Compound, organic semiconducting material, organic electronic device and display device

Abstract

Combination of the following formula (I) where - R 1 to R 2 independent C1- to C8-hydrocarbyl, which contains at least one sp 3 -hybridized carbon atom comprising the C1- to Cs-hydrocarbyl via a sp 3 -hybridized carbon atom of C1 to C8 -hydrocarbylsan the P atom of formula (I) is bonded; - L 1 , A and L 2 are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L 1 , A and L 2 substituted or unsubstituted phenylene is and / or at least one of L 1 , A and L 2 substituted or unsubstituted naphthylene is; - whereupon, if one or more of L 1 , A and L 2substituted is / are, the one or more substituent(s) is / are independently selected from the group consisting of D, C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12 -Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl; - R 3 to R 9 are independently selected from the group consisting of H, D, C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12 -Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl.

Description

TECHNICAL AREA

[0001] The present invention relates to a compound. The present invention further relates to an organic semiconducting material comprising the compound, an organic electronic device comprising the semiconducting material, a display device comprising the electronic device, and a method for manufacturing the organic electronic device. BACKGROUND OF THE INVENTION

[0002] Organic semiconductor devices, such as organic light-emitting diodes (OLEDs), which are self-emitting devices, exhibit a wide viewing angle, excellent contrast, fast response time, high brightness, excellent 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, stacked sequentially on a substrate. The HTL, EML, and ETL are thin films composed of organic compounds.

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

[0004] The performance of an organic light-emitting diode can be influenced by properties of the organic semiconductor layer and can be influenced by properties of an organic material within the organic semiconductor layer.

[0005] In particular, the development of an organic semiconductor layer capable of increasing electron mobility while simultaneously increasing electrochemical stability is required so that the organic semiconductor device, such as an organic light-emitting diode, can be applied to a large-area flat panel display.

[0006] Furthermore, the development of an organic semiconductor layer capable of extended lifetime at higher current density and thus higher brightness is required. In particular, the development of an organic semiconductor material or layer capable of lowering the operating voltage is necessary, which is important for reducing power consumption and increasing battery life, for example, in a mobile display device.

[0007] It is therefore the object of the present invention to provide compounds and semiconducting materials for the manufacture of organic electronic devices, such as organic light-emitting diodes and display devices, which overcome the disadvantages of the prior art, particularly with regard to power efficiency.

[0008] WO 2018 / 215355 A1 discloses a compound containing phosphorus and an organic electronic device comprising an organic semiconductor layer.

[0009] CN 109 721 598 A discloses a display panel comprising an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a hole injection layer, a hole transmittance layer, an organic light-emitting layer, an electron transmittance layer, an electron injection layer and a cathode; and the organic light-emitting device further comprises a molecular self-assembly layer arranged between the cathode and the electron injection layer.

[0010] WO 2023 / 213 705 A1 discloses an organic light-emitting diode comprising an anode, a cathode, a first emission layer, a second emission layer, a first charge generation layer and a first electron transport layer stack, as well as a display or illumination device comprising this diode. revelation

[0011] This task is accomplished by combining the following formula (I) where - R 1 to R 2 independent C1- to C8-hydrocarbyl, which is at least one sp 3 -hybridized carbon atom comprising the C1- to C8-hydrocarbyl via a sp 3 -hybridized carbon atom of C1 to C8 hydrocarbyl is bonded to the P atom of formula (I); - L 1 , A and L 2 are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L 1 , A and L 2 substituted or unsubstituted phenylene is and / or at least one of L 1 , A and L 2 substituted or unsubstituted naphthylene is; - whereupon, if one or more of L 1 , A and L 2substituted is / are, the one or more substituent(s) is / are independently selected from the group consisting of D, C1 - to C6 - alkyl and substituted or unsubstituted C6 - to C 12 - Aryl, where, if the respective C6 - to C 12 - Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl; - R 3 to R 9 are independently selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C 12 -Aryl, where, if the respective C6 - to C 12 - Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl.

[0012] This problem is solved by an organic semiconducting material comprising the compound according to the present invention.

[0013] This problem is further solved by an organic electronic device comprising the organic semiconducting material according to the present invention.

[0014] This problem is further solved by a display device comprising at least one organic electronic device according to the present invention. Connection

[0015] According to one aspect, the present invention relates to a compound of the following formula (I)

[0016] In formula (I) R 1 and R 2 independently selected as C1- to C8-hydrocarbyl, wherein the C1- to Cs-hydrocarbyl has at least one sp 3 -hybridized carbon atom comprises.

[0017] For the purposes of this disclosure, hydrocarbyl is a monovalent group formed by removing one hydrogen atom from a hydrocarbon, e.g., ethyl, tolyl, etc. A hydrocarbylene is a divalent or polyvalent group formed by removing two or more hydrogen atoms from a hydrocarbon, e.g., ethylene, tolylene, etc.

[0018] It is planned that the C1- to C8-hydrocarbyl will contain at least one sp 3 -comprising a carbon atom.

[0019] A sp 3 -The carbon atom is a sp 3 -hybridized carbon atom, i.e., a tetravalent carbon atom that forms single covalent bonds (sigma bonds) with atoms of other elements, especially p-block elements, such as H, O, C, N, halogens, etc. For example, in an alkane, cycloalkane, polycyclic alkane, etc., all carbon atoms are sp 3 -hybridized.

[0020] R 1 and R2 are about a sp 3 -hybridized carbon atom of the C1- to C8-hydrocarbyl bonded to the P atom of formula (I). In particular, in the case that the respective R 1 and R 2 comprising an aromatic component, the binding of the respective R occurs. 1 - and R 2 The -group is not attached to the P atom via a single bond between the aromatic part and the P atom.

[0021] R 1 and R 2 can be independently selected as C1- to C6-hydrocarbyl, C1- to C5-hydrocarbyl, C1- to C4-hydrocarbyl, C1- to C3-hydrocarbyl, C1- to C2-hydrocarbyl or C1-hydrocarbyl.

[0022] R 1 and R 2 can be independently selected from the group consisting of C1- to C6-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. R 1 and R 2can be independently selected from the group consisting of C1- to C5-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. R 1 and R 2 can be independently selected from the group consisting of C1- to C4-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. R 1 and R 2 can be independently selected from the group consisting of C1- to C3-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. R 1 and R 2 can be independently selected from the group consisting of C1- to C2-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. R 1 and R 2 can be independently selected from the group consisting of methyl, C3- to C6-cycloalkyl and C7-arylalkyl.

[0023] R 1 and R 2 can be independently selected as C1- to Cs-alkyl, C1- to C6-alkyl, C1- to C s -alkyl, C1 - to C4 -alkyl, C1 - to C3 -alkyl, C1 - to C2 -alkyl or methyl.

[0024] L 1 , A and L 2 are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L 1 , A and L 2 substituted or unsubstituted phenylene is and / or at least one of L 1 , A and L 2 substituted or unsubstituted naphthylene.

[0025] If one or more of L 1 , A and L 2 The term "substituted" (i.e., selected as substituted phenylene or substituted naphthylene) refers to the one or more substituents bonded to the phenylene and / or naphthylene, independently selected from the group consisting of D, C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 - Aryl. If the respective C6 - to C 12- If the aryl substitution is / are, the one or more substituents can be / can be independently selected from the group consisting of D and C1- to C6-alkyl. If one or more of L 1 , A and L 2 If the phenylene is / are substituted, i.e., selected as substituted phenylene or substituted naphthylene, the one or more substituents bonded to the phenylene and / or naphthylene may be / be independently selected from the group consisting of D, C1- to C4-alkyl and substituted or unsubstituted phenyl, wherein, if the phenyl is substituted, the one or more substituents are / are independently selected from the group consisting of D and C1- to C4-alkyl. If one or more of L 1 , A and L 2where substituted, i.e. selected as substituted phenylene or substituted naphthylene, the one or more substituent(s) bonded to the phenylene and / or naphthylene may be independently selected from the group consisting of D, C1 to C4 alkyl and unsubstituted phenyl.

[0026] If one or more of L 1 , A and L 2 Whether substituted or unsubstituted naphthylene is / are, the naphthylene may be selected from the group consisting of naphthalene-1,2-diyl and naphthalene-1,5-diyl.

[0027] In the formulas above, “*” represents the binding positions.

[0028] If at least one of L 1 , A and L 2 The phenylene can be independently selected from the group consisting of meta-phenylenes and para-phenylenes.

[0029] It is planned that at least one of L 1 , A and L2 substituted or unsubstituted phenylene is and / or at least one of L 1 , A and L 2 substituted or unsubstituted naphthylene. In other words, it is intended that not all of L 1 , A and L 2 at the same time, they are a direct bond. It is that at least one of L 1 , A and L 2 substituted or unsubstituted phenylene. It may be provided that at least one of L 1 , A and L 2 substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with a C1 to C6 hydrocarbyl group. It may be provided that at least one of L 1 , A and L 2 substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with a selected compound from the group consisting of C1- to C4-alkyl and phenyl. It may be provided that at least one of L 1, A and L 2 substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with a selected compound from the group consisting of tert-butyl and phenyl.

[0030] In formula (I) R 3 to R 9 independently selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C 12 - Aryl. In formula (I) R 3 to R 9 be independently selected from the group consisting of H, D and substituted or unsubstituted C6 to C 12 - Aryl. R 3 to R 9 can be independently selected from the group consisting of H, D, phenyl, biphenylyl, and naphthyl. R 3 to R 9 can be independently selected from the group consisting of H, D, and phenyl. If the respective C6 to C 12- Aryl substituted is / are, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl.

[0031] In formula (I) R 3 to R 6 and R 9 be independently selected from the group consisting of H and D; and R 7 and R 8 can be independently selected from the group consisting of C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12 -Aryl is substituted, the one or more substituent(s) being / are independently selected from the group consisting of D and C1- to C6-alkyl. In formula (I), R 3 to R 6 and R 9 be independently selected from the group consisting of H and D; and R 7 and R 8can be independently selected from the group consisting of substituted or unsubstituted C6 to C 12 -Aryl, where, if the respective C6 - to C 12 - Aryl is substituted, the one or more substituent(s) being / are independently selected from the group consisting of D and C1- to C4-alkyl. In formula (I), R 3 to R 6 and R 9 be independently selected from the group consisting of H and D; and R 7 and R 8 can be independently selected from the group consisting of substituted or unsubstituted phenyl, biphenylyl, and naphthyl, wherein, if the respective phenyl, biphenylyl, and naphthyl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1- to C4-alkyl. In formula (I), R 3 to R 6 and R 9 be independently selected from the group consisting of H and D; and R7 and R 8 can be independently selected from the group consisting of substituted or unsubstituted phenyl, wherein, if the phenyl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C4 alkyl.

[0032] In one embodiment, the combination of formula (I) is represented by the following formula (Ia).

[0033] In one embodiment, the combination of formula (I) is represented by the following formula (Ib).

[0034] The combination of formula (I) can be selected from E1 to E5. Organic semiconducting material

[0035] According to a further aspect, the invention relates to an organic semiconducting material. The organic semiconducting material comprises the compound of formula (I) according to the invention described herein.

[0036] The organic semiconducting material can be an electron-transporting material.

[0037] The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 50% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 60% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 70% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 80% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 90% by weight, based on the total weight of the organic semiconducting material.The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 95% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 98% by weight, based on the total weight of the organic semiconducting material. The organic semiconducting material may consist of the compound of formula (I).

[0038] The organic semiconducting material may, in addition to the compound of formula (I), comprise an electrical dopant, in particular an electrical n-dopant.

[0039] An electrical dopant, especially an n-doper, is understood to be a compound which, when embedded in an electron transport matrix, improves the electron properties of the resulting organic material, particularly with respect to electron injection and / or electron conductivity, compared to the pure matrix under the same physical conditions.

[0040] In the context of the present invention, “embedded in an electron transport matrix” means homogeneously mixed with the electron transport matrix.

[0041] The electrical dopant referred to herein is in particular selected from elemental metals, metal salts, metal complexes and organic radicals.

[0042] In one embodiment, the electrical dopant is selected from alkali metal salts and alkali metal complexes; preferably from lithium salts and organolithium complexes; more preferably from lithium halides and organolithium chelates; even more preferably from lithium fluoride, a lithium quinoline olate, lithium borate, lithium phenolate, lithium pyridinolate, or from a lithium complex with a Schiff base ligand; most preferably - the lithium complex has formula II, III or IV: where A1 to A6 are selected equally or independently from CH, CR, N, O; R is selected either directly or independently from hydrogen, halogen, alkyl or aryl or heteroaryl having 1 to 20 carbon atoms; and more preferably A1 to A6 CH are, - the borate-based organic ligand is a tetra(1H-pyrazole-1-yl)borate, - the phenolate is a 2-(pyridin-2-yl)phenolate, a 2-(diphenylphosphoryl)phenolate, an imidazolephenolate, 2-(pyridin-2-yl)phenolate or 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenolate, - the pyridinolate is a 2-(diphenylphosphoryl)pyridine-3-olate, - the lithium ship base has structure 100, 101, 102 or 103:

[0043] According to one embodiment of the invention, the electron transport layer of the present invention comprises a lithium organo-complex, in particular it may comprise 8-hydroxyquinolinolato-lithium (= LiQ).

[0044] According to one embodiment of the present invention, the electron transport layer comprises a metal, preferably selected from alkali metals, alkaline earth metals, rare earth metals and transition period metals Ti, V, Cr and Mn, in particular selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, Tm, Yb; more preferably from Li, Na, K, Rb, Cs, Mg and Yb, even more preferably from Li, Na, Cs and Yb, most preferably from Li, Na and Yb.

[0045] The most practical measure of the strength of an n-dopant is the value of its redox potential. There is no particular limit to how negative the redox potential value can be.

[0046] Since reduction potentials of common electron transport matrices used in organic semiconductors, when measured by cyclic voltammetry against a ferrocene / ferrocenium reference redox couple, are approximately in the range of -0.8 V to -3.1 V; the practically applicable range of redox potentials for n-type dopants that can effectively n-dope such matrices is in a somewhat broader range of approximately -0.5 V to -3.3 V.

[0047] The measurement of redox potentials is practically carried out for a corresponding redox couple, which consists of the reduced and the oxidized form of the same compound.

[0048] In the case that the n-type dopant is an electrically neutral metal complex and / or an electrically neutral organic radical, the measurement of its redox potential is actually performed for the redox couple formed by (i) the electrically neutral metal complex and its cation radical formed by abstraction of an electron from the electrically neutral metal complex, or (ii) the electrically neutral organic radical and its cation formed by abstraction of an electron from the electrically neutral organic radical.

[0049] Preferably, the redox potential of the electrically neutral metal complex and / or the electrically neutral organic radical can have a value that is more negative than -0.5 V, preferably more negative than -1.2 V, more preferably more negative than -1.7 V, even more preferably more negative than -2.1 V, and most preferably more negative than -2.5 V when measured by cyclic voltammetry against a ferrocene / ferrocenium reference redox couple for a corresponding redox couple consisting of (i) the electrically neutral metal complex and its cation radical formed by abstraction of an electron from the electrically neutral metal complex, or (ii) the electrically neutral organic radical and its cation, which is formed by abstraction of an electron from the electrically neutral organic radical.

[0050] In a preferred embodiment, the redox potential of the n-doping agent lies between the value that is about 0.5 V more positive and the value that is about 0.5 V more negative than the value of the reduction potential of the selected electron transport matrix.

[0051] Electrically neutral metal complexes suitable as n-type dopants can be, for example, strongly reductive complexes of some transition metals in a low oxidation state. Particularly strong n-type dopants can be selected, for example, from Cr(II), Mo(II) and / or W(II) guanidinate complexes, such as W2(hpp)4, as described in more detail in WO2005 / 086251.

[0052] Electrically neutral organic radicals suitable as n-type dopants can be, for example, organic radicals generated from their stable dimers, oligomers, or polymers by the supply of additional energy, as described in more detail in EP 1 837 926 B1, WO2007 / 107306, or WO2007 / 107356. An elemental metal is understood to be a metal in a state of pure metal, a metal alloy, or in a state of free atoms or metal clusters. It is understood that metals deposited from a metallic phase, e.g., from a pure bulk metal, by vacuum thermal evaporation evaporate in their elemental form. It is further understood that if the evaporated elemental metal is deposited together with a covalent matrix, the metal atoms and / or clusters are embedded in the covalent matrix.In other words, it is understood that any metal-doped covalent material produced by vacuum thermal evaporation contains the metal at least partially in its elemental form.

[0053] For use in consumer electronics, only metals containing stable radionuclides or radionuclides with a very long half-life of radioactive decay would be suitable. The nuclear stability of natural potassium can be considered an acceptable level.

[0054] In one embodiment, the electrical dopant can be selected from electropositive metals, specifically from alkali metals, alkaline earth metals, rare earth metals, and metals of the first transition period, such as Ti, V, Cr, and Mn. Preferably, the n-dopant can be selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, Tm, and Yb; more preferably from Li, Na, K, Rb, Cs, Mg, and Yb; even more preferably from Li, Na, Cs, and Yb; and most preferably from Li, Na, and Yb. Organic electronic device

[0055] According to one aspect, the invention relates to an organic electronic device. The organic electronic device comprises a first electrode, a second electrode, and an organic semiconducting layer. The organic semiconducting layer is arranged between the first electrode and the second electrode. The organic semiconducting layer consists of the organic semiconducting material according to the present invention, that is to say, it comprises or consists of the compound of formula (I) according to the present invention.

[0056] The organic electronic device can be an organic light-emitting diode (OLED). The organic light-emitting diode can comprise an anode, a cathode, a first light-emitting layer, and a semiconducting layer. where - the first light-emitting layer is positioned between the anode and the cathode; - the semiconducting layer is arranged between the first light-emitting layer and the cathode; and - the semiconducting layer comprises the organic semiconducting material according to the present invention.

[0057] The semiconducting layer can consist of the organic semiconducting material according to the present invention.

[0058] The organic light-emitting diode can comprise two or more semiconducting layers, each comprising a semiconducting material according to the invention.

[0059] The semiconducting layer can be an electron injection layer, an electron transport layer, a hole-blocking layer, or an n-type charge generation layer. The semiconducting layer can be an electron transport layer.

[0060] The semiconducting layer can be an electron transport layer, and the OLED can further comprise an n-type charge generation layer, and the electron transport layer can be arranged between and in direct contact with the first emission layer and the n-type charge generation layer.

[0061] The organic electronic device, in particular the organic light-emitting diode according to the invention, may, in addition to the semiconducting layer comprising or consisting of the semiconducting material according to the invention, comprise further layers. Exemplary embodiments of the respective layers are described below: substrate

[0062] The substrate can be any substrate commonly used in the fabrication of electronic devices, such as organic light-emitting diodes (OLEDs). If light is to be emitted through the substrate, it should be a transparent or semi-transparent material, such as 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

[0063] Either a first electrode or a second electrode contained in the organic electronic device according to the invention can be an anode electrode. The anode electrode can be formed by depositing or sputtering a material used to form the anode electrode. The material used to form the anode electrode can be a material with a high work function to facilitate hole injection. The anode material can also be selected from a material with a low work function (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. 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

[0064] A hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, or similar processes. When the HIL is formed using vacuum deposition, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties. Generally, however, vacuum deposition conditions can include a deposition temperature of 100 °C to 500 °C, a pressure of 10⁻⁸ to 10⁻³ Torr (1 Torr equals 133,322 Pa), and a deposition rate of 0.1 to 10 nm / s.

[0065] When HIL is formed using rotational coating or printing, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of approximately 2000 rpm to approximately 5000 rpm and a heat treatment temperature of approximately 80 °C to approximately 200 °C.

[0066] The HIL can be formed from any compound commonly used to form an HIL. Examples of compounds that can be used to form 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).

[0067] The HIL may include or consist of a p-type dopant, and the p-type dopant may be selected from, but are not limited to, tetrafluorotetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile, or 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). The HIL may be selected from a hole-transporting matrix compound doped with a p-type dopant. Typical examples of known doped hole-transporting materials are: copper phthalocyanine (CuPc), whose HOMO content is about -5.2 eV, doped with tetrafluorotetracyanoquinonedimethane (F4TCNQ), whose LUMO content is about -5.2 eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2 eV). eV), doped with F4TCNQ; α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzamide), doped with F4TCNQ; α-NPD, doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile. The p-type dopant concentrations can be obtained from 1 to 20 wt.-%, preferably selected from 3 wt. % to 10 wt. %.

[0068] 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 thickness of the HIL is within this range, the HIL can exhibit excellent hole injection properties without significantly affecting the drive voltage. Hole transport layer

[0069] A hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or similar processes. If the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for HIL formation. However, the vacuum or solution deposition conditions may vary depending on the compound used to form the HTL.

[0070] The HTL can be formed from any compound commonly used to form an HTL. Compounds that can be suitable for use are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and included by reference. Examples of compounds 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"-TrisCN-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and prevent excitons from diffusing into the EML.

[0071] The thickness of the HTL can be in the range of approximately 5 nm to approximately 250 nm, preferably approximately 10 nm to approximately 200 nm, further approximately 20 nm to approximately 190 nm, further approximately 40 nm to approximately 180 nm, further approximately 60 nm to approximately 170 nm, further approximately 80 nm to approximately 160 nm, further approximately 100 nm to approximately 160 nm, further approximately 120 nm to approximately 140 nm. A preferred thickness of the HTL can be 170 nm to 200 nm.

[0072] If the thickness of the HTL is within this range, the HTL can exhibit excellent hole transport properties without significantly affecting the drive voltage. Electron blocking layer

[0073] The function of an electron blocking layer (EBL) is to prevent electrons from being transferred from an emission layer to a hole transport layer, thereby confining electrons to the emission 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 content closer to the vacuum level than the LUMO content of the hole transport layer. Conversely, the electron blocking layer can have a HOMO content further from the vacuum level than the HOMO content of the hole transport layer. The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0074] If the electron blocking layer has a high triplet content, it can also be described as a triplet control layer.

[0075] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or blue emission layer is used. This allows for higher light emission efficiency from the phosphorescent emission layer. The triplet control layer is selected from triarylamine compounds with a triplet content higher than that of the phosphorescent emitter in the adjacent emission layer. Suitable compounds for the triplet control layer, particularly the triarylamine compounds, are described in EP 2 722 908 A1. Photoactive layer (PAL)

[0076] The photoactive layer converts an electric current into photons or photons into an electric current.

[0077] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or similar processes. When the PAL is formed using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for HIL formation. However, the deposition and coating conditions may vary depending on the compound used to form the PAL.

[0078] It may be provided that the photoactive layer does not include the compound of formula (1).

[0079] The photoactive layer can be a light-emitting layer or a light-absorbing layer. Emission layer (EML)

[0080] 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 and coating 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 EML.

[0081] It may be provided that the emission layer does not comprise the compound according to the present invention, such as the first matrix compound.

[0082] The respective emission layer (EML) can be formed from a combination of a host and an emitter dopant. Examples of hosts are Alq3, 4,4'-N,N'-Dicarbazolebiphenyl (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-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2), EML3 below, compound 1 below, and compound 2 below.

[0083] The emitter dopant 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.

[0084] Examples of red emitter dopants include PtOEP, Ir(piq)3, and Btp2lr(acac), but these are not the only examples. These compounds are phosphorescent emitters; however, fluorescent red emitter dopants could also be used.

[0085] 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.

[0086] Examples of phosphorescent blue emitter dopants are F₂Irpic, (F₂ppy)₂Ir(tmd) and Ir(dfppz)₃, terfluorene; their structures are shown below. 4,4'-Bis(4-diphenylamiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), and compound 4 below are examples of fluorescent blue emitter dopants.

[0087] 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 emission 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 within this range, the EML can exhibit excellent light emission without significantly affecting the drive voltage. Hole-blocking layer (HBL)

[0088] A hole-blocking layer (HBL) can be formed on the EML using vacuum deposition, rotational coating, slot die coating, printing, casting, LB deposition, or similar processes to prevent the diffusion of holes into the ETL. If the EML includes a phosphorescent dopant, the HBL can also exhibit triplet exciton blocking functionality.

[0089] The HBL can also be referred to as auxiliary ETL or a-ETL.

[0090] When HBL is formed using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those 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 oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0091] 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 within this range, the HBL can exhibit excellent hole-blocking properties without significantly affecting the drive voltage.

[0092] The hole-blocking layer can be made of a semiconducting material according to the invention, that is, it can be the semiconducting layer in the organic light-emitting diode according to the invention. Electron transport layer (ETL)

[0093] The organic electronic device according to the present invention can comprise an electron transport layer (ETL).

[0094] According to various embodiments, the OLED can comprise an electron transport layer or an electron transport layer stack comprising at least one first electron transport layer and at least one second electron transport layer.

[0095] By appropriately adjusting the energy levels of specific layers of the ETL, the injection and transport of electrons can be controlled, and the holes can be efficiently blocked. This allows the OLED to have a long lifespan.

[0096] The electron transport layer can comprise ETM materials that include one or more electron transport compound(s) known in the prior art.

[0097] According to one embodiment, the electron transport layer comprises an electron transport compound, wherein the electron transport compound comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with C1 to C4 alkyl. In this respect, an aromatic or heteroaromatic ring is a single aromatic ring, for example, a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl, etc. In a system of fused (hetero)aromatic rings, each ring is considered a single ring in this respect. For example, naphthalene comprises two aromatic rings.

[0098] The electron transport compound can comprise at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings and optionally 1 or 2 heteroaromatic rings.

[0099] The aromatic or heteroaromatic rings of the electron transport compound can be 6-membered rings.

[0100] The heteroaromatic rings of the electron transport compound can be an N-containing heteroaromatic ring, or, if applicable, all heteroaromatic rings are N-containing heteroaromatic rings, or, if applicable, all heteroaromatic rings contain N as the only type of heteroatom.

[0101] The electron transport compound can comprise at least one six-membered heteroaromatic ring containing one to three N atoms in each heteroaromatic ring, optionally one to three 6-membered heteroaromatic rings containing one to three N atoms in each heteroaromatic ring.

[0102] The at least one 6-membered heteroaromatic ring contained in the electron transport compound can be an azine. The at least one 6-membered heteroaromatic ring contained in the electron transport compound can be triazine, diazine, pyrazine, pyrimidine, pyridine, quinazoline, or bonzoquinazoline, preferably triazine.

[0103] If the electron transport compound comprises two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring that is free of a heteroatom.

[0104] In one embodiment, the heteroatoms in the heteroaromatic rings of the electron transport compound are bound into the molecular structure of the electron transport compound by at least one double bond.

[0105] Furthermore, the electron transport layer can comprise one or more additives. The additive can be an n-type dopant. The additive can be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In 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 another embodiment, the n-type dopant can be selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. In one embodiment, the alkali metal compound can be 8-hydroxyquinolinolatolithium (LiQ), lithium tetra(1H-pyrazole-1-yl)borate, or lithium 2-(diphenylphosphoryl)phenolate. Suitable compounds for the ETM (which can be used in addition to the compound according to the invention as defined above) are not particularly limited.In one embodiment, the electron transport matrix compounds consist 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 may be contained in aromatic or heteroaromatic structural units, as disclosed, for example, in documents EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0106] The electron transport layer can have a thickness of approximately 1 to approximately 100 nm, such as approximately 10 to approximately 50 nm.

[0107] The electron transport layer can comprise or consist of the organic semiconducting material according to the invention, i.e., it can be the organic semiconducting layer in the organic electronic device according to the invention. Electron Injection Layer (EIL)

[0108] 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-hydroxyquinoline oleate (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, particularly Yb, which are known in the art. Deposition and coating conditions for forming the EIL are similar to those for forming the HIL, although the specific conditions may vary depending on the material used to form the EIL.

[0109] 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 injection properties without significantly affecting the drive voltage.

[0110] The electron injection layer can comprise the organic semiconducting material according to the invention, i.e., it can be the organic semiconducting layer in the organic electronic device according to the invention. cathode electrode

[0111] The cathode electrode is formed on the EIL, if present. The cathode electrode can be formed from 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 formed from 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 the like. Alternatively, the cathode electrode can be formed from a transparent conductive oxide, such as ITO or IZO. The cathode can comprise more than 50 vol% metal selected from Ag and Au.

[0112] 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.

[0113] The cathode can be a semi-transparent metal cathode with a thickness of less than 20 nm, preferably less than 15 nm.

[0114] It is understood that the cathode electrode is not part of an electron injection layer or the electron transport layer. Charge generation layer / hole generation layer

[0115] The organic electronic device according to the present invention can comprise a charge-generating layer. The charge-generating layer (CGL) consists of a bilayer.

[0116] The charge-generating layer is a pn junction that connects an n-type charge-generating layer (electron-generating layer) and a p-type charge-generating layer (hole-generating layer). The n-side of the pn junction generates electrons and injects them into the layer adjacent to the anode. Similarly, the p-side of the pn junction generates holes and injects them into the layer adjacent to the cathode.

[0117] Charge generation layers are used in tandem devices, for example in tandem OLEDs, which include two or more emission layers between two electrodes. In a tandem OLED with two emission layers, the n-type charge generation layer provides electrons for the first light-emitting layer, which is located near the anode, while the p-type charge generation layer provides holes for the second light-emitting layer, which is located between the first emission layer and the cathode.

[0118] The hole-generating layer (p-type charge-generating layer) can consist of an organic matrix material doped with a p-type dopant. Suitable matrix materials for the hole-generating layer can be materials conventionally used as hole injection and / or hole transport matrix materials. Furthermore, the p-type dopant used for the hole-generating layer can be a conventional material. For example, the p-type dopant can be selected from the group consisting of tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radial derivatives, iodine, FeCl3, FeF3, and SbCl5. Furthermore, the host can be one selected from a group consisting of N,N'-Di(naphthalen-1-yl)-N,N-diphenylbenzamide (NPB), N,N'-Diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD) and N,N',N'-Tetranaphthylbenzamide (TNB).

[0119] The n-type charge-generating layer can be a layer of pure n-doper, for example, an electropositive metal, or it can consist of an organic matrix material doped with the n-doper. In one embodiment, the n-type doper can be an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound. In 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-type doper 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 those materials conventionally 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 triazine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminium, benzazole derivatives and silo derivatives.

[0120] The n-type charge-generating layer can comprise the semiconducting material according to the invention, that is, it can be the semiconducting layer in the organic light-emitting diode according to the invention.

[0121] In one embodiment, the p-type charge-generating layer can include compounds of the following chemical formula X, where 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-C 12- Alkoxy, substituted or unsubstituted straight-chain or branched-chain C1 - C 12 - Alkyl, substituted or unsubstituted straight-chain or branched-chain C2 - C 12 - Alkenyl, a substituted or unsubstituted aromatic or non-aromatic heteroring, a substituted or unsubstituted aryl, a substituted or unsubstituted mono- or diarylamine, a substituted or unsubstituted aralkylamine, or the like. Herein, any of the above R and R' can be a substituted or unsubstituted C1-C 60 - Alkyl, substituted or unsubstituted aryl or a substituted or unsubstituted 5- to 7-membered heteroring or the like.

[0122] An example of such a p-type charge-generating layer could be a layer comprising CNHAT.

[0123] The hole-generating layer can be arranged on the n-type charge-generating layer.

[0124] Regarding the method for manufacturing the organic light-emitting diode, the alternative embodiments described above can be applied accordingly. For example, the charge-generating layer can be produced with an intermediate layer placed between the n-type sublayer and the p-type sublayer.

[0125] According to one aspect, the OLED according to the present invention can comprise a layered substrate structure arranged adjacent to an anode electrode, wherein the anode electrode is arranged adjacent to a first hole injection layer, wherein the first hole injection layer is arranged adjacent to a first hole transport layer, wherein the first hole transport layer is arranged adjacent to a first electron blocking layer, wherein the first electron blocking layer is arranged adjacent to a first emission layer, wherein the first emission layer is arranged adjacent to a first electron transport layer, wherein the first electron transport layer is arranged adjacent to an n-type charge generation layer (n-type sublayer), wherein the n-type charge generation layer is arranged adjacent to a p-type hole generation layer.wherein an intermediate layer is provided between the n-type sublayer and the p-type sublayer, wherein the hole-generating layer is arranged adjacent to a second hole-transport layer, wherein the second hole-transport layer is arranged adjacent to a second electron-blocking layer, wherein the second electron-blocking layer is arranged adjacent to a second emission layer, and wherein an optional electron-transport layer and / or an optional injection layer is arranged between the second emission layer and the cathode electrode. Display device

[0126] According to another aspect, the invention relates to a display device comprising the organic light-emitting diode according to the invention.

[0127] The display device can be a television, a tablet, or a mobile phone. Method for the production of organic light-emitting diodes

[0128] According to another aspect, the invention relates to a method for manufacturing the organic electronic device according to the present invention, wherein the method comprises a step of depositing the compound of formula (I) according to the present invention on a solid support.

[0129] The separation process may include the following: - Separation by vacuum thermal evaporation; - Deposition by solution processing, wherein the processing is preferably selected from rotational coating, printing, casting; and / or - Slotted nozzle coating. Details and definitions of the invention

[0130] An organic compound referred to herein is generally any chemical compound containing carbon (with the exception of some compounds generally described as inorganic, such as carbonates, cyanides, carbon dioxide, diamond, etc.). The term organic compound used herein also includes compounds such as organometallic compounds, for example, metallocenes, etc.

[0131] Unless explicitly stated otherwise, all compounds, groups, units, substituents, etc. shown herein, in particular by structural formulas, by systematic names, etc., include their respective partially and fully deuterated derivatives.

[0132] The term "zero-valent," as used herein, refers to a metal in an oxidation state of 0, that is, specifically metals from which no electron has been removed. The zero-valent metal can exist in the form of zero-valent atoms, pure metal, alloys, etc.

[0133] The term “trivalent”, as used herein, refers to a nitrogen atom with a single bond and a double bond and containing a single pair of electrons.

[0134] The term “hydrocarbyl group”, as used herein, is to be understood as encompassing any organic group comprising carbon atoms, in particular organic groups such as alkyl, aryl, heteroaryl, heteroalkyl, especially those groups which are common substituents in organic electronics.

[0135] The term “conjugated system”, as used herein, refers to a system of alternating π and σ bonds or a molecule with alternating single and multiple bonds, i.e. a double bond or a system with one or more two-atom structural units in which the π bond between its atoms may be replaced by an atom carrying at least a single pair of electrons, typically a divalent O or S atom.

[0136] The term "alkyl," as used herein, encompasses linear, branched, and cyclic alkyl. For example, C3 alkyl can be selected from n-propyl and isopropyl. Likewise, C4 alkyl includes n-butyl, sec-butyl, and t-butyl. Similarly, C6 alkyl includes n-hexyl and cyclohexyl.

[0137] The subscribed number n in C n refers to the total number of carbon atoms in the respective alkyl, arylene, heteroarylene or aryl group.

[0138] The term "aryl" or "arylene," as used herein, includes phenyl (C6 aryl), condensed aromatics such as naphthalene, anthracene, phenanthrene, tetracene, etc. It also includes biphenyl and oligo- or polyphenyls such as terphenyl, phenyl-substituted biphenyl, phenyl-substituted terphenyl (such as tetraphenylbenzene groups), etc. "Arylene" or "heteroarylene" refers to groups to which two other units are bonded. In the present description, the term "aryl group" or "arylene group" may refer to a group comprising at least one aromatic hydrocarbon unit, and all elements of the aromatic hydrocarbon unit may have p-orbitals forming a conjugation, for example a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group and the like.Spiro compounds, in which two aromatic units are linked via a spiro atom, such as 9,9'-spirobi[9H-fluoren]yl, are also included. The aryl or arylene group can enclose a monocyclic or polycyclic (i.e., compounds that share adjacent pairs of carbon atoms) functional group with a fused ring.

[0139] The term “heteroaryl,” as used herein, refers to aryl groups in which at least one carbon atom is substituted with a heteroatom. The term “heteroaryl” can refer to aromatic heterocycles with at least one heteroatom, and all elements of the heteroaromatic hydrocarbon unit can have p-orbitals forming a conjugation. The heteroatom can be selected from N, O, S, B, Si, P, Se, preferably from N, O, and S. A heteroarylene ring can comprise at least one to three heteroatoms. Preferably, a heteroarylene ring can comprise at least one to three heteroatoms, each individually selected from N, S, and / or O. As in the case of “aryl” / “arylene,” the term “heteroaryl” includes, for example, spiro compounds in which two aromatic units are linked together, such as spiro[fluorene-9,9'-xanthene].Other examples of heteroaryl groups are diazine, triazine, dibenzofuran, dibenzothiofuran, acridine, benzoacridine, dibenzoacridine, etc.

[0140] The subscript n in C n -Heteroaryl refers only to the number of carbon atoms, excluding 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.

[0141] 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.

[0142] The term “alkenyl”, as used herein, refers to a group of -CR 1 = CR 2 R 3 , which includes a carbon-carbon double bond.

[0143] The term ‘alkoxy’ as used herein refers to a structural fragment of the formula -OR, where R is hydrocarbyl, preferably alkyl or cycloalkyl.

[0144] The term ‘thioalkyl’ as used herein refers to a structural fragment of the formula -SR, where R is hydrocarbyl, preferably alkyl or cycloalkyl.

[0145] In the present description, the term single bond refers to a direct bond and vice versa.

[0146] For the purposes of the invention, a group is “substituted” with another group if one of the hydrogen atoms included in that group is replaced by another group, wherein the other group is the substituent.

[0147] According to the present disclosure, in a formula showing the following bonding situation, any group A can be bonded to any suitable bonding position. In the following situation, where it is shown that the bond of A crosses more than one ring, any group A can be bonded to any suitable bonding position of each ring crossed by the bond.

[0148] 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 layer is arranged between these two layers. A layer deposited on the top surface of another layer is considered to be in direct contact with that layer.

[0149] 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%, relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of approximately ≥ 380 nm to approximately ≤ 780 nm.

[0150] With regard to the organic lighting device according to the invention, the compounds mentioned in the experimental part may be most preferred.

[0151] The organic electroluminescent device (OLED) can be a bottom- or top-emission device.

[0152] Another aspect is directed at a device comprising at least one organic electroluminescent device (OLED). A device comprising organic light-emitting diodes is, for example, a display or a backlit screen.

[0153] In the present invention, the following defined terms shall apply, unless a different definition is given in the claims or elsewhere in this description.

[0154] In the context of the present description, the term “different” or “distinguishes” in connection with the matrix material means that the matrix material differs in its structural formula.

[0155] The energy levels of the highest occupied molecular orbital, also known as HOMO, and the lowest unoccupied molecular orbital, also known as LUMO, are measured in electron volts (eV).

[0156] The terms “OLED” and “organic light-emitting diode” are used interchangeably and have the same meaning. The term “organic electroluminescent device,” as used herein, can encompass both organic light-emitting diodes and organic light-emitting transistors (OLETs).

[0157] As used herein, “weight percent”, “wt%”, wt%, “weight percent”, “wt%”, 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 selected such that it does not exceed 100 wt%.

[0158] As used herein, “volumetric percent”, “vol%”, “volumetric percent”, “vol%”, 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 volumetric percentage of all components, substances, and agents of the cathode layer is selected such that it does not exceed 100 vol%.

[0159] It is assumed herein that all numerical values ​​are modified by the term "approximately," whether explicitly stated or not. As used herein, the term "approximately" refers to variations in numerical magnitude that may occur.

[0160] Regardless of whether they are modified by the term "approximately" or not, the claims include equivalents to the quantities.

[0161] It should be noted that, as used in this description and the attached claims, the singular forms “ein”, “eine” and “der / die / das” include plural references unless the content clearly indicates otherwise.

[0162] The terms "free from", "does not contain", and "do not include" do not exclude impurities. Impurities have no technical effect with regard to the object achieved by the present invention. The term "free from" a compound means that such a compound / material is not intentionally added to the layer during processing.

[0163] Preferably, the semiconducting layer according to the invention and layers in an OLED formed therefrom are substantially non-emitting or non-emitting.

[0164] The operating voltage, also known as U, is measured in volts (V) at 10 milliamperes per square centimeter (mA / cm²). 2 ) measured.

[0165] The candela-per-ampere efficiency, also known as cd / A efficiency, is measured in candela per ampere at 10 milliamperes per square centimeter (mA / cm2).

[0166] External quantum efficiency, also known as EQE, is measured in percent (%).

[0167] The color space is described by the CIE x and CIE y coordinates (International Commission on Illumination 1931). CIE y is particularly important for blue emission. A smaller CIE y value indicates a deeper blue color. Efficiency values ​​are compared at the same CIE y value.

[0168] The highest occupied molecular orbital, also known as HOMO, and the lowest unoccupied molecular orbital, also known as LUMO, are measured in electron volts (eV).

[0169] The terms “OLED”, “organic light-emitting diode”, “organic lighting device”, “organic optoelectronic device” and “organic light-emitting diode” are used simultaneously and have the same meaning.

[0170] The terms "lifespan" and "lifespan" are used simultaneously and have the same meaning.

[0171] The anode and cathode can be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer.

[0172] The room temperature, also known as ambient temperature, is 23 °C.

[0173] The embodiments are illustrated in more detail below with reference to examples. However, the present disclosure is not limited to the following examples. The exemplary aspects will now be discussed in detail. DESCRIPTION OF THE DRAWINGS

[0174] The components mentioned above, as well as the claimed components and the components to be used in the described embodiments according to the invention, are not subject to any special exceptions with regard to their size, shape, material selection and technical concept, so that the selection criteria known in the relevant field can be applied without restrictions.

[0175] Additional details, features, and advantages of the subject matter of the invention are disclosed in the dependent claims and the following description of the respective figures, which illustrate preferred embodiments according to the invention. However, each embodiment does not necessarily represent the full scope of the invention, and therefore, reference is made to the claims and to this document for an interpretation of the scope of the invention. It is understood that both the foregoing general description and the following detailed description are only exemplary and illustrative and are intended to provide a further explanation of the present invention as claimed. Fig. 1 a schematic sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Fig. 2 a schematic sectional view of an OLED according to an exemplary embodiment of the present invention; Fig. 3 is a schematic sectional view of an OLED according to an exemplary embodiment of the present invention; Fig. 4 is a schematic sectional view of an OLED comprising a charge generation layer and two emission layers, according to an exemplary embodiment of the present invention.

[0176] The figures are illustrated in more detail below with reference to examples. However, the present revelation is not limited to the following figures.

[0177] Where a first element is described herein as being formed or arranged "on" or "atop" 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. Where a first element is described as being formed or arranged "directly on" or "directly on" a second element, no other elements are placed between them.

[0178] Fig. Figure 1 is a schematic sectional view of an organic semiconducting device 100 according to an exemplary embodiment of the present invention. The organic semiconducting device 100 comprises a substrate 110, an anode 120, a light-emitting layer (EML) 125, and a semiconducting layer comprising or consisting of the organic semiconducting material according to the invention 160. The semiconducting layer comprising or consisting of the organic semiconducting material according to the invention 160 is formed on the EML 125. A cathode 190 is arranged on the organic semiconducting layer 160.

[0179] Fig. Figure 2 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 substrate 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 on the EML 150. In this embodiment, the electron transport layer is the semiconducting layer according to the invention. 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.

[0180] Fig. Figure 3 is a schematic sectional view of an OLED 100 according to a further exemplary embodiment of the present invention. Fig. 3 differs from Fig. 2 in that the OLED 100 of Fig. 3 comprises an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155. Referring to Fig. 3 The OLED 100 comprises a substrate 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. In this embodiment of Fig. 3 ETL 160 is the semiconducting layer comprising the compound according to the present invention.

[0181] Fig. Figure 4 is a schematic sectional view of an OLED 100 according to a further exemplary embodiment of the present invention. Fig. 4 differs from Fig. 3 in that the OLED 100 of Fig. 4 further comprises a charge generation layer (CGL) and a second emission layer (151). Referring to Fig. 4 The OLED 100 comprises a substrate 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 emission layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (CGL) 185, a p-type hole generation layer (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, and a second electron injection layer. (EIL) 181 and a cathode 190. In this embodiment of Fig. 4 is the first electron transport layer (ETL) 160 the semiconducting layer comprising the compound of formula (I) according to the present invention.

[0182] Although in Fig. 1, Fig. 2, Fig. 3 and Fig. Not shown in Figure 4, a sealing layer can also be formed on the cathode electrodes 190 to seal the OLEDs 100. Various other modifications can also be applied to it.

[0183] The embodiments are illustrated in more detail below with reference to examples. However, the present disclosure is not limited to the following examples. Synthesis method (4'-(2,4-diphenylbenzo[h]quinazolin-9-yl)-[1,1'-biphenyl]-3-yl)dimethylphosphine oxide (E1) Step 1 9-(4-Chlorophenyl)-2,4-diphenylbenzo[h]quinazoline

[0184] A three-necked round-bottom flask was purged with nitrogen and filled with (4-chlorophenyl)boronic acid (CAS 1679-18-1, 1.0 eq, 14.5 g), 9-bromo-2,4-diphenylbenzo[h]quinazoline (CAS 2905346-69-0, 1.0 eq, 40.0 g), tetrakis(triphenylphosphine)palladium(o) (CAS 14221-01-3, 0.01 eq, 1.1 g), and potassium carbonate (CAS 584-08-7, 2 eq, 26.9 g). A deaerated mixture of 800 mL of dioxane and 160 mL of water was added. The reaction mixture was stirred under reflux overnight in a nitrogen atmosphere. After cooling to room temperature, a beige suspension formed. The solid was filtered, washed with dioxane, water, and methanol, and dried. The crude product was dissolved in toluene, the solution filtered through a silica pad, and the solvent evaporated under low pressure. The isolated solid was recrystallized from toluene. Yield: 38.9 g (90%). Step 2 (4'-(2,4-Diphenylbenzo[h]quinazolin-9-yl)-[1,1'-biphenyl]-3-yl)dimethylphosphine oxide

[0185] A 3-necked round-bottom flask was purged with nitrogen and filled with dimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (CAS 2093110-21-3, 1.1 eq, 23.9 g), 9-(4-chlorophenyl)-2,4-diphenylbenzo[h]quinazoline (1.0 eq, 34.3 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.01 eq, 0.5 g), potassium phosphate (CAS 7778-53-2, 3.0 eq, 49.3 g). A deaerated mixture of 340 mL dioxane and 80 mL water was added. The reaction mixture was stirred under reflux overnight in a nitrogen atmosphere. After cooling to room temperature, a gray suspension formed. The solid was filtered, washed with water and methanol, and dried. The crude product was dissolved in chloroform, the solution filtered through a silica pad, and the solvent was evaporated at low pressure.Further purification was carried out by recrystallization of the resulting solid from a mixture of toluene and ethanol, followed by vacuum sublimation. White powder. Yield: 28.5 g (66%). (ESI-MS: 560). (5-(2,4-Diphenylbenzo[h]quinazolin-9-yl)naphthalen-1-yl)dimethylphosphine oxide (E2) Step 1 (5-Bromonaphthalen-1-yl)dimethylphosphine oxide

[0186] A three-necked round-bottom flask was purged with argon and filled with chlorodimethylphosphine (CAS 811-62-1, 1.0 eq, 4.5 g), 1,5-dibromonaphthalene (CAS 7351-74-8, 1.2 eq, 15.5 g), and 300 mL of anhydrous THF, cooled to -75 °C. 2.5 M n-butyllithium (CAS 109-72-8, 1.1 eq, 13.7 g) solution in hexanes was added. The reaction mixture was stirred for 2 hours at -75 °C under an argon atmosphere and left overnight at room temperature. An aqueous solution of hydrogen peroxide was added to the reaction mixture at 5 °C and stirred for one hour. The crude product was extracted in DCM, and the extract was washed with water. Combined organic phases were dried, and the solvent was evaporated. The resulting solid was further purified by column chromatography using a mixture of DCM and methanol as the eluent. Yield: 7.9 g (60%). 2nd step Dimethyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phosphine oxide

[0187] A three-necked round-bottom flask was purged with nitrogen and filled with 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (CAS 73183-34-3, 1.5 eq, 10.6 g), (5-bromonaphthalen-1-yl)dimethylphosphine oxide (1.0 eq, 7.9 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (CAS 72287-26-4, 0.03 eq, 0.6 g), and potassium acetate (CAS 127-08-2, 3 eq, 8.2 g). 200 mL of anhydrous dioxane were added. The reaction mixture was stirred overnight at 80 °C under an argon atmosphere. After cooling to room temperature, a dark solution formed. The solution was diluted with DCM, filtered through a Celite pad, and the solvent was evaporated under low pressure. Further purification of the resulting crude product was carried out by column chromatography using a mixture of DCM and methanol as the eluent. Yield: 8.0 g (87%). Step 3 (5-(2,4-Diphenylbenzo[h]quinazolin-9-yl)naphthalen-1-yl)dimethylphosphine oxide

[0188] A three-necked round-bottom flask was purged with nitrogen and filled with 9-bromo-2,4-diphenylbenzo[h]quinazoline (CAS 2905346-69-0, 1.0 eq, 11.9 g), dimethyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phosphine oxide (1.6 eq, 14.8 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 eq, 0.7 g), and potassium carbonate (CAS 584-08-7, 2 eq, 8.0 g). A deaerated mixture of 180 mL of dioxane and 30 mL of water was added. The reaction mixture was stirred for 3 days at 80 °C under a nitrogen atmosphere. After cooling to room temperature, a beige suspension formed. The solid was filtered, washed with water and methanol, and dried. The crude product was further purified by Soxhlet extraction with chlorobenzene, and final purification was achieved by vacuum sublimation. White powder. Yield: 11.6 g (75%). (ESI-MS: 534). (3-(tert-butyl)-5-(2,4-diphenylbenzo[h]quinazolin-9-yl)phenyl)dimethylphosphine oxide (E3) Step 1 (3-Bromo-5-(tert-butyl)phenyl)dimethylphosphine oxide

[0189] A 3-necked round-bottom flask was purged with nitrogen and filled with dimethylphosphine oxide (CAS 7211-39-4, 1.4 eq, 15.0 g), 1,3-dibromo-5-(tert-butyl)benzene (CAS 129316-09-2, 1.0 eq, 40.0 g), tris(dibenzylideneacetone)dipalladium(0) (CAS 51364-51-3, 0.015 eq, 1.9 g), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (CAS 161265-03-8, 0.03 eq, 2.4 g) and triethylamine (CAS 121-44-8, 3 eq, 41.6 g). 550 mL of deaerated anhydrous toluene were added. The reaction mixture was stirred overnight at 100 °C under a nitrogen atmosphere. After cooling to room temperature, a greenish-yellow suspension formed. Water was then added, and the reaction mixture was neutralized to pH 7 with dilute aqueous HCl. The crude product was extracted from the aqueous phase in dichloromethane (DCM), and the extract was washed with water. The combined organic phases were dried, filtered through a silica pad, and the solvent was evaporated under low pressure.The solid product was then stirred in a mixture of DCM / cyclohexane, filtered, and recrystallized from cyclohexane. Yield: 8.0 g (20%). Step 2 (3-(tert-Butyl)-5-(2,4-diphenylbenzo[h]quinazolin-9-yl)phenyl)dimethylphosphine oxide

[0190] A three-necked round-bottom flask was purged with nitrogen and filled with 2,4-diphenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[h]quinazoline (CAS 2248001-50-3, 1.0 eq, 12.2 g), (3-bromo-5-(tert-butyl)phenyl)dimethylphosphine oxide (1.2 eq, 9.2 g), tetrakis(triphenylphosphine)palladium(o) (CAS 14221-01-3, 0.02 eq, 0.6 g), and potassium carbonate (CAS 584-08-7, 2 eq, 7.4 g). A degassed mixture of 110 mL of dioxane and 30 mL of water was added. The reaction mixture was stirred overnight under a nitrogen atmosphere under reflux. After cooling to room temperature, a yellowish solution formed. The solvent was evaporated at low pressure, the crude product was extracted in DCM, and the extract was washed with water. The combined organic phases were dried, filtered through a silica pad, and the solvent was evaporated at low pressure.The product was then macerated in a mixture of DCM / n-hexane, filtered, dried, and the isolated solid was purified by vacuum sublimation. White powder. Yield: 9.0 g (63%). (ESI-MS: 540). (2-(2,4-Diphenylbenzo[h]quinazolin-9-yl)-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide (E4) Step 1 (2-Bromo-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide

[0191] A 3-necked round-bottom flask was purged with nitrogen and filled with dimethylphosphine oxide (CAS 7211-39-4, 1.4 eq, 8.2 g), 2,4-dibromo-1,1'-biphenyl (CAS 53592-10-2, 1.0 eq, 23.3 g), tris(dibenzylideneacetone)dipalladium(0) (CAS 51364-51-3, 0.015 eq, 1.0 g), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (CAS 161265-03-8, 0.03 eq, 1.3 g), triethylamine (CAS 121-44-8, 3 eq, 22.7 g). 350 mL of deaerated anhydrous toluene were added. The reaction mixture was stirred overnight under a nitrogen atmosphere at 100 °C. After cooling to room temperature, a yellowish suspension formed. Water was then added, and the reaction mixture was neutralized to pH 7 with dilute aqueous HCl. The resulting solid precipitate was filtered, washed with cyclohexane, and the isolated crude product was recrystallized from ethyl acetate. Yield: 15.5 g (67%). Step 2 (2-(2,4-Diphenylbenzo[h]quinazolin-9-yl)-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide

[0192] A three-necked round-bottom flask was purged with nitrogen and filled with 2,4-diphenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[h]quinazoline (CAS 2248001-50-3, 1.0 eq, 17.6 g), (2-bromo-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide (1.2 eq, 14.1 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 eq, 0.9 g), and potassium carbonate (CAS 584-08-7, 2 eq, 10.5 g). A degassed mixture of 240 mL of dioxane and 40 mL of water was added. The reaction mixture was stirred overnight under a nitrogen atmosphere at 90 °C. After cooling to room temperature, a yellowish suspension formed. The solid was filtered, washed with MTBE, water, methanol, and n-hexane, and dissolved in DCM. The solution was filtered through a silica pad, and the solvent was evaporated under low pressure. The isolated crude product was dried and purified by vacuum sublimation. Yellow powder. Yield: 8.3 g (39%). (ESI-MS: 560). Supporting materials for fixture experiments

[0193] F1 is

[0194] F2 is

[0195] F3 is

[0196] F4 is

[0197] F5 is

[0198] PD2 is

[0199] LiQ is lithium 8-hydroxyquinolinolate, CAS 850918-68-2

[0200] H09 is a commercially available blue emitter host and BD200 is a commercially available blue emitter dopant, both available from SFC, Korea. Tested connections

[0201] Inventive connections:

[0202] Comparison connection: 1) Example 1: Blue fluorescent top-side emission tandem OLED

[0203] Blue fluorescent top-side emission OLEDs with a layer stack according to Table 1 were fabricated. Table 1: Schicht Material c[Vol.-%] d[nm] Anode ITO / Ag / ITO 100 / 100 / 100 10 / 120 / 10 HIL F1:PD-2 98:2 10 HTL1 F1 100 29 EBL1 F2 100 5 EML1 H09:BD200 97:3 20 ETL1 E1-E3 or C1 100 15 nCGL F3:Yb 98:2 8 pCGL F1:PD-2 99:1 10 HTL2 F1 100 45 EBL2 F2 100 5 EML2 H09:BD200 97:3 19 HBL F4 100 5 ETL2 F5:LiQ 50:50 31 EIL Yb 100 1 Kathode Ag:Mg 90:10 13 Deckschicht F1 100 75

[0204] The observed device performance is shown in Table 2. Table 2: ETL1 CIE-y Uat 10mA / cm 2 [V] Rel.V% Corr.CEFF / CIE-ybei 10mA / cm 2 [cd / A] Rel.CEFF / CIE-y % LT97 bei30mA / cm 2 / h Rel.LT97% C1 0.052 6.68 100 314.5 100 105 100 E1 0.049 6.58 99 347.8 111 121 116 E2 0.049 6.62 99 345.3 110 88 84 E3 0.049 6.70 100 358.6 114 101 97

[0205] In comparison to the prior art compound C1, the compounds E1-E3 according to the invention enable higher current efficiency.

[0206] The features disclosed in the foregoing description and in the dependent claims can, both separately and in any combination thereof, provide material for realizing the aspects of the disclosure made in various forms thereof in the independent claims.

Claims

[1] Combination of the following formula (I) where - R 1 to R 2 independent C1- to C8-hydrocarbyl, which contains at least one sp 3 -hybridized carbon atom comprising the C1- to Cs-hydrocarbyl via a sp 3 -hybridized carbon atom of C1 to C8 -hydrocarbylsan the P atom of formula (I) is bonded; - L 1 , A and L 2 are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L 1 , A and L 2 substituted or unsubstituted phenylene is and / or at least one of L 1 , A and L 2 substituted or unsubstituted naphthylene is; - whereupon, if one or more of L 1 , A and L 2substituted is / are, the one or more substituent(s) is / are independently selected from the group consisting of D, C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12 -Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl; - R 3 to R 9 are independently selected from the group consisting of H, D, C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12 -Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl. [2] Compound according to claim 1, wherein R 1 and R 2Independently selected from the group consisting of C1- to C6-alkyl, C3- to C6-cycloalkyl and C7-arylalkyl. [3] Compound according to any one of the preceding claims, wherein at least one of L 1 , A and L 2 substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with a C1 to C6 hydrocarbyl group. [4] Compound according to any of the preceding claims, wherein naphthylene is selected from the group consisting of naphthalene-1,2-diyl and naphthalene-1,5-diyl. [5] Compound according to any one of the preceding claims, wherein R 3 to R 6 and R 9 Selected independently from the group consisting of H and D; and R 7 and R 8 are independently selected from the group consisting of C1- to C6-alkyl and substituted or unsubstituted C6- to C 12 -Aryl, where, if the respective C6 - to C 12-Aryl is substituted, the one or more substituent(s) is / are independently selected from the group consisting of D and C1 to C6 alkyl. [6] Compound according to any one of the preceding claims, wherein R 3 to R 6 and R 9 Selected independently from the group consisting of H and D; and R 7 and R 8 They were independently selected from the group consisting of phenyl, biphenylyl and naphthyl. [7] Organic semiconducting material comprising the compound according to any one of the preceding claims. [8] Organic electronic device comprising a first electrode, a second electrode and an organic semiconducting layer; wherein - the organic semiconducting layer is arranged between the first electrode and the second electrode; and - the organic semiconducting layer consists of the organic semiconducting material according to claim 7. [9] Display device comprising the organic electronic device according to claim 8.

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