DE102008045662A1 - Optoelectronic device useful as white light emitting organic light-emitting diode in display, comprises first layer comprising electrode material, second layer comprising polymer material on substrate, and polymer layers having emitter - Google Patents

Abstract

The optoelectronic device useful as white light emitting organic light-emitting diode in a display, comprises a first layer comprising an electrode material, a second layer comprising a polymer material having fluorine-containing groups on a substrate, an additional layer, polymer layers having emitter function, electron blocking polymer layers having perforated conductors, hole blocking polymer layers with electron conductor function, a cathode and an encapsulation. The electrode material and polymer material of the first, second and additional layers have fluorine-containing groups. The optoelectronic device useful as white light emitting organic light-emitting diode in a display, comprises a first layer comprising an electrode material, a second layer comprising a polymer material having fluorine-containing groups on a substrate, an additional layer, polymer layers having emitter function, electron blocking polymer layers having perforated conductors, hole blocking polymer layers with electron conductor function, a cathode and an encapsulation. The electrode material and polymer material of the first, second and additional layers have fluorine-containing groups. An adhesive fluorine-fluorine interaction takes place between the parts of the fluorine-containing groups of the layers. The first and second layers comprise a conductive polymer. The second layer comprises a charge injection function, a charge transfer function and/or an emitter function. The additional layer comprises a polymer having fluorine-containing groups, a partly fluorinated polymer or a polymer with fluorinated perfluorinated side groups, oligomer with fluorinated groups or a fluorinated molecule. An adhesive fluorine-fluorine interaction is present between a part of the fluorine-containing groups of the additional layer and the respective preceding layer. The additional layer comprises a charge injection function, an emitter function and/or a barrier function. The polymer layers having the emitter function emit light of different wavelengths. The device adds the different optical wave lengths for white color and contains three layers having red, green and blue colors, where one of the layers contains singlet emitters, and other layers contain triplet emitters. The perforated conductors and the electron conductor comprise energetically different highest occupied molecule orbitals (HOMO) and a lowest unoccupied molecular orbital. Independent claims are included for: (1) a method for producing the optoelectronic device; and (2) a formulation containing fluorine-containing polymers, fluorine-containing blends and/or fluorinated small molecules in solvents.

Description

The The present invention relates to an optoelectronic device, comprising on a substrate a first layer and a second Layer, characterized in that the first layer is an electrode material with fluorine-containing groups and the second layer with a polymer comprising fluorine-containing groups, wherein between a part of the fluorine-containing Groups of the first layer and the second layer an adhesive fluorine-fluorine interaction consists. The invention further relates to the use of the optoelectronic Device and a method for producing the inventive optoelectronic device.

electronic Devices which are organic, organometallic and / or polymeric Semiconductors are becoming more common in commercial Products are used or are about to be launched. As examples, here are charge transport materials on organic Base (for example, triarylamine-based hole transporters) in Photocopiers and organic or polymeric light-emitting diodes (OLEDs or PLEDs) in display and display devices or organic Called photoreceptors in copiers. Organic solar cells (O-SC), organic field-effect transistors (O-FET), organic thin-film transistors (O-TFT), organic switching elements (O-IC), organic optical amplifiers and organic laser diodes (O-lasers) are in an advanced state Level of development and can be great in the future Gain meaning.

• (1) Substrat,
• (2) Elektrode, die häufig metallisch oder anorganisch, aber auch aus organischen bzw. polymeren leitfähigen Materialien aufgebaut sein kann,
• (3) gegebenenfalls eine oder mehrere Ladungsinjektionsschicht/en bzw. Zwischenschicht/en zum Ausgleich von Unebenheiten der Elektrode („planarisation layer”), die häufig aus einem oder mehreren leitfähigen, dotierten Polymer/en ausgebildet ist/sind,
• (4) mindestens eine Schicht eines organischen Halbleiters,
• (5) gegebenenfalls eine oder mehrere weitere Ladungstransport- bzw. Ladungsinjektions- bzw. Ladungsblockierschicht/en,
• (6) Gegenelektrode, bei der die unter (2) genannten Materialien eingesetzt werden,
• (7) Verkapselung.

Many of these electronic or opto-electronic devices, regardless of their intended use, have the following general layer structure, which can be adapted to the respective application:

• (1) substrate,
• (2) electrode, which can often be metallic or inorganic, but also composed of organic or polymeric conductive materials,
• (3) optionally one or more charge injection layer (s) to compensate for planarization layer (s) often formed of one or more conductive doped polymer (s),
• (4) at least one layer of an organic semiconductor,
• (5) optionally one or more further charge-transport or charge-blocking layer (s),
• (6) counterelectrode, in which the materials mentioned under (2) are used,
• (7) Encapsulation.

The present invention is particularly, but not exclusively, directed to organic light-emitting diodes (OLEDs), which are often referred to as polymeric light emitting diodes (PLED = Polymer Light Emitting Diode) when using polymeric materials. The above arrangement represents the general structure of an optoelectronic device, wherein different layers can be combined, so that in the simplest case there is an arrangement of two electrodes, between which an organic layer is located. The organic semiconductor layer in this case fulfills all functions, including the emission of light. Such a system is for example in the WO 9013148 A1 based on poly (p-phenylene) described.

One Problem that arises in such a "three-layer system", however, is the lack of control of charge separation or the lack of control Possibility to separate the individual components into different layers to optimize their properties, as for example in SMOLEDs ("small-molecule OLEDs") by a multilayered structure is simply solved. A "small For example, "molecule OLED" consists of one or more organic hole injection layers, hole transport layers, emission layers, Electron transport layers and electron injection layers as well an anode and a cathode, the whole system usually being located on a glass substrate. An advantage of such a multilayer structure is that different functions of charge injection, of charge transport and emission into the different layers divided and thus the properties of the respective layers can be modified separately.

typical Hole transport materials in SMOLEDs are, for example, di- and Triarylamines, thiophenes, furans or carbazoles, as well as in Photoconductor applications are studied and used.

metal chelates, conjugated aromatic hydrocarbons, oxadiazoles, imidazoles, Triazines, pyrimidines, pyrazines, pyridazines, phenanthrolines, ketones or phosphine oxides are usually used for the emission and Electron transport layers used in SMOLEDs.

The Compounds that are used in a SMOLED can often be cleaned by sublimations and stand thus in purities greater than 99 percent to Available.

The Application of the layers in SMOLED devices is usually done by vapor deposition in a vacuum chamber. This procedure is however consuming and therefore expensive and especially for large molecules, such as polymers, unsuitable.

polymers OLED materials are therefore usually by coating from solution applied. The production of a multilayer organic structure however, by coating from solution requires that Solvent incompatible with the previous layer is not to redeem them, to swell them or even to destroy. The choice of solvent proves However, it is difficult because of the organic compounds used usually similar properties, especially similar Solution properties, own. Already the application a first polymer layer on, for example, an indium-tin oxide layer usually already causes problems, since no sufficient liability of the Polymer layer can be ensured on the ITO. at an application of further layers of solution is the first polymer layer on the ITO again dissolved or even washed off and thereby destroyed.

Corresponding are conventional prior art polymeric OLEDs only from a single-layer or at most two-layered organic structure constructed, for example, one of the layers is used for hole injection and hole transport and the second layer for injection and transportation of electrons as well as for the emission is used.

Advantageous however, the polymeric OLEDs would also have a multilayer structure as with the SMOLEDs, with different approaches in the prior art were tried.

For example, the EP 0 637 899 A1 an electroluminescent device comprising one or more organic layers, wherein one or more of the layers are obtained by thermal or radiation-induced crosslinking. A problem with thermal crosslinking is that the polymeric layers are exposed to a relatively high temperature, which in part leads to the destruction of the corresponding layer or to the formation of undesired by-products. Crosslinking with actinic radiation often requires molecules or moieties which can initiate radical, cationic or anionic polymerization. However, it is known in the art that such molecules or molecular moieties may have negative effects on the function of an optoelectronic device. Also, the use of high-energy actinic radiation is problematic.

The Object of the present invention was therefore in the provision an optoelectronic device, one on a first Layer applied second layer does not dissolve again or destroyed.

The The object is achieved by an optoelectronic device, comprising on a substrate a first layer and a second Layer, characterized in that the first layer comprises an electrode material fluorine-containing groups and the second layer is a polymer containing fluorine Group comprises, wherein between a part of the fluorine-containing groups of first layer and the second layer, an adhesive fluorine-fluorine interaction consists.

In According to one embodiment of the invention it is preferred that the electrode is an indium tin oxide (ITO) layer or an indium zinc oxide layer (IZO) is. In this case, the second layer preferably comprises a conductive polymer.

In a further embodiment of the invention it is preferred that the electrode is a conductive polymer. In this Case, the second layer comprises a charge injection function (hole or electron), a charge transport function (hole or electron) and / or an emitter function.

In In all embodiments, the conductive polymer is preferably poly (3,4-ethylenedioxy-2,5-thiophene) (PEDOT) or polyaniline (PANI).

In a further preferred embodiment of the invention, the optoelectronic device comprises an additional layer (or several additional layers). Advantageously, the additional layer also comprises compounds with fluorine-containing groups. The additional layer may be a polymer having fluorinated groups, a partially fluorinated polymer or a polymer having fluorinated or perfluorinated side groups, an oligomer having fluorinated groups or a fluorinated molecule. As a result, between a part of the fluorine-containing groups of the components of the additional layer and the respective preceding layer there is an adhesive fluorine-fluorine interaction.

The additional layer is preferably a charge injection layer, an emitter layer, a barrier layer and / or a combination said.

In a further preferred embodiment of the invention it is preferred that the polymer of the further layer has an emitter function having. In particular, the polymer should emitter light emit different wavelengths. This can be done be achieved that in the layer different emitters in one or more polymers or a blend.

About that In addition, it is preferable that the device has multiple layers of polymers with emitter function. Particularly preferred doing that the multiple layers of polymers with emitter function each emit light of different wavelengths.

In a particularly preferred embodiment is further preferred that the different wavelengths for Add color white.

A preferred embodiment of the invention includes, for example a multilayer arrangement for a white light emitter, comprising an intermediate layer and a blue polymer layer which both adhere via F-F interactions, and a yellow triplet emitter, possibly also via F-F interactions can adhere. The yellow triplet emitter can be a real be a yellow emitter or an emitter, which is made of a red and green emitter. Through the use of stable triplet emitters with high efficiencies can be a white light emitting system with high efficiency and long life become. This system is also characterized by a simple manufacturing method (no Vacuum evaporation required) and thus lower costs.

In a still further embodiment of the invention can the device has several layers of polymers with hole conductor function include, wherein the hole conductors energetically different highest occupied molecular orbitals (HOMO).

there it is particularly preferred that the last applied polymer layer with hole conductor function an energetically high lowest unoccupied Molecular orbital (LUMO) has. That way is the last one applied polymer layer an electron blocking layer.

In a still further embodiment of the invention can the device comprises a plurality of layers of polymers having an electron conductor function, where the electronic conductors are highest in terms of energy occupied molecular orbitals (HOMO).

there it is particularly preferred that the polymer layer applied first with electron conductor function an energetically low lowest Unoccupied molecular orbital (LUMO). That way is the first-applied polymer layer has a hole-blocking layer.

A preferred embodiment thus comprises a multilayer arrangement, comprising a plurality of (partially) fluorinated polymeric hole conductors and / or Electron conductor (Interlayer) with different HOMO ("highest occupied molecular orbital ") and corresponding electron or hole blocking function. As a result, an improved hole or Electron injection due to graded barrier steps achieved become.

The Optoelectronic device according to the invention further comprises a cathode, and preferably an encapsulant.

• a) Aufbringen einer ersten Schicht auf ein Substrat, und
• b) Aufbringen einer zweiten Schicht,

wobei die erste Schicht eine Elektrode ist, welche vor, während oder nach dem Aufbringen auf das Substrat mit fluorhaltigen Gruppen versehen wird.The object according to the invention is also achieved by a method for producing an optoelectronic device, comprising

• a) applying a first layer to a substrate, and
• b) applying a second layer,

wherein the first layer is an electrode which is provided with fluorine-containing groups before, during or after application to the substrate.

In a preferred embodiment, the electrode used is indium tin oxide (ITO) or indium zinc oxide (IZO). In this case, the fluorine-containing groups are preferably applied to the electrode after application of the electrode to the substrate via surface reaction or CF ₄ plasma treatment.

In Another preferred embodiment is the electrode a conductive polymer and the fluorine-containing groups preferably before applying the electrode to the substrate in introduced the conductive polymer. Preferred is as conductive polymer used PEDOT or PANI, which is preferably provided with fluorine-containing groups.

For the second layer is preferably a partially fluorinated polymer, a polymer with perfluorinated side groups, an oligomer with fluorinated ones Used groups or a fluorinated molecule. Prefers is further that the second layer has a charge injection function, an emitter function, a barrier function or combinations of has mentioned functions.

On the applied layer is preferably one or more additional ones Layers applied. The additional layer (or the additional layers) preferably comprise a charge injection function (hole or electron injection function), an emitter function, a barrier function or combinations of said functions.

Prefers Furthermore, the application of a cathode and applying occur an encapsulation on the optoelectronic device.

"One Part "of the fluorine-containing groups means that about 1 to 100%, preferably 5 to 90% and particularly preferably 10 to 80% the fluorine-containing groups interact. It can, for example the distance of the fluorine atoms to interact with each other approximately equal to the van der Waals radius. At least is the distance of the fluorine atoms to each other so that an attractive F-F interaction occurs, comparable to the interaction at hydrogen bonds. Preferably comprises Polymer in a layer according to the invention 0.5 up to 100%, more preferably 1 to 50% and especially 1 to 25% fluorine - containing groups, related to the repeating units of the Polymer. 100% means that each repeat unit of the Polymers having fluorine-containing groups.

For the purposes of the present invention, the fluorine-containing groups R _f preferably have the general formula C _x H _y F _z , where x ≥ 0, y ≥ 0 and z ≥ 1 and none, one or more CH ₂ groups, which are also adjacent can be replaced by O, S, Se, Te, Si (R ¹ ) ₂ , Ge (R ¹ ) ₂ , NR ¹ , PR ¹ , CO, P (R ¹ ) O, where R ^{1 is} identical on each occurrence or different is a straight, branched or cyclic alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl or heteroalkyl group, wherein also one or more non-adjacent C atoms of the non-aromatic moieties O, S, CO, COO or OCO can be replaced, with the proviso that two radicals R ^{1 can} also form ring systems with one another. Preferred groups include, for example, F, CF ₃ , C ₂ F ₅ , CF ₃ (CH ₂ ) _a S, CF ₃ CF ₂ S or (CF ₃ - (CH ₂ ) _a ) ₂ N, where a is preferably an integer of 0 to 5 represents.

Surprisingly could be found that after applying a fluorinated Polymer or a polymer with fluorinated or perfluorinated Side groups from solution after removal of the solvent the polymer can no longer dissolve or wash off and does not swell. The layer could therefore without application of high temperatures and fixed without application of high-energy radiation become. Thus, easily another layer of solution be applied without the structure of the previous layer to harm. Surprisingly, it was also found that upon application of several fluorinated polymers (or fluorinated oligomers or fluorinated small molecules) adhesion due to fluorine-fluorine interaction of the layers caused among each other. The individual layers are applied by application further layers of solution not redissolved and do not swell either. In this way, polymeric, multilayer devices are provided as they are the "small molecule OLEDs" are known.

preferred Materials for the substrate are z. Glasses and films that have sufficient mechanical stability and barrier effect.

The first layer is preferably on the substrate, and usually serves as an electrode. For this purpose, the substrate may be coated, for example, electrically conductive. Indium tin oxide (ITO) or indium zinc oxide (IZO) is particularly preferably applied to the substrate, which is usually by vapor deposition happens. This is followed by fluorination.

Likewise, a conductive polymer can be applied to the substrate, for example by coating from solution. The conductive polymer is preferably selected from PEDOT and PANI. In a particularly preferred embodiment, the conductive polymer is a polymer which preferably carries fluorine-containing groups, for example fluorinated PEDOT or PANI. The polymer is preferably doped and can thus function as a charge injection layer. Preferably, the polymer is a polythiophene derivative, more preferably poly (3,4-ethylenedioxy-2,5-thiophene) (PEDOT) or polyaniline (PANI). The polymers are preferably doped with polystyrene sulfonic acid or other polymer-bound Brönsted acids and thus brought into a conductive state. According to the invention, the conductive polymer preferably contains fluorine-containing groups R _f (for example as defined above).

PEDOT is commercially available, for example from HC Stark. It is usually doped with polystyrenesulfonic acid as PEDOT: PSS. PEDOT is a conjugated polymer and can carry positive charges. Like PANI, it is a transparent polymer and is therefore excellently suited as a building block in an optoelectronic device. The incorporation of fluorine-containing groups in PEDOT is advantageously carried out in the preparation of the polymer, wherein fluorinated monomers can be used and copolymerized accordingly. It is also possible, as with PANI, to fluorinate an applied polymer layer, for example by means of CF ₄ plasma treatment.

polyaniline is a conjugated polymer which is oxidative and acid catalyzed mutually coupled aniline monomers. Polyaniline lies directly after the synthesis doped before (Emeraldine salt, ES). at the acid-catalyzed polymerization is the dopant the acid anion, in the basic environment is the base form (Emeraldine Base, EB). Undoped PANI appears blue, doped PANI green and the reduced forms yellowish. By doping by inserting or removing anions with different chemical-physical properties to set specific modifications.

In order to obtain a polyaniline having fluorine-containing groups according to the present invention, aniline may be copolymerized together with aniline derivatives, e.g. B. by Anilinmonomere having substituents with fluorine-containing radicals R _f (for example, as defined above), z. For example, 2-trifluoromethyl-aniline or similar compounds.

If the first layer is an ITO or an IZO layer in the second layer is preferably a conductive polymer. It is also possible that the second layer of the conductive polymer itself.

It it is further preferred that the second layer has a hole injection function and furthermore it is preferred that the second layer a hole transport function. Both functions can for example by doped polythiophene derivatives or polyanilines to be provided.

As well For the purposes of this invention, the second layer may be a preferred one Emitter function include. This can be done, for example, by copolymerization of emitter compounds or photoluminescent compounds with the monomers of the corresponding (conductive) polymer respectively. The emitter compounds or photoluminescent compounds may be in the main chain or the side chain of the conductive polymer or can be, for example grafted in appropriate places. Likewise, monomeric or polymeric emitter compounds are used, which are preferably have fluorine-containing groups.

Preferably comprises the optoelectronic invention Device an additional layer. Likewise preferred is that in addition to the one additional layer even more additional layers are present in the device. For the purposes of this invention, it is preferred that the additional Layer (or additional layers) compounds with fluorine-containing groups, preferably as defined above. Consequently The at least one additional layer can also be a polymer with fluorine-containing groups, a partially fluorinated polymer or a polymer having fluorinated or perfluorinated pendant groups Oligomer with fluorinated groups or a fluorinated molecule be (small molecule).

According to the invention, the optoelectronic device is characterized in that an adhesive fluorine-fluorine interaction exists between a part of the fluorine-containing groups of the additional layer and the respective preceding layer. For the purposes of this invention, the additional layer may comprise a charge injection layer (hole or electron injection layer), a charge transport layer (hole or electron transfer layer) Electron transport layer), an emitter layer, a hole or electron blocking layer, and / or a combination of the foregoing. This in turn means that the additional layer can combine several functions in one layer, or that several additional layers assume the corresponding functions.

• 1) Substrat,
• 2) Elektrode bzw. Anode,
• 3) Lochinjektionsschicht/en,
• 4) Lochtransportschicht/en,
• 5) Emissionsschicht/en
• 6) Elektronentransportschicht/en
• 7) Elektroneninjektionsschicht/en und
• 8) Gegenelektrode bzw. Kathode.

As a result, according to the invention, a classical structure consisting of substrate, electrode, multifunctional layer and cathode or a structure as in the case of a "small molecule OLED" is possible, namely a construction

• 1) substrate,
• 2) electrode or anode,
• 3) hole injection layer (s),
• 4) hole transport layer (s),
• 5) emission layer (s)
• 6) Electron transport layer (s)
• 7) electron injection layer (s) and
• 8) counter electrode or cathode.

According to the invention one or more of the layers are combined with each other or It can be made up of polymeric layers with layers, like them from a SMOLED are combined.

For example Components can be vapor-deposited or printed if desired, or it can be components be applied from solution, wherein the components are preferred have fluorine-containing groups.

On This way you can make devices with thicker layers be provided, these layers, for example, as Hole injection layers or electron barrier layers act can. Such layers can be easily related their color and effectiveness are optimized. About that In addition, the life of such a layer is improved Electron blocking feature increases (less tunneling effects in the underlying layer, especially in PEDOT).

The optoelectronic device according to the present invention is suitable as an organic or polymeric light-emitting diode, as an organic solar cell (O-SC, eg. WO 98/48433 . WO 94/05045 ), as an organic field-effect transistor (O-FETs), as an organic switching element (O-IC, eg. WO 95/31833 . WO 99/10939 ), as an organic field quench element (FDQ, eg. US 2004/017148 ), as an organic optical amplifier, as an organic photoreceptor, as an organic photodiode or as an organic laser diode (O-LASER, eg. WO 98/03566 ) and can be used accordingly.

For The use in O-FETs are mainly materials with high charge carrier mobility of interest. These are, for example, oligo- or poly (triarylamines), Oligo- or poly (thiophene) and copolymers containing a high proportion contain these units.

The Device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since itself the life of such devices in the presence of water and / or air drastically shortened. It may also be preferred be as electrode material for one or both of the electrodes to use a conductive, doped polymer and none Intermediate layer of conductive, doped polymer to bring.

For Applications in O-FETs and O-TFTs also require that the structure except electrode and counter electrode (source and drain) contains yet another electrode (gate), which by an insulator layer with a generally high (or rarely low) dielectric constant of the organic Semiconductor is separated. Besides, it may make sense to bring in the device even more layers.

The Electrodes are chosen in the sense of this invention that their potential as well as possible with the potential of adjacent organic layer matches to a the most efficient electron or hole injection possible guarantee.

As the cathode, low work function metals, metal alloys or multilayer structures of various metals are preferable, such as alkaline earth metals, alkali metals, main group metals or lathanoids (eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). , In multilayer structures, it is also possible, in addition to the metals mentioned, to use further metals which have a relatively high work function have, such. B. Ag, which then usually combinations of metals, such as Ca / Ag or Ba / Ag are used. It may also be preferred to introduce between a metallic cathode and the organic semiconductor a thin intermediate layer of a material with a high dielectric constant. Suitable examples of this are, for example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides (for example LiF, Li ₂ O, BaF ₂ , MgO, NaF, etc.). The layer thickness of this layer is preferably between 1 and 10 nm.

As the anode, high workfunction materials are preferred. Preferably, the anode has a potential greater than 4.5 eV. Vacuum up. On the one hand, metals with a high redox potential, such as Ag, Pt or Au, are suitable for this purpose. On the other hand, metal / metal oxide electrons (for example Al / Ni / NiO _x , Al / PtO _x ) may also be preferred. For some applications, at least one of the electrodes must be transparent to allow either the irradiation of the organic material (O-SC) or the outcoupling of light (OLED / PLED, O-LASER). A preferred construction uses a transparent anode. Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO), which have fluorine-containing groups. Preference is furthermore given to conductive, doped organic materials, in particular conductive doped polymers, which preferably have fluorine-containing groups, as defined above.

As hole injection layer on the anode, various doped, conductive polymers come into question. Preference is given to polymers which, depending on the application, have a conductivity> 10 ^-8 S / cm. The potential of the layer is preferably 4 to 6 eV. Vacuum. The layer thickness is preferably between 10 and 500 nm, more preferably between 20 and 250 nm. Particular preference is given to using derivatives of polythiophene (in particular poly (3,4-ethylenedioxy-2,5-thiophene) (PEDOT) and polyaniline (PANI). Other preferred (intrinsic) conductive polymers are polythiophene (PTh), poly (3,4-ethylenedioxythiophene) (PEDOT), polydiacetylene, polyacetylene (PAc), polypyrrole (PPy), polyisothianaphthene (PITN), polyheteroarylenevinylene (PArV), the heteroarylene Group may be, for example, thiophene, furan or pyrrole, poly-p-phenylene (PpP), polyphenylene sulfide (PPS), polyperinaphthalene (PPN), polyphthalocyanine (PPc), etc., as well as their derivatives (which, for example, with Side-chains or groups of substituted monomers are formed), their copolymers and their physical mixtures The doping is generally carried out by acids or by oxidants Preferably, the doping is carried out by polymer-bound Brönsted acids polymer-bound sulfonic acids, in particular poly (styrenesulfonic acid), poly (vinylsulfonic acid). Preferably, the conductive polymer for the charge injection layer has fluorine-containing groups, whereby after application from solution and removal of the solvent, the layer is fixed by adhesive FF interactions.

Prefers the polymer contains the emitter layer next to emitting Repeat units more repeat units, also preferably have fluorine-containing groups or substituents. It can this is a single polymeric compound or a blend of two or more polymeric compounds or a blend of one or more polymeric compounds having one or more low molecular weight act organic compounds. The organic emitter layer may preferably be by coating from solution or by various printing methods, in particular by ink-jet printing method be applied. The polymeric compound and / or the others Compounds preferably have fluorine-containing groups. The layer thickness of the organic semiconductor is preferably 10, depending on the application up to 500 nm, more preferably 20 to 250 nm.

Preferred repeating units in the polymer of the emitter layer include, but are not limited to, for example, the compounds shown below:

Here, Rf is a fluorinated radical of the general formula C _x H _y F _z , where x ≥ 0, y ≥ 0 and z ≥ 1 and none, one or more CH ₂ groups, which may also be adjacent, by O, S , Se, Te, Si (R ¹ ) ₂ , Ge (R ¹ ) ₂ , NR ¹ , PR ¹ , CO, P (R ¹ ) O may be replaced, where R ^{1 is the} same or different and is a straight-chain, branched one or cyclic alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl or heteroalkyl group, whereby also one or more nonadjacent carbon atoms of the non-aromatic moieties are represented by O, S, CO, COO or OCO can be replaced, with the proviso that two radicals R ^{1 can} also form ring systems with one another. Preferred groups include, for example, F, CF ₃ , C ₂ F ₅ , CF ₃ (CH ₂ ) _a S, CF ₃ CF ₂ S or (CF ₃ - (CH ₂ ) _a ) ₂ N, where a is preferably an integer of 0 to 5 represents.

For the purposes of this invention, preferred polymers or fluorine-containing polymers (or polymers having fluorinated or perfluorinated side groups) are conjugated polymers or partially conjugated polymers which contain sp ² -hybridized carbon atoms in the main chain which may also be replaced by corresponding heteroatoms. Furthermore, for the purposes of this invention, conjugate is also referred to when in the main chain, for example, arylamine units and / or certain heterocycles (ie conjugation via N, O or S atoms) and / or organometallic complexes (ie conjugation via the metal atom) are located. Typical representatives of conjugated polymers, as used for example in PLEDs or generally in O-SCs Polypara-phenylenevinylenes (PPV), polyfluorenes, polyspirobifluorenes, polyphenanthrene, polydihydrophenanthrenes, polyindenofluorenes, systems which are broadly based on poly-p-phenylenes (PPP), and derivatives of these structures, especially those derivatives, are the fluorine-containing groups exhibit.

Particular preference is given according to the invention to those polymers which contain further structural elements and are thus to be referred to as copolymers. Here is above all on the relatively extensive lists of possible structural elements in the WO 02/077060 , of the WO 2005/014689 and referenced the citations listed in these references. These further structural units can come, for example, from the classes described below: Group 1: Structural units representing the polymer backbone. Group 2: Structural units which increase the hole injection and / or transport properties of the polymers. Group 3: Structural units which increase the electron injection and / or transport properties of the polymers. Group 4: Structural units comprising combinations of single units of group 2 and group 3. Group 5: Structural units which influence the morphology and / or the emission color of the resulting polymers. Group 6: Structural units which change the emission characteristics to the extent that electrophosphorescence can be obtained instead of electrofluorescence. Group 7: Structural units that improve the transition from singlet to triplet state.

suitable and preferred units for the above groups are described below, these preferably according to the invention defined have fluorine-containing groups.

Group 1 - Structural units, which represent the polymer backbone:

Preferred group 1 units are, in particular, those which contain aromatic or carbocyclic structures having 6 to 40 C atoms. Suitable and preferred units include fluorene derivatives, such as. B. in the EP 0842208 , of the WO 99/54385 , of the WO 00/22027 , of the WO 00/22026 and the WO 00/46321 discloses indenofluorenes, further spirobifluorene derivatives such. B. in the EP 0707020 , of the EP 0894107 and the WO 03/020790 discloses phenanthrene derivatives or dihydrophenanthrene derivatives, such as. B. in the WO 2005/014689 disclosed. It is also possible to use a combination of two or more of these monomer units, such as. B. in the WO 02/077060 described. Preferred units for the polymer backbone are, in addition to the units of the formula (1), in particular spirobifluorene, indenofluorene, phenanthrene and dihydrophenanthrene derivatives.

worin die einzelnen Reste folgende Bedeutung besitzen:
YY ist Si oder Ge,
VV ist O, S oder Se,
und wobei die verschiedenen Formeln an den freien Positionen auch zusätzlich durch einen oder mehrere Substituenten R² substituiert sein können und R² folgendes bedeuten:
R² ist bei jedem Auftreten gleich oder verschieden H, eine geradkettige, verzweigte oder cyclische Alkyl- oder Alkoxykette mit 1 bis 22 C-Atomen, in der auch ein oder mehrere nicht benachbarte C-Atome durch O, S, CO, O-CC, CO-O oder O-CO-O ersetzt sein können, wobei auch ein oder mehrere H-Atome durch Fluor ersetzt sein können, eine Aryl- oder Aryloxygruppe mit 5 bis 40 C-Atomen, bei der auch ein oder mehrere C-Atome durch O, S oder N ersetzt sein können, welche auch durch ein oder mehrere nicht-aromatische Reste R² substituiert sein können, oder F, CN, N(R³)₂ oder B(R³)₂; und
R³ ist bei jedem Auftreten gleich oder verschieden H, eine geradkettige, verzweigte oder cyclische Alkylkette mit 1 bis 22 C-Atomen, in der auch ein oder mehrere nicht benachbarte C-Atome durch O, S, CO, O-CC, CO-O oder O-CO-O ersetzt sein können, wobei auch ein oder mehrere H-Atome durch Fluor ersetzt sein können, oder eine optional substituierte Arylgruppe mit 5 bis 40 C-Atomen, bei der auch ein oder mehrere C-Atome durch O, S oder N ersetzt sein können.Particularly preferred units of group 1 are divalent units according to the following formulas, wherein the dotted lines represent the linkages to the adjacent units:

in which the individual radicals have the following meaning:
YY is Si or Ge,
VV is O, S or Se,
and wherein the different formulas at the free positions may additionally be substituted by one or more substituents R ² and R ^{2 is the} following:
R ² is the same or different at each occurrence H, a straight-chain, branched or cyclic alkyl or alkoxy chain having 1 to 22 carbon atoms, in which also one or more non-adjacent C atoms by O, S, CO, O-CC , CO-O or O-CO-O may be replaced, wherein one or more H atoms may be replaced by fluorine, an aryl or aryloxy group having 5 to 40 carbon atoms, in which also one or more C atoms may be replaced by O, S or N, which may also be substituted by one or more non-aromatic radicals R ² , or F, CN, N (R ³ ) ₂ or B (R ³ ) ₂ ; and
R ³ is the same or different H, a straight-chain, branched or cyclic alkyl chain having 1 to 22 C atoms in each occurrence, in which also one or more nonadjacent C atoms are represented by O, S, CO, O-CC, CO- O or O-CO-O may be replaced, it also being possible for one or more H atoms to be replaced by fluorine, or an optionally substituted aryl group having 5 to 40 C atoms, in which one or more C atoms are also replaced by O, S or N can be replaced.

Group 2 - structural units, which the Lochinjektions- and / or -transporteigenschaften the Increase polymers:

These are generally aromatic amines or electron-rich heterocycles, such as. Substituted or unsubstituted triarylamines, benzidines, tetraarylene-para-phenylenediamines, phenothiazines, phenoxazines, dihydrophenazines, thianthrenes, dibenzo-p-dioxins, phenoxathiines, carbazoles, azulene, thiophenes, Pyrroles, furans, and other O, S, or N-containing heterocycles with high HOMO (HOMO = highest occupied molecular orbital). But there are also triarylphosphines in question, such as. B. in the WO 2005/017065 A1 described.

wobei R¹¹ eine der oben für R² angegebenen Bedeutungen besitzt, die verschiedenen Formeln an den freien Positionen auch zusätzlich durch einen oder mehrere Substituenten R¹¹ substituiert sein können und die Symbole und Indices folgendes bedeuten:
n ist gleich oder verschieden bei jedem Auftreten 0, 1 oder 2,
p ist gleich oder verschieden bei jedem Auftreten 0, 1 oder 2, vorzugsweise 0 oder 1,
o ist gleich oder verschieden bei jedem Auftreten 1, 2 oder 3, vorzugsweise 1 oder 2,
Ar¹¹, Ar¹³ sind bei jedem Auftreten gleich oder verschieden ein aromatisches oder heteroaromatisches Ringsystem mit 2 bis 40 C-Atomen, welches durch R¹¹ ein- oder mehrfach substituiert oder auch unsubstituiert sein kann; die möglichen Substituenten R¹¹ können dabei potentiell an jeder freien Position sitzen,
Ar¹², Ar¹⁴ sind bei jedem Auftreten gleich oder verschieden Ar¹¹, Ar¹³ oder eine substituierte oder unsubstituierte Stilbenylen- bzw. Tolanyleneinheit,
Ar¹⁵ ist gleich oder verschieden bei jedem Auftreten entweder ein System gemäß Ar¹¹ oder ein aromatisches oder heteroaromatisches Ringsystem mit 9 bis 40 aromatischen Atomen (C- oder Heteroatome), welches durch R¹¹ ein- oder mehrfach substituiert oder unsubstituiert sein kann und welches aus mindestens zwei kondensierten Ringen besteht; die möglichen Substituenten R¹¹ können dabei potentiell an jeder freien Position sitzen.Particularly preferred group 2 units are divalent units according to the following formulas, wherein the dotted lines represent the linkages to the adjacent units:

where R ^{11 has} one of the meanings given above for R ² , the various formulas at the free positions may also be additionally substituted by one or more substituents R ¹¹ and the symbols and indices mean:
n is the same or different at every occurrence 0, 1 or 2,
p is identical or different at each occurrence 0, 1 or 2, preferably 0 or 1,
o is identical or different at each occurrence 1, 2 or 3, preferably 1 or 2,
Ar ¹¹ , Ar ¹³ are the same or different at each occurrence and an aromatic or heteroaromatic ring system having 2 to 40 carbon atoms, which may be monosubstituted or polysubstituted by R ¹¹ or may also be unsubstituted; the possible substituents R ¹¹ can potentially be located at any free position,
Ar ¹² , Ar ¹⁴ are the same or different on each occurrence Ar ¹¹ , Ar ¹³ or a substituted or unsubstituted stilbenylene or tolanylene unit,
Ar ¹⁵ is identical or different at each occurrence either a system according to Ar ¹¹ or an aromatic or heteroaromatic ring system having 9 to 40 aromatic atoms (C or heteroatoms), which may be monosubstituted or polysubstituted by R ¹¹ or unsubstituted and which at least two condensed rings; the possible substituents R ¹¹ can potentially sit at any free position.

Group 3 - Structural units, which the electron injection and / or transport properties increase the polymers:

These are generally electron-deficient aromatics or heterocycles, such as. As substituted or unsubstituted pyridines, pyrimidines, pyridazines, pyrazines, pyrenes, perylenes, anthracenes, Benzanthracene, oxadiazoles, quinolines, quinoxalines, phenazines, benzimidazoles, ketones, phosphine oxides, sulfoxides or triazines, but also compounds such as triarylboranes and other O, S or N-containing heterocycles with low lying LUMO (LUMO = lowest unoccupied molecular orbital), as well as benzophenones and their derivatives, such as. B. in the WO 05/040302 disclosed.

wobei die verschiedenen Formeln an den freien Positionen durch einen oder mehrere Substituenten R¹¹ wie oben definiert substituiert sein können.Particularly preferred group 3 units are divalent units according to the following formulas, wherein the dotted lines represent the linkages to the adjacent units:

wherein the different formulas may be substituted at the free positions by one or more substituents R ¹¹ as defined above.

Group 4 - Structural units, the combinations of individual units of group 2 and group 3 exhibit:

It it is also possible that the polymers contain units, in which structures which the hole mobility and which increase electron mobility, directly to each other are bound or both can. However, move some of these units have the emission color in yellow or red. Their use in the optoelectronic invention Device for generating blue or green emission is therefore less preferred.

wobei die verschiedenen Formeln an den freien Positionen durch einen oder mehrere Substituenten R¹¹ substituiert sein können, die Symbole R¹¹, Ar¹¹, p und o die oben genannten Bedeutungen besitzen und Y bei jedem Auftreten gleich oder verschieden O, S, Se, N, P, Si oder Ge ist.If such Group 4 units are included in the polymers, they are preferably selected from divalent units according to the following formulas, wherein the dotted lines represent the linkages to the adjacent units:

wherein the different formulas may be substituted at the free positions by one or more substituents R ¹¹ , the symbols R ¹¹ , Ar ¹¹ , p and o have the abovementioned meanings and Y on each occurrence identically or differently O, S, Se, N , P, Si or Ge is.

Group 5 - structural units, which the morphology and / or the emission color of the resulting Polymers influence:

In addition to the abovementioned units, these are those which have at least one further aromatic or another conjugated structure which does not fall under the abovementioned groups, ie which only slightly influences the charge carrier mobility, which are not organometallic complexes or which have no influence on the singlet -Triplett transition have. Such structural elements can influence the morphology, but also the emission color of the resulting polymers. Depending on the unit, they can therefore also be used as emitters. Preference is given to substituted or unsubstituted aromatic structures having 6 to 40 carbon atoms or tolan, stilbene or Bisstyrylarylenderivate, each of which may be substituted with one or more radicals R ¹¹ . Particularly preferred is the incorporation of 1,4-phenylene, 1,4-naphthylene, 1,4- or 9,10-anthrylene, 1,6-, 2,7- or 4,9-pyrenylene, 3,9- or 3,10-perylenylene, 4,4'-biphenylylene, 4,4 "-terphenylylene, 4,4'-bi-1,1'-naphthylylene, 4,4'-tolanylene , 4,4'-stilbenylene or 4,4 "-bis-styrylarylene derivatives.

wobei die verschiedenen Formeln an den freien Positionen durch einen oder mehrere Substituenten R¹¹ wie oben definiert substituiert sein können.Very particular preference is given to substituted or unsubstituted structures according to the following formulas, in which the dashed lines denote the linkages to the adjacent units:

wherein the different formulas may be substituted at the free positions by one or more substituents R ¹¹ as defined above.

Group 6 - structural units, which change the emission characteristics insofar that electrophosphorescence is obtained instead of electrofluorescence can:

These are in particular those units which can emit light from the triplet state even at room temperature with high efficiency, ie exhibit electrophosphorescence instead of electrofluorescence, which frequently causes an increase in energy efficiency. Compounds which contain heavy atoms with an atomic number of more than 36 are suitable for this purpose. Especially suitable are compounds containing d- or f-transition metals that meet the above condition. Very particular preference is given to corresponding structural units which contain elements of group 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt). As structural units for the polymers come here z. B. various complexes in question, which z. B. in the WO 02/068435 , of the WO 02/081488 , of the EP 1239526 and the WO 04/026886 are described. Corresponding monomers are in the WO 02/068435 and the WO 2005/042548 A1 described.

worin M für Rh oder Ir steht, Y die oben angegebene Bedeutung hat, und die verschiedenen Formeln an den freien Positionen durch eine oder mehrere Substituenten R¹¹ wie oben definiert substituiert sein können.Preferred group 6 units are those of the following formulas wherein the dashed lines represent the linkages to the adjacent units:

wherein M is Rh or Ir, Y is as defined above, and the various formulas at the free positions may be substituted by one or more substituents R ¹¹ as defined above.

Group 7 - structural units, which transition from singlet to triplet state improve:

These are in particular those units which improve the transition from singlet to triplet state and which, used in support of the structural elements of group 6, the phosphores Improve zenzeigenschaften these structural elements. For this purpose, in particular carbazole and bridged carbazole dimer units in question, such as. B. in the WO 04/070772 and the WO 04/113468 described. Furthermore, this come ketones, phosphine oxides, sulfoxides and similar compounds in question, such as. B. in the WO 2005/040302 A1 described.

It is also possible that at the same time more than one structural unit from one of the groups 1 to 7 is present.

The Polymer can also continue in the main or side chain contain bound metal complexes, which are generally composed of a or more ligands and one or more metal centers are.

Prefers are polymers that additionally contain one or more units selected from Groups 1 to 7.

Also it is preferred if the polymers contain units which contain the Improve charge transport or charge injection, ie units from group 2 and / or 3; a proportion of 1 is particularly preferred to 30 mol% of these units; very particular preference is given to a proportion from 2 to 10 mol% of these units.

Especially It is furthermore preferred if the polymers are units from group 1, units from group 2 and / or 3 and units from group 5 contain.

The Polymers preferably have 10 to 10,000, more preferably 20 to 5000 and especially 50 to 2000 repeat units. To distinguish this are the inventive fluorinated oligomers having 3 to 9 repeating units. Otherwise, the oligomers can all be defined above Repeating units, including the emitter possess.

The necessary solubility of the polymers becomes especially by the substituents on the different repeat units guaranteed.

The polymers can be linear, branched or crosslinked. The copolymers according to the invention may have random, alternating or block-like structures or alternatively have several of these structures in turn. How copolymers with block-like structures can be obtained and which further structural elements are particularly preferred for this purpose is described in detail in US Pat WO 2005/014688 described. This font is via quote part of the present application.

The Polymers are usually produced by polymerization of one or more polymers produced several monomer types. Suitable polymerization reactions are known in the art and described in the literature. Especially suitable and preferred polymerization and coupling reactions, which all lead to C-C joins are those according to SUZUKI, YAMAMOTO, SILENCE, TAIL, NEGISHI, SONOGASHIRA or HIYAMA.

How the polymerization can be carried out by these methods and how the polymers can then be separated off from the reaction medium and purified is known to the person skilled in the art and is described in the literature, for example in US Pat WO 2003/048225 and the WO 2004/037887 , described in detail.

The C-C linkages are preferably selected from the groups of the SUZUKI coupling, the YAMAMOTO coupling and the STILLE coupling.

The synthesis of the polymers requires the corresponding monomers. The synthesis of units from groups 1 to 7 is known in the art and in the literature, for example in the WO 2005/014689 , described. This and the literature cited therein is incorporated by reference in the present application.

It may also be preferred, the polymer is not as a pure substance, but as a mixture (misery) along with any other polymers, to use oligomeric, dendritic or low molecular weight substances. These can be, for example, the electronic properties improve or emit yourself. Such misery is therefore too Component of the present invention.

The invention further provides solutions and formulations of one or more flu containing polymers and / or fluorine-containing blends and / or fluorinated small molecules according to the invention (as defined above) in one or more solvents. How polymer solutions or solutions of small molecules can be prepared is known to the skilled person and z. B. in the WO 02/072714 , of the WO 03/019694 and the literature cited therein. The solutions and formulations may optionally contain one or more additives.

These Solutions can be used to thin Polymer layers, for example by surface coating method (eg spin-coating) or by printing processes (eg inkjet printing), in particular in the method according to the invention.

• a) Aufbringen einer ersten Schicht auf ein Substrat, und
• b) Aufbringen einer zweiten Schicht,

wobei die erste Schicht eine Elektrode ist, welche vor, während oder nach Aufbringung auf das Substrat mit fluorhaltigen Gruppen versehen wird.The invention also provides a method for producing an optoelectronic device, comprising

• a) applying a first layer to a substrate, and
• b) applying a second layer,

wherein the first layer is an electrode which is provided with fluorine-containing groups before, during or after application to the substrate.

In a preferred embodiment, the electrode used is indium tin oxide (ITO) or indium zinc oxide (IZO). In this case, after applying the electrode to the substrate, the fluorine-containing groups are applied to the electrode via surface reaction or CF ₄ plasma treatment. As a result, different fluorine-containing groups are formed on the surface of the electrode, for example CF ₃ or even individual fluorine atoms which combine with the substrate.

When Substrate according to the invention glass or a polymer film used, preferred is glass.

In Another preferred embodiment is the electrode a conductive polymer and the fluorine-containing groups before applying the electrode to the substrate in the conductive Polymer introduced. Preference is given as a conductive polymer one of the conjugated polymers defined above, PEDOT or PANI used, which are preferably provided with fluorine-containing groups. In a conductive polymer, the fluorination is carried out by Methods of the prior art, for example by fluorinated Monomers are polymerized or fluorinated by the finished polymer becomes. Preferred is a component containing fluorine-containing groups a partially fluorinated polymer or a fluorinated polymer or perfluorinated side groups, an oligomer with fluorinated ones Groups, a fluorinated molecule, or combinations thereof, used.

The second layer is preferred by coating one of the polymer containing solution, for example by spin coating or rackets applied. For the second layer is a partially fluorinated polymer, a polymer with perfluorinated side groups, an oligomer with fluorinated groups or a fluorinated molecule used. It is further preferred that the second layer has a charge injection function, an emitter function, a barrier function or combinations of has mentioned functions. This can, for example, a top defined conjugated polymer are used, which is the has corresponding functions, or it may be appropriate Oligomers or molecules are used. Likewise the emitters defined above in the invention Procedures are used.

On the applied layer can now have one or more additional layers Layers are applied without the fixed layer being dissolved is or swells. The fluorine-containing groups of the previous layer and direct the fluorine-containing groups of the applied layer It is assumed that an adhesive fluorine-fluorine interaction occurs, which after removal of the solvent a Adhesion of the applied layer on the previous one Guaranteed layer equivalent to the effect of a crosslinking reaction.

On This way, you can also make thicker layers which are used, for example, as hole injection layers or electron barrier layers act and these layers can respect Color and effectiveness are optimized. About that In addition, the life of such a layer by an improved Electron blocking function can be increased (less tunneling effects in the underlying layer, especially in PEDOT the case).

Further, after all additional layers have been applied sequentially, the application of a cathode is followed by methods known in the art. Finally follows the application of a Verkapse ment to protect the device from external influences such as water vapor, oxygen and the like.

The The invention will now not be limited by some Embodiments to be considered for the scope of the invention explained in more detail with reference to the figures become.

EXAMPLES

Example 1:

1 shows a device according to the invention, in which a fluorinated ITO is coated with a fluorinated polymer. The fluorine atoms come so close that an adhesive FF interaction exists.

The Device was obtained by evaporating an ITO onto a glass substrate, which then via a CF4 plasma treatment was fluorinated. On the fluorinated ITO layer was a fluorinated PEDOT applied from solution by spin coating and the Solvent removed in vacuo. After removing the Solvent left a layer of fluorinated PEDOT on the fluorinated ITO layer, resulting in treatment can not be solved again with solvents and not too much.

Example 2:

2 shows a device according to the invention, in which the device coated from Example 1 is coated with another layer of a fluorinated polymer via spin coating. Again, after removal of the solvent in vacuo via an adhesive FF interaction, a fixation of the layers is achieved. The underlying layer was neither dissolved nor swollen during the spin-coating process.

QUOTES INCLUDE IN THE DESCRIPTION

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

Cited patent literature

• - WO 9013148 A1 [0004]
• - EP 0637899 A1 [0013]
• WO 98/48433 [0055]
• WO 94/05045 [0055]
• WO 95/31833 [0055]
• WO 99/10939 [0055]
• US 2004/017148 [0055]
• WO 98/03566 [0055]
• WO 02/077060 [0067, 0069]
• WO 2005/014689 [0067, 0069, 0093]
• - EP 0842208 [0069]
• WO 99/54385 [0069]
• WO 00/22027 [0069]
• WO 00/22026 [0069]
• WO 00/46321 [0069]
• EP 0707020 [0069]
• - EP 0894107 [0069]
• WO 03/020790 [0069]
• WO 2005/017065 A1 [0071]
• WO 05/040302 [0073]
• WO 02/068435 [0079, 0079]
• WO 02/081488 [0079]
• - EP 1239526 [0079]
• WO 04/026886 [0079]
• WO 2005/042548 A1 [0079]
• WO 04/070772 [0081]
• WO 04/113468 [0081]
• WO 2005/040302 A1 [0081]
• WO 2005/014688 [0089]
• WO 2003/048225 [0091]
• WO 2004/037887 [0091]
• WO 02/072714 [0095]
• WO 03/019694 [0095]

Claims (34)

An optoelectronic device comprising on a substrate a first layer and a second layer, characterized in that the first layer comprises an electrode material having fluorine-containing groups and the second layer comprises a polymer having fluorine-containing groups, wherein between a part of the fluorine-containing groups of the first layer and the second Layer consists of an adhesive fluorine-fluorine interaction. Optolektronische device according to claim 1, characterized in that the first layer is an indium tin oxide layer (ITO) or an indium-zinc oxide layer (IZO). Optoelectronic device according to claim 1 or 2, characterized in that the second layer is a conductive Polymer includes. Optolektronische device according to claim 1, characterized characterized in that the first layer is a conductive layer Polymer is. Optoelectronic device according to claim 3 or 4, characterized in that the conductive polymer PEDOT or PANI is. Optoelectronic device according to one or more of claims 1 to 5, characterized in that the second layer, a charge injection function, a charge transport function and / or an emitter function. Optoelectronic device according to one of the claims 1 to 6, comprising at least one additional layer. Optoelectronic device according to claim 7, characterized in that that the additional layer compounds containing fluorine Includes groups. Optoelectronic device according to claim 7 or 8, characterized in that the additional layer a polymer with fluorine-containing groups, a partially fluorinated one Polymer or a polymer with fluorinated or perfluorinated side groups, an oligomer with fluorinated groups or a fluorinated molecule includes. Optoelectronic device according to one of the claims 8 or 9, characterized in that between a part of the fluorine-containing Groups of the additional layer and the respective preceding layer an adhesive fluorine-fluorine interaction exists. Optoelectronic device according to one of the claims 8 to 10, characterized in that the additional Layer a charge injection function, an emitter function, a Barrier function and / or a combination of the said. Optoelectronic device according to one or more of claims 1 to 11, characterized in that the Device has a polymer with emitter function. Optoelectronic device according to claim 12, characterized in that the polymer with emitter function light emitted different wavelengths. Optoelectronic device according to one of the claims 1 to 11, characterized in that the device comprises a plurality of layers of polymers with emitter function. Optoelectronic device according to claim 14, characterized in that the plurality of layers of polymers each with emitter function light of different wavelengths emit. Optoelectronic device according to claim 13 or 15, characterized in that the different wavelengths of light add to the color white. Optoelectronic device according to one or more of claims 1 to 16, characterized in that the Device several layers of polymers with hole conductor function includes, wherein the hole conductors energetically different highest occupied molecular orbitals (HOMO). Optoelectronic device according to claim 17, characterized in that the last applied polymer layer with hole conductor function an energetically high lowest unoccupied Molecular orbital (LUMO) has. Optoelectronic device according to claim 18, characterized in that the last applied polymer layer with hole conductor function is an electron blocking layer. Optoelectronic device according to one or more of claims 1 to 19, characterized in that the Device several layers of polymers with electron conductor function includes, wherein the electron conductors energetically different highest occupied molecular orbitals (HOMO). Optoelectronic device according to claim 20, characterized in that the first applied polymer layer with electron conductor function an energetically low lowest Unoccupied molecular orbital (LUMO). Optoelectronic device according to claim 21, characterized in that the first applied polymer layer with electron conductor function is a hole blocking layer. Optoelectronic device according to one or more of claims 1 to 22, further comprising a cathode. Optoelectronic device according to one or more of claims 1 to 23, further comprising an encapsulation. Use of an optoelectronic device according to one or more of claims 1 to 24 as organic or polymeric light emitting diode, as organic solar cell, as organic Field effect transistor, as organic switching element, as organic Field quench element, as organic optical amplifier, as organic laser diode, as organic photoreceptor or as organic Photodiode. Use according to claim 25 as an OLED in a display, in a colored, multi-colored or full-color display, as a lighting element or as a backlight in a liquid crystal display (LCD). Use according to claim 26, characterized that the OLED is a white light emitting OLED. Method for producing an optoelectronic Device comprising the a) applying a first layer on a substrate, and b) applying at least one other Layer, wherein the first layer is an electrode which before, during or after application to the substrate with fluorine-containing Groups is provided. A method according to claim 28, characterized in that as the electrode indium tin oxide (ITO) or indium zinc oxide (IZO) is used and the fluorine-containing groups are applied after the application of the electrode to the substrate via a surface reaction or CF ₄ plasma treatment. Method according to Claim 28, characterized that the electrode is a conductive polymer and the fluorine-containing groups before or during application of the electrode on the substrate in the conductive polymer be introduced. Method according to one of claims 28 to 30, characterized in that the at least one further layer is applied by coating from solution. Method according to one or more of the claims 28 to 31, characterized in that for the further Layer a polymer with fluorinated groups, partially fluorinated Polymer, a polymer with perfluorinated side groups, an oligomer used with fluorinated groups or a fluorinated molecule becomes. Method according to claim 32, characterized in that the further layer has a charge injection function, an emitter function, a barrier function or combinations of these functions having. Formulation containing one or more fluorine-containing Polymers and / or fluorine-containing blends and / or fluorinated small ones Molecules in one or more solvents.