Organic electronic device and display apparatus comprising the same and organic compound for use in organic electronic device

Abstract

The present invention relates to an organic electronic device comprising a semiconducting layer, said semiconducting layer comprising a compound of formula (1).

Description

TECHNICAL FIELD

[0001] The present invention relates to an organic electronic device, a display device comprising the organic electronic device. The present invention also relates to novel compounds useful in organic electronic devices. BACKGROUND

[0002] Organic electronic devices, for example organic light emitting diodes, OLEDs, are self-emitting devices having a wide viewing angle, excellent contrast, rapid response, high luminance, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode, a hole transport layer, HTL, a light emitting layer, EML, an electron transport layer, ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, EML, and ETL are thin films formed of organic compounds.

[0003] When a voltage is applied to the anode and the cathode, holes injected from the anode electrode move to the EML via the HTL, while electrons injected from the cathode electrode move to the EML via the ETL. The holes and the electrons recombine in the EML to generate excitons. Light is emitted when the excitons drop from the excited state to the ground state. The injection and flow of the holes and the electrons should be balanced so that the OLED having the above structure has excellent efficiency and / or long lifetime.

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

[0005] In particular, there is a need to develop an organic semiconductor layer capable of improving the electron transport, electron injection, and electron generation properties. Thereby the operating voltage of the OLED can be reduced. A lower operating voltage is important for reducing power consumption and improving battery life, especially for mobile devices.

[0006] In addition, there is a need to develop an organic electronic device that improves efficiency.

[0007] Improving efficiency is important for reducing power consumption and prolonging battery life, for example for mobile display devices.

[0008] There is a need to improve the performance of organic semiconductor materials, organic semiconductor layers, and organic electronic devices thereof, in particular by improving the properties of the compounds contained therein to achieve a reduced operating voltage and improved efficiency. SUMMARY

[0009] One aspect of the present invention provides an organic electronic device, the organic electronic device comprising an anode, a cathode, at least one photoactive layer, and an organic semiconductor layer, wherein the organic semiconductor layer is arranged between the at least one photoactive layer and the cathode; and wherein the organic semiconductor layer comprises a compound of formula (1):

[0010]

[0011] wherein

[0012] R 1 to R 5 one of which is a single bond to the 3-position (indicated by "*") of the 2-azaindizine moiety,

[0013] the other of R 1 to R 5 and R 6 to R 9 are independently selected from H, D, substituted or unsubstituted C6 to C 18 aryl, substituted or unsubstituted C3 to C 20 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, C3 to C 16 branched alkyl, C3 to C 16 cycloalkyl, C3 to C 16 branched alkoxy, C3 to C 16 cycloalkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, PX 1 (R 10 )2, F or CN, and / or wherein any two adjacent R 1 to R 9 may be suitably substituted and linked together to form an aromatic or heteroaromatic ring which is unsubstituted or substituted by C6 to C 18 aryl, C3 to C 20 heteroaryl or C1 to C 16 alkyl;

[0014] L is selected from a substituted or unsubstituted C6 to C 24 arylenyl group or a substituted or unsubstituted C2 to C 24 heteroarylenyl group;

[0015] Ar is selected from a substituted or unsubstituted C6 to C 32 aryl group, a substituted or unsubstituted C3 to C 32 heteroaryl group or an unsubstituted or substituted C2 to C6 alkenyl group;

[0016] wherein the substituents of L and Ar are independently selected from:

[0017] H, D, C6 to C 18 aryl, C3 to C20 heteroaryl, C1to C 16 alkyl, C1to C 16 alkoxy, C3to C 16 branched alkyl, C3to C 16 cycloalkyl, C3to C 16 branched alkoxy, C3to C 16 cycloalkoxy, partially or perfluorinated C1to C 16 alkyl, partially or perfluorinated C1to C 16 alkoxy, partially or perdeuterated C1to C 16 alkyl, partially or perdeuterated C1to C 16 alkoxy, F, CN or PX 1 (R 10 )2, wherein the substituents can be linked by single bonds or heteroatoms to form a ring,

[0018] wherein R 10 are independently selected from C6to C 12 aryl, C3to C 12 heteroaryl, C1to C 16 alkyl, C1to C 16 alkoxy, partially or perfluorinated C1to C 16 alkyl, partially or perfluorinated C1to C 16 alkoxy, partially or perdeuterated C1to C 16 alkyl, partially or perdeuterated C1to C 16 alkoxy;

[0019] and X 1 is selected from O, S or Se, preferably O.

[0020] It should be noted that throughout the application and claims, any R n , X n , Ar or L always refers to the same moiety, unless otherwise stated.

[0021] In the present specification, when no definition is otherwise provided, “substituted” means substituted with deuterium, C1to C 12 alkyl and C1to C 12 alkoxy.

[0022] However, in the present specification, “aryl-substituted” means substituted with one or more aryl groups, while the aryl groups themselves can be substituted with one or more aryl and / or heteroaryl groups.

[0023] Correspondingly, in the present specification, “heteroaryl-substituted” means substituted with one or more heteroaryl groups, while the heteroaryl groups themselves can be substituted with one or more aryl and / or heteroaryl groups.

[0024] In the present specification, "alkyl group" means a saturated aliphatic hydrocarbon group. The alkyl group can be a Ci to C 12 alkyl group. More specifically, the alkyl group can be a Ci to C 10 alkyl group or a Ci to C6alkyl group. For example, a Ci to C4alkyl group contains 1 to 4 carbons in the alkyl chain and can be selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl.

[0025] Specific examples of the alkyl group can be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group.

[0026] The term "cycloalkyl" means a saturated hydrocarbon group derived from a cycloalkane by formally separating one hydrogen atom from a ring atom contained in the corresponding cycloalkane. Examples of the cycloalkyl group can be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantyl group, and the like.

[0027] The term "hetero" is understood as at least one carbon atom in a structure that can be formed from covalently bound carbon atoms is replaced by another polyvalent atom. Preferably, the hetero atom is selected from B, Si, N, P, O, S; more preferably from N, P, O, S.

[0028] In the present specification, "aryl group" means a hydrocarbon group that can be produced by formally separating one hydrogen atom from an aromatic ring of a corresponding aromatic hydrocarbon. Aromatic hydrocarbon means a hydrocarbon containing at least one aromatic ring or aromatic ring system. Aromatic ring or aromatic ring system means a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons satisfying Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups comprising multiple aromatic rings connected by single bonds, such as biphenyl, and polycyclic groups comprising fused rings, such as naphthyl or fluorene-2-yl.

[0029] Similarly, under heteroaryl it is especially appropriate to understand as a group derived by formally separating one ring hydrogen from a heterocyclic aromatic ring in a compound comprising at least one heterocyclic aromatic ring.

[0030] Under heterocycloalkyl it is especially appropriate to understand as a group derived by formally separating one ring hydrogen from a saturated cycloalkyl ring in a compound comprising at least one saturated cycloalkyl ring.

[0031] The term "fused aryl ring" or "condensed aryl ring" is understood as two aryl rings that are considered to be fused or condensed when they share at least two common sp 2 hetero atoms.

[0032] In the present specification, a single bond means a direct bond.

[0033] In the context of the present invention, "different" means that the compounds do not have the same chemical structure.

[0034] The terms "free of", "not containing", "not comprising" do not exclude the presence of impurities which can be present in the compounds before deposition. The impurities have no technical effect on the objects to be achieved by the present invention.

[0035] The term "contact sandwich" means a three-layer arrangement in which the middle layer is in direct contact with both adjacent layers.

[0036] The terms "light absorbing layer" and "light absorbing layer" are used synonymously.

[0037] The terms "light emitting layer", "light emitting layer" and "emitting layer" are used synonymously.

[0038] The terms "OLED", "organic light emitting diode" and "organic light emitting device" are used synonymously.

[0039] In the present specification, hole properties mean the ability to supply an electron to form a hole when an electric field is applied, and due to the conduction properties according to the highest occupied molecular orbital (HOMO) level, the holes formed in the anode can easily be injected into the light emitting layer and transported in the light emitting layer.

[0040] In addition, electron properties mean the ability to accept an electron when an electric field is applied, and due to the conduction properties according to the lowest unoccupied molecular orbital (LUMO) level, the electrons formed in the cathode can easily be injected into the light emitting layer and transported in the light emitting layer.

[0041] Advantageous effects

[0042] It was unexpectedly found that the organic electronic device of the present invention solves the problem on which it is based by enabling the device to be superior to the organic electroluminescent devices known in the art in all aspects, in particular in terms of operating voltage and efficiency.

[0043] According to one embodiment of the present invention, the other R 1 to R 5 and R 6 to R 9 the substituents of R 18 aryl, C3 to C 20 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, C3 to C 16 branched alkyl, C3 to C 16 cycloalkyl, C3 to C 16branched alkoxy, C3 to C 16 cycloalkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, PX 1 (R 10 )2, F, or CN.

[0044] According to one embodiment of the present application, the compound of formula (1) has the structure of formula (1a) below:

[0045]

[0046] According to one embodiment of the present application, the organic layer and / or the compound of formula (1) and / or (1a) is non-emissive.

[0047] In the context of the present specification, the term "substantially non-emissive" or "non-emissive" means that the contribution of the compound or layer to the visible light emission spectrum from the device is less than 10%, preferably less than 5% relative to the visible light emission spectrum. The visible light emission spectrum is the emission spectrum at wavelengths of about > 380 nm to about < 780 nm.

[0048] According to one embodiment of the present application, R 1 to R 9 are independently selected from H, -CH=, C1 to C4 alkyl, F, or CN.

[0049] According to one embodiment of the present application, the compound of formula (1) is selected from one of the following formulae (2a) to (2f):

[0050]

[0051]

[0052] wherein R 11 are independently selected from D, C6 to C 18 aryl, C3 to C 20 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, C3 to C 16 branched alkyl, C3 to C 16 cycloalkyl, C3 to C 16 branched alkoxy, C3 to C 16 cycloalkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, PX 1 (R 10 )2, F or CN; and

[0053] n is an integer from 0 to 4.

[0054] According to one embodiment of the present application, the L moiety comprises one or two ring systems which are connected by a single bond.

[0055] According to one embodiment of the present application, the L moiety comprises one to three rings which can be connected by a single bond or are fused.

[0056] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 24 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C2 to C 24 heteroarylenyl group.

[0057] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 18 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C3 to C 12 heteroarylenyl group.

[0058] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 18 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C3 to C 12 heteroarylenyl group.

[0059] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 18 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C3 to C 12 heteroarylenyl group.

[0060] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 18 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C3 to C 12 heteroarylenyl group and does not contain sp 3 -hybridized carbon atoms.

[0061] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6 to C 18 arylenyl group or unsubstituted, alkyl-substituted or aryl-substituted C3 to C 12 heteroarylenyl group and does not contain sp3 - a hybrid carbon atom.

[0062] According to one embodiment of the present application, the L moiety is selected from the group consisting of unsubstituted, alkyl-substituted or aryl-substituted C6to C 14 an arylene group or unsubstituted, alkyl-substituted or aryl-substituted C3to C 12 a heteroarylene group.

[0063] According to one embodiment of the present application, the L moiety is selected from any one of the following E1 to E26 moieties:

[0064]

[0065]

[0066] wherein

[0067] X 2 is selected from O or S, preferably O;

[0068] R 12 and R 13 are independently selected from the group consisting of H, Ci to C 16 alkyl, Ci to C 16 alkoxy, C6to C 18 aryl, C3to C 20 heteroaryl, perfluorinated Ci to C 16 alkyl, perfluorinated Ci to C 16 alkoxy.

[0069] Especially preferred are the E1 to E18 and E21 to E22 moieties, or E1 to E16 and E21 to E22, or E1 to E16, or E1, E2, E5 to E16 and E20.

[0070] According to one embodiment of the present application, the Ar moiety is selected from the group consisting of substituted or unsubstituted C6to C 32 aryl groups, substituted or unsubstituted C3to C 32 heteroaryl groups or substituted C2to C6alkenyl groups.

[0071] According to one embodiment of the present application, the Ar moiety is selected from the group consisting of substituted or unsubstituted C 10 to C 32 aryl groups, substituted or unsubstituted C3to C 32 heteroaryl groups, or unsubstituted or substituted C2to C6alkenyl groups, preferably substituted C2to C6alkenyl groups.

[0072] According to one embodiment of the present application, the Ar moiety is selected from the group consisting of unsubstituted C 10 to C 32an aryl group, an unsubstituted C3to C 32 a heteroaryl group or a substituted C2to C6alkenyl group.

[0073] According to one embodiment of the present application, the Ar moiety comprises zero or one sp 3 -heteroatom, or the Ar moiety does not comprise a sp 3 -heteroatom.

[0074] According to one embodiment of the present application, Ar is selected from the group consisting of a substituted or unsubstituted C6to C 32 aryl group, a substituted or unsubstituted C3to C 32 heteroaryl group or an unsubstituted or substituted C2to C6alkenyl group, wherein the C3to C 32 heteroaryl group comprises one or more N, O or S atoms, or one to three N, O or S atoms, or one to two N, O or S atoms, or one N, O or S atom.

[0075] According to one embodiment of the present application, Ar is selected from the group consisting of a substituted or unsubstituted C6to C 32 aryl group, a substituted or unsubstituted C3to C 32 heteroaryl group or an unsubstituted or substituted C2to C6alkenyl group, wherein the C3to C 32 heteroaryl group comprises one or more O or S atoms, or one O or S atom.

[0076] According to one embodiment of the present application, Ar is selected from the group consisting of a substituted or unsubstituted C6to C 32 aryl group, a substituted or unsubstituted C3to C 32 heteroaryl group or an unsubstituted or substituted C2to C6alkenyl group, wherein the C3to C 32 heteroaryl group comprises one or more N atoms, or one to three N atoms, or one or two N atoms.

[0077] According to one embodiment of the present application, the substituents on Ar are independently selected from the group consisting of: H, D, C6to C 18 aryl, C3to C 20 heteroaryl, C1to C 16 alkyl, C1to C 16 alkoxy, C3to C 16 branched alkyl, C3to C 16 cycloalkyl, C3to C 16 branched alkoxy, C3to C 16 cycloalkoxy, partially or perfluorinated C1to C 16 alkyl, partially or perfluorinated C1to C 16 alkoxy, partially or perdeuterated C1to C16 alkyl, partially or perdeuterated C1to C 16 alkoxy, F, CN, wherein the substituents can be linked by single bonds or heteroatoms to form a ring.

[0078] According to one embodiment of the present application, the substituents of L and Ar are independently selected from the group consisting of: H, D, C6to C 18 aryl, C3to C 20 heteroaryl, C1to C 16 alkyl, C1to C 16 alkoxy, C3to C 16 branched alkyl, C3to C 16 cycloalkyl, C3to C 16 branched alkoxy, C3to C 16 cycloalkoxy, partially or perfluorinated C1to C 16 alkyl, partially or perfluorinated C1to C 16 alkoxy, partially or perdeuterated C1to C 16 alkyl, partially or perdeuterated C1to C 16 alkoxy, F or PX 1 (R 10 )2, wherein the substituents can be linked by single bonds or heteroatoms to form a ring.

[0079] According to one embodiment of the present application, the Ar moiety is a pyrazine group or a substituted or unsubstituted C 12 -C 21 aryl, substituted or unsubstituted heteroaryl group comprising at least three fused rings.

[0080] According to one embodiment of the present application, the Ar moiety is selected from any one of the following D1 to D76 moieties:

[0081]

[0082]

[0083]

[0084]

[0085] wherein

[0086] R 14 , R 15 and R 16 are independently selected from the group consisting of: H, C1to C 16 alkyl, C1to C 16 alkoxy, C6to C 18 aryl, C3to C 20 heteroaryl, perfluorinated C1to C16 alkyl, perfluorinated C1to C 16 alkoxy, wherein R 14 and R 15 may be linked by single bonds or heteroatoms to form a ring.

[0087] According to one embodiment of the present application, the Ar moiety comprises at least three rings, or the Ar moiety comprises three to seven rings, or the Ar moiety comprises three to five rings.

[0088] According to one embodiment of the present application, the Ar moiety is selected from any one of the following D1 to D76 moieties, and in formula D76, R 14 , R 15 and R 16 are independently selected from C1to C 16 alkyl, C1to C 16 alkoxy, C6to C 18 aryl, C3to C 20 heteroaryl, perfluorinated C1to C 16 alkyl, perfluorinated C1to C 16 alkoxy, wherein R 14 and R 15 may be linked by single bonds or heteroatoms to form a ring.

[0089] According to one embodiment of the present application, the Ar moiety does not contain a styryl, fluorenyl and / or carbazolyl group.

[0090] According to one embodiment of the present application, the compound of formula (1) contains zero or one carbazolyl group, or the compound of formula (1) does not contain a carbazolyl group.

[0091] According to one embodiment of the present application, the compound of formula (1) does not contain the following structure:

[0092]

[0093] Additionally and / or alternatively, according to one embodiment of the present application, the compound of formula (1) does not contain the following structure:

[0094]

[0095] According to one embodiment of the present application, the compound of formula (1) is selected from the group consisting of compounds A1 to A37:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] Redox n-type dopant

[0102] According to one embodiment of the present application, the organic semiconductor layer of the organic electronic device comprises a redox n-dopant.

[0103] Preferably, the organic semiconductor layer comprising the compound of formula (1) and a redox n-dopant is non-emissive.

[0104] By redox n-dopant, it is understood a compound which, if embedded into an electron transporting matrix, improves the electronic properties of the formed organic material, in particular in terms of electron injection, electron generation and / or electronic conductivity, compared to the pure matrix under the same physical conditions. Preferably, the redox n-dopant is non-emissive.

[0105] In the context of the present application, "embedded into an electron transporting matrix" means that the redox n-dopant forms a mixture with the electron transporting matrix.

[0106] The redox n-dopant can be selected from the group consisting of elemental metals, metal salts, metal complexes and organic groups.

[0107] For use in consumer electronics, only metals containing stable nuclides or nuclides with a long half-life of radioactive decay can be suitable. As a level of acceptable nuclear stability, the nuclear stability of natural potassium can be utilized.

[0108] In the context of the present application, metals are understood to be in elemental form, metal alloys, or in the state of free atoms or metal clusters. It is understood that metals deposited by vacuum thermal evaporation can be evaporated from the metallic phase, e.g. from pure bulk metal, in their elemental form.

[0109] It is further understood that if the evaporated elemental metal is deposited together with a covalent matrix, the metal atoms and / or clusters are embedded into the covalent matrix. In other words, it is understood that any metal-doped covalent material prepared by vacuum thermal evaporation contains at least partially the metal in its elemental form.

[0110] According to one embodiment of the present application, the organic semiconductor layer of the organic electronic device comprises a metal, preferably selected from alkali metals, alkaline earth metals, rare earth metals, and first transition period metals Ti, V, Cr and Mn, in particular 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.

[0111] In one embodiment, the redox n-type dopant is selected from alkali metal salts and alkali metal complexes; preferably from lithium salts and lithium organic complexes; more preferably from lithium halides and lithium organic chelates; even more preferably from lithium fluoride, lithium hydroxyquinolinate, lithium borate, lithium phenolate, lithium hydroxypyridinate or from lithium complexes with Schiff base ligands; most preferably,

[0112] - the lithium complex is of formula II, III or IV:

[0113]

[0114] wherein

[0115] A1to A6are the same or independently selected from CH, CR, N, O;

[0116] R is the same or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl with 1 to 20 carbon atoms; and more preferred A1to A6are CH,

[0117] - the borate organic ligand is tetrakis(1H-pyrazol-1-yl)borate,

[0118] - the phenolate is 2-(pyridin-2-yl)phenolate, 2-(diphenylphosphoryl)phenolate, imidazolyl phenolate, 2-(pyridin-2-yl)phenolate, or 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenolate,

[0119] - the hydroxypyridine salt is 2-(diphenylphosphoryl)pyridin-3-ol salt,

[0120] the lithium Schiff base has the structure 100, 101, 102 or 103:

[0121]

[0122] According to one embodiment of the present application, the organic semiconductor layer of the present application comprises a lithium organic complex, or LiQ.

[0123] According to one embodiment of the present application, the organic semiconductor layer of the present application is an electron transport layer, an electron injection layer or a charge generation layer; or an electron transport layer or a charge generation layer.

[0124] According to one embodiment of the present application, the at least one photoactive layer is an emitting layer.

[0125] According to one embodiment of the present application, the organic electronic device comprises a first and a second emitting layer, wherein the organic semiconducting layer is arranged between the first and the second emitting layer.

[0126] According to one embodiment of the present application, the organic electronic device comprises a first, a second and a third emitting layer, wherein the organic semiconducting layer is arranged between the first and the second emitting layer and / or between the second and the third emitting layer.

[0127] According to one embodiment of the present application, the organic semiconducting layer is a charge generating layer, or an n-type charge generating layer.

[0128] According to one embodiment of the present application, the organic electronic device is an electroluminescent device, preferably an organic light emitting diode.

[0129] The present application also relates to a display device comprising an organic electronic device comprising according to the present application.

[0130] The present application also relates to a compound of formula (1), Ar is selected from a substituted or unsubstituted C 12 to C 32 aryl group, a substituted or unsubstituted C3to C 32 heteroaryl group or an unsubstituted or substituted C2-C6 alkenyl group, and excludes the following compounds,

[0131]

[0132] Any of the above mentioned explanations for formula (1) apply by analogy in the context of an organic electronic device.

[0133] Further layers

[0134] According to the present application, the organic electronic device can comprise further layers in addition to the layers already mentioned above. Exemplary embodiments of the individual layers are described below:

[0135] Substrate

[0136] The substrate can be any substrate commonly used in the fabrication of electronic devices, e.g. organic light emitting diodes. If light is to be emitted through the substrate, the substrate should be a transparent or semi-transparent material, e.g. a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be a transparent or a non-transparent material, e.g. a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.

[0137] Anode electrode

[0138] The first electrode or the second electrode included in the organic electronic device of the present application can be an anode electrode. The anode electrode can be formed by depositing or sputtering a material used to form the anode electrode. The material used to form the anode electrode can be a high work function material in order to facilitate hole injection. The anode material can also be selected from a low work function material (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (Sn02), aluminum zinc oxide (AlZO), and zinc oxide (ZnO), can be used to form the anode electrode. Metals, typically silver (Ag), gold (Au), or metal alloys, can also be used to form the anode electrode.

[0139] Hole injection layer

[0140] The hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like. When vacuum deposition is used to form the HIL, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. Generally, however, the conditions for vacuum deposition can include a deposition temperature of 100°C to 500°C, a pressure of 10 -8 to 10 -3 torr (1 torr is equal to 133.322 Pa), and a deposition rate of 0.1 nm / sec to 10 nm / sec.

[0141] When spin coating or printing is used to form the HIL, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the coating conditions can include a coating speed of about 2000 rpm to about 5000 rpm, and a heat treatment temperature of about 80°C to about 200°C. After the coating is performed, heat treatment removes the solvent.

[0142] The HIL can be formed from any compound typically used to form a HIL. Examples of compounds that can be used to form the HIL include: phthalocyanine compounds, such as copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), and polyaniline) / poly(4-styrenesulfonate (PANI / PSS).

[0143] The HIL can include or consist of a p-type dopant, which can be selected from the group consisting of tetrafluoro-tetracyanoquinodimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile, or 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile), but is not limited thereto. The HIL can be selected from a hole transport matrix compound doped with a p-type dopant. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc) having a HOMO level of about -5.2 eV, doped with tetrafluoro-tetracyanoquinodimethane (F4TCNQ) having a LUMO level of about -5.2 eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2 eV) doped with F4TCNQ; α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-phenylamine) doped with F4TCNQ; α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile. The concentration of the p-type dopant can be selected from the range of 1 wt% to 20 wt%, more preferably from the range of 3 wt% to 10 wt%.

[0144] The thickness of the HIL can be in the range of about 1 nm to about 100 nm, for example, about 1 nm to about 25 nm. When the thickness of the HIL is in this range, the HIL can have excellent hole injection properties without causing substantial damage to the driving voltage.

[0145] Hole transport layer

[0146] The hole transport layer (HIL) can be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the conditions of deposition and coating can be similar to those used to form the HIL. However, the conditions of vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0147] The HTL can be formed from any compound typically used to form an 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 herein by reference. Examples of compounds that can be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; phenylenediamine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthalen-1 -yl)-N,N'-diphenylphenylenediamine (a-NPD); and triphenylamine-based compounds, such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and suppress exciton diffusion into the EML.

[0148] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further preferably about 20 nm to about 190 nm, further preferably about 40 nm to about 180 nm, further preferably about 60 nm to about 170 nm, further preferably about 80 nm to about 160 nm, further preferably about 100 nm to about 160 nm, further preferably about 120 nm to about 140 nm. A preferred thickness of the HTL can be 170 nm to 200 nm.

[0149] When the thickness of the HTL is in this range, the HTL can have excellent hole transport properties without significantly reducing the driving voltage.

[0150] Electron blocking layer

[0151] The function of the electron blocking layer (EBL) is to prevent the transfer of electrons from the light-emitting layer to the hole-transporting layer, thereby confining the electrons in the light-emitting layer. As a result, the efficiency, operating voltage, and / or lifetime are improved. Typically, the electron blocking layer comprises a triarylamine compound. The triarylamine compound can have a LUMO energy level closer to the vacuum level compared to the LUMO energy level of the hole-transporting layer. The electron blocking layer can have a HOMO energy level further away from the vacuum level compared to the HOMO energy level of the hole-transporting layer. The thickness of the electron blocking layer can be chosen between 2 and 20 nm.

[0152] If the triplet energy level of the electron blocking layer is high, it can also be referred to as a triplet control layer.

[0153] If a phosphorescent green or blue light-emitting layer is used, the function of the triplet control layer is to reduce quenching of triplets. Thus, higher light-emitting efficiency from the phosphorescent light-emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds having a triplet energy level higher than that of the phosphorescent emitter in the adjacent light-emitting layer. Suitable compounds, in particular triarylamine compounds, for the triplet control layer are described in EP 2 722 908 Al.

[0154] Photoactive layer (PAL)

[0155] The photoactive layer converts current to photons or photons to current.

[0156] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. When the PAL is formed using vacuum deposition or spin coating, the conditions of deposition and coating can be similar to those used for forming the HIL. However, the conditions of deposition and coating can vary depending on the compound used to form the PAL.

[0157] It can be provided that the photoactive layer does not contain the compound of the formula (1).

[0158] The photoactive layer can be a light-emitting layer or a light-absorbing layer.

[0159] Light-emitting layer (EML)

[0160] The EML can be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the conditions of deposition and coating can be similar to those used for forming the HIL. However, the conditions of deposition and coating can vary depending on the compound used to form the EML.

[0161] It can be provided that the light-emitting layer does not contain the compound of the formula (I).

[0162] The light-emitting layer (EML) can be formed from a combination of a host and an emitter dopant. Examples of hosts are: AIq3, 4,4'-N,N'-dicarbazole biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), diphenylstyrylarylidene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0163] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit 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.

[0164] Examples of red emitter dopants are PtOEP, Ir(piq)3 and Btp2lr(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0165] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0166] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd), Ir(dfppz)3 and trifluorene. Examples of fluorescent blue emitter dopants are 4,4′-bis(4-diphenylaminophenyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0167] The amount of the luminophore dopant can be in a range of about 0.01 to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, the luminescent layer can be composed of a luminescent polymer. The thickness of the EML can be in a range of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can have excellent luminescence without substantially compromising the driving voltage.

[0168] Hole blocking layer (HBL)

[0169] A hole blocking layer (HBL) can be formed on the EML by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. to prevent holes from diffusing into the ETL. When the EML contains a phosphorescent dopant, the HBL may also have a triplet exciton blocking function. The hole blocking layer may be an organic semiconductor layer of the present invention, which contains or consists of a compound of the present invention represented by general formula (1) as defined above.

[0170] HBL may also be called auxiliary ETL or a-ETL.

[0171] When the HBL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those used to form the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL may be used. Examples of compounds used to form the HBL include Oxadiazole derivatives, triazine derivatives and phenanthroline derivatives.

[0172] The thickness of the HBL can be in the range of about 5 nm to about 100 nm, for example, in the range of about 10 nm to about 30 nm. When the thickness of the HBL is in this range, the HBL can have excellent hole-blocking properties without causing substantial damage to the driving voltage.

[0173] The hole-blocking layer can also be described as a-ETL or auxiliary ETL.

[0174] According to one embodiment, the hole-blocking layer is disposed between the at least one photoactive layer and the organic semiconducting layer comprising the compound of formula (1).

[0175] According to one embodiment, the hole-blocking layer is disposed between the at least one photoactive layer and the organic semiconducting layer comprising the compound of formula (1), wherein the organic semiconducting layer comprising the compound of formula (1) further comprises a redox n-type dopant.

[0176] According to one embodiment, the hole-blocking layer is disposed between the at least one photoactive layer and the organic semiconducting layer comprising the compound of formula (1), wherein the organic semiconducting layer comprising the compound of formula (1) further comprises a metal or metal organic complex, or a metal or lithium organic complex.

[0177] According to one embodiment, the hole-blocking layer is disposed between the at least one photoactive layer and the organic semiconducting layer comprising the compound of formula (1), wherein the organic semiconducting layer comprising the compound of formula (1) further comprises a metal.

[0178] Electron transport layer (ETL)

[0179] The OLED of the present application can comprise an electron transport layer (ETL). According to one preferred embodiment of the present application, the electron transport layer can be the inventive organic semiconducting layer comprising the inventive compound represented by general formula (1) as defined above.

[0180] According to various embodiments, the OLED can comprise an electron transport layer or an electron transport layer stack, the stack comprising at least one first electron transport layer and at least one second electron transport layer.

[0181] By properly adjusting the energy level of a specific ETL layer, the injection and transport of electrons can be controlled, and holes can be effectively blocked. Thus, the OLED can have a long lifetime.

[0182] The electron transport layer of the organic electronic device can comprise the compound represented by general formula (1) as defined above as an organic electron transport matrix (ETM) material. In addition to, or instead of, the compound represented by general formula (1), the electron transport layer can comprise further ETM materials known in the art. Likewise, the electron transport layer can comprise the compound represented by general formula (1) as the only electron transport matrix material. If the organic electronic device of the present application comprises more than one electron transport layer, the compound represented by general formula (1) can be comprised in only one electron transport layer, in more than one electron transport layer, or in all electron transport layers. According to the present application, the electron transport layer can comprise at least one additive as defined below in addition to the ETM material.

[0183] Furthermore, the electron transport layer can comprise one or more n-type dopants. The additive can be an n-type dopant. The additive can be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In another embodiment, the metal can be one selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In another embodiment, the n-type dopant can be one selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. In one embodiment, the alkali metal compound can be lithium 8-hydroxyquinolinate (LiQ), lithium tetra(1 H-pyrazol-1 -yl)borate, or lithium 2-(diphenylphosphoryl)phenolate. Compounds suitable for ETM (compounds which can also be used in addition to the compounds of the present application represented by general formula (I) as defined above) are not particularly limited. In one embodiment, the electron transport matrix compound consists of covalently bound atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably at least 10 delocalized electrons. In one embodiment, the conjugated system of delocalized electrons can be comprised in an aromatic or heteroaromatic structural moiety, as disclosed for example in documents EP 1970 371 A1 or WO 2013 / 079217 A1.

[0184] Electron injection layer (EIL)

[0185] An optional EIL that can facilitate injection of electrons from the cathode can be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg, all of which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions can vary depending on the material used to form the EIL. The EIL can be an organic semiconductor layer comprising the compound of formula (1).

[0186] The thickness of the EIL can be in the range of about 0.1 nm to about 10 nm, for example, in the range of about 0.5 nm to about 9 nm. When the thickness of the EIL is in this range, the EIL can have satisfactory electron-injection properties without causing substantial damage to the driving voltage.

[0187] Cathode electrode

[0188] The cathode electrode is formed on the EIL, if the EIL is present. The cathode electrode can be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode electrode can be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like. Alternatively, the cathode electrode can be formed of a transparent conductive oxide such as ITO or IZO.

[0189] The thickness of the cathode electrode can be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode can be transparent or semi-transparent even if formed of a metal or a metal alloy.

[0190] It is to be understood that the cathode electrode is not part of the electron injection layer or the electron transport layer.

[0191] Charge generation layer / hole generation layer

[0192] The charge generation layer (CGL) can include a p-type layer and an n-type layer. An intermediate layer can be disposed between the p-type layer and the n-type layer.

[0193] In general, the charge generation layer is a pn junction that connects the n-type charge generation layer (electron generation layer) and the hole generation layer. The n-side of the pn junction generates electrons and injects them into the layer adjacent in the direction of the anode. Similarly, the p-side of the pn junction generates holes and injects them into the layer adjacent in the direction of the cathode.

[0194] The charge generation layer is used in tandem and stacked devices, for example, in tandem or stacked OLEDs comprising two or more light-emitting layers between two electrodes. In a tandem or stacked OLED comprising two light-emitting layers, the n-type charge generation layer provides electrons to a first light-emitting layer disposed near the anode, while the hole generation layer provides holes to a second light-emitting layer disposed between the first light-emitting layer and the cathode.

[0195] Suitable host materials for the hole generation layer can be materials conventionally used as hole injection and / or hole transport host materials. The p-type dopant for the hole generation layer can also employ conventional materials. For example, the p-type dopant can be one selected from the group consisting of tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivatives, fulvalene derivatives, iodine, FeCl3, FeF3, and SbCl5. In addition, the host can be one selected from the group consisting of N,N'-di(naphthalen-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB). The p-type charge generation layer can consist of CNHAT.

[0196] The n-type charge generation layer can be a layer comprising the compound of formula (1). The n-type charge generation layer can be a layer of pure n-type dopant, for example, a metal, or can consist of an organic host material doped with an n-type dopant. In one embodiment, the n-type dopant can be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In another embodiment, the metal can be one selected from the 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 the group consisting of Li, Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. Suitable host materials for the electron generation layer can be materials conventionally used as host materials for electron injection or electron transport layers. The host material can be, for example, one selected from the group consisting of triazine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminum, benzoxazole derivatives, and silacyclophane derivatives.

[0197] The hole generation layer is disposed in direct contact with the n-type charge generation layer.

[0198] According to one aspect of the present invention, the organic semiconductor layer is disposed between the first and second light-emitting layers and further comprises a redox n-type dopant.

[0199] According to one aspect of the present application, the organic semiconductor layer is arranged between the first and the second light-emitting layer and further comprises a metal.

[0200] According to one aspect of the present application, the organic semiconductor layer is arranged between the first and the second light-emitting layer and further comprises a metal selected from the group consisting of alkali metals, alkaline earth metals and rare earth metals.

[0201] According to one aspect of the present application, the organic semiconductor layer comprising a compound of formula (1) is arranged between the first and the second light-emitting layer, and a further organic semiconductor layer comprising a compound of formula (1) is arranged between the second light-emitting layer and the cathode.

[0202] According to one aspect of the present application, the organic semiconductor layer comprising a compound of formula (1) is arranged between the first and the second light-emitting layer, and a further organic semiconductor layer comprising a compound of formula (1) is arranged between the second light-emitting layer and the cathode; wherein the organic semiconductor layer comprising a compound of formula (1) further comprises a redox n-type dopant.

[0203] According to one aspect of the present application, the organic semiconductor layer comprising a compound of formula (1) is arranged between the first and the second light-emitting layer, and a further organic semiconductor layer comprising a compound of formula (1) is arranged between the second light-emitting layer and the cathode; wherein the further organic semiconductor layer comprising a compound of formula (1) further comprises a redox n-type dopant.

[0204] According to one aspect of the present application, the organic semiconductor layer comprising a compound of formula (1) is arranged between the first and the second light-emitting layer, and a further organic semiconductor layer comprising a compound of formula (1) is arranged between the second light-emitting layer and the cathode; wherein the organic semiconductor layer comprising a compound of formula (1) further comprises a redox n-type dopant, and the further organic semiconductor layer comprising a compound of formula (1) further comprises a redox n-type dopant.

[0205] According to one aspect of the present application, the organic semiconductor layer comprising a compound of formula (1) is arranged between the first and the second light-emitting layer, and a further organic semiconductor layer comprising a compound of formula (1) is arranged between the second light-emitting layer and the cathode; wherein the organic semiconductor layer comprising a compound of formula (1) further comprises a metal, and the further organic semiconductor layer comprising a compound of formula (1) further comprises a redox n-type dopant.

[0206] Organic light emitting diode (OLED)

[0207] The organic electronic device of the present application can be an organic light emitting device.

[0208] According to one aspect of the present application, there is provided an organic light emitting diode (OLED) comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, a light emitting layer, an organic semiconductor layer comprising a compound of formula (1), and a cathode electrode.

[0209] According to another aspect of the present application, there is provided an OLED comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an organic semiconductor layer comprising a compound of formula (1), and a cathode electrode.

[0210] According to another aspect of the present application, there is provided an OLED comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an organic semiconductor layer comprising a compound of formula (1), an electron injection layer, and a cathode electrode.

[0211] According to various embodiments of the present application, an OLED in which layers are arranged between the above-mentioned layers, on the substrate, or on the top electrode can be provided.

[0212] According to one aspect, the OLED can comprise a layer structure in which the substrate is arranged adjacent to an anode electrode, the anode electrode is arranged adjacent to a first hole injection layer, the first hole injection layer is arranged adjacent to a first hole transport layer, the first hole transport layer is arranged adjacent to a first electron blocking layer, the first electron blocking layer is arranged adjacent to a first light emitting layer, the first light emitting layer is arranged adjacent to a first electron transport layer, the first electron transport layer is arranged adjacent to an n-type charge generation layer, the n-type charge generation layer is arranged adjacent to a hole generation layer, the hole generation layer is arranged adjacent to a second hole transport layer, the second hole transport layer is arranged adjacent to a second electron blocking layer, the second electron blocking layer is arranged adjacent to a second light emitting layer, and an optional electron transport layer and / or an optional injection layer is arranged between the second light emitting layer and a cathode electrode.

[0213] The organic semiconductor layer of the present application can be an electron transport layer, a first electron transport layer, an n-type charge generation layer, and / or a second electron transport layer.

[0214] For example, Figure 2 The OLED of formula (1) can be formed by a method in which, on a substrate (110), an anode (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), a light emitting layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180), and a cathode electrode (190) are sequentially formed in this order.

[0215] Organic electronic device

[0216] The organic electronic device of the present application can be a light-emitting device, or a photovoltaic cell, preferably a light-emitting device.

[0217] According to another aspect of the present application, there is provided a method of manufacturing an organic electronic device, said method using:

[0218] at least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0219] Suitable deposition methods include:

[0220] deposition by vacuum thermal evaporation;

[0221] deposition by solution processing, preferably said processing is selected from spin-coating, printing, casting; and / or

[0222] slot-die coating.

[0223] According to various embodiments of the present application, there is provided a method, said method using:

[0224] a first deposition source for releasing a compound of formula (1) of the present application, and

[0225] a second deposition source for releasing said metal, metal salt or alkali or alkaline earth metal complex; or organic alkali or alkaline earth metal complex; or lithium quinolate;

[0226] said method comprising the step of forming an organic semiconducting layer; thereby for an organic light-emitting diode (OLED):

[0227] the organic semiconducting layer is formed by releasing from said first deposition source a compound of formula (1) of the present application, and releasing from said second deposition source a metal, metal salt or alkali or alkaline earth metal complex; or organic alkali or alkaline earth metal complex; or lithium quinolate.

[0228] According to various embodiments of the present application, said method can further comprise forming a light-emitting layer on the anode electrode and at least one layer selected from forming a hole injection layer between the anode electrode and the first electron transport layer, forming a hole transport layer or forming a hole blocking layer.

[0229] According to various embodiments of the present application, said method can further comprise the step of forming an organic light-emitting diode (OLED), wherein

[0230] forming a first anode electrode on a substrate,

[0231] forming a light-emitting layer on said first anode electrode,

[0232] - forming an electron transport layer stack on said light emitting layer, optionally forming a hole blocking layer on said light emitting layer, and forming an organic semiconductor layer,

[0233] - finally forming a cathode electrode,

[0234] - optionally forming a hole injection layer, a hole transport layer and a hole blocking layer in this order between said first anode electrode and said light emitting layer,

[0235] - optionally forming an electron injection layer between said organic semiconductor layer and said cathode electrode.

[0236] According to various embodiments of the OLED according to the present application, the OLED can not comprise an electron injection layer.

[0237] According to various embodiments, the OLED can have the following layer structure, wherein the layers have the following order:

[0238] anode, hole injection layer, first hole transport layer, second hole transport layer, light emitting layer, optional hole blocking layer, organic semiconductor layer comprising a compound of formula (1) according to the present application, optional electron injection layer, and cathode.

[0239] According to another aspect of the present application, an electronic device comprising at least one organic light emitting device according to any of the embodiments described throughout the present application is provided, preferably the electronic device comprises an organic light emitting diode according to one of the embodiments described throughout the present application. More preferably, the electronic device is a display device.

[0240] In one embodiment, the organic electronic device according to the present application comprising an organic semiconductor layer comprising a compound of formula (I) can further comprise a layer comprising an axi compound and / or a quinonedimethane compound.

[0241] In one embodiment, the axi compound and / or the quinonedimethane compound can be substituted by one or more halogen atoms and / or by one or more electron withdrawing groups. The electron withdrawing group can be selected from a nitrile group, a halogenated alkyl group, or from a perhalogenated alkyl group, or from a perfluorinated alkyl group. Other examples of electron withdrawing groups can be acyl, sulfonyl or phosphoryl groups.

[0242] Alternatively, the acyl group, sulfonyl group and / or phosphoryl group can comprise a halogenated and / or perhalogenated hydrocarbyl group. In one embodiment, the perhalogenated hydrocarbyl group can be a perfluorinated hydrocarbyl group. Examples of perfluorinated hydrocarbyl groups can be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, perfluoromethylphenyl; examples of sulfonyl groups comprising halogenated hydrocarbyl groups can be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, and the like.

[0243] In one embodiment, the fulvene and / or quinodimethane compound can be comprised in a hole injection, hole transport and / or hole generating layer.

[0244] In one embodiment, the fulvene compound can have formula (XX) and / or the quinodimethane compound can have formula (XXIa) or (XXIb):

[0245]

[0246] wherein (as an exception to the above description) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 15 , R 16 , R 20 , R 21 are independently selected from the above electron withdrawing groups, and R 9 , R 10 , R 13 , R 14 , R 17 , R 18 , R 19 , R 22 , R 23 and R 24 are independently selected from H, halogen and the above electron withdrawing groups.

[0247] According to one embodiment of the present application, the organic semiconducting layer comprising a compound of formula (1) is adjacent to a layer comprising a compound of formula (XX), (XXIa) or (XXIb).

[0248] According to one embodiment of the present application, the organic semiconducting layer comprising a compound of formula (1) is in direct contact with a layer comprising a compound of formula (XX), (XXIa) or (XXIb).

[0249] Hereinafter, the embodiments will be described 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 exemplary aspects. BRIEF DESCRIPTION OF THE DRAWINGS

[0250] The aforementioned components in the described embodiments, as well as the claimed components and components used in the present invention, do not have any special exceptions in terms of their size, shape, material selection and technical concept, so the selection criteria known in the relevant field can be applied without restriction.

[0251] Additional details, features, and advantages of the present invention are disclosed in the dependent claims and the following description of the accompanying drawings, which show, by way of example, preferred embodiments of the invention. However, any embodiment does not necessarily represent the full scope of the invention, and reference should be made to the claims and this text for interpretation of the scope of the invention. It should 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 invention as claimed.

[0252] Figure 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0253] Figure 2 is a schematic cross-sectional view of an organic light emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0254] Figure 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0255] Figure 4 is a schematic cross-sectional view of an OLED including a charge generation layer and two light-emitting layers according to an exemplary embodiment of the present invention.

[0256] Hereinafter, the accompanying drawings will be described in more detail with reference to embodiments. However, the present disclosure is not limited to the following drawings.

[0257] As used herein, when a first element is referred to as being formed or disposed “on” or “over” a second element, the first element may be disposed directly on the second element, or one or more other elements may be disposed therebetween. When a first element is referred to as being “formed or disposed directly on” or “formed or disposed directly onto” a second element, there are no other elements therebetween.

[0258] Figure 1is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present application. The organic electronic device 100 comprises a substrate 110, an anode 120, a photoactive layer (PAL) 125, an organic semiconductor layer 160 comprising a compound of formula (1). The organic semiconductor layer 160 comprising a compound of formula (1) is formed on the PAL 125. On the organic semiconductor layer 160, a cathode 190 is provided.

[0259] Figure 2 is a schematic cross-sectional view of an organic light emitting diode (OLED) 100 according to an exemplary embodiment of the present application. The OLED 100 comprises 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. An electron injection layer (EIL) 180 is provided on the electron transport layer (ETL) 160. A cathode 190 is provided directly on the electron injection layer (EIL) 180.

[0260] Optionally, an electron transport layer stack (ETL) can be used instead of a single electron transport layer 160.

[0261] Figure 3 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present application. Figure 3 Differing from Figure 2 , the OLED 100 of Figure 3 comprises an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155.

[0262] Referring to Figure 3 , the OLED 100 comprises a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode electrode 190.

[0263] Preferably, the organic semiconductor layer comprising a compound of formula (1) can be an ETL.

[0264] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present application. Figure 4 Differing from Figure 3 , the OLED 100 of Figure 4 further comprises a charge generation layer (CGL) and a second emission layer (151).

[0265] Referring toFigure 4 The OLED 100 includes: a substrate 110, an anode 120, a first hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emission layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (n-type CGL) 185, a hole generation 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 (HBL) 156, a second electron transport layer (ETL) 161, a second electron injection layer (EIL) 181, and a cathode 190.

[0266] Preferably, the organic semiconductor layer comprising the compound of formula (1) can be the n-type CGL.

[0267] Preferably, the organic semiconductor layer comprising the compound of formula (1) can be the first ETL, the n-type CGL, and / or the second ETL.

[0268] Although not shown in Figure 1 , Figure 2 , Figure 3 and Figure 4 , a sealing layer can also be formed on the cathode electrode 190 to seal the OLED 100. In addition, various other modifications can be made thereto.

[0269] Hereinafter, the embodiments will be explained in more detail with reference to examples. However, the present disclosure is not limited to the following examples. DETAILED DESCRIPTION

[0270] The present application is further illustrated by the following examples, which are merely illustrative and not limiting.

[0271] The preparation of several compounds of the present application is shown below, using the following general methods:

[0272] General Method:

[0273] A flask was flushed with nitrogen and charged with two starting materials (see Table 1) in a 1 : 1 ratio. An organic solvent was added and the mixture was degassed. A base and water were charged to a second flask and degassed likewise. The aqueous base was added to the starting materials under nitrogen and the reaction was started by adding a catalyst. The reaction mixture was heated to the given temperature until TLC showed complete conversion. The mixture was then cooled to room temperature and the product was purified according to the method given in Table 2:

[0274] Table 1: Starting materials for reactions according to the general method:

[0275]

[0276]

[0277]

[0278] Table 2: Reaction conditions for the reactions of General Procedure A

[0279]

[0280]

[0281] Compound A1 was synthesized as follows:

[0282] The flask was flushed with nitrogen and charged with aldehyde A1-A (structure below) and bis(2-pyridyl)ketone in a 1 : 1 ratio.

[0283]

[0284] 0.1 eq iodine, 2 eq ammonium acetate and THF / EtOH 1 / 1 were added and the mixture was heated to reflux until TLC showed complete consumption of starting material. The mixture was then cooled to room temperature and the product was purified by removal of the solvent followed by aqueous workup (CHCI3 / Na2S203 / H20), precipitation from CHCI3 / n-hexane, collection of the solid, dissolution in hot chlorobenzene, filtration through Si02and precipitation by addition of n-hexane. Yield 3.7 g (19%), m / z = 549 [M+H] + .

[0285] Compound A29 was synthesized as follows:

[0286] The flask was flushed with nitrogen and charged with aldehyde A29-A (structure below) and bis(pyridin-2-yl)methanone in a 1 : 1 ratio.

[0287]

[0288] 0.1 eq iodine, 8.8 eq ammonium acetate and THF / EtOH 1 / 1 were added and the mixture was heated to reflux until TLC showed complete consumption of starting material. The mixture was then cooled to room temperature and diluted with MeOH and 2M NaOH. The product was filtered off and recrystallized from toluene. Yield 3.3 g (52%), m / z = 541 [M+H] + .

[0289] General procedure for OLED fabrication

[0290] For bottom-emitting devices, see Examples 1 to 9 and Comparative Example 1 in Table 3, a 15 Ω / cm2ITO with 90 nm ITO was used 2 Glass substrates (available from Corning Inc.) were cut to a size of 50 mm x 50 mm x 0.7 mm, ultrasonically washed with isopropanol for 5 minutes, then ultrasonically washed with pure water for 5 minutes, and then washed with UV ozone for 30 minutes to prepare anodes.

[0291] Then, 97 vol% of Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H- carbazol-3-yl)phenyl]amine (CAS 1242056-42-3) and 3 vol% of 2,2',2"-(cyclopropane- 1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) were vacuum deposited on the anode to form a HIL with a thickness of 10 nm.

[0292] Then, Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]amine was vacuum deposited on the HIL to form a HTL with a thickness of 118 nm.

[0293] Then, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine (CAS 1198399-61-9) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0294] Then, 97 vol% H09 (Sun Fine Chemicals, South Korea) as EML host and 3 vol% BD200 (Sun Fine Chemicals, South Korea) as fluorescent blue dopant were deposited on the EBL to form a blue-emitting EML with a thickness of 20 nm.

[0295] Then, a first hole blocking layer with a thickness of 5 nm was formed by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the emitting layer.

[0296] Then, an electron transport layer with a thickness of 25 nm was formed by depositing 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl))naphthalen-1-yl)-[1,1'-biphenyl]-4- carbonitrile on the hole blocking layer. The electron transport layer (ETL) comprises 50 wt% of the matrix compound and 50 wt% of LiQ.

[0297] Then a n-CGL with a thickness of 15 nm is formed on the ETL. The composition of the n-CGL can be taken from Table 2.

[0298] Then, a p-CGL with a thickness of 10 nm is formed on the n-CGL by depositing Diphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine (CAS 1242056-42-3) together with 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) on the n-CGL.

[0299] Then, a second HTL with a thickness of 10 nm is formed on the p-CGL by vacuum deposition of Diphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine on the p-CGL.

[0300] At 10 -7 mbar, Al is evaporated at a rate of 0.01 to 10 nm / min to form a cathode with a thickness of 100 nm.

[0301] The device is protected against environmental conditions by encapsulating the OLED stack with a glass slide. A cavity is formed, which contains a getter material for further protection.

[0302] To evaluate the performance of the embodiments of the present application compared to the prior art, the current efficiency is measured at 20°C. The current-voltage characteristics are determined by providing a voltage in V and measuring the current in mA flowing through the device under test using a Keithley 2635 source measurement unit. The voltage applied to the device is varied in a range between 0 V and 10 V in steps of 0.1 V. Likewise, the luminance in cd / m 2 2 at each voltage value is measured by using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) to determine the luminance-voltage characteristics and CIE coordinates. The cd / A efficiency at 10 mA / cm 2 2 is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[0303] The lifetime LT of the device is measured at ambient conditions (20°C) and 30 mA / cm 2 2 using a Keithley 2400 source meter and is reported in hours.

[0304] The luminance of the device is measured with a calibrated photodiode. The lifetime LT is defined as the time until the luminance of the device has dropped to 97% of its initial value.

[0305] Technical effects of the invention

[0306] To investigate the utility of the compounds of the present application, preferred materials were tested in model top-emitting blue OLEDs prepared as described above.

[0307] As comparative examples, the following compounds were used:

[0308]

[0309] In the following, several embodiments according to the present application were prepared and their properties were juxtaposed with those of the devices of the comparative examples. The results are shown in Table 3 below:

[0310] Table 3: Properties of several organic electronic devices

[0311]

[0312]

[0313] The results show that the compounds of the present application exhibit significantly enhanced performance compared to the prior art documents, especially in terms of efficiency and EQE.

[0314] The specific combinations of elements and features in the above detailed description are not to be understood as exhaustive; other teachings herein and in the patents / applications incorporated by reference are expressly contemplated as alternatives and substitutions to the above. Variations, modifications, and other implementations of what is described herein can occur to those of ordinary skill in the art without departing from the spirit and the scope of the claimed application. Accordingly, the foregoing description is by way of example only, and is not intended as limiting. The use of the term "including" as well as other forms for "including", such as "includes" and "included", is not limiting. Also, the use of the term "comprising" as well as other forms for "comprising", such as "comprise" and "comprises", is not limiting. The use of the term "a" followed by a noun is not limiting. The use of the terms "one" and "the" followed by a noun is not limiting. The use of the term "plurality" followed by a noun is not limiting. The use of the term "another" is not limiting. The use of the term "at least one" is not limiting. The use of the term "or" is both inclusive and exclusive unless explicitly indicated otherwise. The use of the term "and" is both inclusive and exclusive unless explicitly indicated otherwise. The use of the term "exemplary" is not limiting. The use of the term "comprising" is not limiting. The use of the term "comprise" is not limiting. The use of the term "comprises" is not limiting. The use of the term "comprised" is not limiting. The use of the term "comprised of" is not limiting. The use of the term "comprised with" is not limiting. The use of the term "consisting of" is not limiting. The use of the term "consisting" is not limiting. The use of the term "consisting in" is not limiting. The use of the term "consisting with" is not limiting. The use of the term "consists" is not limiting. The use of the term "consists of" is not limiting. The use of the term "consists in" is not limiting. The use of the term "consists with" is not limiting. The use of the term "consisting" is not limiting. The use of the term "consists" is not limiting. The use of the term "consists of" is not limiting. The use of the term "consists in" is not limiting. The use of the term "consists with" is not limiting. The use of the term "consisting" is not limiting. The use of the term "consists" is not limiting. The use of the term "consists of" is not limiting. The use of the term "consists in" is not limiting. The use of the term "consists with" is not limiting. The use of the term "consisting" is not limiting. The use of the term "consists" is not limiting. The use of the term "consists of" is not limiting. The use of the term "consists in" is not limiting. The use of the term "consists with" is not limiting. The use of the term "consisting" is not limiting. The use of the term "consists" is not limiting. The use of the term "consists of" is not limiting. The use of the term "consists in" is not limiting. The use of the term "consists with" is not limiting. The use of the term "consisting

Claims

1. An organic electronic device comprising an anode, a cathode, at least one photoactive layer, and an organic semiconductor layer, wherein the organic semiconductor layer is disposed between the at least one photoactive layer and the cathode; and wherein the organic semiconductor layer comprises a compound of formula (1): in R 1 to R 5 is a single bond to the 3-position (marked with "*") of the 2-azaindolizine moiety, Other R 1 to R 5 and R 6 to R 9 independently selected from H, D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cycloalkyl, C3 to C 16 Branched alkoxy, C3 to C 16 Cycloalkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 10 )2, F or CN, and / or any two adjacent R 1 to R 9 Can be substituted and linked together to form unsubstituted or C6 to C 18 Aryl, C3 to C 20 Heteroaryl or C1 to C 16 an alkyl-substituted aromatic or heteroaromatic ring; L is selected from substituted or unsubstituted C6 to C 24 Arylene group or substituted or unsubstituted C2 to C 24 heteroaromatic subunit groups; Ar is selected from any one of the following moieties D1 to D76: where R 14 、R 15 and R 16 Independently selected from H, Cl to C 16 Alkyl, C1 to C 16 Alkoxy, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, perfluorinated C1 to C 16 Alkyl, perfluorinated C1 to C 16 Alkoxy, where R 14 and R 15 They may be linked by single bonds or heteroatoms to form rings; Wherein the substituents of L and Ar are independently selected from: H, D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cycloalkyl, C3 to C 16 Branched alkoxy, C3 to C 16 Cycloalkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 Alkoxy, F, CN or PX 1 (R 10 ) 2, wherein the substituents may be connected via a single bond or a heteroatom to form a ring, where R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 alkoxy; And X 1 Selected from O, S or Se.

2. The organic electronic device according to claim 1, wherein X 1 Selected from O.

3. The organic electronic device according to claim 1, wherein the other R that does not form a single bond with the 3-position of the 2-azaindolizine moiety 1 to R 5 and R 6 to R 9 The substituents are independently selected from D, -CH=, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cycloalkyl, C3 to C 16 Branched alkoxy, C3 to C 16 Cycloalkoxy, partially or perfluorinated, C1 to C 16 Alkyl, partially or fully fluorinated, C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 10 )2, F or CN.

4. The organic electronic device according to claim 1, wherein the compound has the following formula (1a): 5 . The organic electronic device according to claim 1 , wherein the organic semiconductor layer and / or the compound of formula (1) is non-luminescent.

6. The organic electronic device according to any one of claims 1 to 4, wherein R which does not form a single bond with the 3-position of the 2-azaindolizine moiety 1 to R 9 Independently selected from H, -CH=, C1 to C4 alkyl, F or CN.

7. The organic electronic device according to any one of claims 1 to 4, wherein the compound of formula (1) is selected from one of the following formulae (2a) to (2f): where R 11 Independently selected from D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cycloalkyl, C3 to C 16 Branched alkoxy, C3 to C 16 Cycloalkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 10 )2, F or CN; and n is an integer from 0 to 4.

8. The organic electronic device according to any one of claims 1 to 4, wherein L is selected from any one of the following E1 to E26: in X 2 Selected from O or S; R 11 Independently selected from D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cycloalkyl, C3 to C 16 Branched alkoxy, C3 to C 16 Cycloalkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C 16 Alkyl, partially or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 10 )2, F or CN.

9. The organic electronic device according to claim 8, wherein X 2 Selected from O.

10. The organic electronic device according to any one of claims 1 to 4, wherein the organic semiconductor layer comprises a redox n-type dopant. 11 . The organic electronic device according to claim 1 , wherein the organic semiconductor layer comprises a metal.

12. The organic electronic device according to any one of claims 1 to 4, wherein the organic semiconductor layer comprises a metal selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, and first transition period metals Ti, V, Cr, and Mn.

13. The organic electronic device according to any one of claims 1 to 4, wherein the at least one photoactive layer is a light-emitting layer.

14. The organic electronic device according to any one of claims 1 to 4, wherein the organic electronic device is an electroluminescent device. The organic electronic device according to claim 14 , wherein the organic electronic device is an organic light emitting diode. 16 . A display device comprising the organic electronic device according to claim 1 .

17. A compound of formula (1) as claimed in claim 1, wherein the following compounds are excluded:

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