DE102014117011B4 - Process for the production of an organic light-emitting component - Google Patents

Abstract

A method for producing an organic light-emitting component with the method steps A) forming a first organic functional layer stack (30) on a first electrode (20), B) forming a charge carrier generating layer stack (40) on the first organic functional layer stack (30), C) forming a second organic functional layer stack (50) on the charge carrier generation layer stack (40), D) arranging a second electrode (60) on the second organic functional layer stack (50), method step B) comprising the following method steps: B1 ) Forming a first electron-transporting layer (41) andB2) Forming a first hole-transporting layer (42), process step B1) comprising the following process steps: B11) applying a first electron-transporting matrix material and a first n-type dopant to the first organic functional layer stack l (30) and B13) crosslinking of the first n-dopant with the first electron-transporting matrix material, and / or wherein- method step B2) comprises the following method steps: B21) application of a first hole-transporting matrix material and a first p-dopant on the first organic functional layer stack ( 30) andB23) crosslinking the first p-type dopant with the first hole-transporting matrix material, and wherein the first n-type dopant is a cesium salt having at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups .

Description

A method for producing an organic light-emitting component is specified.

Organic electroluminescent elements are disclosed in the following documents: US 2012/0193619 A1 , US 2009/0032807 A1 and DE 102010006377 A1 .

Organic light-emitting components, such as organic light-emitting diodes (OLED), usually have at least one electroluminescent organic layer between two electrodes, which are designed as an anode and cathode and by means of which charge carriers, i.e. electrons and holes, are injected into the electroluminescent organic layer can be. Highly efficient and long-lasting OLEDs can be produced by means of conductivity doping through the use of a p-i-n junction analogous to conventional inorganic light-emitting diodes. The charge carriers, i.e. the holes and electrons, are injected from the p- and n-doped layers in a targeted manner into the intrinsically formed electroluminescent layer, where they form excitons that lead to the emission of a photon in the event of radiative recombination. The higher the injected current, the higher the emitted luminance. But the stress also increases with current and luminance, which shortens the life of the OLED. In order to increase the luminance and extend the service life, several OLEDs can be stacked monolithically on top of one another to form so-called stacked OLEDs, whereby they are electrically connected by charge generation layers (CGL). A CGL consists, for example, of a highly doped p-n junction that serves as a tunnel junction between the stacked emission layers. A prerequisite for the use of a CGL in, for example, a white OLED is a simple structure, i.e. a few layers that are easy to process, and the highest possible transmission in the spectral range emitted by the OLED, so that absorption losses of the emitted light are avoided. Conventional stacked OLEDs with CGLs composed of an n- and a p-doped layer have very short lifetimes, since the n-dopants diffuse from the n-doped layer into the p-doped layer and the p-dopants from the p-doped layer diffuse into the n-doped layer. This diffusion takes place more intensely when the OLEDs are exposed to higher temperatures. So far, this problem has been solved, for example, by an intermediate layer as a diffusion barrier between the n- and p-doped layer. However, these intermediate layers often have the disadvantage of a relatively high absorption, which has a negative impact on the efficiency of the stacked OLED. These intermediate layers also impair the off-state appearance of an OLED. In addition, the intermediate layers are often only thermally stable to a very limited extent, which makes it impossible to use these OLEDs at temperatures above 80 ° C.

The object of the present invention is to specify a method for producing an organic light-emitting component.

This object is achieved by a method according to the main claim. Advantageous embodiments and developments of this method are characterized in the dependent claims and are furthermore evident from the following description and the drawings.

An organic light-emitting component is specified which has a first electrode, a first organic functional layer stack on the first electrode, a charge carrier generation layer stack on the first organic functional layer stack, a second organic functional layer stack on the charge carrier generation layer stack, and a second electrode having on the second organic functional layer stack. The charge carrier generation layer stack has at least a first electron-transporting layer and a first hole-transporting layer. The first electron-transporting layer comprises a first electron-transporting matrix material and a first n-dopant, wherein the first n-dopant is covalently bonded to the first electron-transporting matrix material and / or the first hole-transporting layer comprises a first hole-transporting matrix material and a first p-dopant, wherein the first p-type dopant is covalently bound to the first hole-transporting matrix material.

In one embodiment, the first electron-transporting layer is produced by crosslinking the first electron-transporting matrix material and the first n-type dopant and / or the first hole-transporting layer is produced by crosslinking the first hole-transporting matrix material and the first p-type dopant.

The crosslinking is an intermolecular crosslinking of a first hole-transporting matrix material and a first p-dopant and / or an intermolecular crosslinking of a first electron-transporting matrix material and a first n-type dopant. As a result of the crosslinking, the first n-dopant is covalently bound to the first electron-transporting matrix material and / or the first p-dopant is covalently bound to the first hole-transporting matrix material. In the first electron-transporting layer and / or in the first hole-transporting layer there are no or almost no molecules of the first n-dopant and / or of the first p-dopant that are not bound to the first electron-transporting matrix material and / or to the first hole-transporting matrix material are.

Here and below, “on” with regard to the arrangement of the layers and layer stacks means a basic sequence and is to be understood as meaning that a first layer is either arranged on a second layer in such a way that the layers have a common interface, ie in direct mechanical terms and / or are in electrical contact with one another, or that further layers are arranged between the first layer and the second layer.

The organic functional layer stacks can each have layers with organic polymers, organic oligomers, organic monomers, organic small, non-polymeric molecules (“small molecules”) or combinations thereof. Furthermore, they can have at least one organic light-emitting layer. Suitable materials for the organic light-emitting layer are materials which emit radiation due to fluorescence or phosphorescence, for example Ir or Pt complexes, polyfluorene, polythiophene or polyphenylene or derivatives, compounds, mixtures or copolymers thereof. The organic functional layer stacks can furthermore each have a functional layer which is designed as a hole transport layer in order to enable an effective hole injection into the at least one light-emitting layer. The organic functional layer stacks can furthermore each have a functional layer which is designed as an electron transport layer. In addition, the organic functional layer stacks can also have electron and / or hole blocking layers. Materials for the hole transport layers, the electron transport layers and the electron and / or hole blocking layers are known to the person skilled in the art.

In one embodiment, the component comprises a substrate. The first electrode can be arranged on the substrate. The substrate can for example have one or more materials in the form of a layer, a plate, a film or a laminate, which are selected from glass, quartz, plastic, metal and silicon wafer. The substrate particularly preferably has glass, for example in the form of a glass layer, glass film or glass plate, or it consists of it.

The two electrodes, between which the organic functional layer stacks are arranged, can both be designed to be translucent, for example, so that the light generated in the at least one light-emitting layer between the two electrodes goes in both directions, i.e. in the direction of the substrate as well as in that of the substrate remote direction, can be emitted. Furthermore, for example, all layers of the organic light-emitting component can be designed to be translucent, so that the organic light-emitting component forms a translucent and in particular a transparent OLED. In addition, it can also be possible for one of the two electrodes between which the organic functional layer stacks are arranged to be non-translucent and preferably reflective, so that the light generated in the at least one light-emitting layer between the two electrodes only passes in one direction the translucent electrode can be radiated. If the electrode arranged on the substrate is translucent and the substrate is also made translucent, then one speaks of a so-called bottom emitter, while in the case that the electrode arranged facing away from the substrate is made translucent, one speaks of a so-called “top” emitter ”speaks.

The first and the second electrode can independently of one another have a material which is selected from a group comprising metals, electrically conductive polymers, transition metal oxides and conductive transparent oxides (transparent conductive oxide, TCO). The electrodes can also be layer stacks of several layers of the same or different metals or the same or different TCOs.

Suitable metals are, for example, Ag, Pt, Au, Mg, Al, Ba, In, Ca, Sm or Li, as well as compounds, combinations or alloys thereof.

Transparent conductive oxides (“TCO” for short) are transparent, conductive materials, usually metal oxides, such as zinc oxide, tin oxide, cadmium oxide, titanium oxide, indium oxide or indium tin oxide (ITO). In addition to binary metal oxygen compounds, such as ZnO, SnO ₂ or In2O _{3 also} belong to the group of ternary metal oxygen compounds such as Zn ₂ SnO ₄ , CdSnO ₃ , ZnSnO ₃ , MgIn ₂ O ₄ , GaInO ₃ , Zn ₂ In ₂ O ₅ or In4Sn ₃ O ₁₂ or mixtures of different transparent conductive oxides TCOs. Furthermore, the TCOs do not necessarily correspond to a stoichiometric composition and can also be p- or n-doped.

The organic functional layer stacks of the organic light-emitting component described here furthermore have a charge carrier generation layer stack immediately adjacent. A “charge carrier generation layer stack” is used here and below to describe a layer sequence which is designed as a tunnel junction and which is formed by a p-n junction. The charge generation layer stack, which can also be referred to as the so-called “charge generation layer” (CGL), is designed in particular as a tunnel junction that can be used for effective charge separation and thus for “generation” of charge carriers for the adjacent layers.

For example, the charge carrier generation layer stack can directly adjoin the organic functional layer stack.

In one embodiment, the first electron-transporting layer is produced by crosslinking a first electron-transporting matrix material and a first n-type dopant. The first n-type dopant has at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups. The crosslinking takes place via the at least one functional group of the n-dopant.

In one embodiment, the first hole-transporting layer is produced by crosslinking a first hole-transporting matrix material and a first p-type dopant. The first p-type dopant has at least one functional group selected from a group including oxetane, epoxy and acrylic groups. The crosslinking takes place via the at least one functional group of the p-dopant.

In a first electron-transporting layer produced by crosslinking the first electron-transporting matrix material with the first n-dopant and / or in a first hole-transporting layer produced by crosslinking the first hole-transporting matrix material with the first p-dopant, the dopants are firmly integrated in the respective layer and are thus immobilized. Diffusion of the first p-dopant and the first n-dopant into adjacent layers is thus prevented. This increases the service life of the organic light-emitting component, since a constant charge carrier injection into the first and second organic functional layer stacks is possible over the entire operating time.

The organic light-emitting component can be used at temperatures above 80 ° C. without loss of efficiency or a reduction in service life. The organic light-emitting component is suitable, for example, for use in automobiles or outdoors.

In one embodiment, the charge carrier generation layer stack comprises a first electron-transporting layer comprising a second electron-transporting matrix material or a second electron-transporting matrix material and a second n-type dopant.

In one embodiment, the charge carrier generation layer stack comprises a first hole-transporting layer comprising a second hole-transporting matrix material or a second hole-transporting matrix material and a second p-type dopant.

In one embodiment, the charge carrier generation layer stack consists of the first electron-transporting layer, which is formed by crosslinking the first electron-transporting matrix material and the first n-type dopant, which has at least one functional group selected from a group which Comprises oxetane, epoxy and acrylic groups and is produced from a first hole-transporting layer comprising a second hole-transporting matrix material and a second p-type dopant. In this way, the diffusion of the first n-dopant into the first hole-transporting layer is prevented. The first electron-transporting layer also exhibits a barrier effect for the diffusion of the second p-type dopant into the first electron-transporting layer.

In one embodiment, the charge carrier generation layer stack consists of the first hole-transporting layer, which is formed by crosslinking the first hole-transporting matrix material and the first p-dopant, which has at least one functional group selected from a group consisting of the oxetane, epoxy and acrylic groups comprises, is produced and from a first electron-transporting layer comprising a second electron-transporting matrix material and a second n-type dopant. This prevents the diffusion of the first p-type dopant into the first electron-transporting layer. The first hole-transporting layer also exhibits a barrier effect for the diffusion of the second n-type dopant into the first hole-transporting layer.

In one embodiment, the charge carrier generation layer stack consists of the first electron-transporting layer, which is produced from the first electron-transporting matrix material and the first n-type dopant, and the first hole-transporting layer, which is produced from the first hole-transporting matrix material and the first p-type dopant. Thus, between the first electron-transporting layer and the first hole-transporting layer, there is no need for an intermediate layer as a diffusion barrier for the first n- and p-dopants, since these are firmly bound in the respective layer by chemical bonds, so that diffusion is not or only very slight takes place. One layer can thus be saved, which lowers the total thickness of the first charge carrier generation layer stack and thus also its light absorption and thus increases the efficiency of the organic light-emitting component.

In one embodiment, the first electron-transporting layer consists of the second electron-transporting matrix material or the second electron-transporting matrix material and the second n-type dopant. In particular, the second electron-transporting matrix material is not crosslinked with the second n-type dopant.

The second electron-transporting matrix material can be selected from a group consisting of NET-18, 2,2 ', 2 "- (1,3,5-benzene triyl) -tris (1-phenyl-1-H-benzimidazole), 2- ( 4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 8-hydroxyquinolinolato-lithium, 4- (naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazole, 1,3-bis [2- (2,2'-bipyridine-6-yl) -1.3 , 4-oxadiazo-5-yl] benzene, 4,7-diphenyl-1,10-phenanthroline (BPhen), 3- (4-biphenylyl) -4-phenyl-5-tert-butylphenyl-1,2,4- triazole, bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum, 6,6'-bis [5- (biphenyl-4-yl) -1,3,4-oxadiazo-2-yl] - 2,2'-bipyridyl, 2-phenyl-9,10-di (naphthalen-2-yl) -anthracene, 2,7-bis [2- (2,2'-bipyridine-6-yl) -1.3 , 4-oxadiazo-5-yl] -9,9-dimethylfluorene, 1,3-bis [2- (4-tert-butylphenyl) -1,3,4-oxadiazo-5-yl] benzene, 2- (naphthalene -2-yl) -4,7-diphenyl-1,10-phenanthroline, 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline, tris (2,4,6 -trimethyl-3- (pyridin-3-yl) phenyl) borane, 1-methyl-2- (4 - (Naphthalen-2-yl) phenyl) -1H-imidazo [4,5-f] [1,10] phenanthroline, phenyldipyrenylphosphine oxides, naphthalene tetracarboxylic acid dianhydride and its imides, perylenetetracarboxylic acid dianhydride and its imides, materials based on siloles with a silacyclopentadiene unit includes the aforementioned substances.

In one embodiment, the first electron-transporting matrix material is selected from the same materials as the second electron-transporting matrix material, said materials having at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups.

In one embodiment, the first electron-transporting matrix material or a portion of the first electron-transporting matrix material has at least one functional group which is selected from a group which comprises oxetane, epoxy and acrylic groups and is functionalized with a crosslinking initiator which is selected from a group , which includes sulfonium or iodonium salts. The proportion can be 0.5 to 10 mol%, preferably 0.5 to 5 mol%, particularly preferably 0.5 to 2 mol%, based on the total amount of first electron-transporting matrix material. In a preferred embodiment, the ratio of the oxetane, epoxy and / or acrylic groups to the crosslinking initiator is 200: 1 to 10: 1.

The first electron-transporting matrix materials selected in this way do not influence the electro-optical properties of the organic light-emitting component. This applies both to the free molecules and to the molecules crosslinked with the first n-dopants.

For example, the first electron-transporting matrix material has one of the following formulas:

The epoxy, oxetane or acrylic groups can substitute any H atom of the aromatics. Several H atoms can also be substituted by epoxy, oxetane or acrylic groups. For example, the first electron-transporting matrix material can have one of the following formulas:

R³ ₂S⁺A^- oder R³I⁺A^- können jedes beliebige H-Atom des Aromaten substituieren. Es können auch mehrere H-Atom des Aromaten durch R³ ₂S⁺A^- oder R³I⁺A^- substituiert sein. Die Reste R³ können beispielsweise Alkyl- oder Arylreste sein. Beispielsweise kann R³ ein Phenyl- oder Methylrest sein. Bei A^- handelt es sich um ein Anion, beispielsweise um BF₄ ^-, PF₆ ^- SbF₆ ^- oder 0,5 CO₃ ^2-.If the first electron-transporting matrix material is additionally functionalized with a crosslinking initiator, it has, for example, one of the following formulas:

R ³ ₂ S ⁺ A ^- or R ³ I ⁺ A ^- can substitute any H atom of the aromatic. Several H atoms in the aromatic can also be substituted by R ³ ₂ S ⁺ A ^- or R ³ I ⁺ A ^- . The radicals R ³ can be, for example, alkyl or aryl radicals. For example, R ³ can be a phenyl or methyl radical. A ^- is an anion, for example BF ₄ ^- , PF ₆ ^- SbF ₆ ^- or 0.5 CO ₃ ^2- .

sein, die , Na, Ca, MgAg, Cs, Li, Mg, Cs₂CO₃, und Cs₃PO₄ umfasst.The second n-type dopant can be selected from a group

which includes Na, Ca, MgAg, Cs, Li, Mg, Cs ₂ CO ₃ , and Cs ₃ PO ₄ .

According to the invention, the first n-dopant is a cesium salt which has at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups.

wobei R¹ und R für einen Alkyl- oder Arylrest stehen, die zumindest eine funktionelle Gruppe aufweisen, die aus einer Gruppe ausgewählt ist, die Oxetan-, Epoxid- und Acrylgruppen umfasst.For example, the cesium salt has one of the following structures

where R ¹ and R stand for an alkyl or aryl radical which have at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups.

For example, R ^{1 is} selected from a group comprising methyl, ethyl, propyl, butyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene and 2,6-pyridylene radicals, the have at least one functional group selected from a group including oxetane, epoxy and acrylic groups.

For example, R is selected from a group comprising methyl, ethyl, propyl, butyl and phenyl radicals having at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups.

For example, the cesium salt has one of the following formulas:

The epoxy groups can substitute any H atom that is bonded to the aryl radical. It is also possible for two H atoms to be replaced by epoxy groups. Instead of the epoxy groups, there can also be oxetane or acrylic groups.

The first hole-transporting matrix material can be selected from a group consisting of α-NPD, NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -benzidine), beta-NPB N, N'-bis (naphthalen-2-yl) -N, N'-bis (phenyl) -benzidine), N, N'-bis (phenyl) -N, N'-bis (phenyl) -benzidine), TPD ( N, N'-Bis (3-methylphenyl) -N, N'-bis (phenyl) -benzidine), Spiro TPD (N, N'-Bis (3-methylphenyl) -N, N'-bis (phenyl) - benzidine), Spiro-NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -spiro), DMFL-TPD N, N'-bis (3-methylphenyl) -N , N'-bis (phenyl) -9,9-dimethyl-fluorene), DMFL-NPB (N, N'-bis (naphthalen-1-yl) -N, N'bis (phenyl) -9,9-dimethyl -fluoren), DPFL-TPD (N, N'-Bis (3-methylphenyl) -N, N'-bis (phenyl) -9,9-diphenyl-fluorene), DPFL-NPB (N, N'-Bis ( naphthalen-1-yl) -N, N'-bis (phenyl) -9,9-diphenylfluorene), Spiro-TAD (2,2 ', 7,7'-tetrakis (N, N-diphenylamino) -9.9 -Spirobifluorene), 9,9-bis [4- (N, N-bis-biphenyl-4-ylamino) phenyl] -9H-fluorene, 9,9-bis [4- (N, N-bis-naphthalene- 2-ylamino) phenyl] -9H-fluorene, 9,9-bis [4- (N, N'-bis-naphthalene-2yl-N, N'-bis-phenyl-amino) -ph enyl] -9H-fluoro, N, N'-bis (phenanthren-9-yl) -N, N'-bis (phenyl) -benzidine, 2,7-bis [N, N-bis (9,9-spiro -bifluorene-2-yl) amino] -9,9-spiro-bifluorene, 2,2'-bis [N, N-bis (biphenyl-4-yl) amino] 9,9-spiro-bifluorene, 2, 2'-bis (N, N-di-phenyl-amino) 9,9-spiro-bifluorene, di- [4- (N, N-ditolyl-amino) -phenyl] cyclohexane, 2.2 ', 7.7 '-tetra (N, N-di-tolyl) amino-spiro-bifluorene, N, N, N', N'-tetra-naphthalen-2-yl-benzidine and mixtures of these compounds, the materials mentioned at least one functional Have a group selected from a group consisting of oxetane, epoxy and acrylic groups. The first hole-transporting matrix materials selected in this way do not influence the electro-optical properties of the organic light-emitting component. This applies both to the free molecules and to the molecules crosslinked with the first p-dopants.

In one embodiment, the first hole-transporting matrix material or a portion of the first hole-transporting matrix material has at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups and is functionalized with a crosslinking initiator selected from one group , which includes sulfonium or iodonium salts. The proportion can be 0.5 to 10 mol%, preferably 0.5 to 5 mol%, particularly preferably 0.5 to 2 mol%, based on the total amount of first hole-transporting matrix material.

The first hole-transporting matrix material can have one of the following formulas:

The epoxy, oxetane or acrylic groups can substitute any H atom of the aromatics. Several H atoms can also be substituted by epoxy, oxetane or acrylic groups. For example, the first hole-transporting matrix material can have one of the following formulas:

R³ ₂S⁺A^- oder R³I⁺A^- können jedes beliebige H-Atom der Aromaten substituieren. Es können auch mehrere H-Atome des Aromaten durch R³ ₂S⁺A^- oder R³I⁺A^- substituiert sein. Die Reste R³ können beispielsweise Alkyl- oder Arylreste sein. Beispielsweise kann R³ ein Phenyl- oder Methylrest sein. Bei A^- handelt es sich um ein Anion, beispielsweise um BF₄ ^-, PF₆ ^-, SbF₆ ^- oder 0,5 CO3^2-.If the first hole-transporting matrix material is additionally functionalized with a crosslinking initiator, it has, for example, one of the following formulas:

R ³ ₂ S ⁺ A ^- or R ³ I ⁺ A ^- can substitute any desired H atom of the aromatics. Several H atoms of the aromatic can also be substituted by R ³ ₂ S ⁺ A ^- or R ³ I ⁺ A ^- . The radicals R ³ can be, for example, alkyl or aryl radicals. For example, R ³ can be a phenyl or methyl radical. A ^- is an anion, for example BF ₄ ^- , PF ₆ ^- , SbF ₆ ^- or 0.5 CO3 ^2- .

In one embodiment, the first p-type dopant is a Lewis acidic compound that has at least one functional group selected from a group consisting of oxetane, epoxy, and acrylic groups.

The first p-type dopant can be selected from a group comprising MoO _x , WO _x , VO _x , copper benzoates such as Cu (I) pFBz, Bi (III) pFBz, F4-TCNQ, NDP-2, NDP-9, zinc phthalocyanine wherein said materials have at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups. The first p-type dopant can preferably be selected from a group which includes copper benzoates such as Cu (I) pFBz, Bi (III) pFBz, F4-TCNQ, NDP-2, NDP-9, zinc phthalocyanine, the materials mentioned having at least one functional group selected from a group consisting of oxetane , Epoxy and acrylic groups.

In one embodiment, the first hole-transporting layer consists of the second hole-transporting matrix material or the second hole-transporting matrix material and the second p-type dopant. In particular, the second hole-transporting matrix material is not crosslinked with the second p-type dopant.

The second p-type dopant can be selected from a group comprising MoO _x , WO _x , VO _x , Cu (I) pFBz, Bi (III) pFBz, F4-TCNQ, zinc phthalocyanine, NDP-2, and NDP-9. For example, the second p-type dopant is V ₂ O ₅ , MoO ₃ or WO ₃ .

The second hole-transporting matrix material can be selected from a group consisting of α-NPD, NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -benzidine), beta-NPB N, N'-bis (naphthalen-2-yl) -N, N'-bis (phenyl) -benzidine), (N, N'-bis (phenyl) -N, N'-bis (phenyl) -benzidine), TPD (N, N'-Bis (3-methylphenyl) -N, N'-bis (phenyl) -benzidine), Spiro TPD (N, N'-Bis (3-methylphenyl) -N, N'-bis (phenyl) -benzidine), Spiro-NPB (N, N'-Bis (naphthalen-1-yl) -N, N'-bis (phenyl) -spiro), DMFL-TPD N, N'-Bis (3-methylphenyl) - N, N'-bis (phenyl) -9,9-dimethyl-fluorene), DMFL-NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -9.9 -dimethyl-fluorene), DPFL-TPD (N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl) -9,9-diphenyl-fluorene), DPFL-NPB (N, N'- Bis (naphthalen-1-yl) -N, N'-bis (phenyl) -9,9-diphenyl-fluorene), Spiro-TAD (2,2 ', 7,7'-tetrakis (N, N-diphenylamino) -9,9 ‚-spirobifluorene), 9,9-bis [4- (N, N-bis-biphenyl-4-yl-amino) phenyl] -9H-fluorene, 9,9-bis [4- (N, N-bis-naphthalen-2-yl-amino) phenyl] -9H-fluorene, 9,9-bis [4- (N, N'-bis-naphthalen-2-yl-N, N'-bis-phenyl- at the ino) -phenyl] -9H-fluoro, N, N'-bis (phenanthren-9-yl) -N, N'-bis (phenyl) -benzidine, 2,7-bis [N, N-bis (9, 9-spiro-bifluorene-2-yl) -amino] -9,9-spiro-bifluorene, 2,2'-bis [N, N-bis (biphenyl-4-yl) amino] 9,9-spiro- bifluorene, 2,2'-bis (N, N-di-phenyl-amino) 9,9-spiro-bifluorene, di- [4- (N, N-ditolyl-amino) -phenyl] cyclohexane, 2,2 ' , 7,7'-tetra (N, N-di-tolyl) amino-spiro-bifluorene, N, N, N ', N'-tetra-naphthalen-2-yl-benzidine and mixtures of these compounds.

The first or second p-type dopant can be present in the first hole-transporting layer in a proportion of 0.1 to 40% by volume, preferably 0.5 to 20% by volume and particularly preferably 1 to 10% by volume.

The first or second n-type dopant can be present in the first electron-transporting layer in a proportion of 0.1 to 40% by volume, preferably 0.5 to 20% by volume and particularly preferably 1 to 10% by volume.

Because the first electron-transporting and / or the first hole-transporting matrix material is present in excess compared to the first n-dopant and / or the first p-dopant, it can be ensured that each or almost every molecule of the first n- and / or p-dopant is or is crosslinked with the respective matrix material.

The first electron-transporting layer and / or the first hole-transporting layer can have a layer thickness in a range from 5 nm to 200 nm, preferably 10 nm and 120 nm, particularly preferably 30 and 80 nm.

At these layer thicknesses, the charge carrier generation layer stack has a transmission which is greater than 80%, preferably 90% in a wavelength range from approximately 400 nm to approximately 700 nm.

In one embodiment, the organic light-emitting component has a third organic functional layer stack and a further charge carrier generation layer stack. The further charge carrier generation layer stack is arranged on the second functional layer stack and the third organic functional layer stack is arranged on the further charge carrier generation layer stack. The third organic functional layer stack can be constructed like the first or the second organic functional layer stack. The further charge carrier generation layer stack can be constructed and produced like the charge carrier generation layer stack.

In one embodiment, the organic light-emitting component can be embodied as an organic light-emitting diode (OLED).

The specified embodiments of the organic light-emitting component can be produced according to the method mentioned below. All of the features of the organic light-emitting component mentioned under the method can also be features of the exemplary embodiments of the organic light-emitting component set out above.

1. A) Ausbilden eines ersten organischen funktionellen Schichtenstapels auf einer ersten Elektrode,
2. B) Ausbilden eines Ladungsträgererzeugungs-Schichtenstapels auf dem ersten organischen funktionellen Schichtenstapel,
3. C) Ausbilden eines zweiten organischen funktionellen Schichtenstapels auf dem Ladungsträgererzeugungs-Schichtenstapel,
4. D) Anordnen einer zweiten Elektrode auf dem zweiten organischen funktionellen Schichtenstapel.

A method for producing an organic light-emitting component is specified. The procedure comprises the following procedural steps:

1. A) forming a first organic functional layer stack on a first electrode,
2. B) forming a charge carrier generation layer stack on the first organic functional layer stack,
3. C) forming a second organic functional layer stack on the charge carrier generation layer stack,
4. D) Arranging a second electrode on the second organic functional layer stack.

Process step B) comprises the following

• B1) Ausbilden einer ersten elektronentransportierenden Schicht, und B2) Ausbilden einer ersten lochtransportierenden Schicht.

Process steps:

• B1) forming a first electron-transporting layer, and B2) forming a first hole-transporting layer.

• B11) Aufbringen eines ersten elektronentransportierenden Matrixmaterials und eines ersten n-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel und
• B13) Vernetzen des ersten n-Dotierstoffs mit dem ersten elektronentransportierenden Matrixmaterial.

According to the invention, method step B1) comprises the following method steps:

• B11) applying a first electron-transporting matrix material and a first n-type dopant to the first organic functional layer stack and
• B13) crosslinking of the first n-type dopant with the first electron-transporting matrix material.

• B21) Aufbringen eines ersten lochtransportierenden Matrixmaterials und eines ersten p-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel und
• B23) Vernetzen des ersten p-Dotierstoffs mit dem ersten lochtransportierenden Matrixmaterial.

According to the invention, method step B2) comprises the following method steps:

• B21) applying a first hole-transporting matrix material and a first p-type dopant to the first organic functional layer stack and
• B23) crosslinking of the first p-type dopant with the first hole-transporting matrix material.

• B11) Aufbringen eines ersten elektronentransportierenden Matrixmaterials und eines ersten n-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel,

wobei der erste n-Dotierstoff und/oder der erste n-Dotierstoff und das erste elektronentransportierende Matrixmaterial zumindest eine funktionelle Gruppe aufweisen, die aus einer Gruppe ausgewählt ist, die Oxetan-, Epoxid- und Acrylgruppen umfasst oder

• B11) Aufbringen eines zweiten elektronentransportierenden Matrixmaterials oder eines zweiten elektronentransportierenden Matrixmaterials und eines zweiten n-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel.

In one embodiment, method step B1) comprises the following method step:

• B11) applying a first electron-transporting matrix material and a first n-type dopant to the first organic functional layer stack,

wherein the first n-dopant and / or the first n-dopant and the first electron-transporting matrix material have at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups or

• B11) applying a second electron-transporting matrix material or a second electron-transporting matrix material and a second n-type dopant to the first organic functional layer stack.

• B13) Vernetzen des ersten n-Dotierstoffs mit dem ersten elektronentransportierenden Matrixmaterial über die jeweils zumindest eine funktionelle Gruppe.

According to the invention, a further process step takes place after process step B11):

• B13) crosslinking of the first n-dopant with the first electron-transporting matrix material via the at least one functional group in each case.

• B21) Aufbringen eines ersten lochtransportierenden Matrixmaterials und eines ersten p-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel, wobei der erste p-Dotierstoff und/oder der erste p-Dotierstoff und das erste lochtransportierende Matrixmaterial zumindest eine funktionelle Gruppe aufweisen, die aus einer Gruppe ausgewählt ist, die Oxetan-, Epoxid- und Acrylgruppen umfasst, oder
• B21) Aufbringen eines zweiten lochtransportierenden Matrixmaterials oder eines zweiten lochtransportierenden Matrixmaterials und eines zweiten p-Dotierstoffs auf dem ersten organischen funktionellen Schichtenstapel.

In one embodiment, method step B2) comprises the following method step:

• B21) applying a first hole-transporting matrix material and a first p-dopant to the first organic functional layer stack, the first p-dopant and / or the first p-dopant and the first hole-transporting matrix material having at least one functional group selected from one group which includes oxetane, epoxy and acrylic groups, or
• B21) applying a second hole-transporting matrix material or a second hole-transporting matrix material and a second p-type dopant on the first organic functional layer stack.

• B23) Vernetzen des ersten p-Dotierstoffs mit dem ersten lochtransportierenden Matrixmaterial über die jeweils zumindest eine funktionelle Gruppe.

In one embodiment, a further process step takes place after process step B21):

• B23) crosslinking of the first p-dopant with the first hole-transporting matrix material via the at least one functional group in each case.

In one embodiment, the crosslinking of the first n-dopant with the first electron-transporting matrix material in method step B13) and / or the crosslinking of the first p-dopant with the first hole-transporting matrix material in method step B23) is initiated by a crosslinking initiator.

In one embodiment, the crosslinking initiator is selected from a group comprising nitric oxide gases, iodonium, sulfonium, and nitrosonium salts.

In one embodiment, the iodonium or sulfonium salt is bound to the first electron-transporting matrix material and / or the first hole-transporting material. It is also possible that the iodonium or sulfonium salt is only bound to a portion of the first electron-transporting matrix material and / or the first hole-transporting matrix material.
In one embodiment, the iodonium or sulfonium salt is covalently bound to the first electron-transporting matrix material and / or the first hole-transporting material.

As iodonium and sulfonium salts, R ₂ S ⁺ A ^- or RI ⁺ A ^{- can be} bound to the first electron-transporting matrix material and / or the first hole-transporting material. The radicals R can be, for example, alkyl or aryl radicals. For example, R ³ can be a phenyl or methyl radical. A ^- is an anion, for example BF ₄ ^- , PF ₆ ^- , SbF ₆ ^- or 0.5 CO ₃ ^2- .

The nitrosonium salt can be, for example, NO ⁺ SbF ₆ ^- .

• B12) Temperaturerhöhung oder UV-Bestrahlung des ersten elektronentransportierenden Matrixmaterials und des ersten n-Dotierstoffs. Die Maßnahmen in Verfahrensschritt B12) dienen dazu die Vernetzung zu aktivieren. Beispielsweise können Radikalkationen des ersten elektronentransportierenden Matrixmaterials und/oder des ersten n-Dotierstoffs gebildet werden. Insbesondere findet Verfahrensschritt B12) beim Einsatz von Iodonium- oder Sulfoniumsalzen als Vernetzungsinitiatoren statt.

According to one embodiment, the following process step takes place after process step B11) or after process step B13):

• B12) temperature increase or UV irradiation of the first electron-transporting matrix material and of the first n-dopant. The measures in method step B12) serve to activate the networking. For example, radical cations of the first electron-transporting matrix material and / or of the first n-type dopant can be formed. In particular, method step B12) takes place when using iodonium or sulfonium salts as crosslinking initiators.

• B22) Temperaturerhöhung oder UV-Bestrahlung des ersten lochtransportierenden Matrixmaterials und des ersten p-Dotierstoffs. Die Maßnahmen in Verfahrensschritt B22) dienen dazu, die Vernetzung zu aktivieren. Beispielsweise können Radikalkationen des ersten lochtransportierenden Matrixmaterials und/oder des ersten p-Dotierstoffs gebildet werden. Insbesondere findet Verfahrensschritt B22) beim Einsatz von Iodonium- oder Sulfoniumsalzen als Vernetzungsinitiatoren statt.

According to one embodiment, the following process step takes place after process step B21) or after process step B23):

• B22) Increase in temperature or UV irradiation of the first hole-transporting matrix material and of the first p-type dopant. The measures in method step B22) serve to activate the networking. For example, radical cations of the first hole-transporting matrix material and / or of the first p-type dopant can be formed. In particular, method step B22) takes place when using iodonium or sulfonium salts as crosslinking initiators.

In one embodiment, the temperature in method step B12) and / or B22) is increased to up to 120 ° C., preferably 80 ° C.

steht in dem Reaktionsschema für den ersten p- oder n-Dotierstoff oder für das erste loch- oder elektronentransportierende Matrixmaterial, der mit zumindest einer Oxetangruppe funktionalisiert ist. Y⁺A^- repräsentiert in diesem Reaktionsschema ein Iodonium- oder Sulfoniumsalz als Vernetzungsinitiator. Das dargestellte Zwischenprodukt oder das Endprodukt reagiert mit einem weiteren

Beispielsweise steht

für einen ersten n-Dotierstoff folgender Formel:

oder für einen p-Dotierstoff wie beispielsweise ein Oxetan-funktionalisiertes Kupferbenzoat.If the first p-dopant and the first hole-transporting matrix material are functionalized with at least one oxetane group or if the first n-dopant and the first electron-transporting matrix material are functionalized with at least one oxetane group, the following reaction takes place, for example:

in the reaction scheme stands for the first p- or n-dopant or for the first hole- or electron-transporting matrix material which is functionalized with at least one oxetane group. Y ⁺ A ^- represents in this reaction scheme an iodonium or sulfonium salt as a crosslinking initiator. The intermediate product shown or the end product reacts with another

For example

for a first n-dopant the following formula:

or for a p-type dopant such as an oxetane-functionalized copper benzoate.

The first hole-transporting matrix material can have the following formula:

Ist der erste p-Dotierstoff und das erste lochtransportierende Matrixmaterial mit zumindest einer Epoxidgruppe funktionalisiert oder ist der erste n-Dotierstoff und das erste elektronentransportierende Matrixmaterial mit zumindest einer Epoxidgruppe funktionalisiert, findet beispielsweise folgende Reaktion statt:

steht in dem Reaktionsschema für den ersten p- oder n-Dotierstoff oder für das erste loch- oder elektronentransportierende Matrixmaterial, der mit zumindest einer Epoxidgruppe funktionalisiert ist. Y⁺A^- repräsentiert in diesem Reaktionsschema ein Iodonium- oder Sulfoniumsalz als Vernetzungsinitiator. Das dargestellte Zwischenprodukt oder das Endprodukt reagiert mit einem weiteren

For example, the first electron-transporting matrix material has the following formula:

If the first p-dopant and the first hole-transporting matrix material are functionalized with at least one epoxy group or if the first n-dopant and the first electron-transporting matrix material are functionalized with at least one epoxy group, the following reaction takes place, for example:

in the reaction scheme stands for the first p- or n-dopant or for the first hole- or electron-transporting matrix material which is functionalized with at least one epoxy group. Y ⁺ A ^- represents in this reaction scheme an iodonium or sulfonium salt as a crosslinking initiator. The intermediate product shown or the end product reacts with another

für einen ersten n-Dotierstoff folgender Formel:

Ist der erste p-Dotierstoff und das erste lochtransportierende Matrixmaterial mit zumindest einer Acrylgruppe funktionalisiert oder ist der erste n-Dotierstoff und das erste elektronentransportierende Matrixmaterial mit zumindest einer Acrylgruppe funktionalisiert, findet beispielsweise folgende Reaktion statt:

steht in dem Reaktionsschema für den ersten p- oder n-Dotierstoff oder für das erste loch- oder elektronentransportierende Matrixmaterial, der mit zumindest einer Epoxidgruppe funktionalisiert ist. Y⁺A^- repräsentiert in diesem Reaktionsschema ein Iodonium-, Sulfonium- und Nitrosoniumsalze als Vernetzungsinitiator. Das dargestellte Zwischenprodukt oder Endprodukt reagiert mit einem weiteren

For example

for a first n-dopant the following formula:

If the first p-dopant and the first hole-transporting matrix material are functionalized with at least one acrylic group, or if the first n-dopant and the first electron-transporting matrix material are functionalized with at least one acrylic group, the following reaction takes place, for example:

in the reaction scheme stands for the first p- or n-dopant or for the first hole- or electron-transporting matrix material which is functionalized with at least one epoxy group. Y ⁺ A ^- in this reaction scheme represents an iodonium, sulfonium and nitrosonium salt as a crosslinking initiator. The intermediate or final product shown reacts with another

für einen ersten n-Dotierstoff folgender Formel:

For example

for a first n-dopant the following formula:

In one embodiment, the first electron-transporting matrix material and the first n-dopant, the second electron-transporting matrix material or the second electron-transporting matrix material and the second n-dopant are applied from the gas phase in method step B11) and / or in method step B21) the first hole-transporting matrix material is applied and the first p-type dopant, the second hole-transporting matrix material or the second hole-transporting matrix material and the second p-type dopant are applied from the gas phase.

In one embodiment, the first electron-transporting matrix material and the first n-dopant, the second electron-transporting matrix material or the second electron-transporting matrix material and the second n-dopant are applied from a solution in method step B11) and / or in method step B21) the first hole-transporting matrix material is applied and the first p-type dopant, the second hole-transporting matrix material or the second hole-transporting matrix material and the second p-type dopant are applied from a solution.

In one embodiment, gases are split off during the crosslinking in method step B13) and / or B23). For example, N ₂ , NOx, O ₂ , CO and / or CO ₂ can be released.

In one embodiment the solvent is an organic solvent. The solvent can be polar or non-polar, depending on the matrix material and dopant. For example, THF, toluene, phenetole, anisole, dichloromethane or acetonitrile can be used.

In one embodiment, the at least one oxetane, epoxy or acrylic group is bound to the first n-dopant and / or to the first electron-transporting matrix material and / or to the first p-dopant and / or to the first hole-transporting matrix material via an alkyl group.

In one embodiment, the at least one iodonium and sulfonium salt is bound to the first electron-transporting matrix material and / or to the first hole-transporting matrix material via an alkyl group.

By attaching the respective functional group via an alkyl group, the mobility or the flexibility of the respective functional group is increased, which leads to a higher degree of crosslinking.

The solubility of the first n-type dopant, the first p-type dopant, the first electron-transporting matrix material and / or the first hole-transporting matrix material can thus be increased. In particular, this embodiment is present if in method step B11) the first electron-transporting matrix material and the first n-dopant are applied from a solution and / or in method step B21) the first hole-transporting matrix material and the first p-dopant are applied from a solution.

• 1 zeigt eine schematische Seitenansicht eines Ausführungsbeispiels eines organischen Licht emittierenden Bauelements.

In one embodiment, the alkyl group is selected from a group comprising butyl, pentyl, hexyl and heptyl groups. Pentyl and hexyl groups are preferred, hexyl groups are particularly preferred. Further advantages, advantageous embodiments and developments result from the embodiments described below in connection with the figure.

• 1 shows a schematic side view of an embodiment of an organic light-emitting component.

In the exemplary embodiments and figures, elements that are the same, of the same type or have the same effect can be provided with the same reference symbols. The elements shown in the figure and their proportions to one another are not to be regarded as true to scale; rather, individual elements such as layers, components, components and areas can be shown exaggeratedly large for better illustration and / or for better understanding.

In 1 an exemplary embodiment for an organic light-emitting component is shown. This has a substrate 10 , a first electrode 20th , a first organic functional layer stack 30th , a charge carrier generation layer stack 40 , a second organic functional layer stack 50 , a second electrode 60 , a barrier film 70 as well as a cover 80 on. The first organic functional layer stack 30th comprises a hole injection layer 31 , a first hole transport layer 32 , a first emission layer 33 and an electron transport layer 34 . The second organic functional layer stack 50 comprises a second hole transport layer 51 , a second emission layer 52 , a second electron transport layer 53 and an electron injection layer 54 . The charge carrier generation layer stack 40 comprises a first electron transporting layer 41 and a first hole transporting layer 42 .

The substrate 10 can serve as a carrier element and be made of glass, for example.

The component in 1 can be set up as a top or bottom emitter in various embodiments. Furthermore, it can also be set up as a top and bottom emitter, and thus an optically transparent component, for example a transparent organic light-emitting diode.

The first electrode 20th is designed as an anode and can have ITO as the material, for example. If the component is to be designed as a bottom emitter, it is a substrate 10 and first electrode 20th translucent. In the event that the component is to be designed as a top emitter, the first electrode can 20th preferably also be reflective. The second electrode 60 is designed as a cathode and can, for example, comprise a metal or a TCO. The second electrode too 60 can be designed to be translucent if the component is designed as a top emitter.

The barrier thin layer 70 protects the organic layers from damaging materials from the environment, such as moisture and / or oxygen and / or other corrosive substances such as hydrogen sulfide. The barrier thin layer can do this 70 have one or more thin layers, which are applied, for example, by means of an atomic layer deposition process and which have, for example, one or more of the materials aluminum oxide, zinc oxide, zirconium oxide, titanium oxide, hafnium oxide, lanthanum oxide and tantalum oxide. The barrier thin layer 70 furthermore has a mechanical protection in the form of the encapsulation 80 which is designed for example as a plastic layer and / or as a laminated glass layer, whereby, for example, scratch protection can be achieved.

The emission layers 33 and 52 have for example an electroluminescent material mentioned in the general part. These can be selected to be either the same or different. Furthermore, charge carrier blocking layers (not shown here) can be provided, between which the organic light-emitting emission layers 33 and 52 are arranged.

For example, a hole blocking layer which comprises 2,2 ', 2 "- (1,3,5-benzene triyl) -tris (1-phenyl-1-H-benzimidazole) can be present as the charge carrier blocking layer. An electron blocking layer can also be present as the charge carrier blocking layer which includes, for example, NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -benzidine).

Materials for the hole transport layers 32 and 51 , for the hole injection layer 31 , for the electron transport layers 34 and 53 as well as for the electron injection layer 54 can be selected from known materials. For example, for the hole transport layers 32 and 51 NPB (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -benzidine) can be used.

Furthermore, for the electron transport layers 34 and 53 for example 2,2 ', 2 "- (1,3,5-petroletriyl) -tris (1-phenyl-1-H-benzimidazole) can be used.

und einem ersten n-Dotierstoff folgender Formel

hergestellt ist und eine Dicke von 100 nm aufweist. Es ist auch möglich, dass die Oxetangruppen über eine Hexylgruppe angebunden sind. Die erste elektronentransportierende Schicht wurde wie folgt hergestellt:

• - Aufbringen einer Lösung des ersten elektronentransportierenden Matrixmaterials und des n-Dotierstoffs auf den ersten organischen funktionellen Schichtenstapel 30 in einem organischen Lösungsmittel.
• - Vernetzung des ersten elektronentransportierenden Matrixmaterials mit dem ersten n-Dotierstoff über die Oxetangruppen mit NO⁺SbF₆ ^- als Vernetzungsinitiator.

The charge carrier generation layer stack 40 contains in the exemplary embodiment a first electron-transporting layer 41 made from a first electron-transporting matrix material with the following formula

and a first n-type dopant of the following formula

is made and has a thickness of 100 nm. It is also possible for the oxetane groups to be attached via a hexyl group. The first electron-transporting layer was made as follows:

• Applying a solution of the first electron-transporting matrix material and the n-type dopant to the first organic functional layer stack 30th in an organic solvent.
• - Crosslinking of the first electron-transporting matrix material with the first n-dopant via the oxetane groups with NO ⁺ SbF ₆ ^- as a crosslinking initiator.

• - Aufbringen einer Lösung des ersten lochtransportierenden Matrixmaterials und des ersten p-Dotierstoffs auf der ersten elektronentransportierenden Schicht 41 in einem organischen Lösungsmittel. Das erste lochtransportierende Matrixmaterial weist folgende Formel auf:

The first hole-transporting layer 42 was made as follows:

• Applying a solution of the first hole-transporting matrix material and the first p-type dopant to the first electron-transporting layer 41 in an organic solvent. The first hole-transporting matrix material has the following formula:

• - Vernetzung des ersten lochtransportierenden Matrixmaterials mit dem ersten p-Dotierstoff über die Oxetangruppen mit NO⁺SbF₆ ^- als Vernetzungsinitiator.

The first p-type dopant is an oxetane-functionalized copper benzoate. It is also possible that the oxetane groups, the iodonium or sulfonium salt as a crosslinking initiator are attached via a hexyl group.

• - Crosslinking of the first hole-transporting matrix material with the first p-dopant via the oxetane groups with NO ⁺ SbF ₆ ^- as a crosslinking initiator.

The first electron-transporting layer 41 of the charge carrier generation layer stack 40 can alternatively consist of a second electron-transporting matrix material and a second n-dopant, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and Cs ₂ CO ₃ , or the first hole-transporting layer can alternatively consist of a second hole-transporting matrix material and a second p-type dopant. The second p-dopant can be VO _x and the second hole-transporting matrix material can have the following formula:

Claims (9)

Method for producing an organic light-emitting component with the method steps A) forming a first organic functional layer stack (30) on a first electrode (20), B) forming a charge carrier generation layer stack (40) on the first organic functional layer stack (30), C) forming a second organic functional layer stack (50) on the charge carrier generation layer stack (40), D) arranging a second electrode (60) on the second organic functional layer stack (50), process step B) comprising the following process steps: B1) forming a first electron-transporting layer (41) and B2) forming a first hole-transporting layer (42), wherein - Process step B1) comprises the following process steps: B11) applying a first electron-transporting matrix material and a first n-type dopant to the first organic functional layer stack (30) and B13) crosslinking of the first n-dopant with the first electron-transporting matrix material, and / or where - Process step B2) comprises the following process steps: B21) applying a first hole-transporting matrix material and a first p-type dopant to the first organic functional layer stack (30) and B23) crosslinking of the first p-type dopant with the first hole-transporting matrix material, and wherein the first n-type dopant is a cesium salt having at least one functional group selected from a group consisting of oxetane, epoxy and acrylic groups. Procedure according to Claim 1 wherein the first n-type dopant and the first electron transporting matrix material have at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups. The method according to any one of the preceding claims, wherein the first p-type dopant and the first hole-transporting matrix material have at least one functional group selected from a group comprising oxetane, epoxy and acrylic groups. Method according to one of the preceding claims, wherein the crosslinking of the first n-dopant with the first electron-transporting matrix material in method step B13) and / or the crosslinking of the first p-dopant with the first hole-transporting matrix material in method step B23) is initiated by a crosslinking initiator and the Crosslinking initiator is selected from a group comprising nitric oxide gases, iodonium, sulfonium and nitrosonium salts, and wherein the iodonium or sulfonium salt is bound to the first electron-transporting matrix material and / or the first hole-transporting material. Method according to one of the preceding claims, the following method step taking place after method step B11): B12) Increase in temperature or UV irradiation of the first electron-transporting matrix material and the first n-dopant and / or the following method step taking place after method step B21): B22) Increase in temperature or UV irradiation of the first hole-transporting matrix material and of the first p-type dopant. Method according to one of the preceding claims, wherein in method step B11) the first electron-transporting matrix material and the first n-dopant are applied from the gas phase and / or wherein in method step B21) the first hole-transporting matrix material and the first p-dopant are applied from the gas phase . Method according to one of the preceding claims, wherein in method step B11) the first electron-transporting matrix material and the first n-dopant are applied from a solution and / or wherein in method step B21) the first hole-transporting matrix material and the first p-dopant are applied from a solution . Method according to one of the Claims 2 to 7th , wherein the at least one oxetane, epoxy or acrylic group is bound to the first n-type dopant and the first electron-transporting matrix material and / or to the first p-type dopant and the first hole-transporting matrix material via an alkyl group. A method according to the preceding claim, wherein the alkyl group is selected from a group comprising butyl, pentyl, hexyl and heptyl groups.

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