EP1829131A1

EP1829131A1 - Organic electric or electronic component with increased service life

Info

Publication number: EP1829131A1
Application number: EP05820015A
Authority: EP
Inventors: Clemens Ottermann; Jörn POMMEREHNE; Klaus Bonrad; Thomas Frank; Marcus Bodesheim
Original assignee: Schott AG
Current assignee: Schott AG
Priority date: 2004-12-22
Filing date: 2005-12-22
Publication date: 2007-09-05
Also published as: CN101116196A; WO2006069722A1; DE102004063133A1; US20090114905A1

Abstract

The aim of the invention is to increase the service life of organic electric or electronic components. According to the invention, an organic electric or electronic component is provided with at least one organic functional layer, said component containing an (e-v)- singlet oxygen quenching agent.

Description

Organic electrical or electronic component with increased lifetime

description

The invention relates to organic electrical or electronic components, in particular the invention relates to measures to increase the life of such elements.

Organic electronic components are increasingly used for a wide variety of electronic applications. Although these are generally much slower than based on inorganic semiconductors elements, however, the production of organic components is much cheaper. Developments in this regard include printing complete circuits simply. Also, in many applications, the speed is not in the

Foreground. Examples include organic sensors and photovoltaic, organic transponder circuits for radio frequency identification ("RF-ID labels or labels).

However, in comparison to the materials of inorganic semiconductor devices, organic compounds are generally more unstable. A problem with organic electronic components is therefore still their limited life. The organic substances that are used as functional material in such components are often reactive and degrade inter alia

BESTATIGUNGSKOPIE under the influence of oxygen. For many applications where reliability is very important, failures due to component aging are still a major impediment to the continued spread of these products.

One way to increase the life of such elements is to gas-tightly encapsulate the one or more organic layers. However, oxygen may also penetrate over time. However, the oxygen can also be incorporated or enclosed in the component during component production. Thus, an inert gas used in the production may be contaminated or the materials used will release oxygen over time. Among other things, this is for

Electrode layers have widely used indium-tin-oxide (ITO) for slowly releasing oxygen, which can degrade the functional materials of organic electronic or electrical devices. Similarly, oxygen can be reversibly incorporated and released in many metals. For example, silver and copper are known to be relatively permeable to oxygen.

Another way to extend the life is therefore to keep existing oxygen from reacting with the organic functional materials. For example, the oxygen can be chemically bound with suitable substances, getter materials, scavengers, reducing agents or drying agents, especially for water.

Another possibility is to reduce the reactivity of the oxygen. This can be achieved by quenching oxygen in the singlet state. With oxygen exists a special feature is that the first two electronically excited molecular states 02 (a ^ -Δg) and O2 (b - * - Σ ⁺ g)

Singlet states and the ground state O2 (χ3Σ ^~ g)

Triplet state is. The O2 (a ^ Ag) singlet state is metastable based on selection rules with a lifetime of typically a few microseconds to a few hundred milliseconds, depending on the environment in which it is located. Since most organic functional molecules in the ground state have singlet multiplicity, a reaction of these molecules with ground state oxygen is kinetically inhibited. Owing to the singlet multiplicity and the 94.2 kJ / mol energy content of (^ (a ^ -Δg) compared to the ground state, however, oxygen molecules in this singlet state are a considerably stronger oxidant than triplet ground state oxygen.

It should be added that there is also another singlet state of the oxygen molecule, the

O2 (b ^ Σ ⁺ g) which has an energy of 157 kJ / mole above the ground state. This state, however, can pass into the O2 (a- ^ Ag), so that the

Life of the O2 (b ^ -Σ ⁺ g) in solvents, or in the presence of collision partners, at best, barely more than 100 nanoseconds. Accordingly, this state plays only a minor role in the deactivation of singlet oxygen.

From JP 05-190282 A and JP 05-190283 it is known to use singlet quencher in OLEDs. For example, β-carotene or ethylene compounds, such as tetramethyl ethylene, are to serve as quenchers. The non-radiative deactivation channel of singlet oxygen, which occurs in the quencher molecules described there, in particular in β-carotene, is the spin-allowed energy transfer (ET) to triplet states of the as

Acceptor molecules acting quencher substances. The necessary condition for deactivation is that the energy of the acceptor triplet be below that of the singlet donor. This deletion or deactivation mechanism is also referred to as so-called "chemical deletion".

Although β-carotene is known in biology and medicine as an excellent singlet oxygen quencher, in the application in organic electronic components there are several disadvantages. For example, carotene is an intense dye which, accordingly, can affect the optical properties of. Also, β-carotene and the molecules known in the art which are used as singlet oxygen quencher typically have a large molecular weight. However, such large molecules can negatively influence or even prevent the electrical properties of the organic layer (s) of the components or their polymerization and / or deposition during component production.

Tetramethyl ethylene is also known as a singlet oxygen chemical quencher. In this reaction is a non-radiative process in which the singlet oxygen attacks the double bond of tetramethyl ethylene and the reaction product is a hydroperoxide. The use of chemical quenchers such as tetramethyl ethylene can also be disadvantageous because the chemical quencher also trigger photochemical reactions and thus can change the organic layers. Moreover, in the chemical deactivation of singleton

Oxygen reaction products or further derived products, which in turn are reactive and can then attack the functional molecules of the organic functional layer or by coloring or other physical properties can affect the function of the device in a difficult to predict way negatively.

The invention is therefore based on the object to increase the life of organic layers of components while avoiding or at least reducing the above-mentioned disadvantages of known quenchers for OLEDs.

This object is already achieved in a surprisingly simple manner by the subject matter of the independent claims. Advantageous embodiments and modifications of the invention are the subject of the dependent claims.

Accordingly, the invention provides an organic electrical or electronic device having at least one organic functional layer containing a singlet oxygen (e-v) quenching substance. With particular preference, organic molecules are also used for the (e-v) quenching substance.

Such a device can be easily produced according to the invention by at least one organic functional layer on a substrate is applied, wherein in the device additionally an (ev) quenching substance is introduced.

In particular, an (e-v) quenching substance can be introduced into the organic functional layer or in direct or indirect contact therewith. Among other things, glass or even plastic, for example for the production of flexible components, can be used as the substrate.

For the purposes of this invention, an organic functional layer is to be understood as a layer having an organic substance which is essential for the electrical, electronic or optoelectronic function of the component. Thus, in the simplest case, an organic photovoltaic element or an organic photocell as optoelectronic component typically comprises a functional organic layer with organic photovoltaically active molecules embedded between two electrode layers having different work functions. In addition to this layer and the as

Anode and cathode-acting electrode layers may also contain other functional layers. In an organic transistor, as another example, as an organic functional layer, an organic semiconductive layer is used between source-drain and gate electrodes.

For the purposes of this invention, the (e-v) quenching substance is understood as meaning a substance with molecules which, owing to their functional group (s), are capable of producing singleton

Oxygen-induced by resonance energy transfer to vibronic states of the molecules to deactivate or quench oxygen. The electronic excitation energy in the collisions becomes vibrational energy of the collision partner, that is, the molecules of the (ev) quenching substance transformed. At the same time chemical deactivation occurs if necessary at the same time. The excitation energy of the singlet oxygen is converted accordingly only into thermal energy. A reaction of the quenching substance, which can lead to aggressive reaction products, is inventively avoided. In addition, the (ev) quenching essentially depends on the functional groups of the molecules and hardly on their overall structure. This makes it possible that also easily mentioned molecules with a small molecular weight can be installed, which do not interfere with the electrical properties of the functional layer or at most negligible. The energy transfer can be particularly resonant, that is, particularly efficient in the sense of taking place with particularly high rate constants, if the

Energy distances of the vibrational states of the (ev) - extinguishing substance molecules are adapted to the energy gap between singlet and ground state oxygen as well as possible. This means that it is advantageous if, during a resonant energy transfer, the electronic excitation energy of the singlet oxygen is converted as completely as possible into vibrational energy of the (ev) quenching substance molecules. Any surplus energy amounts are called missing energy. Thus ^' occurs a particularly efficient, ie resonant cancellation of

Singlet oxygen instead, when in the energy transfer little lack of energy occurs.

The vibrational energy of the (e-v) quenching substance molecules is a molecular property. In the (e-v) deletion of

Singlet oxygen mainly occupy the terminal molecular groups of an (ev) quenching substance molecule the singlet oxygen electronic energy. These terminal molecule groups are called terminal oscillators for the purposes of the invention. Thus, advantageously, an ev (ev) quenching substance can be used which contains molecules having at least one functional group with a terminal oscillator, the terminal oscillator having a vibrational energy of the fundamental vibration or an overtone of the stretching vibration equal to that of FIG

Energy difference between the g) state of molecular oxygen or whose vibrational energy deviates from this energy difference by at most 37%, preferably by at most 10%, in particular with a vibrational quantum number n less than or equal to 3 ,. In the range of these energetic deviations, the collision-induced energy transfer from the singlet oxygen under excitation of a stretching vibration is particularly probable, so that high rate constants for the resonant (ev) deactivation can be achieved.

When deactivating with an (e-v) quenching substance, the following reaction takes place:

O ^{2 1} A _g (Tn = O) -> O ^{2 3} Σ ^~ _g (m = 0, 1, 2, 3, ...), and XY (n = 0) -> XY (n = 1, 2 , 3 ....).

In this case, m denotes the oscillation quantum number of the stretching vibration of the oxygen molecule, n the oscillation quantum number of the stretching vibration of the (e-v) quenching substance and X-Y a terminal oscillator with atoms X, Y, for example a hydroxyl group of one

Molecule. The most effective contribution to the deletion is provided by the transition of oxygen from m = 0 to m = 0. For the purposes of the invention, the (ev) quenching substance is therefore particularly preferably understood to be a quenching substance. which contains at least one functional group with a terminal oscillator, the terminal oscillator having a vibrational energy of the fundamental vibration or an overtone of the stretching vibration which is equal to the vibrational energy

Energy difference between the O2 (a ^ -Δg) (m = 0) - and the

O2 (X ^ Σ ^~ g) (m = 0) state of molecular oxygen or its vibrational energy of this energy difference by more than 37%, preferably at most 10% deviates.

Particularly suitable for deactivating singlet oxygen are (e-v) quenching substances which contain molecules having at least one hydroxyl group. Particular preference is given to using organic molecules as (e-v) extinguishing substance, water not being regarded as an organic molecule in this sense. Water is particularly suitable for deactivating singlet oxygen, since water molecules are composed exclusively of OH groups. However, the use of water is only possible where the layers of the organic

Component, including functional layers and electrode layers are not damaged by the water, so that water for organic electronic components is generally less suitable. The hydroxy group with an O-H bond as a terminal oscillator is particularly well suited for resonant (e-v) quenching because the stretching energy is in good agreement with the resonant energy

Excitation energy of the O2 (a -'-Δg) state of the oxygen matches. ■

For example, however, the (ev) quenching substance may also contain molecules having at least one NH or NH 2 group or a CH bond. These are a little less effective as OH groups, but can also be achieved with NH or NH2 ~ groups, or with CH bonds in which a NH or CH bond in each case forms a terminal oscillator, nor a considerably accelerated quenching of the singlet oxygen can be achieved. In particular, it is also contemplated to use molecules containing both NH and OH bonds.

An (e-v) quenching substance can protect the organic functional layer particularly effectively if the (e-v)

Extinguishing substance is present in this layer itself.

In many cases, it is sufficient if the (e-v) -

Extinguishing substance in a concentration of at most 5

Weight percent of the active substance of the organic functional layer, preferably at most 1

Weight percent is present in the organic functional layer.

However, it may also be advantageous as an alternative or additional measure to accommodate the (e-v) quenching substance in a separate constituent of the device, thereby preventing singlet oxygen arising outside the organic functional layer from penetrating into the layer. This embodiment is possible because the rate constant of the diffusion of

Oxygen in the subject components is so high that deactivation of singlet oxygen in these layers can provide efficient protection of the functional layers.

Advantageously, molecules of small molecular weight can be used, which are easily movable in the organic functional layer and / or do not disturb the electronic properties of the layer or only slightly. Their molecular weight is preferably less than 528 g / mol, preferably in particular less than 374 g / mol and particularly preferably less than 178 g / mol. This means that preferably (ev) quenching substances are used which have a limited size or a limited number of

Have atoms in the molecule, so that the negative effects on the organic functional layers, in particular on the organic functional layer can be minimized as possible.

But it is also possible to use substances with a large molecular weight as extinguishing substances. Thus, according to another embodiment of the invention, it is provided that the (e-v) quenching substance comprises a polymer having hydroxyl groups or NH or NH 2 groups. This can for

Example form a matrix for the molecules of the organic functional layer. Also, such a polymer may be used as a constituent of the device adjacent to the organic functional layer with a surface so that singlet oxygen can be neutralized at the interface formed thereby.

The selection of the (e-v) quenching substance is advantageously also based on the layers of the device and their chemical and electrical properties. Examples of organic substances that can be used as extinguishers in one (e-v)

Extinguishing substance may be included are:

a monohydric or polyhydric alcohol, cyclohexanol,, -a

Carbohydrate, a cellulose derivative, a starch derivative, a glycerol monooleate, an aminoalcohol,

a polyamine, a polyamide.

In the selection of the (ev) quenching substance can then be considered, for example, whether the substance with a Solvent for the production of the organic functional layer and / or any other functional layers is miscible and / or whether the substance can react undesirably with one or more other substances of a layer of the organic electrical or electronic component.

As explained above, molecules with hydroxy groups are particularly effective quencher. The more hydroxyl groups are present, the better the corresponding

Extinguishing effect of the molecules. According to one embodiment of the invention, therefore, an organic electrical or electronic component is provided, in which the (e- v) quenching substance contains organic molecules having at least one hydroxyl group, wherein the ratio of total molecular weight of these molecules to the molecular weight of the hydroxy groups is at most 5 to 1 , preferably at most 3.5 to 1. For example, the ratio of total molecular weight to molecular weight of the one or more hydroxyl groups in the alcohols methanol is only 1.88 (total molecular weight M _ges = 32 g / mol, molecular weight of the hydroxyl groups M ₀ H = 17g / mol), with ethanol 2.7 (M _tot = 46 g / mol, M _0H = 17 g / mol), with ethylene glycol only 1.82 (M _tot = 62 g / mol, M _0H = 34 g / mol). Even with carbohydrates, low values of this ratio of molecular weights can be achieved. Thus, for example, a value of M _tot / M ₀ H = 3.17 results for cellulose. Sorbitol as an (ev) quencher even has a value of only M _ges / M ₀ H = 1.78.

One possibility for applying the at least one organic functional layer to a substrate for producing the organic component is a coating of the liquid or gel phase, such as spin coating, dip or groove coating or printing techniques, in particular inkjet printing, screen printing or flexographic printing. In this case, a solution in which the organic functional molecules and / or their starting substances are dissolved, deposited on the substrate, or the substrate pulled out of the solution, so that a liquid film forms on the substrate surface. From the liquid film, the organic functional layer is then prepared by drying and / or a reaction of starting substances, such as a polymerization. The (ev) quenching substance can be easily incorporated in this embodiment of the invention by dissolving the (ev) quenching substance in a coating solution and applying it together with the active molecules or their precursors as a functional layer on the substrate.

Another way of applying organic functional layers to a substrate is to deposit them by vapor deposition. This method is particularly suitable for those functional molecules of the functional layer which have low molecular weights. In this case, according to a development of this embodiment of the invention, the (e-v) quenching substance can be deposited by co-evaporation together with the active molecules of the organic functional layer in order to introduce the quenching substance into this layer.

In order to introduce the (e-v) quenching substance into the organic functional layer, the (e-v) quenching substance may also be present outside the organic functional layer and then diffuse into it.

For this purpose, the (ev) quenching substance can advantageously also be applied in a separate layer before or after the application of the organic functional layer, ie as a support or covering of the organic functional layer become. The quenching substance may then at least partially diffuse from the separate layer into the organic functional layer. In this case, the separate layer can also dissolve, for example.

Options include:

Applying a preferably thin layer with the (e-v) quenching substance -with or without matrix-, for example by printing with ink-jet technology, superposition of this layer with a

Layer of a solution containing the organic material of the organic functional layer, dissolution of the (ev) quenching substance layer by the solvent of the organic functional layer, mixing by diffusion of the materials in the liquid phase and subsequent formation of the organic functional layer with the ( ev) - Extinguishing substance by removal of the solvent and / or crosslinking. Also the reverse order is possible.

Application of a preferably thin layer of the (e v) -resolating substance with or without matrix. Overlaying this layer with a layer of a solution containing the material of the organic functional layer, but with solvents in which the (e- v) quenching substance is not soluble, i. Training a separate film. Subsequently, diffusion of the (e-v) quenching substance into the organic functional layer is also carried out, for example, assisted by suitable measures, such as optical or thermal excitation or activation. Also the reverse order is possible.

^• transfer of the (ev) in the organic functional layer by applying the (ev) - quenching substance as a layer on a support, "face-to-face" - Coverage of the organic functional layer with the carrier, ie in juxtaposition Arranging carrier and functional layer with contact of carrier and layer or non-contact. The release of the (ev) - extinguishing substance on the support can be effected by thermal and / or optical action, for example, locally, for example by irradiation with a laser. Subsequently finds. Diffusion of (ev) quenching substance into the organic functional layer instead. As a result, the quenching substance can also be deposited in a structured manner in a simple manner.

According to another embodiment of the invention, it is intended to encapsulate the organic functional layer in a cover, the (e-v) quenching substance being trapped in the cover and then being present within the cover. The cover may in particular also form a cavity in which the (e- v) quenching substance is present. The (e-v) quenching substance trapped in the cavity can then partially diffuse into the organic functional layer as well.

It is also possible that the singlet oxygen formed in the organic functional layer is diffused into the cavity and thus to the (ev) quenching substance and deactivated there, so that an equilibrium of ground-state and singlet oxygen is established throughout the component which is harmless to the component or at least reduces the amount of singlet oxygen present in the component.

Another possibility, directly or via diffusion (ev) - to introduce Löschsubstanzen in the component is the storage in a structured insulation or resistance layer between two electrode layers of the Component, which serves for local interruption or attenuation of the current flow.

Also, according to another embodiment of the invention, a barrier layer having an (e-v) quenching substance which protects the organic functional layer can be applied. This can also act as a barrier to prevent or at least slow down the penetration of further oxygen or moisture.

Further embodiments of the invention, in which an (ev) quenching substance is introduced outside the organic functional layer into the component, envisage using a substrate which contains an (ev) quenching substance or in which a film having a (ev) -

Extinguishing substance is applied. Again, the film or substrate can neutralize singlet oxygen that diffuses into or out of the substrate or film. In this case, for effective protection of the organic functional layer, the film or the substrate may be in contact with the at least one organic functional layer in order to reduce diffusion paths up to a neutralization of the singlet oxygen.

Organic components often also have adhesions, for example in order to connect an encapsulation to a substrate of the component. A development of the invention provides that an adhesive is used for bonding at least one part to the substrate, which contains an (ev) quenching substance. One such refinement offers, inter alia, the advantage that it is also possible to use (ev) extinguishing substances which, if they were arranged within the functional layer, would be the Properties of the organic functional layer would adversely affect.

In order to keep the influence of the (ev) quenching substance on the organic functional layer as low as possible, it is furthermore advantageous if the HOMO and LUMO states of the molecules of the (ev) quenching substance have a higher energy distance than the HOMO and HOMO LUMO states of the active molecules of the organic functional layer have.

It is also possible to introduce an (e-v) quenching substance in the form of particles. The particles can be very small and therefore also include in particular nanoparticles. Within the meaning of the invention, particles are understood as meaning not only solid particles but also liquid or gel-like droplets which are, for example, dispersed or emulsified. The particles may consist of, or contain the (e-v) quenching substance itself, for example, on the surface or have OH groups on the surface.

Advantageously, further measures can be provided to protect the organic electrical or electronic component from the action of oxygen and other reactive substances. Another effective protection is a getter material for water and / or oxygen.

The invention is suitable for a variety of applications and. Thus, the organic electrical or electronic component can at least one of the elements

an organic transistor,

an organic diode,

an organic opto-electronic sensor, an organic storage element, for example a PFRAM (random access memory with ferroelectric polymer)

- include an organic RF-ID tag. In particular, according to the invention whole organic circuits, such as for an aforementioned

Identification labels are produced using organic components according to the invention.

Also for the production of organic photovoltaic or solar cells, the invention is ideally suited.

In particular, the formation of singlet oxygen is promoted by the sunlight, so that just for use as a solar cell, the inventive use of (e-v) quenching substances is beneficial.

For the production of solar cells or optoelectronic sensors, for example, an organic functional layer can be applied with a photovoltaically active organic substance. For example, anthocyanins are known as such substances.

For the production of organic electronic components, according to an embodiment of the invention, in particular at least one organic semiconductor layer is applied. Particularly polycyclic hydrocarbons, here preferably acenes, such as tetracene, pentacene or hexacene, have proven to be useful here. Pentacene is a common material for organic thin-film transistors. However, these acenes are all very sensitive to oxidation, so that the use according to the invention of additional (e-v)

Extinguishing substances is particularly advantageous here. Although the acenes themselves are known as quencher for singlet oxygen, the mechanism of deactivation does not take place via an electronic-vibronic energy transfer, but via a chemical deactivation, which makes these substances just so sensitive to oxidation. By contrast, the (ev) extinguishing substances used according to the invention do not react with the singlet oxygen.

In the following the invention with reference to embodiments and with reference to the drawings is explained in more detail, wherein the same and similar elements are provided with the same reference numerals and the features of various embodiments can be combined.

Show it:

1 shows a first exemplary embodiment of an organic electrical or electronic component according to the invention designed as an optoelectronic sensor, FIG. 2 shows a further exemplary embodiment of an organic electrical or electronic component according to the invention designed as an optoelectronic sensor,

3 shows an exemplary embodiment of a component according to the invention designed as a thin-film transistor, FIG. 4 shows an exemplary embodiment of an inventive component

Device with memory cells,

FIG. 5 is a schematic state diagram showing HOMO and LUMO states of the organic layer active molecules and the (e-v) quenching substance. FIG. 6 is a variant of that shown in FIG

Embodiment with a (ev) - extinguishing substance-containing film, and Fig. 7 embedded in the organic functional layer particles with a (ev) - extinguishing substance. 1 shows a first exemplary embodiment of an organic electrical or electronic component designated as a whole by the reference numeral 1. In the embodiment shown in Fig. 1, an optoelectronic sensor is shown in particular.

The layer structure of the sensor, as shown schematically in FIG. 1, comprises a layer sequence with an organic photovoltaic layer having an organic photovoltaically active material, which is arranged between two electrode layers of the layer sequence.

In addition, further functional layers can be provided between the electrode layers in order, among other things, to increase the quantum efficiency. For example, a so-called hole transport layer can be used to compensate for the different mobilities of holes and electrons produced.

The component 1 comprises a substrate 3-for example made of glass or plastic-with sides 31, 32, on which a transparent electrode layer 7 is deposited. As the transparent electrode layer 7, for example, the conductive transparent indium-tin oxide comes into question. On the coated with the electrode layer 7 side 31 of the substrate is deposited as an organic functional layer 5, a layer having an organic photovoltaically active substance.,

The layer 5 can be, for example, a polymer layer which is applied by means of liquid coating. Likewise, however, the organic functional layer 5 can also be vapor-deposited. As mentioned above, further functional layers in the layer sequence between the Electrode layers 7, 9 may be present. These are known in the art and not shown for the sake of clarity in Fig. 1.

On the first electrode layer 7 and the organic functional layer 5 provided side 31 of the substrate, a further electrode layer 9 is applied. The electrode layer 9 is preferably a metal layer having an electronic work function different from the first electrode layer 7. It is favorable to choose for the electrode layer 9 a material with a work function which is lower than the work function of the first electrode layer 7. Suitable materials include aluminum, barium or calcium. Other materials are known in the art. However, the layer sequence can also be designed inversely, wherein a transparent cover is provided on the substrate, through which the light to be detected can enter.

Due to the different work functions migrate in the functional layer 5 generated electrons and holes to the electrodes, so that a voltage can be tapped.

The suitable organic photovoltaic effective

Materials are typically oxygen sensitive. Likewise, the electrode layer 9 can also oxidize. In order to protect the sensitive layers 5, 9, in the embodiment shown in Fig. 1, a cover 11 with the substrate 3 to form splices or

Glued bonds 13 glued. The cover 11 includes a cavity 12 a. As a further protective measure for the layers 5, 9, a getter material 15 for water and / or oxygen is also present within the cavity 12 on the cover 11. As getter 15 is under suitable for other calcium oxide. Other coverage methods and designs are known to those skilled in the art.

According to the invention is in the form of a photocell organic device 1 also has a (e-v) -

Extinguishing substance 4 for singlet oxygen present. The extinguishing substance 4 may in particular be present in the functional layer 5, as shown in FIG. 1. One possibility for introduction into the layer 5 is, in the case of a liquid coating of the side 31 of the substrate 1, simply to dissolve the (e-v) -exiting substance 4 in the polymeric or dendrimeric solution to be applied and to apply it together with the other component or components of the layer. Another possibility is to deposit the (e-v) quenching substance 4 in a vapor-deposited layer 5 by co-evaporation together with the active molecules-in an organic photo or solar cell, for example photovoltaically active molecules-of the functional layer 5.

Another possibility for introducing the (e-v) -exchanging substance 4 into the functional layer 5, which may alternatively or additionally be provided, is to introduce the (e-v) -substituting substance 4 within the cover 11 which encapsulates the functional organic layer 5. The quenching substance 4 is then present in the cavity 12 formed by the cover. If the molecules of the quenching substance 4 have a sufficiently low molar mass, then the molecules can also diffuse into the functional layer 5 in sufficient quantity while establishing an equilibrium vapor pressure.

The (ev) quenching substance can also be applied in a separate layer before or after the application of the layer 5. From this separate layer, the quenching substance 4 can then at least partially into the organic Diffuse layer 5. The separate layer can also dissolve completely.

Also, as shown in FIG. 1, the (e-v) quenching substance 4 alternatively or additionally in the

Gluing 13 may be present, for example, by a glue containing the quenching substance 4 is used when gluing the cover 11 adhesive.

FIG. 2 shows a further exemplary embodiment of an organic electrical or electronic component 1 according to the invention. The component 1, like the component shown in FIG. 1, may have a cover 11. However, the cover or other encapsulations are omitted for the sake of clarity in Fig. 2.

In this embodiment, a conductive barrier layer 17 for the functional organic layer 5 is additionally provided on the conductive transparent electrode layer 7. Between the electrode layers 7 and 9 there is also a hole transport layer 19 as further functional layer to increase the quantum efficiency.

Indium tin oxide as a transparent conductive electrode layer 7 releases oxygen over time. The barrier layer serves as an oxygen barrier to prevent or slow down the penetration of oxygen into the functional layers 5 and 19. In order to improve the protection of the organic functional layer 5 and / or the hole transport layer 19, it is further provided in this embodiment that the barrier layer 17 contains an (ev) quenching substance. Additionally, as shown in FIG. v) quenching substance may also be incorporated in the organic functional layer 5.

The exemplary embodiments illustrated with reference to FIGS. 1 or 2 are also known, for example, as

Solar cells or using a plurality of sensor elements on a substrate 3 can also be used as an image sensor.

FIG. 3 shows an exemplary embodiment of an organic thin-film transistor 1.

In this embodiment, a doped silicon substrate 3 is used. The substrate may be p-doped, for example. The surface of the side 31 of the substrate 3 is oxidized, so that a silicon oxide insulating layer 21 is formed. On this layer 21, source and drain electrodes 23, 25 are applied. These electrodes can be produced, for example, by photolithographic patterning of a gold layer. On the electrodes 23, 25, a further insulating layer 27 may be applied to isolate adjacent transistor elements on the substrate 3 against each other. Furthermore, an organic functional layer 5 is applied on the side 31 which is insulated in contact with the electrodes 23, 25 and by means of the insulating layer 21 with respect to the gate, for example p-type silicon of the substrate 3.

Suitable materials for the organic functional layer 5 or as active molecules of the layer 5 include pentacene and / or thiophenes, such as quaterthiophene or sexithiophene. Also in this embodiment of the invention is the (ev) - Extinguishing substance in layer 5 in mixture with the active molecules. As with the exemplary embodiments explained with reference to FIGS. 1 and 2, the (ev) quenching substance is preferably present in the layer 5 in a concentration of at most 5 percent by weight, more preferably of at most 1 percent by weight of the active substance.

If an organic ferroelectric polymer is used in the organic functional layer 5, the embodiment shown in FIG. 3 can also serve as an organic RAM memory cell.

Instead of a silicon substrate, in the example shown in Fig. 3, a polymer or

Plastic substrate can be used. The coating with the organic functional layers can then advantageously be carried out, for example, for mass production in a roll-on-roll coating process. The layer structure of components for such manufacturable circuits is known in the art. With such a method, for example, electronic circuits for RF-ID labels can be produced.

4 shows an exemplary embodiment of an organic component 1 according to the invention with a memory cell arrangement with PFRAM cells. On a substrate 3 to metal lines 35 are arranged. These can be vapor-deposited or sputtered on, for example, in thin-film technology. The substrate 1 is also coated on the side with the metal lines 35 with an organic functional layer 5. On this layer 5 further metal lines 37 are applied, which extend transversely to the metal lines 35 and are separated from them by the layer 5. The organic functional Layer 5 may again be, for example, a ferroelectric polymer layer. By applying a voltage between each one of the metal lines 35 and 37, the ferroelectric material can be polarized in the region between the lines to impress a bit information. Again, according to the invention, an (ev) quenching substance 4 is contained in the layer 5 in order to protect the polymer molecules of the layer 5 from a reaction with singlet oxygen.

The selection of suitable (e-v) quenching substances advantageously also takes place on the basis of the distances between the electronic states of the active molecules and the molecules of the (e-v) quenching substance. Fig. 5 shows for clarity a schematic state diagram. The solid lines represent the highest occupied molecular orbital ("HOMO") and the lowest unoccupied molecular orbital ("LUMO") of the active molecules. The dashed lines indicate the HOMO and LUMO states of the molecules of the (e-v) quenching substance. In order to keep the influence on the electrical and / or electro-optical properties of the active layer as small as possible, the (ev) quenching substance is selected so that, as shown in the diagram, the HOMO and LUMO states of the molecules of (ev) - Extinguishing substance have a higher energy gap than the HOMO and LUMO states of the active molecules of the organic functional layer.

If the LUMO states of the molecules of the (e-v) quenching substance are too low, they can be used as trap states for

Electrons act, which flow through the layer. Likewise, energetically high HOMO states of the molecules of the (ev) quenching substance can act as traps for holes. In both cases, for example, the flow of current through the layer can be adversely affected. Also can In a functional organic layer 5, as it is present in the exemplary embodiments of FIGS. 1 and 2, this drop action leads to a lowering of the quantum efficiency.

In order to achieve efficient quenching of singlet oxygen, the (e-v) quenching substance is further preferably selected to contain molecules having at least one functional group having a terminal oscillator whose vibrational energy is that of

Fundamental vibration or an overtone of the stretching vibration equal to the energy difference between the

02 (alΔg) - and the 02 (X ^ Σ ^~ g) state of molecular oxygen or whose vibrational energy of this energy difference by more than 37%, preferably at most 10% deviates.

This condition is particularly fulfilled by molecules containing at least one hydroxyl group. Also suitable in this regard are still molecules with at least one NH or NH ₂ group, or CH bonds, but an NH bond or CH bond show a lower deactivation efficiency compared to an OH bond as a terminal oscillator. The energies of the stretching vibration are at E = 2960 cm ^"1 for a CH, E = 3355 cm ^{" 1} for an NH and 3755 cm ^"1 for an OH bond.

Suitable substances with such terminal O-H, C-H or N-H oscillators include:

monohydric or polyhydric alcohols, for example ethanol,

Ethylene glycol, glycerine, cyclohexanol;

Carbohydrates, for example mono-, di- and trisaccharides; Cellulose derivatives and / or starch derivatives, for example cellophane;

Glycerol monooleate, for example glycerol monooleate, glycerol monooricinoleate, glycerol monostearate; amino alcohols; polyamines; Polyamides.

Cellulose derivatives, starch derivatives, polyamines and polyamides are also examples of an (e-v) quenching substance comprising a polymer having hydroxyl groups or NH or NH 2 groups. Such (e-v) quenching substances may be used, for example, in the form of a film or substrate for the organic functional layer in the organic device. For example, the substrate 3 of the embodiments shown in FIGS. 1 or 2 may comprise such a polymer.

An embodiment with a film with a polymeric (e-v) quenching substance, Fig. 6. This

Embodiment is a variant of the OLED shown in Fig. 1. The layers 5, 7, 9 of this organic component-here again an optoelectronic sensor or a solar cell, such as the examples shown in FIGS. 1 and 2-are covered with a film 29 of polymeric (ev) quenching substance arranged inside the cover 11 , The film 29 may be fixed, for example, as shown in Fig. 6, with the bonds 13. As the ev (ev) quenching substance 4 for the film, polyimide, polyamide, or a starch or cellulose derivative such as cellophane may be used, inter alia. In addition, (ev) quenching substance may also be present in the bond 13 and / or the cavity. Other than shown in Fig. 6, the organic device may be constructed so that the film 29 or the substrate having the (ev) quenching substance is in contact with the organic functional layer 5.

It is also possible to use an (ev) quenching substance in the form of particles. Fig. 7 shows an example of such a (ev) quenching substance in particulate form. The (ev) - quenching substance 4 of this embodiment comprises nanoparticles 41, ^"which in the organic functional

Layer 5 are embedded. The nanoparticles 41 comprise molecules 42 having a non-polar end 43 symbolized by a dash and one or more circle-symbolized hydroxy groups at the other end of the molecule 42. Examples of such molecules include monohydric alcohols, such as ethanol, propanol or hexanol.

Hydroxy groups increase the polarity of the molecule 42, which generally degrades solubility in an organic non-polar environment.

On the other hand, hydroxy groups are eminently suitable as terminal oscillators to deactivate singlet oxygen or to convert it into the triplet ground state.

In the form of particles, as shown by way of example in FIG. 7, molecules with poor solubility can now also be embedded in an organic functional layer. In this case, the nonpolar radicals 43 of the molecules 42 in the particle to the outside, so that the polar OH groups are in the interior of the particles 41. In this way, even further molecules 45 of the (ev) quenching substance can be embedded inside the particles 41, which only poorly insulates because of the high number of polar OH groups or not at all soluble in the active organic layer 5.

The singlet oxygen is in this embodiment, especially during the

Diffusion by the nanoparticles 41 impact-induced deactivated.

It will be apparent to those skilled in the art that the invention is not limited to the exemplary ones described above

Embodiments is limited, but rather can be varied in many ways. In particular, the features of the individual embodiments can also be combined with each other.

LIST OF REFERENCE NUMBERS

I Organic component

3 substrate

4 (e-v) quenching substance

5 organic functional layer

7 conductive transparent electrode layer

9 electrode layer

II cover

12 cavity

13 bonding

15 getter material

17 barrier layer

19 hole transport layer

21 Siθ ₂ insulation layer

23, 25 electrodes 7 insulation layer 9 polymer film 1.32 page from 3 5, 37 metal lines 1 nanoparticles 2, 45 molecules of 4, 41 3 nonpolar end of 42, 4 hydroxy group

Claims

claims

1. Organic electrical or electronic component having at least one organic functional layer, characterized by a particular organic (e-v) quenching substance for singlet oxygen.

2. Organic electrical or electronic

Component according to Claim 1, characterized in that the molecular weight of the (e-v) quenching substance is less than 528 g / mol, preferably less than 374 g / mol, particularly preferably less than 178 g / mol.

3. An organic electrical or electronic component according to claim 1 or 2, characterized in that the (e-v) quenching substance contains molecules having at least one functional group with a terminal oscillator with a vibration energy of the fundamental or a harmonic of the stretching vibration, which is equal to

Energy difference between the 02 (alΔg) - and the

O2 (χ3Σ ^~ g) state of molecular oxygen or its vibrational energy from it

Energy difference by more than 37%, preferably deviates by more than 10%.

4. Organic electrical or electronic component according to one of the preceding claims, characterized in that the (ev) quenching substance molecules having at least one functional group with a terminal oscillator with a vibrational energy of an overtone of the Stretching vibration with n <= 3, which equals the energy difference between the O2 (H ¹ Ag) - and the

O2 (X ^ Σ ^' g) state of molecular oxygen or whose vibrational energy of this energy difference differs by at most 37%, preferably at most 10%.

5. Organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (e-v) -

Extinguishing substance contains organic molecules having at least one hydroxyl group.

6. Organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (e-v) - extinguishing substance contains molecules with at least one NH or NH2 group.

7. Organic electrical or electronic

Component according to at least one of the preceding claims, characterized in that the (e-v) - quenching substance is a hydroxy groups or NH- or NH2-

Comprising polymers.

8. Organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (e-v) - extinguishing substance -a mono- or polyhydric alcohol or a carbohydrate.

9. Organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (ev) - Extinguishing substance is present in the organic functional layer.

10. An organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (e-v) - extinguishing substance within a cover, which encapsulates the at least one functional organic layer, is present.

11. Organic electrical or electronic component according to at least one of the preceding claims, characterized by a barrier layer with an (e-v) quenching substance.

12. Organic electrical or electronic component according to at least one of the preceding claims, characterized by a bond with a substance which consists of or includes an (e-v) quenching substance.

13. Organic electrical or electronic component according to one of the preceding claims, characterized by particles, in particular nanoparticles, which contains an (e-v) - extinguishing substance at least on the surface.

14. Organic electrical or electronic component according to one of the preceding claims, characterized in that the HOMO and LUMO

States of the molecules of the (ev) quenching substance have a higher energy gap than the HOMO and LUMO states of the active molecules of the organic functional layer.

15. An organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (e-v) - quenching substance comprises a film or a substrate for the organic functional layer.

16. An organic electrical or electronic component according to claim 15, characterized in that the film or the substrate is in contact with the at least one functional organic layer.

17. Organic electrical or electronic component according to at least one of the preceding claims, characterized in that the (ev) - extinguishing substance in a concentration of at most 5 weight percent of the active substance of the organic functional layer, preferably at most 1 weight percent is present in the organic functional layer ,

18. Organic electrical or electronic component according to one of the preceding claims, characterized by a getter material for water or oxygen.

19. Organic electrical or electronic component according to one of the preceding claims, characterized in that the (ev) quenching substance contains organic molecules having at least one hydroxyl group, wherein the ratio of total molecular weight of these molecules to the molecular weight of the hydroxy groups at most 5 to 1, preferably at most 3.5 to 1.

20. Organic electrical or electronic component according to one of the preceding claims, characterized in that the component of at least one of the elements

an organic transistor, an organic diode,

an organic optoelectronic sensor, an organic storage element, in particular a PFRAM

Includes an organic RF-ID tag.

21. Organic electrical or electronic component according to one of the preceding claims, characterized in that the component is a solar cell.

22. Organic circuit comprising at least one organic component according to one of the preceding claims.

23. A method for producing an organic electrical or electronic component, in particular an organic component according to one of the preceding claims, wherein on a substrate, at least one organic functional layer is applied, and wherein in the component additionally an (e-v) quenching substance is introduced.

24. The method of claim 23, wherein on a substrate at least one organic functional layer of the device is applied, wherein in the functional layer or in direct or direct contact with the functional layer an (ev) quenching substance is introduced.

25. The method according to claim 24, characterized in that the organic functional layer applied to the substrate by means of coating from the liquid or gel phase, in particular spin coating, dip or groove coating, or a printing technique, in particular ink-jet printing, screen printing or flexographic printing becomes.

26. The method according to claim 25, characterized in that the (e-v) quenching substance dissolved in a coating solution and applied together with the active functional molecules or their starting materials as an organic functional layer on the substrate.

27. The method according to any one of the preceding claims, characterized in that at least one organic functional layer is deposited by vapor deposition.

A method according to claim 27, characterized in that the (e-v) quenching substance is deposited by co-evaporation with the active molecules of the organic functional layer.

29. A method according to any one of the preceding claims, wherein the organic functional layer is encapsulated in a cap, characterized in that the (e-v) quenching substance is trapped in the cap.

30. The method according to any one of the preceding claims, characterized in that a barrier layer is applied, which contains an (ev) quenching substance.

31. A method according to any one of the preceding claims, wherein a substrate is used which contains an (e-) quenching substance or in which a film with an (e-v) quenching substance is applied.

32. The method according to any one of the preceding claims, wherein at least a part is adhered to the substrate, characterized in that an adhesive is used with an (e-v) quenching substance.

33. Method according to one of the preceding claims, characterized in that the (e-v) quenching substance diffuses into the at least one organic functional layer.

34. The method according to claim 33, characterized in that the (e-v) quenching substance is applied in a separate layer before or after the application of the electroluminescent layer.

35. The method according to any one of the preceding claims, characterized in that an (e-v) quenching substance is introduced which contains molecules having at least one hydroxyl group or having at least one NH or NH2 group or a C-H bond.

36. The method according to any one of the preceding claims, characterized in that an (e-v) quenching substance is introduced, which contains an alcohol.

37. The method according to any one of the preceding claims, characterized in that an (ev) quenching substance which comprises a polymer having hydroxyl groups or NH or NH 2 groups.

38. The method according to any one of the preceding claims, characterized in that the (e-v) quenching substance is introduced in the form of particles.

39. The method according to any one of the preceding claims, characterized in that an organic functional layer is applied with a photovoltaically active organic substance.

40. The method according to any one of the preceding claims, characterized in that an organic semiconductor layer, in particular with a polycyclic hydrocarbon is applied.

41. Use of (e-v) quenching substances, in particular having a molecular weight of less than 528 g / mol in organic electrical or electronic components.