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

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.

Description

[0001] Compound, organic semiconducting material, organic electronic device, and display device

[0002] TECHNICAL FIELD

[0003] 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.

[0004] BACKGROUND OF THE INVENTION

[0005] Organic semiconducting devices, such as organic light-emitting diodes OLEDs, which are self- emiting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. Atypical 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.

[0006] Performance of an organic light emiting diode maybe 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.

[0007] 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.

[0008] 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.

[0009] WO 2018 / 215355 Al discloses a phosphorous-containing compound and an organic electronic device comprising an organic semiconductor layer, wherein at least one organic semiconductor layer comprises the compound.

[0010] CN 109 721 598 A discloses a display panel comprising an organic light emiting device, wherein the organic light emiting device includes an anode a hole injection layer, a hole transmission layer, an organic light emitting layer, an electron transmission layer, an electron injection layer and a cathode; and the organic light emitting device further includes a molecular self-assembly layer arranged between the cathode and the electron injection layer, and a material of the molecular self-assembly layer is a compound represented by Ar-Lm-An, wherein Ar is a nitrogen-containing aromatic heterocyclic group, L is a linking group and is one selected from an aryl and heteroaryl group, m is one selected from o, i and 2; and An is an anchor group anchoring the compounds represented by the Ar-Lm-An to the surface of the cathode.

[0011] WO 2023 / 213705 Ai discloses an organic light emitting diode comprising an anode, a cathode, a first emission layer, a second, emission layer, a first charge generation layer and a first electron transport layer stack; and to a display device or lighting device comprising the same.

[0012] It is, therefore, the object of the present invention to provide compounds and semiconducting materials, especially such compounds and semiconducting materials with improved LUMO values, 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.

[0013] DISCLOSURE

[0014] This object is achieved by a compound of the following formula (I) wherein

[0015] - R3to R2are independently C1 to C22hydrocarbyl comprising at least one sp3-hybridized ca Aon atom, wherein the C1to C22hydrocarbyl is bonded to the P-atom of formula (I) via an sp3- hybridized carbon atom of the C1to C22hydrocarbyl;

[0016] - L3, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0017] - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl; - Rs to Rf are independently selected from the group consisting of H, D, C1 to C(-> alkyl and substituted or unsubstituted C® to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0018] This object is achieved by an organic semiconducting material comprising the compound according to the present invention.

[0019] This object is further achieved by an organic electronic device comprising the organic semiconducting material according to the present invention.

[0020] This object is further achieved by a display device comprising at least one organic electronic device according to the present invention.

[0021] Compound

[0022] According to one aspect, the present invention relates to a compound of the following formula (I).

[0023] In formula (I), R1and R2are independently selected as C1 to C22hydrocarbyl, wherein the C1 to C22 hydrocarbyl comprises at least one sp3-hybridized carbon atom.

[0024] In terms of the present disclosure, hydrocarbyl is a univalent group formed by removing a hydrogen atom from a hydrocarbon, e.g. ethyl, tolyl etc. A hydrocarbylene is a two- or more- valent group formed by removing two or more hydrogen atoms from a hydrocarbon, e.g. ethylene, tolylene etc.

[0025] It is provided that the C1 to C22hydrocarbyl comprises at least one spa-carbon atom.

[0026] A sp3-carbon atom is a sp» hybridized carbon atom, that is, a tetravalent carbon atom forming single covalent bonds (sigma bonds) with atoms of other elements, especially p-block elements, such as H, O, C, N, halogen etc. For example, in an alkane, cycloalkane, polycyclic alkane etc., ail carbon atoms are sp3-hybridized.

[0027] R1and R2are bonded to the P-atom of formula (I) via a sps-hybridized carbon atom of the Ci to C22 hydrocarbyl. Especially, in case that the respective R1and R2comprises an aromatic part, bonding of the respective R1and R2group to the P-atom is not made via a single bond between the aromatic part and the P-atom.

[0028] R!and Ramay be independently selected as G to C20hydrocarbyl, G to Cig hydrocarbyl, G to CJ6 hydrocarbyl, C1 to Ci4hydrocarbyl, G to C12 hydrocarbyl, C1 to CJOhydrocarbyl, G to C§ hydrocarbyl, G to G hydrocarbyl, G to C5hydrocarbyl, G to C4hydrocarbyl, C1 to C3hydrocarbyl, G to C2hydrocarbyl, or C1 hydrocarbyl.

[0029] R1and R2may be independently selected from the group consisting of C1 to C22alkyl, C3to C22cycloalkyl, and G to C22arylalkyl. R1and R2may be independently selected from the group consisting of G to C20alkyl, C3to C20cycloalkyl, and C6 to C20 arylalkyl. R1and R2may be independently selected from the group consisting of C1 to Gs alkyl, C3to Gs cycloalkyl, and C6 to C18 arylalkyl. R1and R2may be independently selected from the group consisting of G to Ge alkyl, C3to Gr, cycloalkyl, and C6 to C16 arylalkyl. R* and Ramay be independently selected from the group consisting of Cito CJ4alkyl, C3to C14cycloalkyl, and G to CMarylalkyl. R1and R2may be independently selected from the group consisting of CitoC12 alkyl, C3to C12 cycloalkyl, and G to C12 arylalkyl. R1and R2may be independently selected from the group consisting of Cito C10 alkyl, C3to C10 cycloalkyl, and G to Go arylalkyl. R1and R2may be independently selected from the group consisting of C1 to Cs alkyl, C3to Cs cycloalkyl, and G to Cs arylalkyl. R1and R2may be independently selected from the group consisting of C1 to G alkyl, C3to G cycloalkyl, and G to C7arylalkyl. R1and R2may be independently selected from the group consisting of Cito C5alkyl, C3to C6 cycloalkyl, and C6 to C7arylalkyl. R1and R2maybe independently selected from the group consisting of Cito C4alkyl, C3to C6 cycloalkyl, and C6 to C7arylalkyl. R1and R2may be independently selected from the group consisting of G to C3alkyl, C3to C6 cycloalkyl, and C6 to C7arylalkyl. R1and R2may be independently selected from the group consisting of Cito C2alkyl, C3to G cycloalkyl, and G to C7arylalkyl. R1and R2may be independently selected from the group consisting of methyl, C3to G cycloalkyl, and G to C7arylalkyl.

[0030] R1and R2may be independently selected as G to C22alkyl, G to Go alkyl, G to C18 alkyl, G to C16 alkyl, C1 to Ci4alkyl, G to C12 alkyl, G to C1Oalkyl, G to Cs alkyl, C1 to G alkyl, G to C5alkyl, C1 to C4alkyl, G to C3alkyl, G to C2alkyl, or methyl.

[0031] L1, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene.

[0032] If one or more of L1, A and L2is substituted, that is, selected as substituted phenylene or substituted naphthylene, the one or more substituent(s) attached to the phenylene and / or naphthylene are independently selected from the group consisting of D, G to G alkyl, and substituted or unsubstituted G toC12 aryl. If the respective G toC12 aryl is substituted, the one or more substituent(s) may be independently selected from the group consisting of D and G to G alkyl. If one or more of L1, A and L2is substituted, that is, selected as substituted phenylene or substituted naphthylene, the one or more substituent(s) attached to the phenylene and / or naphthylene may be independently selected from the group consisting of D, G to C4alkyl, and substituted or unsubstituted phenyl, wherein if the phenyl is substituted, the one or more substitaent(s) are independently selected from the group consisting of D and G to C4alkyl. If one or niore of L\ A and L2is substituted, that is, selected as substituted phenylene or substituted naphthylene, the one or more substituent(s) atached to the phenylene and / or naphthylene may be independently selected from the group consisting of D, C> to C4alkyl, and unsubstituted phenyl.

[0033] If one or more of L1, A and L2is substituted or unsubstituted naphthylene, the naphthylene may be selected form the group consisting of naphthalene-i,2-diyl and naphthalene-i,5-diyl and naphthalene-i,4-diyl. naphthalene-i,4-diyl.

[0034] In the above formulas, represents the binding positions.

[0035] If at least one of L1, A and L2is phenylene, the phenylene may be independently selected from the group consisting of meta-phenylene and para-phenylene.

[0036] It may be provided that at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L1, A and L® is substituted or unsubstituted naphthylene. In other words, it may be provided that not all of Ll, A and L2are a direct bond at the same time. It may be provided that at least one of L1, A and L2is substituted or unsubstituted phenylene. It may be provided that at least one of L1, A and L2is substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with one C1 to C6 hydrocarbyl group. It may be provided that at least one of L1, A and L2is substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with one selected from the group consisting of C1 to C4alkyl and phenyl. It may be provided that at least one of L1, A and Lais substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with one selected from the group consisting of tert-butyl and phenyl.

[0037] According to a preferred embodiment,

[0038] L1is selected from the group consisting of substituted or unsubstituted phenylene or unsubstituted naphthalene, A is a direct bond and L2is a direct bond; or

[0039] L1is selected from substituted or unsubstituted phenylene, A is a direct bond, and L2is selected from substituted or unsubstituted phenylene or unsubstituted naphthalene; or

[0040] L1is selected from naphthalene, A is a direct bond, and L2is selected from substituted or unsubstituted phenylene; wherein the substituent of the substituted phenylene is selected from phenyl, naphthyl, or Ci to C4alkyl, wherein the phenyl may or may not substituted with one or more C1 to C4alkyl; preferably the substituent is selected from phenyl, methyl or tert-butyl, even more preferred from phenyl or tert-butyl. wherein denotes the binding position to the phosphorus atom and “*2” denotes the binding position to the benzoquinazoline group.

[0041] Thereby, particularly improved performance may be obtained, especially the LUMO of compounds of formula (I) may be in the range which may be particular suitable for use as electron transport material in an organic electronic device.

[0042] In formula (I), R3to R9are independently selected from the group consisting of H, D, Cj to Cf, alkyl and substituted or unsubstituted C6 to Cfe aryl. In formula (I), R3to R9may be independently selected from the group consisting of H, D, and substituted or unsubstituted C6 to Cfearyl. R3to R9may be independently selected from the group consisting of H, D, phenyl, biphenyl-yl and naphthyl. R3to R9may be independently selected from the group consisting of H, D, and phenyl. If the respective C6to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0043] In formula (I), R3to R6and R9may be independently selected from the group consisting of H and D; and R7and R8may be independently selected from the group consisting of (h to C6 alkyl und substituted or unsubstituted C6 to C12, wherein if the respective C6 to C!aaryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl. In formula (I), Rs to R6and R9may be independently selected from the group consisting of H and D; and R7 and R8may be independently selected from the group consisting of substituted or unsubstituted C6 to C12, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C4alkyl. In formula (I), R3 to R6and R? may be independently selected from the group consisting of H and D; and R? and R8may be independently selected from the group consisting of substituted or unsubstituted phenyl, biphenyl-yl and naphthyl, wherein if the respective phenyl, biphenyl-yl and naphthyl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C4alkyl. In formula (I), R3to R6and R9may be Independently selected from the group consisting of H and D; and R7and R8may be independently selected from the group consisting of substituted or unsubstituted phenyl, wherein if the phenyl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C4alkyl.

[0044] In one embodiment, a compound of the following formula (I) is provided 0) wherein

[0045] - R1to R2are independently C1 to C6 hydrocarbyl comprising at least one sp3-hybridized carbon atom, wherein the C1 to C6 hydrocarbyl is bonded to the P-atom of formula (I) via an spa- hybridized carbon atom of the C1 to C6 hydrocarbyl; - L1, A and Laare independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L1, A and L2is substituted or unsubstituted naphthylene;

[0046] - wherein, if one or more of L1, A and Lais substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl;

[0047] - R3 to R9are independently selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6to C12aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl. In one embodiment, a compound of the following formula (I) is provided wherein

[0048] - R’ to R2are independently C1 to C6 alkyl; preferably R* and Raare selected the same and are selected from methyl, ethyl, tert-butyl or neo-pentyl;

[0049] - L1, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L1, A and L2is substituted or unsubstituted naphthylene; - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted C6 toC12 aryl, wherein if the respective C6 to C12 aiyl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl; - R3 to R6and R9 are independently selected from the group consisting of H, D, G to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C13aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl;

[0050] - R7and R8are independently selected from the group consisting of C1 to C6 alkyl and substituted or unsubstituted C6, to Cl2aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0051] In one embodiment, a compound of the following formula (I) is provided wherein

[0052] - R* to R2are independently C1 to 0* alkyl; preferably R1and R2are selected the same and are selected from methyl, ethyl, tert-butyl or neo-pentyl;

[0053] - L1, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L1, A and L2is substituted or unsubstituted naphthylene;

[0054] - wherein, if one or more of LJ, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, to C1C6alkyl, and substituted or unsubstituted C6, to C12 aryl, wherein if the respective C6, toC12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl;

[0055] - R3 to R6and R9are independently selected from the group consisting of H, D, C1 to C6, alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl; preferably Ra to R6and R9are H or D, even more preferred R3 to R6and R9are H;

[0056] - R7 and R8are independently selected from the group consisting of substituted or unsubstituted C6 to Ctaaryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0057] In one embodiment, the compound of formula (I) is represented by the following formula (la)

[0058] In one embodiment, the compound of formula (I) is represented by the following formula (la)

[0059] wherein

[0060] - R1to Raare independently C1 to C6 alkyl; preferably R1and >aare selected the same and are selected from methyl, ethyl, tert-butyl or neo-pentyl; - L1, A and Laare independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L’, A and L2is substituted or unsubstituted naphthylene;

[0061] - wherein, if one or more of L’, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted C6, to C12 aryl, wherein if the respective C6 toC12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C<> alkyl ;

[0062] - R3 to R6and Rf are independently selected from the group consisting of H, D, C1to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0063] In one embodiment, the compound of formula (I) is represented by the following formula (la)

[0064] - R1to R2are independently C1 to C6 alkyl; preferably R’ and Raare selected the same and are selected from methyl, ethyl, tert-butyl or neo-pentyl; I

[0065] I - L1is selected from the group consisting of a substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0066] - A is a direct bond;

[0067] - L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0068] - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl;

[0069] - R3 to R6and R? are independently selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 toC12 aryl, wherein if the respective C6 to Cl2aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0070] In one embodiment, the compound of formula (I) is represented by the following formula (la)

[0071] - R1to R2are independently C3to C6 alkyl; preferably R1and R2are selected the same and are selected from methyl, ethyl, tert-butyl or neo-pentyl;

[0072] - L!is selected from the group consisting of a substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0073] - A is a direct bond;

[0074] - L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0075] - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, Csto C6 alkyl, and substituted or unsubstituted C6 to C>2aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1to Ca allyl; - R3, Rs, R6and are H;

[0076] - Ms selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl. In one embodiment, the compound of formula (I) is represented by the following formula (lb)

[0077] In one embodiment, the compound of formula (I) is represented by the following formula (lb) wherein - L1, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene wherein at least one of L1, A and Lais substituted or unsubstituted phenylene and / or at least one of L1, A and L2is substituted or unsubstituted naphthylene;

[0078] - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, G to C6 alkyl, and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl;

[0079] - R3 to R6and R9 are independently selected from the group consisting of H, D, G to C6 alkyl and substituted or unsubstituted G to C12 aryl, wherein if the respective C6 to C12 aiyl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and G to C6 alkyl. In one embodiment, the compound of formula (I) is represented by the following formula (lb) wherein

[0080] - L1is selected from the group consisting of a substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0081] - A is a direct bond;

[0082] - L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0083] - wherein, if one or more of L1, A and L2is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 allcyl, and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to Cf> alkyl;

[0084] - R3 to R6and R” are independently selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl.

[0085] In one embodiment, the compound of formula (I) is represented by the following formula (lb) wherein - L1is selected from the group consisting of a substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0086] - A is a direct bond;

[0087] - 1 / are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;

[0088] - wherein, if one or more of L1, A and L2 is substituted, the one or more substituent(s) are independently selected from the group consisting of D, C1 to C6 alkyl, and substituted or unsubstituted Cs to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C5to Cg alkyl;

[0089] - R3, R5, R6and R9 are H;

[0090] - Rfrs selected from the group consisting of H, D, C1 to C6 alkyl and substituted or unsubstituted C6 to C12 aryl, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C1 to C6 alkyl. The compound of formula (I) may be selected from El to E15 E15.

[0091] In one embodiment, the following formula is excluded: Organic semicondugting material

[0092] According to a further aspect, the invention is related to an organic semiconducting material. The organic semiconducting material comprises the compound of formula (I) according to the invention as described herein.

[0093] The organic semiconducting material may be an electron transporting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 50 wt.-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 60 wt.-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 70 wt.-% with respect to the total weight of the organic semiconducting material. The or ganic semiconducting material may comprise the compound of formula (I) in an amount of at least 80 wt.-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 90 wt.-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 95 wt-% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may comprise the compound of formula (I) in an amount of at least 98 wt.-% with respect to the total weight of the -% with respect to the total weight of the organic semiconducting material. The organic semiconducting material may consist of the compound of formula (I). The organic semiconducting material may comprise besides the compound of formula (I) an electrical dopant, especially an electrical n-dopant

[0094] 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.

[0095] In the context of the present invention “embedded into an electron transport matrix” means homogenously mixed with the electron transport matrix.

[0096] The electrical dopant as referred to herein is especially selected from elemental metals, metal salts, metal complexes and organic radicals.

[0097] In one embodiment, the electrical dopant is selected from alkali metal salts and alkali metal complexes; preferably from lithium salts and lithium organic comptexes; more preferably from lithium halides and lithium organic chelates; even more preferably from lithium fluoride, a lithium quinolmolate, lithium borate, lithium phenolate, lithium pyridinolate or from a lithium complex with a Schiff base ligand; most preferably,

[0098] - the lithium complex has the formula II, III or IV: wherein

[0099] Ai to At, are same or independently selected from CH, CR, N, 0;

[0100] R is same or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl with 1 to 20 carbon atoms; and more preferred A, to As are CH,

[0101] - the borate based organic ligand is a tetra(iH-pyrazol-i-yl)borate,

[0102] - the phenolate is a 2-(pyridin-2-yl)phenolate, a 2-(diphenylphosphoryl)phenolate, an imidazol phenolate, 2-(pyridin-2-yl)phenolate or 2-(i-phenyl-iH-benzo[d]imidazol-2- yl)phenolate,

[0103] - the pyridinolate is a 2-(diphenylphosphoryl)pyridm-3-olate, the lithium Schiff base has the structure too, 101, 102 or 103:

[0104] 100 101 102 103

[0105] 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). According to one embodiment of the present invention the electron transport layer comprises a metal, preferably selected from alkali metals, alkaline earth metals, rare earth metals and metals of the transition period Ti, V, Cr and Mn, especially selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eli, Tm, Yb; more preferably from Li, Na, K, Rb, Cs, Mg and Yb, even more preferably from Li, Na, Cs and Yb, most preferably from Li, Na and Yb. The most practical benchmark for the strength of an n-dopant is the value of its redox potential. There is no particular limitation in terms how negative the value of the redox potential can be.

[0106] As reduction potentials of usual electron transport matrices used in organic semiconductors are, if measured by cyclic voltammetry against ferrocene / ferrocenium reference redox couple, roughly in the range from about - 0.8 V to about - 3.1V; the practically applicable range of redox potentials for n-type dopants which can effectively n-dope such matrices is in a slightly broader range, from about - 0.5 to about - 3.3 V.

[0107] The measurement of redox potentials is practically performed for a corresponding redox couple consisting of the reduced and of the oxidized form of the same compound.

[0108] In case that the n-type dopant is an electrically neutral metal complex and / or an electrically neutral organic radical, the measurement of its redox potential is actually performed for the redox couple formed by

[0109] (i) the electrically neutral metal complex and its cation radical formed by an abstraction of one electron from the electrically neutral metal complex, or

[0110] (ii) the electrically neutral organic radical and its cation formed by an abstraction of one electron from the electrically neutral organic radical.

[0111] Preferably, the redox potential of the electrically neutral metal complex and / or of the electrically neutral organic radical may have a value which is more negative than - 0.5 V, preferably more negative than -- 1.2 V, more preferably more negative than - 1.7 V, even more preferably more negative than - 2.1V, most preferably more negative than - 2.5 V, if measured by cyclic voltammetry against ferrocene / ferrocenium reference redox couple for a corresponding redox couple consisting of (i) the electrically neutral metal complex and its cation radical formed by an abstraction of one electron from the electrically neutral metal complex, or

[0112] (ii) the electrically neutral organic radical and its cation formed by an abstraction of one electron from the electrically neutral organic radical. In a preferred embodiment, the redox potential of the n-dopant is between the value which is about 0.5 V more positive and the value which is about 0.5 V more negative than the value of the reduction potential of the chosen electron transport matrix.

[0113] 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

[0114] W2(hpp)4, as described in more detail in WO2OO5 / O86251.

[0115] 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 1 837926 Bi, W02007 / 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 dusters 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.

[0116] For the use in consumer electronics, only metals containing stable nuclides or nuclides having very long halftime of radioactive decay might be applicable. As an acceptable level of nudear stability, the nuclear stability of natural potassium can be taken. In one embodiment, the electrical may be selected from electropositive metals selected from alkali metals, alkaline earth metals, rare earth metals and metals of the first transition period Ti, V, Cr and Mn. Preferably, the n-dopant may be selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, Tm, Yb; more preferably from Li, Na, K, Rb, Cs, Mg and Yb, even more preferably from Li, Na, Cs and Yb, most preferably from Li, Na and Yb. Organic electronic device

[0117] 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 (I) 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 emiting layer and a semiconducting layer wherein

[0118] - the first light emitting layer is arranged between the anode and the cathode;

[0119] - the semiconducting layer is arranged between the first light emitting layer and the cathode; and

[0120] - the semiconducting layer comprises the organic semiconducting material according to the present invention.

[0121] The semiconducting layer may consist of the organic semiconducting material according to the present invention.

[0122] The organic light emitting diode may comprise two or more semiconducting layers comprising a semiconducting material in accordance with the invention, respectively.

[0123] The semiconducting layer maybe 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.

[0124] The semiconducting layer may be an electron transport layer and OLED may further comprise an n-type charge generation layer and the electron transport layer may be arranged between and in direct contact with the first emission layer and the n-type charge generation layer.

[0125] According to an embodiment, the organic electronic device may further comprise a first light emitting layer, wherein the semiconducting layer is arranged between the first light emitting layer and the cathode layer.

[0126] According to an embodiment, the organic electronic device may further comprise a first light emiting layer and a hole blocking layer arranged between the anode and the cathode, wherein the hole blocking layer is arranged between the first light emitting layer and the semiconducting layer.

[0127] 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:

[0128] Substrate

[0129] 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 ora 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.

[0130] Anode electrode

[0131] 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 (Sn02), aluminum zinc oxide (A1Z0) 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.

[0132] Hole injection layer

[0133] 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 ioo° C to 500® C, a pressure of io-8to 1O'3Torr (1 Torr equals 133-322 Pa), and a deposition rate of 0.1 to 10 nm / sec.

[0134] 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 8o° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.

[0135] 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 polyamline) / poly(4-styrenesulfonate (PANI / PSS).

[0136] 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-i,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-typedopant. 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; a-NPD (N,N'-Bis(naphthalen-i-yl)-N,N’-bis(phenyl)-benzidine) doped with F4TCNQ. a-NPD doped with 2, 2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile. Thep- type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%.

[0137] 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.

[0138] Hole transport layer

[0139] 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.

[0140] 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)-NsN’-diphenyl- [i,i-biphenyl]-4,4'-diamine (TPD), or N.N'-diCnaphthalen-i-ylJ-N.N'-diphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylaniine (TCTA). Among these compounds, TCTA can transport holes and inhibit excitons from being diffused into the EML.

[0141] 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 maybe 170 nm to 200 nm.

[0142] 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.

[0143] Electron blocking layer

[0144] 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.

[0145] 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 2 722 908 Al.

[0146] Photoactive layer (PAL)

[0147] The photoactive layer converts an electrical current into photons or photons into an electrical current.

[0148] 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,

[0149] It may be provided that the photoactive layer does not comprise the compound of Formula (1). The photoactive layer may be a light-emitting layer or a light-absorbing layer.

[0150] Emission layer (EML)

[0151] The emission layer may also be named first light emitting layer.

[0152] 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. However, the conditions for deposition and coating may vary, according to the compound that is used to form the EML.

[0153] It may be provided that the emission layer does not comprise the compound according to the present invention, such as the first matrix compound. The respective emission layer (EML) may be formed of a combination of a host and an emitter dopant. Example of the host are Alq3, 4,4’-N,N'-dicarbazole-biphenyl (CBP), poly(n- vinylcarbazole) (PVK), 9,io-di(naphthalene-2-yl)anthracene (ADN), 4J4',4"-tris(carbazol-9- yl)-triphenylamine(TCTA), i,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert- butyl-9,io-di-2-naphthylanthracenee (TBADN), distyrylarylene (DSA), bis(2-(s- hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2), EML3 below, Compound 1 below, and Compound 2 below.

[0154] ADN

[0155] Compound i

[0156] Compound 2

[0157] The emiter 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.

[0158] Examples of red emitter dopants are PtOEP, Ir(piq)3, and Btpjrfacac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants could also be used.

[0159] Examples of phosphorescent green emitter dopants are Ir(ppy)3(ppy = phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3are shown below. Compound 3 is an example of a fluorescent green emiter and the structure is shown below.

[0160] Compound 3

[0161] Examples of phosphorescent blue emitter dopants are Falrpic, (F2ppy)2lr(tmd) and Ir(dfppz)3, ter-fluorene, the structures are shown below. 4.4'-bis(4-diphenyl amiostyryl)biphenyl (DPAVBi), 2,5,8, 11-tetra-tert-butyl perylene (TBPe), and Compound 4 below are examples of fluorescent blue emiter dopants.

[0162] The amount of the emitter dopant may be in the range from about o.oi 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.

[0163] Hole blocking layer (HBL)

[0164] 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.

[0165] The HBL may also be named auxiliary ETL or a-ETL.

[0166] 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.

[0167] 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 a semiconducting material according to the invention, that is, may be the semiconducting layer in the organic light emitting diode according to the invention.

[0168] Electron transport layer (ETL)

[0169] The organic electronic device according to the present invention may comprise an electron transport layer (ETL).

[0170] 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.

[0171] 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.

[0172] The electron transport layer may comprise ETM materials comprising one or more electron transport compound(s) known in the art.

[0173] 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 C1 to 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.

[0174] 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.

[0175] The aromatic or heteroaromatic rings of the electron transport compound maybe 6-membered rings.

[0176] 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.

[0177] 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, respertively. 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 benzoquinazoline, preferably triazine.

[0178] 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.

[0179] 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.

[0180] Further, the electron transport layer may comprise one or more additives. The additive maybe 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 embodiment, 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(iH-pyrazol-i-yl)borate or Lithium 2-(diphenylphosphoiyl)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 1 970371 Al or WO 2013 / 079217 Ai.

[0181] The electron transport layer may have a thickness from about 1 to about 100 nm, such as from about 10' to about 50 nm.

[0182] 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.

[0183] Electron injection layer (EIL)

[0184] The optional EIL, which may facilitate injection of electrons from the cathode, maybe 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, Li20, 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.

[0185] 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.

[0186] 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.

[0187] Cathode electrode

[0188] 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)-lfthiuin (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 than 50 volume % of metal selected from Ag and Au.

[0189] 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.

[0190] The cathode may be a semi-transparent metal cathode having a thickness less than 20 nm, preferably less than 15 nm.

[0191] It is to be understood that the cathode electrode is not part of an electron injection layer or the electron transport layer.

[0192] Charge generation layer / hole generation layer

[0193] 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.

[0194] 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.

[0195] 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, FeClg, FeFg, and SbClg. Also, the host can be one selected from a group consisting of N,N'-di(naphthalen-i-yl)-N,N-diphenyl- benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-inetliylphenyl)-i,ifoiphenyl-4)4'-diamine (TPD) and N,N',N'-tetranaphthyl-benzidine (TNB).

[0196] 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.

[0197] 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.

[0198] In one embodiment, the p-type charge generation layer may include compounds of the following Chemical Formula X. wherein each of Al to A6 maybe hydrogen, a halogen atom, nitrile (-CN), nitro (-NOa), sulfonyl (-SO2R), sulfoxide (-SOR), sulfonamide (-S02NR), sulfonate (-S03R), trifluoromethyl (-CF3), ester (-COOR), amide (-CONHR or - CONRR’), substituted or unsubstituted straight-chain or branched-chain Ci-Ci2alkoxy, substituted or unsubstituted straight-chain or branched-chain C1-C12 alkyl, substituted or unsubstituted straight-chain or branched chain C2-C12 alkenyl, a substituted or unsubstituted aromatic or non-aromatic heteroring, substituted or unsubstituted aryl, substituted or unsubstituted mono- or di-arylamine, substituted or unsubstituted aralkylamine, or the like. Herein, each of the above R and R’ maybe substituted or unsubstituted Ci-Cso alkyl, substituted or unsubstituted aryl, or a substituted or unsubstituted 5- to 7-membered heteroring, or the like.

[0199] An example of such p-type charge generation layer may be a layer comprising CNHAT

[0200] The hole generating layer may be arranged on top of the n-type charge generation layer.

[0201] With regard to the method for producing the organic light emitting diode, the alternative embodiments outlined above may be applied mutatis mutandis. For example, the charge generation layer may be produced with an interlayer provided between the n-type sub-layer, and the p-type sub-layer.

[0202] 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 optional electron transport layer and / or an optional injection layer are arranged.

[0203] Display device

[0204] According to a further aspect, the invention is related to a display device comprising the organic light emitting diode according to the invention.

[0205] The display device may be a television, a tablet, or a mobile phone.

[0206] Process for preparing the organic light emiting diode According to a farther 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 (I) according to the present invention on a solid support.

[0207] The method for depositing may comprise: - deposition via vacuum thermal evaporation; deposition via solution processing, preferably the processing is selected from spincoating, printing, casting; and / or slot-die coating. 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.

[0208] 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 deuterated derivatives thereof.

[0209] The term “zero-valent” as used herein refers to a metal in the oxidation state o, 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.

[0210] 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 JI- and o-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 n-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.

[0211] 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 cyclohexyl.

[0212] 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, phenylsubstituted terphenyl (such as tetraphenyl benzene groups) etc.. “Arylene” respectively “heteroarylene”, refers to groups to which two further moieties are atached. 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.

[0213] 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 i 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 “aryr / ”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’-xanthenej. Further exemplary heteroaryl groups are diazine, triazine, dibenzofurane, dibenzothiofurane, acridine, benzoacridine, dibenzoacridine etc.

[0214] The subscripted number n in Cn-heteroaiyl merely refers t> the number of carbon atoms excluding the number of heteroatoms. In this context, it is dear that a C3heteroarylene group is an aromatic compound comprising three carbon atoms, such as pyrazole, imidazole, oxazole, thiazole and the like.

[0215] 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.

[0216] The term “alkenyl” as used herein refers to a group -CR1= CR2R3 comprising a carbon-carbon double bond.

[0217] The term “alkoxy” as used herein refers to a structural fragment of the Formula -OR with R being hydrocarbyl, preferably alkyl or cycloalkyl.

[0218] The term “thioalkyl” as used herein refers to a structural fragment of the Formula -SR with R being hydrocarbyl, preferably alkyl or cycloalkyL

[0219] 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.

[0220] 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.

[0221] 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.

[0222] 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 s 380 nm to about £ 780 nm.

[0223] 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 botom- or top-emission device.

[0224] 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.

[0225] 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.

[0226] 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).

[0227] 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).

[0228] 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 too. 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 1OO wt.-%.

[0229] 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 too. 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 too vol-%.

[0230] 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.

[0231] 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 dearly dictates otherwise.

[0232] The term “free of’, “does not contain”, “does not comprise” does not exdude 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.

[0233] Preferably, the semiconducting layer according to the invention and layers in an OLED formed thereof are essentially non-emissive or non-emitting.

[0234] The operating voltage, also named U, is measured in Volt (V) at io milliAmpere per square centimeter (mA / cm2).

[0235] The candela per Ampere efficiency, also named cd / A efficiency is measured in candela per ampere at io milliAmpere per square centimeter (mA / cm2). The external quantum efficiency, also named EQE, is measured in percent (%).

[0236] 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).

[0237] 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.

[0238] 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 23°C.

[0239] 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.

[0240] DESCRIPTION OF THE DRAWINGS

[0241] 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.

[0242] 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 fall 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;

[0243] 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.

[0244] 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.

[0245] 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.

[0246] FIG. i is a schematic sectional view of an organic semiconducting device 100 , according to an exemplary embodiment of the present invention. The organic semiconducting device loo includes a substrate no, 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.

[0247] 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 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.

[0248] 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)

[0249] 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 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 farther comprises a charge generation layer (CGL) and a second emission layer (151). Referring to Fig. 4, the OLED 100 includes a substrate no, 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 (El L) 181 and a cathode 190. In this embodiment of Fig. 4, the first electron transport layer (ETL) 160 is the semiconducting layer comprising the compound of formula (I) according to the present invention.

[0250] While not shown in Fig. 1, Fig. 2, Fig. 3 and Fig. 4, a sealing layer may farther be formed on the cathode electrodes 190, in order to seal the OLEDs 100. In addition, various other modifications may be applied thereto.

[0251] Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples.

[0252] Synthesis procedures

[0253] (4'-(2,4-diphenylbenzo[h]quinazolin-9-yl)-[i,i’-biphenyl]-3- yl)dimethylphosphine oxide (El)

[0254] 1stStep. 9-(4-Chlorophenyl)-2,4-diphenylbenzo[h]qumazolme

[0255] A 3-neck round-bottom flask was flushed with nitrogen and charged with (4- chlorophenyl)boronic acid (CAS 1679-18-1, 1.0 eq, 14.5 g), 9-bromo-2,4- diphenylbenzo[h]quinazoline (CAS 2905346-69-0, 1.0 eq, 40.0 g), tetrakis(triphenylphosphine)palladium(o) (CAS 14221-01-3, 0.01 eq, 1.1 g), potassium carbonate (CAS 584-08-7, 2 eq, 26.9 g). A deaerated mixture of 800 mL dioxane and 160 mL water was added. The reaction mixture was stirred at reflux under nitrogen atmosphere overnight. After cooling down to room temperature, a beige suspension formed. The solid was filtered, washed with dioxane, water and methanol and dried. The raw product was dissolved in toluene, the solution filtered through a silica pad, and the solvent was evaporated at low pressure. The isolated solid was recrystallized from toluene. Yield: 38.9 g (90%).

[0256] 2ndStep. (4’-(2,4-Diphenylbenzo[h]quinazoIin-9-yl)-[i,i’-biphenyl]-3- yl)dimethylphosphine oxide

[0257] A 3-neck round-bottom flask was flushed with nitrogen and charged with dimethyl(3~(4, 4,5,5- tetramethyl-i,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (CAS 2093110-21-3, 1.1 eq, 23-9 g), 9-(4-chlorophenyl)-2,4-diphenylbenzo[h]quinazoline, (1.0 eq, 34.3 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II)

[0258] (CAS 1798781-99-3, 0.01 eq, 0.5 g), potassium phosphate (CAS 7778-53-2, 3.0 eq, 49.3 g). A deaerated mixture of 340 mL dioxane and 80 ml water was added. The reaction mixture was stirred at reflux under nitrogen atmosphere overnight After cooling down to room temperature, a grey suspension formed. The solid was filtered, washed with water and methanol and dried. The raw product was dissolved in chloroform, the solution filtered through a silica pad, and the solvent was evaporated at low pressure. Further purification was done by recrystallization of the obtained solid from a mixture of toluene and ethanol and final purification by vacuum sublimation. White powder. Yield: 28.5 g (66%). (ESI-MS: 560).

[0259] (5-(2,4-diphenylbenzo[h]quijnazolm-9-yl)naphthalen-i-yl)dimethylphosphine oxide (Ea)

[0260] 1stStep. (5-Bromonaphthalen-i-yl)dimethylphosphine oxide

[0261] A 3-neck round-bottom flask was flushed with argon, charged with chlorodimethylphosphane (CAS 811-62-1, 1.0 eq, 4.5 g), 1,5-dibromonaphthalene (CAS 7351-74-8, 1.2 eq, 15.5 g), 300 mL anhydrous THF, cooled to -75°C. 2.5 M n-butyllithium (CAS 109-72-8, 1.1 eq, 13.7 g) solution in hexanes was added. The reaction mixture was stirred at -75°C under argon atmosphere for 2 hours and left at room temperature overnight. An aqueous solution of hydrogen peroxide was added to the reaction mixture at 5°C and stirred for an hour. The raw product was extracted into DCM and the extract was washed with water. Combined organic phases were dried and the solvent evaporated. Further purification of the resulting solid was done by column chromatography using a mixture of DCM and methanol as eluent. Yield: 7.9 g (60%).

[0262] 2n<* Step. Dimethyl(5-(4,4,5,5-tetramethyl-i,352-dioxaborolan-2-yl)naphthalen-i- yl)phosphine oxide

[0263] A 3-neck round-bottom flask was flushed with nitrogen and charged octamethyl-2,2'-bi(i,3,2-dioxaborolane) (CAS 73183-34-3, 1.5 eq, 10.6 g), (5- bromonaphthalen-i-yl)dimethylphosphine oxide (1.0 eq, 7.9 g), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (CAS 72287-26-4, 0.03 eq, 0.6 g), potassium acetate (CAS 127-08-2, 3 eq, 8.2 g). 200 mL anhydrous dioxane was added. The reaction mixture was stirred at 8o°C under argon atmosphere overnight. After cooling down to room temperature, a dark solution formed. The solution was diluted with DCM, filtered through a pad of celite and the solvent was evaporated at low pressure. Further purification of the obtained raw product was done by column chromatography using a mixture of DCM and methanol as eluent. Yield: 8.0 g (87%). 3rdStep. (5-(2,4-Diphenylbenzo[h]quinazolm-9-yl)naphthaleii-i- yljdimethylphosphme oxide

[0264] A 3-neck round-bottom flask was flushed with nitrogen and charged with g-bromo-2,4- diphenylbenzo[h]quinazoline (CAS 2905346-69-0, 1.0 eq, 11.9 g), dimethyl(5-(4, 4,5,5- tetramethyl-i,3,2-dioxaborolan-2-yl)naphthalen-i-yl) phosphine oxide (1.6 eq, 14.8 g), tetrakis(triphenylphosphine) palladium(o) (CAS 14221-01-3, 0.02 eq, 0.7 g), potassium carbonate (CAS 584-08-7, 2 eq, 8.0 g). A deaerated mixture of 180 mL dioxane and 30 mL water was added. The reaction mixture was stirred at 80 °C under nitrogen atmosphere for 3 days. After cooling down to room temperature, a beige suspension formed. The solid was filtered, washed with water and methanol and dried. The raw product was further purified by Soxhlet extraction with chlorobenzene and final purification was done by vacuum sublimation. White powder. Yield: 11.6 g (75%). (ESI-MS: 534).

[0265] (3-(tert-biityI)-5-(2s4-dipIieiiylbenzo[h]qijiiiazolin-9- yl)phenyl)dimethylphosphHie oxide (E3)

[0266] 1stStep. (3-bromo-5-(tert-butyl)phenyl)dimethylphosphme oxide

[0267] A 3-neck round-bottom flask was flushed with nitrogen and charged with dimethylphosphine oxide (CAS 7211-39-4, 1.4 eq, 15.0 g), i,3-dibromo-5-(tert-butyl)benzene (CAS 129316-09-2, 1.0 eq, 40.0 g), tris(dibenzylidenacetone)dipalladium(o) (CAS 51364-51-3, 0.015 eq, 1.9 g),

[0268] (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (CAS 161265-03-8, 0.03 eq, 2.4 g) and triethyl amine (CAS 121-44-8, 3 eq, 41.6 g). 550 mL deaerated anhydrous toluene was added. The reaction mixture was stirred at 1OO°C under nitrogen atmosphere overnight. After cooling down to room temperature, a greenish yellow suspension formed. Water was then added and the reaction mixture was neutralized with diluted aqueous HC1 to pH 7. The raw product was extracted from the aqueous phase into dichloromethane (DCM) and the extract was washed with water. Combined organic phases were dried, filtered through a silica pad, and the solvent was evaporated at low pressure. Next, the solid product was stirred in a mixture of DCM / cyclohexane, filtered and recrystallized from cyclohexane. Yield: 8.0 g (20%).

[0269] 2ndStep. (3-(tert-butyl)-5-(2,4-diphenylbenzo[h]quinazolin-9- yl)phenyl)dimethylphosphme oxide

[0270] A 3-neck round-bottom flask was flushed with nitrogen and charged with 2,4-diphenyl-9~ (4,4,5,5-tetramethyl-i,3,2-dioxaborolan-2-yl)benzo[h]quinazoline (CAS 2248001-50-3, 1.0 eq, 12.2 g), (3-bronio-5-(tert-butyl)phenyl)dimethylphosphine oxide (1.2 eq, 9.2 g), tetrakis(triphenylphosphine)palladium(o) (CAS 14221-01-3, 0.02 eq, 0.6 g), potassium carbonate (CAS 584-08-7, 2 eq, 7.4 g). A deaerated mixture of 110 mL dioxane and 30 mL water was added. The reaction mixture was stirred at reflux under nitrogen atmosphere overnight. After cooling down to room temperature, a yellowish solution formed. The solvent was evaporated at low pressure, the raw product was extracted into DCM and the extract washed with water. Combined organic phases were dried, filtered through a silica pad, and the solvent was evaporated at low pressure. Next, the product was macerated in a mixture of DCM / n-hexane, filtered, dried and the isolated solid product was purified by vacuum sublimation. White powder. Yield: 9.0 g (63%). (ESI-MS: 540).

[0271] (2-(2,4'<iiphenylbenzo[h]quinazoIin-9-yl)-[i>i'-biphenyl]-4- yl)dimethylphosphine oxide (E4)

[0272] 1stStep. (2-bromo-[i,i’-biphenyl]-4-yI)dimethylphosphine oxide

[0273] A 3-neck round-bottom flask was flushed with nitrogen and charged with dimethylphosphine oxide (CAS 7211-39-4, 1.4 eq, 8.2 g), 2,4-dibromo-i,i’-biphenyl (CAS 53592-10-2, 1.0 eq, 23.3 g), tris(dibenzylidenacetone) dipalladium(o) (CAS 51364-51-3, 0.015 eq, to g), (9,9- dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (CAS 161265-03-8, 0.03 eq, 1.3 g), triethyl amine (CAS 121-44-8, 3 eq, 22.7 g). 350 mL deaerated anhydrous toluene was added. The reaction mixture was stirred at ioo°C under nitrogen atmosphere overnight. After cooling down to room temperature, a yellowish suspension formed. Water was then added and the reaction mixture was neutralized with diluted aqueous HC1 to pH 7. The resulting solid precipitate was filtered, washed with cyclohexane, and the isolated raw product was recrystallized from ethyl acetate. Yield: 15.5 g (67%).

[0274] 2ndStep. (2-(2,4-<lip]ien.yIbeiizoPi]qiimazolm-9-yl)-[i,i'-bipheiiyl]-4- yl)dimethylphosphine oxide A 3-neck round-bottom flask was flushed with nitrogen and charged with 2,4-diphenyl-9- (4>4!5>5”tetramethyl"i,3,2-dioxaborolan-2-yl)benzo[h]qiiinazoline (CAS 2248001-50-3, 1.0 eq, 17.6 g), (2-bromo-[i,i'-biphenyl]-4-yl)dimethyl phosphine oxide (1.2 eq, 14.1 g), tetrakis(triphenylphosphme) palladium(o) (CAS 14221-01-3, 0.02 eq, 0.9 g), potassium carbonate (CAS 584-08-7, 2 eq, 10.5 g). A deaerated mixture of 240 mL dioxane and 40 mL water was added. The reaction mixture was stirred at 90 °C under nitrogen atmosphere overnight. After cooling down to room temperature, a yellowish suspension formed. The solid was filtered, washed with MTBE, water, methanol and n-hexane, and dissolved in BCM. The solution was filtered through a silica pad and the solvent was evaporated at low pressure. The isolated raw product was dried and purified by vacuum sublimation. Yellow powder. Yield: 8.3 g (39%). (ESI-MS: 560).

[0275] Further compounds of formula (I) may be prepared by the methods described above and / or by methods known in the art. SupBortmgj^eriMs^

[0276] Fl is

[0277] CAS 1955543-57-3 F5 is

[0278] LiQ is lithium 8-hydroxyquinolinolate, CAS 850918-68-2 H09 is a commercially available blue emitter host and BD200 is a commercially available blue emitter dopant, both available from SFC, Korea.

[0279] Tested compounds

[0280] Compounds according to the invention: Ci

[0281] 1) Example i: Blue, fluorescent top emission tandem PLED Blue fluorescent top emission OLEDs with a layer stack in accordance with Table i have been prepared.

[0282] Table i:

[0283] Layer Material c d

[0284] [vol%] [nm] anode ITO / Ag / ITO 100 / 100 / 100 10 / 120 / 10

[0285] HIL Fl:PD-2 98:2 10

[0286] HTLi Fl10029

[0287] EBLi Fa 100 5

[0288] EMLi HO9:BD2OO 97:3 20

[0289] ETLi E1-E3 or Ci 100 15 nCGL F3:Yb 98:2 8 pCGL FI:PD-2 99:1 10

[0290] HTL2 Fl 100 45

[0291] EBL2 Fa 100 5

[0292] EMLa HoprBDaoo 97:3 19

[0293] HBL F4 100 5 ETL2 Fg:LiQ 50:50 31

[0294] EIL Yb1001 cathode Ag:Mg 90:10 jg capping layer Fl10075

[0295] The observed device performance is shown in Table 2.

[0296] Table 2:

[0297] In comparison with state-of-art compound Ci, the inventive compounds E1-E3 enable higher current efficiency.

[0298] LUMP of compounds of formula (I)

[0299] The LUMO values may be calculated with the program package Orca V6.0 (Max Planck Institute fuer Kohlenforschung, Kaiser Wilhelm Platz 1, D-45470 Muelheim / Ruhr, Germany). The optimized geometries and the LUMO energy levels of the molecular structures are determined by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase. If more than one conformation is viable, the conformation with the lowest total energy is selected.

[0300] According to an embodiment, the LUMO of the compound of formula (I) is in the range of - 1.75 to -1.95, preferably in the range of - 1.76 to -1.91 eV, if calculated by above method.

[0301] In Table 3 are shown LUMO energies of compounds of formula (I). The values were calculated by above method. Table 3

[0302]

[0303] As can be seen in Table 3, the LUMO is in the range of -1.76 to -1.91 eV.

[0304] Without being bound by theory, compounds of formula (I) may be particularly suited to the use in organic electronic devices, if the LUMO is selected in this range. 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

Claims1. A compound of the following formula (I)wherein- R1to R2are independently C, to C23hydrocarbyl comprising at least one spa-hybridized carbon atom, wherein the C1 to C22hydrocarbyl is bonded to the P-atom of formula (I) via an sps-hybridized carbon atom of the Ctto C22hydrocarbyl;- L‘, A and L2are independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene;- wherein, if one or more of L’, A and L2is substituted, the one or more substituent(s) are independently selected -from the group consisting of D, C, to C6 alkyl, and substituted or unsubstituted C& to C« aryl, wherein if the respective C« to Cia aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C, to C& alkyl;- Rs to R9are independently selected from the group consisting- of H, D, C, to Cd alkyl and substituted or unsubstituted C6to C,2aryl, wherein if the respective Cs to Ci2aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and C3to C6alkyl.

2. The compound according to claim 1, wherein R1and R2are independently selected from the group consisting- of C, to C22alkyl, C3to C22cycloalkyl, and Ce to Caaarylalkyl.3- The compound according to claim 1 or 2, wherein at least one of L1, A and L2is substituted or unsubstituted phenylene and / or at least one of L1, A and L2is substituted or unsubstituted naphthylene.4- The compound according to any of the preceding claims, wherein at least one of L1, A and L2is substituted phenylene, wherein in the substituted phenylene the phenylene is substituted with one C, to C& hydrocarbyl group.

5. The compound according to any of the preceding claims, wherein naphthylene is selected form the group consisting of naphthalene-i,2-diyl and naphthalene-i,5-diyl.

6. The compound according to any of the preceding claims, wherein R3 to R6and R9are independently selected from the group consisting of H and D; and R? and R8are independently selected from the group consisting of C1 to G alkyl und substituted or unsubstituted C6 to C12, wherein if the respective C6 to C12 aryl is substituted, the one or more substituent(s) are independently selected from the group consisting of D and Ci to C6 alkyl.

7. The compound according to any of the preceding claims, wherein R3 to R6and R9are independently selected from the group consisting of H and D; and R7and R8are independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl. 8, An organic semiconducting material comprising the compound according to any of the preceding claims.

9. An organic electronic device comprising a first electrode, a second electrode and an organic semiconducting layer; wherein - the organic semiconducting layer is arranged between the first electrode and the second electrode; and- the organic semiconducting layer consists of the organic semiconducting material according to claim 8.

10. Display device comprising the organic electronic device according to claim 9.

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