Organic electronic device, organic semiconducting material and a borane compound

Abstract

Organic electronic device comprising a borane compound of formula (II) wherein Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q 2 They can optionally be connected to each other to form a ring; and Z is an anionic ligand, wherein the anionic ligand has the formula (Ia) where A 1 to A 2 are independently selected from CO or SO2; and R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 They can be connected to each other to form a ring.

Description

[0001] The present invention relates to an organic electronic device, an organic semiconducting material and a borane compound. TECHNICAL BACKGROUND

[0002] Organic light-emitting diodes (OLEDs), which are self-emitting devices, have a wide viewing angle, excellent contrast, fast response time, high brightness, outstanding operating voltage characteristics, and color rendering. A typical OLED comprises an anode, a high-hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, which are stacked sequentially on a substrate. In this context, the HTL, EML, and ETL are thin films made of organic and / or organometallic compounds.

[0003] When a voltage is applied to the anode and cathode, the holes injected from the anode electrode move through the high-temperature transfer (HTL) into the electron microlayer (EML), and the electrons injected from the cathode electrode move through the electron microlayer (ETL) into the EML. The holes and electrons recombine in the EML to generate excitons. When the excitons decay from an excited state to a ground state, light is emitted. The injection and flux of holes and electrons must be balanced so that an OLED with the structure described above exhibits excellent efficiency.

[0004] WO 2017 / 029370 A1 discloses metal amides and their use as a hole injection layer for organic light-emitting diodes.

[0005] Angewandte Chemie, International Edition 2011, 50, 2098-2101, discloses as an air-sensitive, vacuum-distillable, dense liquid, a compound having a composition C 10 H 14B F6N O4 S2 structure and assigned a Chemical Abstract Service number 1283232-76-7.

[0006] WO 2017 / 029366 A1 discloses a hole injection layer for an organic light-emitting diode comprising a triarylamine compound doped with a charge-neutral metal amide compound, wherein the hole injection layer has a thickness of 20 to 1,000 nm.

[0007] WO 2006 / 177 052 ​​A1 discloses the use of aromatic boronic acid or boric acid derivatives in organic electronic devices, in particular electroluminescent devices.

[0008] However, there remains a need to improve the performance of organic electronic devices and / or organic semiconducting materials, in particular optoelectronic devices comprising an organic charge transport material, such as organic light-emitting diodes (OLEDs) or organic photovoltaic (OPV) devices, and complex devices comprising said optoelectronic devices, such as OLED displays.

[0009] It is therefore an object of the present invention to provide organic electronic devices and / or organic semiconducting materials that overcome the disadvantages of the prior art, in particular to provide organic electronic devices / organic semiconducting materials comprising hole transport materials, hole injection materials, hole-generating materials or two or more thereof, in order to improve the performance of such devices, in particular with regard to the input voltage, efficiency or voltage stability thereof. SUMMARY OF THE INVENTION

[0010] This problem is solved by an organic electronic device comprising a borane compound of formula (II) wherein Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q 2They can optionally be connected to each other to form a ring; and

[0011] Z is an anionic ligand, where the anionic ligand has the formula (Ia). A 1 to A 2 are independently selected from CO and SO2; and R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 They can be connected to each other to form a ring.

[0012] Groups A 1 to A 2 , which are contained in the anionic ligand with the formula (Ia), are electron-withdrawing groups.

[0013] According to the invention, the groups R 1 and R 2 The anionic ligands with formula Ia, which are contained within the anionic ligand, are linked together to form a ring. This means that the groups R 1 and R 2They can be connected to each other by means of a covalent bond, in particular by means of a covalent single bond. In this context, the connection between the two groups R 1 and R 2 such that a hydrogen atom of the R 1 -group and a hydrogen atom of the R 2 The -group is replaced by the connecting covalent bond.

[0014] Surprisingly, the inventors discovered that organic electronic devices, as defined above, comprising the borane compound according to the invention, exhibit improved electronic properties, particularly with regard to input voltage, quantum efficiency and voltage stability.

[0015] It may be provided that the boron atom is directly bonded by means of a covalent bond to at least one nitrogen atom included in the anionic ligand. In this context, it may be provided that the nitrogen atom directly bonded to the boron atom is one of the nitrogen atoms explicitly shown in formula (Ia), as stated above (which in the preceding formulas carry the negative charge), i.e., it may be provided that the nitrogen atom directly bonded to the boron atom is not one of the nitrogen atoms possibly included in groups R 1 to R 2 These groups are present if they are selected from N-containing heteroalkyl or N-containing heteroaryl compounds. In this way, it is possible to improve the properties of the organic electronic device, particularly with regard to its input voltage, quantum efficiency, and / or voltage stability.

[0016] It should be understood that the term “electrical properties” refers to the injection and / or transport of electrons in semiconducting materials and layers present in the device as defined herein.

[0017] Regarding the organic electronic device, it can be provided that the organic electronic device comprises a first electrode, a second electrode, and an organic semiconducting layer, wherein the organic semiconducting layer is arranged between the first and the second electrodes and the organic semiconducting layer comprises the borane compound. In this way, it is possible to improve the properties of the organic electronic device, in particular with regard to its input voltage, quantum efficiency, and / or voltage stability.

[0018] Furthermore, the organic semiconducting layer can be configured as a hole injection layer, a hole transport layer, or a hole-generating layer. This allows for improvements to the properties of the organic electronic device, particularly regarding its input voltage, quantum efficiency, and / or voltage stability.

[0019] In this respect, it may be provided that the organic electronic device comprises two or more of the above-mentioned layers (hole injection layer, hole transport layer and hole-generating layer), and it may be provided that one or all of these layers then comprise the borane compound.

[0020] It may also be provided with regard to the organic electronic device that the organic electronic device is an organic electroluminescent device, an organic transistor, an organic diode or an organic photovoltaic device.

[0021] It may also be provided that the organic electroluminescent device is an organic light-emitting device.

[0022] The organic electronic device according to the invention is an organic electronic device comprising at least one organic semiconducting layer, typically a plurality of organic semiconducting layers. These layers can be produced, for example, by evaporating a chemical compound and depositing it onto a support (or a preceding layer) to form the layer. According to the invention, at least one of the layers of the device can be a hole injection layer, a hole transport layer, or a hole-generating layer and can comprise the borane compound as defined herein. In this context, it can be provided that the borane compound is included in the layer in addition to other materials, for example, in the case that the borane compound is a dopant present in the layer together with a suitable matrix compound.It can also be provided that the relevant layer consists of the borane compound, i.e., that the layer contains no other components (except for impurities that cannot be prevented by standard technical means). In such a case, where the layer consists of the borane compound, the relevant layer can be the injection-molded layer.

[0023] If the borane compound is an electrical dopant, the electrical dopant (which may be embedded in a charge-transport matrix compound) can improve the electrical conductivity of the matrix material and / or the injection of an electrical charge into it. The matrix material in such a layer is the predominant material.

[0024] It should be understood that the term "electrical dopant," as used herein, refers to a compound that enhances the electrical properties of a semiconducting material and / or layer. As a direct result, the conductivity, operating voltage, voltage rise over time, efficiency, or lifetime of a device incorporating the doped semiconducting material and / or layer is improved. The electrical dopant may be non-emitting.

[0025] In the organic electronic device, at least one layer comprising the borane compound can be solid.

[0026] In the organic electronic device, the layer comprising the borane compound can be amorphous. In this context, it is assumed that a bulk material with a glass transition temperature measured by a standard procedure above room temperature will form an amorphous layer if the layer is prepared in the same way as the bulk material (for example, vacuum deposition or by depositing a solution of the material in a specific solvent). The standard procedure is described in the experimental section.

[0027] The layer containing the borane compound can be non-emitting.

[0028] The problem is further solved by an organic semiconducting material comprising a borane compound of formula (II) where Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q2 They can optionally be connected to each other to form a ring; and

[0029] Z is an anionic ligand, wherein the anionic ligand has the formula (Ia), where in formula (Ia) A 1 to A 2 independently selected from CO and SO2; R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 They can be connected to each other to form a ring.

[0030] In this context, embodiments mentioned above with regard to the borane compound included in the organic electronic device are also applicable to the case of the organic semiconducting material, as are the technical effects achieved thereby.

[0031] Surprisingly, the inventors discovered that organic semiconducting materials, as defined above, are helpful in improving the input voltage, quantum efficiency, and voltage stability of an organic electronic device when used in it, particularly when used as a hole injection layer, a hole transport layer, or a hole-generating layer thereof.

[0032] With regard to the organic semiconducting material, it may be provided that it further comprises (in addition to the borane compound) an organic matrix compound.

[0033] The organic semiconducting material can be a hole transport material and the organic matrix compound can be a hole transport matrix compound.

[0034] In this context, it can be provided that the organic hole transport matrix compound comprises a conjugated system of at least 6, alternatively at least 10, alternatively at least 14 delocalized electrons.

[0035] Furthermore, in this context, it may be provided that the organic hole transport matrix compound is selected from the group of organic compounds comprising at least one amine nitrogen substituted with groups independently selected from aryl and heteroaryl. Non-restrictive examples of suitable hole transport matrix materials are given below.

[0036] It should be understood that the term "semiconducting" in this context refers to materials and / or devices that possess an electronic conductivity mechanism. Electric current in semiconductors can be understood as the flow of mobile electrons. This is a crucial difference from electrical devices that utilize ionic conductivity. Such devices (not according to the invention), for example, galvanic cells, comprise an electrolyte containing mobile ions, and the electric current therein flows through the electrolyte via the ion flow.

[0037] Furthermore, the problem is solved by a borane compound of formula (II) where Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q 2 They can optionally be connected to each other to form a ring; and

[0038] Z is an anionic ligand, wherein the anionic ligand has the formula (Ia), where in the formula (Ia) A 1 to A 2 independently selected from the group consisting of CO and SO2; R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 can be connected to each other to form a ring; and the compound of the formula where Z is bis(trifluoromethylsulfonyl)imide is an anionic ligand is excluded.

[0039] Surprisingly, the inventors discovered that the borane compound, as defined above, when used in an organic electronic device or organic semiconducting material, particularly in a hole injection layer, hole transport layer or hole-generating layer, is suitable for improving the input voltage, quantum efficiency or voltage stability of the device in question.

[0040] With regard to the borane compound according to the invention, it can be provided that Q 1 and Q 2 are independently selected from the group consisting of C1-C 30 -Alkyl and C1-C 30 -Cycloalkyl.

[0041] With regard to the borane compound according to the invention, it can further be provided that all A 1 and A 2 SO2 are.

[0042] With regard to the borane compound according to the invention, it can further be provided that R 1 and R 2 Each independently selected from perfluorinated C1-C 30 -Hydrocarbyl.

[0043] It may be provided that the borane compound according to the invention is one or more of the compounds E1-E2 of formula (IIa).

[0044] Compound E3 with formula E3, or a compound E4 of formula (IIa), where Z is the anionic ligand, selected from the structures Z 1 -Z 4

[0045] Using the compounds listed as examples, it is possible to further improve the properties of an organic electronic device that incorporates them, particularly with regard to input voltage, efficiency and / or voltage lifetime.

[0046] The problem is further solved by a method for manufacturing the organic electronic device as defined herein, the method comprising the steps: (1) Dissolving the borane compound of formula (II) where Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q 2 They can optionally be connected to each other to form a ring; and Z is an anionic ligand, wherein the anionic ligand has the formula (Ia), where in formula (Ia) A 1 to A 2 independently selected from CO and SO2; R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 can be connected to each other to form a ring; and (2) Deposition of the borane compound from the solution onto a solid support. The problem is further solved by using the borane compound of formula (II) where Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -Hydrocarbyl, where Q 1 and Q 2 They can optionally be connected to each other to form a ring; and Z is an anionic ligand, wherein the anionic ligand has the formula (Ia), where in formula (Ia) A 1 to A 2 independently selected from CO and SO2; R 1 to R 2 are independently selected from perfluorinated C1-C 30 -Hydrocarbyl, where R 1 and R 2 They can be connected to each other to form a ring, for the production of the organic electronic device. Additional layers

[0047] According to the invention, the electronic device can comprise further layers in addition to those already mentioned. Exemplary embodiments of the corresponding layers are described below. carrier

[0048] The substrate can be any substrate commonly used in the manufacture of electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, it must be a transparent or semi-transparent material, for example, a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be either a transparent or an opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate. anode electrode

[0049] Either the first or the second electrode can be an anode electrode. The anode electrode can be formed by depositing or sputtering a material used to create it. The material used to form the anode electrode can be one with a high work function to facilitate hole injection. Alternatively, the anode material can be selected from materials with a low work function (e.g., aluminum). The anode electrode can be transparent or reflective. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO), can be used to form the anode electrode. The anode electrode can also be formed using metals, typically silver (Ag), gold (Au), or metal alloys. Hole injection layer

[0050] In accordance with the invention, the hole injection layer can comprise the borane compound described in detail above. The hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, die-casting, Langmuir-Blodgett (LB) coating, or similar processes. When the HIL is formed by vacuum deposition, the deposition conditions can vary according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, typical vacuum deposition conditions include a deposition temperature of 100 °C to 500 °C and a pressure of 10 -8 up to 10 -3 Include Torr (1 Torr corresponds to 133.322 Pa) and a deposition rate of 0.1 to 10 nm / sec.

[0051] When HIL is formed using spin coating or printing, the conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties. For example, coating conditions might include a coating speed of approximately 2000 rpm to approximately 5000 rpm and a thermal treatment temperature of approximately 80 °C to approximately 200 °C. Thermal treatment removes a solvent after the coating process.

[0052] The HIL can be formed from any compound commonly used to create an HIL, particularly if the electronic device includes a layer other than the one containing the borane compound. Examples of compounds that can be used to create the HIL include a phthalocyanine compound such as copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0053] In such a case, the HIL can be a pure p-doped layer or can be selected from a p-doped hole transport matrix compound. Common examples of known redox-doped hole transport materials are: copper phthalocyanine (CuPc), whose HOMO level is approximately -5.2 eV, doped with tetrafluorotetracyanoquinonedimethane (F4TCNQ), whose LUMO level is approximately -5.2 eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2 eV) doped with F4TCNQ; α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine) doped with F4TCNQ; α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile (PD1). α-NPD doped with 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) (PD2). The dopant concentrations can be selected between 1 and 20 wt%, preferably between 3 wt% and 10 wt%.

[0054] The thickness of the HIL can range from approximately 1 nm to approximately 100 nm, and for example, from approximately 1 nm to approximately 25 nm. If the HIL thickness is within this range, it can exhibit excellent hole-injecting properties without a substantial disadvantage in terms of operating voltage. Hole transport layer

[0055] According to the invention, the hole transport layer can comprise the borane compound described in detail above.

[0056] The hole transport layer (HTL) can be formed by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) coating, or similar processes. When the HTL is formed using vacuum deposition or spin coating, the deposition conditions may be similar to those used for forming the hole transport layer (HIL). However, the conditions for vacuum or solution deposition may vary depending on the compound used to form the HTL.

[0057] In the event that the HTL does not comprise the borane compound according to the invention, but the borane compound is included in another layer, the HTL can be formed by a compound commonly used for forming an HTL. Suitable compounds are disclosed, for example, in Yasuhihiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and are included by reference. Examples of the compound that can be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (alpha-NPD); and a triphenylamine-based compound, such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and prevent excitons from diffusing into the EML.

[0058] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, furthermore about 20 nm to about 190 nm, furthermore about 40 nm to about 180 nm, furthermore about 60 nm to about 170 nm, furthermore about 80 nm to about 160 nm, furthermore about 100 nm to about 160 nm, furthermore about 120 nm to about 140 nm. A preferred thickness of the HTL can be 170 nm to 200 nm.

[0059] If the thickness of the HTL is in this range, the HTL can have excellent hole-carrying properties without having a substantial disadvantage in the operating voltage. Electron-blocking layer

[0060] The function of the electron-blocking layer (EBL) is to prevent electrons from being transferred from the emitting layer to the hole transport layer, thereby confining electrons to the emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron-blocking layer comprises a triarylamine compound. The triarylamine compound can have a LUMO level closer to vacuum than the LUMO level of the hole transport layer. The electron-blocking layer can have a HOMO level further from vacuum compared to the HOMO level of the hole transport layer. The thickness of the electron-blocking layer can be selected between 2 and 20 nm.

[0061] The electron-blocking layer can comprise a compound of the formula Z below (Z)

[0062] In formula Z, CY1 and CY2 are identical or different from each other and each independently represents a benzene cycle or a naphthalene cycle; Ar1 ​​to Ar3 are identical or different from each other and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group with 5 to 30 carbon atoms; Ar4 is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, and a substituted or unsubstituted heteroaryl group with 5 to 30 carbon atoms; L is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms.

[0063] If the electron-blocking layer has a high triplet level, it can also be called a triplet control layer.

[0064] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or blue emitting layer is used. This allows for higher light emission efficiency from the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds with a triplet level higher than the triplet level of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2 722 908 A1. Emission layer (EML)

[0065] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or similar processes. When the EML is formed using vacuum deposition or spin coating, the deposition conditions can be similar to those used for forming the HIL. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0066] The emitting layer (EML) can be formed from a combination of a host and an emitter dotanate. Examples of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenz-imidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), bis(2-(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2), G3 below, compound 1 below, and compound 2 below.

[0067] The emitter dotander can be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter can be a small molecule or a polymer.

[0068] Examples of red emitter dotantes are PtOEP, Ir(piq)3, and Btp2Ir(acac), but these are not the only examples. These compounds are phosphorescent emitters; however, red-emitting fluorescent dotantes can also be used.

[0069] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3, shown below. Compound 3 is an example of a fluorescent green emitter, and its structure is shown below.

[0070] Examples of phosphorescent blue emitter dots are F₂Irpic, (F₂ppy)₂Ir(tmd) and Ir(dfppz)₃, terfluorene; their structures are shown below. 4,4'-Bis(4-diphenylaminostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), and compound 4 are examples of fluorescent blue emitter dots.

[0071] The amount of emitter dopant can range from approximately 0.01 to approximately 50 parts by weight, based on 100 parts by weight of the host. Alternatively, the emitting layer can consist of a light-emitting polymer. The EML can have a thickness of approximately 10 nm to approximately 100 nm, for example, from approximately 20 nm to approximately 60 nm. If the thickness of the EML is in this range, the EML can exhibit excellent light emission without a substantial disadvantage in operating voltage. Hole-blocking layer (HBL)

[0072] A hole-blocking layer (HBL) can be formed on the EML using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or similar processes to prevent the diffusion of holes into the ETL. If the EML contains a phosphorescent dopant, the HBL can also have a triplet exciton-blocking function.

[0073] When HBL is formed using vacuum deposition or spin coating, the deposition conditions can be similar to those used for HIL formation. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form an HBL can be employed. Examples of compounds used to form HBLs include oxadiazoline derivatives, triazole derivatives, and phenanthroline derivatives.

[0074] The HBL can have a thickness in the range of approximately 5 nm to approximately 100 nm, for example, from approximately 10 nm to approximately 30 nm. If the thickness of the HBL is in this range, the HBL can have excellent hole-blocking properties without a substantial disadvantage in the operating voltage. Electron transport layer (ETL)

[0075] The OLED according to the present invention can contain an electron transport layer (ETL).

[0076] According to different embodiments, the OLED can comprise an electron transport layer or an electron transport layer stack, which includes at least one first electron-transporting sub-layer and at least one second electron-transporting sub-layer.

[0077] By appropriately adjusting the energy levels of specific ETL layers, the injection and transport of electrons can be controlled, and the holes can be effectively blocked. This allows the OLED to have a longer lifespan.

[0078] The electron transport layer of the electronic device can comprise an organic electron transport matrix (ETM) material. Furthermore, the electron transport layer can comprise one or more n-doped atoms. Suitable compounds for the ETM are not particularly restricted. According to one embodiment, the electron transport matrix compound consists of covalently bonded atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably at least 10, delocalized electrons. In one embodiment, the conjugated system of delocalized electrons can be comprised of aromatic or heteroaromatic structural units, as disclosed, for example, in documents EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0079] According to one embodiment, the electron transport layer can be electrically doped with an n-type dopant. According to another embodiment, the electron transport layer can comprise the second electron-transporting sublayer, which is located closer to the cathode than the first electron-transporting sublayer, and only the second electron-transporting sublayer can comprise the electrical n-type dopant.

[0080] The electrical n-doping agent can be selected from electropositive elemental metals and / or metal salts and metal complexes of electropositive metals, in particular from elemental forms, salts and / or complexes of metals selected from alkali metals, alkaline earth metals and rare earth metals. Electron Injection Layer (EIL)

[0081] The optional EIL, which can facilitate the injection of electrons from the cathode, can be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinate (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL; however, the specific conditions can vary depending on the material used to form the EIL.

[0082] The thickness of the EIL can range from approximately 0.1 nm to approximately 10 nm, for example, from approximately 0.5 nm to approximately 9 nm. If the thickness of the EIL is within this range, the EIL can exhibit satisfactory electron-injecting properties without a substantial disadvantage in the operating voltage. cathode electrode

[0083] The cathode electrode is formed on the EIL, if one is present. The cathode electrode can be made of a metal, an alloy, an electrically conductive compound, or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode electrode can be made of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (in), magnesium (Mg)-silver (Ag), or similar materials. Alternatively, the cathode electrode can be made of a transparent conductive oxide such as ITO or IZO.

[0084] The thickness of the cathode electrode can range from approximately 5 nm to approximately 1000 nm, for example, from approximately 10 nm to approximately 100 nm. If the thickness of the cathode electrode is in the range of approximately 5 nm to approximately 50 nm, the cathode electrode can be transparent or semi-transparent, even if it is made of a metal or metal alloy.

[0085] It is important to understand that the cathode electrode is not part of an electron injection layer or the electron transport layer. Charge-generating layer / hole-generating layer

[0086] The charge-generating layer (CGL) can consist of a bilayer. If the charge-generating layer is a p-type charge-generating layer (hole-generating layer), it can comprise the borane compound defined herein.

[0087] Typically, the charge-generating layer is a pn junction, which connects an n-type charge-generating layer (electron-generating layer) and a hole-generating layer. The n-side of the pn junction generates electrons and injects them into the layer adjacent to it, towards the anode. Similarly, the p-side of the pn junction generates holes and injects them into the layer adjacent to it, towards the cathode.

[0088] Charge-generating layers are used in tandem devices, for example in tandem OLEDs which comprise two or more emitting layers between two electrodes. In a tandem OLED with two emitting layers, the n-type charge-generating layer provides electrons for the first light-emitting layer, which is located next to the anode, while the hole-generating layer provides holes for the second light-emitting layer, which is located between the first emitting layer and the cathode.

[0089] According to the invention, the electronic device can be assumed to comprise a hole injection layer and a hole-generating layer. If a layer other than the hole-generating layer comprises the borane compound defined herein, it is not mandatory that the hole-generating layer also comprises the borane compound defined herein. In such a case, the hole-generating layer can consist of an organic matrix material doped with p-type dopant. Suitable matrix materials for the hole-generating layer can be materials commonly used as hole injection and / or hole transport matrix materials. The p-type dopant used for the hole-generating layer can also be of conventional materials.For example, the p-doper can be selected from a group consisting of tetrafluoro-7,7,8,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radial derivatives, iodine, FeCl3, FeF3, and SbCl5. Furthermore, the host can be selected from a group consisting of N,N'-di(naphthalene-1-yl)-N,N-diphenylbenzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthylbenzidine (TNB).

[0090] According to one embodiment, the hole-forming layer comprises the borane compound defined herein as detailed above.

[0091] The n-type charge-generating layer can be a layer of a pure n-doped element, for example, an electropositive metal, or it can consist of an organic matrix material doped with the n-doped element. According to one embodiment, the n-type doped element can be an alkali metal, alkali metal compound, alkaline earth metal, or alkaline earth metal compound. According to another embodiment, the metal can be selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In particular, the n-doped element can be selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. Suitable matrix materials for the electron-generating layer can be materials commonly used as matrix materials for electron injection or electron transport layers.The matrix material can, for example, be one selected from a group consisting of oftriazine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminium, benzazole derivatives and silo derivatives.

[0092] According to one embodiment, the n-type charge-generating layer can contain a compound of the following chemical formula X, wherein each of A1 to A6 is hydrogen, a halogen atom, nitrile (-CN), nitro (-NO2), sulfonyl (-SO2R), sulfoxide (-SOR), sulfonamide (-SO2NR), sulfonate (-SO3R), trifluoromethyl (-CF3), ester (-COOR), amide (-CONHR or -CONRR'), substituted or unsubstituted straight-chain or branched-chain C1-C12 alkoxy, substituted or unsubstituted straight-chain or branched-chain C1-C12 alkyl, substituted or unsubstituted straight-chain or branched-chain C2-C12 alkenyl, substituted or unsubstituted aromatic or non-aromatic heteroring, substituted or unsubstituted aryl, substituted or unsubstituted mono- or di-arylamine, substituted or unsubstituted arylalkylamine or the like.Each of the above edge R' herein can be a substituted or unsubstituted C1-C60 alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted 5- to 7-membered heteroring or the like.

[0093] An example of such an n-type charge-generating layer could be a CNHAT-encompassing layer.

[0094] The hole-generating layer is arranged on top of the n-type charge-generating layer. Organic light-emitting diode (OLED)

[0095] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided comprising a support, an anode electrode formed on the support, a hole injection layer, a hole transport layer, an emitting layer, and a cathode electrode.

[0096] According to one aspect of the present invention, an OLED is provided which comprises: a support; an anode electrode formed on the support, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer and a cathode electrode.

[0097] According to another aspect of the present invention, an OLED is provided which comprises: a support; an anode electrode formed on the support, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer and a cathode electrode.

[0098] According to another aspect of the present invention, an OLED is provided which comprises: a support; an anode electrode formed on the support, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode electrode.

[0099] According to different embodiments of the present invention, OLEDs can be provided which comprise layers arranged between the above-mentioned layers, on the substrate or on the upper electrode.

[0100] According to one aspect, the OLED can comprise a layered structure consisting of a substrate arranged next to an anode electrode, the anode electrode is arranged next to a first hole injection layer, the first hole injection layer is arranged next to a first hole transport layer, the first hole transport layer is arranged next to a first electron blocking layer, the first electron blocking layer is arranged next to a first emission layer, the first emission layer is arranged next to a first electron transport layer, the first electron transport layer is arranged next to a first n-type charge-generating layer, the n-type charge-generating layer is arranged next to a hole-generating layer, the hole-generating layer is arranged next to a second hole transport layer, and the second hole transport layer is arranged next to a second electron blocking layer.The second electron-blocking layer is arranged next to a second emission layer; an optional electron transport layer and / or an optional injection layer is arranged between the second emission layer and the cathode electrode.

[0101] For example, the OLED can be used according to Fig. 2 shall be formed by a method wherein on a support (110) an anode (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), an emission layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180) and the cathode electrode (190) are formed successively in this order. Details and definitions of the invention

[0102] The electronic device according to the present invention comprises at least one (semiconducting) layer, which may include a charge-transport matrix compound and the borane compound. The borane compound may be embedded in the matrix material, i.e., the matrix material is the predominant material in such a layer. It is also possible that the matrix material and the dopant in the semiconducting layer are separated from each other into a first sub-layer comprising the matrix material and a second sub-layer comprising the dopant, or, in a preferred embodiment, each consist of these. It is also possible that the layer consists of the borane compound.

[0103] The borane compound can diffuse into adjacent layers after deposition; in particular, the borane compound can diffuse into the layer onto which it is deposited.

[0104] The organic electronic device described herein can be an organic electronic device based on semiconducting layers. In particular, the hole injection layer, the hole transport layer, and the hole-generating layer are semiconducting layers.

[0105] The term “hydrocarbyl group” as used herein shall be understood to encompass any organic group with carbon atoms, in particular organic groups such as alkyl, aryl, heteroaryl, heteroalkyl, especially those groups which are common substituents in organic electronics.

[0106] The term "alkyl" as used herein is intended to encompass linear, branched, and cyclic alkyl. For example, C3 alkyl can be selected from n-propyl and isopropyl. Similarly, C4 alkyl includes n-butyl, sec-butyl, and t-butyl. Likewise, C6 alkyl includes n-hexyl and cyclohexyl.

[0107] The subscript n in Cn refers to the total number of carbon atoms in the respective alkyl, arylene, heteroarylene or aryl group.

[0108] The term "aryl" as used herein is intended to encompass phenyl (C6-aryl), condensed aromatics such as naphthalene, anthracene, phenanthrene, tetracene, etc. It also includes biphenyl and oligo- or polyphenyls such as terphenyl, etc. Furthermore, it includes all other aromatic hydrocarbon substituents such as fluorenyl, etc. Arylene or heteroarylene refers to groups to which two other units are bonded.

[0109] The term ‘heteroaryl’ used herein refers to aryl groups in which at least one carbon atom is replaced by a heteroatom, preferably selected from N, O, S, B or Si.

[0110] The term "halogenated" refers to an organic compound in which one hydrogen atom has been replaced by a halogen atom. The term "perhalogenated" refers to an organic compound in which all hydrogen atoms have been replaced by halogen atoms. The meaning of the terms "fluorinated" and "perfluorinated" is analogous.

[0111] The subscript n in C n -Heteroaryl refers only to the number of carbon atoms, without considering the number of heteroatoms. In this context, it is clear that a C3 heteroaryl group is an aromatic compound comprising three carbon atoms, such as pyrazole, imidazole, oxazole, thiazole, and the like.

[0112] For the purposes of the invention, the term "between" in relation to a layer located between two other layers does not preclude the presence of further layers that may be arranged between that layer and one of the other two layers. For the purposes of the invention, the term "in direct contact" in relation to two layers that are in direct contact with each other means that no further layers are arranged between these two layers. A layer deposited on the other layer is considered to be in direct contact with that layer.

[0113] In the context of this description, the term "essentially non-emitting" or "non-emitting" means that the contribution of the compound or layer to the visible emission spectrum of the device is less than 10%, preferably less than 5%, based on the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of approximately ≥ 380 nm to approximately ≤ 780 nm.

[0114] Preferably, the organic semiconducting layer, which comprises at least one electrical dopant, is substantially non-emitting or non-emitting.

[0115] With regard to the electronic device according to the invention, the compounds mentioned in the experimental part may be the most preferred.

[0116] The electronic device according to the invention can be an organic electroluminescent device (OLED), an organic photovoltaic device (OPV) or an organic field-effect transistor (OFET).

[0117] According to another aspect, the organic electroluminescent device according to the present invention can comprise more than one emission layer, preferably two or three emission layers. An OLED comprising more than one emission layer is also referred to as a tandem OLED or stacked OLED.

[0118] The organic electroluminescent device (OLED) can be a device that emits from the bottom or the top.

[0119] Another aspect focuses on a device comprising at least one organic electroluminescent device (OLED). A device comprising organic light-emitting diodes is, for example, a display or a lighting panel.

[0120] In this description, the following defined terms shall be used as the definitions, unless another definition is given in the claims or elsewhere in the description.

[0121] In the context of the present description, the term “different” or “distinguish” in relation to the matrix material means that the matrix material is different in its structural formula.

[0122] The energy levels of the most occupied molecular orbital, also called HOMO, and the lowest unoccupied molecular orbital, also called LUMO, are measured in electron volts (eV).

[0123] The terms "OLED" and "organic light-emitting diode" are used interchangeably and have the same meaning. The term "organic electroluminescent device" used here can encompass both organic light-emitting diodes and organic light-emitting transistors (OLETs).

[0124] As used herein, “weight percent”, “wt%”, wt%, “percent weight”, “% weight”, and variations thereof refer to a composition, component, substance, or agent as the weight of that component, substance, or agent of the respective electron transport layer divided by the total weight of that component, substance, or agent of the respective electron transport layer and multiplied by 100. It is understood that the total weight percentage of all components, substances, and agents of the respective electron transport layer and electron injection layer is chosen such that it does not exceed 100 wt%.

[0125] As used herein, “volumetric percent”, “vol%”, “vol-%”, “percent volume”, “% volume”, and variations thereof refer to a composition, component, substance, or agent as the volume of that component, substance, or agent of the respective electron transport layer divided by the total volume of that electron transport layer thereof, multiplied by 100. It is understood that the total percentage volume fraction of all components, substances, and agents of the cathode layer is chosen such that it does not exceed 100 vol%.

[0126] All numerical values ​​herein are modified by the term "approximately," whether explicitly stated or not. As used herein, the term "approximately" refers to the variation in numerical quantity that may occur. Regardless of whether the claims are modified by the term "approximately" or not, they include equivalents of the quantities.

[0127] It should be noted that, as used in this specification and the attached claims, the singular forms “ein”, “eines” and “der / die / das” include multiple references unless the content clearly specifies otherwise.

[0128] The terms "free from", "does not contain", and "do not include" do not exclude impurities. Impurities have no technical effect on the object achieved by the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0129] These and / or other aspects and advantages of the present invention will be evident and easier to recognize from the following description of the exemplary embodiments, which are taken in conjunction with the accompanying drawings: Fig. Figure 1 is a schematic sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Fig. Figure 2 is a schematic sectional view of an OLED according to an exemplary embodiment of the present invention. Fig. Figure 3 is a schematic sectional view of a tandem OLED comprising a charge-generating layer according to an exemplary embodiment of the present invention. FORM OF EXECUTION OF THE DEVICE ACCORDING TO THE INVENTION

[0130] Detailed reference is now made to the exemplary embodiments of the present invention, examples of which are illustrated in the accompanying drawings, where identical reference numerals consistently refer to the same elements. The exemplary embodiments are described below in order to explain the aspects of the present invention with reference to the figures.

[0131] In this context, when a first element is described as formed or as placed "on" a second element, the first element may be placed directly on top of the second element, or one or more other elements may be placed between them. When a first element is described as formed or placed "directly on" a second element, no other elements are placed between them.

[0132] Fig. Figure 1 is a schematic sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 comprises a support 110, an anode 120, a high-intensity hole injection layer (HIL) 130, a high-intensity hole transport layer (HTL) 140, an emission layer (EML) 150, and an electron transport layer (ETL) 160. The electron transport layer (ETL) 160 is formed directly on the EML 150. An electron injection layer (EIL) 180 is arranged on the electron transport layer (ETL) 160. The cathode 190 is arranged directly on the electron injection layer (EIL) 180.

[0133] Instead of a single electron transport layer 160, an electron transport layer stack (ETL) can optionally be used.

[0134] Fig. Figure 2 is a schematic sectional view of an OLED 100 according to a further exemplary embodiment of the present invention. Fig. 2 differs from Fig. 1 by the fact that the OLED 100 of Fig. 2 comprises an electron-blocking layer 145 and a hole-blocking layer (HBL) 155.

[0135] With reference to Fig. 2 the OLED 100 includes a support 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode electrode 190.

[0136] Fig. Figure 3 is a schematic sectional view of a tandem OLED 200 according to a further exemplary embodiment of the present invention. Fig. 3 differs from Fig. 2 by the fact that the OLED 100 of Fig. 3 further comprises a charge-generating layer and a second emission layer.

[0137] With reference to Fig. 3, the OLED 200 includes a support 110, an anode 120, a first hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first electron transport layer (ETL) 160, an n-charge generating layer (n-type CGL) 185, a hole generating layer (p-type charge generating layer; p-type GCL) 135, a second hole transport layer (HTL) 141, a second electron blocking layer (EBL) 146, a second emission layer (EML) 151, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, a second electron injection layer (EIL) 181 and a cathode 190.

[0138] Although in Fig. 1, Fig. 2 and Fig. Figure 3 (not shown) shows that a sealing layer can be formed on the cathode electrodes 190 to seal the OLEDs 100 and 200. Furthermore, various other modifications can be made.

[0139] One or more exemplary embodiments of the present invention are described in detail below with reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention. EXPERIMENTAL SECTION

[0140] The formulas for the supporting materials listed below are as follows: F1 is F2 is F3 is

[0141] ABH-113 is an emitter host material and NUBD-370 and DB-200 are blue fluorescent emitter dots, all commercially available from SFC, Korea.

[0142] ITO is indium tin oxide. Production of exemplary compounds. General manufacturing process A

[0143] A suspension of 0.5 equivalents of 9-borabicyclo[3.3.1]nonanedimer (1.0 equivalent of the monomer) and 1.0 equivalent of the corresponding imide was gently heated in dry toluene under a dry nitrogen atmosphere at 90°C for 1 h. Intense gas release was observed during heating, and a clear solution was formed. The resulting solution was distilled under vacuum. Compounds E2 and E1 were isolated as a single fraction with a boiling point of 100–120°C (1.5 Torr). The solid compounds E4, E5, and E6 were isolated by filtration and washing with dry hexane. Synthesis of compound E3

[0144] A suspension of 0.5 equivalents of the dimesitylhydroborane dimer (1.0 equivalent of the monomer) and 1.0 equivalent of a corresponding imide was gently heated in dry toluene under a dry nitrogen atmosphere at 90°C for 1 h. Intense gas release was observed during heating, and a clear solution was formed. The resulting solution was distilled under vacuum. The product was washed with dry hexane.

[0145] E1 yield 54%, white solid; 1 H-NMR (600 MHz, CDCl3): δ = 1.13-1.15 (m, 1H), 1.37-1.41 (m, 2H), 1.46-1.50 (m, 1H), 1.81-1.94 (m, 10H); 19 F-NMR (377 MHz, CDCl3): δ = -126.12 (m, 4F), -120.93 (m, 4F), -106.17 (br s, 4F), -81.07 (t, J = 9.6 Hz, 6F); further splitting due to multiple 19 F, 19 F-couplings; 11 B-NMR (192 MHz, CDCl3): δ = 59.2 (s).

[0146] E2 yield 51%, yellow viscous liquid; 1 H NMR (600 MHz, C6D6): δ = 1.12-1.15 (m, 2H), 1.61-1.70 (m, 12H); 11 B-NMR (192 MHz, C6D6): δ = 71 (s); 59 (s)

[0147] E3 yield 57%, pale yellow liquid; 1 H NMR (600 MHz, C6D6): δ = 2.14 (s, 6H, 2xMe), 2.27 (s, 12H, 4xMe), 6.74 (s, 4H, H Ar ); 11 B-NMR (192 MHz, C6D6): δ = 57.8 (s).

[0148] E4 Yield 55%, yellow solid; 1 H NMR (600 MHz, C6D6): δ = 1.31-1.36 (m, 3H), 1.87-1.96 (m, 10H), 2.86 (s, 1H); 11 B-NMR (192 MHz, C6D6): δ = 66.0 (s); optional 58.3 (s).

[0149] E5 (not according to the invention) Yield 60%, pale yellow solid; 1 H NMR (600 MHz, C6D6): 1.30-1.32 (m, 2H), 1.83-1.93 (m, 6H), 1.98-2.05 (m, 4H), 2.94 (s, 2H), 6.68-6.72 (m, 2H, H Ar ), 7.11 (d, 3 J = 6.5 Hz, 1H, H Ar ), 7.44 (d, 3 J = 6.3 Hz, 1H, H Ar );11 B-NMR (192 MHz, C6D6): δ = 62.8 (s); optional 58.0 (s)

[0150] E6 (not according to the invention) Yield 58%, pale yellow solid; 1 H-NMR (600 MHz, C6D6): δ = 1.20-1.25 (m, 2H), 1.68-1.76 (m, 2H), 1.80-1.83 (m, 4H), 1.98-2.04 (m, 4H), 2.69 (s, 2H), 6.41-6.42 (m, 2H, H Ar ), 6.95-6.97 (m, 2H, H Ar ); 11 B-NMR (192 MHz, C6D6): δ = 60.7 (s).

[0151] The structures formed are schematic; the observed presence of multiple signals in the 11 B-NMR spectrum is evidence of changing coordination modes of the anionic ligands. Fixture experiments, standard procedures, stress stability

[0152] OLEDs are powered by constant current circuits. These circuits can supply a constant current over a specific voltage range. The larger the voltage range, the greater the power losses of such devices. Therefore, changes in the operating voltage must be minimized.

[0153] The operating voltage of an OLED is temperature-dependent. Therefore, the voltage stability must be assessed at thermal equilibrium. Thermal equilibrium is reached after one hour of operation.

[0154] Voltage stability is measured by measuring the difference between the operating voltage after 50 hours and after 1 hour of operation at a constant current density. A current density of 30 mA / cm² is used. 2 used. The measurements are taken at room temperature. dU[V]=U(50 h,30 mA / cm2)−U(1 h,30 mA / cm2) Examples

[0155] Blue fluorescent OLED comprising a hole injection layer p-doped with an imidoborane compound.

[0156] Table 1a schematically describes a model device. Table 1a Material c [wt%] d [nm] ITO 100 90 F1: p-Dotand 92:8 (mol%#) 45 F2 100 85 ABH113: NUBD370 3 20 F3: LiQ 50 36 Al 100 100 #based on molar amounts of metal atoms

[0157] The results obtained are shown in Table 1b. Table 1b * j = 15 mA / cm 2 U* [V] EQE* [%] CIE-y* U(50 h)-U(1 h) ** [V] ** j = 30 mA / cm 2 Li(TFSI) (Referenz) 4,0 6,2 0,091 1,3 E1 4,1 6,5 0,095 E2 4,0 6,5 0,091 0,4

[0158] Regarding input voltage and EQE, E1 and E2 deliver at least equally good, if not better, results compared to the reference material LiTFSI. Additionally, improved performance in terms of voltage stability is observed for E2.

[0159] The properties disclosed in the preceding description and the dependent claims may, separately or in combination, be the subject of realizing the aspects of the disclosure made in the independent claims in different forms thereof.

[0160] Key symbols and abbreviations used in the registration: CV Cyclic voltammetry DSC Dynamic Differential Calorimetry EBL electron-blocking layer EIL electron injection layer EML emitting layer eq. equivalent ETL electron transport layer ETM Electron Transport Matrix FC Ferrocen FC + Ferricenium HBL hole-blocking layer HIL (Hyper-Injection Layer) HOMO highest occupied molecular orbital HPLC High-performance liquid chromatography HTL perforated transport layer p-HTL p-doped hole transport layer HTM Hole Transport Matrix ITO (Indium Tin Oxide) LUMO: lowest unoccupied molecular orbital mol% Mole percent NMR nuclear magnetic resonance OLED organic light-emitting diode OPV organic photovoltaics PTFE (Polytetrafluoroethylene) QE Quantum efficiency R f Retardation factor in TLC RGB red-green-blue TCO transparent conductive oxide TFT thin-film transistor T g Glass transition temperature TLC thin-layer chromatography VTE thermal vacuum evaporation wt% weight percent

Claims

[1] An organic electronic device comprising a borane compound of formula (II)wherein Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -hydrocarbyl, where Q 1 and Q 2 may optionally be connected to each other to form a ring; and Z is an anionic ligand, wherein the anionic ligand has the formula (Ia)wherein A 1 to A 2 are independently selected from CO or SO2; and R 1 to R 2 are independently selected from perfluorinated C1-C 30 -hydrocarbyl, where R 1 and R 2 can be connected to each other to form a ring. [2] The organic electronic device according to claim 1, wherein the organic electronic device comprises a first electrode, a second electrode and an organic semiconducting layer, wherein the organic semiconducting layer is disposed between the first and second electrodes, and the organic semiconducting layer comprises the borane compound. [3] The organic electronic device according to claim 2, wherein the organic semiconducting layer is a hole injection layer, a hole transport layer or a hole generating layer. [4] An organic electronic device according to any one of the preceding claims, wherein the organic electronic device is an organic electroluminescent device, an organic transistor, an organic diode or an organic photovoltaic device. [5] The organic electronic device of claim 4, wherein the organic electroluminescent device is an organic light-emitting diode. [6] An organic semiconducting material comprising the borane compound as defined in claim 1. [7] Borane compound of formula (II) where Q 1 and Q 2 are independently selected from the group consisting of unsubstituted C1-C 30 -hydrocarbyl, where Q 1 and Q 2 may optionally be connected to each other to form a ring; and Z is an anionic ligand, wherein the anionic ligand has the formula (Ia) wherein in the formula (Ia) A 1 to A 2 are independently selected from the group consisting of CO and SO2; R 1 to R 2 are independently selected from perfluorinated C1-C 30 -hydrocarbyl, where R 1 and R 2can be connected together to form a ring; and the compound of formula where Z is bis(trifluoromethylsulfonyl)imide anionic ligand is excluded.

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