Composition 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 or for making electrodes or electoconductive coatngs, as well as electroluminescent device

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

 

The invention relates to containing conductive organic materials, compositions, in particular to the composition to obtain an injecting holes or hole transporting layers in electroluminescent devices, organic solar cells, organic laser diodes, organic thin-film transistor or an organic field-effect transistors, or to obtain electrodes or conductive coatings, as well as to the electroluminescent device.

The electroluminescent unit (ELU) is characterized by the fact that it is when applying an electrical voltage when current flows emits light. Such devices have long been known under the name “light-emitting diodes or light-emitting diodes (LED = light emitting diodes"). Light emission occurs as a result of recombination of the positive charges (holes, "holes") and negative charges (electrons "electrons") with the emission of light.

Usually used in the technique of light-emitting diodes (LEDs) are in the vast majority of inorganic semiconductor materials. However, for several years known as electroluminescent device in which the main components are organic materials.

These organic electroluminescent devices contain, as a rule, one or more layers of organic is connected to the th, carrying charges.

Principal layered structure electroluminescent device includes, for example, the following components:

1. The carrier substrate.

2. The base electrode.

3. Layer that injects holes.

4. Layer that transports holes.

5. The emitter layer.

6. Layer that transports electrons.

7. Layer that injects electrons.

8. Toelectron (Topelectrode).

9. The contacts.

10. Shell, sealing the case.

This structure represents the most detailed case, and can be simplified by not separate layers so that one layer performs several tasks. In the simplest case, the electroluminescent device consists of two electrodes between which the organic layer that performs all functions, including the function of the emission light.

However, in practice it turned out that to increase the brightness of the layers in electroluminescent devices, injects electrons and/or holes, should be particularly effective.

From European patent application EP-A-686662 known to use special mixtures of electrically conductive organic polymeric conductors, such as poly(3,4-ethylenedioxythiophene) and, for example, polyhydroxylated connection or lactams, as electrodes in electroluminescent indicators. However, in practice it turned out that these electrodes, especially the La widescreen indicators have insufficient conductivity. On the contrary, for small indicators (surface illumination of less than 1 cm2their conductivity is sufficient.

From German patent application DE-A-19627071 known application of polymeric organic conductors, such as, for example, poly(3,4-ethylenedioxythiophene), as a layer that injects holes. Thanks to the use of such conductors brightness electroluminescent indicators in comparison with structures without the use of intermediate organic polymer layers is noticeable. Reducing the particle size of the dispersions of poly(3,4-alkylenedioxy) allows you to purposefully set the conductivity to the preset value. Thereby possible to reduce electrical crosstalk, in particular, the indicators with passive matrix (EP-A-1227529). However, the service life of such indicators for many practical applications is still insufficient.

The present of the invention is to provide a composition for obtaining an injecting holes or hole transporting layers in electroluminescent devices, organic solar cells, organic laser diodes, organic thin-film transistor or an organic field-effect transistors, or to obtain electrodes or conductive coatings, which provides cited utim objects over a long service life.

This problem is solved by using the proposed composition to obtain an injecting holes or hole transporting layers in electroluminescent devices, organic solar cells, organic laser diodes, organic thin-film transistor or an organic field-effect transistors, or to obtain electrodes or conductive coatings containing polythiophene derived, and the composition contains as polythiophenes derivative, at least one of polythiophene containing the repeating unit of General formula (I),

in which

And denotes optionally substituted C1-C5-alkalinity residue, preferably optionally substituted ethylene or propylene residue, particularly preferably 1,2-atandroy the rest,

R denotes a linear or branched C1-C18is an alkyl residue, preferably a linear or branched C1-C14is an alkyl residue, particularly preferably a methyl or ethyl residue, cycloalkenyl balance with 5-12 carbon atoms, an aryl residue with 6 to 14 carbon atoms, With7-C18-Aracely residue, a hydroxyalkyl residue with 1 to 4 carbon atoms or hydroxyl residue,

x denotes an integer from 0 to 8, before occhialino 0, 1 or 2, particularly preferably 0 or 1, and if attached to a few residues R, these residues may be the same or different,

and additionally contains at least one containing SO3-M+or COO-M+-groups of the polymer, and M+denotes the N+Li+, Na+To+, Rb+Cs+or NH4+preferably N+, Na+or+and at least one contains SO3-M+or COO-M+groups, partially or perfluorinated polymer, and M+denotes the N+Li+, Na+To+, Rb+Cs+or NH4+preferably N+, Na+or+moreover , the mass ratio of polythiophene to said polymer is from 1:2 to 1:25 and the said partially or perfluorinated polymer is from 1:1 to 1:50.

General formula (I) should be understood that the substituent R may be attached to Allenova residue And x times.

A composition within the invention is any mixture of the three components of polythiophene A), polymer b) and partially or perfluorinated polymer (C) is in the form of a solid, solution or dispersion.

The term “substituted” is here and hereinafter, unless otherwise specified, should be understood as a substituted group, SEL is Anna from a number of: alkyl, preferably an alkyl group with 1-20 carbon atoms, cycloalkyl, preferably cycloalkyl group with 3-20 carbon atoms, aryl, preferably aryl group with from 5 to 14 carbon atoms, a halogen group, preferably chlorine, bromine, iodine, ether group, thioester group, a disulfide group, sulfoxide group, alphagraph, amino group, aldehyde group, ketogroup, ester group, cyano, alkylsilane and alkoxysilane group, and carboxylamide group.

In preferred embodiments, the proposed composition of at least one polythiophene containing the repeating unit of General formula (I)is polythiophenes containing the repeating unit of General formula (Ia):

in which

R and x have the above meaning.

In a particularly preferred compositions according to the above description, x represents 0 or 1. In the case when x=1, R particularly preferably represents methyl or hydroxymethyl.

In other preferred embodiments, the proposed composition of at least one polythiophene A)containing the repeating unit of General formula (I)is polythiophenes containing the repeating unit of General formula (Iaa):

Under the prefix poly - in the context of the present invention the SL is blowing to understand the polymer, respectively polythiophene contains more than one identical or different recurring link. Just polythiophene contain n repeating units of General formula (I), and n can be an integer from 2 to 2000, preferably from 2 to 100. The repeating unit of General formula (I) can be within the same polythiophene respectively the same or different. Preferred are polythiophene, each of which contains the same repeating units of General formula (I).

Under the duplicate links in the context of the present invention should be understood units of General formula (I), (Ia) or (Iaa), hereinafter referred to as a General term recurring units of General formula (I), regardless of whether they are contained in polythiophene once or several times. This means that the units of General formula (I) should be understood as repeating units, even when they are contained in polythiophene only once.

The compositions according to the invention can also be such compositions, which, together with at least one of the above polythiophenes A)containing the repeating unit of General formula (I) in the mixture that contain other conductive polymers, such as polyaniline or polypyrrole.

At the end groups each polythiophenes preferably contains hydrogen.

Just polythiophene A) contains n stages is arausiaca units of General formula (I), moreover, n is preferably an integer from 2 to 1000, preferably from 3 to 100, particularly preferably from 4 to 15.

Alkionovymi residues with 1-5 carbon atoms And are, in particular, methylene, ethylene, n-propylene, n-butylene or n-pentile. Alkyl with 1-18 carbon atoms means, in particular, linear or branched alkyl residues, for example, methyl, ethyl, n - or isopropyl, n-, ISO-, sec-or tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl, cycloalkyl with 5-12 carbon atoms denotes cycloalkyl residues, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclonona or cyclodecyl, with aryl of 5-14 carbon atoms denotes aryl residues, for example phenyl or naphthyl, and C7-C18-aralkyl stands With7-C18-kalkilya residues, e.g. benzyl, o-, m-, p-tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-xylyl or mesityl. The above list only serves as an example to explain the invention and should not be construed as exhaustive.

Getting the above polythiophenes A)containing the repeating unit of General formula (I), essentially as described in European the th patent application EP-A-440957.

The polymerization of the corresponding Monomeric compounds is carried out using suitable for this purpose oxidants in suitable solvents. Examples of suitable oxidizing agents are salts of iron (III), in particular, FeCl3and salts of iron (III) with aromatic and aliphatic sulfonic acids, peroxide carbon, K2Cr2O7, K2S2O8, Na2S2O8, KMnO4alkylphenolate and persulfates of alkali metals or ammonium, or mixtures of these oxidants. Other suitable oxidizing agents are described, for example, in: Handbook of Conducting Polymers (Ed. Skotheim, T.A.), Marcel Dekker: New York, 1986, Vol.1, 45-57. Particularly preferred oxidizing agents are FeCl3, Na2S2O8and K2S2O8or mixtures thereof. The polymerization is preferably carried out at a temperature from -20 to 100°C. Particularly preferred are reaction temperatures from 20 to 100°C. optionally, the reaction solution is then treated with at least one ion exchanger.

Suitable solvents for the above reaction are, for example, polar solvents such as water, alcohols, such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, datetoday alcohol, ethylene glycol, glycerin, or mixtures thereof. Also suitable aliphatic ketones, such as acetone and methyl ethyl ketone, aliphatic shall Italy, such as acetonitrile, aliphatic and cyclic amides such as N,N-dimethylacetamide, N,N-dimethylformamide (DMF) and 1-methyl-2-pyrrolidone (NMP), ethers, such as tetrahydrofuran (THF), and sulfoxidov, such as dimethylsulfoxide (DMSO), or mixtures thereof with each other or with the above solvents.

The corresponding Monomeric compounds to obtain polythiophenes A)containing the repeating unit of General formula (I)are known. Their reception is possible, for example, by the reaction of alkaline salts of esters of 3,4-dihydroxytoluene-2,5-dicarboxylic acid with the appropriate alkylene-dihalogenide and subsequent decarboxylation of free 3,4-(alkylenedioxy)-thiophene-2,5-dicarboxylic acid (see, for example, Tetrahedron 1967, 23, 2437-2441 and J. Am. Chem. Soc. 1945, 67, 2217-2218).

The resulting polythiophene very well dissolved or dispersed in polar solvents or mixtures of solvents. The compositions according to the invention contain, along with at least one partially or perforated polymer), at least one polymer B)containing SO3-M+or COO-M+-group. Suitable polymers)containing SO3-M+or COO-M+group, is preferably such polymers that do not contain a fully conjugate main chain; hereafter they briefly indicated the AK are not conjugate. As examples of suitable polymers containing SO3-M+or COO-M+-the group should be called polymeric carboxylic acids, such as polyacrylic acid, polymethacrylic acid or primaline acid, or polymeric sulfonic acids, such as polystyrenesulfonate and polyvinylacetate. Next can be considered also copolymers vinylcarbazole and vinylsulfonic acid polymerized with other monomers such as esters of acrylic acid and styrene. Particularly suitable are polystyrenesulfonate, copolymer of styrelseledamot and maleic acid or poly-(vinylsulfonate). The most preferred compositions are characterized in that they contain as at least one containing SO3-M+or COO-M+-groups of the polymer) polystyrenesulfonate (PSS).

Preferably these polymers In) soluble or capable of dispergirujutsja in polar solvents such as water, alcohols, such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, deacetyltaxol, ethylene glycol, glycerol, aliphatic ketones, such as acetone and methyl ethyl ketone, aliphatic NITRILES, such as acetonitrile, aliphatic and cyclic amido, such as N,N-dimethylacetamide, N,N-dimethylformamide (DMF) and 1-methyl-2-pyrrole is he (NMP), ethers, such as tetrahydrofuran (THF), and the sulfoxidov, such as dimethylsulfoxide (DMSO), or containing their mixtures, preferably in water, alcohols, such as methanol, ethanol, 2-propanol, n-propanol and n-butanol, or mixtures of them.

Especially suitable compounds as described above are characterized in that they contain as at least one containing SO3-M+or COO-M+group partially or perfluorinated polymer), for example, such polymers which contain recurring units of the formulas (II-a), (II-b):

in which Rfdenotes the residue with at least one, preferably 1-30 repeating units of the formula (II-c)

Such perfluorinated polymers are, for example, polymers, commercially available under the trade name Nation® or in dissolved form under the trade name Liquion®.

In particularly preferred embodiments, the new composition contains as at least one containing SO3-M+or COO-M+-groups of the polymer (C) Nafion® (a copolymer of tetrafluoroethylene and triftorbyenzola ether poly-(geksaftorpropilenom)-mono-(tetraferriphlogopite)-ether).

Particularly preferably the compounds which contain as containing SO3-M+or COO-M+-groups of the polymer) polystyrenesulfonate (PSS) and as containing SO3-M+or COO-M+group partially or perfluorinated polymer (C) Nafion® (a copolymer of tetrafluoroethylene and triftorbyenzola ether poly-(geksaftorpropilenom)-mono-(tetraferriphlogopite)-ether).

The molecular mass of PolicyKit is mainly from 1000 to 2000000, particularly preferably from 2,000 to 500,000. Polyacid or their salts with alkaline metals are commercially available, for example, polystyrenesulfonate and polyacrylic acid, or may be obtained by known methods (see, for example, Houben Weyl, Methods der organischen Chemie, Bd. E 20, Makromolekulare Stoffe, Teil 2, (1987), S.1141 u. f.). Most preferred are compounds, in which the mass ratio of polythiophene (polythiophene) (A) to contain SO3-M+or COO-M+-groups of the polymer (the polymer) is in the range from 1 to 2 (1:2) to 1 : 20 (1:20).

Further preferred are compounds, in which the mass ratio of polythiophene (polythiophene) (A) to contain SO3-M+or COO-M+group partially or fully fluorinated polymer (polymers) (C) ranges from 1 to 2 (1:2) to 1 : 30 (1:30).

All any to whom Binali both mass relations of polythiophene (polythiophene) (A) to contain SO 3-M+or COO-M+-groups of the polymer (polymers) and polythiophene (polythiophene) (A) to contain SO3-M+or COO-M+group partially or perfluorinated polymer (polymers) can be implemented in the preferred compositions and on the basis of this statement should be considered as exposed.

Further, the new compositions can optionally contain at least one polar diluent (D) (polar solvent). Under the polar diluents (D) (polar solvents) in the context of the present invention should be understood solvents with solubility parameter δ 16 MPa1/2and above, preferably 19 MPa1/2and above. Measurement of parameters δ solubility, usually carried out at standard temperature (20°C). About the measurement and calculation of the parameters δ solubility look: J.Brandrup et al. Polymer Handbook, 4thEd., 1999, VII675-VII/688.

The parameters δ solubility is presented in tabular form, see, for example: J.Brandrup et al., Polymer Handbook, 4thEd., 1999, VII688-VII/697. Preferred polar solvents (D) are water, alcohols such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, di-acetylchol, ethylene glycol, glycerol, aliphatic ketones, such as acetone and methyl ethyl ketone, aliphatic NITRILES, such as acetonitrile, aliphatic is cyclic amides, such as N,N-dimethylacetamide, N,N-dimethylformamide (DMF) and 1-methyl-2-pyrrolidone (NMP), ethers, such as tetrahydrofuran (THF), and sulfoxidov, such as dimethylsulfoxide (DMSO), or containing a mixture thereof. Especially preferred polar solvents (D) are water, alcohols or contain mixtures thereof, most preferred are water, methanol, ethanol, n-propanol, 2-propanol or n-butanol or contain mixtures thereof. In preferred embodiments, the new compositions contain as the polar solvent (D) a mixture of water and at least one alcohol.

Such new preferred compositions containing at least one polar diluent (D), contain preferably from 99,99% to 80% (mass.), particularly preferably from 99,8% to 95% (mass.) the polar solvent (polar solvent) and have a solids content of from 0.01 to 20% (mass.), particularly preferably from 0.2 to 5% (mass.), i.e. contain in the amount of from 0.01 to 20% (mass.), particularly preferably from 0.2 to 5% (mass.) polythiophene (polythiophene) (A), containing the SO3-M+or COO-M+-groups of the polymer (polymers) b) and C) and optionally other components, such as binders, crosslinking agents and/or surface-active substances (surfactants), in dissolved and/or dispersed form.

The viscosity at 20°C new preferred compositions are provided which, at least one polar diluent (D), lies between the viscosity of the diluent and 200 MPa·s, preferably less than 100 MPa·S.

To obtain a solution with the desired concentration of solids and the desired viscosity can be removed from the composition a certain amount of diluent by distillation, preferably under vacuum, or in other ways, for example by ultrafiltration.

In the compositions according to the invention can be added, in addition, organic, polymeric binders and/or organic, low-molecular cross-linking agents or surfactants. Appropriate binders are described, for example, in European patent application EP-A-564911. As an example here can be called polyvinylcarbazole as a binder, silanes such as Silquest® A-187, OSi specialities) or surfactant as a binder, such as Fluortensid FT 248 (Bayer AG).

The composition may preferably contain a small amount of ionic impurities within the limits described in European patent application EP-A-991303. Preferably, the content of ionic impurities in the composition is less than 1000 parts per million of Compounds according to the invention can be obtained in a simple way. For example, you can mix a ready-made composition comprising at least one containing SO3-M+or COO-M+-groups of the polymer) and at least one polythiophene is), with at least one partially or fully fluorinated, containing SO3-M+or COO-M+-group polymer (C), and the mixture is added optionally to at least one diluent, preferably fully or partially dissolving or dispersing in at least one diluent. Also you can pre-mix, at least one ready-made composition, which contains contains SO3-M+or COO-M+-groups of the polymer) and at least one polythiophene A), with at least one diluent (D), preferably fully or partially dissolving or dispersing it in at least one diluent (D)dissolving or dispersing in a solvent, at least one containing SO3-M+or COO-M+groups, partially or perfluorinated polymer (C) and solution (solutions) and/or the variance (dispersion) then mix. If necessary, a diluent (D), or a mixture of diluents can then be fully or partially removed (deleted) from this mixture, for example, by distillation or other means.

Manufactured using the proposed composition of the electroluminescent device (ELU) are used as display devices (displays), for example, flat screen the fuck of such devices, as portable compact personal computer (laptop), pager, mobile phone, navigation devices, car radios, instrument panels of automobiles, or as a flat emitters, for example, lamps, fluorescent surfaces, backlight for liquid crystal displays, signage.

In particular, electroluminescent devices (ELU) with an injecting hole layer containing the composition according to the invention are distinguished by high luminosity (intensity of illumination) and significantly longer service life in comparison with the known electroluminescent devices (ELU).

Therefore, an object of the present invention is also the electroluminescent unit (ELU), in particular light-emitting diode, which contains an injecting hole layer containing the composition according to the invention. Preferably such devices are electroluminescent device (ELU)containing at least two electrodes, of which, optionally, at least one printed on, if necessary, a transparent substrate, at least one emitter layer between the two electrodes and at least one injects holes layer between one of the two electrodes and the emitter layer, wherein an injecting hole layer contains a composition according to the invention.

In the manufacture of electroluminescent devices (ELU), for example, electroluminescent display devices, large format, it is advisable that at least one current-carrying electrode consisted of a transparent and conductive material. As the transparent and conductive electrode materials are suitable, for example,

a) metal oxides, such as indium oxide and tin (ITO), tin oxide (NESA), doped tin oxide, doped zinc oxide, etc.;

b) semi-transparent metallic film, for example, Au, Pt, Ag, Cu, etc.;

c) semi-transparent, conductive polymers, for example, polythiophene, polyaniline, polypyrrole etc.

When it comes to the electrode not comprising one of the foregoing transparent and conductive materials, we mean mainly the metal electrode, in particular, a metal cathode.

Suitable materials for metal cathodes are common for the electro-optical structures materials known to the specialist. As the metal of the cathode is preferably treated metals with minor work function such as Mg, CA, BA, or metal salts, such as LiF. As, if necessary, the transparent substrate is suitable, for example, glass, thin glass (flexible glass or plastic, preferably a plastic film.

Particularly suitable materials for the substrate floor are the carbonates, polymers of esters, such as, for example, PET and PEN (polyethylene terephthalate, respectively polyethyleneterephthalate), copolycarbonate, polyacrylate, polysulfone, polyethersulfone (PES), polyimide, polyethylene, polypropylene, or cyclic polyolefins, respectively cyclic refinability (SOS), hydrogenated strapriley or hydrogenated styrolcopolymere.

Suitable polymeric substrates can be, for example, films such as polymeric ester film, polyethersulfone film (PES) company Sumitomo or polycarbonate film from Bayer AG (Makrofol®).

Between the substrate and the electrode may be a layer of tools that enhance adhesion. Suitable means, which increases the adhesion, are, for example, silane. Preferred epoxysilane, such as, for example, 3-glycidoxypropyltrimethoxysilane (Silquest® A-187 by OSI specialities). Can be applied and other adhesive compositions with hydrophilic surface properties. So, for example, describes a thin layer of PEDT:PSS as a suitable adhesive composition for PEDT (Hohnholz et al., Chem. Commun. 2001, 2444-2445). The emitter layer electroluminescent device according to the invention contains at least one emitter material. Suitable materials for the emitter are materials commonly used for electro-optical structures is well-known specialist. As materials for the emitter preferably can be considered conjugate polymers such as polyphenylenevinylene and/or polyfluorene, such as, for example, described in international application WO-A 90/13148 derivatives polyparaphenylene and derivatives polyfluorene, or the emitters of the class of low-molecular emitters, referred to in professional circles as "small molecules" (small molecules), such as aluminum complexes, for example, Tris(8-hydroxyquinolinato)-aluminum (Alq3), fluorescent dyes, for example, chinagreen, or phosphorescent emitters, for example, Ir(RDD)3. Materials for emitters described, for example, in German patent application DE-A 19627071.

In addition to the above layers, such electroluminescent puff design (ELU) may contain other functional layers, for example, other intermediate layers that injects charge, for example injects an electron transporting charge or blocking the charge. Such layered structures known to the expert and are described, for example, in: J.R.Sheats et al., Science 273, (1996), 884. The layer can also perform several tasks. For example, the above-mentioned emitter materials in combination with transporting holes of the intermediate layer can be located between an injecting hole layer and the emitter layer (see, for example, patents school is US 4539507 and US 5150006).

The principle of obtaining such ELU well-known specialist. They can be obtained, for example, by applying to the substrate electrode from a solution or dispersion, or by spraying. Metal oxide or semi-metal film electrodes are applied to the substrate preferably by spraying, a translucent conductive polymer electrodes, in contrast, preferably applied from solution or dispersion. If necessary, before the deposition of electrode material on a substrate may be applied by spraying or from a solution or dispersion is a tool that improves adhesion. Some of these are covered with the electrode material of the substrate is already commercially available (for example, glass, ITO-coated glass substrate). Then the electrode may be caused to an injecting hole layer, which in the case of an electroluminescent device according to the invention with an injecting hole layer containing the composition, is carried out mainly from a solution or dispersion. In an injecting hole layer is then applied to the other layers in the above sequence, given the fact that the individual layers can be excluded depending on the applied material from a solution or dispersion or coating. Then layered the device is supplied with contacts or is installed in the capsule.

An injecting hole is Loy, containing the composition according to the invention, receive by known technologies. For this composition, if necessary, in a solvent is applied in the form of a film on the electrode, preferably on the base electrode. As the solvent usable above-mentioned polar solvents, preferably water, alcohols or mixtures thereof. Suitable alcohols are, for example, methanol, ethanol, n-propanol, 2-propanol and n-butanol.

The use of these solvents has the advantage that other layers can be applied from organic solvents, such as mixtures of aromatic hydrocarbons, without affecting them on an injecting hole layer.

The proposed composition - if necessary, the solvent can be uniformly distributed on the electrode, for example, printed wiring methods, in particular, to coating by centrifugation, watering, using a doctor blade, printing, coating watering, etc. and Then the layers can be dried at room temperature or at temperatures up to 300°C, preferably from 100 to 200°C.

The proposed composition - if necessary, the solvent may be structured fashion printed using techniques such as ink-jet spray (ink-jet). This method is known to the expert and described in the application example water-soluble and dispersed polythiophenes, such as the 3,4-polyethyleneoxide: polystyrenesulfonate (PEDT-PSS) in the journal Science, Vol.279, 1135, 1998, and German patent application DE-A 19841804.

Before applying the proposed structures - if necessary, the solvent is preferably filtered through a filter.

Particularly well filtered with purpose cleaning compositions are obtained, for example, in the case where the solvent (D) is used that contains the SO3-M+or COO-M+-groups of the polymer (polymers) In) in an amount of preferably from 1 to 30 mass parts, particularly preferably from 2 to 25 mass parts, in terms of mass fraction of polythiophene containing (polythiophenes containing) the repeating unit of General formula (I). The thickness of an injecting hole layer is, for example, from 3 to 500 nm, preferably from 10 to 200 nm.

The impact of an injecting hole of the layer containing the composition, the properties of the electroluminescent device can be checked by the special design of this proposed electroluminescent device. With this purpose, an injecting hole layer is applied by means of a device for coating by centrifugation on clean wet chemical method, the ITO-coated substrate. Then the layer is dried at 100-200°C for 5 minutes. The thickness of the layer is depending on the rotation speed from 20 to 300 nm. As the emitter layer is applied 1% (mass.)-s ' solution of the emitter mater the Ala-based polyfluorene (Green LUMATION 1300™ from Dow Chemical Company) in xylene. The thickness of the emitter layer is usually 60-120 nm. Finally as the cathode sprayed layer VA in the thickness of 5 nm and then an Ag layer thickness of 200 nm. By closing contacts made of indium oxide and tin (ITO) anode and a metal cathode is removed using a recording device and a calibrated photodiode characteristics current-voltage-brightness and measure the time of service. To this end through the device pass DC or AC electrical current and observing the change in the voltage and brightness depending on time.

Organic light-emitting diodes according to the invention are characterized by long service life, high intensity of illumination, low applied voltages and high rectifier. In comparison with known LEDs with an injecting hole layers, made of a dispersion of poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDT-PSS) (Baytron® P, H.C.Starck GmbH), it has been unexpectedly discovered that the terms of the service we offer organic light-emitting diodes with an injecting hole layer containing the composition according to the invention is much higher.

Examples

Example 1

Obtaining a composition of poly-(3,4-ethylenedioxythiophene)/polystyrenesulfonate and perfluorinated polymer

40 g of 1.32%aqueous solution of poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate (H.C.Starck GmbH, experienced product Baytron® P TPAI 4083, the mass ratio of PEDT/PSS 1:6) was mixed with 9,96 g and 5.30% (mass.)-aqueous solution of the Nation® in a mixture of lower aliphatic alcohols and water (perfluorinated ion-exchange resin Nation®, 5% (mass.) in the lower aliphatic alcohols/H2O, CAS - No. 66796-30-3, Aldrich-Best. - Nr. 27, 470-4, the solids content according to the control dimension is equal and 5.30% (mass.)). The mass ratio of PEDT/PSS/Nafion® is 1:6:7.

Example 2

The composition according to the invention from example 1 is used for manufacturing organic light-emitting diode (osid). Getting acid includes the following stages:

1. Preparation of ITO-coated substrates

ITO-coated glass (Merck Blazers AG, FL, Part. No 253674 XO) cut into pieces (substrates) with a size of 50 mm by 50 mm ITO-layer structure in the usual way with the use of photoresist followed by etching in a solution of FeCl3. Isolated ITO strips have a width of 2.0 mm, the Substrate is then cleaned in a 3% aqueous solution of mukataa in an ultrasonic bath for 15 minutes. After that, the substrate is rinsed with distilled water and centrifuged dry in a centrifuge. This process of washing and drying is repeated 10 times. Directly before coating ITO-covered hand cleaned for 10 minutes in a UV/ozone reactor (PR-100. UVP Inc., Cambridge, UK).

2. Applying an injecting hole layer

Filter approximately the 10 ml of the proposed composition of example 1 (Millipore HV, 0.45 µm). The cleaned ITO-coated substrate is placed on the coating machine, and distribute the filtered solution on ITO-coated side of the substrate. Then the supernatant solution for 30 seconds, centrifuged by rotating the plate at 800 rpm with closed lid. After that covered so the substrate is dried for 5 minutes at 200°C on the heating plate. The total layer thickness of 85 nm (Tencor, Alphastep 500).

3. The application of the emitter layer

5 ml of 1% (mass.) xylene solution of the Green emitter LUMATION 1300™ (Dow Chemical Company) filter (Miliipore HV, 0.45 μm) and distributed to dried injects holes layer. This and all subsequent phases of the process are conducted in an atmosphere of pure nitrogen (Inert-gas-Gloveboxsystem, M.Braun, Garching). An injecting hole layer before it again dried in the device Glovebox for 5 minutes at 200°C. Then the supernatant solution emitter for 30 seconds, centrifuged by rotating the plate at 400 rpm with closed lid. After that covered so the substrate is dried for 15 minutes at 130°C on a heating plate. The total layer thickness of 185 nm.

4. Applying a metal cathode

On the emitter layer of sprayed metal electrode. The substrate is placed, the emitter layer down to strip the mask with wide strips of 2.0 mm, which is focused ver talino to the ITO strips. Two nepalaya boats at a pressure of p=10-3PA sequentially sprayed layer VA in the thickness of 5 nm and then an Ag layer thickness of 200 nm. The speed of deposition is 10 Å/s for VA and 20 Å/s for Ag. The active surface of the glow in the point of intersection of the two electrodes is 4 mm2.

5. Encapsulation of acid

Easily oxidized cathodes are protected from corrosion by sealing the capsule. With this purpose, the polymer layers are removed manually with a scalpel from the edges of the substrate and using epoxy glue (UHU Plus, UHU, D) adhesively bonded metal cap (35 mm × 35 mm × 2 mm) as protection. Metal cap provide additional absorber fluid (GDO/CA/18×10×0,4, SAES Getters S.p.A., Italy).

6. Characterization of acid

Both electrodes of the organic LED link (contact) wires of the power source voltage. The positive pole is connected to the ITO electrode, the negative pole with a metal electrode. Recorded the dependence of the current on organic led and the intensity of electroluminescence from strain (the proof is obtained using a photodiode (EG&G C30809E)). Then determine the lifespan, passing a constant current I=0,32 mA (8 mA/cm2) through the device and observing the change in the voltage and light intensity depending on time.

Comparative example 2.1

p> Getting acid using poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate as an injecting hole of the layer.

The process is conducted as described in example 2, except for the following differences in stage 2:

2. Applying an injecting hole layer

Filter about 10 ml of a 1.3% solution of poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate (..Starck GmbH, Baytron® P TP AI 4083) (Millipore HV, 0.45 μm). ITO-coated substrate is then placed on the coating machine, and distribute the filtered solution on ITO-coated side of the substrate. Then the supernatant solution for 30 seconds, centrifuged by rotating the plate at 600 rpm with closed lid. After that covered so the substrate is dried for 5 minutes at 200°C on the heating plate. The layer thickness of 85 nm.

Applying a metal cathode according to the stage 4 was produced in conjunction with the installation of layers of example 2, to enable comparison.

The results of measurements of the lifetime at a constant current (8 mA/cm2devices of example 2 and comparative examples 2.1 are given in table 1.

Table 1
t=0t=C
U/[V]L/[Rel. frame link guides.]U/[V]L/[Rel. frame link guides.]
Acid from example 23,66for 6.813,886,61
Acid from EUR. when
measure 2.1
3,71of 4.664,132,59

We offer the electroluminescent device with an injecting hole layer containing the composition according to the invention (example 1), is more effective and has a significantly longer service life compared to an electroluminescent device containing an injecting hole layer made of a known material (PEDT:PSS from comparative example 2.1). After 260 hours long test the proposed device shows not only a smaller reduction in the intensity of electroluminescence, but also a smaller increase of the voltage.

Example 3.1

Obtaining a composition of poly-(3,4-ethylenedioxythiophene)/polystyrenesulfonate and perfluorinated polymer

15 g about solengo, 1,36%aqueous solution of poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate (..Starck GmbH, Baytron® P TP AI 4083 desalted product) is mixed with 4.09 g of a solution of Nafion® (Liquion® 1000, a 5% solution in 2-propanol/N2Oh, 1000 Aq, Ion Power Inc., USA). The mass ratio of PEDT/PSS to Nafion® corresponds to 1:1.

Example 3.2

Obtaining a composition of poly-(3,4-ethylenedioxythiophene)/polystyrenesulfonate and perfluorinated polymer

12 g of demineralized, 1,36%aqueous solution of poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate (..Starck GmbH, Baytron® P TP AI 4083 desalted product) is mixed with 3.42 g of a solution of Nafion® (Liquion® 1100, a 5% solution in 2-propanol/H2O, 1000 Aq, Ion Power Inc., USA). The mass ratio of PEDT/PSS to Nafion® corresponds to 1:1.

Example 4.1

The composition according to the invention from example 3.1 is used for the manufacture of organic light-emitting diode (osid). The process is conducted as described in example 2, except for the following differences in stage 2:

2. Applying an injecting hole layer

Filter about 10 ml of the proposed composition of example 3.1 (Millipore HV, 0.45 μm). The cleaned ITO-coated substrate is placed on the coating machine, and distribute the filtered solution on ITO-coated side of the substrate. Then the supernatant solution for 30 seconds, centrifuged by rotating the plate at 800 rpm with closed lid. After that covered so under the oku dried for 5 minutes at 200°C on the heating plate. The total layer thickness of 85 nm (Tencor, Alphastep 500).

Example 4.2

The composition according to the invention from example 3.2 is used for the manufacture of organic light-emitting diode (osid). The process is conducted as described in example 2, except for the following differences in stage 2:

2. Applying an injecting hole layer

Filter about 10 ml of the proposed composition of example 3.2 (Millipore HV, 0.45 μm). The cleaned ITO-coated substrate is placed on the coating machine, and distribute the filtered solution on ITO-coated side of the substrate. Then the supernatant solution for 30 seconds, centrifuged by rotating the plate at 800 rpm with closed lid. After that covered so the substrate is dried for 5 minutes at 200°C on the heating plate. The total layer thickness of 85 nm (Tencor, Alphastep 500).

Comparative example 4.3

Getting acid using poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate as an injecting hole layer:

The process is conducted as described in example 2, except for the following differences in stage 2:

2. Applying an injecting hole layer

Filter about 10 ml of demineralized 1,36-% solution of poly(3,4-ethylenedioxythiophene)/polystyrenesulfonate (..Starck GmbH, Baytron® P TP AI 4083) (Millipore HV, 0.45 μm). ITO-coated substrate is then put on the paint centrifuges and distribute the filtered solution on ITO-coated side of the substrate. Then the supernatant solution for 30 seconds, centrifuged by rotating the plate at 600 rpm with closed lid. After that covered so the substrate is dried for 5 minutes at 200°C on the heating plate. The layer thickness of 85 nm.

The application of metallic cathodes according to stage 4 was produced in conjunction with the installation of layers of examples 4.1, 4.2 and comparative example 4.3:

The results of measurements of the lifetime at a constant current devices (I=24 mA/cm2from examples 4.1, 4.2 and comparative example 4.3 are given in table. 2.

Table 2
t=0t=100 h
U/[V]L/[Rel. frame link guides.]U/[V]L/[Rel. frame link guides.]
Acid example4,197,584,406,95
4.1
Acid example 4,30to 7.674,517,02
4.2
Acid of EUR.as 4.026,294,434,75
example 2.1

Offer electroluminescent device with an injecting hole layer containing the composition according to the invention (examples 4.1 and 4.2), are more effective and have a significantly longer service life compared to an electroluminescent device containing an injecting hole layer made of a known material (PEDT:PSS from comparative example 4.3). After 100 hours long test at high current flowing through the device, the proposed device shows not only a smaller reduction in the intensity of electroluminescence, but also a smaller increase of the voltage.

1. The composition to obtain a hole-an injecting or hole-transporting layers in electroluminescent devices, organic solar elements is x batteries organic laser diodes, organic thin-film transistor or an organic field-effect transistors, or to obtain electrodes or conductive coatings containing polythiophene derivative, characterized in that the quality of the derived polythiophene it contains at least one polythiophene containing units of General formula (I)

in which
And means optionally substituted alkalinity balance with 1-5 carbon atoms, preferably optionally substituted ethylene or propylene residue,
R denotes a linear or branched alkyl residue with 1 to 18 carbon atoms, cycloalkenyl balance with 5-12 carbon atoms, an aryl residue with 6 to 14 carbon atoms, With7-C18-Aracely residue, a hydroxyalkyl residue with 1 to 4 carbon atoms or hydroxyl residue,
x means an integer from 0 to 8,
n means an integer from 2 to 100, and
if attached to a few residues R, these residues may be the same or different,
and additionally contains at least one containing SO3-M+or COO-M+group of the vinyl polymer in which M+denotes the N+Li+, Na+, K+, Rb+Cs+or NH4+preferably H+, Na+ or K+and at least one contains SO3-M+or COO-M+groups, partially or perforated vinyl polymer in which M+denotes the N+Li+, Na+, K+, Rb+Cs+or NH4+preferably H+, Na+or+,
moreover, the mass ratio of polythiophene to said polymer is from 1:2 to 1:25 and the said partially or perfluorinated polymer is from 1:1 to 1:50.

2. The composition according to claim 1, characterized in that polythiophene contains links of General formula (Ia)

in which
R and x have specified in claim 1 is, preferably x is 0 or 1.

3. The composition according to claim 1 or 2, characterized in that it contains as at least one containing SO3-M+or soo-M+-groups of the polymer polystyrenesulfonate.

4. The composition according to claim 1 or 2, characterized in that it contains as at least one containing SO3-M+or COO-M+group partially or perfluorinated polymer is a copolymer of tetrafluoroethylene and triftorbyenzola ether poly-(geksaftorpropilenom)-mono-(tetraferriphlogopite)-ether).

5. The composition according to claim 3, characterized in that it contains as at least one containing SO3 -M+or soo-M+group partially or perfluorinated polymer is a copolymer of tetrafluoroethylene and triftorbyenzola ether poly(HEXAFLUOROPROPYLENE oxide)-mono-(tetraferriphlogopite)-ether).

6. The composition according to claim 1 or 2, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+group partially or perfluorinated(th) polymer (polymers) is in the range from 1:2 to 1:30.

7. The composition according to claim 3, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+group partially or perfluorinated(th) polymer (polymers) is in the range from 1:2 to 1:30.

8. The composition according to claim 4, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+group partially or perfluorinated(th) polymer (polymers) is in the range from 1:2 to 1:30.

9. The composition according to claim 5, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+group partially or perfluorinated(th) polymer (polymers) is in the range from 1:2 to 1:30.

10. The composition according to claim 1 or 2, characterized in that the mass ratio of polythiophene (polythiophene) to contain the SO 3-M+or soo-M+-groups of the polymer (the polymer) is in the range from 1:2 to 1:20.

11. The composition according to claim 3, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+-groups of the polymer (the polymer) is in the range from 1:2 to 1:20.

12. The composition according to claim 4, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+-groups of the polymer (the polymer) is in the range from 1:2 to 1:20.

13. One of the subparagraph 5 and 7-9, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+-groups of the polymer (the polymer) is in the range from 1:2 to 1:20.

14. The composition according to claim 6, characterized in that the mass ratio of polythiophene (polythiophene) to contain SO3-M+or soo-M+-groups of the polymer (the polymer) is in the range from 1:2 to 1:20.

15. The composition according to claim 1 or 2, characterized in that it additionally contains at least one polar diluent.

16. The composition according to claim 3, characterized in that it additionally contains at least one polar diluent.

17. The composition according to claim 4, characterized in that it additionally contains at least one polar diluent.
18 the Composition according to demo of pp.5, 7-9, 11, 12, and 14, characterized in that it additionally contains at least one polar diluent.

19. The composition according to claim 6, characterized in that it additionally contains at least one polar diluent.

20. The composition according to claim 10, characterized in that it additionally contains at least one polar diluent.

21. The composition according to item 13, characterized in that it additionally contains at least one polar diluent.

22. The composition according to item 15, wherein the polar solvent is water, alcohol, in particular methanol, ethanol, n-propanol, 2-propanol or n-butanol or any mixture containing at least one of these diluents.

23. One of p, 17 and 19-21, characterized in that the polar solvent is water, alcohol, in particular methanol, ethanol, n-propanol, 2-propanol or n-butanol or any mixture containing at least one of these diluents.

24. The composition p, wherein the polar solvent is water, alcohol, in particular methanol, ethanol, n-propanol, 2-propanol or n-butanol or any mixture containing at least one of these diluents.

25. The electroluminescent device, in particular a led containing at least two electrodes, of which, optionally, at least one printed on, if you need the spine, transparent substrate, at least one emitter layer between the two electrodes and at least one hole-an injecting layer between one of the two electrodes and the emitter layer, wherein the hole-an injecting layer contains a composition according to one of claims 1 to 24.



 

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19 cl, 1 tbl, 2 dwg, 12 ex

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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.

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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.

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2 cl, 2 ex

FIELD: electric engineering.

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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

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