Electronic device

Abstract

The present application relates to an electronic device, preferably an OLED, characterized in that it comprises a stack of two layers, the stack of two layers sharing one layer. The invention also relates to a method for producing such an electronic device and to a mixture which can be used for producing such an electronic device.

Description

[0001] The present invention relates to an electronic device, characterized in that it comprises a stack of at least two layers, wherein the two stacks of layers share a layer common to the two stacks of layers, the layer comprising a hole transport compound, a low HOMO level compound and a p-type dopant. Each of the stacks of layers is an organic electroluminescent device and / or represents a pixel of a display based on an organic electroluminescent device.

[0002] Organic electroluminescent devices, also known as organic light-emitting diodes (OLEDs), are electronic devices comprising one or more layers, at least one of which comprises an organic compound, that emit light when a voltage is applied. The general principles of the construction and function of OLEDs are known to those skilled in the art.

[0003] While OLEDs have continued to develop over the years, resulting in significant improvements compared to earlier generations, their performance still needs further improvement. Lifespan, efficiency, operating voltage, and color purity are particularly important performance parameters for both high-tech and commercial applications. Completely satisfactory solutions have yet to be found in these areas.

[0004] In order to ensure a good, i.e. sufficiently low, driving voltage, a stack design in which the OLED comprises a layer that contains a p-type dopant and is shared by a stack of two or more separate layers is extremely beneficial and frequently used in the art. Such a shared layer is often referred to as a common layer and is understood in the art to be a layer that extends laterally over a stack of at least two pixels or layers of an OLED, thereby covering at least two separate light-emitting layers. In other words, the common layer is shared by a stack of at least two pixels or layers.

[0005] Such a shared layer comprising a p-type dopant is typically a hole injection layer and / or a charge generation layer. If such a shared p-type doped layer is present in an OLED, it has been observed that when the OLED is driven, i.e. driven under a voltage, a current is generated in a lateral direction perpendicular to the stacking axis of the stack of layers. Such lateral currents, also called leakage currents, result in poor colour purity of the OLED display due to unwanted illumination of adjacent stacks or pixels when a voltage is applied to the stack to switch it on. This lateral (leakage) current phenomenon occurs in particular when one or more stacks with a low threshold voltage are in close proximity to a stack with a high threshold voltage. Due to the reduced colour purity it is extremely desirable to reduce the occurrence of such lateral currents.

[0006] The present invention provides a solution to this problem by reducing the lateral current between adjacent stacks or pixels. Preferably, this reduction in lateral current is achieved without affecting other performance parameters, particularly drive voltage, efficiency, and lifetime, and most importantly, drive voltage. Thus, the present invention achieves a reduction in lateral current in a p-type doped layer shared by two or more stacks or pixels of OLED layers while maintaining a low drive voltage for the stack of OLED layers.

[0007] Thus, one embodiment of the present invention is an electronic device comprising a stack of a first layer and a stack of a second layer in close proximity to the stack of the first layer, the first stack and the second stack each comprising an anode, a cathode, and a layer A located between the anode and the cathode and a light-emitting layer, wherein layer A is shared by the two stacks of layers, and wherein layer A comprises:

[0008] ■ at least one compound C1 having hole-transporting properties;

[0009] ■ at least one compound C2 having a HOMO less than -5.1 eV; and

[0010] ■ At least one compound C3 which is a p-type dopant.

[0011] The electronic device according to the present invention is preferably an arrangement of at least two separate organic electroluminescent devices, wherein each stack of two layers represents a separate organic electroluminescent device. The electronic device preferably comprises not only the stack of the first layer and the stack of the second layer described above, but also a plurality of such stacks, with "plurality" referring to stacks in the millions. Preferably, layer A is shared by all stacks that form part of the display light-emitting area of the electronic device according to the present application.

[0012] An organic electroluminescent device, as defined herein, is an electronic device having one or more layers, at least one of which comprises an organic compound, and which emits light when a voltage is applied between its anode and cathode. Another common term for an organic electroluminescent device is an organic light-emitting diode, abbreviated as OLED.

[0013] "Close proximity" in the above definition means that the distance between the stacks of two layers is preferably 5 to 40 μm, more preferably 10 to 30 μm, and even more preferably 15 to 35 μm, wherein the distance is measured from the anode side of the first stack closest to the anode side of the second stack to the anode side of the second stack closest to the first stack.

[0014] "HOMO" in relation to a compound in this application refers to the highest occupied molecular orbital of the compound, as determined in Working Example E).

[0015] "Less than" with respect to energy levels such as the HOMO, like "lower than," means an increase in the absolute value of the energy in eV. In this sense, -5.5 eV is both "less than" and "lower than" -5.4 eV. "Greater than" with respect to energy levels such as the HOMO, like "higher than," means a decrease in the absolute value of the energy in eV. In this sense, -5.4 eV is both "greater than" and "higher than" -5.5 eV.

[0016] A stack of layers refers to an arrangement of multiple layers parallel to each other and stacked on top of each other. Typically and preferably, the stack of layers of an electronic device serves as a pixel of the electronic device, and the electronic device is a pixel. The pixel area is preferably the area covered by the anode. To be used as an OLED, the stack of layers needs to include at least an anode, a cathode, and a light-emitting layer located between the anode and the cathode. In existing OLEDs, there are preferably multiple layers, in particular a hole injection layer adjacent to the anode, a hole transport layer located between the hole injection layer and the anode, an electron transport layer located between the light-emitting layer and the cathode, and an electron injection layer located between the electron transport layer and the cathode and directly adjacent to the cathode. Several other layers can also be present in the stack, the most common of which are electron blocking layers and hole blocking layers. The electron blocking layer is a layer located on the anode side of the light-emitting layer, directly adjacent to the light-emitting layer. Its purpose is to prevent electrons from leaving the light-emitting layer from the anode side of the light-emitting layer. Preferably, it has a relatively high LUMO (LUMO = lowest unoccupied molecular orbital). The hole blocking layer is a layer located on the cathode side of the light-emitting layer, directly adjacent to the light-emitting layer. Its purpose is to prevent holes from leaving the light-emitting layer from the cathode side of the light-emitting layer. Typically, they have a relatively high HOMO (HOMO=highest occupied molecular orbital).

[0017] The stack of first layers and the stack of second layers of the electronic component are preferably arranged parallel to one another, which means that the individual layers of the stack of first layers are parallel to the individual layers of the stack of second layers and vice versa.

[0018] A specific embodiment of the stack of OLED layers used in the device according to the invention is a so-called tandem stack, which comprises two or more light-emitting layers which are arranged in sequence, i.e. one after the other, in a stack of OLED layers. Tandem stacks are generally known to those skilled in the art. A tandem stack preferably consists of two or more, preferably two or three, layer sub-stacks which are stacked one on top of the other, wherein a charge generation layer (CGL) is located in each case between the respective sub-stacks, and the resulting combined stack is located between the anode and the cathode. In this case, the sub-stacks preferably each comprise a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer. Figure 2A A representative example of a stack of tandem layers is shown. Figures 2B-2DA representative example of an electronic device according to the present application is shown, comprising a stack of two layers, each of which is a stack of OLED tandem layers.

[0019] According to a preferred embodiment of the present invention, the stack of at least one layer of the electronic device, preferably the stack of the first layer and the stack of the second layer of the electronic device, is a tandem stack, preferably as defined above.

[0020] According to an alternative preferred embodiment of the present invention, at least one, preferably two, layer stacks of the electronic device are regular non-tandem layer stacks. Regular non-tandem layer stacks here mean that they comprise a single light-emitting layer located between an anode and a cathode.

[0021] In existing displays, stacks of multiple OLED layers are placed in close proximity to each other and preferably have layers that are parallel to each other. In order for the display to work properly, the stacks of layers must be driven independently of each other, i.e. turned on and off. In a preferred embodiment, each individual stack of layers represents a pixel of the display. In the stack of individual layers described above, at least one electrode and light-emitting layer is separated from the corresponding electrodes and light-emitting layers of the stack of other layers. Other layers can also be separated from the corresponding layers in the stack of other layers to which they functionally correspond. In particular, it is preferred that the corresponding light-emitting layers of the stack of individual layers are separated from the respective light-emitting layers of the stack of other layers in the electronic device. However, in existing OLEDs, not all layers of the stack of individual layers are separated from each other. In addition to one of the electrodes, which is preferably shared by the stack of layers, there is preferably also a hole injection layer, which is shared by the stack of layers. Other layers, such as hole transport layers, electron transport layers and electron injection layers, are preferably also shared. In a tandem stack, it is preferred that the charge generation layer (CGL) is a shared layer.

[0022] Figure 1 A representative electronic device is shown where the shared layer is a hole injection layer, where the stack of layers is a stack of non-tandem layers, and Figure 2B and 2D A representative electronic device is shown where the shared layer is a hole injection layer, where the stack of layers is a stack of tandem layers.

[0023] Figure 2C and 2D A representative electronic device is shown where the shared layer is a charge generation layer, and the stack of layers is a stack of tandem layers.

[0024] According to a preferred embodiment, layer A is selected from: layer A1 adjacent to the anode; and layer A2, said layer A2 being located between a light-emitting layer of a stack and another light-emitting layer, said stack of other light-emitting layers being stacked on top of the light-emitting layer in the same stack. Layer A2 is preferably part of a tandem stack, in particular, it is a charge generation layer of the tandem stack or a sublayer of a charge generation layer of the tandem stack. Layer A1 is preferably a hole injection layer. According to other preferred embodiments, two layers A are present in the electronic device, one of which is layer A1, preferably a hole injection layer, and the other is layer A2, preferably a charge generation layer of the tandem stack or a sublayer of a charge generation layer.

[0025] According to a preferred embodiment, the electronic device has Figure 1 The structure shown.

[0026] In this structure, 2a and 2b are two stacks of layers of the electronic device 1, which are close to each other and preferably have layers parallel to each other. The stacks 2a and 2b of layers are located on a common substrate layer 3. Layer 4a (the anode of the stack of the first layer) and layer 6a (the light-emitting layer of the stack of the first layer) are separate layers of the stack 2a of the first layer. Layer 4b (the anode of the stack of the second layer) and layer 6b (the light-emitting layer of the stack of the second layer) are separate layers of the stack 2b of the second layer. The cathode 7 is shared by the stacks 2a and 2b of the two layers. Layer 5 is a HIL and is shared by the stacks of the two layers. According to the present application, layer 5 is preferably layer A. The dots represent optional additional layers that may be present between the layers explicitly shown.

[0027] Figure 2AThe structure of a stack of single tandem OLED layers is shown. The stack of layers 8 comprises light-emitting units 9a and 9b, which are stacked on top of each other between an anode 4 and a cathode 7 and which are separated by a charge generation layer 10. The composition of the light-emitting units 9a and 9b themselves is similar to that of a stack of conventional OLED layers, but without the anode and cathode. They typically comprise, in sequence, a hole injection layer 5, a hole transport layer 11, a light-emitting layer 6, an electron transport layer 12 and an electron injection layer 13. It should be noted that in addition to the layers shown, other layers may be present in the light-emitting unit. In a preferred embodiment, the charge generation layer may serve as the electron injection layer and the hole injection layer of adjacent sub-stacks, respectively, so that there is no hole injection layer on the cathode side of the charge generation layer and no electron injection layer on the anode side of the charge generation layer. The two light-emitting units of the series stack preferably comprise the same functional layers in the same order, but may also have different functional layers and / or a different order of functional layers. The light-emitting layer composition of each light-emitting unit is preferably different from the light-emitting layer composition of one or more other light-emitting units. For example, one light-emitting unit may have a light-emitting layer that emits red light, while another light-emitting unit may have a light-emitting layer that emits blue light. The dots represent optional additional layers that may be present between the layers explicitly shown. According to a preferred embodiment, the stack of tandem layers includes a third light-emitting unit in addition to the light-emitting units 9a and 9b.

[0028] According to an alternative preferred embodiment, the electronic device has Figure 2B According to this structure, the two layer stacks 2a and 2b of the device are each a tandem stack, i.e. a stack comprising two or more light-emitting layers. Figure 2B In the electronic device 1, the hole injection layer 5 is a shared layer. In addition to substrate 3, the device also includes two separate anodes 4a and 4b, a shared cathode 7, two first light-emitting layers 6a and 6b separated between the two stacks, two second light-emitting layers 14a and 14b separated between the two stacks, and two charge generation layers 10a and 10b separated between the two stacks. The shared hole injection layer 5 is preferably layer A. Dots represent optional additional layers that may be present between the explicitly shown layers.

[0029] According to an alternative preferred embodiment, the electronic device has Figure 2C According to this structure, the two layer stacks 2a and 2b of the device are each a series stack, i.e. a stack comprising two or more light-emitting layers arranged in sequence. Figure 2CIn the electronic device 1 of FIG. 1 , there are two separate hole injection layers 5a and 5b: layer 5a of the stack for the first layer and layer 5b of the stack for the second layer. In addition to substrate 3, the device also comprises two separate anodes 4a and 4b, a shared cathode 7, two first light-emitting layers 6a and 6b separated between the two stacks, two second light-emitting layers 14a and 14b separated between the two stacks, and a shared charge generation layer 10, which is preferably layer A. The dots represent optional additional layers that may be present between the layers explicitly shown.

[0030] According to an alternative preferred embodiment, the electronic device has Figure 2D According to this structure, the two layer stacks 2a and 2b of the device are each a tandem stack, i.e. a stack comprising two or more light-emitting layers. Figure 2D In the electronic device 1 of FIG. 3 , there is a shared hole injection layer 5, which is preferably layer A. In addition to substrate 3, the device comprises two separate anodes 4 a and 4 b, a shared cathode 7, two first light-emitting layers 6 a and 6 b separated between the two stacks, two second light-emitting layers 14 a and 14 b separated between the two stacks, and a shared charge generation layer 10, which is preferably layer A. The dots represent optional further layers that may be present between the layers explicitly shown.

[0031] Detailed description of an electronic device comprising side-by-side stacks of layers emitting light of different colors

[0032] This embodiment is also referred to as an RGB side-by-side design. It preferably comprises a stack of three layers, preferably parallel to one another and arranged in close proximity within the electronic device. A first layer of the stack comprises a blue light-emitting layer, a second layer of the stack comprises a green light-emitting layer, and a third layer of the stack comprises a red light-emitting layer. Each layer stack in this electronic device has only one light-emitting layer and is therefore not a series stack. Figure 1 An example of an electronic device of this design is shown, however, where only two layers are depicted as a stack, rather than a full stack of three layers as part of an RGB side-by-side design of the electronic device. The following preferred embodiments apply to this design case:

[0033] Layer A, preferably a hole injection layer, preferably has a thickness of 5 to 20 nm. Furthermore, preferably, Layer A, preferably a hole injection layer, comprises compounds C1, C2, and C3. "Composed of" herein means that, with the exception of minimal impurities inevitably generated during compound synthesis and application, no other compounds are present in the layer.

[0034] The compounds of layer A, which serves as layer A1, are preferably all small-molecule compounds, in particular, non-polymeric compounds. Compounds C1, C2, and C3 are preferably small-molecule compounds, in particular, non-polymeric compounds. Small-molecule compounds are preferably understood to have a molecular weight of less than 2000 g / mol, more preferably less than 1000 g / mol.

[0035] The HOMO of compound C1 is preferably greater than -5.0 eV, more preferably greater than -4.9 eV, most preferably greater than -4.85 eV. The HOMO values are in each case measured as described in section E) of the working examples.

[0036] It is understood that compound C1 itself, if placed in a layer, has either a high or low lateral current. Generally, compound C1 preferably has a low lateral current. Regardless of whether compound C1 alone (if present in a layer) has a high or low lateral current, the technical effects of the present invention can be achieved. However, if compound C1 has a low lateral current, the absolute value of the lateral current exhibited by the device will generally be lower. Therefore, if obtaining the lowest possible lateral current is a priority in device design, it is generally preferred to select compound C1 with a low lateral current.

[0037] Compound C1 is preferably selected from the group consisting of triarylamines, in particular monotriarylamines and bistriarylamines, and carbazoleamines. A monotriarylamine is a compound comprising a single amine group, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to the nitrogen atom of the amine group. A bistriarylamine is a compound comprising two and not more than two amine groups, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to each nitrogen atom of the two amine groups. A carbazoleamine is a compound comprising a carbazole group and an amine group, wherein the amine group is preferably a triarylamine group. A triarylamine group is an amine group wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to the nitrogen atom of the amine group.

[0038] A preferred embodiment of compound C1 conforms to one of formulas (1-1) and (1-2):

[0039]

[0040] The variables are defined as follows:

[0041] Ar 1 are selected, identically or differently on each occurrence, from: an aromatic ring system having 6 to 50 aromatic ring atoms, said aromatic ring system being surrounded by a group R 1 and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, the heteroaromatic ring system being substituted by a group R 1 replace;

[0042] Ar 2are selected, identically or differently on each occurrence, from: an aromatic ring system having 6 to 50 aromatic ring atoms, said aromatic ring system being surrounded by a group R 1 and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, the heteroaromatic ring system being substituted by a group R 1 replace;

[0043] R 1 are selected, identically or differently at each occurrence, from the group consisting of: H, D, F, C(=O)R 2 、CN、Si(R 2 )3、N(R 2 )2、P(=O)(R 2 )2、OR 2 、S(=O)R 2 、S(=O)2R 2 , linear alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more radicals R 1 can be linked to each other to form a ring; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are surrounded by groups R 2 substituted, and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R 2 C=CR 2 -、-C≡C-、Si(R 2 )2. C=O, C=NR 2 、-C(=O)O-、-C(=O)NR 2 -、NR 2 、P(=O)(R 2 ), -O-, -S-, SO or SO2;

[0044] R 2 are selected, identically or differently at each occurrence, from the group consisting of: H, D, F, C(=O)R 3 、CN、Si(R 3 )3、N(R 3 )2、P(=O)(R 3 )2、OR 3 、S(=O)R 3 、S(=O)2R 3, linear alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more radicals R 2 can be linked to each other to form a ring; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are surrounded by groups R 3 substituted, and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R 3 C=CR 3 -、-C≡C-、Si(R 3 )2. C=O, C=NR 3 、-C(=O)O-、-C(=O)NR 3 -、NR 3 、P(=O)(R 3 ), -O-, -S-, SO or SO2;

[0045] R 3 is selected, identically or differently on each occurrence, from the group consisting of: H, D, F, Cl, Br, I, CN, alkyl radicals having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more radicals R 3 may be connected to each other to form a ring; and wherein the alkyl group, aromatic ring system and heteroaromatic ring system may be substituted by one or more groups selected from F and CN.

[0046] Preferred groups Ar 1 is selected, identically or differently on each occurrence, from a monovalent radical derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, wherein each radical is replaced by a radical R 1 Preferably, the group Ar 1 a monovalent group selected, identically or differently on each occurrence, from a combination of 2 to 4 groups selected from the group consisting of benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (particularly 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, wherein each group is replaced by a radical R 1replace.

[0047] More preferred groups Ar 1 is selected, identically or differently on each occurrence, from a monovalent radical derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophene and phenyl substituted with a radical selected from naphthyl, phenanthryl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophene, carbazolyl, pyridyl, pyrimidinyl and triazinyl, wherein each of the above radicals is replaced by a radical R 1 replace.

[0048] Preferred groups Ar 2 is selected, identically or differently on each occurrence, from a divalent radical derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, wherein each radical is replaced by a radical R 1 Preferably, the group Ar 1 A divalent radical selected, identically or differently on each occurrence, from a combination of 2 to 4 radicals selected from the group consisting of benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (particularly 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, wherein each radical is replaced by a radical R 1 replace.

[0049] Still more preferred groups Ar 2 divalent radicals selected, identically or differently on each occurrence, from the group consisting of benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene (especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene), benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl and benzo-condensed dibenzothiophene, wherein each of the above radicals is replaced by a radical R 1 replace.

[0050] Preferably, R 1 are selected from the group consisting of: H, D, F, CN, Si(R 2 )3、N(R 2) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl and alkoxy groups and the aromatic and heteroaromatic ring systems are replaced by a radical R 2 replace.

[0051] Preferably, R 2 are selected from the group consisting of: H, D, F, CN, Si(R 3 )3、N(R 3 ) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl and alkoxy groups and the aromatic and heteroaromatic ring systems are replaced by a radical R 3 replace.

[0052] Preferably, R 3 is selected, identically or differently on each occurrence, from H, D, F, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms.

[0053] A particularly preferred embodiment of formula (1-1) conforms to the following formula:

[0054]

[0055]

[0056] The variable groups and tags are defined as follows:

[0057] Ar 1 、R 1 、R 2 and R 3 As defined above, and preferably in accordance with the preferred embodiments listed above;

[0058] Ar 3 Selected from: having 6 to 13 aromatic ring atoms and being surrounded by a group R 1 substituted aromatic ring system; and having 5 to 13 aromatic ring atoms and substituted by a group R 1 substituted heteroaromatic ring systems;

[0059] X is selected, identically or differently at each occurrence, from a bond, O, S, NR 1 and C(R 1 )2;

[0060] Y is selected from O and S;

[0061] n is 0 or 1, wherein when n=0, the group labeled n does not exist, and the groups bonded to the group labeled n are directly connected to each other, provided that in the case of formula (1-1-9), n is not 0.

[0062] Preferably, Ar 3 Selected from divalent radicals derived from benzene, biphenyl, naphthalene and fluorene (especially 9,9'-dimethylfluorene), wherein each radical is replaced by a radical R 1 replace.

[0063] Particularly preferred are formulae (1-1-2) and (1-1-3), among which the following formula (1-1-2-1) is particularly preferred as an embodiment of formula (1-1-2):

[0064]

[0065]

[0066] wherein the variable groups and labels are as defined above, and preferably correspond to their preferred embodiments described above.

[0067] A preferred embodiment of compound C1 conforms to the following formula:

[0068]

[0069] Among them, Ar 1 、R 1 、R 2 and R 3 As defined above, and preferably in accordance with the preferred embodiments thereof as described above. 1 The same or different selected from O, S, NR 1 and C(R 1 ) 2. The label k is 1, 2, 3 or 4, preferably 1 or 2. The label i is 1, 2 or 3, preferably 1 or 2, and most preferably 1.

[0070] Preferred specific compounds that can be used as compound C1 according to the present application are shown in the following table:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130] The specific above-mentioned compounds and other compounds suitable for use as compound C1 according to the present application, as well as methods for preparing the compounds and their use in OLED devices, are disclosed in the following publications: WO95 / 09147, WO2010 / 098458, WO2014 / 034795, KR2017-0136391, US2014-225073, US2022-115596, WO2012 / 034627, WO2013 / 120577, WO2014 / 015938, WO2019 / 115577 and Prior Art Journal of Prior Art Publishing, 2016, Issue 6, pp. 46-251.

[0131] The following definitions apply to chemical groups used as general definitions unless otherwise specifically defined.

[0132] Aryl groups are defined herein as simple aromatic rings, such as benzene, or condensed aromatic polycycles, such as naphthalene, phenanthrene, or anthracene. Condensed aromatic polycycles, as used herein, consist of two or more simple aromatic rings condensed together. Aryl groups, as used herein, contain from 6 to 40 aromatic ring atoms. Aryl groups do not contain any heteroatoms as aromatic ring atoms, but rather contain only carbon atoms as aromatic ring atoms.

[0133] A heteroaryl group herein refers to a simple heteroaromatic ring such as pyridine, pyrimidine, or thiophene, or a condensed heteroaromatic polycyclic ring such as quinoline or carbazole. A condensed heteroaromatic polycyclic ring in the sense of this application consists of two or more simple aromatic or heteroaromatic rings condensed with each other, wherein at least one of the two or more simple aromatic or heteroaromatic rings is a heteroaromatic ring. A heteroaryl group in the sense of this invention contains 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom is preferably selected from N, O, and S.

[0134] The aryl or heteroaryl radicals which may in each case be substituted by the above-mentioned radicals are in particular radicals derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, terphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthrene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthroline, benzothiophene ... Azine, pyrazole, indazole, imidazole, benzimidazole, benzimidazole [1,2-a] benzimidazole, naphthimidazole, phenanthimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, Azoles, benzophenones Azoles, naphtho Azoles, anthracenes azole, phenanthroline Azoles, isocyanates azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3- Oxadiazole, 1,2,4- Oxadiazole, 1,2,5- Oxadiazole, 1,3,4- oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole.

[0135] An aromatic ring system in the sense of the present invention is a system that does not only contain an aryl group, but it may also contain one or more non-aromatic rings that are condensed with at least one aryl group. Such non-aromatic rings contain only carbon atoms as ring atoms. Examples of groups encompassed by this definition are tetralin, fluorene and spirobifluorene. In addition, the term "aromatic ring system" is understood to include systems consisting of two or more aromatic ring systems interconnected by single bonds, such as biphenyl, terphenyl, 7-phenyl-2-fluorenyl and quaterphenyl. An aromatic ring system in the sense of the present invention contains 6 to 40 C atoms and does not contain heteroatoms as ring atoms of the ring system. An aromatic ring system in the sense of the present application does not contain any heteroaryl groups as defined above.

[0136] The definition of a heteroaromatic ring system is similar to that of the aromatic ring system described above, but differs in that it must contain at least one heteroatom as one of the ring atoms. As with aromatic ring systems, it does not necessarily contain only aryl and heteroaryl groups, but may also contain one or more non-aromatic rings condensed with at least one aryl or heteroaryl group. The non-aromatic rings may contain only carbon atoms as ring atoms, or they may also contain one or more heteroatoms, wherein the heteroatoms are preferably selected from N, O and S. An example of such a heteroaromatic ring system is benzopyranyl. In addition, the term "heteroaromatic ring system" should be understood to include systems consisting of two or more aromatic or heteroaromatic ring systems interconnected by single bonds, such as 4,6-diphenyl-2-triazinyl. A heteroaromatic ring system in the sense of the present invention contains 5 to 40 ring atoms, wherein the ring atoms are selected from carbon and heteroatoms, wherein at least one ring atom is a heteroatom. The heteroatom is preferably selected from N, O or S.

[0137] The terms "heteroaromatic ring system" and "aromatic ring system" as defined in this application are distinguished from each other by the fact that an aromatic ring system cannot contain any heteroatoms as ring atoms, whereas a heteroaromatic ring system must contain at least one heteroatom as a ring atom. Such heteroatoms may be present as ring atoms of a non-aromatic heterocycle in the system as well as as ring atoms of an aromatic heterocycle in the system.

[0138] In accordance with the above, any aryl group as defined above is encompassed within the term "aromatic ring system" as defined above, and any heteroaryl group as defined above is encompassed within the term "heteroaromatic ring system" as defined above.

[0139] The aromatic ring system having 6 to 40 aromatic ring atoms or the heteroaromatic ring system having 5 to 40 aromatic ring atoms is, in particular, a radical derived from the aforementioned aryl or heteroaryl groups or from biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, trimerized indene, isotrimerized indene, spirotrimerized indene, spiroisotrimerized indene and indenocarbazole, or any combination of these radicals.

[0140] For the purposes of the present invention, a straight-chain alkyl radical having 1 to 20 C atoms or a branched or cyclic alkyl radical having 3 to 20 C atoms or an alkenyl or alkynyl radical having 2 to 20 C atoms, wherein individual H atoms or CH2 groups may also be substituted by the radicals mentioned above under the definitions of radicals, is preferably taken to mean a radical such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl.

[0141] Alkoxy or thioalkyl radicals having 1 to 20 C atoms are preferably taken to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec- butylthio, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.

[0142] The expression "two or more groups may be linked to each other to form a ring" should be understood to include the case where the two groups are linked by a chemical bond. Furthermore, the expression should also be understood to include the case where one of the two groups is H, the H group is removed, and the other of the two groups forms a ring by linking to the position to which the H group was originally linked.

[0143] The following group drawing

[0144]

[0145] It is understood to refer to the group R bonded to the benzene ring 1 The number of labels (here five), where the group R 1 Can be the same or different in each occurrence, as follows:

[0146]

[0147] This representation is also used elsewhere in this application and should in each case be interpreted in a manner similar to that described above.

[0148] The HOMO of compound C2 is preferably less than -5.2 eV, preferably less than -5.3 eV, as determined in part E) of the working examples below.

[0149] Compound C2 is preferably a compound which does not transport holes in layer A of the stack of electronic device layers. Addition of greater amounts of compound C2 therefore reduces the hole conductivity of layer A.

[0150] Compound C2 is preferably selected from triazine derivatives, pyrimidine derivatives, pyridine derivatives, quinoxaline derivatives, phosphine oxide derivatives, imidazole derivatives, oxazole derivatives, terphenylidene derivatives, phenanthrol derivatives, phenanthroline derivatives, fluorene derivatives, spirobifluorene derivatives, xanthene derivatives, anthracene derivatives, naphthalene derivatives, dibenzofuran derivatives, indolocarbazole derivatives, indenocarbazole derivatives and carbazole derivatives.

[0151] Preferred compounds C2 are selected from the following compounds:

[0152]

[0153]

[0154]

[0155]

[0156] where R 1 、R 2 and R 3 As defined above, and preferably corresponding to its preferred embodiments, and wherein

[0157] Ar 4 Selected from: having 6 to 50 aromatic ring atoms and being surrounded by a group R 1 substituted aromatic ring system; and having 5 to 50 aromatic ring atoms and substituted by a group R 1 Substituted heteroaromatic ring systems.

[0158] Particularly preferred among the above formulae are formulae (2-1) to (2-3) and (2-8).

[0159] According to a preferred embodiment of the present invention, compound C2 corresponds to a formula selected from the following formulae:

[0160]

[0161] where R 1 、R 2 and R 3 As defined above, preferably corresponding to the above preferred embodiment, and Ar 5 selected from the group consisting of a group having 6 to 20 aromatic ring atoms and being surrounded by a group R 1 Substituted aromatic ring systems and aromatic ring systems having 5 to 20 aromatic ring atoms and being replaced by a group R 1 Substituted heteroaromatic ring system, and the symbol m is 0 or 1, wherein m=0 refers to the group Ar 5 does not exist and is related to (Ar 5 ) m The two groups that are bonded are directly bonded to each other.

[0162] In structures (1-21) to (1-27), two bonds are drawn into the middle ring, wherein the specific attachment positions of the two bonds to the middle ring are not specified. This is understood to mean that an indenocarbazole group and an indolocarbazole group are formed, respectively, as either positional isomer. Therefore, the two bonds can be attached at any position on the middle ring, preferably at adjacent positions on the middle ring.

[0163] Preferably, compound C2 does not contain any carbazole groups. Furthermore, preferably, compound C2 does not contain any triarylamine groups, more preferably does not contain amino groups.

[0164] Preferred specific compounds that can be used as compound C2 according to the present application are shown in the table below:

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] The molar mass of compound C2 is preferably 400 g / mol or higher, more preferably 500 g / mol to 1200 g / mol. In addition, preferably, the glass transition temperature T of compound C2 is g >100℃. Glass transition temperature (T g ) is determined using a technique called differential scanning calorimetry (DSC), which is well established and well known in the art. The glass transition is characterized by a step in the heat flow-temperature curve. The temperature at which this transition occurs is the glass transition temperature (T g ).

[0188] Compound C3 is a p-type dopant. Its function is to p-type-dopant layer A. A p-type dopant is preferably understood to be an organic compound that acts as an electron acceptor compound and is capable of oxidizing one or more other compounds present in the layer mixture together with it, in particular compound C1 in layer A of the device according to the present invention. The LUMO energy level of a p-type dopant such as compound C3 is preferably no more than 1.0 eV higher than that of the other components of the layer, in particular compound C1, and preferably no more than 0.5 eV higher. More preferably, the LUMO energy level of a p-type dopant such as C3 is lower than the HOMO energy level of the other components of the layer, in particular compound C1. The LUMO values of the compounds according to the present application are determined by quantum chemical calculations, as described in section E) of the Examples of the present application. The terms "higher" and "lower" with respect to LUMO values are to be understood in the same manner as described above with respect to HOMO values.

[0189] The p-type dopant, such as compound C3, is preferably distributed substantially uniformly throughout the layer. This can be achieved, for example, by co-evaporating the p-type dopant with the other compounds present in the layer, which is preferred. Alternatively, it can be achieved by applying a solution containing the p-type dopant and the other components of layer A to form layer A. Preferably, the p-type dopant, in particular compound C3, is present in the p-doped layer in a proportion of 1% to 10%, preferably 3% to 8%. When the compound is applied in vapor form, the proportion is by volume; and when the compound is applied in solution, the proportion is by weight. Preferably, the compound is applied in vapor form, and the proportion is by volume.

[0190] Compound C3 is preferably a metal organic electron acceptor compound or an organic electron acceptor compound. Preferably, they are organic electron acceptor compounds. Compound C3 is preferably selected from: aromatic or heteroaromatic condensed rings, especially condensed rings substituted with electron-withdrawing groups; quinone dimethane, especially p-quinone dimethane, especially dicyanoquinone dimethane; conjugated diketones, especially conjugated cyclic diketones; indenylfluorenedione; azaindenylfluorenedione; azapine, especially heptaazapine; azatriphenylene, especially hexaazatriphenylene; azines, preferably triazines, pyrimidines and pyridines; boron compounds, especially borate esters or triarylboron derivatives; trimethylcyclopropane, especially hexacyanotrimethylcyclopropane; I2; metal halides, preferably transition metals. Metal halides; metal oxides, preferably metal oxides comprising at least one transition metal or a metal from main group 3, more preferably transition metal oxides, more preferably oxides of rhenium, molybdenum and tungsten, still more preferably Re2O7, MoO3, WO3 and ReO3; transition metal complexes, preferably complexes of Cu, Co, Fe, Ni, Pd and Pt, preferably complexes having a ligand containing at least one oxygen atom as a binding site, for example preferably a CO ligand or a ligand containing at least one carboxyl group or a cyclopentadienyl ligand; and main group metal complexes.

[0191] Preferred compounds C3 are the compounds listed below:

[0192] 1) Complexes of main group metals and transition metals, in particular as disclosed in WO 2021 / 151959, DE 102018118278 A1, WO 2021 / 048044 A1, US 9166178 B2, DE 102012209523 A1, US 2018 / 108849 A1 and WO 2009 / 106068 A1. "Cp" hereinafter represents a cyclopentadienyl group.

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] 2) Azines, cyclic diones, quinodimethanes, dicyanoquinodimethanes and boron compounds, in particular as described in US2021 / 050527, WO2022 / 010068, US2017 / 040536, US2003 / 008174, CN110483529, WO2012 / 031735, KR2017-0114778, US2020 / 235 304. KR102230986, US2021 / 202858, US2022 / 123217, US2022 / 238814, US2022 / 23123 1. US2020 / 144552, US2018 / 331297, US2018 / 086775, US2018 / 309057, US2020 / 12720 7. US8481177, US2014 / 001461, US2021 / 119162, US2019 / 058128, WO2009 / 003455, U S2019 / 088896, KR2018-0051356, CN110383518, US2009 / 152535, CN110383518, WO20 10 / 097433, US2021 / 280795, US2022 / 020935, DE102020104604, US2020 / 087311, CN115207254, US2019 / 131548, US2020 / 091430, US2005-139810, and US2003 / 006411:

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] In layer A, which is preferably layer A1, the ratio of compound C1 to compound C2 is preferably between 99:1 and 1:99, more preferably between 90:10 and 10:90, most preferably between 80:20 and 20:80, and most preferably between 35:65 and 65:35. If the compounds are applied in the form of a vapor using different evaporation sources, the ratios are by volume in % by volume. If the compounds are applied in the form of a solution or if they are applied in the form of a solution, the ratios are by weight in % by weight. Preferably, the compounds are applied in the form of a premix as a vapor, and the ratios are by volume.

[0224] Preferably, compound C2 is present in a proportion of at least 30%, preferably at least 40%, most preferably at least 50% in layer A, preferably layer A1. The proportions are determined as above.

[0225] In this embodiment, layer A is layer A1, which is a hole injection layer and is adjacent to the anode. In this case, it is also preferred that a hole transport layer adjacent to layer A1 is provided on the cathode side of layer A1, and an electron blocking layer is provided between the hole transport layer and the light-emitting layer, the electron blocking layer being adjacent to the light-emitting layer on the anode side of the light-emitting layer. Other layers can be present between the hole transport layer and the electron blocking layer. Preferably, there is no layer between the hole transport layer and the electron blocking layer, so that they are adjacent to each other. In addition, preferably, a hole blocking layer adjacent to the light-emitting layer is provided on the cathode side of the light-emitting layer. In addition, preferably, an electron transport layer is provided on the cathode side of the hole blocking layer. In addition, preferably, an electron injection layer adjacent to the electron transport layer is provided on the cathode side of the electron transport layer, and the electron injection layer is preferably adjacent to the cathode. Other layers can optionally be present between the hole blocking layer and the electron transport layer. Preferably, the hole blocking layer and the electron transport layer are adjacent to each other.

[0226] The order of the layers in the stack of layers of the electronic device is preferably as follows, from anode to cathode in the following order:

[0227] -anode

[0228] - Layer A, serving as a hole injection layer

[0229] -Hole transport layer

[0230] -Optionally one or more further hole transport layers

[0231] -Electron blocking layer

[0232] -Luminescent layer

[0233] -Hole blocking layer

[0234] -Electron transport layer

[0235] -Optionally one or more additional electron transport layers

[0236] -Electron injection layer

[0237] -cathode.

[0238] Preferably, after application of the anode, a pixel defining layer (PDL) is applied in an electronic device comprising a stack of multiple layers, preferably by lithographic methods.

[0239] Further layers may be present in the stack, selected from the known layers for OLEDs, i.e. hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, interlayers, charge generation layers, output coupling layers, light-emitting layers, pixel defining layers and / or organic or inorganic p / n junctions.

[0240] This layer sequence is particularly preferred for the layer stack that is a stack of blue phosphor layers and for the layer stack that has the highest switching voltage.

[0241] The layer order of the stack of layers of the electronic device can be the same or different, preferably different, between different layer stacks.Preferably, layers described as common layers are present in all layer stacks.

[0242] According to a preferred embodiment, the stack of layers of the electronic device comprises, between layer A1 and the light-emitting layer, two further layers each, which are adjacent to one another and are arranged in the order from closest to the anode to furthest from the anode:

[0243] ■ a hole transport layer; and

[0244] ■Electron blocking layer.

[0245] According to one preferred embodiment, the hole transport layer comprises compound C1, more preferably consists of compound C1. Preferably, compound C1 of layer A1 is the same compound as that of the hole transport layer. In this case, compound C1 present in the hole transport layer preferably has a high hole mobility. According to other preferred embodiments, the hole transport layer comprises only a single compound. According to other preferred embodiments, the hole transport layer is not p-doped. Furthermore, the hole transport layer is preferably shared by the stack of two layers.

[0246] It is understood that the hole transport layer itself can have a high or low transverse current. Generally, it is preferred that the hole transport layer has a low transverse current. Regardless of whether the hole transport layer itself has a high or low transverse current, the technical effects of the present invention can be achieved. However, if the hole transport layer has a low transverse current, the absolute value of the transverse current exhibited by the device will generally be lower. Therefore, if obtaining the lowest possible transverse current is a priority in device design, it is generally preferred to select a hole transport layer material with a low transverse current.

[0247] For the anode of the stack of electronic device layers, materials with a high work function are preferred. Preferably, the anode has a work function greater than 4.5 eV relative to vacuum. Firstly, metals with a high redox potential such as Ag, Pt or Au are suitable for this purpose. Secondly, metal / metal oxide electrodes (e.g. Al / Ni / NiO x 、Al / PtO x) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable light emission. Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductively doped organic materials, in particular conductively doped polymers. Furthermore, the anode may also consist of two or more layers, for example an inner layer of ITO and an outer layer of a metal oxide, the metal oxide being preferably tungsten oxide, molybdenum oxide or vanadium oxide.

[0248] The preferred cathode of the stack of layers of the electronic device is a metal with a low work function, a metal alloy or a multilayer structure consisting of a variety of metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). In addition, an alloy consisting of an alkali metal or alkaline earth metal and silver is suitable, for example, an alloy consisting of magnesium and silver. In the case of a multilayer structure, in addition to the metals, other metals such as Ag or Al with a relatively high work function can also be used, in which case combinations of the metals such as Ca / Ag, Mg / Ag or Ba / Ag are generally used. It is also preferred that a thin intermediate layer of a material with a high dielectric constant be introduced between the metal cathode and the organic semiconductor. Examples that can be used for this purpose are alkali metal fluorides or alkaline earth metal fluorides, as well as corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). In addition, lithium quinolate (LiQ) can also be used for this purpose. The layer thickness of this layer is preferably from 0.5 nm to 5 nm.

[0249] The light-emitting layer of the stack of layers of the electronic device may be a phosphorescent light-emitting layer or a fluorescent light-emitting layer. The phosphorescent light-emitting layer preferably contains at least one host material, more preferably two host materials, and at least one phosphorescent light-emitting body. The fluorescent light-emitting layer preferably contains at least one host material and at least one fluorescent light-emitting body.

[0250] In a preferred embodiment of the present invention, the emitting layer of the stack of layers of the electronic device is selected from a blue fluorescent emitting layer, a green phosphorescent emitting layer and a red phosphorescent emitting layer. Accordingly, the emitting layer of the electronic device contains a blue fluorescent emitting compound in the first case, a green phosphorescent emitting compound in the second case and a red phosphorescent emitting compound in the third case. Preferably, the electronic device comprises a set comprising three stacks, wherein the first stack of layers comprises a red phosphorescent emitting layer and is a red emitting stack, wherein the second stack of layers comprises a green phosphorescent emitting layer and is a green emitting stack, and wherein the third stack of layers comprises a blue fluorescent emitting layer and is a blue emitting stack.

[0251] The emitting layer of the electronic device preferably comprises a plurality of matrix materials (mixed matrix system). According to a preferred embodiment, the emitting layer of the electronic device may comprise a plurality of emitting compounds. In the case of a phosphorescent emitting layer, it is preferred that the layer contains two or more, preferably exactly two, different matrix materials.

[0252] Mixed matrix system preferably comprises two or three different host materials, more preferably two different host materials.Preferably, in this case, one of the two materials is a material with hole transport properties, and the other material is a material with electron transport properties.Also preferably, one of the materials is selected from a compound (wide bandgap material) with a large energy difference between HOMO and LUMO.Two different host materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1, most preferably 1:4 to 1:1.However, the performance of the desired electron transport and hole transport of the mixed matrix component can also be mainly or completely merged in a single mixed matrix component, in which case one or more other mixed matrix components play other functions.

[0253] The following material classes are preferably used in the light-emitting layer of the electronic device:

[0254] Phosphorescent emitters:

[0255] The term "phosphorescent emitter" generally includes compounds in which the emission occurs via spin-forbidden transitions, for example from an excited triplet state or a state with a higher spin quantum number, such as a quintet state.

[0256] Suitable phosphorescent emitters are, in particular, compounds which emit light upon appropriate excitation, preferably in the visible region, and furthermore comprise at least one atom having an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80. As phosphorescent emitters, preference is given to using compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium, platinum or copper.

[0257] In the context of the present invention, all luminescent iridium, platinum or copper complexes are regarded as phosphorescent compounds.

[0258] In general, all phosphorescent complexes known to those skilled in the art for phosphorescent OLEDs according to the prior art and in the field of organic electroluminescent devices are suitable for use in the devices according to the present application. Particularly preferred phosphorescent emitters are explicitly depicted in the following table:

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] Fluorescent light source:

[0266] Preferred fluorescent luminescent compounds are selected from the class of arylamines. In the context of the present invention, arylamine or aromatic amine is understood to mean a compound comprising three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms. Preferred examples are aromatic anthraceneamine, aromatic anthracenediamine, aromatic pyreneamine, aromatic pyrenediamine, aromatic leucamine or aromatic leucamine. Aromatic anthraceneamine is understood to mean a compound in which one diarylamino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Aromatic pyreneamine, pyrenediamine, leucamine and leucamine are defined in a similar manner, with the diarylamino groups preferably being bonded to the 1-position or the 1- and 6-positions of the pyrene. Further preferred luminescent compounds are indenofluorenamine or indenofluorenediamine, benzoindenofluorenamine or benzoindenofluorenediamine and dibenzoindenofluorenamine or dibenzoindenofluorenediamine and indenofluorene derivatives with fused aryl groups. Also preferred are pyrenarylamines. Also preferred are benzoindenofluorenamine, benzofluorenamine and extended benzoindenofluorene, phenanthene ... Oxazines and fluorene derivatives connected to furan units or thiophene units.

[0267] Matrix material of fluorescent light emitter:

[0268] Preferred matrix materials for fluorescent emitters are selected from the following classes of substances: oligoarylidenes (e.g. 2,2',7,7'-tetraphenylspirobifluorene), in particular oligoarylidenes containing fused aromatic groups; oligoarylidene vinylidene; polypodal metal complexes; hole-conducting compounds; electron-conducting compounds, in particular ketones, phosphine oxides and sulfoxides; atropisomers; boronic acid derivatives; or benzanthracene. Particularly preferred matrix materials are selected from the following classes: oligoarylidenes comprising naphthalene, anthracene, benzanthracene and / or pyrene, or atropisomers of these compounds; oligoarylidene vinylidene; ketones; phosphine oxides; and sulfoxides. Very particularly preferred matrix materials are selected from the following classes: oligoarylidenes comprising anthracene, benzanthracene, triphenylene and / or pyrene, or atropisomers of these compounds. In the context of the present invention, an oligoarylidene is to be understood as meaning a compound in which at least three aryl or arylidene groups are bonded to one another.

[0269] Matrix materials for phosphorescent emitters:

[0270] Preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones; triarylamines; carbazole derivatives such as CBP (N,N-dicarbazolylbiphenyl); indolocarbazole derivatives; indenocarbazole derivatives; azacarbazole derivatives; bipolar matrix materials; silanes; borazolidines or boric esters; triazine derivatives; zinc complexes; siladiazacyclopentazone or silatetraazacyclopentazone derivatives; phosphodiazacyclopentazone derivatives; bridged carbazole derivatives; terphenylidene derivatives; or lactams.

[0271] In addition to the layers mentioned above, the stack of layers of the electronic device may also contain further layers. These layers are, for example, selected in each case from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, interlayers, charge generation layers, coupling-out layers, light-emitting layers and / or organic or inorganic p / n junctions. However, it should be noted that not all of these layers must be present, and the choice of layers always depends on the compounds used, in particular on whether the device is a fluorescent or phosphorescent electroluminescent device.

[0272] In a preferred embodiment, the electron transport layer of the stack of layers comprises a triazine derivative and lithium quinolate. In a preferred embodiment, the electron injection layer comprises a triazine derivative and lithium quinolate. In a particularly preferred embodiment, the electron transport layer and / or the electron injection layer, most preferably the electron transport layer and the electron injection layer, comprise a triazine derivative and lithium quinolate (LiQ).

[0273] The hole-blocking layer preferably has hole-blocking and electron-transporting properties and directly adjoins the light-emitting layer on the cathode side.

[0274] Suitable electron-transport materials are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, Vol. 107 (No. 4), pp. 953-1010 or other materials used in these layers according to the prior art.

[0275] The materials used for the electron transport layer, the electron injection layer and the hole blocking layer can be any materials used as electron transport materials in the electron transport layer according to the prior art. Particularly suitable are aluminum complexes such as Alq3, zirconium complexes such as Zrq4, lithium complexes such as Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, Oxadiazole derivatives, aromatic ketones, lactams, boranes, phosphodiazoline derivatives and phosphine oxide derivatives. Particularly preferred materials for the electron transport layer, electron injection layer and hole blocking layer are the materials explicitly listed in the table on pages 73-75 of WO2020 / 109434A1.

[0276] The electronic device can be used as a display device or as a part of a display device, as a light source in lighting applications and as a light source in medical and / or cosmetic applications.

[0277] A detailed description of an electronic device comprising a stack of two or more layers in close proximity to each other layers, at least one of which is a series stack

[0278] In this electronic device design, there is preferably a stack of multiple layers, the stack of each layer is in close proximity to the stack of its adjacent layer, wherein the layers of the stack are preferably parallel to each other. Preferably, the composition of the stack of these layers is the same. According to a preferred embodiment, the stack of these layers all have the same luminescent color, preferably white or blue. According to an alternative preferred embodiment, the stack of the layers has different luminescent colors, for example, in a stack of triple series layers, the stack of the first layer has a blue luminescent color, the stack of the second layer has a green luminescent color, and the stack of the third layer has a red luminescent color. Therefore, as described in the above section, an electronic device comprising side-by-side stacks of different luminescent colors can also comprise stacks of series layers, for example in an RGB side-by-side arrangement. Thus, the embodiments described in the above section and the embodiments described in this section can be combined in one embodiment.

[0279] The stacking of layers in this design of electronic devices is preferably a tandem stacking. The basic structure of a tandem stacking is as follows Figure 2A As shown, as described in detail above.

[0280] In the electronic component design according to the present application, layer A is preferably present as layer A1 or layer A2 , or as both layer A1 and layer A2 . Figure 2B The case where layer A is shown is layer A1 , which is a hole injection layer, as described in detail above. Figure 2C Layer A is shown as layer A2, which is a sublayer or charge generation layer of a series stack of charge generation layers, as described in detail above. Figure 2D The case is shown where layer A acts simultaneously as layer A1 which is a hole injection layer and layer A2 which is a charge generation layer or a sublayer of a charge generation layer, as described in detail above.

[0281] In the case where layer A is present as layer A1 in the electronic device, the same preferred embodiments of the layers and their components apply as detailed above for the case of the electronic device with a multi-color side-by-side design.

[0282] In the case of layer A2, this layer is preferably present in each case between two emitting layers of the layer stack. Preferably, when there are two emitting layers, there is therefore one layer A2 between these emitting layers. Preferably, when there are three emitting layers, there are therefore two layers A2 in the electronic device, namely a first layer A2 located between the first of the three emitting layers and the second of the three emitting layers, and a second layer A2 located between the second of the three emitting layers and the third of the three emitting layers. Preferably, when there are four emitting layers, there are therefore three layers A2 in the electronic device, namely a first layer A2 located between the first of the four emitting layers and the second of the four emitting layers, a second layer A2 located between the second of the four emitting layers and the third of the four emitting layers, and a third layer A2 located between the third of the four emitting layers and the fourth of the four emitting layers.

[0283] Where there are three emitting layers in the layer stack, preferably the first of these comprises a blue emitting layer, the second comprises a green emitting layer, and the third comprises an orange or red, preferably red, emitting layer.

[0284] In this electronic device design, the preferred layer order of the stack of layers is from anode to cathode in the following order:

[0285] ○Anode

[0286] ○First hole injection layer, preferably layer A

[0287] ○First hole transport layer

[0288] ○First electron blocking layer

[0289] ○First light-emitting layer

[0290] ○First hole blocking layer

[0291] ○First electron transport layer

[0292] ○First charge generation layer, preferably layer A

[0293] ○Second hole transport layer

[0294] ○Second electron blocking layer

[0295] ○Second light-emitting layer

[0296] ○Second hole blocking layer

[0297] ○Second electron transport layer

[0298] ○ Second charge generation layer, preferably layer A

[0299] ○Third hole transport layer

[0300] ○Third electron blocking layer

[0301] ○Third light-emitting layer

[0302] ○Third hole blocking layer

[0303] ○Third electron transport layer

[0304] ○Third electron injection layer

[0305] ○Cathode.

[0306] Preferably, after application of the anode, a pixel defining layer (PDL) is applied in an electronic device comprising a stack of multiple layers, preferably by lithographic methods.

[0307] Further layers may be present in the stack, selected from the known layers listed above for OLEDs.

[0308] The charge generating layers are preferably selected from layer A. If they are not selected from layer A, they are preferably constructed as described in N. Amaroli, HJ Bolink (eds.), Photoluminescent Materials and Electroluminescent Devices, Topics in Current Chemistry Collections, Springer, 2017, pp. 360-362, section 3.2.

[0309] According to a preferred embodiment, the charge generation layer is composed of two sublayers, wherein the first of these sublayers is layer A, and the second of these sublayers is a layer comprising an electron transport material and an n-type dopant. The total thickness of these two sublayers is preferably 10 nm to 40 nm.

[0310] Layer A2 is preferably a charge generation layer or a sublayer of a charge generation layer, as described above.

[0311] Regarding the composition of layer A2, the same preferred embodiments as described above for layer A1 apply. Preferably, the proportion of compound C3 in layer A2 is 5% to 20%. The percentages are preferably by volume.

[0312] The stack of layers, with the exception of layer A, is preferably constructed as known in the art. In particular, it is preferred that the functional layers have the preferred compositions as detailed above for the multi-color side-by-side electronic device.

[0313] An electronic device according to this device design is preferably used as a display device or as part of a display device, as a light source in lighting applications and as a light source in medical and / or cosmetic applications.

[0314] Detailed description of the method for producing an electronic device, in particular the method for applying layer A

[0315] In a preferred embodiment, the electronic device is characterized in that one or more layers are applied by a sublimation method. In this case, the material is sublimated in a vacuum system at a temperature of less than 10 -5 mbar, preferably less than 10 -6 mbar by vapor deposition. However, in this case, it is also feasible that the initial pressure is much lower, for example less than 10 - 7 Preferably, layer A of the electronic component is applied by vapor deposition.

[0316] Another aspect of the present application is a method for producing an electronic device as defined above, characterized in that compounds C1 and C2 are first mixed and the resulting mixture is then used to produce layer A by vapor deposition. In this case, preferably, the mixture of compounds C1 and C2 is used as one source for the vapor deposition process, and compound C3 is applied from a different source.

[0317] In one embodiment of the present invention, the mixture of compound C1 and compound C2 does not contain any other components, i.e., functional materials, besides compound C1 and compound C2. This means that the mixture consists of compound C1 and compound C2. These mixtures are also referred to as premixes or premix systems and can be used as one material for vapor deposition of layer A, wherein the second material is compound C3. Preferably, these mixtures maintain their mixing ratio throughout the vapor deposition process, such that the ratio of the two compounds C1 and C2 in layer A is the same or similar to the ratio of the compounds in the premix. In this way, a mixed layer with compounds C1 and C2 uniformly distributed in a predeterminable ratio can be obtained in a simple and rapid manner without having to start two different material sources during the vapor deposition process, as is the case when compounds C1 and C2 are applied as a mixed layer by co-evaporation.

[0318] Likewise preferred is an electronic component, characterized in that one or more layers are applied using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. -5The material is applied at a pressure of mbar to 1 bar. A special case of this method is the OVJP (Organic Vapor Jet Printing) method, in which the material is applied directly through a nozzle and thus structured (e.g. MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0319] Furthermore, an electronic device is preferred, characterized in that one or more layers are produced from solution, for example by spin coating or by any printing method such as screen printing, flexographic printing, nozzle printing or offset printing, but more preferably by LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. According to a preferred embodiment, layer A is applied from solution, preferably by one of the methods described above. In this case, the components of layer A need to be soluble in the solvent.

[0320] It is also preferred that the electronic device according to the present application is produced by applying one or more layers in the form of a solution and by applying one or more layers by a sublimation method.

[0321] After application of the various layers, the component is structured, contact connections are provided, and finally sealed to exclude the damaging effects of water and air, depending on the intended use.

[0322] Mixture of compounds for preparing layer A

[0323] As described above, a mixture comprising at least one compound C1 and at least one compound C2 is preferably used to prepare layer A of the electronic device according to the present application, preferably by vapor deposition. The preferred embodiments regarding the mutual ratio of compounds C1 and C2 and the preferred embodiments regarding the chemical structures and properties of compounds C1 and C2, as detailed above for the electronic device, also apply to this mixture. Furthermore, as described above, this mixture maintains its mixing ratio during the vapor deposition process, such that the ratio of the two compounds C1 and C2 in layer A is the same or similar to the ratio of the compounds in the mixture. Therefore, the use of this mixture for vapor deposition of layer A is also a subject of the present application.

[0324] A mixture comprising at least one compound C1, at least one compound C2, and at least one compound C3 is preferably used to produce layer A of the electronic device according to the present application, preferably by a solution-based process. The preferred embodiments regarding the mutual ratios of compounds C1, C2, and C3 and regarding the chemical structures and properties of compounds C1, C2, and C3, as detailed above for the electronic device, also apply to this mixture. Therefore, the use of this mixture for depositing layer A by a solution-based process is also a subject of the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0325] Figure 1An electronic device according to the present application is shown, the device comprising a stack of two layers, each comprising a single light-emitting layer, wherein the hole injection layer is a shared layer. The reference numerals in the figure are explained as follows:

[0326] 1 Electronic devices

[0327] 2a The first layer of stacking

[0328] 2b Second layer stack

[0329] 3 basal layer

[0330] 4a Anode of the first layer of the stack

[0331] 4b Anode of the second stack

[0332] 5 as a shared layer, preferably as a hole injection layer of layer A

[0333] 6a First layer of the stacked light-emitting layer

[0334] 6b Second layer of the stacked light-emitting layer

[0335] 7 cathode

[0336] Figure 2A A stack of layers as a stack of tandem layers is shown, comprising at least two light-emitting layers and a charge generation layer located between the two light-emitting layers. The reference numerals in the figure are explained as follows:

[0337] 3 base

[0338] 4 anode

[0339] 5Hole injection layer

[0340] 6 luminous layer

[0341] 7 cathode

[0342] 8-layer stack

[0343] 9a First light-emitting unit

[0344] 9b Second light-emitting unit

[0345] 10 Charge generation layer

[0346] 11Hole transport layer

[0347] 12Electron transport layer

[0348] 13Electron injection layer

[0349] Figure 2BAn electronic device according to the present application is shown, comprising two stacks of tandem layers, each comprising at least two light-emitting layers and a charge generation layer located between the two light-emitting layers, wherein the hole injection layer is a shared layer and the charge generation layer is not a shared layer. The reference numerals in the figure are explained as follows:

[0350] 1 Electronic devices

[0351] 2a The first layer of stacking

[0352] 2b Second layer stack

[0353] 3 base

[0354] 4a Anode of the first layer of the stack

[0355] 4b Anode of the second stack

[0356] 5 Hole injection layer as a shared layer, preferably as layer A

[0357] 6a First layer of the stacked light-emitting layer

[0358] 6b Second layer of the stacked light-emitting layer

[0359] 7 Cathode

[0360] 10a Charge generation layer of the first stack

[0361] 10b Second stacked charge generation layer

[0362] 14a The second light-emitting layer of the first stack

[0363] 14b The second light-emitting layer of the second stack

[0364] Figure 2C An electronic device according to the present application is shown, comprising two stacks of tandem layers, each comprising at least two light-emitting layers and a charge generation layer located between the two light-emitting layers, wherein the hole injection layer is not a shared layer and the charge generation layer is a shared layer. The reference numerals in the figure are explained as follows:

[0365] 1 Electronic devices

[0366] 2a The first layer of stacking

[0367] 2b Second layer stack

[0368] 3 base

[0369] 4a Anode of the first layer of the stack

[0370] 4b Anode of the second stack

[0371] 5a Hole injection layer of the first stack

[0372] 5b Hole injection layer of the second stack

[0373] 6a Light-emitting layer of the first stack

[0374] 6b Second stacked light-emitting layer

[0375] 7 Cathode

[0376] 10 Charge generation layer as a shared layer, preferably as layer A

[0377] 14a The second light-emitting layer of the first stack

[0378] 14b The second light-emitting layer of the second stack

[0379] Figure 2D An electronic device according to the present application is shown, comprising two stacks of tandem layers, each of which comprises at least two light-emitting layers and a charge generation layer located between the two light-emitting layers, wherein the hole injection layer and the charge generation layer are shared layers. The reference numerals in the figure are explained as follows:

[0380] 1 Electronic devices

[0381] 2a The first layer of stacking

[0382] 2b Second layer stack

[0383] 3 base

[0384] 4a Anode of the first layer of the stack

[0385] 4b Anode of the second stack

[0386] 5 Hole injection layer as a shared layer, preferably as layer A

[0387] 6a Light-emitting layer of the first stack

[0388] 6b Second stacked light-emitting layer

[0389] 7 Cathode

[0390] 10 Charge generation layer as a shared layer, preferably as layer A

[0391] 14a The second light-emitting layer of the first stack

[0392] 14b The second light-emitting layer of the second stack

[0393] Figure 3A A device for measuring a lateral current flowing between two stacks in close proximity to each other and through a shared layer A is shown. The reference numerals in the figure are explained as follows:

[0394] 2a The first layer of stacking

[0395] 2b Second layer stack

[0396] 3 base

[0397] 4a Anode of the first layer of the stack

[0398] 4b Anode of the second stack

[0399] 6a Light-emitting layer of the first stack

[0400] 6b Second stacked light-emitting layer

[0401] 7 Cathode

[0402] 12 Electron transport layer as a shared layer

[0403] 15a is a hole injection layer corresponding to layer A as a shared layer

[0404] 15b as a hole transport layer shared by the

[0405] 16 Transverse current measurement device

[0406] 17 Voltage application device

[0407] 18 Current measuring device

[0408] 19 Transverse current flow

[0409] Figure 3B A device for measuring lateral current is shown. Figure 3A The same as shown in , but different in that the light emitting layer is a shared layer and not two separate layers, reference numeral 6.

[0410] The reference numerals in the figure are explained as follows:

[0411] 2a The first layer of stacking

[0412] 2b Second layer stack

[0413] 3 base

[0414] 4a Anode of the first layer of the stack

[0415] 4b Anode of the second stack

[0416] 6 Emissive layer as a shared layer

[0417] 7 Cathode

[0418] 12 Electron transport layer as a shared layer

[0419] 15a is a hole injection layer corresponding to layer A as a shared layer

[0420] 15b as a hole transport layer shared by the

[0421] 16 Transverse current measurement device

[0422] 17 Voltage application device

[0423] 18 Current measuring device

[0424] 19 Transverse current flow Example

[0425] A) Reduction of lateral current by adding a low HOMO compound to the hole transport compound in the hole injection layer

[0426] The example shown is based on an existing OLED stack consisting of seven organic layers between an ITO anode and an aluminum cathode. The composition of the layers is shown in Table 1.

[0427] The examples demonstrate the effect of a hole injection layer composed of three materials (a hole transport compound, a low HOMO compound, and a p-type dopant) on the lateral current and are compared with a reference HIL composed only of a hole transport compound and a p-type dopant. The HIL of the OLED uses a combination of four different HTMs (HTM-1, HTM-2, HTM-3, and HTM-4) and three different low HOMO compounds (ETM-2, ETM-3, and ETM-4). In all cases, the p-type dopant is PDM-1. The HTM contained in the HTL can be the same as or different from the HTM contained in the HIL. In the examples of Table 2, it is the same. Table 2 shows the composition, mixing ratio, and thickness of the HIL and HTL layers of the electronic device. The mixing ratio of the compounds in the mixed layer is given in %, for example in Example 1-1 below: HTM-1:PDM-1:ETM-2 (45%:5%:50%). The chemical structures of the compounds used are shown in the table below. HTM-4 is fluorene having an amine group at the 2-position and a substituent on one aromatic ring of the fluorene.

[0428] The stacks were prepared on two types of substrates: one substrate was used for electro-optical measurements of OLED device performance, and another substrate was specifically designed for lateral current measurements.

[0429]

[0430]

[0431]

[0432]

[0433] The lateral currents of the OLED according to the invention and the reference OLED described above were measured.

[0434] The method for measuring the lateral current is described in Matthias Diethelm et al., Quantitative analysis of pixel crosstalk in AMOLED displays, Journal of Information Display, Vol. 19, pp. 61-69, 2018, Section 2.1 and Figure 1 (d) is described. The structure of the device under test is as follows Figure 3A or Figure 3B As shown in Figure 3B In.

[0435] Figure 3A and 3B A device 16 for measuring a transverse current, which occurs between two stacks placed in close proximity and flows through a shared layer A, is shown. The device comprises a two-layer stack 2a and 2b, both applied to a common substrate 3. The second stack is the operating stack, to which a voltage is applied via a device 17. The first stack is the measuring stack, to which a transverse current 19 is measured via a device 18. The two-layer stacks 2a and 2b each comprise a separate anode 4a and 4b, Figure 3A In the case of separated light emitting layers 6a and 6b and Figure 3B When a voltage is applied to the second stack 2b using device 17, the lateral current 19 flowing through the shared layer 15a, preferably layer A, can be measured using device 18.

[0436] There are two pixels on the OLED device used to measure the lateral current, each pixel having an array of interdigitated ITO electrodes covered by an organic pixel defining layer (PDL). In the PDL, the ITO electrodes have precise openings so that the gap width between the two electrodes is 20μm. On top of this structure, the OLED stack is evaporated as a common layer covering the array of interdigitated electrodes. A voltage source is connected to the common cathode and one of the electrodes and to ground. The other electrode is connected via an ammeter to ground. The ammeter measures the lateral current collected by the interdigitated electrodes. In Table 4, the measured lateral current values are listed. The measurements are performed at a voltage of 4V.

[0437]

[0438]

[0439] The results show that mixing a low-HOMO compound with the HTM in the HIL can effectively and strongly reduce the lateral current, while keeping other OLED device parameters essentially unchanged, as shown below.

[0440] Surprisingly, if any of the three low-HOMO compounds used is mixed into HTM-1 or HTM-2, in addition to the improved performance, it even leads to a significant increase in lifetime.

[0441] In addition, the general performance data of OLEDs were studied: lifespan, efficiency and voltage. Table 3 below shows the performance data of the above OLEDs in terms of lifespan, efficiency and operating voltage.

[0442] The OLED devices were characterized as follows: the electroluminescence spectrum, operating voltage, lifetime and external quantum efficiency (EQE, given in percentage) were determined. In Table 3, the luminous density of 1000 cd / m 2 The life span (LT) is measured at 30mA / cm 2 The reaction was carried out at a constant current density until the luminous density dropped to 95% of the initial value.

[0443]

[0444]

[0445] The results show that very similar performance parameters are achieved for the OLED according to the invention and the reference OLED in terms of lifetime, efficiency and voltage, while a clear improvement of the lateral current is shown for the OLED according to the invention.

[0446] B) Comparison of the effect of increasing the proportion of low HOMO material and the effect of decreasing the proportion of p-type dopant

[0447] B-1) Changes in p-type dopant and ratio of p-type dopant

[0448] In the examples in this section, the dopant itself and the dopant concentration in the HIL were varied for the hole-transport material HTM-1. Tables 5 to 7 summarize the results. Clearly, regardless of the p-type dopant used, the lateral current decreases with decreasing dopant ratio, while the operating voltage (U) increases nonlinearly with decreasing dopant ratio. The lifetime remains comparable across all experiments. Similar results are observed when ETM-1 is omitted and only HTM-1 and one of PDM-1 to PDM-3 are present in the HIL.

[0449]

[0450]

[0451]

[0452]

[0453] B-2) Changes in the proportion of low HOMO materials

[0454] In the examples in this section, the proportion of low-HOMO material was increased while the proportion of p-type dopant remained constant. The results show that while the lateral current decreases with increasing low-HOMO material proportion, the operating voltage (U) increases with increasing low-HOMO material proportion, albeit with minimal or no increase. The lifetime remained comparable across all experiments.

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461] The results show that increasing the proportion of low-HOMO material in the HIL reduces the lateral current while increasing the operating voltage only slightly or not at all. Therefore, low-HOMO materials can achieve both low operating voltage and low lateral current. This cannot be achieved by varying the proportion of p-type dopants in the HIL, as shown in the previous examples.

[0462] C) Testing devices where the HTM contained in the HTL is different from the HTM contained in the HIL

[0463] C1) Changes in HTM materials in HIL and HTL

[0464] In the examples presented in this section, various existing HTM materials, mixed with low-HOMO materials at varying concentrations, were combined in the HIL layer with an HTM in the HTL layer that differed from the HTM in the HIL. The chemical structures of the compounds used are shown in the table below. HTM-5 is a fluorene with an amine group at the 2-position and a substituent on one of the aromatic rings of the fluorene.

[0465]

[0466]

[0467]

[0468]

[0469] C2) Comparison of the same and different HTM materials in HIL and HTL

[0470] The following examples show a direct comparison of an HTM material mixed with a low HOMO material in the HIL and an HTM in an HTL layer that is either different from or the same as the HTM in the HIL.

[0471]

[0472]

[0473]

[0474] The above data show that if the compound C1 of the HIL and the compound of the adjacent HTL are combined in a suitable manner, a further positive influence on the lateral current density can be achieved.

[0475] D) Other Examples of the Effects Obtained by Increasing the Ratio of Low HOMO Material (Compound C2)

[0476] Similar to the examples in Section B-2, this section increases the type and proportion of low-HOMO material, while maintaining the p-type dopant ratio. The results show that the lateral current decreases with increasing the proportion of low-HOMO material, while the operating voltage (U) increases slightly. Efficiency remains at a comparable level across all experiments.

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483] E) Determination of HOMO value of the compound

[0484] Preferably, according to the application, HOMO energy is determined by quantum chemical calculation. For this reason, software package " Gaussian16 (Rev.B.01) " (Gaussian Inc.) is used. Neutral singlet ground state is optimized on the B3LYP / 6-31G (d) level. For the ground state energy optimized by B3LYP / 6-31G (d), HOMO value is determined on the B3LYP / 6-31G (d) level. TD-DFT singlet and triplet excitation (vertical excitation) are then calculated by identical method (B3LYP / 6-31G (d)) and optimized ground state geometry. Standard settings using SCF and gradient convergence are used.

[0485] From the energy calculation, the HOMO is obtained as the last orbital occupied by two electrons (Alpha occ.eigenvalues) in Hartrees, where HEh represents the HOMO energy in Hartrees. This is used to determine the HOMO value in electron volts as follows:

[0486] HOMO (eV) = (HEh × 27.212).

[0487] Alternatively, the HOMO value in electron volts can be obtained by quantum chemical calculation as described above and then calibrated by cyclic voltammetry measurement as follows:

[0488] HOMO(eV)=(HEh×27.212)×0.8308-1.118.

[0489] The HOMO values of the compounds used in the hole injection layer of this embodiment are as follows:

[0490]

[0491]

[0492] The LUMO energy level can be obtained in a similar manner as described above with respect to the HOMO energy level.

[0493]

[0494]

[0495]

[0496]

Claims

1. An electronic device comprising a stack of a first layer and a stack of a second layer in close proximity to the stack of the first layer, the first stack and the second stack each comprising an anode, a cathode, and a layer A located between the anode and the cathode, and a light-emitting layer, wherein the layer A is shared by the two stacks, and wherein the layer A comprises: ■ at least one compound C1 having hole-transporting properties; ■ at least one compound C2 having a HOMO of less than −5.1 eV; and ■ At least one compound C3, said compound C3 being a p-type dopant.

2. The electronic device according to claim 1, wherein The distance between the stack of the first layer and the stack of the second layer is 5 μm to 40 μm, where the distance is measured from the anode side of the first stack closest to the second stack to the anode side of the second stack closest to the first stack.

3. The electronic device according to claim 1 or claim 2, characterized in that: At least one of the stacks of first and second layers of the electronic device is a tandem stack.

4. Electronic device according to one or more of claims 1 to 3, characterized in that The stack of first layers and the stack of second layers each represent a pixel of the electronic device, and the electronic device is a display.

5. Electronic device according to one or more of claims 1 to 4, characterized in that Layer A is selected from the group consisting of a hole injection layer and a charge generation layer.

6. Electronic device according to one or more of claims 1 to 5, characterized in that Layer A is a hole injection layer directly adjacent to the anode, and the thickness of the hole injection layer is 5 nm to 20 nm.

7. Electronic device according to one or more of claims 1 to 6, characterized in that Compounds C1, C2 and C3 each have a molecular weight of less than 2000 g / mol.

8. Electronic device according to one or more of claims 1 to 7, characterized in that Compound C1 is selected from monotriarylamine, bistriarylamine and carbazoleamine.

9. Electronic device according to one or more of claims 1 to 8, characterized in that Compound C1 conforms to a formula selected from the following: The variable groups and tags are defined as follows: Ar 1 are selected, identically or differently on each occurrence, from: an aromatic ring system having 6 to 50 aromatic ring atoms, said aromatic ring system being surrounded by a group R 1 and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, the heteroaromatic ring system being substituted by a group R 1 replace; R 1 are selected, identically or differently at each occurrence, from the group consisting of: H, D, F, C(=O)R 2 、CN、Si(R 2 )3、N(R 2 )2、P(=O)(R 2 )2、OR 2 、S(=O)R 2 、S(=O)2R 2 , with 1 to 20 C atoms, straight-chain alkyl or alkoxy groups, branched or cyclic alkyl or alkoxy groups, alkenyl or alkynyl groups, aromatic ring systems, aromatic ring systems, and heteroaromatic ring systems, wherein two or more radicals R 1 can be linked to each other to form a ring; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are surrounded by groups R 2 substituted, and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R 2 C=CR 2 -、-C≡C-、Si(R 2 )2. C=O, C=NR 2 、-C(=O)O-、-C(=O)NR 2 -、NR 2 、P(=O)(R 2 ), -O-, -S-, SO or SO2; R 2 are selected, identically or differently at each occurrence, from the group consisting of: H, D, F, C(=O)R 3 、CN、Si(R 3 )3、N(R 3 )2、P(=O)(R 3 )2、OR 3 、S(=O)R 3 、S(=O)2R 3 , with 1 to 20 C atoms, straight-chain alkyl or alkoxy groups, branched or cyclic alkyl or alkoxy groups, alkenyl or alkynyl groups, aromatic ring systems, aromatic ring systems, and heteroaromatic ring systems, wherein two or more radicals R 2 can be linked to each other to form a ring; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are surrounded by groups R 3 substituted, and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R 3 C=CR 3 -、-C≡C-、Si(R 3 )2. C=O, C=NR 3 、-C(=O)O-、-C(=O)NR 3 -、NR 3 、P(=O)(R 3 ), -O-, -S-, SO or SO2; R 3 is selected, identically or differently on each occurrence, from the group consisting of: H, D, F, Cl, Br, I, CN, alkyl radicals having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more radicals R 3 may be connected to each other to form a ring; and wherein the alkyl group, aromatic ring system and heteroaromatic ring system may be substituted by one or more groups selected from F and CN; Ar 3 Selected from: an aromatic ring system having 6 to 13 aromatic ring atoms, said aromatic ring system being surrounded by a group R 1 and a heteroaromatic ring system having 5 to 13 aromatic ring atoms, the heteroaromatic ring system being substituted by a group R 1 replace; X is selected, identically or differently at each occurrence, from a bond, O, S, NR 1 and C(R 1 )2; Y is selected from O and S; n is 0 or 1, wherein when n=0, the group labeled n does not exist, and the groups bonded to the group labeled n are directly connected to each other, provided that in the case of formula (1-1-9), n is not 0.

10. The electronic device according to one or more of claims 1 to 9, characterized in that Compound C2 conforms to a formula selected from the following: where R 1 、R 2 and R 3 each being the same as defined in claim 9, and Ar 4 Selected from: an aromatic ring system having 6 to 50 aromatic ring atoms, said aromatic ring system being surrounded by a group R 1 and a heteroaromatic ring system having 5 to 50 aromatic ring atoms, the heteroaromatic ring system being substituted by a group R 1 replace.

11. Electronic device according to one or more of claims 1 to 10, characterized in that If the layer A is a hole injection layer, the compound C3 is present in the layer A in a proportion of 1% to 10%, and if the layer A is a charge generation layer, the compound C3 is present in the layer A in a proportion of 5% to 20%.

12. Electronic device according to one or more of claims 1 to 11, characterized in that The compound C3 is selected from: an aromatic or heteroaromatic condensed ring, in particular an aromatic or heteroaromatic condensed ring substituted with an electron-withdrawing group; quinone dimethane, in particular p-quinone dimethane, in particular dicyanoquinone dimethane; Conjugated diketones, in particular conjugated cyclic diketones; indenofluorenedione; azaindenofluorenedione; azapine, in particular heptaazapine; azaterphenylidene, in particular hexaazaterphenylidene; azines, preferably triazines, pyrimidines and pyridines; boron compounds, in particular borate esters or triarylboron derivatives; trimethylidenecyclopropane, in particular hexacyanotrimethylidenecyclopropane; I2; metal halides, preferably transition metal halides; metal oxides, preferably containing at least one transition metal or from group 3 Metal oxides of metals containing tungsten, more preferably transition metal oxides, still more preferably oxides of rhenium, molybdenum and tungsten, still more preferably Re2O7, MoO3, WO3 and ReO3; transition metal complexes, preferably complexes of Cu, Co, Fe, Ni, Pd and Pt, preferably complexes having a ligand containing at least one oxygen atom as a binding site, for example, preferably a CO ligand or a ligand containing at least one carboxyl group or a cyclopentadienyl ligand; and main group metal complexes.

13. Electronic device according to one or more of claims 1 to 12, characterized in that The ratio of compound C1 to compound C2 in layer A is between 80:20 and 20:

80.

14. Electronic device according to one or more of claims 1 to 13, characterized in that At least one of the stacks of first and second layers comprises a hole-transport layer, which adjoins layer A as hole-injection layer, wherein the hole-transport layer comprises the same compound C1 as layer A.

15. A method for producing an electronic device according to one or more of claims 1 to 14, characterized in that The compound C1 is first mixed with the compound C2 and the resulting mixture is then used to produce the layer A by vapor deposition.

16. Use of a mixture comprising at least one compound C1 having hole-transport properties and at least one compound C2 having a HOMO of less than -5.1 eV for producing layer A of an electronic device according to one or more of claims 1 to 14.

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