention, the term, polycondensation "and, addition polymerization" is recommended in accordance with UPAC in ure & Appl. chem., vol. 66 (12) (1994) 2483-2486. Polycondensation and The addition polymerization is a stepwise reaction, in which the former 'σ spear is accompanied by the elimination of the low molecular 1 compound and the latter process is not accompanied by the elimination of the molecule. In the two types of reactions, the second form is formed from individual monomers. And further reacting with other monomers or dimers, trimers, oligomers or formed conjugates. In most polycondensation and addition polymerization reactions, 123766.doc 200821345 and * two reactions occur The thiophene group has the same reactivity, that is, the functional groups bonded to the monomer or oligomer and the polymer react with the same probability. The average molecular weight: 堇 increases sharply at the end of the reaction; the phase separation can be seen from the reaction parameters of the selected system. Aggregation or cross-linking that occurs 'and in this situation

According to the present invention, the reaction is carried out in a polycondensation or addition polymerization form in a manner similar to the sol gel method. This makes it possible to precisely control the aperture and shape. This control is important for using the conductive paste as the solid electrolytic f because the diffusion of ions can be set in this manner. The aperture of the adhesive is set within the TM-wide window. Since the ionic liquid h is volatilized, the (tetra) organic polymer gel of the invention has high ionic conductivity and extremely high treatment. The conductive polymer paste of the present invention can be used as a solid electrolyte. Since the ionic liquid system is held in the polymer, the electrolyte containing the conductive polymer paste of the present invention as an electrolyte can be prevented from leaking. The ionic liquid is removed from the polymer gel to produce a nanoporous polymer foam. The removed ionic liquid can be reused and reused in the preparation of conductive polymer gel or nanoporous polymer foam. This has developed an environmentally friendly and inexpensive way to produce a nanoporous polymer foam exhibiting excellent thermal insulation properties. An ionic liquid, also known as a liquid salt, is generally known to be soluble, preferably a salt melt of less than 18 °C. The melting point is better at _5〇. 〇 to 15〇. (In the range, even more preferably in the range of -20 ° C to 120 ° C and particularly preferably 〇. (: to 1 〇〇. (: For the purpose of the present invention, the ionic liquid is preferably · 123766.doc 200821345 (A) Salt of formula (I): [α]; [υΓ (I), oxidized cations are trivalent or tetravalent, where η is 1, 2, 3 or 4, [Α]+ is a tetraammonium cation, a sub, a phosphonium cation or a scaly cation and [Υ]η- is a monovalent, divalent, valent anion; (Β) a mixed salt of the formula (II):

[Al] + [A2] + [Y wide flla), where η = 2; [Al] + [A2] + tA3] + mn - (lib) ' where n = 3; or (IIe), where n = 4 Wherein [Aγ, [AY, [AY and [AY are independently selected from the group mentioned for [A] + and [Y] n- is as defined under (A); or (c) (III) Mixed salt: [ATi^rcAwnYr- (IIIa), where (4) [AYCAYtMVtMYtY]- (mb), where n (lllc) , where η = 4 ; (llld) , where η = 3 ; (llle) , Where η =: 3 ; (lllf) , where η = 2 ; (lllg) , where η = 4 ; (lllh) ' where η = 4 ; (llli) , where η == 4 ; or (lllj) , where η =3, [Α1] + [Α2] + [Μ1] + [Υ]η· [Αιγ[Μι] + [Μ2γ[Υ]η' [Αι] + [Μι] + [ΥΓ [Αι] + [Μιγ[ Μ4]2 + [Υ]η' [Αιγ[Μ5]3 + [Υ]η~ [Αι] + [Μ4]2+[Υ]η' where [AT, [ΑΥ and [Α亇 are independently selected from About [8]+ mentioned 123766.doc -10- 200821345 The group '[Υ]η is as defined by (A), and [Μ]+, [Μ2Γ, nuh+i monovalent metal cations, [M4j2+ is..., valence metal cation. ""Ion and [M5]3+ is three

For example, a compound suitable for forming an ionic liquid (tetra) sub-[A] is known from the cation ul+0Whyw A1 of the DE 102 02 SM body. Thus, the compounds may comprise oxygen, disulfide or especially a nitrogen atom 'eg at least one nitrogen atom, more preferably (1) a nitrogen atom than a second L atom, especially preferably m, ^ may also contain, for example, oxygen, Stone six

Or other heteroatoms of phosphorus atoms. Nitrogen $;, L 虱 atom is a suitable carrier for a positive charge in the cation of the ionic liquid. Then the proton or the deutero can be balanced with the anion to produce an electrically neutral molecule. If the nitrogen atom is a carrier of a positive charge in the cation of the ionic liquid, in the synthesis of the ionic liquid, the cation can be first produced, for example, by quaternizing the nitrogen atom of the amine or the nitrogen heterocycle. It is possible to realize the quarterly money by densifying the nitrogen atom. Depending on the alkylating agent used, salts having different anions can be obtained. This anion can be formed in another step of the synthesis in the case where quaternization itself is not possible to form the desired anion. For example, starting from an ammonium halide, the halide can be reacted with a Lewis acid to form a complex anion from the halide and the Lewis acid. Alternatively, the halide can be replaced with an anion. This can be achieved by adding a metal salt under the conditions of the formed metal precipitate, by means of an ion exchanger or by replacing the ion with a strong acid (while releasing hydrogen halide). For example, suitable methods are described in Angew Chem. 2000, 112, pages 3926-3945 and references cited therein. 123766.doc -11 - 200821345 A suitable institute for quaternizing a nitrogen atom in an amine or a nitrogen heterocycle, such as a Ci_C丨8 alkyl group, preferably a soil of c (for example and especially excellent soil 'especially Preferably, the alkyl group may be unsubstituted or the same or different substituents. /, or the oxime phase preferably contains at least one 5- or 6-membered heterocyclic ring (especially 5 = same as 4 hetero % has at least one nitrogen atom and, if appropriate, oxygen or sulphur

Preferably, the compound comprises at least a 5- or 6-membered heterocyclic ring: the compound side has % oxime, 2 or 3 nitrogen atoms, and sulfur or oxygen. Preferably, the compound has two nitrogen atoms. True, especially the extreme, the Gan A A 1 soil is a square heterocyclic ring. Particularly preferred compounds have a molecular weight of less than 1000 g/m Ql, g/mol and especially less than 25 〇g/m 〇1. Although preferably less than 500, it is preferably a cation selected from the group consisting of compounds of formula ((IVW):

(IVd) (IVe) R2

(IVf) 123766.doc -12- 200821345

123766.doc -13- 200821345

(IVp) (IVq) (IVq1)

(IVq") (IVr) (IVr_)

(IVr") (IVs)

/^OR3 + NIR (IVu) (IVv) (IVt) (IVw) and oligomers comprising the structures. Other suitable cations are compounds of the formulae (IVx) and (IVy)

FT —P—R1 | S—R I 1 R 1 R (IVx) (ivy) -14- 123766.doc 200821345 and an oligomer comprising the specific structure. In the above formulae (IVa) to (ivy), the group R is hydrogen or a carbon-containing organic saturated group having 1 to 20 carbon atoms which may be unsubstituted or interrupted or substituted by i to 5 hetero atoms or functional groups. Or an unsaturated, non-% or cyclic, aliphatic, aromatic or araliphatic group, and • the groups R to R are each independently hydrogen, sulfonic acid or have up to 20 carbon atoms and a carbon-containing organic saturated or unsaturated, acyclic or cyclic, valence, aromatic or araliphatic group which is unsubstituted or interrupted or substituted by i to 5 heteroatoms or functional groups, wherein a group in the formula (ιν) bonded to a carbon atom (not to a hetero atom) to another halogen or a functional group; or two adjacent groups derived from the group consisting of R1 to R9 Forming together a divalent, carbon-containing organic saturated or unsaturated, acyclic or cyclic, aliphatic, having 1 to 30 carbon atoms which may be unsubstituted or interrupted or substituted with from i to 5 heteroatoms or functional groups. An aromatic or araliphatic group. In the definition of the radicals R and R1 to R9, it is possible that the heteroatoms are in principle all heteroatoms which are capable of formally replacing the -CH2-group, the _CH= group, the group or the =c= group. If the carbon-containing group contains a hetero atom, oxygen, nitrogen, sulfur, phosphorus and ruthenium are preferred. Preferred groups are especially _〇·, _s〇_, , -NR·-, -N=, -PR, _, _PR, 2 and _siR, 2·, wherein the group is a carbon-containing group. The rest. In the above formula (IV), in the case where the group ... to ... is bonded to a carbon atom (instead of a hetero atom), it may also be bonded directly via a hetero atom, which is suitably a carbon atom or a hetero group. The atomic combination of all officials 123766.doc -15- 200821345 energy base. Suitable examples are -Ο Η (radio), =〇 (detailed carbonyl), -NH2 (amine), =NH (imino), -COOH (carboxyl), -CONH2 (carboxyguanamine), -S〇3H (sulfonic acid group) and -CN (cyano group). The functional group and the hetero atom may also be directly adjacent to each other to include a plurality of adjacent atoms (for example, _〇_(ether), -S-(thioether), -COO-(ester), -CONH- (second 醯Amines or a combination of -C〇nr,-(third guanamine)), for example, a di-(Ci-C4 alkyl)amine group, a CpC* alkoxycarbonyl group or a Ci-Czl. As the halogen, oxygen, chlorine, bromine and angstrom can be mentioned. The group R is preferably: • may be unsubstituted or substituted by one or more hydroxyl, _, phenyl, cyano, C1-C6 alkoxy groups and/or sulfonic acids and have a total of 1 to 2 〇 An unbranched or branched alkyl group of a carbon atom, such as methyl, ethyl, 丨-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-propyl (different) Butyl), 2-methyl-2-propyl (t-butyl), 1-pentyl, pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1- Butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimercapto-1-propyl, 1-hexyl, hexyl, 3-hexyl, 2-methyl_1_ Pentyl, 3-methyl-1-pentyl, 4•methyl-丨-pentyl, 2-methyl-2-pentyl, 3-methyl-2-indenyl, 4-methyl-2- Mercapto, 2 methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethylbutyl, 2,3-monodecyl-1-butyl, 3,3-di Methyl-1-butyl, 2-ethyl-;[_butyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, hexyl, i.octyl, fluorenyl , 丨-fluorenyl, undecyl, anthracene-dodecyl, ^tetradecyl, 1-hexadecane, i-octadecane, 2-ylethyl, stupid 3-phenylpropyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-123766.doc -16- 200821345 (ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl) Base, trifluoromethyl, difluoromethyl, fluoromethyl, penta-ethyl, heptapropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, I-pentyl, undecafluoro Isoamyl, 6-hydroxyhexyl and propyl sulfonic acid; • diol, butanediol and its polymer having 1 to 1 unit and hydrogen or CVC8 alkyl as terminal group, such as RA〇_ (CHRBCH2 〇)n_CHRB_CHr or RAGKCH2CH2CH2CH2〇VCH2CH2CH2CH20-, wherein each of RA&RB is preferably hydrogen, methyl or ethyl and η is preferably 〇 to 3, especially 3-oxabutyl, 3-oxapentane , 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3,6,9-trioxadecyl, 3,6,9·trioxadecyl, 3, 6,9,12-tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl; •vinyl; and • fluorene, fluorene-di-Cl_C6 alkylamino group, such as hydrazine , Ν_dimethylamino group and hydrazine, hydrazine _: ethylamino group. The group R is particularly preferably an unbranched and unsubstituted alkyl group such as methyl, ethyl, 1-propyl, hydrazine-butyl, hydrazino-pentyl, fluorenyl, hexyl, 1-octyl , 1-indenyl, 1-dodecyl, tetradecyl, decyl-hexadecyl, 1-octadecyl, especially methyl, ethyl, butyl and octyl, or CH30- (CH2CH20)n-CH2CH2- and CH3CH20-(CH2CH20)n-CH2CH2-, the towel n is 〇 to 3. Preference is given to radicals R1 to R9 which are each independently of one another: • hydrogen; • halogen; 123766.doc 17-200821345 • functional groups; • optionally via functional groups, aryl groups, alkyl groups, aryloxy groups , alkoxy, sulfhydryl, heteroatom and/or heterocyclic substituent 'and/or interrupted by one or more oxygen and/or biting atoms and/or one or more substituted or unsubstituted imine groups a C 1 8 alkyl group; • optionally substituted with a functional group, an aryl group, an alkyl group, an aryloxy group, an alkoxy group, a olefin, a hetero atom, and/or a heterocyclic ring, and/or via one or more oxygen and/or Or sulfur

a C 1 8 thin group interrupted by an atom and/or one or more substituted or unsubstituted imine groups;

U • C0_Ci2 aryl group optionally substituted by a functional group, an aryl group, an alkyl group, an aryloxy group, a hetero atom and/or a heterocyclic ring; • optionally a functional group, an aryl group, an alkyl group, an aryloxy group, Heteroatom and/or heterocyclic substituted C5-Ci2 cycloalkyl • C5-C12 cycloalkenyl optionally substituted by functional group, aryl, alkyl, aryloxy, hetero atom and/or heterocyclic ring 5 or 6 members of a functional group, an aryl group, an alkyl group, an aryloxy group, a hetero atom and/or a heterocyclic ring, an oxygen-containing, nitrogen- and/or sulfur-heterocyclic ring; or an alkoxy group, a halogenated alkoxy group, Two adjacent groups (R1 to r9) of a haloalkoxy group or an alkoxyhalohalide are formed from a functional group, an aryl group, an alkyl group, an aryloxy group, an alkoxy group, a dentate, A hetero atom and/or a heterocyclic ring is an unsaturated, saturated or aromatic ring which is interrupted by one or more oxygen and/or sulfur atoms and/or — or a plurality of substituted or unsubstituted imine groups. Preferably, the c!-c!8 alkyl group is substituted by a functional aryl group, an alkyl group, an aryloxy group, an alkoxy group, a halogen 123766.doc -18-200821345, a hetero atom and/or a heterocyclic ring. Base, ethyl, 1-propyl, 2-propyl, butyl, 2-butyl, 2-mercapto-1-propyl (isobutyl), 2-methyl-2-propyl (third Base), pentyl, 2-pentyl, 3-pentyl, 2-mercapto-1-butyl, 3-methyl-1-butyl, 2-nonyl-2-butyl, 3-methyl -2, butyl, 2,2-dimethyl-1-propyl, hexyl, 2-hexyl, hexyl, 2-mercapto-1,pentyl, 3-methyl-1 -pentyl, 4-methyl-1-pentyl, 2-indolyl-2-ylyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl , 3-mercapto-3-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimercapto-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_ tridecylpentanyl, 1,1,3,3-tetramethylbutyl, 1-decyl, 丨-fluorenyl, fluorenyl undecyl, 1-dodecyl, 1-tride Alkyl, i-tetradecyl, 丨_fifteen Base, 1-hexadecyl, 1-heptadecyl, 1-octadecanyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2_cyclohexylethyl, 3-cyclohexylpropyl, benzyl (phenylmethyl), diphenylmethyl I (diphenylmethyl), triphenylmethyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, α,α-dimethylbenzyl, p-tolylmethyl, 丨_(p-butylphenyl)ethyl, p-chlorobenzyl, 2, 4-Dichlorophenyl fluorenyl, p-methoxy benzyl group, m-ethoxymethyl, 2- tranethyl, 2-cyanopropyl, 2-methoxycarbonyl, ethyl 2- Oxycarbonylcarbonyl, 2-butoxycarbonylpropyl, hydrazine, 2-bis(methoxycarbonyl)ethyl, methoxy, ethoxy, methionyl, anthracene, 3_di-4tetradecyl, α%-2 -yl, 1,3-dioxacarb-2-yl, 2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl , 2-hydroxyethyl, 2-hydroxypropyl, 3 · ankyrinyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2·aminoethyl, 2•amine = 123766.doc -19- 200821345 Base, 3-aminopropyl, 4-aminobutyl, 6-amine Hexyl, 2-methylaminoethyl, 2-methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2-di Methylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethylaminobutyl, 6-dimethyl

Aminohexyl, 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, Phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxyethyl, 6-methoxyhexyl, ethoxyethyl , 1 ethoxypropyl, ethoxypropyl, 4-ethoxybutyl, 6-ethoxyhexyl, ethenyl, wherein n is from 1 to 30, and b = 〇 or 丨 CnF2 (n Small... b) H2a+b (eg CF3, (10), cH2cH2-C(n.2)F2(n-2)+1, c-heart c8F17, c10f21, Ci2F25), gas methyl, 2-chloroethyl, three Chloromethyl, 1 broad monomethyl 2' chloroethyl, methoxymethyl, 2-butoxyethyl, diethylmethyl, diethoxyethyl, 2-isopropoxy Ethyl, 2-butoxypropane: octyloxyethyl, methoxyisopropyl, 2-(methoxycarbonyl)ethylene, 2 (ethionyl)ethyl, 2-(n-butoxy) Ethyl, butylthiomethyl: 7-dialkylthioethyl, 2-phenylthioethyl, 5-mercapto-3-oxo-yl-3,6-dioxaoctyl, 11- Meryl-3,6,9-trioxa-10-y-2,yl 1oxaheptyl, anthracene, fluorenyl 8-diox -烧^14•搜基·4,Μ2β trioxane fifteen yards, 9-carbyl·5·oxaxanthene, quinone-dioxatetradecyl, % methoxy ioxazepine & base_3,6·dioxaoctyl, 1methoxy·3 from trioxa-11, polyoxy-4_oxaheptyl, methoxy #二氧十&A Oxygen_4,8 trioxane pentaha, 9. methoxy _5_ 123766.doc -20- 200821345 , fluorenyl 14-methoxy _5,1 〇 dioxatetradecyl , % ethoxy _3_ oxapentyl 8-ethoxy-3,6-dioxaoctyl, ethoxylated, hexa-alkyl, 7·ethoxy-4_oxaheptyl 11. Ethoxy-4,8-dioxaza-homo-based, 15·ethoxy-4,8,12•trioxapentanyl, 9-ethoxy-5·oxazepine Or 14_ethoxy_5,1〇_oxatetradecyl. The C2_Ci8 alkenyl group interrupted by one or more substituted or unsubstituted imido groups is preferably a vinyl group, a 2-propenyl group, a 3-butenyl group, a cis-butenyl group, and optionally a functional group. Substituent, aryl, alkyl, aryloxy, alkoxy, dentate, heteroatom and/or heterocyclic, and/or via one or more oxygen and/or sulphur

Trans-2-butylenyl or CnF2 (called -U-wHza-b, wherein r^30, 〇^^b=〇 or 1 〇 may be optionally via a functional group, an aryl group, an alkyl group, an aryloxy group, an alkoxy group The C6_Ci2 aryl group substituted with a phenyl group, a hetero atom, and/or a heterocyclic ring is preferably a phenyl group, a tolyl group, a xylyl group, an α-naphthyl group, a β-naphthyl group, a 4-biphenyl group, a chlorophenyl group, Dichlorophenyl, triphenylphenyl, difluorophenyl, methylphenyl, dimethylphenyl, dinonylphenyl, ethylphenyl, diethylphenyl, isopropylphenyl, Tributylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloro Naphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-dimethoxyphenyl, 2,6-diphenyl , 4-bromophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl, 4-dimethylaminophenyl , 4-ethenylphenyl, methoxyethylphenyl, ethoxymethylphenyl, methylthiophenyl, isopropylthiophenyl or tert-butylsulfanyl or C6F ( 5_a) Ha, where 〇$a£ 5. 123766.doc • 21 - 200821345 A Cs-Ci2 cycloalkyl group optionally substituted by a functional group, an aryl group, an alkyl group, an aryloxy group, an alkoxy group, a halogen, a hetero atom and/or a heterocyclic ring is preferably a ring. Pentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, Methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dicyclopentylpentyl, CnF2(n-aH1-b) H2a.b, where n$30, 〇$a$n and b = 〇 or 1, or a saturated or unsaturated bicyclic ring system such as a pendant or norbornyl group. Optionally, via a functional group, an aryl group, an alkyl group, The aryloxy, alkoxy, halogen, hetero atom and/or heterocyclic substituted Cs-Cu cycloalkenyl group is preferably 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2 , 5-cyclohexadienyl or CnF2(na).3(ib) H2a"b ' wherein n$30, 〇$a$n and b=〇 or 1. Depending on the functional group, aryl group, alkyl group, Aryloxy, alkoxy, halogen, heteroatom and/or heterocyclic substituent 5 or 6 members, oxygen, nitrogen and/or sulfur heterocycles are preferably furyl, thienyl, pyrrolyl, pyridyl, i-yl, benzoxazolyl, meta-dioxole , dioxyl (di〇xyl), benzoimidazolyl, benzothiazolyl, dimethyl π-pyridyl, methyl quinolyl, dimethyl-bromo, methoxyfuranyl, dimethyl An alkoxy group or a difluoroacridinyl group. If two adjacent groups are formed together, a functional group, an aryl group, a fluorenyl group, an aryloxy group, an alkoxy group, a dentate, a hetero atom, and/or a hetero group may be formed. Preferably, the ring is substituted, and optionally, an unsaturated, saturated or aromatic ring interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imine groups is preferred. , 3-extended propyl, 1,4-tert-butyl, 1,5-extended pentamyl, oxime-oxa-3丨 123766.doc -22· 200821345 propyl, oxa·1,3·propyl , 2-oxa-1,3-propanyl, κ-oxa-1,3-1,3-propenyl, 3-oxa-, 1,5-amyl, 丨-aza-i, propylene Base, 1-CVC4 alkyl-hydrazine-aza", 3_extended propenyl, anthracene, lenidine 丨, •, 3• dilute , 1-aza-1,4-exetylene-^-dienyl or 2-aza-1,4-exetylene-quinonediyl. If the above group contains an oxygen and/or sulfur atom and/or a substituted or unsubstituted imine group, the number of oxygen and/or sulfur atoms and/or imine groups is not limited.

system. In general, there will be no more than 5, preferably no more than 4 and especially preferably no more than 3 in the group. The above groups to the right contain a hetero atom, and usually at least one carbon atom, preferably at least two carbon atoms, is present between any two hetero atoms. Particularly preferred are groups which are each independently of each other to the group of the following groups: to size 9: • hydrogen; unsubstituted or via- or poly(tetra)yl, i-, phenyl, cyano and/or CA An unbranched or branched CVC18 alkyl group substituted with a base and/or a reductive acid and having a total of (1) carbon atoms, such as methyl, ethyl, propyl, 2, yl, b butyl, 2, butyl, 2- Methyl-hydrazine-propyl (isobutyl: methyl I propyl (t-butyl), 1 · pentyl, 2-pentyl, 3-pentyl; 2-methyl-1-butyl, 3·A Base-1·butyl, 2-methyl-2-butyl, 3-yl-2-butyl, 2,2·dimethylpropylpropyl, 2-hexyl, 3-:yl, 2-methyl -b-pentyl, 3-methyl+pentyl, 4-methylpentaerythride; wide methyl-2·pentyl, 3-methyl-2-amyl, 4·methyl-2-pentyl, 2 · Methyl-3-pentyl, 3-methyl-3-pentyl, 2,2•dimethylbutanyl, 2,3-methyl-L-butyl, 3,3-dimethyl Butyl, 2-ethylbutyl butyl, 123766.doc -23- 200821345 2,3-dimethyl-2-butyl, 3,3-dimethyl- 2-butyl, ^heptyl, 1_ Octyl, 1-indenyl, 1-indenyl, oxime-undecyl, oxime-dodecyl, tetradecyl, 1-hexadecyl, :U Octadecyl, hydroxyethyl, benzyl, 3-phenylpropyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-(ethinylcarbonyl)ethyl, 2-( n-Butoxy-carbonyl)ethyl, trifluoromethyl, monofluoromethyl, fluoroindolyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl , undecafluoropentyl, undecafluoroisopentyl, 6-hydroxyhexyl and propyl sulfonic acid; • diol, butanediol and its having 1 to 1 unit and all of the above with rodent or CVC8 A base polymer as a terminal group, for example, ra〇_(chrB — CH 2 —〇)nCHRB_CH 2 or RA〇—(CH 2 CH 2 CH 2 CH 20 ) n CH 2 CH 2 CH 2 CH 2 , wherein R and R are each preferably hydrogen, methyl or ethyl and 11仫 is 0 to 3, especially 3-oxahexyl, 3-oxapentyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3,6,9-trioxane Heterofluorenyl, 3,6,9-trioxadecyl, 3,6,9,12-tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl; • Vinyl; and • N,N-di-CrC6 alkylamino group, such as N,N-didecylamino and N,N-diethylamino. Especially preferably independently of each other Hydrogen or a group of Ci-Ci8 alkyl groups R1 to R9, such as methyl, ethyl, butyl, decylpentyl, 1-hexyl, 1-heptyl, 1-octyl, phenyl, 2-hydroxyethyl , 2—cyanoethyl, 2-(methoxycarbonyl)ethyl, 2—(ethoxycarbonyl)ethyl, 2 gas n-butoxycarbonyl)ethyl, N,N-dimethylamino, N,N _Diethylamino, chloro or CH30-(CH2CH20)n-CH2CH2- and CH3CH20-(CH2CH20)n- 123766.doc -24- 200821345 CH2CH2- wherein η is 〇 to 3. Particularly preferred pyridinium ions (IVa) are the same, wherein: • one of the groups R to R5 is a || a von τ group, an ethyl group or a gas and the remaining groups ... to R5 are each hydrogen; Is a dimethylamino group and the remaining groups r1, r2, r4 &r5WM; • all groups R1 to R5 are hydrogen; • R2 is a carboxyl group or carboguanamine and the remaining groups r1, r2, r4 and r5 are each hydrogen ; or # • R and R2 or R2 and R3 are butyl-1 3--loose and η is good, rj Μ monoalkenyl and the remaining groups R1, R2, R4 and R5 are each hydrogen; and especially for their ions, Wherein: • R1 to R5 are each hydrogen; or • the group Ri to R5 is methyl or ethyl and the remaining groups ri to 5 are each nitrogen. As a particularly excellent pyridinium ion (IVa), mention may be made of 丨-methyl-pyridine rust, 1-ethylpyridinium, and! · (! _ butyl) β is more than pyridine, Ηι•hex 吼 矿 矿, 1- (1 _ octyl 镔 镔, W1 hexyl) n than bite rust, 〖- (1 · ^ base) 吼 bite, Mi-dodecyl group is better than biting W, W1•tetradecyl) pyridine bite (1-hexadecyl) pyridinium, L2-dimethylpyridinium, 丨_ethyl_2_methyl Mouth ratio biting, 1-(1-butyl)_2·曱 base bite rust, i servoyl methyl divalent, -octyl)-2_methyl 吼 bite, ^(1)12 alkyl)_2_ Methylpyridinium, 1-(1-tetradecyl)_2-methylpyridinium, anthraquinone-hexadecyl)-2-pyridylpyridyl rust, methyl-2-ethylpyridinium, ,2-diethylpyridinium iron, 1-(1-butyl)-2-ethyl oxime lock, ^•hexyl)_2_ethyl μ 123766.doc -25- 200821345 镔, 1-(1-xin ))-2-ethylpyridinium, 丨·(budecyl)_2-ethylpyridinium, 1·(1-tetradecyl)-2-ethylpyridinium, hexaalkyl)_2_B Pyridine rust, 1,2-dimethyl-5-ethylpyridinium, iota, 5-diethyl-2-methylpyridinium, 1-(1-butyl)-2-methyl-3-ethyl Pyridine rust, [_〇·hexyl 2-methyl-3-ethylpyridinium and !·(1_octyl)_2_甲Ethylpyridinium, 1-(1-dodecyl)-2-methyl-3·ethylpyridinium, 1-(1-tetradecyl)>2·methyl-3-ethylpyridine镔 and 1β(1-hexadecyl)_2_methyl_3•ethylpyridine, especially excellent azine oxime ions (IVb) are their ions, wherein ··· R1 to R4 are each hydrogen; or • group One of R1 to R4 is a mouse. The methyl group or the ethyl group and the remaining groups ... to the rule 4 each particularly excellent pyrimidine oxime ion (IVc) is a plasma thereof, wherein:

Methyl or ethyl and ... to 4 are each independently hydrogen or samarium, methyl or ethyl, R2AR4 is each methyl and r3 is hydrogen. Especially excellent. More than the kind of handyman ^7", recognize ^ ~

----T (two) Hungary or hydrogen. IVR1 is hydrogen, methyl is chlorine or methylhexyl, 1-octyl,

123766.doc -26- 200821345 are each independently hydrogen, methyl or ethyl. As a particularly excellent imidazolium ion (IVe), mention may be made of 丨_mercaptoimidazole, 1-ethylimidazole rust, 1 _(丨-butyl)imidazolium, 丨·(Businyl)imidazole 1 -(丨-dodecyl)imidazole rust, 1-(1-tetradecyl)imidazole rust, 1-(1-deca-, alkyl)imidazolium, 1,3-dimethylimidazole rust, ^ Ethyl_3_methylimidazole, 1-(1-butyl>3-methylimidazolium rust, butyl)_3_ethylimidazolium, 1-U-hexyl)-3-mercaptoimidazole rust, 1-(丨_hexyl)·3·ethylimidazolium, 1-(1-hexyl)-3-butylimidazolium, 1_(丨-octyl)_3_methylimidazole, 1-(1-xin Base)·3_ethyl miso rust, i_(i_octyl)_3_ butyl imiline, 1-(1-dodecyl)-3-methyl-imidazolium, 1_(丨_十二Alkyl)-3_ethyl sigma rust, 1-(1-dodecanyl)_3_ butyl sulphide, ι_(ι_diozoene)-3-octyl imidazole rust, ι_(ι _Tetradecyl)_3_mercaptoimidazole rust, 丨_(budecyl)_3_ethylimidazole rust, ι_(ΐ-tetradecyl)_3_butylimidazolium, 1_(1_fourteen Alkyl)_3_octyl imidazolium, anthracene/hexadecyl)-3-mercaptoimidazolium, 1-(1- Cetyl)_3_ethylimidazole rust, oxime hexadecyl)-3-butylimidazolium, ι_(ι_hexadecyl)-3_octyl imidazole rust, hydrazine, 2- Dimercapto-imidazolium, 1,2,3-trimethylimidazolium rust, lethyl-2,3-dimethylimidazolium, 1-(1-butyl)-2,3-dimethylimidazole镔,; u(1_hexyl)_2,3_dimethylimidazole rust, 1-(1-octyl)-2,3-dimercaptoimidazole rust, L4-dimercaptoimidazole rust, 1,3, 4-trimethylimidazolium, iota, 4-dimercapto-3_ethylimidazole rust, 3-butylimidazole rust, 1,4-dimethyl-3-octyl imidazolium, M, 5_3 Methylimidazole rust, 1,3,4,5-tetramethylimidazolium, iota, 4,5-trimethyl-3-ethyl-salt, 1,4,5-trimethyl-3- Butyl imidazole rust and 1,4,5-trimethyl-3-octyl imidazole rust. 123766.doc -27- 200821345 Especially excellent oxazolium ions (iVf), (1乂§) and (1¥§,) are their ions' where: • R1 is hydrogen, methyl or ethyl and R2 to R4 Each is independently hydrogen or methyl. Particularly preferred pyrazolium ions (IVh) are the same, wherein R to R are each independently hydrogen or methyl. Particularly preferably, the 1-pyrazoline rust ions (IVi) are the same, wherein: R to R are each independently hydrogen or methyl. Particularly excellent 2-pyrazolinium ions (IVj) & (Ivj,) are the same, in the basin: ', • R is hydrogen, methyl, ethyl or phenyl and (1) to ^ are each independently Hydrogen or methyl. Particularly preferably, the 3-pyrazolinium ions (IVk) and (IVkf) are the same, wherein: ', • R1 and R2 are each independently 氲, methyl, ethyl or phenyl and each of R to R Independently hydrogen or methyl. Particularly preferably, the imidazolinium ion (IVI) is a plasma thereof, wherein: • R1 and R2 are each independently hydrogen, methyl, ethyl, butyl or phenyl 6, and R3 and R4 are each independently hydrogen. Methyl or ethyl, and R5 and R0 are each independently hydrogen or methyl. Particularly excellent imidazoline rust ions (IVm) and (IVm,) are their ions, straight: ', • Rl and R2 are each independently hydrogen, methyl or ethyl and r3 to R6 are each independently hydrogen. Or methyl. 123766.doc -28- 200821345 Particularly excellent imidazoline rust ions (IVn) and (Ivn,) are their ions, wherein: ', • RlSR3 are each independently hydrogen, methyl or ethyl and R4 to R6 are each other Independently hydrogen or methyl. Particularly excellent thiazolium ions (IV〇) and (IV〇,) and oxazole rust ions (IVp) are specific ions, wherein: • R1 is hydrogen, methyl, ethyl or phenyl and R2 and R3 are each other Independently hydrogen or methyl. Particularly preferred 1,2,4-triazolium ions (IVq), (IVq,) and (IVq") are the same, wherein: • R and R2 are each independently hydrogen, methyl, ethyl or benzene. And R3 is hydrogen, methyl or phenyl. Particularly excellent 1,2,3-triazole rust ions (IVr), (IVr,) and (IVr. are their ions, wherein: • R1 is hydrogen, methyl Or ethyl and ... and 3 each independently of hydrogen or methyl or R2 and R3 are 1,4_butyl-dienyl. Especially excellent. Specific σ 镔 镔 ions (I vs) Is a plasma thereof, wherein: • R1 is hydrazine, methyl, ethyl or phenyl and R2 to R9 are each independently hydrogen or methyl. Especially excellent imidazolium quinone ions (1^^ are their ions, wherein: 'Rl and R4 are each independently hydrogen, methyl, ethyl or phenyl and each independently of 2 and R and R to R8 is hydrogen or methyl. Particularly preferred ammonium ions (IVu) are their ions, Wherein R to R are each independently Ci_c"alkyl; or 123766.doc -29- 200821345 R1 and R2 are 1,5-exopentyl or 3-oxasopentyl and Han 3 is c C!8 alkyl, 2-hydroxyethyl Or 2-cyanoethyl. As a particularly excellent ammonium ion (IVu), mention may be made of fluorenyl tris-(1 butyl) ammonium N,N-methylpiperidinium and N,N-dimethyl Benzoline oxime.

c An example of a third amine derived from the fourth ammonium ion of the formula (IVu) by quaternization with the mentioned group R is diethyl n-butylamine, diethyl _ third Amine, diethyl-n-pentylamine, diethyl-hexylamine, diethyloctyl-moon, monoethyl (2-ethylhexyl)amine, di-n-propylbutylamine, di-n-propyl Base - n-pentylamine, di-n-propylhexylamine, di-n-propyloctylamine, di-n-propylidene (2-ethyl-hexyl)amine, diisopropylethylamine, diisopropyl- N-propylamine, diisopropylbutylamine, diisopropylpentylamine, diisopropylhexylamine, diisopropyloctylamine, diisopropyl(2-ethylhexyl)amine, two N-butylethylamine, di-n-butyl-n-propylamine, di-n-butyl-n-pentylamine, di-n-butylbutylamine, di-n-butyl (2·ethylhexyl) n-butyl Hexylamine, & n-butylpyrrolidine, N-second-butylpyrrolidine, N-t-butylpyrrolidine, N-n-pentylpyrrolidine, N,N-dimethylcyclohexylamine, n, n_Diethylcyclohexylamine, N,N-di-n-butylcyclohexylamine, N-n-propylpiperidine, N-isopropyl group, N-positive Base sigma, N-second butyl brigade, N-t-butyl brace σ, Ν-n-pentyl piperidine, Ν-n-butylmorpholine, n-second butylmorpholine, Tributylmorpholine, Ν-n-pentylmorpholine, Ν-benzylethylaniline, Ν_benzyl propyl aniline, Ν-benzyl-Ν-isopropylaniline, Ν-Benzyl Butyl butyl aniline, hydrazine, hydrazine-dimethyl-p-toluidine, ν, Ν-diethyl-p-toluidine, hydrazine, hydrazine-di-n-butyl-p-toluidine, diethylbenzylamine , n-propylbenzylamine, di-n-butylbenzylamine, diethylphenylamine, 123766.doc -30· 200821345 di-n-propylphenylamine and di-n-butylphenylamine. + Preferred third amine (IVu) is diisopropylethylamine, ^ethyl third butylamine, diisopropylbutylamine, di-n-butyl-n-pentylamine 'N, N_di-positive Butyl % hexylamine and a third amine derived from the pentyl isomer. Particularly preferably, the third amine is di-n-butyl-n-pentylamine and a third amine derived from a pentyl isomer. Another preferred third amine propylamine having three identical groups. Particularly, the excellent pulse ion (IVv) is a plasma, wherein each of R1 to R5 is a methyl group. As particularly excellent cerium ions (IVv), n, n, n, n, N, N" hexamethyl pulsation may be mentioned. Particularly excellent choline sulfonium ions (IVW) are their ions, wherein: • RiR2 are each independently methyl, ethyl, b butyl or κ octyl and 'hydrogen, methyl, ethyl, ethyl fluorenyl , _s〇2〇H*_p〇(〇H)2; • R1 is methyl, ethyl, i.butyloctyl, r, _CH2_cH2_〇r4, and R3 and R4 are each independently hydrogen, Methyl, ethyl, ethylidene, _S020H or _P〇(〇H); or • R1 is a -ch2-ch2-〇r4 group, r, _CH2_CH2 〇r5 groups and even R5 are each independently hydrogen , methyl, ethyl, ethyl hydrazino, _s 〇 2 〇 H or -PO (OH). Particularly preferred choline sulfonium ion (IVW) is a plasma thereof, wherein: R3 is selected from the group consisting of hydrogen, methyl, ethyl, ethyl fluorenyl, 5-methoxy-3-oxapentyl, and methoxy. Dioxaoctyl, u_methoxy-3,6,9-trioxadecyl, 7-methoxy-4-oxaheptyl, methoxy-4,8-dioxa Undecane 123766.doc -31- 200821345 base, 15-methoxy-4-4,812-di-4-oxapentadecyl, 9-methoxy-5-oxadecyl, 14-methoxy-5 1〇_hydrogen-doped tetradecyl, 5-ethoxy-3-oxapentanoxy 3,6-monooxaoctyl, 11-ethoxy-3,6,9-trioxane十一十一院基乙礼基I oxaheptyl, 11-ethoxy-4,8-dioxadecene, lanthanum 15 ethoxy.4,8,12•trioxadolene , 9_ethoxy_% oxazepine and 14-acetoxime & fluorenyl-5,1〇-oxatetradecyl. In particular, its excellent scaly ion (IVx) is a plasma thereof, wherein: Ο ό • R1 to R3 are each independently an alkyl group, especially a butyl group, an isobutyl group, a 1-hexyl group or a 1-octyl group. Among the above heterocyclic cations, preferred are π-pyridinium ion, σ-pyrazolium rust ion, pyrazole rust ion, imidazoline rust ion and imidazole rust ion. Ammonium ions are preferred. Particularly preferred are 1-methylpyridine rust, ethylpyridinium, oxime-butyl)pyridinium, 1-(1-hexyl)pyridine rust, 1-(1·octylpyridinium rust, 〗 〇 _ hexyl) pyridine rust, 1-(丨-octyl)pyridine rust, 1-(1-dodecyl)pyridinium, 1_(1_tetradecyl) acridine rust, helium gas cetyl) Pyridinium, hydrazine, 2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, i-(i-butyl)-2-methylpyridyl rust, 1-(1-hexyl)- 2-methyl acridine, 1-(1-octyl)_2·decyl π-pyridinium, l (11-alkyl) 2-methyl σ ratio, 1-(1•14 Pyridyl)-2-methylu ratio σ 镔, 1-(1·hexadecyl)-2-methylpyridinium, 1-mercapto-2-ethylpyridinium, 1,2-di Ethyl acridine, ΐ-(ι_butyl)_2_ethylpyridine rust, hexyl)-2-ethyl. Bis-butyl rust, i-(1-octylethylacridinium, 1_(1_dodecanyl)·2-ethyl 吼 锈, ι_(ΐ-tetradecyl)-2-ethyl ton Bite, (1-hexadecyl)-2-ethyl-acridine rust, i,2-dimethyl-5-ethylpyridinium, 123766.doc •32- 200821345 1,5-diethyl -2-methylpyridinium, 1-(K butyl>2_mercaptoethylpyridinium, 1-(b-hexyl)-2-methyl-3_ethyl 0-pyridinium, 1-(1 -octyl)-2-methyl-3-ethylpyridinium, 丨-(1-dodecyl)-2-methyl-3-ethylpyridyl rust, (1-tetradecyl)-2 _Methyl-3_ethylpyridinium, 1_(1_hexadecyl)_2-methyl-3-ethylethyl σ疋, 1-methyl-salt, 1 ·ethyl s镔, 1 · (1 _ butyl) imidazole rust, Ml-octyl) imidazolium, 1_(1_dodecyl)imidazole rust, 1-(1-tetradecyl)imidazole rust, 1-(1 -hexadecyl)imidazole rust, hydrazine, 3_dimethylimidazolium, 1-ethyl-3-methylimidazolium rust, 丨_(bubutyl)_3_methylimidazolium, 1-(1-hexyl)- 3_methylimidazolium, octyl>3_methylimidazole rust, id-dodecyl>3-methylisoxazole, ^^tetradecyl)_3-methyl 啼君镇1-(1-16-yard methylimidazole rust, 12-dimethylnorzolium rust, ^3-trimethylisoxazole, hydrazine·ethyl-2> dimethylimidazole ore, i-(1 -butyl)-2,3-dimethyl-salt, wi-hexylmethyl-m-methane, and 丨-(1-octyl)-2,3-dimethylimidazole rust, piperid dimethyl Imidazole, 1,3,4-trimethyl odor rust, i, heart dimethyl · 3 · ethyl sputum rust, ^ ding

U-based imidazolium, Μ-dimethyl-3-octyl imidazole rust, μ, 5-trimethylimidazolium, 1,3,4,5-tetramethylimidazolium, 1 4 s-dimethyl- 3-ethyl port rice. Sitting on cesium, M,5-trimethyl-3-butylimidazolium rust and dimethyl-3-octyl imidazole (Ilia) to (mj) as described in the genus Digestion [mY, [Μ2Γ, [Μ3]+, [ΜΥ+ and [Μγ + are usually the first, second, sixth, seventh, eighth, ninth, first, u, 12 and 13 families of the 疋 周期 periodic table

Ba2+, Cr3+, Fe2+, Fe3+, C〇2+, suitable metal cations are Li'Na:, [generative cations. For example, m ...· . K, Cs+, Mg2+, Ca2+,

Nl2+, Cu2+, Ag+, Zn2+ and 123766.doc -33 - 200821345 ai3+. In the case of anions, in principle all anions can be used. For example, the anion of the ionic liquid [γρ· is selected from: • a group of ionic and halogen-containing compounds of the following formula: F_, CI·, Br-, I-, BIV, PIV, Alcv, Α1{b· ,

A13C11G·, A1BlV, Fecu·, BCU·, SbF6., AsIV, ZnCV ^ S11CI3· ^ CuCl2- ^ CF3SO3· > (CF3so3)2N- > cf3co2- > CCl3C〇2_, CN_, SCN., OCN. • Groups of sulfate, sulfite and sulfonate of the following general formula: S〇42, HS04-, S032·, HS03·, Ra〇S〇3-, RaS〇3-• Group of phosphates of the following general formula : P〇43-, HP〇42·, H2P04-, RaP042-, HRaP04-, RaRbp〇4· • Groups of phosphonates and phosphinates of the following general formula:

RaHP〇3- > RaRbP02' ^ RaRbP〇3* • Groups of phosphites of the following general formula: P〇33, HP032-, Η2Ρ03-, RaP032·, RaHP03-, RaRbp〇3-• Phosphine of the following formula Group of acid and phosphinite groups:

RaRbP〇2·, RaHPO, RaRbPCT, RaHPCT • Groups of carboxylic acids of the following general formula:

Rac〇〇- • Group of borate of the following general formula: B〇33' - HBO32' ^ H2BO3· ^ RaRbB03_ ^ RaHB〇3· ^ RaB032', B(〇Ra)(〇Rb)(〇Re)(〇 Rd)·, B(HS04)-, B(RaS〇4)· • Group of g-p-acids of the following general formula: 123766.doc -34- 200821345

RaB〇22 下歹】A group of carbonates and carboxylates of the formula: HC〇3 NC〇32- > RaC03· Group of citrate and phthalate of the following formula··Sl°4, HSi043_, H2Si042 - RRbsi〇42·, RaRbRcSi04-, HRaSi04 HRaRbSi〇4- 矽 歹 歹 歹 歹 歹 歹 歹 歹 · · · · · · · · · Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra Ra , RaRbSi〇32. R^v^Si〇• Carboxylimine, bis(sulfonyl)imine and RaRbBO· H3SiO^ 2-

RaSi043·H2RaSi04· Group: scutellaria

Ra_J^Rb-f

Ra-sf° is less than one Rb—II ° o V, 〇 VI • Group of methods of the following formula: R3—V°>-Rb~f VII, S〇2-Ra

Rb-09S

S02-Rc Group of alkoxides and aryl alkoxides of the following formula··

VIII

Rao,······················ q and r are positive integers, and s is a positive integer and indicates a complex of sulfide, sulfhydryl, polysulfide alkoxides of the following formula: polysulfide and sulfur

S, HS·, [Sv] 2·, [HSv]·, [Ras]-, where v is a positive integer of 2 to l〇; a group of staggered metal ions such as Fe(CN)63_, , Fe(C 〇)4· 〇Μη04·

Herein R, R, R and Rd are each independently of each other: hydrogen, c] _ C3 oxime, optionally substituted by one or more non-adjacent oxygen and/or sulfur atoms and/or - or multiple Or unsubstituted imine interrupted c2_c(tetra), cw14, C5_C12 cycloalkyl or 5 or 6 members containing oxygen, nitrogen and/or thia =, both of which may form together by one or more An unsaturated, saturated or aromatic ring interrupted by an oxygen and/or sulfur atom and/or one or more unsubstituted or substituted imine groups, wherein the groups mentioned herein may each additionally have a functional group , aryl I, alkyl, aryloxy, alkoxy, halogen, hetero atom and/or heterocyclic ring. Herein, the C1_C18 alkyl group optionally substituted by a functional group, an aryl group, an alkyl group, an aryloxy group, an alkoxy group, a halogen, a hetero atom and/or a hetero ring is, for example, a methyl group, an ethyl group, a propyl group, Isopropyl, n-butyl, t-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, 2,4, trimethylpentyl, decyl, ten Dialkyl, tetradecyl, hexadecyl, octadecyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, methylbutyl 123766.doc -36- 200821345 Ο

Benzobenzyl, phenylphenylethyl, α,α-dimethylbenzyl, diphenyl fluorenyl, p-phenylphenyl fluorenyl, di(p-butylphenyl)ethyl, p-chlorobenzyl , 2'4 monostyrene, p-methoxyphenylhydrazino, m-ethoxybenzyl, I cyanoethyl, 2-cyanopropyl, methoxyethylethyl, ethoxyweiylethyl, 2-Butoxycarbonylpropyl, (methoxycarbonyl)ethyl, 2-methoxyethyl, 2-ethoxyethyl '2-butoxyethyl, diethoxymethyl, diethoxy B-heart: ^-dioxolanyi group is called ^-二鸣烧一^基^-methyl-1,3-dioxolan-2-yl, cardiomethyl {3·dioxolanyl group , 2 -isopropoxy Ethyl S, 2 · Butoxypropyl, 2 - octyloxyethyl, chloromethyl, trimethylmethyl, trifluoromethyl, 1, "dimethyl 2 - chloro Base, 2-methoxypropyl, 2-ethoxyethyl, butylthiomethyl, 2-dodecylthioethyl, 2-phenylthioethyl, 2,2, 2-trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexanyl, amplyethyl, 2-aminopropyl 4_Aminobutyl, 6-aminohexyl 2-methylaminoethyl, 2·methylaminopropyl |, 3-methylaminopropyl, cardiomethylaminobutyl, 6-methylaminohexyl, 2-dimethylamino Ethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethylamino-butyl, 6-dimethylaminohexyl, 2-hydroxy-2,2 - dimethylethyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, phenoxy butyl, 6-phenoxyhexyl, 2-methoxy B Base, 2-methoxypropene|, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2 ethoxypropyl, 3 Ethoxypropyl, 4-ethoxybutyl or 6-ethoxyhexyl. Optionally, by one or more non-adjacent oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted The substituted C2_Cis_alkyl group of the imine group is, for example, 5_123766.doc •37-200821345 yl 5·oxacalyl, 14-hydroxy-5,10-oxadooxapentyl, 8-methyl Oxy-3,6-dioxaoctyltransyl-3-oxapentyl, 8-hydroxy-3,6-dioxaoctyl, u.hydroxydioxadecyl, 15- Base 4, Μ2_trioxapentadecyl, 9_ Tetraalkylammonium, 5-methoxy -3-, U- Yue group -3,6,9-three

氧oxaundecyl, 7-methoxy-4-oxaheptyl, u-methoxy-4,8-dioxa-undecyl, 15-methoxy-4,8, 12_Trioxa-pentadecyl, 9_:oxy-5-oxadecyl, 14-methoxy·5,1〇-oxatetradecyl, 5-ethyllactyl-3-oxo Heteropentyl, 8-ethoxy-3,6-dioxaoctyl, u-ethoxy-3,6,9-trioxadecyl, 7-ethoxy-4-isox Heptyl, ethoxylated-4,8-dioxadecyl, 15-ethoxy-4-,8, ΐ2_trioxapentadecaneethoxy-5-oxanonyl or When 14-ethoxy _5, ι〇_oxatetradecyl group 0, if two groups form a ring, the groups may form a fused structural unit, such as a 1,3-propyl group. , 1,4-butylene, 2_oxa], 3_propyl, oxa-1,3-propanyl, 2-oxa-π-propenyl, aza-u-extension Propylene, 1-CVC4 alkyl-1-aza-1,3-extended propylene, M-exetyl-n-alkenyl, 1-aza-1,4-extended-1,3_ Dienyl or 2_aza-M_ butyl-i,3·dienyl. The number of non-adjacent oxygen and/or sulfur atoms and/or imine groups is in principle not subject to any restrictions or is automatically limited by the size of the groups or ring building blocks. Generally, no more than five, preferably no more than four, and especially no more than three poles will be present in the respective groups. The material ' usually has at least two carbon atoms, preferably at least two carbon atoms, between the two heteroatoms. 123766.doc -38- 200821345 Substituted and unsubstituted imido groups can, for example, be imido, methylimido, isopropylimino, n-butylimido or tert-butyl Amine. The term ''functional group π' refers to, for example, the following group: carboxy, carboguanamine, carbyl, bis-(CrC4 alkyl)amine, CVC4 alkoxycarbonyl, cyano or (cyclopropenyloxy). Herein, the CrC4 alkyl group is a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a second butyl group or a tert-butyl group. Optionally, a functional group, an aryl group, an alkyl group, an aryloxy group, Alkoxy, halogen, hetero atom and/or heterocyclic substituted C0_ci4 aryl (for example) are phenyl, tolyl, diindolyl, α-naphthyl, β-naphthyl, 4-phenylbiyl, chloro Phenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, dimethylphenyl, ethylphenyl, diethylphenyl, cumene Base, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthalene , chloronaphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl 2,6-methoxy-based, 2,6-monophenyl, 4_ desert phenyl, 2- or 4-nitrophenyl, 2,4- or 2,6-dinitrophenyl, 4-dimethylamine Phenyl, 4_ethylphenylphenyl, decyloxyethylphenyl or ethoxymethylphenyl. Depending on the functional group, aryl, alkyl, aryloxy, (iv), heteroatom and/or hetero The ring-substituted cycloalkyl group is, for example, a cyclopentyl group, a cyclohexyl octyl group, a cyclodecyl group, a decylcyclopentyl group, a fluorenylcyclopentyl group, a fluorenyl hexyl yl monomethylcyclohexyl group, a diethyl group. Cyclohexyl, butylcyclohexyl, methoxy, yl, methoxycyclohexyl, diethoxycyclohexyl, butyl sul a « U chloroper hexyl 'dicyclohexyl' dichlorocyclopentyl or saturated or Unsaturated bicyclic systems, such as norborne or norbornyl. 123766.doc -39- 200821345 5 or 6 members of the oxygen, gas, I and/or sulfur heterocycles (for example) are furyl, thienyl, anthracene σ, σ, 其, 土, ϋ, 幷, benzoxazolyl, m-dioxolyl, bis, y, y, y, y, y, y Pyridinium^methyl" guanolino, dimethylpyrrolyl, decyloxyfuranyl, dimethyloxy& thiol, methyl fluorenyl, isopropyl, thiophene or third Butylthiophenyl.

Further, the anthraquinone anion is selected from the group consisting of a halide ion and a halogen-containing compound, a group of a carboxylic acid, a group of a sulfate, a sulfite, and a money root, and a group of an acid-filled group. The ruthenium anion is chloride ion, bromide ion, iodide ion, scn_, 〇cn_CN, acetate, Cl-C4 alkyl sulfate, Ra-COO·, RaSOf, RRP〇4, mesylate, tosylate, C "C4 dialkyl phosphate, hydrogen sulfate or tetra-aluminate. Particularly preferred anion is Cl., CH3COCT or CH3S〇r. It is especially preferred to use the following salts as ionic liquids: 1-methyl chloride Imidazole rust, bromomethylimidazolium bromide, cesium fluoride _ methyl imidium sputum, sputum 1-methylimidazole rust, hydrogen sulfate 1-methylimidazolium, sulfuric acid 1-methyl sulphur, sulphur Acid 1-methylimidazolium, 1-methylimidazolium sulfonate, 1-methylimidazolium diethyl ruthenate, gasified i-ethylimidazole rust, 1-ethylimidazolium bromide rust, fluorination 1 _ethylimidazole rust, cesium iodide-ethylimidazolium, strontium sulfate 1-ethylimidazolium, 1-ethyl misosulfate, methylpyrazine sulphate, 1-ethyl tosylate Imidazolium, diethylphosphonium ethyl sulphate, gasified 1-propyl sputum, desertified 1-propyl π m sigma, fluorinated 1- propyl imidazolium, 1-propyl iodide Imidazolium, sulfuric acid 1-propylimidazole rust, 1-propylimidazolium sulphate, 1-propylimidazolium methane sulfate, cesium toluenesulfonate _123766.doc •40- 200821345 imidazol rust, bismuth diethylphosphate _ propyl imidazole镔, butylbutylimidazolium chloride, desertified 1-butyl sulphur rust, fluorinated butyl butyl hydride, edebubutyl methacrylate rust, hydrogen sulphate 1-butyl imidazole rust, barium sulphate butyl imidazolium, methanesulfonic acid 1-butylimidazolium, cerium o-toluenesulfonate, butylimidazolium, diethylphosphoric acid, butylimidazolium, 2-ethyl π-pyridinium chloride, 2, ethyl σ-pyridinium bromide, iodine 2-ethylpyridinium oxime, hydrogen sulphate 2-ethylpyridyl rust, sulfuric acid 2-ethylpyridyl rust, 2-ethylpyridinium sulfonate rust, 2-ethylpyridinium tosylate, diethylphosphoric acid 2 -ethylpyridinium, chlorinated ethyl ethyl 3-pyridyl imidazolium, brominated ethyl-3-methylimidazolium, fluorinated ^ethyl-3_methylimidazolium, cesium iodide _ B ··3-methyl 啼 锈, hydrogen sulphate, ethyl _ methyl sigma quinone, barium sulfate, ethyl-3-methylimidazole rust, bismuth sulfonate 丨 _ ethyl _ 3 · methyl imidazolium, B 1-ethyl-3-methylimidazolium sulfate, thiocyanate Base_3_methylimidazolium, 1-ethyl-3-methylimidazolium toluenesulfonate, ethyl-3-methylimidazolium diethylphosphonate, 1-n-butyl-3-methylated gas Imidazolium, brominated n-butyl-3-methyl. rice bran, 1-n-butyl 3-nmethyl-imidazole rust, cesium iodide _ n-butyl _3_ fluorenyl _ σ sitting镔, acid-acid hydrogen 1-n-butyl-3-methyl-flavor α-sodium, sulfuric acid 1-n-butyl_3_methylimidazolium, yttrium methanesulfonate-n-butyl_3_methylimidazolium, 1-n-butyl 3-methylimidazole rust, toluene diethylphosphonium hydride, n-butyl-methylimidazolium chloride, n-butyl chloride -3-3-imidazole rust, bromination Butyl -3-3-ethyl sulphate, 1-n-butyl-3-ethylpyridinium fluoride, 1-n-butyl-3-ethylimidazolium hydride, 1-n-butyl sulphate 3-ethylimidazolium, 1-n-butylethylimidazolium sulfate, 1-n-butyl-3-ethylimidazolium methanesulfonate, yttrium-toluene-3-ethylimidazole Antimony and diethylphosphonium 1 n-butyl-3-ethyl imidazole rust. 123766.doc -41 - 200821345 For the purposes of the present invention, an organic money chelate is a polymer comprising a carbon atom in the main chain. The ratio of the anatomical atom of the sound contained in the main chain to the other atoms contained in the main chain is preferably at least 1:2 Å, particularly preferably at least 1:1 〇 and especially at least 1:5. According to the present invention, an early or prepolymer a1 having a crosslinking action F can be used as

The monomers and prepolymers forming the organic polymer are polymerized by polycondensation or addition polymerization. For the purposes of the present invention, the term "monomer" refers to a molecule that forms the basic unit that produces the polymer. The term "prepolymer" generally refers to a polymeric polymer, but sometimes also refers to a polymeric compound used as a precursor or intermediate in the synthesis of a polymer. According to Pure & Appl. Chem•, Vol. 66 (12) ( 1994) IUPAC recommends the terms "shrink&" and "additional aggregation" for the purposes of the present invention. For the purposes of the present invention, the term addition polymerization refers to a polymerization reaction in which a polymer is formed by repeated addition of at least a bifunctional starting material without accompanying elimination of a low molecular weight compound. For the purposes of the present invention, the term polycondensation refers in particular to the polymerization of at least a bifunctional molecule accompanied by elimination of a low molecular weight compound to form a polymer. Both polycondensation and addition polymerization are carried out step by step in separate individual reactions. Polycondensation can be used to prepare, for example, polyamines, polyesters, phenolic resins, polyethers, polyetherketones, polyethersulfones or amine based plastics. For the purposes of the present invention, all monomers or prepolymers having at least three functional groups capable of undergoing a polycondensation reaction and are well known to those skilled in the art can be used as a single cross-linking 123766.doc-42 - 200821345 Body or prepolymer a. The functional groups include -χ, _〇Η, _c〇〇H, COX, _CO〇R, -CO-O-CO-R, _N=C=〇so2ci and Ο Ο -NR'H , where r' It is H or a carbon-containing organic saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic, substituted or unsubstituted group and hydrazine is halogen 'preferably fluorine, chlorine or desert. It is also possible to use a mixture of various monomers having a crosslinking action and a prepolymer a1. According to the present invention, a reactive polycondensation resin can also be used as the prepolymer a 1 having a crosslinking action. The reactive polycondensation resin is, in particular, a resin obtainable by addition of a compound containing an amine group and subsequent condensation, and the resins can be reacted at the time of adding a hardener or at a high temperature to form a polymer having a relatively high molecular weight. It includes an amine based resin such as urea-formaldehyde resin, benzoguanamine-formaldehyde resin and melamine-formaldehyde resin or a mixture thereof. Formaldehyde and substituted and unsubstituted monohydroxy, dihydroxy and trihydric phenols (blocking females, age, children, hydrogen, S, hydroxy, benzene, benzene, benzene, benzene) The condensate of the group can also be used as a reactive polycondensation resin. For the purpose of the present invention, it is preferred to use a reactive polycondensation resin as the monomer or prepolymer a1 having a crosslinking action. It is especially preferred to use a melamine-furfural resin or a urea-formaldehyde resin or a mixture thereof as the prepolymer a. It is also preferred to use a monomer having a crosslinking action and a prepolymer a1 according to the invention, the polymerization of which produces polyethersulfone (PES) and polyetherketone (PEK), particularly preferably polyaryl ether ketone and poly Aryl ether sulfone. The polyaryl ether ketone comprises a phenyl group bonded by an ether and a ketone group. Depending on the number and order of hydrazines and ketone groups present in the basic structural unit, polyether ketone (pEK) is also known as PEEK, PEEKEK, PEKK, etc.; where K is a keto group and E is an ether 123766.doc -43- 200821345 Base. For example, PEK can be obtained by condensing a phenol component with a benzophenone derivative. The desired component typically has at least two OH groups bonded to at least one aromatic group, and, for example, hydroquinone, bis(4.hydroxyphenyl)ether, phloroglucinol, bisphenol A, C And F, ι, ΐ, ΐ-gin (4-hydroxyphenyl)ethane and hexafluoroisopropylidenediol are used as the phenol component. Hydroxyaryl ketones are also suitable. The benzophenone derivative has at least one element (such as F, CM, Br or I) on each of the two phenyl groups. For example, 4,4,·difluorobenzophenone and

4,4'-Dichlorobenzophenone was used as the benzophenone derivative. The benzophenone derivative may also have an OH group instead of a halogen group. K may also be prepared by condensing an aromatic dicarboxylic acid chloride with a diphenyl ether in the presence of a Friedei_Cnfts catalyst, or a diphenyl ether containing a carboxylic acid chloride group. Used for this purpose. Similarly, a polyether can be prepared by polycondensing a phenol component with an aromatic compound. All of the above-mentioned compounds of the desired component can be used as a desired component. At least dihalogenated and comprising at least two Phenyl sulfones such as bis(4-ranyl)sulfone and bis(4-chlorophenyl)sulfone are used as the aromatic halide. Another phenol component that can be used is bis(4-hydroxyphenyl)sulfone. The above-mentioned early bodies may have other substituents on the benzene ring, such as a stone-based group and a dentate group (such as F, CM, Br, and I). , the poly-mouth can be used to prepare, for example, polyamino phthalate, polyurea or epoxy. According to the present invention, it can be subjected to addition polymerization and is familiar with the technology::: all monomers or pre-known The polymer is used to prepare a conductive polymer paste. : a monomer or prepolymer having at least three groups: -OH, 123766.doc -44 - 200821345 _COOH, _COX, _c〇〇R, -HCO, _RfCO, -NR, H, -N= C = 0 or an epoxy group, wherein R is H or a carbon-containing organic saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic, substituted or unsubstituted group and X is a functional group The prime 'is preferably chlorine or bromine. It is also possible to use a mixture of various suitable monomers or prepolymers to form a copolymer.

According to the invention, the individual monomers or prepolymers a1 having cross-linking may each have the same functional group, so that it is generally necessary to use at least two types of monomers or prepolymers, in which case the AA component and the BB The components are combined to form a cross-linked pi[-AA-BB]n polymer; or the functional group contained in the monomer or prepolymer d having cross-linking may be different, in which case only one type of early body is used. Or a prepolymer is sufficient. In this case, the crosslinked [_ΑΒ]η polymer is obtained from the oxime component. According to the invention, however, other types of monomers or prepolymers can be used in each case. According to the invention, the polymer which swells in the ionic liquid is chemically crosslinked, i.e., crosslinked via a covalent bond. The presence of at least one component having cross-linking can cause cross-linking. Molecules with more than two functional groups typically have cross-linking in addition polymerization and polycondensation. The monomers and prepolymers a1 used according to the invention have a crosslinking effect: they have at least 3 functional groups. The right-handed material additionally uses a monomer having no cross-linking action and a prepolymer a3: which usually contains two functional groups, which can be polymerized by polymerization or polycondensation to polymerize the energy group with the cross-linking component. . The above description regarding the choice of the precursor or prepolymer a1 having a cross-linking is applicable to the choice of the monomer or prepolymer a3 which is not used, the difference being that the component U has no softening effect and It usually has only two functional groups. 123766.doc -45- 200821345 ...the functional group contained in component a3 may be the same functional group as the energy group contained in component u used, but the component coffee may also have different functional gum steps. b) Polyorganisms Γ Electrical organic polymerization should be. The "selected mechanism (addition polymerization or polycondensation) is opposite to each other: According to the invention, the end of the monomer unit having cross-linking effect in the organic polymer is 0/, ^ in the total weight of the polymer. It is 1 weight, preferably 10 weights, particularly preferably 30% by weight. In the present invention, f) in the embodiment of the human body, the organic I 5 00 weight I% has cross-linking The monomer unit that acts. According to the invention, the conductive organic polymer gel comprises from 3 to 90% by weight of the group of people by step b). Further, in the organic polymer, preferably from 5 to 80% by weight of the organic polymer, particularly preferably from 1 G to the % by weight of the organic polymer. Pots = methods known to those skilled in the art for polycondensation and addition polymerization. Two: Hunting is initiated by the addition of a catalyst or by heating or photochemical methods. The polymerization of the monomers and prepolymers used under the various conditions will be adapted and used as a catalyst. In the presence of a mixture of ionic liquids or a plurality of ionic liquids in the solution provided in step a), the polymerization of a: and a, if appropriate, a3 forms a crosslinked organic polymer. By crosslinking or force polymerization to cause the component to "polymerize with (if appropriate) U to form a mixture of crosslinked organic poly-A probiotic liquid or a plurality of ionic liquids swelled in a mixture of a raw liquid or a plurality of ionic liquids. And the organic polymer which is swelled in the middle and the sixth organic polymer will be collectively referred to as a conductive organic polymer glue. According to the formula of the present invention, X addition or polycondensation can be carried out similarly to the sol-gel method according to the present invention. Mixing an ionic liquid or a mixture of a plurality of ionic 123766.doc -46-200821345 liquids as a solvent. The monomer or prepolymer having a crosslinking effect and (if appropriate) are not crosslinked. The component a3 is dissolved or suspended in an ionic liquid, that is, polymerization is initiated by heating, adding a catalyst or photochemically, forming a small "box, oligomer, such oligomer which can be formed initially. It exists in the form of chain, % or even internal three-dimensional cross-linking. For the purpose of the present invention, the family is different from other conventional cold-type museums, and other whites, but it is obtained at the end of the initial reaction. Crosslinked polymer The molecular weight of the precursor object of the present invention in terms of 'comprises such a "cluster " of a homogeneous solution or a colloidal sol referred to.

As the reaction progressed, the Rong "Wei" took a set of I Temple to form a three-dimensional crosslinked gum starter. For example, S.A. vista (4) a. Rmer, A# is purchased from Η (2〇〇3) 1〇M14 for organic solvents or water between benzodiazepine-make resin. In a typical sol-gel process, a sol is prepared by hydrolyzing a precursor molecule. According to the invention, hydrolysis preferably does not occur prior to polymerization. / According to the present specification, the catalyst for forming a sol may be different from the catalyst for forming a polymer paste, if appropriate. If the prepolymer is used as the component U of the polymer gel of the present invention, the solution solution of the prepolymerized = (tetra) or a mixture of the plurality of ionic liquids may be a sol in the sense of the above method, so that Here, the method similar to the sol-gel method starts directly from the sol. According to the invention, the reaction time for the polycondensation or polyaddition polymerization is less than 12 hours, preferably less than 9 hours, especially less than 6 hours. Combinations of the preferred embodiments in accordance with the present invention are also preferred. The invention further provides a method of preparing a conductive organic polymer knee, wherein 123766.doc -47-200821345 comprises the steps of: a) providing a solution comprising: -, having one or more monomers or a a mixture of a ionic liquid or a plurality of ionic liquids, = if appropriate, at least one component which does not have a crosslinking effect, b) fine: in the presence of a mixture of an ionic liquid or a plurality of ionic liquids

The polycondensation or addition polymerization of Lj causes the component a1 to be polymerized with (if appropriate) component d to form an organic polymer. According to the present invention, a conductive organic polymer paste can be used as the solid electrolyte. The conductive organic polymer glue is preferably used as a battery, a current element, or a solid electrolyte in a battery pack or a fuel cell. The present invention also provides an electric storage battery, a current element, a portable battery pack or a fuel cell as an electrolyte. The present invention further provides a method of producing a naphtha polymer foam from the electroconductive organic polymer gel of the present invention by substituting an ionic liquid with an organic solvent and then removing the organic solvent. Depending on the type of polymer and the size of the sample, 右 (right appropriate) can be achieved by multiple treatments with an organic solvent. It is especially preferred to remove the solvent at atmospheric pressure and room temperature, as in the case of human I.戍 The organic solvent used to displace the ionic liquid in the nanoporous polymer foam produced from the conductive organic polymer gel of the present invention is at 120 C under atmospheric pressure. Examples of such suitable organic solvents are linear or branched hydrocarbons having from 1 to 6 carbon atoms, especially pentyl, hexane or heptane. Particularly preferred solvents are tetrahydrofuranacetone, methyl ethyl ketone, ethyl acetate and 123766.doc -48-200821345 chloroform. Nanoporous polymer foams with higher total pores available after drying. nm to 1 μ μηη range The gap ratio and its associated low density. The pore size is within the present invention. The present invention further provides a nanoporous polymer foam which can be produced by the above method. [Embodiment] The present invention is explained below by way of examples. C'

The porosity of the polymer foam formed after removal of the ionic liquid is measured by means of mercury porosimetry according to DIN 66133. The conductivity was measured using a 4-point measurement battery with a gold electrode. The distance between the gold electrodes is cm and the width of the electrodes is 2 cm. The ohmic resistance was measured by means of an impedance spectrum (Zahne EM 6 ix potentiostat/impedance analyzer) at a frequency of 〇 1 MHz at room temperature. Conductivity was calculated from ohmic resistance and sample geometry. Example 1 A 2% by weight solution of a reactive melamine-formaldehyde resin (a ratio of melamine/formaldehyde of L1.5) to ethyl acesulfate 1 ethyl-3-methylimidazolium was prepared at room temperature. Formic acid was added to the mixture in an amount corresponding to a weight ratio of the reactive resin to the acid of 2.5. The reaction was allowed to proceed at 6 (rc for 3 hours. The formed conductive organic polymer gel was introduced into an excess of propylene g to displace the ionic liquid. The polymer gel was then dried at room temperature. Pore size distribution (1) shows In Figure 1. The X-axis (X) shows the pore size in nm, while the γ-axis (γ) shows the logarithm of the difference pore volume in ml/g. The pore size distribution (1) is about 123766.doc - 49- 200821345 The maximum value is shown at 200 nm. The obtained polymer foam has a large number of pores (1.3 ml/g) with a diameter of less than 1000 nm. The porosity is defined as the ratio of pores to the total volume, which is 70%. Example 2 Preparation of a mixture of reactive oxysulfate diamine-carboxylic acid resin (melamine/formic acid ratio of 1.5·1.5) in ethylsulfonic acid ethylmethylimidazolium to correspond to reactive resin and acid The formic acid was added to the mixture in a weight ratio of 2.5. The reaction was carried out at 6 (rc for 3 hours. The conductivity of the polymer gel obtained under it was 46 mS/cm. The gel was allowed to stand in excess acetone for 12 hours at room temperature, thereby first replacing the organic conductive polymer gel. Ionic liquid. The mixture was then placed pentane Shu was allowed to stand at the same temperature for 2 hours

Ηηι. The porosity is 80 〇 / 〇. Separation of pentane [Simple description of the diagram]

Figure 2 shows the pore size distribution of the polymer obtained as described in Example 2. The pore size distribution of the polymer. 123766.doc • 50 -

Claims (1)

200821345 X. Application for patent scope·· A conductive organic polymer gel, a) providing a solution comprising the following: which can be prepared by the following steps a• cross-linking- or a plurality of monomers or prepolymers, a2. a sub-liquid or a plurality of ionic liquids, : 3. right appropriate 'at least - a component without cross-linking b) by: the presence of an ionic liquid or a mixture of a plurality of ionic liquids, broad or addition polymerization such that component a 1 is polymerized with the appropriate component a3 to form an organic polymer. 2. The conductive organic polymer gel of claim 1, wherein the ionic liquid system is selected from the group consisting of an anion and a cation salt of the formula (1). [AJnMn~ (I), :,,, 2, 3 Or 4'[A] + is a tetraammonium cation, a gas cation, a 'cation or a scaly cation and [γ is a monovalent, di-tetravalent anion; a mixed salt of the formula or formula (II): [A] [A ] [Y] (Ha), where n=:2 ; [AWrtAYmn· (10)), where n=3; or (IIc), where n=4, where [AT, [AY, [八亇 and [AY] The lines are independently selected from the group referred to in [A Guanghu and the [Y]n- system is as defined above; or the mixed salt of the formula (III): [AHAYtAYCMM + CY-wide (Ilia), where n= 4 ; [A1] + [A2] + [M1] + [M2] + [Y]n- (Illb), where n=4 ; 123766.doc 200821345 [α^μ^μΥευ]11· [Αι] + [ Μιγ[Ύ]η' [aYcmJImY+cy]11- [Α1] + [Μ5]3 + [Υ]η· [Αιγ[Μ4]2^[Υ]Ώ' (lllc) , where η=4 ; (llld Where η = 3 ; (Hie), where η = 3; (lllf) , where η = 2 ; (lllg) , where η = 4 ; (lllh) , where η = 4 ; (llli) , where η = 4; or 〇 (Illj), wherein η=3, wherein [AY, [α2]+ and [α3γ are independently selected from the group referred to as [Α]+, mn- is as defined below with respect to formula (1), and [ Ml]+, [Μ2]+, [MY is a monovalent metal cation, [μ4]2+ is a divalent metal cation and [Μ5]3+ is a trivalent metal cation. 3. The conductive organic polymer gel of claim 1 or 2, wherein the ionic liquid comprises at least one 11⁄4 ion selected from the group consisting of cations of the formulae (IVa) to (IVy): 123766.doc 200821345 123766.doc 200821345 R _丨) R\ /R (IVq·) (IVt) R1\,^/〇r3 R (IVw) 123766.doc (IVx) (ivy) 200821345 and oligomers comprising the same, wherein the group R is hydrogen or has from 1 to 20 carbon atoms a carbon-containing organic saturated saturated, acyclic or cyclic, aliphatic, aromatic or if aliphatic group which may be unsubstituted or substituted with 1 to 5 atom or functional group interrupted or substituted; and the groups R to R each Carbon-containing organic saturated or unsaturated, acyclic or cyclic, independently hydrogen, rhein or having a carbon atom of 20 carbon atoms and which may be unsubstituted or interrupted or substituted by 1 to 5 heteroatoms or a fatty, aliphatic, aromatic or araliphatic group, wherein the group bonded to a carbon atom in the formula (IV) described above may additionally be a dentate or a functional group; or from R Two adjacent groups of the group consisting of R may also form a diterpene, carbon-containing organic saturation having from 1 to 30 carbon atoms which may be unsubstituted or interrupted or substituted by up to 5 heteroatoms or functional groups. Or an unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic group. 4. The conductive organic polymer gel of claim 2 or 2, wherein the ionic liquid comprises at least one anion selected from the group consisting of: a halide ion of the following formula and a compound containing _: F., Cl ·, Br·, I·, Bf4·, PF6-, Alcv, Al2C1/, A13C110-, AlBiV, FeCl4., BCl, SbF6-, AsF6·, ZnCl3·, SnCV, CuCV, CF3S03·, (Cf3S〇3 2N-, cf3co2-, CC13C02·, • Cyanate, thiocyanate and isocyanate of the following formula: CN-, SCN, OCN·, 123766.doc 200821345 • Sulfate, sulfite and sulfonate of the following general formula Acid radicals: so42·, hso4-, so32., hso3-, Raoso3-, • phosphates of the following general formula: p〇43-, hpo42-, H2P〇4-, RaP〇42· RaRbPO, • Phosphonate and phosphinate: RaHP03_, RaRbP02, RaRbp〇3·, • Phosphite of the following formula: P〇33', HP〇32·, H2PO3', RaP〇32· RaRbP03_, • Phosphine of the following formula Acid and phosphinate: RaRbP02·, RaHP02·, RaRbPCT, RaHPO-, • Carboxylic acids of the following general formula: Racocr, • Borate: B〇33., HB〇32·, H2B03-, RaRbB03-RaB032·, B(ORa)(〇Rb)(〇RC)(〇Rd)·, B(RaS04)-, •The following formula _Acetate: RaB022-, RaRbBCT, • Carbonate and carboxylic acid vinegar of the following formula: HCCV, C032-, RaC (V, • Lithium sulphate of the following formula and oxalic acid 曰 SiO, HSi043- , H2Si〇42·, H3Si04·123766.doc RaSCV, HRaP〇/, , RaHPCV, , RaHB03-, B(HS04)', , RaSi043·, 200821345 RaRbSi〇42-, RaRbRcSi〇4-, HRaSi〇42- , HRaRbSi〇4-, 4 alkyl decane salts and aryl sulfonium salts of the following formula: curry, RaRbSi022·, RaRVSi〇-, RaRbRCsi〇, RaRbRcSi〇2_, RaRbSi032, carboxamide of the following formula Imine, bis(sulfonyl) quinone imine and sulfonimide: C. Methyl compounds of the formula: S〇2-Ra I . Rbo2s〆, so2-rc VIII, • alkoxides and aryl alkoxides of the formula Racr, a metalloate of the following formula: [MqHalr]s-, wherein Μ is a metal and Hal is fluoro, chloro, hydrazine or hydrazine, ... is a positive integer and indicates the stoichiometry of the complex, and s is a positive integer and indicates the charge on the complex; 3 ^ Sulfur ions, sulfur radicals, polysulfide ions, polysulfide gas radicals and thiolates of the following general formula: S ·, HS·, [Sv] 2_, [HSV]-, [RaS]·, where v is 2 to a positive integer of 1〇; and Fe(CN), Mn〇4• and • a mismatched metal ion such as Fe(CN)63· 123766.doc 200821345 ί^((:0)4~, where RR, R and Rd each independently of each other is hydrogen, c _c p, optionally via - or a plurality of non-adjacent oxygen and/or sulfur atoms and/or 8:: a plurality of substituted or unsubstituted imine groups are interrupted 'Family-based, c-based, c5-Cl2 ring-based or 5- or 6-membered oxygen, nitrogen and/or sulfur heterocycles, "in the middle can form a visible condition - or multiple oxygen and Or an unsaturated, saturated or aromatic ring interrupted by a sulfur atom S or a plurality of unsubstituted or substituted imine groups, wherein the groups such as the ancient cages can be additionally functional groups and aromatic groups. Base, alkyl, aryloxy, alkoxy, i, 5. The conductive organic polymer gel of claim 1 or 2, wherein the cation is selected from the group consisting of mono- or poly-substituted (tetra) phosphonium ions and (iv) phosphonium ions, wherein The substituents are each independently of each other a straight or branched alkyl group having m carbon atoms. 6. The conductive organic polymer gel of claim 1 or 2, wherein the ionic liquid system is selected from the group consisting of Group · · 1-methyl miso chloride! Weng, bromide, methyl hydrazine, gasification in imidazolium, 1-methylimidazolium iodide, methyl imidazolium sulphate, 1-methyl sulphate , methanesulfonylmethyl (tetra)pyrene, toluene acid u-imidazole rust, diethyl phosphonium-methylimidazolium, gasified hydrazine _ethylimidazolium, brominated 1-ethylimidazole rust, cesium fluoride _B Imidazolium 碘 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基 乙基Base acid 1-ethylimidazolium, gasified hydrazine-propylimidazolium, cesium bromide _propyl 123766.doc 200821345 meters on 13⁄4 ratified 1-propyl Scented, moth-like 1-propyl-taste τι iron, hydrogen sulphate 1 · propyl imidazolium, barium sulfate propyl imidazolium, methane sulfate 丨 propyl imidazolium, toluene sulfonic acid propyl imidazole rust, Diethyl phosphonium hydrazide propyl propyl thiolate, chlorinated 1-butyl imidazole rust, cesium bromide _ butyl imidazolium, fluorinated ^ butyl taste. Sitting 蛾, moth 1 _ butyl taste, Bismuth hydrogen sulfate _ butyl sulphate, 1-butylimidazolium sulfate, methanesulfonic acid butyl butyl sulphide, 1-butylimidazolium toluene sulfonate, bismuth diethyl ruthenate butyl methacrylate rust, chlorination 2_ethyl 吼 镔, 2-ethyl acridinium bromide, 2-ethylpyridinium iodine, thiol hydrazine IL 2-ethyl 吼 镔 镔 镔, sulfuric acid 2 _ ethyl ^ ratio σ 镔, ethylpyridinium methanesulfonate, 2-ethylpyridinium tosylate, 2-ethylpyridinium ruthenium sulphate, gasified 1-ethyl-3-methylimidazolium, cesium bromide Ethyl_3_methylimidazole rust, 1-ethyl-3-methylimidazolium fluoride, ruthenium osmium_ethyl-3-methylimidazolium, hydrogen sulfate 1-ethyl_3·methyl Salix, sulfuric acid ^ethyl_3_nonylimidazolium, 1-ethyl-3-methylimidazolium sulfonate, ethylsulfate^ethyl_ 3-mercaptoimidazolium, thiocyanate^ethyl_3_methylimidazolium, 1-ethyl-3-methylimidazolium toluenesulfonate, bismuth diethylphosphonate·ethyl_3_methylimidazole Rust, gasification of 1-n-butyl-3-methylimidazolium, cesium bromide, n-butyl _3_mercaptoimidazole rust, 1-n-butyl-3-methylimidazolium fluoride, cesium iodide _ n-Butyl-3-methylimidazolium, 1-n-butyl 3-methylimidazolium sulfonate, 丨-n-butyl-3-methylimidazolium sulphate, yttrium-n-butyl sulfonate _3_ mercapto imidazole rust, 1-n-butyl-3-methylimidazolium sulfonate sulfonate, diethylphosphoric acid n-butyl-3-indolyl hydrazide, 1-n-butyl _3_B Imidazolium, ruthenium bromide-n-butyl-3-ethylimidazole rust, cesium fluoride-n-butyl-3-ethylimidazolium, iodide, n-butyl-3-ethylimidazole rust, hydrogen sulfate 1ββ-n-butyl_3_ethylimidazole rust, 123766.doc 200821345 1-n-butyl-3-ethylimidazolium sulphate, butyl-butyl sulfonate _3_ethylimidazolium, sulfonate sulfonate The base _3_ethylimidazolium and diethylphosphonium bromide _3_ethyl P m α are misplaced. 7. The conductive organic polymer gel of claim 1 or 2, wherein at least one of the polymers is polymerizable by polycondensation or addition polymerization and comprises at least three selected from the group consisting of -OH, -CO〇H, -C〇x, _c〇〇R,, _c〇〇_c〇r,, #〇〇, -S〇2C1, _Hc〇, Rt(3)...nr'h or an epoxy group and also having a functional group of -X in the polycondensation state a cross-linking compound as an early or prepolymer a, wherein R is a hydrazine or a carbon-containing organic saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic, substituted or unsubstituted The group is again _, preferably chlorine or bromine. 8. The conductive organic polymer gel of claim 1, wherein a reactive polycondensation resin is used as the prepolymer a1. 9. The conductive organic polymer gel of claim 8, wherein melamine-methyl resin or urea-make resin or a mixture thereof is used as the reactive polycondensation resin. 10·= The conductive organic polymer gel of the invention, wherein the polymer wins “3 to 9 Gwt% of the polymer obtained by the polymerization of the step b). / U·: Conductive organic polymerization of claim 1 or 2 The knee, wherein the concentration of the monomer unit in the polymer and having a cross-linking amount is 1% by weight based on the total weight of the polymer. 1:: A method for preparing a conductive organic polymer gel, which comprises a step ^ a) Providing a solution containing the following: 123766.doc 10 200821345 2 1. One or more monomers or prepolymers with a parental effect, 'ionic liquid or a mixture of multiple ionic liquids, a3. If appropriate, one is less than one component that does not have a cross-linking effect, b) is obtained by polycondensation or addition in the presence of a mixture of ionomers, butyl liquid or a plurality of ionic liquids. Component a 1 is polymerized with the appropriate component a3 to form an organic polymer. 13 • The method of claim 1, the electrical organic polymer gel, which is used as solid electrolyte 14 • The conductive current component of claim 1 (Solid electrolyte in galvanic. ^ Raw organic polymer It is used as a battery element, a portable battery pack or a fuel cell. 15. A human current component, a portable battery pack or a fuel cell, and a conductive organic polymer gel of '1^1 as an electrolyte. Conductive, multi-agglomerating & gum of the claim item, which is used for the manufacture of a nano-polymer foam. The conductive organic polymerization of the method 1 of the non-porous porous polymer foam ϋ 求 ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ Method 123766.doc