Semiconductor organic compound, synthesis method thereof, use thereof and electronic functional element

FIELD: chemistry.

SUBSTANCE: invention describes a neutral semiconductor organic compound of formula (I) , where R1 and R2 denote a hydrogen atom, n is the number links in formula (I) and is an integer between 2 and 1000, terminal groups of the compound R3 and R4 denote a hydrogen atom or a linear or branched alkyl group with 1-20 carbon atoms. The invention also describes use of the said compound as a semiconductor in electronic functional elements.

EFFECT: higher oxidation resistance, which enables use of the compound in transistors and other electronic functional elements.

5 cl, 3 ex

 

The invention relates to molecular electronics, in particular the organic semiconductor compound, the method of its production, to its use and to the electronic functional element.

The field of molecular electronics has been evolving rapidly in the last 15 years with the opening of the organic conducting and semiconducting compounds. At this time, we found a large number of compounds which have electro-optical properties and properties of semiconductors. It is clear to all that molecular electronics will not replace conventional semiconductor functional elements based on silicon. Instead, assume that molecular electronic functional elements will discover new applications, where demand can be applied to large surfaces, structural flexibility, the possibility of processing at low temperatures and low cost. Currently, semiconductor organic compounds are being developed for such applications as organic field-effect transistors, organic luminescent diodes, sensors, and photovoltaic elements. Due to the simplicity of structure and integration of field-effect transistors in integrated organic semiconductor circuits become possible low-cost solutions for smart cards or zenni is s, who until recently it was impossible to implement based on silicon technology due to cost and lack of elasticity of the silicon functional elements. Similarly, organic field-effect transistors can be used as switching elements in a flexible matrix screens with a large surface. Overview on organic semiconductors, semiconductor integrated circuits and their application are presented, for example, in Electronics, 2002, Vol 15, ñ.38.

Known organic semiconductor compounds are, for example, polyfluorene and such fluorenone copolymers, such as poly(9,9-dioctyl-fluorene-with-Bethoven), with values of mobility of charges for their speakers, then will also be used short term mobility, up to 0.02 cm2/·With (Science, 2000, Vol 290, s). On regioregular poly(3-hexylthiophene-2,5-diele) received even mobility up to 0.1 cm2/B·(Science, 1998, Vol 280, s). Other members of the semiconducting organic compounds are, for example, oligothiophenes, in particular the oligothiophenes with terminal alkyl substituents, and pentacene. Typical values of mobility, for example, α,α'-dihexyl quater-, -quinque and-sexy-thiophene are in the range from 0.05 to 0.1 cm2/·C. However, the above connection is only conditionally suitable PlaysForSure in (opto)electronic functional elements. For example, some of these compounds are characteristic of phase transformations, which preclude their use at temperatures exceeding defined for each individual compound the temperature, or their mobility is insufficient for some applications.

There have been numerous studies on preparation of oligomers of alkylenediamines structural units, in particular 3,4-ethylenedioxythiophene structural units, and their use as organic semiconductors. However, the disadvantage of these oligarchisation, in particular the corresponding 3,4-ethylenedioxythiophene compounds is too high propensity for oxidation. For this reason, they can only partially be used as organic semiconductors as possible subsidizing organic semiconductor affects the modulation current. Only recently been described Roncali and others, Journal of Organic Chemistry, 2003, 68, 5357-5360, syntheses of oligo(3,4-ethylenedioxythiophene), which are characterized by reduced sensitivity to oxidation. However, data on this connection, regarding its suitability for use as organic semiconductor in transistors or other (opto)electronic functional elements, up to now absent.

In connection with the presentation is authorized there is still a need for compounds, the which can be used as organic semiconductors.

In accordance with this, the goal was to get new semiconducting organic compounds, which are less sensitive to oxidation and are well suited for use as organic semiconductor in (opto)electronic functional elements.

Unexpectedly, it was found that neutral, i.e. not being in oxidized form, compounds containing 3,4-methylenedioxyphenol structural units, then the simplified version, but in the same value they will be methylendioxyphenyl structural units, largely resistant to oxidation and can be used as semiconductors.

The object of the present invention is a semiconductor organic compound containing the same or different recurring structural units of the General formula (I), which may include the same or different recurring structural units of the General formula (II)

where

R1and R2independently from each other mean a hydrogen atom, a linear or branched unsubstituted or substituted alkyl group with the number of carbon atoms from one to twenty, the chain of which may be the Elena atoms of oxygen and/or sulfur number from one to five, partially fluorinated or perfluorinated linear or branched alkyl group with the number of carbon atoms from one to twenty, linear or branched oxyalkylene group with the number of carbon atoms from one to twenty, unsubstituted or substituted aryl group with the number of carbon atoms from six to twenty-four, unsubstituted or substituted alcylaryl group with the number of carbon atoms from six to twenty-four, unsubstituted or substituted axially group with the number of carbon atoms from six to twenty-four or unsubstituted or substituted heteroaryl group with carbon atoms from two to twenty-four, also together denote unsubstituted or substituted linear or branched alkylenes group with the number of carbon atoms from one to twenty, the chain of which may be separated by oxygen atoms and/or sulfur number from one to five, dioxyalkylene group with the number of carbon atoms from one to twenty, dialkylanilines group with the number of carbon atoms from six to thirty or deoxyadenosyl group with the number of carbon atoms from six to twenty-four

X1means unsubstituted or substituted vinylidene, arylidene or heteroarenes structural unit,

the number of recurring structural units of the General formula (I) is avno n, and the number of recurring structural units of the General formula (II) is equal to m, and

n means an integer from 1 to 1000, in the preferred case from 1 to 200,

m means an integer from 0 to 1000, in the preferred case, from 0 to 20,

the minimum sum of n and m is equal to 2, in the preferred case, it is equal to an integer from 2 to 2000, in the most preferred case, the amount equal to the whole number of from 3 to 220,

this connection is also end groups R3and R4and

R3and R4independently from each other mean a hydrogen atom, a linear or branched alkyl group with the number of carbon atoms from one to twenty, partially fluorinated or perfluorinated linear or branched alkyl group with the number of carbon atoms from one to twenty, linear or branched oxyalkylene group with the number of carbon atoms from one to twenty, unsubstituted or substituted aryl group with the number of carbon atoms from six to twenty-four, unsubstituted or substituted alcylaryl group with the number of carbon atoms in the alkyl residue of from one to twenty, unsubstituted or substituted axially group with the number of carbon atoms from one to twenty or same unsubstituted or substituted heteroaryl group with carbon atoms of from one to twenty.

The asterisk (*) in the form of ulah I and II in each case indicates the place of attachment of neighbouring groups or end groups of R 3or R4.

Corresponding to the invention compounds are polymers. In the framework of the invention, the term polymer refers to all compounds for which the sum of n and m is an integer more than 1. In addition, the polymers are all such compounds, which are polydisperse, i.e. they have a distribution of molecular masses, or monodisperse, that is characterized by a single value of molecular weight. In fact presents definitions preference is given to the relevant invention monodisperse compounds. Corresponding to the invention compounds may be homopolymers of the same recurring structural units of the General formula (I) or copolymers of several different recurring structural units of the General formula (I) or several identical or different recurring structural units of the General formulas (I) and (II). However, the repeated structural unit in the copolymer can be located statistically, alternating or block. In the framework of the invention the concept of recurring structural units applies to all structural units of the General formulas (I) and (II) regardless of how many times they occur in polymers - once or multiple times.

The term "substituted" refers, unless otherwise specified, to the replacement by the group from a number of: an alkyl group, particularly an alkyl group with the number of carbon atoms of from one to six, cycloalkyl group, in particular cycloalkyl group with the number of carbon atoms from six to fourteen, aryl group, in particular aryl group with the number of carbon atoms from six to twelve, arylalkyl group, in particular arylalkyl group with the number of carbon atoms from seven to fourteen, halogen, in particular fluorine, chlorine, bromine and iodine, oxyalkylene, axially, ether, thioester, disulfide, sulfoxide, sulfonic, sulfate group, amino group, aldehyde group, ketogroup, the functional group of ether carboxylic acids, carboxylic acid, carbonate, carboxylate group, cyano, alkylsilane and alkoxysilane group, and carboxylamide group.

In the preferred case, R1and R2in the General formula (I) independently of one another mean a hydrogen atom, such linear or branched unsubstituted or substituted alkyl group with the number of carbon atoms from one to twenty, the chain of which may be separated by oxygen atoms and/or sulfur number from one to five, as, for example, metal, ethyl, n-sawn, ISO-propyl, n-boutelou, second-boutelou, isobutylene, tert-boutelou, n-pentelow, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropylene, 1,2-dimethylpropylene, 2,2-dimethylpropylene is, n-hexoloy, n-heptylene, n-aktiline, 2-ethylhexyloxy, n-naniloa, n-decile, n-undecyloxy, n-dodecyloxy, n-tridecanol, n-tetradecanol, n-hexadecanol, n-octadecyl or n-akosile group, such partially fluorinated or perfluorinated linear or branched alkyl group with the number of carbon atoms from one to twenty, as, for example, triptorelin, pentatration, heptafluoropropyl, nonafterburning, performanceline, performanceline, perforation, perperoglou, performancenow, perfonally, perperoglou, performanceline, performanceline, performermarilyn, performanceduring, pertrochemical, perforacion group, such linear or branched oxyalkylene group with the number of carbon atoms from one to twenty, as, for example, a methoxy group, ethoxypropan, n-propoxylate, isopropoxy, n-butoxypropyl, isobutoxy, sec - or tert-butoxypropyl, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3 methylbutoxy group, 1-ethylpropoxy, 1,1-dimethylpropyleneurea, 1,2-dimethylpropylene, 2,2-dimethylpropyleneurea, n-hexyloxy, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy the PPU, n-dodecyloxy, n-tridecylamine, n-tetradecylammonium, n-hexadecyloxypropyl, n-octadecylamine, n-nonacetylated or n-actinograph, such unsubstituted or substituted aryl group with the number of carbon atoms from six to twenty-four, as, for example, phenyl, naftalina, untilnow, methylphenylene, ethylvanillin, pentylphenol, butylaniline, dimethylaniline, biphenylyl group, such unsubstituted or substituted alcylaryl group with the number of carbon atoms from six to twenty-four, as, for example, benzyl group, such unsubstituted or substituted axially group with the number of carbon atoms from six to twenty-four, as, for example, fenoxaprop, or such unsubstituted or substituted heteroaryl group with carbon atoms from two to twenty-four, as, for example, 2-thienyl, 3-thienyl, 2-fornillo, 3-fornillo, 2-pyrrolidinyl, 3-pyrrolidinyl, pyrazolidine, thiazolidine, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy, hyalinella, oxazolidinyl and thiazolidine group, or together denote unsubstituted or substituted alkylenes group with the number of carbon atoms from one to twenty, chain which can be separated by oxygen atoms and/or sulfur number from one to five, for example 1,2-ethylene, 1,3-propylidene, 1,4-butyl who denovo, 1,5-pentylidene, dioxyalkylene group with the number of carbon atoms from one to twenty, dialkylanilines group with the number of carbon atoms from six to thirty, for example 1,2-xylidene group, or deoxyadenosyl group with the number of carbon atoms from six to twenty-four.

In the preferred case, R3and R4in the General formula (I) independently of one another mean a hydrogen atom, such linear or branched alkyl group with the number of carbon atoms from one to twenty, as, for example, methyl, ethyl, n-sawn, ISO-propyl, n-boutelou, second-boutelou, isobutylene, tert-boutelou, n-pentelow, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropylene, 2,2-dimethylpropylene, n-hexoloy, n-heptylene, n-aktiline, 2-ethylhexyloxy, n-naniloa, n-decile, n-undecyloxy, n-dodecyloxy, n-tridecanol, n-tetradecanol, n-hexadecanol, n-octadecyl or n-akosile group, such partially fluorinated or perfluorinated linear or branched alkyl group with the number of carbon atoms from one to twenty, as, for example, triptorelin, pentatration, heptafluoropropyl, performatrin, performanceline, performanceline, perforation, perperoglou, performerin the Yu, perfonally, perperoglou, performanceline, performanceline, performermarilyn, performanceduring, pertrochemical and perforacion group, unsubstituted or substituted linear or branched oxyalkylene group with the number of carbon atoms from one to twenty, such unsubstituted or substituted aryl group with the number of carbon atoms from six to twenty-four, as, for example, phenyl, biphenylyl or pentafluorophenyl group, such unsubstituted or substituted alcylaryl group with the number of carbon atoms in the alkyl residue of from one to twenty, as, for example, benzyl, methylphenyl, ethylphenyl, dimethylphenyl group, such unsubstituted or substituted axially group number of carbon atoms and from one to twenty, as, for example, fenoxaprop and biphenyloxy, or such unsubstituted or substituted heteroaryl group with carbon atoms of from one to twenty, as, for example, 2-thienyl, 3-thienyl, 2-fornillo, 3-fornillo, 2-pyrrolidinyl, 3-pyrrolidinyl, pyrazolidine, thiazolidine, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy, hyalinella, oxazolidinyl, thiazolino group.

In the preferred case, X1means in the General formula (II) such unsubstituted or substituted vinylidene, anilide the new or heteroarenes structural unit, as, for example, 1,4-fenelonov, 2,5-thienylene, 1,4'-biphenylene, 2.5-tienlen-vanilinovoi, 2,5'-bitirilene, 2,5"-tertiarylevel, 2,5'"quater-thienylene group.

Other possible substituents from R1to R4or X1there can be numerous organic groups, for example alkyl groups, partially fluorinated or perfluorinated alkyl, cycloalkyl, aryl groups, halogen atoms, substituents, functional groups, ethers, thioethers, disulfides, sulfoxidov, sulfones, sulfonates, amine groups, aldehyde groups, ketopropane, deputies with the functional groups of esters of carboxylic acids, carboxylic acids, carbonates, carboxylates, cyano groups, alkylsilane and alkoxysilane groups, as well as with carboxylamide groups.

As examples relevant to the invention compounds are the following compounds.

Bis(methylendioxyphenyl), Ter(methylendioxyphenyl), quater(methylendioxy-dryer), quinque(methylendioxyphenyl), sexy(methylendioxyphenyl), sati(methylene-dioxythiophene), acti(methylendioxyphenyl), poly(methylendioxyphenyl), bis(1',1'-utilitisation), Ter(1',1'-utilitisation), quater(1',1'-ethylidene-oxititan), quinque(1',1'-utilitisation), sexy(1',1'-utilizandose the open), septi(1',1'-utilitisation), acti(1',1'-utilitisation), poly(1',1'-utilitisation), bis(1',1'-propylitization), Ter(1',1'-propylitization), quater(1',1'-propylitization), quinque(1',1'-propylitization), sexy(1',1'-propylitization), septi(1',1'-propylitization), acti(1',1'-propylitization), poly(1',1'-propylitization), bis(2',2'-propylitization), Ter(2',2'-propylitization), quater(2',2'-propylitization), sexy(2',2'-propylitization), poly-(2',2'-propylitization), bis(1',1'-butylidenedioxy), Ter(1',1'-butylidenedioxy), quater(1',1'-butylidenedioxy), quinque(1',1'-butylidenedioxy), sexy(1',1'-butylidenedioxy), poly(1',1'-butylidenedioxy), bis(2',2'-butylidenedioxy), quater(2',2'-butylidenedioxy), quinque(2',2'-butylidenedioxy), sexy(2',2'-butylidenedioxy), poly(2',2'-butylidenedioxy), bis(1',1'-intelligentization), sexy(1',1'-intelligentization), poly(1',1'-intelligentization), bis(2',2'-intelligentization), quater(2',2'-intelligentization), sexy(2',2'-intelligentization), poly(2',2'-intelligentization), bis(3',3'-intelligentization), quater(3',3'-intelligentization), sexy(3',3 is-intelligentization), poly(3',3'-intelligentization), bis(1',1'-getselectedproxytype), quater(1',1'-getselectedproxytype), sexy(1',1'-getselectedproxytype), poly(1',1'-getselectedproxytype), bis(2',2'-getselectedproxytype), quater(2',2'-getselectedproxytype), sexy(2',2'-exileinoblivion), poly(2',2'-getselectedproxytype), bis(3',3'-getselectedproxytype), quater(3',3'-getselectedproxytype), sexy(3',3'-getselectedproxytype), poly(3',3'-getselectedproxytype), bis(1',1'-cyclopentanecarboxylate), Ter(1',1'-cyclopentanecarboxylate), quater(1',1'-cyclopentanecarboxylate), quinque(1',1'-cyclopentanecarboxylate), sexy(1',1'-cyclopentanecarboxylate), poly(1',1'-cyclopentanecarboxylate), bis(1',1'-cyclohexanecarboxylate), quater(1',1'-cyclohexanecarboxylate), sexy(1',1'-cyclohexanecarboxylate), poly(1',1'-cyclohexanecarboxylate), bis(1',1'-cyclobutanedicarboxylate), bis(1',1'-cyclopropanecarboxylate), bis(1',1'-benzylideneacetone), poly(1',1'-benzylideneacetone), bis(2'-phenyl-1',1'-utilitisation), sexy(2'-phenyl-1',1'-utilitisation), poly(2'-phenyl-1',1'-utilitisation). This list is intended to illustrate the invention, examples, and cannot be considered as final.

In the enter the joints with 1',1'-utilizedabsorbed groups we are talking about connections with one structural unit or more structural units of the following structure

.

In the preferred case, the object of the present invention are those corresponding to the invention of compounds that include at least 10 mol.% recurring structural units of the General formula (I).

In addition, in the preferred case, the object of the present invention are those corresponding to the invention compounds in which R1or R2means a hydrogen atom.

As examples relevant to the invention compounds are the following compounds.

2-Ethyl-bis(methylendioxyphenyl), 2-ethyl-Ter(methylendioxyphenyl), 2-ethyl-quater(methylendioxyphenyl), 2-ethyl-quinque(methylendioxyphenyl), 2-ethyl-sexy(methylendioxyphenyl), 2-ethyl-septi(methylendioxyphenyl), 2-ethyl-OCTI(methylendioxyphenyl), 2-propyl-bis(methylendioxyphenyl), 2-propyl-Ter(methylendioxyphenyl), 2-propyl-quater(methylendioxyphenyl), 2-propyl-quinque(methylendioxyphenyl), 2-propyl-sexy(methylendioxyphenyl), 2-propyl-septi(methylendioxyphenyl), 2-propyl-OCTI(methylendioxyphenyl), 2-butyl-bis(methylendioxyphenyl), 2-butyl-Ter(methylendioxyphenyl), 2-butyl-quater(methylendioxyphenyl), 2-butyl-quinque(methylendioxyphenyl), 2-butyl-sexy(methylendioxyphenyl), 2-butyl-septi(methylendioxyphenyl), 2-butyl-OCTI(methylendioxyphenyl), 2-pentyl-bis(methylendioxyphenyl),2-pentyl-Ter(methylendioxyphenyl), 2 pencil quater(methylendioxyphenyl), 2-pentyl-quinque(methylendioxyphenyl), 2-pentyl-sexy(methylendioxyphenyl), 2-pentyl-septi(methylendioxyphenyl), 2-pentyl-OCTI(methylendioxyphenyl), 2-hexyl-bis(methylendioxyphenyl), 2-hexyl-Ter(methylendioxyphenyl), 2-hexyl-quater(methylendioxyphenyl), 2-hexyl-quinque(methylendioxyphenyl), 2-hexyl-sexy(methylendioxyphenyl), 2-hexyl-septi(methylendioxyphenyl), 2-hexyl-OCTI(methylendioxyphenyl), 2-phenyl-bis(methylendioxyphenyl), 2-phenyl-Ter(methylendioxyphenyl), 2-phenyl-quater(methylendioxyphenyl), 2-phenyl-quinque(methylendioxyphenyl), 2-phenyl-sexy(methylendioxyphenyl), 2-phenyl-septi(methylendioxyphenyl), 2-phenyl-OCTI(methylendioxyphenyl), 2,5'-diethyl-bis(methylendioxyphenyl), 2,5'-dipropyl-bis(methylendioxyphenyl), 2,5'-dibutil-bis(methylendioxyphenyl), 2,5'-dipentyl-bis(methylendioxyphenyl), 2,5'-dihexyl-bis(methylendioxyphenyl), 2,5'-dioctyl-bis(methylendioxyphenyl), 2,5'-diphenyl-bis(methylendioxyphenyl), 2,5-dimethyl-Ter(methylendioxyphenyl), 2,5-diethyl-Ter(methylendioxyphenyl), 2,5-dipropyl-Ter(methylendioxyphenyl), 2,5"-dibutil-Ter(methylendioxyphenyl), 2,5-dihexyl-Ter(methylendioxyphenyl), 2,5-dioctyl-Ter(methylendioxyphenyl), 2,5-Didecyl-Ter(methylendioxyphenyl), 2,5-didodecyl-Ter(methylendioxyphenyl), 2,5"'-dimethyl-quater(methylendioxyphenyl), 2,5'what the-diethyl-quater(methylendioxyphenyl), 2,5"'-dihexyl quater(methylendioxyphenyl), 2,5'-Didecyl quater(methylendioxyphenyl), 2,5""-diethyl-quinque(methylendioxyphenyl), 2,5""-dihexyl-quinque(methylendioxyphenyl), 2,5""-Didecyl-quinque(methylendioxyphenyl), 2,5'""-dimethyl-sexy(methylendioxyphenyl), 2,5""'-diethyl-sexy(methylendioxyphenyl), 2,5'""-dihexyl-sexy(methylendioxyphenyl), 2,5""'-diphenyl-sexy(methylendioxyphenyl), 2,5'-thienyl-bis(methylendioxyphenyl), 2,5'-bis(2-utilties-5-yl)-bis(methylendioxyphenyl), 2,5'-bis(2-hexylthio-5-yl)-bis(methylendioxyphenyl), 2-kvartiry-methylendioxyphenyl, 2-tertiary-5-thienyl-methylendioxyphenyl, 2,5-di(bithienyl)-methylendioxyphenyl, 2-tertiary-methylendioxyphenyl, 2-bithienyl-5-thienyl-methylendioxyphenyl, 2-bithienyl-methylendioxyphenyl, 2-thienyl-methylendioxyphenyl, 2-quater-phenyl-methylendioxyphenyl, 2-terphenyl-5-phenyl-methylendioxyphenyl, 2,5-bis(biphenyl)-methylendioxyphenyl, 2-terphenyl-methylendioxyphenyl, 2-biphenylyl-5-phenyl-methylendioxyphenyl, 2-biphenylyl-methylendioxyphenyl, 2-phenyl-methylene-dioxythiophene. This list is intended to illustrate the invention examples, and it can not be considered as final.

In addition, in the preferred case, the object of the present invention are those corresponding to the invention compounds in which R3and R4about the means a hydrogen atom.

In addition, in the preferred case, the object of the present invention are those corresponding to the invention compounds in which m is 0.

These correspond to the invention compounds represented by the General formula (III)

where R1, R2, R3, R4and n have the above for General formula (I) and (II) value. The preferred range of values and combinations of these limit values apply to the occasion.

In preferred embodiments, they are such compounds of General formula (III-a)

where R1or R2mean hydrogen atoms, and R3, R4and n have the above for General formula (I) and (II) value. The preferred range of values and combinations of these limit values apply to this case. In the most preferred embodiment, they are compounds in which R1means a hydrogen atom and R2means methyl group.

As examples relevant to the invention compounds of General formula (III-a) are the following substances:

bis(1',1'-utilitisation), Ter(1',1'-utilitisation), quater(1',1'-utilitisation), quinque(1',1'-utilitisation), sexy(1',1'-utilitisation), septi(1',1'-ethylidene maxitive), OCTI(1',1'-utilitisation), 2-ethyl-bis(1',1'-utilitisation), 2-ethyl-Ter(1',1'-utilitisation), 2-ethyl-quater(1',1'-utilitisation), 2-ethyl-quinque(1',1'-utilitisation), 2-ethyl-sexy(1',1'-utilitisation), 2-ethyl-septi(1',1'-utilitisation)2-ethyl-OCTI(1',1'-utilitisation), 2-propyl-bis(1',1'-utilitisation), 2-propyl-Ter(1',1'-utilitisation), 2-propyl-quater(1',1'-utilitisation), 2-propyl-quinque(1',1'-utilitisation), 2-propyl-sexy(1',1'-utilitisation), 2-propyl-septi(1',1'-utilitisation), 2-propyl-OCTI(1',1'-utilitisation), 2-butyl-bis(1',1'-utilitisation), 2-butyl-Ter(1',1'-utilitisation), 2-butyl-quater(1',1'-utilitisation), 2-butyl-quinque(1',1'-utilitisation), 2-butyl-sexy(1',1'-utilitisation), 2-butyl-septi(1',1'-utilitisation), 2-butyl-OCTI(1',1'-utilitisation), 2-pentyl-bis(1',1'-utilitisation), 2-pentyl-Ter(1',1'-utilitisation), 2-pentyl quater(1',1'-utilitisation), 2-pentyl-quinque(1',1'-utilitisation), 2-pentyl-sexy(1',1'-utilitisation), 2 pentyl-septi(1',1'-utilitisation), 2-pentyl-OCTI(1',1'-utilitisation), 2-hexyl-bis(1',1'-utilitisation), 2-hexyl-Ter(1',1'-utilitisation), 2-hexyl-quater(1',1 is the-utilitisation), 2-hexyl-quinque(1',1'-utilitisation), 2-hexyl-sexy(1',1'-utilitisation), 2-hexyl-septi(1',1'-utilitisation), 2-hexyl-OCTI(1',1'-utilitisation), 2-phenyl-bis(1',1'-utilitisation), 2-phenyl-Ter(1',1'-utilitisation), 2-phenyl-quater(1',1'utilitisation), 2-phenyl-quinque(1',1'-utilitisation), 2-phenyl-sexy(1',1'-utilitisation), 2-phenyl-septi(1',1'-utilitisation), 2-phenyl-OCTI(1',1'-utilitisation), 2,5'-diethyl-bis(1',1'-utilitisation), 2,5'-dipropyl-bis(1',1'-utilitisation), 2,5'-dibutil-bis(1',1'-utilitisation), 2,5'-dipentyl-bis(1',1'-utilitisation), 2,5'-dihexyl-bis(1',1'-utilitisation), 2,5'-dioctyl-bis(1',1'-utilitisation), 2,5'-diphenyl-bis(1',1'-utilitisation), 2,5-dimethyl-Ter(1',1'-utilitisation), 2,5-diethyl-Ter(1',1'-utilitisation), 2,5-dipropyl-Ter(1',1'-utilitisation), 2,5"-dibutil-Ter(1',1'-utilitisation), 2,5-dihexyl-Ter(1',1'-utilitisation), 2,5-dioctyl-Ter(1',1'-utilitisation), 2,5-Didecyl-Ter(1',1'-utilitisation), 2,5-didodecyl-Ter(1',1'utilitisation), 2,5"'-dimethyl-quater(1',1'-utilitisation), 2,5"'-diethyl-quater(1',1'-utilitisation), 2,5'-dihexyl quater-(1',1'-utilitisation), 2,5'-Didecyl-Quat is p(1',1'-utilitisation), 2,5""-diethyl-quinque(1',1'-utilitisation), 2,5""-dihexyl-quinque-(1',1'-utilitisation), 2,5""-Didecyl-quinque(1',1'-utilitisation), 2,5'""-dimethyl-sexy(1',1'-utilitisation), 2,5'""-diethyl-sexy(1',1'-utilitisation), 2,5"'"-dihexyl-sexy(1',1'-utilitisation), 2,5'""-diphenyl-sexy(1',1'-utilitisation), 2-pentafluoroethyl-bis(1',1'-utilitisation), 2-pentafluoroethyl-Ter(1',1'-utilitisation), 2-pentafluoroethyl quater(1',1'-utili-indicitive), 2-pentafluoroethyl-quinque(1',1'-utilitisation), 2-pentafluoroethyl-sexy(1',1'-utilitisation)2-pentafluoroethyl-septi(1',1'-utilitisation), 2-pentafluoroethyl-OCTI(1',1'-utilitisation), 2-heptafluoropropyl-bis(1',1'-utilitisation), 2-heptafluoropropyl-Ter(1',1'-utilitisation), 2-heptafluoropropyl quater(1',1'-utilitisation), 2-heptafluoropropyl-quinque(1',1'-utilitisation), 2-heptafluoropropyl-sexy(1',1'-utilitisation), 2-heptafluoropropyl-septi(1',1'-utilitisation), 2-heptafluoropropyl-OCTI(1',1'-utilitisation), 2-performatic-bis(1',1'-utilitisation), 2-performatic-Ter(1',1'-utilitisation), 2-performatic quater(1',1'-utilitisation), 2-performatic-quinque(1',1'-utilitisation), 2-performatic-sexy(1',1'-utilizing oxititan), 2-performatic-septi(1',1'-utilitisation), 2-performatic-OCTI(1',1'-utilitisation), 2-performancel-bis-(1',1'-utilitisation), 2-performancel-Ter(1',1'-utilitisation), 2-performancel quater(1',1'-utilitisation), 2-performancel-quinque(1',1'-utilitisation), 2-performancel-sexy(1',1'-utilitisation), 2-performancel-septi(1',1'-utilitisation), 2-performancel-OCTI(1',1'-utilitisation), 2-perferences-bis(1',1'-utilitisation), 2-perferences-Ter(1',1'-utilitisation), 2-perferences quater(1',1'-utilitisation), 2-perferences-quinque(1',1'-utilitisation), 2-perferences-sexy-(1',1'-utilitisation), 2-perferences-septi(1',1'-utilitisation), 2-perferences-OCTI(1',1'-utilitisation), 2,5'-bis(heptafluoropropyl)-bis-(1',1'-utilitisation), 2,5'-vperformer-bis(1',1'-utilitisation), 2,5'-dipartimenti-bis(1',1'-utilitisation), 2,5'-diphthongised bis-(1',1'-utilitisation), 2,5'-departanental-bis-(1',1'-utilitisation), 2,5'-bis(pentafluorophenyl)bis-(1',1'-utilitisation), 2,5"-bis(trifluoromethyl)-Ter(1',1'-utilitisation), 2,5"-bis(pentafluoroethyl)-Ter(1',1'-utilitisation), 2,5"-bis(heptafluoropropyl)-Ter(1',1'utilitisation), 2,5"-bis(what afterbody)-Ter(1',1'-utilitisation), 2,5"-bis-(perferences)-Ter(1',1'-utilitisation), 2,5"-bis(perforater)-Ter(1',1'-utilitisation), 2,5"-bis-(peritonitis)-Ter(1',1'-utilitisation), 2,5"-bis(perforater)-Ter(1',1'-utilitisation), 2,5'"-bis(trifluoromethyl)-quater(1',1'-utilitisation), 2,5'"bis(pentafluoroethyl)-quater(1',1'-utilitisation), 2,5'"-bis(perferences)quater-(1',1'-utilitisation), 2,5'"-bis(peritonitis)-quater(1',1'-utilitisation), 2,5""-bis(pentafluoroethyl)-quinque(1',1'-utilitisation), 2,5""-bis(perferences)-quinque(1',1'-utilitisation), 2,5""-bis(peritonitis)-quinque(1',1'-utilitisation), 2,5""'-bis(trifluoromethyl)-sexy(1',1'-utilitisation), 2,5"'"-bis(pentafluoroethyl)-sexy(1',1'-utilitisation), 2,5'""-bis(perferences)-sexy(1',1'-utilitisation), 2,5'""-bis(pentafluorophenyl)-sexy(1',1'-utilitisation). This list is intended to illustrate the invention by the examples, it can not be considered as final.

In other preferred embodiments of such relevant to the invention the compounds are represented by the compounds of General formula (III-b)

where R1and R2means a hydrogen atom, a R3, R4and n have the above for General formula (I) and (II) the value the of. The preferred range of values and combinations of these limit values apply to the occasion.

As examples relevant to the invention compounds of General formula (III-b) in addition to those already included in the previous enumeration contains the following substances:

2-pentafluoroethyl-bis(methylendioxyphenyl), 2-pentafluoroethyl-Ter(methylendioxyphenyl), 2-pentafluoroethyl quater(methylendioxyphenyl), 2-pentafluoroethyl-quinque(methylendioxyphenyl), 2-pentafluoroethyl-sexy(methylendioxyphenyl), 2-pentafluoroethyl-septi(methylendioxyphenyl), 2-pentafluoroethyl-OCTI(methylendioxyphenyl), 2-heptafluoropropyl-bis(methylendioxyphenyl), 2-heptafluoropropyl-Ter(methylendioxyphenyl), 2-heptafluoropropyl quater(methylendioxyphenyl), 2-heptafluoropropyl-quinque(methylendioxyphenyl), 2-heptafluoropropyl-sexy(methylendioxyphenyl), 2-heptafluoropropyl-septi(methylendioxyphenyl), 2-heptafluoropropyl-OCTI(methylendioxyphenyl), 2-performatic-bis(methylendioxyphenyl), 2-performatic-Ter(methylendioxyphenyl), 2-performatic quater(methylendioxyphenyl), 2-performatic-quinque(methylendioxyphenyl), 2-performatic-sexy(methylendioxyphenyl), 2-PERFLUORO-butyl-septi(methylendioxyphenyl), 2-performatic-OCTI(methylendioxyphenyl), 2-performancel-bis(methylendioxyphenyl), 2-performancel-Ter(methylendioxyphenyl), 2-perft bentyl quater(methylendioxyphenyl), 2-performancel-quinque(methylendioxyphenyl), 2-performancel-sexy(methylendioxyphenyl), 2-performancel-septi(methylendioxyphenyl), 2-performancel-OCTI(methylendioxyphenyl), 2-perferences-bis(methylendioxyphenyl), 2-perferences-Ter(methylendioxyphenyl), 2-perferences quater(methylendioxyphenyl), 2-perferences-quinque(methylendioxyphenyl), 2-perferences-sexy(methylendioxyphenyl), 2-perferences-septi(methylendioxyphenyl), 2-perferences-OCTI(methylendioxyphenyl), 2-phenyl-bis(methylendioxyphenyl), 2-phenyl-Ter(methylendioxyphenyl), 2-phenyl-quater(methylendioxyphenyl), 2-phenyl-quinque(methylendioxyphenyl), 2-phenyl-sexy(methylendioxyphenyl), 2-phenyl-septi(methylendioxyphenyl), 2-phenyl-OCTI(methylendioxyphenyl), 2,5'-bis(pentafluoroethyl)-bis(methylendioxyphenyl), 2,5'-bis(heptafluoropropyl)-bis(methylendioxyphenyl), 2,5'-bis(performatic)-bis(methylendioxyphenyl), 2,5'-bis(performancel)-bis(methylendioxyphenyl), 2,5'-bis(perferences)-bis(methylendioxyphenyl), 2,5'-dioctyl-bis-(methylendioxyphenyl), 2,5'-bis(pentafluorophenyl)bis(methylendioxyphenyl), 2,5"-bis(trifluoromethyl)-Ter(methylendioxyphenyl), 2,5"-bis(pentafluoroethyl)-Ter(methylendioxyphenyl), 2,5"-bis(heptafluoropropyl)-Ter(methylendioxyphenyl), 2,5"-bis(performatic)-Ter(methylendioxyphenyl), 2,5"-bis(perferences)-Ter(methylendioxy is), 2,5"-bis(perforater)-Ter(methylendioxyphenyl), 2,5"-bis(peritonitis)-Ter(methylendioxyphenyl), 2,5"-bis(perforater)-Ter(methylendioxyphenyl), 2,5'"-bis(trifluoromethyl)-quater(methylendioxyphenyl), 2,5'"-bis(pentafluoroethyl)-quater(methylendioxyphenyl), 2,5"'-bis(perferences)-quater(methylendioxyphenyl), 2,5'"-bis(peritonitis)-quater(methylendioxyphenyl), 2,5""bis(pentafluoroethyl)-quinque(methylendioxyphenyl), 2,5""-bis(perferences)-quinque(methylendioxyphenyl), 2,5""-bis(peritonitis)-quinque(methylendioxyphenyl), 2,5'""-bis(trifluoromethyl)-sexy(methylendioxyphenyl), 2,5"'"-bis(pentafluoroethyl)-sexy(methylendioxyphenyl), 2,5'""-bis(perferences)-sexy(methylendioxyphenyl), 2,5'""-bis(pentafluorophenyl)-sexy(methylendioxyphenyl). This list is intended to illustrate the invention, examples, and he cannot be considered as final.

In other preferred embodiments of the relevant invention compounds represented by compounds of General formula (III-C)

where R1, R2, R3and R4means a hydrogen atom, and n has the above for General formula (I) value. The preferred range of values pertain to the occasion.

As examples relevant to the invention compounds of General Faure the uly (III-C) are the following substances:

bis(methylendioxyphenyl), Ter(methylendioxyphenyl), quater(methylendioxyphenyl), quinque(methylendioxyphenyl), sexy(methylendioxyphenyl), sati(methylendioxyphenyl), acti(methylendioxyphenyl), Novi(methylendioxyphenyl), deci(methylendioxyphenyl), undeci(methylendioxyphenyl), dodeca(methylendioxyphenyl) and poly(methylendioxyphenyl). This list is intended to illustrate the invention examples, and it can not be considered as final.

In principle, relevant to the invention compounds can be obtained by using various well-known specialist methods based on the use of at least one ORGANOMETALLIC reactions.

On this basis the object of the invention is a method for retrieving relevant to the invention compounds, which corresponds to the invention a connection is received with the participation of at least one ORGANOMETALLIC reactions.

In the preferred case of this method, which corresponds to the invention the connection get by the reaction of a combination of Comedy, by the reaction of a combination of Suzuki or by the reaction of a combination of Still.

In the preferred case of the invention corresponding to the invention of compounds obtained using one of the variants of combination reaction Suzuki, also often called condensation Suzuki Suzuki Condensation or accordingly, the Suzuki reaction mix, i.e. the interaction of aryl halides and derivatives arylboronic acid with a compound of palladium as a catalyst in the presence of a base, as described, for example, in the work of Suzuki and others, Chem. Rev. 1995, 95, 2457-2483. In a preferred embodiment of the invention corresponding to the invention the method is carried out according to one corresponding to the invention, variants of this reaction combinations Suzuki, on which organolanthanide and, accordingly, the esters organibarely acids in each case, react in the presence of at least one base and/or at least one catalyst containing a metal of the VIII side group of the Periodic system of elements, hereinafter abbreviated VIII metal side of the band.

In the preferred case of implementing the invention method (Suzuki reaction mix) the work is carried out at a temperature of +20°C to +200°C, in the preferred case, from +40°C to +150°C, in the most preferred case from +80°C up to +130°C, in an organic solvent or solvent mixture.

As catalysts containing a metal of the VIII side of the group, in principle, can be considered all suitable compounds which contain a metal of the VIII side groups, preferred is palladium, Nickel or platinum, in the preferred case, it is palladium. The catalyst or catalysts used in the preferred case in the amount of from 0.05 wt.% up to 10 wt.%, in the most preferred case, from 0.5 wt.% up to 5 wt.%, based on the total weight reacts combinations of connections.

The most suitable catalysts are complex compounds of metals of the VIII side groups, in particular complexes of palladium(0), which is stable in air, palladium complexes, which can be easily recovered ORGANOMETALLIC reagents (e.g., alkyllithium compounds or magnetogenesis compounds) or phosphines to complexes of palladium(0), or complexes of divalent palladium, as appropriate, with the addition of triphenylphosphine or other phosphines. For example, can be used dichloride, bis(triphenyl-phosphine)palladium dibromide bis(triphenylphosphine)palladium or palladium diacetate or mixtures of these compounds with the addition of triphenylphosphine. Preference is given to using tetrakis(triphenylphosphine)of palladium with the addition of phosphines or without them, in the preferred embodiment, without the addition of phosphines, which is available at a low price. As phosphines in the preferred use of triphenylphosphine, diphenylmethylphosphine, diphenylmethylphosphine, diethylphenylphosphine or triethylphosphine, special preference is to reperfusion.

However, as catalysts can be used and palladium compounds without the addition of phosphines, such as palladium diacetate.

As bases there may be used, for example, hydroxides such as, for example, sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, calcium hydroxide, alkoxides such as, for example, sodium ethylate, potassium ethylate, lithium ethylate, sodium methylate, potassium methylate, lithium methylate, such alkali metal salts and carboxylic acids, as, for example, carbonates of sodium, potassium or lithium, bicarbonates, acetates, citrates, acetylacetonates, glycine chelates, or such other carbonates, such as cesium carbonate or carbonate thallium such phosphates, such as sodium phosphate, potassium phosphate, or lithium phosphate, or mixtures of these compounds. In the preferred case of using sodium carbonate. The base can be used as solutions in water or in the form of a suspension in such organic solvents as toluene, dioxane or dimethylformamide. Preference is given to solutions in water, because these products are poorly soluble in water and therefore can be easily separated from the reaction mixture.

You can also use other salts, such as lithium chloride or lithium bromide, as an auxiliary means.

In principle, as an organic solvent may be used any organic solvent or mixture of solvents, which do not react with esters Baranovich acids. As a rule, are compounds in which there are no atoms of halogen or reactive esters Baranovich acid hydrogen atoms. Suitable solvents are, for example, alkanes such as pentane, hexane and heptane, such aromatic compounds as benzene, toluene and xylenes, such compounds comprising a functional group of ethers like dioxane, dimethoxyethane and tetrahydrofuran, and also polar solvents, such as dimethylformamide or dimethylsulfoxide. In the preferred case of the invention the method as solvents used aromatic compounds. Particular preference is given to toluene. However, it is possible to use as solvent a mixture of two or more such solvents.

Used in this way organolanthanide can be obtained in various ways, or they may be purchased commercially. Obtaining esters Baranovich acids can be carried out, for example, by reacting aryl halides and bis(organyl)of DIBORANE in the catalyzed metal combination (application of international patent No. 01/29051 A1, Tetrahedron Lett. 2002, s), a combination of oligothiophenes, for example, pinacolborane (J. Org. Chem. 1997, T, s; J. were obtained. Chem. 2001, T, s; Chem. Sarnico. 2002, s) or by interaction of ORGANOMETALLIC compounds, for example magyarkanizsa compounds (e.g., Grignard reagents or organolithium compounds, esters Baranovich acids. These methods specialist known.

In another preferred case of the invention corresponding to the invention compounds are obtained by reaction of a combination of Comedy. The reaction mix of Comedy, i.e. the interaction of aryl halides and aryl Grignard reagents in the presence of palladium or Nickel catalyst, as described, for example, Kumada, etc., J. Am. Chem. Soc. 1972, 94, 4373-4376. In a preferred embodiment for implementing the invention method uses the appropriate variant of this invention the reaction of a combination of Comedy navigated the interaction of aryl halides or, respectively, heteroarylboronic and Grignard reagents on the basis of aryl - or, respectively, heteroarylboronic in the presence of a catalyst containing a metal of the VIII side group of the Periodic system of elements, hereinafter abbreviated VIII metal side of the band. In a preferred embodiment for implementing the invention method (reaction of a combination of Comedy) work carried out at a temperature from 0°C to +200°C, in the preferred case from +20°C to +150°C, most preferred with whom you learn from +40°C up to +130°C, in an organic solvent or solvent mixture.

As catalysts containing a metal of the VIII side of the group, in principle, can be considered all suitable compounds which contain a metal of the VIII side groups, preferred is palladium or Nickel, in the most preferred case is palladium. The catalyst or catalysts used in the preferred case in the amount of from 0.05 wt.% up to 10 wt.%, in the most preferred case, from 0.5 wt.% up to 5 wt.%, based on the total weight reacts combinations of connections.

The most suitable catalysts are complex compounds of metals of the VIII side groups, in particular complexes of palladium(0), which is stable in air, palladium complexes, which can be easily recovered ORGANOMETALLIC reagents (e.g., alkyllithium compounds or magnetogenesis compounds) or phosphines to complexes of palladium(0), or complexes of divalent palladium, as appropriate, with the addition of triphenylphosphine or other phosphines. For example, can be used dichloride, bis(triphenylphosphine)palladium dibromide bis(triphenylphosphine)palladium or palladium diacetate or mixtures of these compounds with the addition of diphenylphosphinoethyl or diphenylphosphinomethyl or 1,1'-bis(given phosphino)ferrocene. Preference is given to using as catalysts complexes of palladium dichloride with diphenylphosphinoethyl, diphenylphosphinoethyl and 1,1'-bis(diphenylphosphino)ferrocene.

As organic solvents are suitable in principle all solvents or mixture of solvents that do not react with Grignard reagents. As a rule, are compounds that do not contain halogen atoms or reactive Grignard reagents hydrogen atoms. Suitable solvents are, for example, such aromatic compounds as benzene, toluene and xylenes, containing such a functional group of ester compounds as dioxane, dimethoxyethane, diethyl ether, disutility ether and tetrahydrofuran. In the relevant invention methods are preferred ether solvents. The most preferred tetrahydrofuran. Can also be used as solvent a mixture of two or more such solvents.

In another preferred case of the invention corresponding to the invention compounds are obtained by reaction of a combination of Stille. The combination of the reaction of Style, i.e. the interaction of arylalkenes and aryl or alkenylphenol ORGANOTIN compounds in the presence of palladium catalyst are described, for example, Stille and others, Angew. Chem. 1986, 98 504. In a preferred embodiment of the invention corresponding to the invention the method is carried out according to one corresponding to the invention, variants of this reaction, the combination of Style, in which the aryl - or, respectively, heteroarylboronic and aryl and alkeneamine ORGANOTIN compounds react in the presence of a catalyst containing a metal of the VIII side group of the Periodic system of elements, hereinafter abbreviated VIII metal side of the band. In the preferred case of implementing the invention method (reaction combination Style) work carried out at a temperature from 0°C to +200°C, in the preferred case from +20°C to +150°C, in the most preferred case, from +40°C up to +130°C, in an organic solvent or solvent mixture.

As catalysts containing a metal of the VIII side of the group, in principle, can be considered all suitable compounds which contain a metal of the VIII side groups, the most preferred is palladium. The catalyst or catalysts used in the preferred case in the amount of from 0.05 wt.% up to 10 wt.%, in the most preferred case, from 0.5 wt.% up to 5 wt.%, based on the total weight reacts combinations of connections.

The most suitable catalysts are complex compounds of metals of the VIII p the software group, in particular complexes of palladium(0), which is stable in air, palladium complexes, which can be easily recovered ORGANOMETALLIC reagents (e.g., alkyllithium compounds or magnetogenesis compounds) or phosphines to complexes of palladium(0), or complexes of divalent palladium, as appropriate, with the addition of triphenylphosphine or other phosphines. For example, can be used dichloride, bis(triphenylphosphine)palladium dibromide bis(triphenylphosphine)palladium or palladium diacetate or mixtures of these compounds with the addition of triphenylphosphine. Preference is given to using available low-cost tetrakis(triphenylphosphine)of palladium with the addition of phosphines or without them, in the preferred embodiment, without the addition of phosphines. As phosphines in the preferred use of triphenylphosphine, diphenylmethylphosphine, diphenylmethylphosphine, diethylphenylphosphine or triethylphosphine, particular preference is given to triphenylphosphine.

However, as catalysts can be used and palladium compounds without the addition of phosphines, such as palladium diacetate.

In principle, as organic solvents can be used all organic solvents or mixtures of solvents which do not react with ORGANOTIN compounds As a rule, this connection, in which no halogen atoms or hydrogen atoms reactive with ORGANOTIN compounds. Suitable solvents are, for example, such aromatic compounds as benzene, toluene and xylenes, such compounds comprising a functional group of ethers like dioxane, dimethoxyethane, diethyl ether, disutility ether and tetrahydrofuran, or polar solvents, such as dimethylformamide, N-organic or acetonitrile. Can also be used as solvent a mixture of two or more such solvents.

The division formed in each case the reaction mixture is carried out using known methods, for example by dilution, sedimentation, filtration, extraction, washing, recrystallization from suitable solvents, chromatography was carried out and/or sublimation. For example, the selection of the product can proceed as follows: after completion of the reaction the reaction mass is poured into a mixture of acidified water (with ice), for example, it is derived from odnomestnoi hydrochloric acid, and toluene, the organic phase is separated, washed with water, obtained in the form of a solid product filtered off, washed with toluene and then dried in vacuum. Corresponding to the invention connected with good quality and a high degree number is the notes can be obtained without the use of other final purification processes. However, these products can be further purified by known methods, for example by recrystallization, chromatographytandem or sublimation.

Corresponding to the invention compounds are electrically neutral, they are semiconductors and low sensitivity to oxidation. In addition, they can be easily applied from a solution. As a result, they are suitable for use as organic semiconductor in (opto)electronic functional elements.

This is quite unexpected, because the basic Monomeric compound 3,4-methylendioxyphenyl or, respectively, thieno[3,4-d]-1,3-dioxol known specialist for a number of publications and it can be assumed that the connection with methylendioxyphenyl structural units similar in properties to other compounds containing 3,4-alkylenediamine structural units. So it would be expected that compounds containing methylenedioxyphenol structural units, have a stable electrically charged or oxidized state and a neutral state, most likely unstable. For example, Ahonen, etc., Synthetic metals (1997). 84 (1-3), 215-216, describe polymers of methylendioxyphenyl only in the oxidized state, that is in cationic form, and accordingly they can be used is designed only as organic conductors current but not as semiconductors (see also the application for the European patent No. 339340). Oxidized, i.e. neutral, compounds with 3,4-methylendioxyphenyl structural units to date in the literature are not described.

Consequently, another object of the present invention is also the application of the relevant invention compounds as organic semiconductors in electronic functional elements, in such active and light-emitting electronic functional elements, such as field-effect transistors, organic light-emitting diodes, photovoltaic cells, lasers or sensors.

In addition, corresponding to the invention the compound is applied in layers on appropriate substrates, such as silicon substrate, and an electrical or electronic structures on a polymer film or glass plates. In principle, the application can be used any known specialist methods of application. So, for example, compounds of General formula (I) is applied from the gas phase or from a solution, then vaporizing the solvent. Application of the solution can be conducted by known methods, for example by means of a spray, dipping, stamping and screen printing, drawing, using centrifugal force and by the way inkjet printing the tees. Corresponding to the invention compounds can also be deposited from the gas phase, for example, by condensation of the vapor. This method can be obtained layers with minimal defects and with the high mobility of the charges.

In addition, an object of the present invention in accordance with the foregoing is an electronic functional element containing at least one relevant to the invention the connection.

The following examples are intended to illustrate and detail of the invention, but they do not limit the scope of the claims.

Examples

Example 1. Synthesis of bis(methylendioxyphenyl) (III-C-1) (bis-MDT)

In nitrogen atmosphere in 100 ml of absolute tetrahydrofuran is dissolved 3,96 g of 3,4-methylenedioxyphenol and cooled to 0°C. To the cooled to 0°C solution are added dropwise 20 ml of a solution of n-utility in n-hexane with a concentration of 1.6 mol/L. the Mixture is stirred for 30 minutes at 0°C. Then one technique is added to 4.41 g of the dichloride of copper and to complete the reaction is stirred for 12 hours at 23°C. then poured into ice water and sucked off, gain of 1.9 g (48% of theory) of bis(3,4-methylendioxyphenyl) (III-s-1).

TPL 225-231°C.

Elemental analysis: found: From 46.7%, N Of 2.25%, S 24,6%

calculated: 47,0%, N 2,37%, S 25,6% (for C10H6O4S2).

Range1H I Is P (deuterochloroform, ppm δ relative to tetramethylsilane was): 6,00 (2N), 6,28 (4H).

Example 2. Synthesis of 2-hexyl-bis(methylendioxyphenyl) (III-b-1)

To 20 ml of anhydrous tetrahydrofuran at -20°C was added to 3.52 ml n-utility in hexane with a concentration of 2.5 mol/L. the Mixture is stirred for 1 hour and then add 2,03 g bis-MDT (III-1)obtained in example 1, in 50 ml of tetrahydrofuran. A mixture of one hour and stirred at -20°C and then at -20°C was added 1.65 g hexylboronic. Mixture is allowed to warm up and hydrolyzing it with water. The aqueous phase is extracted with methylene chloride three times 50 ml and completely distilled off the solvent from the combined organic phases. After chromatography was carried out on silica gel obtain 0.7 g of 2-hexyl-bis(methylendioxyphenyl) in the form of a solid light gray color.

Example 3. Synthesis of 2,5"'-dihexyl quater(methylendioxyphenyl) (III-b-2)

n=3

To 20 ml of tetrahydrofuran at -70°C. add 1 ml n-utility in n-hexane with a concentration of 1.6 mol/L. then added dropwise of) 0.157 ml Diisopropylamine and stirred the mixture for 1 hour. Then at -78°C was added dropwise 0.5 g of 2-hexyl-bis(methylendioxyphenyl)obtained according to example 2. Mixture is allowed to warm to -20°C. and 1 hour mix. Then again cooled to -78°C and added about 0.16 the anhydrous chloride of copper(II). A mixture of 1 hour and stirred at -70°C and then allow it to warm to 23°C. then hydrolyzing with water, the aqueous phase is extracted with methylene chloride three times 50 ml and completely distilled off the solvent from the combined organic phases. Obtain 0.24 g of 2,5"'-vexilar(methylendioxyphenyl) (III-b-2) as a yellow-brown powder.

1. Neutral organic semiconductor compound of General formula (I)

where R1and R2means a hydrogen atom,
the number of recurring structural units of the General formula (I) is n,
and n means an integer from 2 to 1000,
and this connection is also end groups R3and R4and
R3and R4independently from each other mean a hydrogen atom or a linear or branched alkyl group with the number of carbon atoms from one to twenty.

2. Semiconducting organic compound according to claim 1, wherein R3and R4means a hydrogen atom.

3. The use of compounds according to one of claims 1 or 2 as a semiconductor in electronic functional elements.

4. The use according to claim 3, characterized in that the electronic functional elements are selected from groups: field-effect transistors, such light-emitting functional elements, such as organic light-emitting diodes, photovoltaic cells, lasers and encore.

5. Electronic functional element, characterized in that it contains at least one compound according to one of claims 1 or 2.



 

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3 cl, 4 dwg

FIELD: electricity.

SUBSTANCE: in the proposed method in conductors made from various materials there made along the junction line are slots alternating with protrusions; at that, protrusions of one conductor are inserted in the slots of the other conductor, and deforming force is applied perpendicular to the surface restricted at least with the height of slots and protrusions of more flexible conductor, at specific pressure of the press of about 120 kg/mm2 as at cold welding. Slots and protrusions are of rectangular or triangular shape, which are made by milling or die forming with simultaneous cleaning of the surface from oxide film immediately before pressing. So, transient resistance in connected conductors is almost absent.

EFFECT: improving connection reliability and increasing current collection area of buses.

3 cl, 3 dwg

FIELD: electricity.

SUBSTANCE: electrically conducting composite material includes the following, wt %: titanium nitride TiN - 65-70 and iron Fe - 30-35. For obtaining the proposed electrically conducting composite material there used is charge containing the following, wt %: ferrotitanium 60-70 and pre-nitrided ferrotitanium 30-40. Electrically conducting composition includes the proposed electrically conducting composite material 30-70 wt % and organic silicon compound used as binding agent in quantity of 30-70 wt %.

EFFECT: enlarging operating temperature interval of electrically conducting composite material at its high temperature stability.

3 cl, 2 dwg, 2 ex

FIELD: physics.

SUBSTANCE: invention can be used in electronic engineering when making display devices, particularly cathodoluminescent displays. In the electroconductive paste which contains an organic binder and an inorganic component, the inorganic component is stabilised nanodispersed silver powder with particle size of 20-50 nm and fine-dispersed silver powder with particle size of 1-5 mcm with the following ratio of components, in wt %: organic binder 20-40, nanodispersed silver powder 10-20, fine-dispersed silver powder 60-85.

EFFECT: design of electroconductive paste for making conducting tracks using a high-resolution screen-printing technique.

2 tbl

FIELD: electricity.

SUBSTANCE: invention relates to the field of electrical engineering, in particular to self-regulated current-conducting sealing material arranged on the basis of polysulfide oligomers (Thiokol) and may find application in development of flexible electric heating elements, and also sealants. In proposed self-regulated compound, electric resistance of material increases as electric current flows through it, due to the fact that in warmer sections material of compound expands, thus reducing a number of current-conducting "tracks" made of carbon material. Current-conducting sealing compound comprises the following components, wt parts: Thiokol NVB-2 - 100, technical carbon P-803 - 30-40, manganese dioxide in the form of paste No.9 - 15-35, diphenyl guanidine - 1, as self-regulated current conducting material.

EFFECT: efficient "self-regulation" of specific electric resistance in the range of temperatures from -30°C to +40°C .

1 tbl, 1 dwg

FIELD: electricity.

SUBSTANCE: invention relates to the field of electric engineering, in particular to polymer electrolyte and electrochemical device using polymer electrolyte. Problem has been solved due to application of polymer electrolyte (5), which has ketone carbonyl group, where mass fraction of ketone carbonyl group makes from 15 to 50 % (wt) relative to mass of polymer material, and mass fraction of electrolyte salt relative to total mass of polymer material and electrolyte salt makes from 5 to 75% (wt).

EFFECT: increased ion conductivity and reliability of power supply source.

4 cl, 1 dwg, 6 tbl, 14 ex

FIELD: physics.

SUBSTANCE: described is a transparent optical functional coating distinguished by that, in certain parts of the visible spectrum, especially in the interval which includes wavelengths of at least 50 nm, preferably at least 100 nm, the coating has refraction index n less than 1.3 and contains an electrically conducting polymer which contains polythiophene with repeating structural units of general formula (I) in which A represents an alkylene residue with 1-5 carbon atoms. Also described is a method of preparing said transparent optical functional coating on a substrate, distinguished by that, the coating which contains an electrically conducting polymer is made such that, starting materials for synthesis of the electrically conducting polymer and thiophene of general formula (II), in which A represents an alkylene residue with 1-5 carbon atoms, are deposited on the substrate in form of solutions, and chemical oxidative polymerisation takes place in the presence of an oxidising agent. Described is use of the said transparent optical functional coating as antiglare or infrared radiation reflecting coating on surfaces, coating layer on effective pigments or cladding of optical fibre.

EFFECT: obtaining optical functional coating capable of replacing inorganic functional coatings, with similar or better properties than inorganic coatings.

11 cl, 6 dwg, 1 tbl, 7 ex

FIELD: electrical engineering.

SUBSTANCE: invention relates to electrical engineering, particularly to polymer electrolyte with high ionic conductivity that contains copolymer of ethylene unsaturated compound and carbon monoxide, to method of its production and electrochemical element made thereof. Proposed electrolyte comprises polymer material and electrolyte salt, or polymer material, solvent and electrolyte salt wherein copolymer made up of 50% to 90% molar of ethylene unsaturated compound and 1% to 50% molar of carbon monoxide makes from 66.7 to 100 % by weight of this polymer material. Method is described to produce such polymer electrolyte and electrochemical device made thereof.

EFFECT: high ionic conductivity and reliability of operation of electrochemical elements operated at over 100 V.

11 cl, 1 dwg, 11 tbl, 34 ex

FIELD: chemistry.

SUBSTANCE: invention relates to use of polymer material, and specificaly to use of particulate polymer material as an active agent carrier. The polymer material is a polymer obtained from copolymerisation of pyrrole with quadratic or croconic acid or its derivative.

EFFECT: use in accordance with the invention enables to use polymer material as a composition in form of particles as an absorbent or prolonged release agent.

16 cl, 8 dwg, 1 tbl, 10 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compositions which contain electrically conducting organic materials, particularly to compositions for obtaining hole injecting or hole conveying layers in electroluminescent devices, organic solar cells, organic laser diodes, organic thin-film transistors or organic field-effect transistors, and for making electrodes or electroconductive coatings. The proposed composition contains polythiophene which contains a link of formula (I): , as well as at least one vinyl polymer which contains SO3-M+ - or COO-M+- groups and at least one partially or perfluorinated polymer which contains SO3-M+ - or COO-M+- groups, where M+ denotes H+, Li+, Na+, K+, Rb+, Cs+ , NH4+. Described also is an electroluminescent device in which hole injecting layers contain this composition.

EFFECT: composition provides devices with longer service life.

25 cl, 2 tbl, 4 ex

FIELD: physics.

SUBSTANCE: described is a transparent optical functional coating distinguished by that, in certain parts of the visible spectrum, especially in the interval which includes wavelengths of at least 50 nm, preferably at least 100 nm, the coating has refraction index n less than 1.3 and contains an electrically conducting polymer which contains polythiophene with repeating structural units of general formula (I) in which A represents an alkylene residue with 1-5 carbon atoms. Also described is a method of preparing said transparent optical functional coating on a substrate, distinguished by that, the coating which contains an electrically conducting polymer is made such that, starting materials for synthesis of the electrically conducting polymer and thiophene of general formula (II), in which A represents an alkylene residue with 1-5 carbon atoms, are deposited on the substrate in form of solutions, and chemical oxidative polymerisation takes place in the presence of an oxidising agent. Described is use of the said transparent optical functional coating as antiglare or infrared radiation reflecting coating on surfaces, coating layer on effective pigments or cladding of optical fibre.

EFFECT: obtaining optical functional coating capable of replacing inorganic functional coatings, with similar or better properties than inorganic coatings.

11 cl, 6 dwg, 1 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: method is described for producing electrocatalytic composition based on polypyrrole, involving polymerisation of pyrrole in the presence of platinised soot and surface-active additive, wherein the process is carried out under the effect of a radical initiator in an organic solvent at temperature of approximately 0°C, where the radical initiator is dicyclohexylperoxy dicarbonate, the surface-active additive is a product from reacting tertiary amine (CH3)2NR (R - aliphatic residue C12-14) and propylene oxide in ethyl cellosolve, containing an ionic component - quaternary ammonium base (CH3)2RN+R1(OH)-, where R1- propylene oxide oligomers and a nonionic component - propylene oligomers, and the organic solvent is ethyl cellosolve. After mixing, the components the mixture undergo vacuum treatment at 10-2 mm Hg, and during the initiation process, the system is exposed to an acoustic field with frequency 20 to 22 kHz. Polymerisation process of pyrrole is carried out until obtaining an electrocatalytic composition system which is soluble in organic solvents. In this process electrocatalytic composition is obtained, with the following ratio of said components, wt %: pyrrole 15 to 17; platinised soot 6 to 8; surface-active additive 8-10; dicyclohexylperoxy dicarbonate 5-7; ethyl cellosolve - the rest.

EFFECT: design of an efficient method of producing electrocatalytic composition based on polypyrrole.

2 cl, 2 ex

FIELD: electric engineering.

SUBSTANCE: invention is related to the field of electric engineering, in particular to method for production of special oxidising agents, which in mixtures with original compounds are intended for production of conductive polymers. Oxidising agent is made by means of processing of metal salt and organic or inorganic acid with organic residue by ionite prior to its application in oxidising polymerisation.

EFFECT: invention provides for longer duration of polymerisation with higher quality of surface, and also to mixtures containing such oxidising agents, and their application for production of capacitors with hard electrolyte and conductive coatings.

34 cl, 6 ex, 11 ex

FIELD: physics.

SUBSTANCE: invention is related to electrolytic capacitor that contains layer of metal capable of oxidation, layer of this metal oxide, hard electrolyte and contacts, besides, hard electrolyte used is represented by polythiophens with repeated structural units of common formula (I): . Electroconductive layer is also described with specific electroconductivity of at least 150 Cm/cm, which used, for instance, as antistatic coat, transparent heating element, hard electrolyte of electrolytic capacitors, and also for metallisation of through openings of printed circuit boards, etc. This Electroconductive layer is produced due to the fact that mixture of compounds of common formula (II): oxidising agent together or separately as solution in dissolvent is applied on substrate, and chemical polymerisation is realised on this substrate at temperature from -10°C to 250°C, producing polythiophens with repeated structural units of common formula (I). Polythiophens used in stated invention have high quality and high electroconductivity, which helps to improve uniformity of coats applied on anode body, which shows in reduction of burrs and number of repeating holes, therefore, higher electroconductivity of such coats is provided.

EFFECT: stated electrolytic capacitor, containing hard electrolyte out of these polythiophens, is characterised by reduced value of serial resistance and lower value of residual current.

12 cl, 3 ex, 4 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to 2,2'-di(3,4-alkylenedioxythiophene)s of general formula (I) , where A, R and x have given in description values, which are intended for obtaining electroconducting or semiconducting compounds and valuable semi-products for π-conjugated polymers. Also described is method of their obtaining and method of obtaining poly(3,4-alkylenedioxythophene)s based on them. Claimed method allows to obtain novel 2,2'-di(3,4-alkylenedioxythiophene)s by simplified techniques and extend possibilities of their application.

EFFECT: obtaining agents by simplified techniques and extension of possibilities of their application.

12 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention concerns polymer material displaying optically detectable response to load (pressure) change, including polyurethane elastomer adapted for load change detection, containing aliphatic diisocyanate, polyol with end hydroxyl, and photochemical system including fluorescent molecules for distance probing, modified and transformed into chain-extending diols, with molar diol to polyol ratio approximately within 10:1 to 1:2 range, and photochemical system selected out of group of exciplex and fluorescence resonance energy transfer (FRET) systems. The invention also concerns solution containing the said polymer material, and polymer material displaying detectable response to pressure change, including polyacryl or silicon elastomer and photochemical system including definite number of fluorescent molecules for distance probing, modified for penetration into the said elastomer, selected out of group including exciplex and fluorescence resonance energy transfer (FRET), and solution containing this polymer material. To eliminate oxygen sensitivity in pressure detection the material includes photochemical system selected out of group including exciplex and fluorescence resonance energy transfer (FRET). Systems including these photochemical systems enable fast response to pressure change; in addition, compression of material containing these systems is reversible, therefore elimination of oxygen influence on pressure change detection allows shorter response time and higher sensitivity when the claimed material is used.

EFFECT: increased material sensitivity to loads and reduced sensitivity to oxygen presence.

24 cl, 2 ex, 6 dwg

FIELD: chemistry.

SUBSTANCE: description is given of the method of obtaining a water dispersion containing a complex of poly(3,4-dialkoxythiophen) and polyanion, including polymerisation of 3,4-dialkoxy-thiophen, with general formula (I): where R1 and R2 independently represent a hydrogen atom or alkyl with 1-4 atoms of carbon, or together form an alkylene group with 1-4 carbon atoms, which can be substituted in the presence of polyanion with use of peroxodisulphuric acid as an oxidiser in a water solution with pH equal to or less than 1.5, or use of an oxidiser in a water solution, in which acid has been added, chosen from a group, consisting of water soluble inorganic acids and water soluble organic acids, in quantity providing for pH of the obtained reaction mixture equal to 1.5 or less. Description is also given of the composition of the coating, containing water dispersion which contains the complex of poly(3,4-dialkoxythiophen) and polyanion. The substrate with a conducting transparent film, obtained through deposition of the above given composition is also described.

EFFECT: obtaining of water dispersion, providing the coating obtained from it with lower surface resistivity.

4 cl, 2 tbl, 1 dwg, 18 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of neutral polythiophenes. Invention relates to neutral polythiophenes of the general formula (I): wherein R1 and R2 mean independently of one another hydrogen atom or alkyl with 1-9 carbon atoms being in case when R1 means hydrogen atom then R2 can mean -CH2-O-R3 also wherein R3 means hydrogen atom or alkyl with 1-9 carbon atoms, cycloalkyl or aralkyl; n means a number from 2 to 200. These compounds are soluble in organic solvents and free of organically bound halogen. Except for, invention relates to a method for synthesis of neutral polythiophenes. Neutral polythiophenes can be used in different fields, for example, in memory device, in optical transformation of signal, blocking electromagnetic radiations and in transformation of solar energy in over-charged batteries, light-diode, field transistors, printing boards, sensitive units, condensers and others.

EFFECT: valuable technical properties of compounds, improved method of synthesis.

16 cl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention refers to compounds of the formula (I): , where R1 is C1-C8alkyl optionally substituted with one to three substitutes selected out of substitute group A; R2 is C1-C6alkyl or C1-C6alkoxyC1-C6alkyl; R3 is C1-C6alkyl or C1-C6alkoxy; or R2 and R3 together with adjoining carbon atoms form optionally substituted non-aromatic 5-10-member carbon ring; R4 is hydrogen; G is group represented by the formula: or the rest as provided in the invention claim; and to pharmaceutical composition, application of claimed compounds, and method of atopic dermatitis prevention or treatment.

EFFECT: novel compounds useful as atopic dermatitis treatment medication and antipruritic medicines.

24 cl, 75 ex, 290 tbl

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