WO2016107663A1 - Formulations and electronic devices - Google Patents

Formulations and electronic devices Download PDF

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Publication number
WO2016107663A1
WO2016107663A1 PCT/EP2015/002422 EP2015002422W WO2016107663A1 WO 2016107663 A1 WO2016107663 A1 WO 2016107663A1 EP 2015002422 W EP2015002422 W EP 2015002422W WO 2016107663 A1 WO2016107663 A1 WO 2016107663A1
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Prior art keywords
preferably
organic
materials
characterized
compounds
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PCT/EP2015/002422
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German (de)
French (fr)
Inventor
Aurélie LUDEMANN
Nina TRAUT
Edgar Kluge
Yu AVLASEVICH
Stanislav Balouchev
Katharina Landfester
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Merck Patent Gmbh
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Priority to EP14004452 priority
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Publication of WO2016107663A1 publication Critical patent/WO2016107663A1/en

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    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0001Processes specially adapted for the manufacture or treatment of devices or of parts thereof
    • H01L51/0002Deposition of organic semiconductor materials on a substrate
    • H01L51/0003Deposition of organic semiconductor materials on a substrate using liquid deposition, e.g. spin coating
    • H01L51/0004Deposition of organic semiconductor materials on a substrate using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing, screen printing
    • H01L51/0005Deposition of organic semiconductor materials on a substrate using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing, screen printing ink-jet printing
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0001Processes specially adapted for the manufacture or treatment of devices or of parts thereof
    • H01L51/0002Deposition of organic semiconductor materials on a substrate
    • H01L51/0003Deposition of organic semiconductor materials on a substrate using liquid deposition, e.g. spin coating
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/56Processes or apparatus specially adapted for the manufacture or treatment of such devices or of parts thereof
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/54Material technologies
    • Y02E10/549Material technologies organic PV cells
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product
    • Y02P70/52Manufacturing of products or systems for producing renewable energy
    • Y02P70/521Photovoltaic generators

Abstract

The present invention relates to a formulation containing at least one solvent and nanoparticles comprising at least one surface-active polymer and at least one organically functional material, which material can be used for the production of functional layers of electronic devices. The invention further relates to electronic devices that can be obtained from said formulations.

Description

Formulations and electronic devices

The present invention relates to formulations for the production of electronic devices. Furthermore, the present invention relates to electronic devices and methods for their preparation.

Electronic devices containing organic, organometallic and / or polymeric semiconductors are increasingly gaining

Importance, which for cost reasons and because of their

Performance are used in many commercial products. As examples of charge transport materials may be made here on an organic base (for example, hole transportation triarylamine basis) in copying machines, organic or polymeric light emitting diodes (OLEDs or PLEDs), and referred to in display devices or organic photoreceptors in copiers. Organic solar cells (O-SC), organic field-effect transistors (O-FET), organic thin-film transistors (O-TFT), organic integrated circuits (O-IC), organic optical amplifiers and organic laser diodes (O-lasers) are in a advanced

Development and may in the future become very important.

Many of these electronic devices have on the following independently of the particular intended use general layer structure which can be adapted for the particular application:

(1) substrate,

(2) electrode, often metallic or inorganic, but also from

organic or polymeric conductive materials,

(3) Charge injection layer / s or intermediate layer / s, for example to compensate for unevenness of the electrode ( "planarisation layer"), often made of a conductive, doped polymer,

(4) organic semiconductors,

(5) possibly other charge transporting, charge or

Charge blocking layers, (6) a counter electrode, materials as mentioned under (2),

(7) encapsulation.

The above arrangement is the general structure of an organic electronic device, said various layers

can be combined so that in the simplest case an arrangement of two electrodes results, between which an organic layer. The organic layer fulfills in this case, all functions, including the emission of light in the case of OLEDs. Such a system is described for example in WO 90/13148 A1 on the basis of poly (p-phenylene).

However, a problem which arises in such a "three-coat system", the lack of control of the charge separation or lack of opportunity to optimize the various components in different layers with respect to their properties, as for example in SMOLEDs ( "small-molecule OLEDs") is easily solved by a multilayer structure. A "small molecule OLED" includes many cases, one or more organic hole injection layers, hole transport layers, emitting layers, electron transport layers and / or electron injection layers, and an anode and a cathode, wherein the entire system is usually on a glass substrate The advantage of such multi-layer structure. Is that the different

Functions of charge injection, charge transport and the emission to the various layers distributed and thus the properties of the respective layers can be modified separately. With this modification, the performance of the electronic devices can be greatly improved. A disadvantage of electronic devices based on the above-

Compounds described "small molecules", ie non-polymer based, is their preparation. Usually, non-polymeric compounds on evaporation techniques to electronic

Devices processed. This is especially for large area

Devices a major cost disadvantage is, as a multi-stage vacuum process is very costly in different chambers and must be controlled very accurately. Here would be more cost-effective and established coating methods from solution as zBTintenstrahldruck,

Airbrush method, roll-to-roll processes, etc., of great advantage.

The problem with these methods is among other things that the already widely applied in a used for the printing process set forth above solvent on the substrate layers on or detached. Due to this solubility already applied layers in the solvents used hereinafter, the layers are destroyed, at least the functioning and life of the devices is adversely affected. As a solution to this problem have been orthogonal

Solvent used, while the functional material a

dissolve layer to be applied, but not the layer to which the

Function material is applied. The problem here is the search for a suitable orthogonal solvents, such that the type of function to be applied to a functional layer material is severely limited.

Another approach consists in the crosslinking of layers on the further layers for the production of electronic devices are applied, as is set forth for example in EP 0637899 A1. Disadvantages of this approach are the need for crosslinking the crosslinkable groups that can lead to a reduction in the lifetime and performance of electronic devices.

Further 2011/076314 A1 aqueous formulations are known from WO containing nanoparticles. These formulations are already showing a good property profile. However, it is stated in this application that, preferably, high levels of surfactants for the preparation of the disclosed therein formulations. These surfactants can have detrimental effects on the life and performance of the available from these formulations electronic devices. Therefore, it is stated that the formulation used to prepare the surfactants should be removed to improve performance. However, the preparation of preferred formulations significantly increases the cost of this step.

Known processes for the production of electronic devices have a useful property profile. However, there is a permanent need for the properties of these methods

improve.

In particular, the process should be inexpensive to implement. Furthermore, the method for the production of very small structures should be suitable so that high-resolution displays by the method are available. Further, the method using should be able to be carried out by conventional printing methods.

These advantages should be achieved individually or jointly. An essential aspect here is that the available by the process of electronic devices should have excellent properties. in particular one of these properties, the life of electronic devices. A further problem is in particular the energy efficiency is, with an electronic device, the

solves predetermined task. In organic light emitting diodes, which can be based on low molecular weight compounds as well as polymeric materials, the light output should be particularly high, so that to achieve a certain light flux as little electric power has to be applied. Furthermore, the lowest possible voltage should also be necessary to obtain a predetermined luminance. Accordingly, these properties should by

Procedures are not adversely affected.

Furthermore, the electronic devices should be able to be used or adapted for many purposes. In particular, should the

retained performance of electronic devices over a wide temperature range.

Another problem can be seen in the electronic

Devices with an excellent performance to provide the most cost effective and consistent quality.

Surprisingly, it was found that these and other objects not explicitly mentioned, but the introduction of the herein

More connections discussed are derived or inferred, are achieved by formulations having all features of claim 1. Appropriate modifications of the formulations of the invention are provided in the claims referring back to claim 1 dependent claims under protection. The present invention is accordingly an

Formulation comprising at least a solvent and nanoparticles comprising at least one surfactant and at least one polymer organic functional material for the preparation of

is used functional layers of electronic devices.

A formulation of the invention comprises at least one

Solvents and nanoparticles.

The solvent can dissolve the surfactant polymer which is covered by the nanoparticles, and provides the continuous phase of an emulsion or a dispersion, depending on whether the nanoparticles are present in liquid or solid phase. In contrast, little to solve, preferably no part of the organic functional material contained in the nanoparticles in the solvent so that the solvent contained in the continuous phase can be referred to as a dispersant with respect to the organic functional material.

The solvents used in the present invention

refers to compounds that during manufacture of the electronic device of the layers at least in large part, ie, preferably at least 60 wt .-%, more preferably at least 80 wt .-%, most preferably at least 95 wt .-%, and

particularly preferred are substantially completely separated and not remain in the electronic device.

Preferably, the solvent is a polar solvent, wherein the solvent is preferably an ET (30) value of at least

having 180 kJ / mol, preferably at least 200 kJ / mol, measured at 25 ° C according to C. Reichardt, Angew. Chem., 91, 119 (1979).

Further, it can be provided that the solvent which is contained in the continuous phase of the formulation, water and / or comprises an alcohol having at most 6 carbon atoms. Here formulations are preferred which comprise at least 60 wt .-%, preferably as a solvent, particularly preferably at least 80 wt .-% and most preferably at least 95 wt .-% water and / or an alcohol having at most 6 carbon atoms. Alcohol having at most 6 carbon atoms include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 2-butanol, 2-methyl-2-propanol, 1-pentanol, 2- methyl-1 -butanol, 3-methyl-1-butanol, n-butanol, isobutanol, 1-pentanol, 2-methyl-1-butanol, neopentyl alcohol, 3-pentanol, 2-pentanol, 3-methyl-2- butanol and 2-methyl-2-butanol. Preferably methanol, ethanol and alcohols having up to 4 here are, preferably up to 3 carbon atoms, with methanol and ethanol are particularly preferred. Water to methanol and / or ethanol as a solvent preferably. Particularly preferred water as the solvent, so that preferred formulations preferably at least 60 wt .-%, more preferably at least 80 wt .-%, and comprise most preferably at least 95 wt .-% water as solvent. The surfactant polymer may preferably have a solubility in the solvent of the continuous phase, preferably in water at 25 ° C of at least 1 g / l, preferably more preferably at least 10 g / l and at least 20 g / l. The solubility can by means of known methods such as dynamic light scattering (DLS), turbidimetric measurements and viscometry be measured (BA Wolf., Pure & Appl. Chem., Vol. 57, No. 2, pp. 323-336, 1985).

Depending on the nature of the nanoparticles, the present formulation

preferably an emulsion or a dispersion. Here can include both solid and liquid particles of the formulation. Therefore, the particles of the discontinuous phase are independent of the

Physical state, ie, whether the particles are solid or liquid, referred to as nanoparticles. Preferably, the nanoparticles are present in solid form and accordingly preferred include only a small proportion of organic solvent. In another embodiment of the present invention, the

Formulation have a discontinuous phase, the nanoparticles are present in a liquid state, referred to herein as nano-droplets having an average diameter in the range 1 to 7000 nm, preferably in the range of 1 to 3000 nm, more preferably in the range of 5 to 2000 nm and most particularly preferably in the range from 5 to 1000 nm.

In another embodiment of the present invention, the formulation may comprise a discontinuous phase, the nanoparticles are present in the solid phase, said solid nanoparticles preferably have an average diameter in the range of 1 to 5000 nm, preferably in the range of 10 to 2000 nm, more preferably in range of 10 to 500 nm and most preferably in the range of 0 to 300 nm, and particularly preferably in the range of 20 to 100 nm.

In yet another embodiment of the present invention is the formulation, characterized in that more than 75% of the

, More preferably more than 90% and most preferably more than 98% have nanoparticles, preferably more than 80% of a diameter of 55% or less, preferably 50% or less, particularly preferably 20% or less, and most

preferably 10% or less different from the average diameter of all nanoparticles. According to one embodiment of the present invention, the proportion of nanoparticles can, whether liquid or solid, with a diameter in the range of preferably 10 to 300 nm, more preferably in the range of 20 to 100 nm, preferably at least 50 wt .-%, particularly preferably at least 80 wt .-%, respectively, based on the weight of all the nanoparticles. The mean values ​​of the particle diameter mentioned above relate to the number average.

The size and size distribution of nano-droplets and nanoparticles in emulsions and dispersions can be prepared using

Be obtained with standard techniques known in the art. Preferably, the diameter and the size distribution can be measured by dynamic light scattering (Chu, B., Laser Light

Scattering: Basic Principles and Practice, 2nd Edition. Academic Press (1992)).

The nanoparticles, whether liquid or solid, comprise at least one organic functional material and at least one surfactant polymer. The weight ratio of organic functional material to

surface-active polymer is preferably in the range from 1: 1 to 50: 1, more preferably in the range from 4: 1 to 12: 1 and most preferably in the range of 6: 1 to 8: 1. Here, this figure refers to the total weight of functional material and of surfactant polymer, which was used for the preparation of the formulation. It can preferably be provided that the surface-active polymer has a weight average molecular weight Mw in the range of 5,000 to 1,000,000 g / mol, preferably 10,000 to 500,000 g / mol, particularly preferably 15,000 to 100,000 g / mol and most preferably 20,000 to 80,000 g / mol having. The weight average molecular weight Mw can be obtained by gel permeation chromatography (GPC) against common standards, preferably polymers having identical or similar repeat units at 25 ° C are measured. In a preferred embodiment, the surfactant

Polymer having a surface tension ranging from 30 to 70 mN / m, particularly preferably in the range of 40 to 60 mN / m, measured according to Oberflächentensiometrie (ring method).

Preferred surfactants polymers have substantially no carboxyl groups (-CO2). the proportion by weight is preferably at most 5% of carboxyl groups in the surfactant polymer, preferably at most 1%, and most preferably at most 0.5%.

Preferred surfactants polymers have substantially no anionic groups, for example carboxyl and / or sulphate groups. the proportion by weight is preferably at most 5% of anionic groups in the surfactant polymer, preferably at most 1% and particularly preferably at most 0.5%. The anionicity of the anionic groups refers to a pH of 6.0, so that the underlying anionic groups acid groups having a pKa of less than 6.0.

The type of the surfactant polymer is not critical per se, but rigid surface-active polymers are preferred. According to a preferred embodiment, the persistence of the surfactant polymer may be less than the persistence of polyethylene glycol or polyvinyl alcohol. Particularly preferably, it can be provided that the persistence length of the surface active polymer is at least 20% greater than the persistence length of polyethylene glycol or polyvinyl alcohol. The persistence may be determined, inter alia, according to the light scattering method set forth above from the hydrodynamic volume. Further, it can be provided that the surface-active polymer is a polysaccharide or a polypeptide, said polysaccharides are particularly preferred. Polysaccharides are well known, and here under polymeric compounds which, in which a large number of monomeric

Sugar units are linked via a glycosidic bond.

Polysaccharides may have other groups or substituents are next to the repeating units based on sugar. Thus, the polysaccharides can be modified, for example by Hydoxyethylgruppen or similar substituents. Furthermore, the polysaccharide can be modified, for example by protein groups. Preferred polysaccharides are characterized in that preferably at least 50 wt .-%, particularly preferably at least 80 wt .-% and most preferably at least 95 wt .-% of the polysaccharide from monomeric sugar units, preferably constructed the pentoses and hexoses set forth below are.

Preferred Speicherpolysacchariden among other dextrans and starch, such as amylose, amylopectin and glycogen. Further preferred are hemicelluloses and galactomannans, which are preferably soluble in water. Preferred hemicellulose include Xyloglucans.

Preferred sugars on which polysaccharides are based include pentoses, preferably xylose and arabinose; and hexoses, preferably fructose, glucose, mannose and galactose.

Preferred polysaccharides include, in particular

Speicherpolysaccharide, which have a high solubility in water. Preferably, a polysaccharide can be used as surface active polymer based on glucose, mannose, fructose, galactose and / or xylose. Especially preferred, can be used as the surfactant polymer polysaccharides are preferably chosen from glucans, particularly preferably xyloglucans and / or mannans, galactomannans particularly preferred.

Furthermore include polypeptides of the preferred surface-active polymers. Polypeptides are well known in the art, these polymers based on monomers having at least one amino group and at least one carboxyl group, which are linked via amide bonds. Preferred polypeptides have similar properties such as polysaccharides set out above. This applies particularly to properties such as the stiffness of the polymers (persistence), the solubility and surface activity.

Preferred polypeptides are characterized in that preferably at least 50 wt .-%, particularly preferably at least 80 are constructed at least 95 wt .-% of the polypeptide from monomeric peptide units, preferably from natural amino acid units wt .-% and very particularly preferably , In general, polysaccharides are preferred to polypeptides.

Further, it can be provided that the surfactant polymer, preferably the polysaccharide is branched. Preferably the degree of branching in the range from 0 (linear) to 0.6 (hyper branched), may particularly preferably be in the range of 0.3 to 0.55, wherein this size can be determined by methods known in the art, for example by a combination of light scattering at small angles (LALLS) - gel permeation chromatography (GPC) of

Polysaccharides in aqueous solution (Li-Ping Yu, JE Rollings;... J. Appl Polym Be 33, 5, 1909-1921 (198)), and nuclear magnetic resonance spectroscopy (NMR) (D. Holtel, A. Burgath, H. Frey, Acta polymer, 48, 30-35 (1997)) and / or a combination of GPC / LSA / iscosity coupling (determination of long chain branching), and a combination of end group titration and HPLC / MS-MS (determination of the short chain branching. ). HPLC / MS-MS analysis is a system in which two mass spectrometers are coupled, wherein a separation of the substances is carried out by HPLC (JP Benskin, MG Ikonomou, Woudneh, B. million; J.

Chromatography A, 1247, 165-170, 2012)). Preferably, the

Degree of branching are determined by LALLS-GPC.

A preferred surfactant polymer, preferably a

Polysaccharide may be side chains with an average chain length in the range of 1 to 100, preferably 1 to 10 and particularly preferably having 1 to 5 repeating units, as measured by means of a

Combination of LS-DLS / SLS and / or GPC / LS / viscosity coupling and a combination of end group titration and HPLC / MS-MS and nuclear magnetic resonance spectroscopy (NMR), wherein the repeating units are preferably based on sugar molecules with 5 or 6 carbon atoms and particularly preferably form a ring having 6 ring atoms. The average chain length here refers to the number average.

A preferred surfactant polymer, preferably a

Polysaccharide can be a backbone with an average

Chain length of at least 30, preferably at least 40 and particularly preferably at least 60 repeating units, said size known methods can be determined by the skilled person, for example by a combination of LS-DLS / SLS and / or GPC / LS / viscosity-coupling and combination of

End group titration and HPLC / MS-MS and nuclear magnetic resonance spectroscopy (NMR), the methods described above and LS-DLS / SLS is particularly preferable. Preferably, the repeating units based on sugar molecules with 5 or 6 carbon atoms, particularly preferably form a ring with 6 ring atoms. The

average chain length here refers to the number average.

Further, it can be provided that the surfactant polymer, preferably the polysaccharide and / or the polypeptide is predominantly located on the surface of the nanoparticles.

The nanoparticles contained in the inventive formulation, comprise at least one organic functional material.

Functional materials are generally organic or inorganic materials which are introduced between the anode and cathode of an electronic device.

The term organic functional material referred to, among others, organic conductors, organic semiconductors, organic coloring matter,

in particular organic dyes, organic fluorescent

Compounds, organic phosphorescent compounds, organic light-absorbing compounds, organic photosensitive

Compounds, organic photosensitizers, and other organic photoactive compounds. The term organic functional material further comprises organo-metallic complexes of

Transition metals, rare earth metals, lanthanides and actinides.

Preferably, the organic functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, Excitonenblockier- materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, n-type dopant, Wide-band gap materials, electron blocking materials .

Hole-blocking materials and colorants. Preferred embodiments of organic functional materials are disclosed in detail in WO 2011/076314 A1, this document by reference thereto in the present application is recorded.

More preferably, the organic functional material is selected from the group consisting of fluorescent emitters,

phosphorescent emitters, host materials, matrix materials, Excitonenblockiermaterialien, electron transport materials,

Electron injection materials, hole transport materials,

Hole injection materials, n-dopants, wide-band-gap materials, electron blocking materials and hole blocking materials.

The organic functional material may be a compound with a low molecular weight, a polymer, an oligomer, or a dendrimer, wherein the organic functional material can also be present as a mixture. Thus, the mentioned nanoparticles two can

include various compounds having a low molecular weight, a compound having a low molecular weight and a polymer and / or two polymers (blend).

According to another preferred embodiment of the present invention the organic functional material is insoluble in the continuous phase.

For the purposes of the present invention, a material or compound in a solvent is insoluble if its solubility at 25 ° C less than 0.4 g / 100 ml, preferably less than 0.1 g / 100 ml, more preferably less than 0.001 g / 100 ml. Is a soluble material, or a compound, if the solubility of the material is greater than that of an insoluble material or an insoluble compound. Organic functional materials are described in many of the properties of the frontier orbitals which are set forth in more detail below. Molecular orbitals, in particular the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) whose energy levels and the energy of the lowest triplet state Ti or the lowest excited singlet state Si are the materials determined by quantum chemical calculations. For the calculation of organic substances without metals geometry optimization using the "Ground State / Semi-empirical / Default Spin / AM1 / Batch O / spin singlet" is performed first. Following is based on the optimized geometry an energy bill. Here, the method is " TD-SCF / DFT / Default spin / B3PW91 "with the base set" 6-31G (d) "used (charge 0, spin singlet). For metal-containing compounds, the geometry about the method is" Ground State / Hartree-Fock / Default

Spin / LanL2MB / Batch O / spin singlet "optimized. The energy bill is similar to the method described above for the organic substances with the difference that for the metal atom, the basic rate" (LanL2DZ "and for ligand based sentence" 6-31 G d) "is used to obtain the HOMO energy level hEH or LUMO energy level in LEH Hartree-units from the energy bill from this the basis of calibrated Cyclovoltammetriemessungen HOMO and LUMO energy levels in electron volts can be determined as follows..:

HOMO (eV) = ((heh * 27212) -0.9899) /1.1206

LUMO (eV) = ((LEH * 27212) -2.0041) /1.385

These values ​​are within the meaning of this application as HOMO and LUMO energy levels of the materials. The lowest triplet state Ti is defined as the energy of the triplet state with the lowest energy, resulting from the described quantum chemical calculation. The lowest excited singlet state Si is defined as the energy of the excited singlet state to the lowest energy, resulting from the described quantum chemical calculation.

The method described herein is independent of the used software package and always produces the same results. Examples frequently used programs for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).

Compounds having hole injection properties, also referred to herein

Hole injection materials known to facilitate or allow the

Transfer of holes, ie positive charges from the anode into an organic layer. In general, a hole injection material has a HOMO level that is in the range or the level of the anode is higher, ie eV generally at least -5.3.

Compounds having hole transport properties, also referred to herein

called hole transport materials are capable of holes, ie to carry positive charges, which are usually injected from the anode or an adjacent layer such as a hole injection layer. A hole transport material generally has a high HOMO level of preferably at least -5.4 eV. Depending on the structure of an electronic device, a hole transport material may also be as

used hole injection material.

Among the preferred compounds, the hole-injection and / or

having hole transport properties include, for example,

Triarylamine, benzidine, tetraarylsubstituted-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, Phenoxathiin-, carbazole, azulene, thiophene, pyrrole and furan derivatives and further O-, S- or N-containing heterocycles having a high HOMO (HOMO = highest occupied molecular orbital).

Particular mention may be as compounds, the hole-injection and / or hole-transport properties, phenylenediamine derivatives (US 3,615,404), arylamine derivatives (US 3,567,450), amino-substituted chalcone derivatives (US 3,526,501), styryl anthracene derivatives (JP-A -56- 46234 (), polycyclic aromatic compounds EP 1009041),

Polyarylalkane derivatives (US 3,615,402), fluorenone derivatives (JP-A-54- 110837), hydrazone derivatives (US 3,717,462), acylhydrazones, stilbene derivatives (JP-A-61-210363), silazane derivatives (US 4,950,950 ), polysilanes (JP-A-2-204996), aniline copolymers (JP-A-2-282263), thiophene oligomers (JP Heisei 1 (1989) (211399), polythiophenes, poly (N-vinyl carbazole) PVK) , polypyrroles, polyanilines and other electrically conductive macromolecules, porphyrin compounds (JP-A-63-2956965, US 4,720,432), aromatic dimethylidene-type compounds, carbazole compounds such as CDBP, CBP, mCP, aromatic tertiary amine and styrylamine compounds (US 4,127,412), such as Tnphenylamine benzidine type, Tnphenylamine from styrylamine type and Tnphenylamine of diamine-type. Also arylamine dendrimers can be used (JP Heisei 8 (1996) 193191), monomeric triarylamines (US 3,180,730), triaryl amines with one or more vinyl radicals and / or at least one functional group having active hydrogen (US 3,567,450 and US 3,658,520) or

Tetraaryldiamines (two tertiary amine units are linked via an aryl group). There may be even more Triarylaminogruppen in the molecule. Also, phthalocyanine derivatives, naphthalocyanine derivatives, butadiene derivatives, and quinoline derivatives such as Dipyrazino [2,3-f: 2 \ 3'hjquinoxalinhexacarbonitril are suitable. aromatic tertiary amines having at least two are preferred

Tertiary amine units (US 2008/0102311 A1, US 4,720,432 and US

5061569), such as NPD (α-NPD = 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl) (US 5061569), 232 TPD (= N, N'-bis (N , N'-diphenyl-4-aminophenyl) -N, N-diphenyl-4,4'-diamino-1, 1'-biphenyl) or MTDATA (MTDATA, or m-MTDATA = 4, 4 ', 4 "-tris [ 3-methylphenyl) phenyl-amino] triphenylamine) (JP-A-4-308688), TBDB (= N, N, N ', N'-tetra (4-biphenyl) diaminobiphenyls) TAPC (= 1, 1-bis (4-di-p-tolylaminophenyl) - cyclohexane), TAPPP (= 1, 1-bis (4-di-p-tolylaminophenyl) -3-phenylpropane) BDTAPVB (= 1, 4-bis [2- [4- [N, N-di (p-tolyl) amino] phenyl] vinyl] benzene), TTB (= NNN'.N'-tetra-p-tolyl ^^ '- diaminobiphenyl), TPD (= 4,4'-bis [N-3-methylphenyl] -N-phenylamino) biphenyl), N, N, N ', N'-tetraphenyl-4,4 "' - diamino-1, 1 ', 4 \ 1", 4 ", 1" '-quaterphenyl, also tertiary amines having carbazole units, such as TCTA (= 4- (9H-carbazol-9-yl) -N, N-bis [4- (9H-carbazol-9-yl) phenyl] benzenamine). also preferred are compounds hexaaza-triphenylene, according to US 2007/0092755 A1 as well as phthalocyanine derivatives (such as H 2 Pc, CuPc (copper = Phthaloc Yanin), CoPc, NiPc, ZnPc, PDPC, FePc, MnPc, ClAIPc, ClGaPc, CllnPc, CISnPc, Cl 2 SiPc, (HO) AlPc,

(HO) GaPc, VOPc, TiOPc, MoOPc, GaPc-O-GaPc).

Particularly preferred are the following triarylamine compounds of the formulas (TA-1) to (TA-6), in the documents EP 1162193 B1, EP 650955 B1, Synth. Are Metals 1997, 91 (1-3), 209, DE 19646119 A1,

WO 2006/122630 A1, EP 1860097 A1, EP 834945 A1, JP 08053397 A, US 6,251,531 B1, US 2005/0221124, JP 08292586 A, US 7,399,537 B2, US 2006/0061265 A1, EP 1661888 and WO 2009 / 041,635th The said compounds of the formulas (TA-1) to (TA-12) may also be substituted:

Figure imgf000021_0001
Figure imgf000021_0002
Figure imgf000021_0003

Figure imgf000021_0004

Formula 7 Formula TA-TA-8

Figure imgf000022_0001

Formula 9 formula TA TA-10

Figure imgf000022_0002

TA-11 formula 12 formula TA

Other compounds which can be used as hole injection materials are described in EP 0891121 A1 and EP 1029909 A1, injection layers generally described in US 2004/0174116 A1. Preferably perform these arylamines and heterocycles in

generally be used as hole injection and / or hole transport materials (to a HOMO of more than -5.8 eV against

Vacuum level), particularly preferably greater than -5.5 eV. Compounds which exhibit electron injection and / or electron transport properties, for example, pyridine, pyrimidine,

Pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline, anthracene, Benzanthracen-, pyrene, perylene, benzimidazole, triazine, ketone,

Phosphine oxide and phenazine derivatives, but also Tnarylborane and further O-, S- or N-containing heterocycles having a low LUMO (LUMO = lowest unoccupied molecular orbital). Particularly suitable compounds for electron transporting and electron injecting layers are metal chelates of 8-hydroxyquinoline (for example LiQ, AlQ.sub.3, GaCte, MgQ2, ZnQ2, LNQ 3, Zrq 4), BAlq, Ga-Oxinoid- complexes, 4-Azaphenanthren-5-ol-Be complexes (US 5,529,853 A, see FIG. formula ET-1), butadiene derivatives (US 4,356,429), heterocyclic optical brighteners (US 4,539,507), benzimidazole derivatives (US 2007/0273272 A1), such as TPBI (US 5,766,779. see formula ET-2), 1, 3,5-triazines, for example

Spirobifluorene-triazine derivatives (for example according to DE 102008064200), pyrenes, anthracenes, tetracenes, fluorenes, spirofluorene, dendrimers, tetracenes (for example rubrene derivatives), 1, 10-phenanthroline derivatives (JP 2003- 115387, JP 2004-311184 , JP-2001 -267080, WO 2002/043449), silanes cyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives such as Triarylboranderivate with Si (US 2007/0087219 A1, see FIG. formula ET-3 ), pyridine derivatives (JP 2004-200162), phenanthrolines, particularly 1, 0-phenanthroline derivatives such as BCP and Bphen, a plurality of through biphenyl or other aromatic groups connected

Phenanthrolines (US 2007-0252517 A1) or associated with anthracene phenanthroline (US 2007-0122656 A1, see FIG. 4 and formulas ET-ET-5).

Figure imgf000023_0001

TPBI

2,2 ', 2 "- (1,3,5-benzenetriyl) tris (1-phenyl-1 H-benzimi

Formula ET-1 ET-2 formula

Figure imgf000024_0001

Figure imgf000024_0002

Formula ET-5

Also suitable are heterocyclic organic compounds such as Thiopyrandioxide, oxazoles, Triazoie, imidazoles or oxadiazoles. Examples of the use of five-membered rings with N such as oxazoles, preferably 1, 3,4-oxadiazoles, for example, compounds of formulas ET-6, ET-7, ET-8 and ET-9, which, inter alia, in US 2007/0273272 A1 are set out; Thiazoles, oxadiazoles, thiadiazoles, Triazoie, including see US 2008/0102311 A1 and YA Levin, M p Skorobogatova, Khimiya

Geterotsiklicheskikh Soedinenii 1967 (2), 339-341, preferably

Compounds of the formula ET-10, silacyclopentadiene derivatives.

Preferred compounds are the following according to the formulas (ET-6) to (ET-10):

Figure imgf000024_0003

Formula ET-6

Figure imgf000025_0001

Formula ET-7

Figure imgf000025_0002

Formula ET-8

Figure imgf000025_0003

Formula ET-9

Figure imgf000025_0004

Formula ET-10

Also, organic compounds such as fluorenone derivatives, fluorenylidene methane, Perylentetrakohlensäure, anthraquinodimethane, diphenoquinone, anthrone and Anthrachinondiethylendiamin can be used.

2,9,10-substituted anthracenes (with 1- or 2-naphthyl and 4- or 3-biphenyl), or molecules that contain two anthracene moieties (. US2008 / 0193796 A1, see Formula ET-11) are preferred. Very advantageous is the combination of 9,10-substituted anthracene units with benzimidazole derivatives (US 2006 147747 A and EP 1551206 A1, see FIG. 12 and formulas ET-ET-13).

Figure imgf000026_0001

Formula ET-11

Figure imgf000026_0002

Formula ET-12 ET-13 formula

Preferably the lead compounds that can generate the electron-injection and / or electron transport properties, an LUMO of less than -2.5 eV (relative to vacuum level), particularly preferably of less than -2.7 eV.

The nanoparticles of the present formulation may comprise emitter. The term emitter refers to a material which, after excitation, which can be effected by transmission of any kind of energy, a radiation-affected transition with the emission of light in a

Ground state allowed. In general, two classes of emitters are known, namely fluorescent and phosphorescent emitters. The term fluorescent emitter refers to materials or compounds in which a radiation-prone transition from a singlet excited state occurs to the ground state. The term

phosphorescent emitter preferably designates luminescent materials or compounds comprising transition metals.

Emitters are often referred to as dopants, if the dopants cause the properties set forth above in a system. Under a dopant a matrix material and a dopant is understood to mean that component in a system containing, their proportion is the smaller in the mixture. Accordingly, comprising a matrix material and a dopant, is under a matrix material in a system to mean the component whose content is the greater of the mixture. The term phosphorescent emitters and phosphorescent dopants can be understood accordingly, for example.

include compounds that can emit light, including fluorescent and phosphorescent emitter emitter. These include compounds with stilbene, Stilbenamin-, Styrylamin-, coumarin, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, Paraphenylen-, perylene, Phatolocyanin-, porphyrin, ketone , quinoline, imine, anthracene and / or pyrene structures. Particularly preferred compounds that can emit light even at room temperature with high efficiency from the triplet state, so electrophosphorescence showing instead electrofluorescence, which frequently causes an increase in energy efficiency. This purpose are firstly compounds which contain heavy atoms having an atomic number of greater than the 36th preference

Compounds containing d- or f transition metals which meet the above condition. Particularly preferred are relevant here

Compounds containing elements of the group 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt). The functional compounds, for example, various complexes here in question, as described for example in WO 02/068435 A1, WO 02/081488 A1, EP 1239526 A2 and WO 04/026886 A2 describes.

By way of example, preferred compounds are set forth, which can serve as fluorescent emitters. Preferred fluorescent emitter are selected from the class of monostyrylamines,

Distyrylamines, tristyrylamines, tetrastyrylamines, the styryl phosphine, the Styrylether and arylamines. A monostyrylamine is meant a compound that contains a substituted or unsubstituted styryl group and at least one, preferably aromatic, amine. A distyrylamine is meant a compound containing two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine. A tristyrylamine is meant a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine. A tetrastyrylamine a

understood compound, the unsubstituted or substituted four

contains styryl groups and at least one, preferably aromatic, amine. The styryl groups are particularly preferably stilbenes, which may be further substituted too. Corresponding phosphines and ethers are defined analogously to the amines. An arylamine or an aromatic amine in the sense of the present invention, a

understood compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring system is a fused ring system, preferably having at least 14 aromatic ring atoms. Preferred examples thereof are aromatic anthracenamines, aromatic

Anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic or aromatic chrysenamines chrysenediamines. An aromatic anthracenamine is meant a compound in which a diarylamino group is directly bonded to an anthracene group, preferably in the 9-position. An aromatic anthracenediamine is meant a compound in which two Diarylanninogruppen are directly bonded to an anthracene group, preferably in the 2,6- or 9,10-position. Aromatic pyrenamines, pyrenediamines, and chrysenamines

Chrysenediamines are defined analogously to the Diarylanninogruppen are preferably bound in the 1-position or in the 1, 6-position on the pyrene.

Further preferred fluorescent emitters are selected from fluorine-indeno amines or diamines, are set out, inter alia, in WO 06/122630; or diamines benzoindenofluorenamines set forth inter alia in WO 2008/006449; and fluorine-amines or diamines Dibenzoindeno- set forth inter alia in WO 2007/140847.

Examples of compounds which can be used as a fluorescent emitter, from the class of styrylamines are substituted or unsubstituted tristilbenamines or the dopants in WO

06/000388, WO 06/058737, WO 06/000389, WO 07/065549 and WO 07/115610. distyrylbenzene and

Distyrylbiphenyl derivatives are described in US 5,121,029th More styrylamines can be found in US 2007/0122656 A1.

Particularly preferred styrylamine compounds are disclosed in US

7250532 B2 compounds described of the formula EM-1 and the compounds of formula EM-2 described in the DE 10 2005 058 557 A1:

Figure imgf000030_0001

Formula EM-1 EM-2 formula

Particularly preferred triarylamine compounds are in the CN

1583691 A, JP 08/053397 A, US 6251531 B1, EP 1957606 A1, US 2008/0113101 A1, US 2006/210830 A, WO 08/006449 and DE 102 008 035 413 compounds of the formulas set forth EM-3 to EM

Figure imgf000030_0002
Figure imgf000030_0003

Formula EM-5 EM-6 formula

Figure imgf000031_0001
Figure imgf000031_0002

Figure imgf000031_0003

Figure imgf000031_0004

Formula EM-13 EM-14 formula

Figure imgf000032_0001

Formula EM-15

Other preferred compounds that can be used as a fluorescent emitter are selected from derivatives of naphthalene, anthracene, tetracene, benzanthracene, Benzphenanthren (DE 10 2009

005746), fluorene, fluoranthene, Periflanthen, Indenoperylen, phenanthrene, perylene (US 2007/0252517 A1), pyrene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, Pentaphenylcyclopentadien, fluorene,

Spirofluorene, rubrene, coumarin (US 4,769,292, US 6,020,078, US

2007/0252517 A1), pyran, oxazole, benzoxazole, benzothiazole,

Benzimidazole, pyrazine, cinnamic, diketopyrrolopyrrole, acridone and quinacridone (US 2007/0252517 A1).

Of the anthracene compounds are particularly preferred in the 9,10-position substituted anthracenes such as 9,10-diphenylanthracene and 9,10-

Bis (phenylethynyl) anthracene. Also, 1, 4-bis (9'-ethynylanthracenyl) benzene is a preferred dopant.

Also preferred are derivatives of rubrene, coumarin, rhodamine, quinacridone, such as DMQA (= Ν, Ν'-dimethylquinacridone), dicyano methylenpyran, such as DCM (= 4- (dicyanoethylene) -6- (4-dimethylamino-styryl 2-methyl) -4H-pyran), thiopyran, polymethine, pyrylium and

Thiapyryliumsalzen, Periflanthen and Indenoperylen. Blue fluorescent emitters are preferably polyaromatics such as 9,10-di (2-naphthylanthracen), and other anthracene derivatives, derivatives of tetracene, xanthene, perylene, such as 2,5,8, 1-tetra-f-butyl-perylene, phenylene , for example 4,4 '- ((bis (9-ethyl-3-carbazovinylen) -1, 1'-biphenyl, fluorene, fluoranthene, Arylpyrene (US 2006/0222886 A1), arylenevinylenes US 5,121,029, US 5,130,603), bis ( azinyl) imine boron compounds (US

2007/0092753 A1), bis (azinyl) methenverbindungen and Carbostyryl- connections.

Further preferred blue fluorescent emitters in CHChen et al .:

"Recent developments in organic electroluminescent materials" Macromol. Symp. 125, (1997) 1-48 and "Recent progress of molecular organic electroluminescent materials and devices" Mat. Sci. And Eng. R, 39 (2002), 143-222 described ,

Further preferred blue fluorescent emitters in DE

102008035413 disclosed hydrocarbons.

Way of example, preferred compounds are set forth which can be used as phosphorescent emitters.

Examples of phosphorescent emitters are WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614 and WO 05/033244 are removed. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as they are to those skilled in the art of organic electro luminescence known are, and the expert can use more phosphorescent complexes without inventive step.

Phosphorescent metal complexes preferably contain Ir, Ru, Pd, Pt, Os and Re.

Preferred ligands include 2-phenylpyridine derivatives, 7,8-Benzochinolin- derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives, 1-phenyl isoquinoline derivatives, 3-phenyl isoquinoline derivatives or 2-phenyl quinoline derivatives. All these compounds can be substituted, for example blue with fluorine, cyano and / or trifluoromethyl. Auxiliäre ligands are preferably acetylacetonate or picolinic acid.

In particular complexes of Pt or Pd with tetradentate ligands of the formula EM-16 are suitable as emitters.

Figure imgf000034_0001

Formula EM-16

The compounds of formula EM-16 are detailed in

US 2007/0087219 A1 stated, reference being made to the explanation of the substituents and indices in the formula above to this document for purposes of disclosure. Further, Pt-porphyrin enlarged ring system (US 2009/0061681 A1) and Ir complexes are suitable, such as 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin-Pt (II) , tetraphenyl-Pt (II) -tetrabenzoporphyrin (US 2009/0061681 A1), c / 's-bis (2-phenylpyridinato-N, C 2') Pt (II), c / 's-bis (2- (2 , -thienyl) pyridinato-N, C 3 ') Pt (II), c / s-bis (2- (2'-thienyl) quinolinato-N, C 5') Pt (II), (2- (4 , 6-difluorophenyl) pyridinato- N, C 2 ') Pt (II) (acetylacetonate), or tris (2-phenylpyridinato-N, C 2'), lr (lll) (= Ir (ppy) 3, green), bis (2-phenyl-pyridinato-N, C 2) Ir (III) (acetylacetonate) (= Ir (ppy) 2acetylacetonat, green, US 2001/0053462 A1, Baldo, Thompson et al. Nature 403, (2000), 750- 753), bis (1-phenylisoquinolinato-N, C 2 ') (2-phenylpyridinato-N, C 2') (iridium (III), bis (2-phenylpyridinato-N, C 2 ') 1- phenylisoquinolinato-N, C 2 ') iridium (III) bis (2- (2'-benzothienyl) pyridinato- N, C 3' ((III) acetylacetonate), bis (2- (4 ', 6'-difluorophenyl)) iridium pyridinato- N, C 2 ') (iridium (III) piccolinat) (Flrpic, blue), (2- (4 ', 6'-difluorophenyl) - pyridinato-N, C 2') to Ir (III) (tetrakis (1-pyrazolyl) borate), tris (2- (biphenyl-3-yl) -4- tertbutylpyridin) iridium (III), (ppz) 2 Ir (5phdpym) (US 2009/0061681 A1), (45ooppz) 2 Ir (5phdpym) (US 2009/0061681 A1), derivatives of 2-phenylpyridine Ir complexes, such as eg PQiR (= iridium (III) bis (2-phenyl quinolyl-N, C 2 ') acetylacetonate), tris (2-phenylisoquinolinato-N, C) Ir (III) (red), bis (2- (2 '-benzo [4,5-a] thienyl) pyridinato-N, C 3) Ir (acetylacetonate) (

[Btp 2 lr (acac)], red, Adachi et al .; Appl. Phys. Lett. 78 (2001), 1622-1624).

Also suitable are complexes of trivalent lanthanides such as Tb 3+ and Eu 3+ (J.Kido et al. Appl. Phys. Lett. 65 (1994), 2124 Kido et al. Chem. Lett. 657, 1990, US 2007 / 0252517 A1) or phosphorescent

Complexes of Pt (II), Ir (l), Rh (l) with Maleonitrildithiolat (Johnson et al., JACS 105, 1983, 1795), Re (l) -Tricarbonyl-diimine complexes (Wrighton, JACS 96, 1974 998 (among others), Os II) complexes (with cyano ligands and bipyridyl or phenanthroline ligands Ma et al., Synth. Metals 94, 1998, 245).

Other phosphorescent emitters with tridentate ligands are described in US 6824895 and US 10/729238. Red-emitting phosphorescent complexes can be found in US 6835469 and US 6,830,828th

Particularly preferred compounds as phosphorescent

For dopants used, include those described in US 2001/0053462 A1 and Inorg. Chem. 2001, 40 (7), 1704-1711, JACS 2001, 123 (18), 4304- 4312 described compounds of formula EM-17 and derivatives thereof.

Figure imgf000036_0001

Formula EM-17

Derivatives are described in US 7378162 B2, US 6835469 B2 and JP 2003/253145 A.

Further, in US 7238437 B2, US 2009/008607 A1 and EP 1348711, compounds described according to formula EM-18 to EM-21 and its derivatives are used as an emitter.

Figure imgf000036_0002

Formula EM-18 EM-19 formula

Figure imgf000036_0003

Formula EM-20 formula E -21 Quantum dots can also be used as an emitter, wherein these materials are disclosed in detail in WO 2011/076314 A1.

Compounds, which are used as host materials, in particular together with emissive compounds include materials of different material classes.

Host materials generally have larger band gaps between HOMO and LUMO on than the emitter materials used. In addition, preferred host materials either properties show a hole or electron transport material. Furthermore, host materials both electron hole transport properties, can also have.

Host materials are sometimes also referred to as matrix material, especially when the host material in combination with a

phosphorescent emitter is used in an OLED.

Preferred host materials or co-host materials which are used in particular in conjunction with fluorescent dopants are selected from the classes of oligoarylenes (for example, 2,2 ', 7,7'-tetraphenyl accordance with EP 676461 or dinaphthylanthracene), in particular the oligoarylenes containing condensed aromatic groups, such as anthracene, benzanthracene, Benzphenanthren (DE 10 2009 005 746, WO 09/069566), phenanthrene, tetracene, coronene, chrysene, fluorene,

Spirobifluorene, perylene, phthaloperylene, naphthaloperylene, decacyclene, rubrene, the oligoarylenevinylenes (such as DPVBi = 4,4'-bis (2,2-diphenyl-ethenyl) -1, 1 '-biphenyl) or spiro-DPVBi as described in EP 676461), (WO 04/081017, for example, in accordance with) the polypodal metal complexes, in particular metal complexes of 8-hydroxyquinoline, for example (= hydroxyquinoline aluminum (III) tris (8-)) AlQ.sub.3 or bis (2-methyl-8-quinolinolato) -4- (phenylphenolino - lato) aluminum, also with imidazole chelate (US 2007/0092753 A1) and the quinoline metal complexes, aminoquinoline metal complexes, Benzochinolin- metal complexes, the hole-conducting compounds (for example according to WO 04/058911), the electron-conducting compounds, in particular ketones , phosphine oxides, sulfoxides, etc. (for example, according to WO 05/084081 and WO 05/084082), the atropisomers (for example according to WO 06/048268), the boronic acid derivatives (for example according to WO 06/117052) or

Benzanthracenes (for example according to WO 08/145239).

Particularly preferred compounds which may serve host materials as host materials or copolymers are selected from the classes of oligoarylenes containing anthracene, benzanthracene and / or pyrene, or atropisomers of these compounds. An oligoarylene the purposes of the present application is to be understood to be a compound in which at least three aryl or arylene groups are bound to each other. Preferred host materials are most preferably selected from compounds of formula (H-1):

Ar 3 - (ArVAr 5 (H-1) wherein Ar 3, Ar 4, Ar 5 at each occurrence is identical or different is an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may optionally be substituted, and p is an integer is in the range of 1 to 5; it being understood that the sum of π-electrons in Ar 3, Ar 4 and Ar 5 is at least 30, when p = 1 and is at least 36 if p = 2, and at least 42 is when p = 3.

Particularly preferably the group Ar 4 in the compounds of the formula (H-1) for anthracene and the groups Ar 3 and Ar 5 are bonded to 9- and 10-position, which groups may be optionally substituted. Most particularly preferred is at least one of Ar 3 and / or Ar 5 is a condensed aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl, or 2-, 3-, 4-, 5-, 6- or 7 benzanthracenyl. Anthracene-based compounds are described in US 2007/0092753 A1 and US 2007/0252517 A1, for example, 2- (4-methylphenyl) -9, 10-di- (2-naphthyl) anthracene, 9- (2-naphthyl) -10- (1, 1 '- biphenyl) anthracene, and 9,10-bis [4- (2,2-diphenylethenyl) phenyl] anthracene, 9,10-diphenylanthracene, 9,10-bis anthracene (phenylethynyl) and 1, benzene 4-bis (9'-ethynylanthracenyl). and compounds having two anthracene moieties (US 2008/0193796 A1), for example, 10,10 · -ΒΪ5 [1, 1 \ 4 ', 1 "] terphenyl-2-yl-9,9'-bisanthracenyl are preferred.

Further preferred compounds are derivatives of aryl amine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadienes, tetraphenylcyclopentadiene, Pentaphenylcyclopentadien, coumarin, oxadiazole, bisbenzoxazoline, oxazole, pyridine, pyrazine, imine, benzothiazole, benzoxazole, benzimidazole (US 2007/0092753 A1), for example 2,2 ', 2 "- (1, 3,5- phenylene) tris [1-phenyl-1 H-benzimidazole], aldazine, stilbene, Styrylarylen- derivatives, including 9,10-bis [4- (2,2 -diphenylethenyl) phenyl] anthracene and distyrylarylene derivatives (US 5,121,029), diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, diketopyrrolopyrrole, polymethine, cinnamic acid esters and fluorescent dyes.

Particularly preferred are derivatives of aryl amine and styrylamine, including TNB (= 4,4'-bis [N- (1-naphthyl) -N- (2-naphthyl) amino] biphenyl). Metal complexes such Oxinoid- LiQ or AlQ.sub.3 can be used as co-hosts. Preferred compound having oligoarylene as a matrix are described in U.S.

2003/0027016 A1, US 7,326,371 B2, US 2006/043858 A, WO 2007/114358, WO 08/145239, JP 3148176 B2, EP 1009044, US 2004/018383, WO 2005/061656 A1 , EP 0681019 B1, WO 2004/013073 A1, US 5,077,142, WO 2007/065678 the set and DE 102009005746, particularly preferred compounds represented by formulas H-2 to H-described eighth

Figure imgf000040_0001

Formula H-2 H-3 formula

Figure imgf000040_0002

Formula H-8

Further comprise compounds that can be used as a host or matrix materials, materials that are used in conjunction with phosphorescent emitters. These compounds can also be used as structural elements in polymers, include CBP (Ν, Ν-biscarbazolylbiphenyl), carbazole derivatives (for example according to WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 08/086851), Azacarbazole (for example, according to the

EP 1617710, EP 1617711, EP 1731584 or JP 2005/347160), ketones (for example according to WO 04/093207 and DE 102008033943), phosphine oxides, sulfoxides and sulfones (for example according to WO 05/003253), oligophenylenes, aromatic amines (for example according to US 2005/0069729), bipolar matrix materials (for example according to WO 07/137725), silanes (e.g., B., according to WO 05/111172), 9,9-Diarylfluorenderivate (eg according to DE 102008017591) , Azaborole or Boronester (for example, according to the

WO 06/117052), the triazine derivatives (for example according to DE 102008036982), indolocarbazole derivatives (for example according to WO 07/063754 or WO 08/056746), Indenocarbazolderivate (eg according to DE 102009023155 and DE 102009031021), Diazaphospholderivate (eg according to DE 102009022858), triazole derivatives, oxazole and oxazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, distyrylpyrazine derivatives, thiopyran dioxide derivatives, phenylenediamine derivatives, tertiary aromatic amines, styrylamines, amino-substituted chalcone derivatives, indoles, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic dimethylidene compounds, carbodiimide derivatives, metal complexes of 8-hydroxyquinoline derivatives such as AlQ 3 that can 8- hydroxyquinoline complexes also Triarylaminophenol ligands include (US 2007/0134514 A1), metal complex polysilane compounds as well as thiophene, benzothiophene and dibenzothiophene derivatives.

Examples of preferred carbazole derivatives are mCP (= 1,3-N, N-dicarbazole-benzene (= 9.9 '- (1, 3-phenylene) bis-9H-carbazole)) (Formula H-9), CDBP (= g.g '^^' - Dimethylfl -biphenylH ^ '-. diy bis-gH-carbazol), 1, 3- bis (N, N'-dicarbazole) benzene (= 1, 3-bis (carbazol-9 yl) benzene), PVK

(Polyvinyl carbazole), 3,5-di (9H-carbazol-9-yl) biphenyl and CMTTP

(Formula H10). Particularly preferred compounds are 2007/0128467 A1 in the US and US 2005/0249976 A1 above (formulas H 11 to H-13).

Figure imgf000042_0001

Formula H-9 form l H-10

Figure imgf000042_0002

Formula H-11 H-12 formula

Figure imgf000042_0003

Formula H-13

Preferred Si Tetraaryle are set out for example in US 2004/0209115, US 2004/0209116, US 2007/0087219 A1 and in H. Gilman, EA Zuech, Chemistry & Industry (London, United Kingdom), 1960, the 120th Particularly preferred Si-Tetraaryle be described by the formulas: H-14 to H 21st

Figure imgf000043_0001

Formula H-14 H-15 formula

Figure imgf000043_0002

Triphenyl [4- (9-phenyl-9H-fluoren-9-yl) phenyl] silane formula H-16 H-17 formula

Figure imgf000043_0003

Formula H-20 H-21 formula Particularly preferred compounds for preparing the matrix for phosphorescent dopants include in the

DE 102009022858, DE 102009023155, EP 652 273 B1, the set WO 07/063754 and WO 08/056746, particularly preferred compounds represented by formulas H-22 to H-25 will be described.

Figure imgf000044_0001

Formula H-22 H-23 formula

Figure imgf000044_0002

Formula H-24 H-25 formula

In view of the inventively employable functional

Compounds that can serve as host material are particularly preferred substances having at least one nitrogen atom. These preferably include aromatic amines, triazine, and carbazole derivatives. To view particular carbazole derivatives, a surprisingly high efficiency. Triazine derivatives result in unexpectedly long lifetimes of the electronic devices with said compounds. It may also be preferable to use a number of different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Also preferred is the use of a mixture of a ladungstrans- transporting matrix material and an electrically inert matrix material, which is not, or not involved to a significant extent on the charge transport, as described for example in WO 2010/108579. Furthermore, compounds can be used, which improve the transfer from the singlet state to the triplet state and which, employed in support of the functional compounds having emitter properties, improve the phosphorescence of these compounds. For this purpose are, in particular, carbazole and bridged carbazole dimer, as described for example in WO 04/070772 A2 and WO 04/113468 A1. Furthermore, this ketones, phosphine oxides, sulfoxides, sulfones, silane derivatives and similar compounds are suitable, as described for example in WO 05/040302 A1. Under n-dopants are reducing agents herein, ie

Electron donors understood. Preferred examples of n-dopants are W (hpp) 4 and other electron-rich metal complexes according to the WO 2005/086251 A2, P = N-compounds (for example WO 2012/175535 A1, WO 2012/175219 A1), Naphthylencarbodiimide (for example WO 2012 / 168358 A1), fluorenes (for example, WO 2012/031735 A1), radicals and diradicals (for example, EP 1837926 A1, WO 2007/107306 A1), pyridines (for example, EP 2452946 A1, EP 2463927 A1), N-heterocyclic compounds (for example WO 2009 / 000237 A1) and acridines and phenazine (eg US 2007/145355 A1). Furthermore, the nanoparticles can be used as functional material is a wide-band gap material included. Among wide-band gap material is meant a material in accordance with the disclosure of US 7,294,849. These systems show particularly advantageous performance in electroluminescent devices.

Preferably, the used as the wide-band-gap material

Connecting a band gap (band gap) of 2.5 eV or more, preferably

3.0 eV or more, and more preferably from 3.5 eV or more. The band gap can be calculated, inter alia, of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) by the energy levels.

Furthermore, the nanoparticles can have a as a functional material

Hole-blocking material (hole blocking material; HBM) include. On

Hole-blocking material means a material which in a

A multilayer composite is arranged the passage of holes (positive charges) prevented or minimized, especially if this material in the form of a layer adjacent to an emitting layer or a hole-conducting layer. In general, a hole blocking material has a lower HOMO level than the hole transport material in the

adjacent layer. Hole blocking layers are often provided between the light emitting layer and the electron transport layer in OLEDs.

Basically, any known hole blocking material can be used. In addition to the other hole blocking materials are set forth elsewhere in the present application are

useful hole-blocking materials, metal complexes (US 2003/0068528), such as bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (BAlq). Fac-tris (1-phenylpyrazolato-N, C2) iridium (III) (Ir (ppz) 3) is also used for these purposes (US 2003/0 75553 A1).

Phenanthroline derivatives such as BCP, or phthalimides, such as TMPP may also be used. Further useful hole-blocking materials in the WO

00/70655 A2, WO 01/41512 and the WO 01/93642 A1.

Furthermore, the nanoparticles can have a as a functional material

include, electron blocking material (EBM electron blocking material). An electron blocking material refers to a material which prevents the passage of electrons in a multi-layer composite or minimized, especially if this material adjacent in the form of a layer is disposed in an emission layer or an electron-conductive layer. In general, an electron blocking material has a higher LUMO level than the electron transport material in the adjacent layer.

In principle, any known electron blocking material may be used. In addition to other electron-blocking materials are set forth elsewhere in the present application are suitable electron blocking materials transition metal complexes such as Ir (ppz) 3 (US 2003/0175553). Preferably, the electron blocking material may be selected from amines, triarylamines and their derivatives.

Furthermore, the nanoparticles can have a as a functional material

Exciton (exciton blocking material; ExBM) include. An exciton refers to a material which in a

Multilayer the passage of excitons is prevented or minimized, especially if this material is arranged adjacent in the form of a layer to an emitting layer. The exciton should preferably have a higher triplet or singlet level than the emission layer or other adjacent layer. In the art, the choice of suitable compounds is widely known, wherein the suitability of the compounds as the exciton is dependent on the energy gap of the adjacent layer. Preferably, it can be assumed that a convenient exciton a larger energy gap - singlet or triplet energy gap - having as the functional material of the adjacent layer, preferably of the emitter layer. In addition to further Excitonenblockiermaterialien set forth elsewhere in this application, are among the

suitable Excitonenblockiermaterialien substituted triarylamines, wherein substituted triarylamines, inter alia, in US 2007/0134514 A1 are set forth in detail. Examples include MTDATA or 4,4 ', 4 "-tris (N, N-diphenylamino) triphenylamine (TDATA), which

Compounds preferred for Excitonenblockiermaterialien

Electron blocking material can be used.

Furthermore, N-substituted carbazole compounds such as TCTA, or heterocycles, such as BCP, expedient.

Metal complexes such as Ir (ppz) 3 or Alq3 can also be used for this purpose. A colorant according to DIN 55943, the collective name for all colorants. Among the coloring agents include soluble dyes and inorganic or organic pigments. These colorants may be used individually or several as a mixture of two or more. In particular, mixtures of organic color pigments can be used with soluble organic dyes. Furthermore, the mixtures may be used, which include inorganic and organic pigments. In addition, mixtures may be used containing, in addition to the inorganic pigments soluble organic dyes. Furthermore, the mixtures are useful, include the soluble dyes and inorganic and organic pigments.

The power absorbed by the colorants light energy can be transferred to other materials in the form of light or any other form of energy. Preferably coloring agents are used that are used in connection with organic solar cells (O SCs), organic optical detectors, organic photoreceptors, organic electrical sensors or other electronic devices, which absorb light use.

In addition to other colorants elsewhere in the

are set forth in the present application, are among the suitable colorants phthalocyanines, azo dyes, perylene diimides, porphyrins, squaraines and isomers and derivatives of these compounds.

Preferably, the colorant may be selected from the group of the perylenes, ruthenium dyes, phthalocyanines, azo dyes, perylene diimides, porphyrins and squaraines. Furthermore, the Bai Yu et. al., in Nature Materials, Vol. 7, 626 (2008) and B. O'Regan et. al., Nature 353, 737 (1991), described ruthenium complexes and the Bessho et al, Chem. Commun. 3717 (2008), outlined complexes based on copper.

Further suitable coloring agents are from the group of acridines, anthraquinones, Aarylmethane, diarylmethanes, triarylmethane, azo dyes, cyanine dyes, diazonium dyes, nitro dyes, nitroso dyes, quinone imines, azine dyes, Eurhodinen, Safranine, Induline, indamines, Indophenole, oxazines, Oxazone, thiazines, thiazoles, xanthenes, fluorenes, Pyronine, fluorones and Rhodamine.

Besides the abovementioned colorants, the nanoparticles may include charge generating materials which have a similar function as the colorant. Charge generating materials are used, for example, for electrophotographic devices. Thus, charge generating materials, for example, Paul

M.Borsenberger and David S.Weiss in Organic Photoreceptors for

xerography; Marcel Dekker, Inc., 1998, Chapter 6, and KY Law, Chem. Rev. Vol. 93, 449-486 (1993) summarized, so that these charge-generating materials may also be regarded as an appropriate colorant. Further provide organic compounds which include a fused ring system such as anthracene, naphthalene, pentacene and tetracene derivatives, suitable colorants represents.

Furthermore, preferred functional compounds which can be used in the nanoparticles as the organic functional material, a molecular weight of 10000 g / mol, particularly preferably of at most 5000 g / mol and very particularly preferably of at most 3000 g / mol. further functional compounds, which are characterized by a high glass transition temperature are of particular interest. In this context, in particular, functional compounds, which may be used in the nanoparticles as the organic functional material, preferably having a glass transition temperature of at least 70 ° C, more preferably of at least 00 ° C, very particularly preferably of at least 125 ° C and particularly preferably comprise of at least 150 ° C, determined according to DIN 51005th The nanoparticles can be used as organic functional materials,

Polymers. The compounds set forth above, as the organic functional materials, which are often a relatively small

have molecular weight, can also be mixed with a polymer. It is also possible to use these compounds in a covalently

incorporate polymer. This is possible in particular with compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or Boronsäureester, or with reactive, polymerizable groups, such as olefins or oxetanes. This can be used as monomers for producing corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably carried out via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible that

to crosslink the polymers via such groups. The compounds and polymers of the invention can be used as crosslinked or non-crosslinked layer.

Polymers which can be used as organic functional materials often comprise units or structural elements which in

Frames were described of the compounds set forth above, including those described in WO 02/077060 A1, WO 2005/014689 A2 and in the disclosed and described in WO 2011/076314 A1 listed extensively. These are considered by reference into the present application. The functional materials may be derived for example from the following classes:

Group 1: the structural elements, the hole-injection and / or

can generate hole-transporting properties;

Group 2: the structural elements, the electron-injection and / or

can produce electron-transporting properties; Group 3: structural elements which combine the properties set out in relation to Group 1 and 2;

Group 4: the structural elements which have light-emitting properties, in particular phosphorescent groups;

Group 5: structural elements which the transition from the so-called

improve the singlet state to the triplet state;

Group 6: structural elements which the morphology or the

affect the emission color of the resultant polymers;

Group 7: structural elements, typically as a backbone

be used;

Group 8: Structural elements of the absorption properties

affect polymer so that they can be viewed as a colorant.

The structural elements can in this case also have different functions, so that a clear assignment is not necessarily appropriate. For example, a structural element of the group 1 can also serve as a backbone.

Preferably, the polymer used as the organic functional material having hole transporting or hole injection properties may comprise comprising structural elements of Group 1, units corresponding to

Hole-transport or hole injection materials meet previously stated. Further preferred structural elements of the group 1 are, for example, triarylamine, benzidine, tetraaryl-para-phenylene diamine, carbazole, azulene, thiophene, pyrrole and furan derivatives and further O-, S- or N-containing heterocycles having a high HOMO , These arylamines and heterocycles preferably have a HOMO of more than -5.8 eV (relative to vacuum level), particularly preferably of more than -5.5 eV.

among other polymers are preferred hole-transport or

Hole injection properties, comprising at least one of the following repeating unit represented by formula HTP-1

Ar 13

_L_ Ar t L! _Ar 1 il_

'J m

HTP-1 wherein the symbols have the following meaning:

Ar 11 is the same or different for different repeating units, a single bond, or a mononuclear or polynuclear aryl group which may be optionally substituted;

Ar 12 is the same for different repeating units or different, is a mononuclear or polynuclear aryl group which may be optionally substituted;

Ar 13 is the same or different for different repeating units, a mononuclear or polynuclear aryl group which may be optionally substituted; is 1, 2 or 3. Especially preferred are repeating units of formula HTP-1, which are selected from the group consisting of units of the formulas HTP-1 A-1 C to HTP:

Figure imgf000054_0001

HTP-1 C wherein the symbols have the following meanings: is the same or different at each occurrence, H, a substituted or unsubstituted aromatic or heteroaromatic group, an alkyl, cycloalkyl, alkoxy, aralkyl, aryloxy, arylthio, alkoxycarbonyl -, silyl, carboxy group, a halogen atom, a cyano group, a nitro group or a hydroxy group; r is 0, 1, 2, 3 or 4 and

5

s is 0, 1, 2, 3, 4 or 5th

among other polymers are preferred hole-transport or

Hole injection properties, comprising at least one of the following repeating unit represented by formula 10 HTP-2

Figure imgf000055_0001
wherein the symbols have the following meaning:

15

T 1 and T 2 are independently selected from thiophene, selenophene, thieno [2,3-b] thiophene, thieno [3,2b] thiophene, dithienothiophene, pyrrole, aniline, which groups may be substituted with one or more R b;

20

R b at each occurrence is independently selected from halogen, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C (= O) NR 0 R 00, -C (= O) X, -C (= O) R 0, -NH 2, -NR ° R 00, -SH, -SR 0, -SOsH, 0 -SO 2 R, -OH, -NO2, -CFs, -SF 5, an optionally substituted silyl, carbyl or hydrocarbyl group having from 1 to 40

Carbon atoms, which may be optionally substituted and may comprise one or more optional heteroatoms;

R ° and R 00 are each independently H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 carbon atoms, which

place

may be optionally substituted and may include one or more optional heteroatoms; Ar 7 and Ar 8 each independently represent a mononuclear or polynuclear aryl or heteroaryl group which may optionally be substituted and may optionally be bound to the 2,3 position of one or two adjacent thiophene or selenophene groups; c and e are independently 0, 1, 2, 3 or 4, wherein 1 <c + e <6, d and f are independently 0, 1, 2, 3 or. 4

Preferred examples of polymers having hole transporting or

Hole injection properties 2007/131582 A1, among others, in WO 2008/009343 A1 and WO described. Preferably, the polymer used as the organic functional material having electron-injection and / or electron transport properties can comprising having structural elements of group 2, units corresponding to the electron-injection and / or electron transport materials that have been described above.

comprise another preferred structural elements of group 2, the electron-injection and / or electron-transport properties are, for example, from pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline,

Quinoxaline and phenazine groups derived, but also groups triarylborane or more O, S or N-containing heterocycles having a low LUMO level. Preferably, these structural elements of group 2 have a LUMO of -2.7 eV less than (relative to vacuum level), particularly preferably of less than -2.8 eV. Preferably, the organic functional material, a polymer is, which comprises structural elements according to group 3 wherein

Structural elements (ie, structural elements of the groups 1 and 2) are connected directly to each other to improve the hole and the electron mobility. Some of these features may serve here as an emitter, the emission colors of the countryside, can be moved, for example, Red or Yellow. Their use is therefore

useful for example for the production of other emission colors, or a broadband emission by polymers which emit blue originally.

Preferably, the polymer used as the organic functional material having light emitting properties can exhibit comprising structural elements of group 4, units corresponding to the emitter materials, which have been detailed above. In this case, polymers with phosphorescent groups are preferred, especially those set forth previously emitting metal complexes which corresponding

Units with elements of group 8 to 10 containing (Ru, Os, Rh, Ir, Pd, Pt).

Preferably, the polymer used as the organic functional material having units of the group 5, which improve the transition from so-called singlet state to the triplet state can, for the support of phosphorescent compounds, the polymers set out above are used with structural elements of group 4 preferably. Here, a triplet polymeric matrix can be used. Suitable for this purpose in particular, carbazole and related carbazole, as described in DE 10304819 A1 and DE 10328627 A1 are described. Also suitable for this purpose are ketone,

Phosphine oxide, sulfoxide, sulfone, silane derivatives and similar

Compounds as described in DE 10349033 A1. Further preferred compounds of structural units may be derived, have been previously described in conjunction with the matrix materials, which are used together with the phosphorescent compounds. Preferably the further organic functional material is a polymer comprising units of the group 6, the morphology and / or

affect the emission color of the polymers. These are in addition to the above polymers, those containing at least one more

aromatic or have another conjugated structure which does not belong to the above-mentioned groups. These groups

Accordingly, only little or no effect on the charge carrier mobilities that are not metal-organic complexes or the singlet-triplet transition.

Such structural units, the morphology and / or

affect emission color of the resultant polymers. Depending on

Structural unit can therefore also be used as emitter these polymers.

In the case of fluorescent OLEDs, therefore, are aromatic

Structural elements having 6 to 40 C atoms or tolan, stilbene or Bisstyrylarylenderivat units, each of which may be substituted with one or more groups. Particularly preferred is the

Use of groups 1, 4-phenylene, 1, 4-naphthylene, 1, 4, or 9,10-anthrylene, 1, 6-, 2,7- or 4,9-Pyrenylen-, 3, 9- or 3,10-Perylenylen-, 4,4'-biphenylene, 4,4 "-Terphenylylen-, 4,4 'bi 1, 1 -Naphthylylen-, 4,4' Tolanylen-, 4,4' -Stilbenylen- or 4,4 "-Bisstyrylarylen- derived derivatives.

Preferably, the polymer used as the organic functional material comprising units of the group 7, which preferably contain aromatic structures having 6 to 40 C atoms, which are widely used as a backbone.

These include 4.5-dihydropyrene, 4,5,9,10- tetrahydropyrene, fluorine derivatives, for example, in US 5962631, WO 2006/052457 A2 and WO 2006/118345 A1 disclosed, 9,9-spirobifluorene derivatives, for example, in WO 2003/020790 A1 are disclosed, 9,10-phenanthrene derivatives, for example, in WO 2005/104264 A1 are disclosed, 9,10-dihydrophenanthrene derivatives, for example, in WO 2005/014689 A2 there are disclosed 5,7-Dihydrodibenzooxepin derivatives and cis- and trans-indenofluorene derivatives, for example, in WO 2004/041901 A1 and WO 2004/113412 are disclosed A2, and binaphthylene derivatives, for example, in WO 2006 / 063 852 A1 are disclosed, and other units, for example, in WO 2005/056633 A1, EP 1344788 A1, WO 2007/043495 A1, WO 2005/033174 A1, WO 2003/099901 A1 and DE

disclosed 1,020,060,037,103th

Particularly preferred structural units of the group 7, which are selected from fluorene derivatives, for example, in US 5,962,631, the

WO 2006/052457 A2 and WO 2006/118345 A1 are set forth;

Spirobifluorene derivatives, for example, in WO 2003/020790 A1 are disclosed; Benzofluoren-, Dibenzofluoren-, benzothiophene, dibenzofluorene groups and derivatives thereof, for example, in WO 2005/056633 A1, EP 1344788 A1 and WO 2007/043495 A1 are disclosed.

Very particularly preferred structural elements of Group 7 will be set forth by the general formula PB-1:

Figure imgf000059_0001

PB-formula 1 wherein the symbols have the following meanings A, B and B 'are each, for different repeating units, the same or different is a divalent group which is preferably

is selected from -CR c R d -, -NR C -, -PR C -, -O-, -S-, -SO-, -SO2-, -CO-, -CS-, -CSe-, -P (= O) R c -, -P (= S) R C - and -SiR c R d -;

R c and R d are at each occurrence independently selected from H,

Halogen, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C (= O) NR 0 R 00, -C (= O) X, -C (= O) R °, -NH 2 , -NR ° R 00, -SH, -SR 0, -SO 3 H, -SO 2 R 0, -OH, -NO 2, -CF 3), -SF 5, an optionally substituted silyl, or carbyl hydrocarbyl group having from 1 to 40 carbon atoms, which may be optionally substituted and may comprise one or more optional heteroatoms wherein the

R c and R d may optionally form a spiro group with a fluorine radical to which they are attached; X is halogen;

R ° and R 00 are each independently H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 carbon atoms which may be optionally substituted and may include one or more optional heteroatoms; g is independently 0 or 1 and h is independently 0 or 1, the sum of g and h 1 preferably is in a subunit; m is an integer> 1;

Ar 1 and Ar 2 each independently represent a mononuclear or polynuclear aryl or heteroaryl group which may optionally be substituted and may optionally be bound to the 7,8-position or 8,9-position by an indenofluorene groups; a and b are independently 0 or 1. If the groups R c and R d form a spiro group with the fluorene group to which these groups are bonded, so, this group preferably is a spirobifluorene.

Particularly preferred repeat units of formula PB-1, which are selected from the group consisting of units of the formulas A to PB-1 PB-1E:

Figure imgf000061_0001

Formula PB-1C

Figure imgf000062_0001

Figure imgf000062_0002

R e is preferably F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C (= O) NR 0 R 00, -C (= 0) X, - C (= O) R °, -NR ° R 00, an optionally substituted silyl, aryl or heteroaryl group having 4 to 40, preferably 6 to 20 carbon atoms, or a linear, branched or cyclic alkyl, alkoxy , alkylcarbonyl, alkoxycarbonyl, or Alkylcarbonlyoxy-

R °, R alkoxycarbonyloxy group with 1 to 20, preferably 1 to 12 C atoms, wherein one or more hydrogen atoms may optionally be substituted by F or Cl, and the groups are as previously set forth for formula PB-1 00, and X ,

Particularly preferred repeat units of formula PB-1, which are selected from the group consisting of units of the formulas F-1 to PB PB-11:

Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0003

Figure imgf000063_0004

Formula PB-11

wherein the symbols have the following meanings: L is H, halogen or an optionally fluorinated, linear or

branched alkyl or alkoxy group having 1 to 12 carbon atoms and is preferably H, F, methyl, i-propyl, t-butyl, n-pentoxy or

trifluoromethyl; and

L 'is an optionally fluorinated, linear or branched alkyl or alkoxy group having 1 to 12 carbon atoms and is preferably n-octyl or n-octyloxy. for carrying out the present invention, polymers having more than one of the structural elements set forth above of the groups 1 to 7 are preferred. Furthermore, it can be provided that the polymers preferably contain more than one of the structural elements set out above from a group, which comprise mixtures of structural elements which are selected from a group.

in particular Particularly preferred are polymers which, in addition to at least one structural element which light emitting characteristics (Group 4), preferably at least one phosphorescent group, additionally at least one further structural element of groups 1 to 3, 5 or 6 set forth above include, these are preferably selected from the groups. 1 to 3

The proportion of different classes of groups, if present in the polymer can be within wide ranges, which are known in the art. Surprising advantages can be achieved in that the proportion of existing in a class of polymers, each of which is selected from the detailed above structural elements of the groups 1 to 7, preferably at least 5 mol%, particularly preferably at least 10 mol%. The manufacture of white-emitting copolymers set forth in detail, among others, in DE 10343606 A1.

To improve the solubility of the polymers may have respective groups. It can preferably be provided that the

polymers having substituents such that on average per

Repeating unit, at least 2 non-aromatic carbon atoms, more preferably at least 4 and most preferably at least 8 non-aromatic carbon atoms are contained, wherein the average to the number average applies. Here, individual carbon atoms may be replaced by O or S, for example. It is possible, however, that a certain fraction, optionally all repeating units having no substituents include the non-aromatic carbon atoms. Here, short-chain substituents are preferred as long-chain substituents can have adverse effects on layers that can be obtained using the organic functional materials. Preferably, the substituents not more than 12

Carbon atoms, preferably at most 8 carbon atoms, and particularly preferably at most 6 carbon atoms in a linear chain.

The polymer used in the invention, as the organic functional material may be a random, alternating or regioregular

Copolymer, a block copolymer or a combination of these

his copolymer forms.

In another embodiment, the polymer used as the organic functional material may be a non-conjugated polymer having

be the side chains, which embodiment is particularly important for phosphorescent OLEDs, which are based on polymers. In general, phosphorescent polymers may be obtained by radical copolymerization of vinyl compounds, said vinyl compounds containing at least one unit with a phosphorescent emitter and / or at least one charge transport unit as, inter alia, in US 7250226 B2 is disclosed. Other phosphorescent polymers are described, inter alia, in JP 2007/211243 A2, JP 2007/197574 A2, the US 7,250,226 B2 and JP 2007/059939 A.

In a further preferred embodiment, the non-conjugated polymers include, on the basis of backbone units represented by

Spacer units are interconnected. Exemplary of such triplet emitters of on non-conjugated polymers based on

Backbone units are based, are set out in DE 102,009,023,154th

In a further preferred embodiment, the non-conjugated polymer may be designed as a fluorescent emitter. Preferred fluorescent emitters with on non-conjugated polymers

based side chains, anthracene include, benzanthracene groups or derivatives of these groups in the side chain, these polymers are set out 2005/08 556, JP 2005/285661 and JP 2003/338375, for example, in JP.

These polymers can be used as electron or hole transport materials in many cases, these polymers being preferably configured as a non-conjugated polymers. The above-cited references describing the functional compounds to be in the present application

Purposes of disclosure incorporated by reference thereto.

The nanoparticles contained in the formulations of this invention may contain any organic functional materials, which are necessary for the production of the respective functional layer of the electronic device. For example, a hole transport, hole injection, electron transport, electron injection layer constructed exactly from a functional link, comprising

Nanoparticles of the formulation used to prepare these functional layer as the organic functional material is precisely this connection. exactly comprises an emission layer, for example, an emitter in combination with a matrix or host material, the nanoparticles of the formulation used to prepare these functional layer include, as the organic functional material, the mixture of emitter and matrix or host material, as in this application elsewhere is set forth in more detail.

The nanoparticles may have different amounts of liquids, particularly solvents, preferably organic solvents have to be removed after application of the formulation to a substrate or one of the subsequently applied to the substrate layers.

These preferred organic solvents can be used for preparing the nanoparticles and / or serve a

Coalescence of the nanoparticles according to facilitate or during the removal of the solvent the continuous phase.

Suitable organic solvents include ketones, esters, amides, sulfur compounds, nitro compounds, halogenated

Hydrocarbons and hydrocarbons.

Aromatic and heteroaromatic hydrocarbons and chlorinated hydrocarbons are preferred organic solvents. Particularly preferred organic solvents are dichloromethane, trichloromethane, monochlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, chloroform, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 1, 1, 1-trichloroethane, 1, 1, 2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide,

Dimethylacetamide, dimethylsulfoxide, tetralin, decalin, indane and / or mixtures of these compounds.

The solvents may be used individually or as a mixture of two, three or more compounds.

Preferably, the nanoparticles comprise in small amounts

Solvents which are difficult to mix with the solvent of the continuous phase. The formulation used for administration is preferably at most 50 wt .-%, particularly preferably at most 30 wt .-%, most preferably at most 20 wt .-%, particularly preferably at most 10 wt .-% and especially preferably at most 5 wt % of solvent, which are sparingly soluble or insoluble in the continuous phase, based on the weight of the

Formulation contained solids. The solids are the materials which after the production of the same remain in the respective layer of the organic device.

The proportion of organic functional material which is used for the production of function layers of electronic devices in the formulation is preferably in the range of 1 to 10% more preferably in the range of 2 to 8%, most preferably in the range of 2.5 to 6 % and particularly preferably in the range of 3 to 5%, based on the total weight of the formulation.

The proportion of surfactant polymer in the formulation is preferably in the range of 0.1 to 5%, particularly preferably in the range of 0.1 to 4%, most preferably in the range of 0.2 to 2% and most preferably in the range of 0.1 to 0.8%, based on the total weight of the formulation. The proportion of the solvent comprising the continuous phase of

forming formulation in the formulation is preferably in the range of 80 to 99.9%, particularly preferably in the range of 85 to 99%, most preferably in the range of 90 to 98% and particularly preferably in the range of 95 to 97%, based on the total weight of the formulation.

Besides the components mentioned, the invention can

Formulation include other additives and processing aids.

These include surface active agents, surfactants, lubricants and lubricant additives which increase the conductivity, dispersing agents, hydrophobizing agent, adhesion promoters, flow improvers, defoaming agents, deaerators, diluents which may be reactive or non-reactive fillers, additives, processing aids, dyes, pigments, stabilizers, sensitizers, nanoparticles, and inhibitors.

Surprisingly shows the formulation even without the addition of large amounts of processing aids or other additives which do not exert the functions set out above in an electronic device excellent in application capability. Therefore, a formulation comprises in a preferred aspect of the present invention preferably at most 30 wt .-%, particularly preferably at most 15 wt .-%, most preferably at most 5 wt .-%, particularly preferably at most 1 wt .-% and very especially preferably at most 0.5 wt .-% of additives, e.g.

Processing aids, no functional effect in the

have electronic devices of the present invention and not to those set forth previously surfactant polymers, polysaccharides, and / or are preferably polypeptides.

The continuous phase may in addition to the detailed above

Solvents and the surfactant polymers contain further additives, as described above, and preferably small amounts are present of additives. Preferably, it can be provided that the continuous phase comprises at least 80 wt .-%, more preferably at least 90 wt .-%, very particularly preferably comprises at least 95 wt .-% and especially preferably at least 97 wt .-% of solvent, based on the weight of the continuous phase.

The preparation of the formulation may be made by procedures which are disclosed inter alia in US 2009/081357 A1 and WO 2011/076314 A1 in the.

Another object of the present invention is a process for preparing a formulation according to the invention comprising the

Steps: a) preparing a first composition comprising a first solvent;

Preparing a second composition comprising a second solvent, wherein the second composition comprises at least one organic functional material for the preparation of

Functional layers of electronic devices can be used, comprising;

Mixing the mixture obtained in step a) the first composition and the compound obtained in step b) the second composition in an intended ratio;

preparing a formulation obtained from the step c)

Mixture by a physical method. The formulation obtained by this process may be referred to as an emulsion, if the second solvent in the first solvent is sparingly soluble or insoluble. From the obtained emulsion, a dispersion can be obtained by removal of the second solvent which is sparingly soluble or insoluble in the first solvent, from the formulation.

Water and / or the alcohols set forth above having 1 to 6

Carbon atoms are preferred first solvent for the first

Composition.

The second solvent is generally an organic

Solvents are, which is difficult to mix with the first solvent. Examples have been mentioned above.

The mixing ratio of the first and the second composition in step c) is not particularly limited. Preferably, it can be provided that the weight ratio of the first

Composition to the second composition ranges from 1: 1 to 50: 1, more preferably in the range from 3: 1 to 15: 1 and most preferably in the range of 5: 1 to 10: 1.

Preparing a dispersion and / or an emulsion in accordance with step d) can be effected by known means. These include in particular mechanical methods such as high pressure homogenization or jet dispersers, and the application of ultrasound, the use of ultrasound is preferred.

To prepare the first and / or the second composition, a surfactant may be added. According to a preferred embodiment, the content of surfactants can be kept very low, however, wherein more preferably no surfactant is added. The proportion of surfactants is preferably at most 20 wt .-%, particularly preferably at most 10 wt .-%, most preferably at most 5 wt .-% and especially preferably at most 1 wt .-%, based on the weight of the respective composition. No surfactants are particularly preferably used, so that the compositions and / or the formulation comprising no significant levels of surfactants, wherein the proportion by weight, preferably .-%, particularly preferably at most 0.1 wt .-%, most preferably at most 0.5 at most 0.05 wt .-% and especially preferably at most 0.01 wt .-%, based on the weight of the respective composition or formulation weight.

Surfactants here surfactants with a low

Molecular weight. Suitable surfactants include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, or mixtures of these surfactants.

Preferred classes of nonionic surfactants are:

Polyethylene oxide condensates of alkyl phenols, for example,

Condensation products of alkyl phenols having an alkyl group containing from about 6 to about 20 carbon atoms which may be straight or branched, with ethylene oxide, said ethylene oxide being present in amounts equal to from about 10 to about 60 moles of ethylene oxide per mole of alkylphenol; nonionic surfactants derived from the condensation of ethylene oxide with the product resulting from the reaction of

Propylene oxide and ethylene diamine was obtained;

3) condensation products of aliphatic alcohols having from about 8 to about 18 carbon atoms, which may be straight or branched, with ethylene oxide, for example. For example, a coconut alcohol ethylene oxide condensate having from about 10 to about 30 moles of ethylene oxide per mole

Coconut alcohol, the coconut alcohol fraction comprises about 10 to about 14 carbon atoms; 4) long chain tertiary amine oxides;

5) long chain tertiary phosphine oxides;

6) long chain dialkyl sulfoxides containing one short chain alkyl or

Hydroxyalkyl radical having about 1 to about 3 carbon atoms

(Usually methyl) and one long hydrophobic chain which may be formed by alkyl, hydroxy alkyl, or keto alkyl radicals containing from about 8 to about 20 carbon atoms that may contain 0 to about 10 ethylene oxide moieties and from 0 to about 1 glyceryl moiety;

7) alkyl polysaccharide (APS) surfactants such as the Alkylpolyglyco pages, as described in US 4,565,647, having a hydrophobic group with about 6 to about 30 carbon atoms and a polysaccharide group (z. B. polyglycoside) as the hydrophilic group, and optionally may comprises a polyalkylene oxide group, the alkyl group (ie, the hydrophobic moiety) saturated or unsaturated, branched or unbranched, and unsubstituted or substituted (e.g., with hydroxy or cyclic rings). his; and 8) polyethylene glycol (PEG) -Glycerylfettsäureester such as those of formula R (O) OCH 2 CH (OH) CH 2 (OCH 2 CH 2) n OH wherein n is from about 5 to about 200, preferably about 20 to about 100, and R is an aliphatic

represents hydrocarbon having from about 8 to about 20 carbon atoms.

Other methods for the preparation of dispersions and / or emulsions are disclosed in US 2009/081357 A1, which is incorporated into the present application for purposes of disclosure. Thus, a dispersion can, among other things directly through the use of

Colloid mills are produced.

A formulation according to the present invention can be used to produce a layer or multi-layer structure in which the organic functional materials are present in layers, as they are needed for the preparation of the preferred electronic or optoelectronic devices such as OLEDs. For further processing it is sometimes advantageous, the second solvent, optionally present as a mixture of one or more

to remove discontinuous phases of the formulation prior to application of the formulation. Preferably may thus be provided to convert an emulsion initially obtained into a dispersion. The nano droplets of the emulsion according to the present invention can be converted by removing the second organic solvent in solid nanoparticles in the continuous phase (s) of the formulation are dispersed. The term dispersion herein refers to a system comprising

at least one liquid medium (preferably an aqueous and / or alcoholic phase) and an organic phase which is formed by suspended solid particles, preferably as nanoparticles. The formulation of the present invention can be preferably used for

Formation of functional layers on a substrate or of layers applied to the substrate can be used.

A method for manufacturing an electronic device in which a formulation of the invention is applied to a substrate and dried, is also subject of the present invention. The generation of the functional layers, for example, by flow coating, dip coating, spray coating, spin coating, screen printing, relief printing, intaglio printing, rotary printing, roll coating, flexographic printing, offset printing or nozzle printing, preferably ink-jet printing on a substrate or the deposited onto the substrate layers done.

After application of a formulation according to the invention to a substrate or an already applied functional layer may be a

carried drying step to remove the solvent of the detailed above continuous phase. Preferably, the drying can be effected at a relatively low temperature and over a relatively large period of time, to avoid bubble formation and to obtain a uniform coating. Preferably, the drying at a temperature in the range of 10 to 60 ° C, particularly preferably in the range of 15 to 55 ° C and very particularly preferably be carried out in the range of 20 to 30 ° C. Here, the drying may preferably be at a pressure in the range of 10 "3 mbar to 2 bar, particularly preferably in the range of 10" 2 mbar to 1 bar and especially preferably in the range of 10 "1 mbar to 100 mbar carried out. The duration of the drying depends on the degree of drying to be reached, with small amounts of water may be removed, optionally at a higher temperature and in connection with a preferably carried out sintering. Further, it can be provided that after the drying of the

Substrate coated layer, which contained in the nanoparticle comprises organic functional material, a sintering step is performed. Preferably, the sintering step may be carried out at a temperature in the range of 75 to 220 ° C, more preferably in the range of 100 to 150 ° C and most preferably in the range of 125 to 150 ° C. The sintering may preferably over a period ranging from 1 minute to 10 hours, more preferably in the range of 10 minutes to 4 hours, most preferably in the range of 20 minutes to 3 hours, and more preferably in the range of 30 minutes to 1 hour become. Further, it can be provided that the method is repeated several times, with different or identical functional layers are formed.

The present invention is also an electronic

Device obtainable by a process for producing an electronic device.

Another object of the present invention is an electronic device having at least one functional layer comprising at least one organic functional material and at least one interface-active polymer, preferably selected from polysaccharides and / or polypeptides.

Under an electronic device, a device is understood, which anode, cathode and at least one intermediate

contains functional layer, said function layer contains at least one organic or organometallic compound.

The organic electronic device is preferably an organic electroluminescent device (OLED), a polymeric electroluminescent device (PLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic, light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic, optical detector, an organic photoreceptor, an organic field-quench device (O-FQD) an organic electric sensor, a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser). Active components are generally the organic or inorganic materials which are introduced between the anode and cathode, said active components, the properties of the electronic

Device, for example, their performance and / or their service life cause maintain and / or improve, for example, charge-injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials. The organic functional material which is used for the production of function layers of electronic devices, thus preferably comprises an active component of

electronic device.

A preferred embodiment of the invention, luminescence devices, organic electronics. The organic electroluminescent device comprises a cathode, anode and at least one emitting layer.

It is further preferred to use a mixture of two or more triplet emitters together with a matrix. Here, the triplet emitter connected to the shorter wavelength emission spectrum is used as a co-matrix for the triplet emitter with the longer wavelength emission spectrum.

The proportion of the matrix material in the emitting layer in this case is 50.0 to 99.9 vol .-%, preferably 80.0 to 99.5 vol .-%, and more preferably for fluorescent emitting layers between 92.0 and 99.5 vol .-%, and for phosphorescent emissive layers 85.0 to 97.0 vol .-%.

Correspondingly, the proportion of the dopant is between 0.1 and

50.0 Vol .-%, preferably 0.5 to 20.0 vol .-%, and more preferably for fluorescent emitting layers 0.5 to 8.0 vol .-%, and for phosphorescent emitting layers between 3.0 and 15.0 vol .-%. An emitting layer of an organic electroluminescent device may also include systems comprising a plurality of matrix materials (mixed-matrix systems) and / or more dopants. Also in this case, the dopants are generally those materials whose share in

System is the smaller and the matrix materials are those

Materials whose content is the larger in the system. In individual cases, however, the proportion of a single matrix material in the system can be smaller than the proportion of a single dopant.

The mixed matrix systems comprise preferably two or three

various matrix materials, particularly preferably two different matrix materials. Preferred in this context is one of the two materials, a material having hole-transporting properties and the other material, a material having electron-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed-matrix components may also be primarily or entirely in a single mixed-matrix component combined be, the further or the further mixed-matrix components fulfill other functions. The two different matrix materials can be present in a ratio of 1: 50 to 1: 1, preferably 1: 20 to 1: 1, more preferably 1: 10 to 1: 1, and most preferably from 1: 4 to 1: 1. Mixed Matrix systems are preferably used in devices phosphorescent organic electroluminescence. More detailed information on mixed-matrix systems are included, among others, in WO 2010/108579.

In addition to these layers, an organic electroluminescent device may also comprise further layers, for example in each case one or more hole-injection layers, hole transport layers,

Hole blocking layers, electron transport layers, electron injection layers, Exzitonenblockierschichten, Elektronenblockier- layers, charge generating layers and / or organic or inorganic p / n junctions. It is possible that one or more hole transport layers are p-doped, for example with

Metal oxides, such as M0O3 or WO3 or with (per) fluorinated electron-deficient aromatics, and / or that one or more electron-transfer transport layers are n-doped. Similarly, emitting between two layers of interlayer can be introduced, which for example, a

have exciton blocking function and / or control the charge balance in the electroluminescent device. but it was reported hinge that each of these layers must necessarily be present.

The present invention is thus also a layer, particularly an organic layer containing one or more surface-active polymers, as defined above.

In a further embodiment of the present invention, the device comprises multiple layers. The formulation of the invention can thereby be preferably used for producing a hole transport, hole injection, electron transport, electron injection and / or emission layer.

The present invention accordingly also relates to an electronic device comprising at least three, in a preferred embodiment, however, all said layers of the hole injection,

Hole-transport, emission, electron transport, electron injection, charge blocking, and / or charge generating layer contains, and was obtained in the at least one layer by a use in accordance with the invention formulation. The thickness of the layers, for example of the hole-transport and / or hole-injection layer may preferably be in

Range of 1 to 500 nm, more preferably, in the range of 2 to 200 nm. The apparatus may further include layers, which are constructed from other low molecular weight compounds or polymers, the formulations not according to the invention by the use of

were applied. This can also by evaporating

low molecular weight compounds are generated in a high vacuum.

It may also be preferred, the compounds to be employed not as pure substance, but as a mixture (blend) together with further polymeric, oligomeric, dendritic or low-molecular

to use substances. This can for example, improve the electronic properties or emit themselves.

In a preferred embodiment of the present invention, formulations of the invention, organic functional materials, which are used as host materials or matrix materials in an emitting layer include. Here, the formulation may additionally comprise the host materials or matrix materials set forth above, the emitter. In this case, the organic electroluminescence zenzvorrichtung contain one or more emitting layers, wherein at least one emitting layer contains at least one compound of the invention as defined above. If a plurality of emission layers are present, they preferably have a plurality of emission maxima between 380 nm and 750 nm, resulting overall in white emission, ie in the emitting layers emitting different compounds are used, which fluoresce or phosphoresce. Most particularly preferred are three-layer systems, where the three layers exhibit blue, green and orange or red emission (for the basic structure, see for example WO 05/011013). White-emitting devices are suitable for example as backlighting of LCD displays or for general lighting applications. In addition to these layers, the organic Elektrolumineszenzvor- can contain direction further layers, for example in each case one or more hole-injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton-blocking layers and / or charge generation layers

(Charge generation layer, IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, multiphoton Organic EL Device having charge generation layer). Likewise, between two emitting layers of interlayer can be introduced einge- having, for example, an exciton-blocking function. It should be pointed out that not necessarily each of these layers must be present. These layers can also be obtained using the formulations of the invention as defined above. It is also possible that a plurality of OLEDs are arranged one above the other, whereby a further increase in efficiency can be achieved in terms of luminous efficiency. For improving the light outcoupling the final organic layer may be on the

Light outgoing side to be executed in OLEDs, for example, as a nano-foam, whereby the proportion of the total reflection is reduced.

Further preferred is an organic electroluminescent device, wherein one or more layers are applied by a sublimation process. The materials are applied in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10 -6 mbar, evaporated particularly preferably less than 10 7 mbar.

Further, provided that one or more layers of an electronic device according to the invention with the OVPD (organic vapor phase deposition) process or with the aid of a

Carrier-coated. The materials at a pressure between 10 "5 mbar and 1 are applied bar. Further, provided that one or more layers of an electronic device of the invention from solution such as by spin coating, or by any printing method such as screen printing, flexography or offset printing, but particularly preferably LITI (light induced thermal imaging, thermal transfer printing) or ink-jet printing

(Jet pressure) can be produced.

The apparatus typically includes a cathode and an anode

(Electrodes). The electrodes (cathode, anode) are selected in accordance with the present invention is that its energy band match as well as possible with those of the adjacent organic layers, in order to ensure efficient electron or hole injection.

As a cathode are metal complexes, preferably metals having a low work function metal alloys or multilayer structures made of various metals, such as alkaline earth metals, alkali metals,

Main group metals, or lanthanides (for example, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). In multilayered structures, further metals may also in addition to the said metals are used, which have a relatively high work function, such as Ag, in which case usually combinations of the metals, such as Ca / Ag or Ba / Ag

be used. It may also be preferred, between a

metallic cathode and the organic semiconductor, a thin

introducing the intermediate layer a material having a high dielectric constant. For this purpose are, for example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides in question (eg LiF, u2o, BaF2, MgO, NaF, etc.). The layer thickness of this layer is preferably between 0.1 and 10 nm, particularly preferably between 0.2 and 8 nm, and most preferably between 0.5 and 5 nm.

Suitable anode materials are preferred high work function. Preferably, the anode has a potential greater than 4.5 eV vs. Vacuo. For this purpose, metals are on the one hand suitable high redox potential, such as Ag, Pt or Au. It may on the other hand (AI / Ni / NiO, Al / PtOx for example) may be preferred, metal / metal oxide electrodes. For some

Applications must be transparent at least one of the electrodes to enable either the irradiation of the organic material (O-SC) or the extraction of light (OLED / PLED, O-laser). A preferred construction uses a transparent anode. Preferred anode materials include conductive metal oxides mixed here. Particularly preferably, indium tin oxide (ITO) or indium zinc oxide (IZO).

conductive, doped organic materials, in particular conductive doped polymers, such as poly (ethylenedioxy-thiophene) (PEDOT), and polyaniline are also preferred (PANI), or derivatives of these polymers. Preference is given to continue when a p-doped to the anode

Hole transport material is applied as a hole injection layer, which are suitable as a p-dopant metal oxides, such as M0O3 or WO3, or (per) fluorinated electron-deficient aromatics. Other suitable dopants are p-HAT-CN (hexacyano hexaazatriphenylene) or

Connection NPD9 Novaled. Such a layer simplifies the

Hole injection into materials with a deep HOMO, so a

magnitude large HOMO.

In the other layers generally all materials can be used, as they are used according to the prior art, for the layers, and the skilled artisan can combine with the inventive materials without inventive step each of these materials in an electronic device.

The device is in a known manner depending on the application appropriately patterned contacts and finally hermetically sealed, since the lifetime of such devices is the presence of water and / or air drastically shortened. Another object of the present invention is the use of polysaccharides and / or polypeptides for the preparation of

electronic devices. The formulations according to the invention, the available therefrom

electronic devices, especially organic luminescence devices electrical, are characterized by one or more of the following surprising advantages over the prior art: 1. The formulations of the invention can be applied to already

Muster applied functional coatings without the

Properties of these already existed before the application of the formulation functional layers are affected. A uniform coating obtained although the in: Here

Formulation solvent contained in many cases a very high

having surface tension.

The formulations according to the invention can also be applied

apply functional layers, by applying the self-

Formulations were obtained according to the present invention without entering an impairment of these functional layers. This allows in principle all functional layers of a

electronic device by the application of

Formulations of the invention are obtained.

The available with the novel formulations electronic devices exhibit very high stability and very high life compared to electronic

Devices which were obtained with conventional methods. It should be noted that the aforementioned

Sublimationsmethoden be carried out at relatively high temperatures, so that when entering and low decomposition of the functional materials. The use of high levels of surfactants can lead to a reduction in the performance of the functional materials. The use of orthogonal solvents limits the range of functional materials so that optimal electronic devices can be relatively difficult to obtain in this way. Furthermore, cross-linking

Groups have an adverse effect on the life and performance of electronic obtainable therefrom

have devices.

4. The formulations according to the invention can be economically produced and processed as water and / or acceptable alcohols as solvents and / or dispersants can be used. An elaborate processing of large amounts of

environmentally hazardous organic solvents is not necessary to practice the present invention.

5. The formulations according to the invention can be processed by conventional methods, so that thereby cost advantages can be achieved.

6. The employed in the novel formulations

organic functional materials are not subject to particular limitations, so that the method of the present invention can be used extensively.

These above-mentioned advantages are not accompanied by an impairment of the other electronic properties.

It should be noted that variations of the embodiments described in the present application are within the scope of this invention. Each feature disclosed in the present invention may feature, unless this is explicitly excluded, be replaced by alternative features the same, serve an equivalent or similar purpose. Thus, any disclosed in the present application feature, unless otherwise stated, to be regarded as an example of a generic series or equivalent or similar feature.

All features of the present invention may be combined in any way with each other, unless that certain features and / or steps are mutually exclusive. This is particularly true for preferred features of the present invention. Similarly, features can non-essential combinations may be used separately (not in combination). It should also be noted that many of the features, and in particular that of the preferred embodiments of the present invention should not be considered itself inventive and only as part of the embodiments of the present invention. For these features, an independent protection can be sought at any presently claimed invention additionally or alternatively.

The disclosed with the present invention for technical actions can be combined with abstracts and other examples. The invention is explained in more detail below with reference to exemplary examples, without being restricted thereby.

One skilled in the art can prepare from the descriptions without inventive step further electronic devices according to the invention, and thus carry out the invention throughout the range claimed. Examples

Example 1 For the disperse phase of the low-molecular hybrid particles 50 each mg of material consisting of a mixture of host and guest molecules were added to 3 g of toluene.

Solution 1 contains 40 mg of a matrix material M1 and 10 mg of an emitter E1 in 3 ml of toluene.

Solution 2 contains 20 mg of a matrix material M2, 20 mg of

M3 matrix material and 10 mg of an emitter E2 in 3 ml of toluene. The structural formulas of matrix materials and emitters used are shown below:

Figure imgf000087_0001

M1 M2

M3

Figure imgf000088_0001

Both systems were completely dissolved with stirring at 60 ° C within 1 hour. The continuous phase consisted of both

Material systems from a fresh solution of 7.5 mg SDS in 8 g MilliQ- water.

The further manufacturing process was identical for all

Dispersions. The disperse phase and the surfactant solution were combined and the mixture sealed pre-emulsified at room temperature for at least 1 hour at 1200 r / min. From the pre-emulsion directly followed by a mini-emulsion (70% amplitude, 180 s sound time, always 10 s pulse and 10 s pause Branson Sonifier W450, 1 /-inch tip) was determined by homogenization in a ultrasonic tip made. The sample vessel was cooled in an ice bath during the scarf Lens. Thereafter, the mini-emulsion at 65 ° C and 700 rev / min stirring in an oil bath open to evaporate organic solvent. After 12 to 15 hours purely aqueous dispersion was still about 5 ml left and the sample volume was further concentrated according to need, so that a certain

Solids content (typically 1 to 3%) was obtained. To remove excess surfactant, the cooled finished dispersion, if necessary in a dialysis tube was (Visking tubes, MWCO 14000 g / mol, Carl Roth) dialyzed in 2 L of MilliQ water. The duration of dialysis was dependent on the type and amount of surfactant and were dispersions with various degrees of dialysis used for OLED manufacturing. A complete dialysis of a standardized approach took about 12 hours.

Coating of nanoparticles with polysaccharides.

5

example 2

The nanoparticles were coated with polysaccharide by for 12 hours in an aqueous solution of 0.02 to 0.1% xyloglucan (from tamarind resin, molecular weight about 50 KDa) were stirred. Excess ^ Q polysaccharide was removed by centrifugation and decanting.

example 3

The nanoparticles were coated with polysaccharide by for 12 hours in an aqueous 0.02 to 0.1% solution of Gaiactomannan (g of guar gum, molecular weight about 25 KDa) were stirred. An excess of polysaccharide was removed by centrifugation and decanting.

example 4

Plot of polysaccharide-coated nanoparticles on glass substrates (for example 2 and 3).

The obtained dispersion was coated on a HIL-coated glass substrate by spin coating, and an emission layer was obtained with a layer thickness of 80 to 140 nm. The layer was dried at 150 ° C for 60 minutes and then sintered for 60 minutes at 180 ° C. It has a layer having a surface energy of 16 mN / receive (The contact angle of the layer were 81.6 (L) 83.2 ()) - 0

Claims

claims
Formulation containing at least one solvent and
Nanoparticles comprising at least one surfactant and at least one polymer organic functional material which is used for the production of function layers of electronic devices.
A formulation according to claim 1, characterized in that the organic functional material for the preparation of
is used functional layers of electronic devices is selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, materials Excitonenblockiermaterialien, Elektroneiitransport-, electron injection materials, hole transport materials, hole injection materials, n-type dopant, Wide-band gap materials, electron blocking materials, hole-blocking materials and
Colorants.
The formulation of claim 1 or 2, characterized in that the surfactant polymer having a solubility in water at 25 ° C of at least 1 g / l.
Formulation according to one or more of claims 1 to 3, characterized in that the surface-active polymer has a weight average molecular weight Mw in the range of 5,000 to 1,000,000 g / mol, preferably in the range of 10,000 to 500,000 g / mol and more preferably in the range from 15000 has to 100,000 g / mol. Formulation according to one or more of claims 1 to 4, characterized in that the surface-active polymer has a surface tension in the range of 40 to 60 mN / m.
Formulation according to one or more of claims 1 to 5, characterized in that the surface active polymer having substantially no carboxyl groups.
Formulation according to one or more of claims 1 to 6, characterized in that the surface active polymer is a polysaccharide and / or a polypeptide.
A formulation according to claim 7, characterized in that the polysaccharide is branched.
Formulation according to one or more of claims 1 to 8, characterized in that the surfactant polymer, preferably is a Speicherpolysaccharid a system based on glucose, mannose, fructose, galactose and / or xylose polysaccharide, which is preferably selected from xyloglucans and / or galactomannans.
Formulation according to one or more of claims 1 to 9, characterized in that the weight ratio of organic functional material to surfactant polymer in the range from 1: 1 to 50: 1, preferably in the range of 4: 1 to 12: 1 and particularly preferably in the range of 6: 1 to 8: 1.
A formulation according to one or more of claims 1 to 10, characterized in that the solvent is a polar solvent, wherein the solvent is preferably an ET (30) value of at least 180, preferably of at least 200 kJ / mol, measured at 25 ° C according to C. Reichardt, Angew. Chem., 91, 119 (1979).
Formulation according to one or more of claims 1 to 11, characterized in that the solvent is water and / or an alcohol having at most 6 carbon atoms includes.
Formulation according to one or more of claims 1 to 12, characterized in that the solvent comprises at least 80 wt .-% water and / or an alcohol having at most 6
includes atoms of carbon.
A process for producing an electronic device comprising applying a formulation according to one or more of claims 1 to 13 to a substrate and / or to an indirectly onto a substrate or directly applied layer.
A method according to claim 14, characterized in that the formulation ichtung by Flutbesch, dip coating,
Spray coating, spin coating, screen printing, relief printing, intaglio printing, rotary printing, roll coating, flexographic printing, offset printing or nozzle printing, preferably ink-jet printing on a substrate or of layers applied to the substrate is applied.
The method of claim 14 or 15, characterized in that comprises, after drying the coating applied to the substrate layer that the nanoparticles according to one or more of claims 1 to 13, a sintering step is performed.
Method according to one or more of claims 14 to 16, characterized in that the method is repeated several times, with different or identical functional layers are formed.
Electronic device obtainable by a process according to one or more of claims 14 to 17th
An electronic device having at least one layer comprising at least one organic functional material and at least one surfactant polymer preferably selected from
Polysaccharides and / or polypeptides.
Electronic device according to claim 18 or 19, characterized in that the electronic device is selected devices from the group consisting of organic electroluminescent, optical organic integrated circuits, organic field-effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, organic detectors, organic photoreceptors, organic field-quench devices, light emitting
electrochemical cells or organic laser diodes.
Use of polysaccharides and / or polypeptides for
Manufacture of electronic devices.
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WO2019002183A1 (en) 2017-06-26 2019-01-03 Merck Patent Gmbh Method for producing substituted nitrogen-containing heterocycles

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