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

The development of organic semiconducting materials with compounds (Ia), (Ib), or E4, doped with n-type dopants, addresses inefficiencies in OLEDs by improving electron transport and stability, enhancing current efficiency and lifespan for use in high-brightness displays.

WO2026022085A1PCT designated stage Publication Date: 2026-01-29NOVALED GMBH
View PDF 13 Cites 0 Cited by

Patent Information

Application Number
PCT/EP2025/070850
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-07-26
Filing Date
2025-07-21
Publication Date
2026-01-29

AI Technical Summary

Technical Problem

Existing organic light-emitting diodes (OLEDs) face challenges in achieving balanced hole and electron injection, leading to inefficiencies in current efficiency, operating voltage, and lifetime, particularly when used in large-size flat panel displays and mobile devices, where high brightness and extended lifespan are required.

Method used

Development of an organic semiconducting material comprising compounds represented by formulas (Ia), (Ib), or E4, which can be used as electron transporting materials, potentially doped with electrical n-type dopants like lithium complexes or metals, to enhance electron mobility and stability, thereby improving the performance of OLEDs.

Benefits of technology

The proposed compounds and materials improve electron transport, reducing operating voltage, enhancing current efficiency, and extending the lifespan of OLEDs, making them suitable for high-brightness and power-efficient displays.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure EP2025070850_29012026_PF_FP_ABST
    Figure EP2025070850_29012026_PF_FP_ABST
Patent Text Reader

Abstract

The present invention relates to a compound. The present invention relates further to an organic semiconducting material comprising the compound, to an organic electronic device comprising the semiconducting material, to a display device comprising the electronic device, and to a process for preparing the organic electronic device.
Need to check novelty before this filing date? Find Prior Art

Description

[0001] Compound, organic semiconducting material, organic electronic device, and display device TECHNICAL FIELD The present invention relates to a compound. The present invention relates further to an organic semiconducting material comprising the compound, to an organic electronic device comprising the semiconducting material, to a display device comprising the electronic device, and to a process for preparing the organic electronic device. BACKGROUND OF THE INVENTION Organic semiconducting devices, such as organic light-emitting diodes OLEDs, which are self- emitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, the EML, and the ETL are thin films formed from organic compounds. When a voltage is applied to the anode and the cathode, holes injected from the anode move to the EML, via the HTL, and electrons injected from the cathode move to the EML, via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced, so that an OLED having the above-described structure has excellent efficiency and / or a long lifetime. Performance of an organic light emitting diode may be affected by characteristics of the organic semiconductor layer, and among them, may be affected by characteristics of an organic material of the organic semiconductor layer. Particularly, development of an organic semiconductor layer being capable of increasing electron mobility and simultaneously increasing electrochemical stability is needed so that the organic semiconducting device, such as an organic light emitting diode, may be applied to a large-size flat panel display. Further, development of an organic semiconductor layer being capable to have an extended life span at higher current density and thereby at higher brightness is needed. In particular, the development of an organic semiconductor material or semiconductor layer is needed with respect to lowering the operating voltage, which is important for reducing power consumption and increasing battery life, for example of a mobile display device. DE 10 2021 100 597 A1 discloses a plurality of host materials and an organic electroluminescent device comprising the same. DE 102022102199 A1 an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. US 2021 / 0098716 A1 discloses an organic electroluminescence device, comprising: a first electrode; a second electrode on the first electrode; and an emission layer between the first electrode and the second electrode, wherein the emission layer comprises host compounds and dopant compounds. US 2022 / 0069235 A1 discloses a light-emitting device comprising: a first electrode; a second electrode; and an interlayer between the first electrode and the second electrode and comprising an emission layer, wherein the interlayer further comprises a hole transport region between the first electrode and the emission layer, the hole transport region comprises a first auxiliary layer and a second auxiliary layer between the first electrode and the first auxiliary layer, the first auxiliary layer comprises a first compound, the second auxiliary layer comprises a second compound, the first compound and the second compound are different from each other, and a lowest excitation triplet energy level (T1) of the first compound is equal to or greater than about 1.60 eV and less than or equal to about 1.80 eV. It is, therefore, the object of the present invention to provide compounds and semiconducting materials for preparing organic electronic devices, such as organic light emitting diodes and display devices overcoming drawbacks of the prior art, in particular with respect to current efficiency and / or operating voltage and / or lifetime and / or operating voltage stability. DISCLOSURE This object is achieved by an organic semiconducting material comprising a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl; - R7is selected from the group consisting of C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl, wherein the C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl comprise only six-membered aromatic rings. This object is further achieved by an organic electronic device comprising the organic semiconducting material according to the present invention. This object is further achieved by a display device comprising at least one organic electronic device according to the present invention. This object is further achieved by a compound represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6to C30aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is a C6to C60aryl or a C3to C59heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings. Organic semiconducting material According to a further aspect, the invention is related to an organic semiconducting material. The organic semiconducting material comprises the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the invention as described herein. This includes the possibility that the organic semiconducting material comprises a mixture of two or more of the compound of formula (Ia), the compound of formula (Ib) and the compound E4. Whenever herein, reference is made to “the compound of formula (Ia), the compound of formula (Ib) or the compound E4” mixture of two or more of the compound of formula (Ia), the compound of formula (Ib) and the compound E4 are included. The organic semiconducting material may be an electron transporting material. The organic semiconducting material may comprise the compound of formula (Ia), the compound of formula (Ib) or the compound E4 in an amount of at least 50 wt.-% with respect to the total weight of the organic semiconducting material, or in higher amounts, such as e.g. at least 60 wt.-%, at least 70 wt.-%, at least 80 wt.-%, at least 90 wt.-%, at least 95 wt.-% or at least 98 wt.-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may consist of the compound of formula (Ia), the compound of formula (Ib) or the compound E4. The organic semiconducting material may comprise besides the compound of formula (Ia), the compound of formula (Ib) or the compound E4 an electrical dopant, especially an electrical n- dopant. Under electrical dopant, especially n-type dopant, it is understood a compound which, if embedded into an electron transport matrix, improves, in comparison with the neat matrix under the same physical conditions, the electron properties of the formed organic material, particularly in terms of electron injection and / or electron conductivity. In the context of the present invention “embedded into an electron transport matrix” means homogenously mixed with the electron transport matrix. The electrical dopant as referred to herein is especially selected from elemental metals, metal salts, metal complexes and organic radicals. In one embodiment, the electrical dopant is selected from alkali metal salts and alkali metal complexes; preferably from lithium salts and lithium organic complexes; more preferably from lithium halides and lithium organic chelates; even more preferably from lithium fluoride, a lithium quinolinolate, lithium borate, lithium phenolate, lithium pyridinolate or from a lithium complex with a Schiff base ligand; most preferably, - the lithium complex has the formula II, III or IV: wherein A1to A6are same or independently selected from CH, CR, N, O; R is same or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl with 1 to 20 carbon atoms; and more preferred A1to A6are CH, - the borate based organic ligand is a tetra(1H-pyrazol-1-yl)borate, - the phenolate is a 2-(pyridin-2-yl)phenolate, a 2-(diphenylphosphoryl)phenolate, an imidazol phenolate, 2-(pyridin-2-yl)phenolate or 2-(1-phenyl-1H-benzo[d]imidazol-2- yl)phenolate, - the pyridinolate is a 2-(diphenylphosphoryl)pyridin-3-olate,- the lithium Schiff base has the structure 100, 101, 102 or 103:

[0002] According to one embodiment of the invention, the electron transport layer of the present invention comprises a lithium organic complex, especially may comprise 8- hydroxyquinolinolato-lithium (= LiQ). Electrically neutral metal complexes suitable as n-type dopants may be e.g. strongly reductive complexes of some transition metals in low oxidation state. Particularly strong n-type dopants may 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. Electrically neutral organic radicals suitable as n-type dopants may be e.g. organic radicals created by supply of additional energy from their stable dimers, oligomers or polymers, as described in more detail in EP 1837926 B1, WO2007 / 107306, or WO2007 / 107356. Under an elemental metal, it is understood a metal in a state of a neat metal, of a metal alloy, or in a state of free atoms or metal clusters. It is understood that metals deposited by vacuum thermal evaporation from a metallic phase, e.g. from a neat bulk metal, vaporize in their elemental form. It is further understood that if the vaporized 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 prepared by vacuum thermal evaporation contains the metal at least partially in its elemental form. Compound of formula (Ia), compound of formula (Ib) and compound E4 in the organic semiconducting material The organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4. The compound of formulas (Ia), (Ib) and E4 may be unsubstituted or substituted. If the compound of formulas (Ia), (Ib) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C1 to C6 alkyl may be attached to the structure by formally replacing a terminal hydrogen atom. Preferably, if the compound of formulas (Ia), (Ib) and E4 is substituted, the compound may be substituted with one or more D (deuterium). Most preferred, the compound of formulas (Ia), (Ib) and E4 is unsubstituted. According to an embodiment, the compound of formula (Ib) is unsubstituted. According to an embodiment, the compound of formula (Ib) is unsubstituted, and the compound of formulas (Ia) and E4 may be unsubstituted or substituted. If the compound of formulas (Ia) and E4 are substituted, the one or more substituents are independently selected from the group consisting of D and C1 to C6 alkyl, wherein “substituted” means that the respective substituent is attached to the structure by formally replacing a terminal hydrogen atom. Preferably, if the compound of formulas (Ia) and E4 is substituted, the compound may be substituted with one or more D (deuterium). Most preferred, the compound of formulas (Ia) and E4 is unsubstituted. According to embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ib) is unsubstituted. According to embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl; - R7is selected from the group consisting of C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl, wherein the C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ia), (Ib), and E4 is unsubstituted. In accordance with the present disclosure, in a formula showing the following binding situation, the arbitrary group A may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond. In formula (Ia), m is an integer selected from the group consisting of 0, 1, 2, 3, and 4. In formula (Ia), m may be an integer selected from the group consisting of 0, 1, 2, and 3. In formula (Ia), m may be an integer selected from the group consisting of 0, 1, and 2. In formula (Ia), m may be an integer selected from the group consisting of 1 and 2. In formula (Ia), m may be an integer selected from the group consisting of 0 and 1. In formula (Ia), m may be 1. If m is 0, a single bond is formed at the respective position, that is, the compound of formula (Ia) has the following structure . In formulas (Ia) and (Ib), n, p, and q are independently integers selected from the group consisting of 1, 2, 3 and 4. In formulas (Ia) and (Ib), n, p, and q may be independently integers selected from the group consisting of 1, 2, and 3. In formulas (Ia) and (Ib), n, p, and q may be independently integers selected from the group consisting of 1 and 2. If m, n, p or q is 1, the respective one phenylene is independently ortho-phenylene, meta- phenylene or para-phenylene, preferably independently meta-phenylene or para-phenylene. For example, if m = 1 and the respective phenylene is para-phenylene, the compound of formula (Ia) has the following structure If m, n, p or q is 2, the respective biphenyl-diyl may be selected from wherein *1 and *2 are the binding positions to the remaining parts of the respective structure. Preferably, if m, n, p or q is 2, the respective biphenyl-diyl is the respective biphenyl-diyl is to form the following structure (in which, as an example, p is 2) In formulas (Ia) and (Ib), Ar1to Ar9are independently selected from C6 to C30 aryl. Ar1to Ar9may be independently selected from C6 to C24 aryl. Ar1to Ar9may be independently selected from C6 to C18 aryl. Ar1to Ar9may be independently selected from C6 to C12 aryl. Ar1to Ar9may be independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl. Ar1to Ar9may be each phenyl. R2to R6are independently selected from the group consisting of H, D and C6to C18aryl. R2to R6may be independently selected from the group consisting of H, D and C6to C12aryl. R2to R6may be independently selected from the group consisting of H, D, phenyl, biphenyl-yl, and naphthyl. R2to R6may be independently selected from the group consisting of H, D, and phenyl. R2is C6to C18aryl; and / or R2and R3are independently C6to C18aryl; and / or R3and R4are independently C6to C18aryl; and / or R4and R5are independently C6to C18aryl; and / or R5and R6are independently C6to C18aryl; and R6is C6to C18aryl. It may be provided that R2is phenyl; and / or R2and R3are both phenyl; and / or R3and R4are both phenyl; and / or R4and R5are both phenyl; and / or R5and R6are both phenyl; and R6is phenyl. In other words, it is provided that two of R2to R6are C6to C18aryl, preferably phenyl, and adjacent to each other and / or one or both of R2to R6which are adjacent to the binding position is / are C6to C18aryl, preferably phenyl. The moiety in which * represents the binding position to may be selected from the following structures In formula (Ia), R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl. R1may be selected from the group consisting of C6 to C54 aryl and C3 to C53 heteroaryl. R1may be selected from the group consisting of C6 to C48 aryl and C3 to C47 heteroaryl. R1may be selected from the group consisting of C6 to C42 aryl and C3 to C41 heteroaryl. R1may be selected from the group consisting of C6 to C36 aryl and C3 to C35 heteroaryl. R1may be selected from the group consisting of C6 to C30 aryl and C3 to C29 heteroaryl. R1may be selected from the group consisting of C6 to C24 aryl and C3 to C23 heteroaryl. R1may be selected from the group consisting of C6 to C18 aryl and C3 to C17 heteroaryl. R1may be selected from the group consisting of C6 to C12 aryl and C3 to C11 heteroaryl. In formula (Ia), R1is selected from the group consisting of C6 to C60 aryl. R1may be selected from C6 to C54 aryl. R1may be selected from C6 to C48 aryl. R1may be selected from C6 to C42 aryl. R1may be selected from C6 to C36 aryl. R1may be selected from C6 to C30 aryl. R1may be selected from C6 to C24 aryl. R1may be selected from C6 to C18 aryl. R1may be selected from C6 to C12 aryl. R1may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl. R1may be phenyl. In formula (Ia), R1may be selected from the group C6 to C60 aryl and C3 to C59 heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six- membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2. R1may be aryl or heteroaryl consisting of only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2. In formula (Ia), R1may be selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C54aryl and C3to C53heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C48aryl and C3to C47heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C42aryl and C3to C41heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C36aryl and C3to C35heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C30aryl and C3to C29heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C24aryl and C3to C23heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C18aryl and C3to C17heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6to C12aryl and C3to C11heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. In each case, for the respective aryl or heteroaryl comprising only six-membered aromatic rings, the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2, respectively matching with the number of carbon atoms in the different embodiments. R1may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl. R1may be phenyl. According to an embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl, wherein the C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl comprise only six-membered aromatic rings. According to an embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ib) is unsubstituted. According to an embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl, wherein the C10 to C30 condensed aryl and C5 to C29 condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ia), (Ib), and E4 is unsubstituted. In formula (Ib), R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl, respectively the C5to C29condensed heteroaryl comprise only six-membered aromatic rings. Examples of a respective C10to C30condensed aryl are naphthyl or phenathryl. Examples of respective C5to C29condensed heteroaryl are quinolinyl or acridinyl. An example of a condensed heteroaryl not encompassed by the definition of R7is dibenzofuranyl which is, on the one hand, a condensed heteroaryl but does not only comprise six-memberd rings because it comprises also a five membered ring bearing the oxygen atom. R7may be selected from the group consisting of C10to C24condensed aryl and C5to C23condensed heteroaryl, wherein the C10to C24condensed aryl, respectively the C5to C23condensed heteroaryl comprise only six-membered aromatic rings. R7may be selected from the group consisting of C10to C18condensed aryl and C5to C17condensed heteroaryl, wherein the C10to C18condensed aryl, respectively the C5to C17condensed heteroaryl comprise only six- membered aromatic rings. R7may be C10to C24condensed aryl, wherein the C10to C24condensed aryl comprises only six- membered aromatic rings. R7may be C10to C18condensed aryl, wherein the C10to C18condensed aryl comprises only six-membered aromatic rings. R7may be selected from the group consisting of naphthyl and phenanthryl. R7may be selected from the group consisting of 1-naphthyl and 2-naphthyl. R7may be 2-naphthyl. The compound of formula (Ia) may by E2 or E3 The compound of formula (Ib) may be E1 According to one embodiment, there is provided an organic semiconducting material comprising a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is 0 or 1; - n, p, and q are independently integers selected as 1 or 2; - Ar1to Ar9are independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl; - R2to R6are independently selected from the group consisting of H, D, and phenyl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; - R6is C6 to C18 aryl; - R1is selected from the group consisting of phenyl, biphenyl-yl and naphthyl; - R7is selected from the group consisting of naphthyl and phenanthryl. According to an embodiment, the following compounds are excluded

[0003] , , According to an embodiment, the organic semiconducting material does not comprise the5 following compounds

[0004] According to an embodiment, the following compounds are excluded as a compound represented by formulas (Ia), Ib) or E4 in the organic semiconducting material according to the present invention

[0005] An organic semiconducting material comprising a compound represented by one of the5 following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the following compounds are excluded According to embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ib) is unsubstituted; and wherein the following compounds are excluded According to embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ia), (Ib), and E4 is unsubstituted; and wherein the following compounds are excluded According to an embodiment, the organic semiconducting material comprises a compound5 represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the following compounds are excluded According to an embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ib) is unsubstituted; and wherein the following compounds are excluded According to an embodiment, the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; and wherein the compound of formula (Ia), (Ib), and E4 is unsubstituted; and wherein the following compounds are excluded Organic electronic device According to one aspect, the invention is related 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, comprises or consists of the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention. The organic electronic device may be an organic light emitting diode (OLED). The organic light emitting diode may comprise an anode, a cathode, a first light emitting layer and a semiconducting layer wherein - the first light emitting layer is arranged 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. The semiconducting layer may consist of the organic semiconducting material according to the present invention. The organic light emitting diode may comprise two or more semiconducting layers comprising a semiconducting material in accordance with the invention, respectively. The semiconducting layer may be an electron injection layer, an electron transport layer, a hole blocking layer, or a n-type charge generation layer. The semiconducting layer may be an electron transport layer. The semiconducting layer may be an electron transport layer and OLED may further comprise an electron injection layer and the electron transport layer may be arranged between the first light emitting layer and the electron injection layer. The semiconducting layer may be an electron transport layer and OLED may further comprise a hole blocking layer and the electron transport layer may be arranged between the hole blocking layer and the cathode. The semiconducting layer may be an electron transport layer and OLED may further comprise an electron injection layer and a hole blocking layer; and the electron transport layer may be contacting sandwiched between the electron injection layer and the hole blocking layer. The organic electronic device, especially the organic light emitting diode in accordance with the invention may comprise especially, besides the semiconducting layer comprising or consisting of the semiconducting material according to the invention, further layers. Exemplary embodiments of respective layers are described in the following: Substrate The substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate may be both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate or a silicon substrate. Anode electrode Either a first electrode or a second electrode comprised in the inventive organic electronic device may be an anode electrode. The anode electrode may be formed by depositing or sputtering a material that is used to form the anode electrode. The material used to form the anode electrode may be a high work-function material, so as to facilitate hole injection. The anode material may also be selected from a low work function material (i.e. aluminum). The anode electrode may 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), may be used to form the anode electrode. The anode electrode may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys. Hole injection layer A hole injection layer (HIL) may be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like. When the HIL is formed using vacuum deposition, the deposition conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 500° C, a pressure of 10-8to 10-3Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm / sec. When the HIL is formed using spin coating or printing, coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C. Thermal treatment removes a solvent after the coating is performed. The HIL may be formed of any compound that is commonly used to form a HIL. Examples of compounds that may 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 / camphor sulfonic acid (Pani / CSA), and polyaniline) / poly(4-styrenesulfonate (PANI / PSS). The HIL may comprise or consist of p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalen-2,6- diylidene) dimalononitrile or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyl)acetonitrile) but not limited hereto. The HIL may be selected from a hole-transporting matrix compound doped with a p-type dopant. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc), which HOMO level is approximately -5.2 eV, doped with tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), which LUMO level is about -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'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile. The p- type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%. The thickness of the HIL may be in the range from about 1 nm to about 100 nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage. Hole transport layer A hole transport layer (HTL) may be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL. The HTL may be formed of any compound that is commonly used to form a HTL. Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953−1010 and incorporated by reference. Examples of the compound that may 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'-diphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit excitons from being diffused into the EML. The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably, about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. A preferred thickness of the HTL may be 170 nm to 200 nm. When the thickness of the HTL is within this range, the HTL may have excellent hole transporting characteristics, without a substantial penalty in driving voltage. Electron blocking layer The function of an electron blocking layer (EBL) is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and / or lifetime are improved. Typically, the electron blocking layer comprises a triarylamine compound. The triarylamine compound may have a LUMO level closer to vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO level of the hole transport layer. The thickness of the electron blocking layer may be selected between 2 and 20 nm. If the electron blocking layer has a high triplet level, it may also be described as triplet control layer. The function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used. Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved. The triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emitter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2722908 A1. Photoactive layer (PAL) The photoactive layer converts an electrical current into photons or photons into an electrical current. The PAL may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like. When the PAL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the PAL. It may be provided that the photoactive layer does not comprise the compound of formula (Ia), the compound of formula (Ib) or the compound E4. The photoactive layer may be a light-emitting layer or a light-absorbing layer. Emission layer (EML) The EML may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. The respective emission layer (EML) may be formed of a combination of a host and an emitter dopant. The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters which emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer. The amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight of the host. Alternatively, the emission layer may consist of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage. Hole blocking layer (HBL) A hole blocking layer (HBL) may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL. When the EML comprises a phosphorescent dopant, the HBL may have also a triplet exciton blocking function. The HBL may also be named auxiliary ETL or a-ETL. When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. The HBL may have a thickness in the range from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in driving voltage. The hole blocking layer may be made of the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic light emitting diode according to the invention. Electron transport layer (ETL) The organic electronic device according to the present invention may comprise an electron transport layer (ETL). According to various embodiments the OLED may comprise an electron transport layer or an electron transport layer stack comprising at least a first electron transport layer and at least a second electron transport layer. By suitably adjusting energy levels of particular layers of the ETL, the injection and transport of the electrons may be controlled, and the holes may be efficiently blocked. Thus, the OLED may have long lifetime. The electron transport layer may comprise ETM materials comprising one or more electron transport compound(s) known in the art. According to an 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 C1to C4alkyl. In this regard, an aromatic, respectively 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 condensed (hetero)aromatic rings, each ring is considered as a single ring in this regard. For example, naphthalene comprises two aromatic rings. The electron transport compound may 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. The aromatic or heteroaromatic rings of the electron transport compound may be 6-membered rings. The heteroaromatic rings of the electron transport compound may be a N-containing heteroaromatic ring, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, optionally all of the heteroaromatic rings heteroaromatic rings contain N as the only type of heteroatom. The electron transport compound may comprise at least one six-member 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, respectively. The at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be an azine. The at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be triazine, diazine, pyrazine, pyrimidine, pyridine, quinazoline or bonzoquinazoline, preferably triazine. 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 which is free of a heteroatom. In an 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. Further, the electron transport layer may comprise one or more additives. The additive may be an n-type dopant. The additive can be alkali metal, alkali metal compound, alkaline earth metal, alkaline earth metal compound, transition metal, transition metal compound or a rare earth metal. In another embodiment, the metal can be one selected from a group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In another emdodiment, the n-type dopant can be one selected from a group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb. In an embodiment the alkali metal compound may be 8-Hydroxyquinolinolato-lithium (LiQ), Lithium tetra(1H-pyrazol-1-yl)borate or Lithium 2-(diphenylphosphoryl)phenolate. Suitable compounds for the ETM (which may be used in addition to the inventive compound as defined above) are not particularly limited. In one embodiment, the electron transport matrix compounds consist of covalently bound atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably of at least 10 delocalized electrons. In one embodiment, the conjugated system of delocalized electrons may be comprised in aromatic or heteroaromatic structural moieties, as disclosed e.g. in documents EP 1970371 A1 or WO 2013 / 079217 A1. The electron transport layer may have a thickness from about 1 to about 100 nm, such as from about 10 to about 50 nm. The electron transport layer may comprise or consist of the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic electronic device according to the invention. Electron injection layer (EIL) The optional EIL, which may facilitate injection of electrons from the cathode, may be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg, especially Yb which are known in the art. Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL. The thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage. The electron injection layer may comprise the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic electronic device according to the invention. Cathode electrode The cathode electrode is formed on the EIL if present. The cathode electrode may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may be formed 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 the like. Alternatively, the cathode electrode may be formed of a transparent conductive oxide, such as ITO or IZO. The cathode may comprise more that 50 volume % of metal selected from Ag and Au. The thickness of the cathode electrode may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range from about 5 nm to about 50 nm, the cathode electrode may be transparent or semitransparent even if formed from a metal or metal alloy. The cathode may be a semi-transparent metal cathode having a thickness less than 20 nm, preferably less than 15 nm. It is to be understood that the cathode electrode is not part of an electron injection layer or the electron transport layer. Charge generation layer / hole generation layer The organic electronic device according to the present invention may comprise a charge generation layer. The charge generation layer (CGL) is composed of a double layer. The charge generation layer is a pn junction joining an n-type charge generation layer (electron generation layer) and a p-type charge generation layer (hole generation layer). The n-side of the pn junction generates electrons and injects them into the layer which is adjacent in the direction to the anode. Analogously, the p-side of the p-n junction generates holes and injects them into the layer which is adjacent in the direction to the cathode. Charge generation layers are used in tandem devices, for example, in tandem OLEDs comprising, between two electrodes, two or more emission layers. In a tandem OLED comprising two emission layers, the n-type charge generation layer provides electrons for the first light emission layer arranged near the anode, while the p-type charge generation layer provides holes to the second light emission layer arranged between the first emission layer and the cathode. The hole generation layer (p-type charge generation layer) can be composed of an organic matrix material doped with p-type dopant. Suitable matrix materials for the hole generation layer may be materials conventionally used as hole injection and / or hole transport matrix materials. Also, p-type dopant used for the hole generation layer can employ conventional materials. For example, the p-type dopant can be one selected from a group consisting of tetrafluore-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radialene derivatives, iodine, FeCl3, FeF3, and SbCl5. Also, the host can be one selected from a group consisting of N,N'-di(naphthalen-1-yl)-N,N-diphenyl- benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD) and N,N',N'-tetranaphthyl-benzidine (TNB). The n-type charge generation layer can be layer of a neat n-dopant, for example of an electropositive metal, or can consist of an organic matrix material doped with the n-dopant. In one embodiment, the n-type dopant can be alkali metal, alkali metal compound, alkaline earth metal, or alkaline earth metal compound. In another embodiment, the metal can be one selected from a group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant can be one selected from a group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb. Suitable matrix materials for the electron generating layer may be the materials conventionally used as matrix materials for electron injection or electron transport layers. The matrix material can be for example one selected from a group consisting of triazine compounds, hydroxyquinoline derivatives like tris(8-hydroxyquinoline)aluminum, benzazole derivatives, and silole derivatives. The n-type charge generation layer may comprise the semiconducting material according to the invention, that is, may be the semiconducting layer in the organic light emitting diode according to the invention. According to one aspect, the OLED according to the present invention can comprise a layer structure of a substrate that is adjacent arranged to an anode electrode, the anode electrode is adjacent arranged to a first hole injection layer, the first hole injection layer is adjacent arranged to a first hole transport layer, the first hole transport layer is adjacent arranged to a first electron blocking layer, the first electron blocking layer is adjacent arranged to a first emission layer, the first emission layer is adjacent arranged to an electron blocking layer, the electron blocking layer is adjacent arranged to an electron transport layer, the electron transport layer is adjacent arranged to an electron injection layer, the electron injection layer is adjacent arranged to a cathode, wherein the electron transport layer consists of the organic semiconducting material according to the present invention. According to one aspect, the OLED according to the present invention can comprise a layer structure of a substrate that is adjacent arranged to an anode electrode, the anode electrode is adjacent arranged to a first hole injection layer, the first hole injection layer is adjacent arranged to a first hole transport layer, the first hole transport layer is adjacent arranged to a first electron blocking layer, the first electron blocking layer is adjacent arranged to a first emission layer, the first emission layer is adjacent arranged to a first electron transport layer, the first electron transport layer is adjacent arranged to an n-type charge generation layer (n- type sub-layer), the n-type charge generation layer is adjacent arranged to a hole generating layer (p-type sub-layer), an interlayer may be provided between the n-type sub-layer, and the p-type sub-layer, the hole generating layer is adjacent arranged to a second hole transport layer, the second hole transport layer is adjacent arranged to a second electron blocking layer, the second electron blocking layer is adjacent arranged to a second emission layer, between the second emission layer and the cathode electrode an electron transport layer and / or an electron injection layer are arranged, wherein the electron transport layer consists of the organic semiconducting material according to the present invention. Display device According to a further aspect, the invention is related to a display device comprising the organic light emitting diode according to the invention. The display device may be a television, a tablet, or a mobile phone. Process for preparing the organic light emitting diode According to a further aspect, the invention is related to a process for preparing the organic electronic device according to the present invention, wherein the process comprises a step of depositing compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention on a solid support. The method for depositing may comprise:- deposition via vacuum thermal evaporation;- deposition via solution processing, preferably the processing is selected from spin-coating, printing, casting; and / or- slot-die coating. Compound of formula (IIa), compound of formula and compound E4 According to a further aspect, the invention relates a compound represented by one of the following formulas (IIa), (IIb) or E4. The compound of formulas (IIa), (IIb) and E4 may be unsubstituted or substituted. If the compound of formulas (IIa), (IIb) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C1to C6alkyl may be attached to the structure by formally replacing a terminal hydrogen atom. Preferably, if the compound of formulas (IIa), (IIb) and E4 is substituted, the compound may be substituted with one or more D (deuterium). Most preferred, the compound of formulas (IIa), (IIb) and E4 is unsubstituted. According to an embodiment, the compound of formula (IIb) is unsubstituted. According to an embodiment, the compound of formula (IIb) is unsubstituted, and the compound of formulas (IIa) and E4 may be unsubstituted or substituted. If the compound of formulas (IIa) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C1to C6alkyl may be attached to the structure by formally replacing a terminal hydrogen atom. Preferably, if the compound of formulas (IIa) and E4 is substituted, the compound may be substituted with one or more D (deuterium). Most preferred, the compound of formulas ((IIa) and E4 is unsubstituted. According to an embodiment, the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6to C30aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is a C6to C60aryl or a C3to C59heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; wherein the compound of formula (IIb) is unsubstituted. According to an embodiment, the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl; - R1is a C6 to C60 aryl or a C3 to C59 heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; wherein the compound of formulas (IIa), (IIb), and E4 is unsubstituted. In accordance with the present disclosure, in a formula showing the following binding situation, the arbitrary group A may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond. In formula (IIa), m is an integer selected from the group consisting of 0, 1, 2, 3, and 4. In formula (IIa), m may be an integer selected from the group consisting of 0, 1, 2, and 3. In formula (IIa), m may be an integer selected from the group consisting of 0, 1, and 2. In formula (IIa), m may be an integer selected from the group consisting of 1 and 2. In formula (IIa), m may be an integer selected from the group consisting of 0 and 1. In formula (IIa), m may be 1. If m is 0, a single bond is formed at the respective position, that is, the compound of formula (IIa) has the following structure . In formulas (IIa) and (IIb), n, p, and q are independently integers selected from the group consisting of 1, 2, 3 and 4. In formulas (IIa) and (IIb), n, p, and q may be independently integers selected from the group consisting of 1, 2, and 3. In formulas (IIa) and (IIb), n, p, and q may be independently integers selected from the group consisting of 1 and 2. If m, n, p or q is 1, the respective one phenylene is independently ortho-phenylene, meta- phenylene or para-phenylene, preferably independently meta-phenylene or para-phenylene. For example, if m = 1 and the respective phenylene is para-phenylene, the compound of formula (IIa) has the following structure If m, n, p or q is 2, the respective biphenyl-diyl may be selected from wherein *1 and *2 are the binding positions to the remaining parts of the respective structure. Preferably, if m, n, p or q is 2, the respective biphenyl-diyl is the respective biphenyl-diyl is to form the following structure (in which, as an example, p is 2) In formulas (IIa) and (IIb), Ar1to Ar9are independently selected from C6to C30aryl. Ar1to Ar9may be independently selected from C6to C24aryl. Ar1to Ar9may be independently selected from C6to C18aryl. Ar1to Ar9may be independently selected from C6to C12aryl. Ar1to Ar9may be independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl. Ar1to Ar9may be each phenyl. R2to R6are independently selected from the group consisting of H, D and C6to C18aryl. R2to R6may be independently selected from the group consisting of H, D and C6to C12aryl. R2to R6may be independently selected from the group consisting of H, D, phenyl, biphenyl-yl, and naphthyl. R2to R6may be independently selected from the group consisting of H, D, and phenyl. R2is C6to C18aryl; and / or R2and R3are independently C6to C18aryl; and / or R3and R4are independently C6to C18aryl; and / or R4and R5are independently C6to C18aryl; and / or R5and R6are independently C6to C18aryl; and R6is C6to C18aryl. It may be provided that R2is phenyl; and / or R2and R3are both phenyl; and / or R3and R4are both phenyl; and / or R4and R5are both phenyl; and / or R5and R6are both phenyl; and R6is phenyl. In other words, it is provided that two of R2to R6are C6to C18aryl, preferably phenyl, and adjacent to each other and / or one or both of R2to R6which are adjacent to the binding position is / are C6to C18aryl, preferably phenyl. The moiety in which * represents the binding position to may be selected from the following structures In formula (IIa), R1is aryl or heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2. R1may be aryl or heteroaryl consisting of only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2. In formula (IIa), R1is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C54 aryl and C3 to C53 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C48 aryl and C3 to C47 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C42 aryl and C3 to C41 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C36 aryl and C3 to C35 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C30 aryl and C3 to C29 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C24 aryl and C3 to C23 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C18 aryl and C3 to C17 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. R1may be selected from the group consisting of C6 to C12 aryl and C3 to C11 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings. In each case, for the respective aryl or heteroaryl comprising only six-membered aromatic rings, the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2, respectively matching with the number of carbon atoms in the different embodiments. R1may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl. R1may be phenyl. In formula (IIb), R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl, respectively the C5to C29condensed heteroaryl comprise only six-membered aromatic rings. Examples of a respective C10to C30condensed aryl are naphthyl or phenythryl. Examples of respective C5to C29condensed heteroaryl are quinolinyl or acridinyl. An example of a condensed heteroaryl not encompassed by the definition of R7is dibenzofuranyl which is, on the one hand, a condensed heteroaryl but does not only comprise six-memeberd rings but also a five membered ring bearing the oxygen atom. R7may be selected from the group consisting of C10to C24condensed aryl and C5to C23condensed heteroaryl, wherein the C10to C24condensed aryl, respectively the C5to C23condensed heteroaryl comprise only six-membered aromatic rings. R7may be selected from the group consisting of C10to C18condensed aryl and C5to C17condensed heteroaryl, wherein the C10to C18condensed aryl, respectively the C5to C17condensed heteroaryl comprise only six- membered aromatic rings. R7may be C10to C24condensed aryl, wherein the C10to C24condensed aryl comprises only six- membered aromatic rings. R7may be C10to C18condensed aryl, wherein the C10to C18condensed aryl comprises only six-membered aromatic rings. R7may be selected from the group consisting of naphthyl and phenanthryl. R7may be selected from the group consisting of 1-naphthyl and 2-naphthyl. R7may be 2-naphthyl. According to one embodiment, there is provided a compound represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is 0 or 1; - n, p, and q are independently integers selected as 1 or 2; - Ar1to Ar9are independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl; - R2to R6are independently selected from the group consisting of H, D, and phenyl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; - R6is C6 to C18 aryl; - R1is selected from the group consisting of phenyl, biphenyl-yl and naphthyl; - R7is selected from the group consisting of naphthyl and phenanthryl. The compound of formula (IIa) may by E2 or E3 The compound of formula (IIb) may be E1 According to an embodiment, the following compounds are excluded from the compound According to an embodiment, the following compounds are excluded from the compound comprising a compound represented by formulas (IIa), (IIb) or E4

[0006] According to an embodiment, the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6to C30aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is a C6to C60aryl or a C3to C59heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; wherein the compound of formula (IIb) is unsubstituted; and wherein the following compounds are excluded According to an embodiment, the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6to C30aryl; - R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is a C6to C60aryl or a C3to C59heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings; wherein the compound of formulas (IIa), (IIb), and E4 is unsubstituted; and wherein the following compounds are excluded Details and definitions of the invention An organic compound as referred to herein is generally any chemical compound that contains carbon (except some compounds generally referred to as being inorganic, such as carbonates, cyanides, carbon dioxide, diamond etc.). The term organic compound used herein also encompasses compounds such as organometallic compounds, for example metallocenes etc. If not mentioned else explicitly, all compounds, groups, moieties, substituents etc. shown herein, especially by structural formulas, by systematic names etc. encompass the respective partially and fully deuteriated derivatives thereof. The term “zero-valent” as used herein refers to a metal in the oxidation state 0, i.e. particular to metals from which no electron has been removed. The zero-valent metal may be present in the form of zero-valent atoms, neat metal, alloys etc. The term “trivalent” as used herein refers to a nitrogen atom with a single bond and a double bond and containing a lone pair of electrons. The term “hydrocarbyl group” as used herein shall be understood to encompass any organic group comprising carbon atoms, in particular organic groups, such as alkyl, aryl, heteroaryl, heteroalkyl, in particular such groups which are substituents usual in organic electronics. The term “conjugated system” as used herein refer to a system of alternating π- and σ-bonds or a molecule having alternating single and multiple bonds i.e. double bond or a system having one or more two-atom structural units having the π-bond between its atoms can be replaced by an atom bearing at least one lone electron pair, typically by a divalent O or S atom. The term “alkyl” as used herein shall encompass linear as well as branched and cyclic alkyl. For example, C3-alkyl may be selected from n-propyl and iso-propyl. Likewise, C4-alkyl encompasses n-butyl, sec-butyl and t-butyl. Likewise, C6-alkyl encompasses n-hexyl and cyclo- hexyl. The subscribed number n in Cnrelates to the total number of carbon atoms in the respective alkyl, arylene, heteroarylene or aryl group. The term “aryl” or “arylene” as used herein shall encompass phenyl (C6-aryl), fused aromatics, such as naphthalene, anthracene, phenanthrene, tetracene etc.. Further encompassed are biphenyl and oligo- or polyphenyls, such as terphenyl, phenyl-substituted biphenyl, phenyl- substituted terphenyl (such as tetraphenyl benzene groups) etc.. “Arylene” respectively “heteroarylene”, refers to groups to which two further moieties are attached. In the present specification, the term “aryl group” or “arylene group” may refer to a group comprising at least one hydrocarbon aromatic moiety, and all the elements of the hydrocarbon aromatic moiety may have p-orbitals which form conjugation, for example a phenyl group, a napthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group and the like. Further encompassed are spiro compounds in which two aromatic moieties are connected with each other via a spiro-atom, such as 9,9’-spirobi[9H-fluorene]yl. The aryl or arylene group may include a monocyclic or fused ring polycyclic (i.e., links sharing adjacent pairs of carbon atoms) functional group. 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” may refer to aromatic heterocycles with at least one heteroatom, and all the elements of the hydrocarbon heteroaromatic moiety may have p-orbitals which form conjugation. The heteroatom may be selected from N, O, S, B, Si, P, Se, preferably from N, O and S. A heteroarylene ring may comprise at least 1 to 3 heteroatoms. Preferably, a heteroarylene ring may comprise at least 1 to 3 heteroatoms individually selected from N, S and / or O. Just as in case of “aryl” / ”arylene”, the term “heteroaryl” comprises, for example, spiro compounds in which two aromatic moieties are connected with each other, such as spiro[fluorene-9,9’-xanthene]. Further exemplary heteroaryl groups are diazine, triazine, dibenzofurane, dibenzothiofurane, acridine, benzoacridine, dibenzoacridine etc. The subscripted number n in Cn-heteroaryl merely refers to the number of carbon atoms excluding the number of heteroatoms. In this context, it is clear that a C3heteroarylene group is an aromatic compound comprising three carbon atoms, such as pyrazole, imidazole, oxazole, thiazole and the like. The term “halogenated” refers to an organic compound in which one hydrogen atom thereof is replaced by a halogen atom. The term “perhalogenated” refers to an organic compound in which all of the hydrogen atoms thereof are replaced by halogen atoms. The meaning of the terms “fluorinated” and “perfluorinated” should be understood analogously. The term “alkenyl” as used herein refers to a group -CR1= CR2R3comprising a carbon-carbon double bond. The term “alkoxy” as used herein refers to a structural fragment of the Formula –OR with R being hydrocarbyl, preferably alkyl or cycloalkyl. The term “thioalkyl” as used herein refers to a structural fragment of the Formula –SR with R being hydrocarbyl, preferably alkyl or cycloalkyl. In the present specification, the term single bond refers to a direct bond and vice versa. In terms of the invention, a group is “substituted with” another group if one of the hydrogen atoms comprised in this group is replaced by another group, wherein the other group is the substituent. In accordance with the present disclosure, in a formula showing the following binding situation, the arbitrary group A may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond. In terms of the invention, the expression “between” with respect to one layer being between two other layers does not exclude the presence of further layers, which may be arranged between the one layer and one of the two other layers. In terms of the invention, the expression “in direct contact” with respect to two layers being in direct contact with each other means that no further layer is arranged between those two layers. One layer deposited on the top of another layer is deemed to be in direct contact with this layer. In the context of the present specification the term “essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from 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 about ≥ 380 nm to about ≤ 780 nm. With respect to the inventive organic light emitting device, the compounds mentioned in the experimental part may be most preferred. The organic electroluminescent device (OLED) may be a bottom- or top-emission device. Another aspect is directed to 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. In the present invention, the following defined terms, these definitions shall be applied, unless a different definition is given in the claims or elsewhere in this specification. In the context of the present specification, the term “different” or “differs” in connection with the matrix material means that the matrix material differs in their structural formula. The energy levels of the highest occupied molecular orbital, also named HOMO, and of the lowest unoccupied molecular orbital, also named LUMO, are measured in electron volt (eV). The terms “OLED” and “organic light-emitting diode” are simultaneously used and have the same meaning. The term “organic electroluminescent device” as used herein may comprise both organic light emitting diodes as well as organic light emitting transistors (OLETs). As used herein, „weight percent“, „wt.-%”, wt%, „percent by weight”, „% by 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 the respective electron transport layer thereof and multiplied by 100. It is understood that the total weight percent amount of all components, substances and agents of the respective electron transport layer and electron injection layer are selected such that it does not exceed 100 wt.-%. As used herein, „volume percent“, „vol.-%”, „percent by volume”, „% by 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 the respective electron transport layer thereof and multiplied by 100. It is understood that the total volume percent amount of all components, substances and agents of the cathode layer are selected such that it does not exceed 100 vol.-%. All numeric values are herein assumed to be modified by the term "about", whether or not explicitly indicated. As used herein, the term "about" refers to variation in the numerical quantity that can occur. Whether or not modified by the term „about“ the claims include equivalents to the quantities. It should be noted that, as used in this specification and the appended claims, the singular forms „a”, „an”, and „the“ include plural referents unless the content clearly dictates otherwise. The term “free of”, “does not contain”, “does not comprise” does not exclude impurities. Impurities have no technical effect with respect to the object achieved by the present invention. The term “free of” a compound means that such compound / material is not deliberately added to the layer during processing. Preferably, the semiconducting layer according to the invention and layers in an OLED formed thereof are essentially non-emissive or non-emitting. The operating voltage, also named U, is measured in Volt (V) at 10 milliAmpere per square centimeter (mA / cm2). The candela per Ampere efficiency, also named cd / A efficiency is measured in candela per ampere at 10 milliAmpere per square centimeter (mA / cm2). The external quantum efficiency, also named EQE, is measured in percent (%). The color space is described by coordinates CIE-x and CIE-y (International Commission on Illumination 1931). For blue emission the CIE-y is of particular importance. A smaller CIE-y denotes a deeper blue color. Efficiency values are compared at the same CIE-y. The highest occupied molecular orbital, also named HOMO, and lowest unoccupied molecular orbital, also named LUMO, are measured in electron volt (eV). The term “OLED”, “organic light emitting diode”, “organic light emitting device”, “organic optoelectronic device” and “organic light-emitting diode” are simultaneously used and have the same meaning. The term “life-span” and “lifetime” are simultaneously used and have the same meaning. The anode and cathode may be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer. Room temperature, also named ambient temperature, is 23oC. Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Reference will now be made in detail to the exemplary aspects. DESCRIPTION OF THE DRAWINGS The aforementioned components, as well as the claimed components and the components to be used in accordance with the invention in the described embodiments, are not subject to any special exceptions with respect to their size, shape, material selection and technical concept such that the selection criteria known in the pertinent field can be applied without limitations. Additional details, characteristics and advantages of the object of the invention are disclosed in the dependent claims and the following description of the respective figures which in an exemplary fashion show preferred embodiments according to the invention. Any embodiment does not necessarily represent the full scope of the invention, however, and reference is made therefore to the claims and herein for interpreting the scope of the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the present invention as claimed. FIG.1 is a schematic sectional view of an organic light emitting diode (OLED), according to an exemplary embodiment of the present invention; FIG.2 is 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. Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures. Herein, when a first element is referred to as being formed or disposed "on" or “onto” a second element, the first element can be disposed directly on the second element, or one or more other elements may be disposed there between. When a first element is referred to as being formed or disposed "directly on" or “directly onto” a second element, no other elements are disposed there between. FIG.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 includes a substrate 110, an anode 120, a light emission layer (EML) 125, 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. Onto the organic semiconductor layer 160, a cathode 190 is disposed. FIG.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 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an emission layer (EML) 150, 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 organic semiconducting layer according to the invention. Onto the electron transport layer (ETL) 160, an electron injection layer (EIL) 180 is disposed. The cathode 190 is disposed directly onto the electron injection layer (EIL) 180. Fig. 3 is a schematic sectional view of an OLED 100, according to another 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 includes 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, the ETL 160 is the organic semiconducting layer comprising the compound according to the present invention. Fig. 4 is a schematic sectional view of an OLED 100, according to another 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 includes 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 (n-type CGL) 185, a hole generating layer (p-type charge generation 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. In this embodiment of Fig. 4, the first electron transport layer (ETL) 160 is the organic semiconducting layer comprising the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention. While not shown in Fig.1, Fig.2, Fig.3 and Fig.4, a sealing layer may further be formed on the cathode electrodes 190, in order to seal the OLEDs 100. In addition, various other modifications may be applied thereto. Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Synthesis procedures 2-(naphthalen-2-yl)-4,6-bis(3-(triphenylsilyl)phenyl)-1,3,5-triazine (E1) 10 g [112719-97-8]; 1.9 eq. [1253912-58-1]; 0.03 eq. [14221-01-3]; 2.5 eq. K2CO3in 180 mL tetrahydrofuran (THF) / 45 mL H2O under N2atmosphere are heated at reflux overnight. The supension is cooled to RT, filtered and washed with THF. The filter cake is dried, dissolved in 1 L warm dichloromethane (DCM) and filtered through a pad of Florisil®. Afterwards the dichloromethane is concentrated to ~100 mL and diluted with another 100 mL of hexanes. Filtration and drying yield 18.1 g (60%) of 2-(naphthalen-2-yl)-4,6-bis(3- (triphenylsilyl)phenyl)-1,3,5-triazine as white solid (HPLC 99.8%). Further purification is achieved by high vacuum sublimation. ESI-MS m / z = 876 [M+] 2-phenyl-4-(3'-phenyl-[1,1':2',1''-terphenyl]-4-yl)-6-(4-(triphenylsilyl)phenyl)- 1,3,5-triazine (E3) 12.5 g [30894-93-0], 1 eq. [852475-03-7], 0.05 eq. [14221-01-3], 2 eq. K2CO3 in 168 ml THF / 42 ml H2O are boiled under N2 atmosphere overnight. The precipitate is filtered off and washed with water. Then it is dissolved in 1 L DCM and filtered through a pad of SiO2 / Florisil®. Then 1.2 L hexanes are added and the mixture is concentrated to around 500 mL. The formed solid precipitate is collected to give 15.9 g 2-(4-chlorophenyl)-4-phenyl-6-(4- (triphenylsilyl)phenyl)-1,3,5-triazine (HPLC 99.7%, HPLC-MS m / z 603). 15.9 g 2-(4-chlorophenyl)-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine), 1.3 eq. [2488716-94-3], 0.01 eq. [1798782-02-1]; 2.5 eq. K3PO4 in 104 ml THF / 26 ml H2O are heated at reflux for 3 days at 60 °C under N2 atmosphere. The precipitate is filtered off and washed with THF. It is then dissolved in 800 mL DCM and filtered through a pad of Florisil®. The organic layer is evaporated and the residue stirred in 50 mL THF. The slurry is filtered and washed with THF. The solid is then recrystallized from toluene (250 mL) and the crystals washed with hexanes. This yields 11 g 2-phenyl-4-(3'-phenyl-[1,1':2',1''-terphenyl]-4-yl)-6-(4- (triphenylsilyl)phenyl)-1,3,5-triazine as a white solid (HPLC 99.7%). Further purification is achieved by high vacuum sublimation. (ESI-MS m / z = 796 [M+]) 2-phenyl-4-(3'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)-6-(3-(triphenylsilyl)phenyl)- 1,3,5-triazine (E4) 7.2 g [30894-93-0], 2.2 eq. [1253912-58-1], 0.01 eq. [1798781-99-3], 2 eq. K3PO4in 100 mL dioxane / 25 mL H2O under N2atmosphere are stirred at 40 °C overnight. Then the mixture is diluted with another 30 mL dioxane and stirred for a further 6 days. During this time, 2 x 0.01eq. [1798781-99-3] is added and the temperature increased to 55°, then 65°C. The aqueous phase is separated and the dioxane evaporated. The residue is taken up in DCM (700 mL) and the extract is passed through a pad of Florisil®. Three subsequent recrystallizations from toluene are performed and the obtained solid is finally washed washed with hexane and acetone. This yields 7.7 g 2-phenyl-4-(3'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)-6-(3- (triphenylsilyl)phenyl)-1,3,5-triazine as a white solid (HPLC 99.9%). Further purification is achieved by high vacuum sublimation. (ESI-MS m / z = 903 [M+]) Supporting materials for device experiments F1 is F3 is CAS 2032364-64-8 F4 is H09 is a blue emitter host and BD200 is a blue emitter dopant, both commercially available from SFC, Korea. Tested compounds Compounds according to the invention: OLED Tests To assess the performance of the inventive examples compared to the prior art, the current efficiency is measured at 20°C. The current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between 0V and 10V. Likewise, the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd / m² using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) for each of the voltage values. The cd / A efficiency at 15 mA / cm2 is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively. In bottom emission devices, the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE). To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA / cm2. In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the mirco-cavity. Therefore, the efficiency EQE will be higher compared to bottom emission devices. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA / cm2. Lifetime LT of the device is measured at ambient conditions (20°C) and 30 mA / cm², using a Keithley 2400 sourcemeter, and recorded in hours. The brightness of the device is measured using a calibrated photo diode. The lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value. The increase in operating voltage ∆U is used as a measure of the operational voltage stability of the device. This increase is determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours. ∆U=[U100 h)- U(1h)]. The smaller the value of ∆U the better is the operating voltage stability. Example 1: Blue fluorescent top emission OLED Blue fluorescent top emission OLEDs with a layer stack in accordance with Table 1 have been prepared. Table 1: The observed device performance is shown in Table 2. Table 2: In comparison with state-of-art compound C2, the inventive compounds E1 enabled lower operational voltage, higher current efficiency, longer lifetime and higher voltage stability. Example 2: Blue fluorescent top emission OLED Blue fluorescent top emission OLEDs with a layer stack in accordance with Table 3 have been prepared. Table 3: The observed device performance is shown in Tables 4 and 5. Table 4: In comparison with state-of-art compound C2, the inventive compounds E1 and E4 enable lower operational voltage, longer lifetime and higher voltage stability. Table 5: In comparison with state-of-art compounds C1 and C3, the inventive compounds E2 and E3 enable longer lifetime and higher voltage stability. The features disclosed in the foregoing description and in the dependent claims may, both separately and in any combination thereof, be material for realizing the aspects of the disclosure made in the independent claims, in diverse forms thereof.

Claims

1. Claims1. An organic semiconducting material comprising a compound represented by one of thefollowing formulas (Ia), (Ib) or E4wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6to C30aryl;- R2to R6are independently selected from the group consisting of H, D and C6to C18aryl, wherein - R2is C6to C18aryl; and / or - R2and R3are independently C6to C18aryl; and / or - R3and R4are independently C6to C18aryl; and / or - R4and R5are independently C6to C18aryl; and / or - R5and R6are independently C6to C18aryl; and / or - R6is C6to C18aryl; - R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl; - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings.

2. The organic semiconducting material according to claim 1, wherein m, n, p and q areindependently 1 or 2.

3. The organic semiconducting material according to claim 1 or 2, wherein Ar1 to Ar9 areindependently selected from the group consisting of phenyl, biphenyl-yl, and naphthyl.

4. The organic semiconducting material according to any of the preceding claims, whereinR2and R6are independently selected from the group consisting of H, D, phenyl, biphenyl-yl, and naphthyl.

5. The organic semiconducting material according to any of the preceding claims, whereinR1is selected from the group consisting of phenyl, biphenyl-yl and naphthyl.

6. The organic semiconducting material according to any of the preceding claims, whereinR7is selected from the group consisting of naphthyl and phenanthryl.

7. The organic semiconducting material according to any of the preceding claims, whereinthe organic semiconducting material further comprises a metal salt, a metal complex or a mixture thereof.

8. The organic semiconducting material according to any of the preceding claims, whereinthe following compounds are excluded9. The organic semiconducting material according to any of the preceding claims, whereinthe compound of formula (Ib) is unsubstituted.

10. The organic semiconducting material according to any of the preceding claims, wherein compound of formulas (Ia), (Ib) and E4 is unsubsituted.

11. The organic semiconducting material according to any of the preceding claims, wherein R1is selected from the group consisting of C6to C60aryl and C3to C59heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six- membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7.

12. An organic electronic device comprising the organic semiconducting material according to any of the preceding claims.

13. A display device comprising the organic electronic device according to claim 12.

14. A compound represented by one of the following formulas (IIa), (IIb) or E4wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar1to Ar9are independently selected from C6 to C30 aryl; - R2to R6are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R2is C6 to C18 aryl; and / or - R2and R3are independently C6 to C18 aryl; and / or - R3and R4are independently C6 to C18 aryl; and / or - R4and R5are independently C6 to C18 aryl; and / or - R5and R6are independently C6 to C18 aryl; and / or - R6is C6 to C18 aryl;- R1is a C6to C60aryl or a C3to C59heteroaryl comprising only six-membered aromatic rings, wherein the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; and - R7is selected from the group consisting of C10to C30condensed aryl and C5to C29condensed heteroaryl, wherein the C10to C30condensed aryl and C5to C29condensed heteroaryl comprise only six-membered aromatic rings.

15. The compound according to claim 14, wherein the following compounds are excluded16. The compound according to Claim 14 or 15, wherein the compound of formula (IIb) is unsubstituted.

17. The compound according to any one of the claims 14 to 16, wherein the compound of formulas (IIa), (IIb), and E4 are unsubstituted.

Citation Information

Patent Citations

  • Organic electroluminescent compound, multiple host materials and this comprehensive organic electroluminescent device

    DE102021100597A1

  • Organic electroluminescent compound, several host materials and this comprehensive organic electroluminescent device

    DE102022102199A1

  • Heterocyclic radicals or diradicals and their dimers, oligomers, polymers, di-spiro and polycyclic derivatives as well as their use in organic semiconductor materials and electronic devices.

    EP1837926B1

  • Pyrido(3,2-h)chinazolins and / or 5,6-Dihydro derivatives thereof, method for their manufacture and endowed organic semiconductor material containing them

    EP1970371A1

  • Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs

    EP2722908A1