Charge generating layers comprising compounds of formula (I), organic electronic and display devices comprising said charge generating layers, and compounds of formula (I)

Abstract

The present invention relates to a charge generating layer comprising a compound of formula (I).The present invention further relates to said charge generating layer and to organic electronic and display devices comprising a compound of formula (I).

Description

Detailed Description of the Invention

[0001] [Technical field] The present invention relates to a charge generating layer comprising a compound of formula (I).The present invention further relates to organic electronic and display devices comprising said charge generating layer, and to a compound of formula (I).

[0002] [Background technology] Organic electronic devices such as organic light-emitting diodes (OLEDs) are self-emitting devices that have a wide viewing angle, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproducibility. A typical OLED includes an anode, a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and a cathode, which are stacked in order on a substrate. Among these, the HTL, the EML, and the ETL are thin films formed from organic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode migrate to the EML via the HTL, and electrons injected from the cathode migrate to the EML via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from the excited state to the ground state, light is emitted. It is desirable for the injection and flow of holes and electrons to be balanced. Therefore, OLEDs with the above-mentioned structure have excellent efficiency and / or long life.

[0004] The performance of the organic light emitting diode may be influenced by the properties of the semiconducting layer, and in particular by the properties of the compound of formula (I) that is also contained in the semiconducting layer.

[0005] There remains a need to improve the performance of organic semiconductor materials, semiconducting layers, and organic electronic devices thereof, in particular to achieve improved brightness or lifetime, or reduced current density, and to improve the properties of the compounds contained therein.

[0006] [Disclosure] One aspect of the present invention is a charge generating layer comprising a first charge generating layer and a second charge generating layer, the first charge generating layer comprising a compound of formula (I):

[0007] [ka]

[0008] Here, in formula (I), A 1 is independently selected from the group of formula (II):

[0009] [ka]

[0010] Here, Ar 1 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 1 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; A 2 and A 3 is independently selected from the group of formula (III):

[0011] [ka]

[0012] Here, Ar 2 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 2is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; Each R' is a substituted or unsubstituted C6-C 18 Aryl, C3-C 18 independently selected from heteroaryl, electron withdrawing groups, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, halogen, F or CN; Here, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦459 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) with the hybrid functional PBE0 with the def2-SVP basis set in the gas phase and * When calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set, the absorption maximum λ is ≦494 nm. max and / or using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), and * has an integral of ≦50 a.u.×nm in the UV-Vis spectrum in the range of 400-650 nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set; wherein the first charge generating layer comprises an organic hole transporting compound and the second charge generating layer comprises an organic electron transporting compound and a metal dopant.

[0013] Throughout this application and the claims, unless otherwise noted, any A n , Ar n , B n , R n It should be noted that etc. always refer to the same part.

[0014] In this specification, unless otherwise specified, "substituted" means deuterium, C1-C 12 Alkyl and C1-C 12 Refers to one substitution with alkoxy.

[0015] However, as used herein, "aryl substituted" refers to substitution with one or more aryl groups. The aryl group itself may be substituted with one or more aryl and / or heteroaryl groups.

[0016] Correspondingly, as used herein, "heteroaryl substitution" refers to substitution with one or more heteroaryl groups, which themselves may be substituted with one or more aryl and / or heteroaryl groups.

[0017] In this specification, unless otherwise specified, "alkyl group" refers to a saturated aliphatic hydrocarbyl group. The alkyl group is a C1 to C 12 More specifically, the alkyl group may be a C1 to C 10 It may be an alkyl group or a C1-C6 alkyl group. For example, the C1-C4 alkyl group contains 1 to 4 carbons in the alkyl chain and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl.

[0018] Specific examples of alkyl groups may be methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups.

[0019] The term "cycloalkyl" refers to a saturated hydrocarbyl group derived from a cycloalkane by the formal abstraction of a hydrogen atom from a ring atom contained in the corresponding cycloalkane. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, adamantyl, and the like.

[0020] The term "hetero" is understood to mean that in any structure that may be formed by covalently bonded carbon atoms, at least one carbon atom is replaced by another polyvalent atom. Preferably, said heteroatom is selected from B, Si, N, P, O, S, more preferably selected from N, P, O, S.

[0021] As used herein, the term "aryl group" refers to a hydrocarbyl group that can be generated by formally abstracting one hydrogen atom from an aromatic ring in a corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon that contains at least one aromatic ring or aromatic ring system. Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bonded carbon atoms, said planar ring or ring system containing a conjugated system of delocalized electrons that satisfies the Hückel rule. Examples of aryl groups include monocyclic groups (such as phenyl or tolyl), polycyclic groups that contain multiple aromatic rings connected by single bonds (such as biphenyl), and polycyclic groups that contain fused rings (such as naphthyl or fluoren-2-yl).

[0022] Similarly, under heteroaryl it is understood that groups derived by the formal abstraction of one ring hydrogen from a heteroaromatic ring in compounds containing at least one such ring are particularly preferred.

[0023] Under heterocycloalkyl it is understood that particularly preferred are groups derived by the formal abstraction of one ring hydrogen from a saturated cycloalkyl ring in a compound containing at least one such ring.

[0024] The term "fused aryl rings" or "condensed aryl rings" refers to a ring in which two aryl rings share at least two common sp 2 It is understood that when they share a hybridized carbon atom, they are considered to be fused or condensed.

[0025] The term "electron-withdrawing group" refers to a chemical group in a molecule that is capable of withdrawing electrons from adjacent parts of the molecule. The distance over which an electron-withdrawing group can exert its effect, i.e., the number of bonds over which the electron-withdrawing effect extends, is extended by conjugated π-electron systems such as aromatic systems. Examples of electron-withdrawing groups include NO2, CN, halogens, Cl, F, partially fluorinated or perfluorinated alkyls, and partially fluorinated or perfluorinated C1-C 12 Examples include alkyl, partially fluorinated or perfluorinated alkoxy, partially fluorinated or perfluorinated C1-C6 alkoxy.

[0026] As used herein, a single bond refers to a direct bond.

[0027] The term "n-type charge generating layer" may also be referred to in the art as an n-CGL or an electron generating layer, and is intended to include both.

[0028] The term "p-type charge generating layer" may also be referred to in the art as a p-CGL or a hole generating layer, and is intended to include both.

[0029] The terms "free of", "does not contain" and "does not comprise" do not exclude impurities that may be present in the compound prior to deposition. The impurities have no technical impact with respect to the objectives achieved by the present invention.

[0030] The term "interposed contact" refers to a three-layer arrangement in which a middle layer is in direct contact with two adjacent layers.

[0031] The terms "light-absorbing layer" and "light absorption layer" are used interchangeably.

[0032] The terms "light-emitting layer," "light emission layer," and "emission layer" are used interchangeably.

[0033] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used interchangeably.

[0034] The terms "anode," "anode layer," and "anode electrode" are used interchangeably.

[0035] The terms "cathode," "cathode layer," and "cathode electrode" are used interchangeably.

[0036] In this specification, the hole characteristic refers to the ability to donate electrons to form holes when an electric field is applied, and the holes formed in the anode can be easily injected into and transported through the light-emitting layer due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) level.

[0037] Furthermore, the electronic properties refer to the ability to accept electrons when an electric field is applied, and the electrons formed in the cathode can be easily injected into and transported through the light-emitting layer due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) level.

[0038] According to the present invention, 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦459 nm. maxThe characteristic of having should be understood to mean that the compound has at least one absorption maximum at or below a given wavelength. In particular, this refers to an absorption maximum in the range measured by a UV-Vis spectrophotometer, in particular in the range of 248 nm to 1000 nm. Preferably, the compound has a maximum absorption at or below a given wavelength. In other words, this means that the compound does not have an absorption maximum greater than a given wavelength.

[0039] According to the invention, the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) was used to perform the calculations using PBE0 with the def2-SVP basis set in the gas phase and 6-31G * When calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set, the absorption maximum λ is ≦494 nm. max The characteristic of having should be understood to mean that the compound has at least one absorption maximum at or below a given wavelength. In particular, this refers to an absorption maximum in the range measured by a UV-Vis spectrophotometer, particularly in the range of 300nm to 650nm, especially in the range of 350nm to 650nm. Preferably, the compound has a maximum absorption at or below a given wavelength. In other words, this means that the compound does not have an absorption maximum greater than a given wavelength.

[0040] DCM is dichloromethane.

[0041] According to the invention, the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) was used to generate the 6-31G basis set in the gas phase. *The feature of having an integral value of ≦50 a.u.×nm in the UV-Vis spectrum in the range of 400-650 nm when calculated by TDDFT including the first 30 singlet transitions from an optimized geometry using the hybrid functional B3LYP with basis set means that in the calculated UV-Vis spectrum, the quantitative area of ​​absorption in the given range is less than or equal to a given value.

[0042] [Advantageous Effects] Surprisingly, it has been found that the charge generating layer according to the present invention enables devices in various aspects to be superior to organic electronic devices known in the art, particularly with respect to improved brightness or lifetime, or reduced current density, and solves the problem underlying the present invention by improving the properties of the compounds contained therein.

[0043] According to one embodiment of the present invention, the organic hole transport compound is not a metal complex and / or a metal organic compound, preferably the organic hole transport compound does not contain any metal atoms.

[0044] According to one embodiment of the invention, the organic electron transport compound is not a metal complex and / or a metal organic compound, and preferably the organic electron transport compound does not contain any metal atoms.

[0045] According to one embodiment of the present invention, the charge generating layer is not a charge generating layer selected from the group consisting of a) to x): a) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0046] [ka]

[0047] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; b) The first charge generating layer is 1 , A 2 and A 3 9.8% by volume of a compound of formula (I) selected according to:

[0048] [ka]

[0049] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; c) The first charge generating layer is 1 , A 2 and A 3 12% by volume of a compound of formula (I) selected according to:

[0050] [ka]

[0051] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; d) The first charge generating layer is 1 , A 2 and A 3 9.6% by volume of a compound of formula (I) selected according to:

[0052] [ka]

[0053] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; e) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0054] [ka]

[0055] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; f) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0056] [ka]

[0057] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; g) The first charge generating layer is 1 , A 2 and A 3 10.8% by volume of a compound of formula (I) selected according to:

[0058] [ka]

[0059] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; h) The first charge generating layer is 1 , A 2 and A 3 11.8% by volume of a compound of formula (I) selected according to:

[0060] [ka]

[0061] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; i) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0062] [ka]

[0063] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; j) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0064] [ka]

[0065] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; k) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0066] [ka]

[0067] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; l) The first charge generating layer is 1 , A 2 and A 3 5% by volume of a compound of formula (I) selected according to:

[0068] [ka]

[0069] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; m) The first charge generating layer is 1 , A 2 and A 3 5% by volume of a compound of formula (I) selected according to:

[0070] [ka]

[0071] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; n) The first charge generating layer is 1 , A 2 and A 3 % or 10% by volume of a compound of formula (I) selected according to:

[0072] [ka]

[0073] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; o) The first charge generating layer is 1 , A 2 and A 3 % or 10% by volume of a compound of formula (I) selected according to:

[0074] [ka]

[0075] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; p) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0076] [ka]

[0077] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; q) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0078] [ka]

[0079] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; r) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0080] [ka]

[0081] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; s) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0082] [ka]

[0083] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; t) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0084] [ka]

[0085] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; u) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0086] [ka]

[0087] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; v) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0088] [ka]

[0089] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 15 nm; w) the first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0090] [ka]

[0091] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li, the second charge generating layer having a thickness of 15 nm; and x) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0092] [ka]

[0093] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; 14. A charge generating layer comprising: a first charge generating layer and a second charge generating layer comprising: 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; and wherein the second charge generating layer has a thickness of 15 nm.

[0094] According to one embodiment of the present invention, further, the charge generating layer is not a charge generating layer selected from the group consisting of y) to z): y) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0095] [ka]

[0096] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, said first charge generating layer having a thickness of 10 nm, and said second charge generating layer comprising 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li, said second charge generating layer having a thickness of 15 nm; z) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0097] [ka]

[0098] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm, and the second charge generating layer comprising 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li, the second charge generating layer having a thickness of 15 nm.

[0099] According to one embodiment of the present invention, the charge generating layer is not a charge generating layer selected from the group consisting of a) to x): a) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0100] [ka]

[0101] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; b) The first charge generating layer is 1 , A 2 and A 3 9.8% by volume of a compound of formula (I) selected according to:

[0102] [ka]

[0103] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; c) The first charge generating layer is 1 , A 2 and A 3 12% by volume of a compound of formula (I) selected according to:

[0104] [ka]

[0105] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; d) The first charge generating layer is 1 , A 2 and A 3 9.6% by volume of a compound of formula (I) selected according to:

[0106] [ka]

[0107] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; e) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0108] [ka]

[0109] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; f) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0110] [ka]

[0111] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; g) The first charge generating layer is 1 , A 2 and A 3 10.8% by volume of a compound of formula (I) selected according to:

[0112] [ka]

[0113] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; h) The first charge generating layer is 1 , A 2 and A 3 11.8% by volume of a compound of formula (I) selected according to:

[0114] [ka]

[0115] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; i) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0116] [ka]

[0117] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; j) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0118] [ka]

[0119] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; k) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0120] [ka]

[0121] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; l) The first charge generating layer is 1 , A 2 and A 35% by volume of a compound of formula (I) selected according to:

[0122] [ka]

[0123] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; m) The first charge generating layer is 1 , A 2 and A 3 5% by volume of a compound of formula (I) selected according to:

[0124] [ka]

[0125] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; n) The first charge generating layer is 1 , A 2 and A 3 % or 10% by volume of a compound of formula (I) selected according to:

[0126] [ka]

[0127] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; o) The first charge generating layer is 1 , A 2 and A 3 comprises 5% or 10% by volume of a compound of formula (I) selected according to:

[0128] [ka]

[0129] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; p) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0130] [ka]

[0131] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; q) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0132] [ka]

[0133] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; r) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0134] [ka]

[0135] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% or 3% by volume of Li; s) The first charge generating layer is 1 , A 2 and A 310% by weight of a compound of formula (I) selected according to:

[0136] [ka]

[0137] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; t) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0138] [ka]

[0139] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; u) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0140] [ka]

[0141] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; v) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0142] [ka]

[0143] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; w) the first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0144] [ka]

[0145] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li; and x) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0146] [ka]

[0147] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, The second charge generating layer comprises 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li.

[0148] According to one embodiment of the present invention, further, the charge generating layer is not a charge generating layer selected from the group consisting of y) to z): y) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0149] [ka]

[0150] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, and said second charge generating layer comprises 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li; z) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0151] [ka]

[0152] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm, and the second charge generating layer comprising 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li, the second charge generating layer having a thickness of 15 nm.

[0153] According to one embodiment of the present invention, the charge generating layer is not a charge generating layer selected from the group consisting of a) to x): a) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0154] [ka]

[0155] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; b) The first charge generating layer is 1 , A 2 and A 3 9.8% by volume of a compound of formula (I) selected according to:

[0156] [ka]

[0157] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; c) The first charge generating layer is 1 , A 2 and A 3 12% by volume of a compound of formula (I) selected according to:

[0158] [ka]

[0159] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; d) The first charge generating layer is 1 , A 2 and A 3 9.6% by volume of a compound of formula (I) selected according to:

[0160] [ka]

[0161] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; e) The first charge generating layer is 1 , A 2 and A 3 10.1% by volume of a compound of formula (I) selected according to:

[0162] [ka]

[0163] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; f) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0164] [ka]

[0165] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; g) The first charge generating layer is 1 , A 2 and A 3 10.8% by volume of a compound of formula (I) selected according to:

[0166] [ka]

[0167] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; h) The first charge generating layer is 1 , A 2 and A 3 11.8% by volume of a compound of formula (I) selected according to:

[0168] [ka]

[0169] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; i) The first charge generating layer is 1 , A 2 and A 3 9.9% by volume of a compound of formula (I) selected according to:

[0170] [ka]

[0171] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; j) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0172] [ka]

[0173] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; k) The first charge generating layer is 1 , A 2 and A 3 10.3% by volume of a compound of formula (I) selected according to:

[0174] [ka]

[0175] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; l) The first charge generating layer is 1 , A 2 and A 3 5% by volume of a compound of formula (I) selected according to:

[0176] [ka]

[0177] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; m) The first charge generating layer is 1 , A 2 and A 3 5% by volume of a compound of formula (I) selected according to:

[0178] [ka]

[0179] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; n) The first charge generating layer is 1 , A 2 and A 3 comprises 5% or 10% by volume of a compound of formula (I) selected according to:

[0180] [ka]

[0181] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; o) The first charge generating layer is 1 , A 2 and A 3 comprises 5% or 10% by volume of a compound of formula (I) selected according to:

[0182] [ka]

[0183] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; p) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0184] [ka]

[0185] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; q) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0186] [ka]

[0187] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; r) The first charge generating layer is 1 , A 2 and A 3 10% by volume of a compound of formula (I) selected according to:

[0188] [ka]

[0189] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; s) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0190] [ka]

[0191] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; t) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0192] [ka]

[0193] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; u) The first charge generating layer is 1 , A 2 and A 3 10% by weight of a compound of formula (I) selected according to:

[0194] [ka]

[0195] the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 10 nm; v) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0196] [ka]

[0197] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 15 nm; w) the first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0198] [ka]

[0199] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant, the second charge generating layer having a thickness of 15 nm; and x) The first charge generating layer is 1 , A 2 and A 3 comprises 10% by volume or 10% by weight of a compound of formula (I) selected according to:

[0200] [ka]

[0201] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; 2. A charge generating layer comprising: 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline]; and Li as a metal dopant; wherein the second charge generating layer has a thickness of 15 nm.

[0202] According to one embodiment of the present invention, the charge generating layer is not a charge generating layer selected from the group consisting of a) to x): a) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0203] [ka]

[0204] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; b) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0205] [ka]

[0206] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; c) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0207] [ka]

[0208] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; d) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0209] [ka]

[0210] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; e) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0211] [ka]

[0212] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; f) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0213] [ka]

[0214] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; g) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0215] [ka]

[0216] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; h) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0217] [ka]

[0218] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; i) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0219] [ka]

[0220] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; j) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0221] [ka]

[0222] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; k) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0223] [ka]

[0224] and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; l) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0225] [ka]

[0226] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; m) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0227] [ka]

[0228] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; n) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0229] [ka]

[0230] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; o) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0231] [ka]

[0232] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; p) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0233] [ka]

[0234] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; q) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0235] [ka]

[0236] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; r) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0237] [ka]

[0238] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; s) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0239] [ka]

[0240] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; t) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0241] [ka]

[0242] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; u) The first charge generating layer is 1 , A 2 and A 3is selected according to:

[0243] [ka]

[0244] the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; v) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0245] [ka]

[0246] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; w) the first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0247] [ka]

[0248] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, the second charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant; x) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0249] [ka]

[0250] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, The second charge generating layer comprises 99 volume % of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and Li as a metal dopant.

[0251] According to one embodiment of the present invention, further, the charge generating layer is not a charge generating layer selected from the group consisting of y) to z): y) The first charge generating layer is 1 , A 2 and A 3 is selected according to:

[0252] [ka]

[0253] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, and said second charge generating layer comprises 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li; z) The first charge generating layer is1 , A 2 and A 3 is selected according to:

[0254] [ka]

[0255] and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm, and the second charge generating layer comprising 99% by volume 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume Li, the second charge generating layer having a thickness of 15 nm.

[0256] According to one embodiment of the present invention, the charge generating layer is not a charge generating layer selected from the group consisting of a) to z): a) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0257] [ka]

[0258] b) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0259] [ka]

[0260] c) The first charge generating layer is 1 , A 2and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0261] [ka]

[0262] d) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0263] [ka]

[0264] e) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0265] [ka]

[0266] f) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0267] [ka]

[0268] g) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0269] [ka]

[0270] h) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0271] [ka]

[0272] i) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0273] [ka]

[0274] j) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0275] [ka]

[0276] k) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0277] [ka]

[0278] l) The first charge generating layer is 1 , A2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0279] [ka]

[0280] m) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0281] [ka]

[0282] n) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0283] [ka]

[0284] o) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0285] [ka]

[0286] p) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0287] [ka]

[0288] q) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0289] [ka]

[0290] r) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0291] [ka]

[0292] s) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0293] [ka]

[0294] t) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0295] [ka]

[0296] u) The first charge generating layer is 1, A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0297] [ka]

[0298] v) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0299] [ka]

[0300] w) the first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0301] [ka]

[0302] x) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0303] [ka] .

[0304] According to one embodiment of the present invention, further, the charge generating layer is not a charge generating layer selected from the group consisting of y) to z): y) The first charge generating layer is 1 , A 2 and A3 a charge generating layer comprising a compound of formula (I) selected according to:

[0305] [ka]

[0306] z) The first charge generating layer is 1 , A 2 and A 3 a charge generating layer comprising a compound of formula (I) selected according to:

[0307] [ka] .

[0308] According to one embodiment of the present invention, the first charge generating layer is a p-type charge generating layer.

[0309] According to one embodiment of the present invention, the second charge generating layer is an n-type charge generating layer.

[0310] According to one embodiment of the present invention, the first charge generating layer is a p-type charge generating layer and the second charge generating layer is an n-type charge generating layer.

[0311] According to one embodiment of the present invention, the charge generating layer is not one of the charge generating layers described above in any one of charge generating layers a) to xz).

[0312] According to one embodiment of the present invention, the charge generating layer is not one of the charge generating layers a) to z) described above.

[0313] [Metal dopants] According to one embodiment of the invention, the metal dopant is selected from metals having an electronegativity of ≦1.4 eV on the Pauling scale or metal alloys comprising metals having an electronegativity of ≦1.4 eV on the Pauling scale.

[0314] According to one embodiment of the invention, the metal dopant is selected from metals having an electronegativity of ≦1.35 eV on the Pauling scale or metal alloys comprising metals having an electronegativity of ≦1.35 eV on the Pauling scale.

[0315] According to one embodiment of the invention, the metal dopant is a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb, or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb.

[0316] According to one embodiment of the invention, the metal dopant is a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb, or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb.

[0317] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li, Mg and Yb, or a metal alloy containing a metal selected from the group consisting of Li, Mg and Yb.

[0318] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li and Yb, or a metal alloy containing a metal selected from the group consisting of Li and Yb.

[0319] According to one embodiment of the present invention, the metal dopant is Yb or a metal alloy containing a metal selected from the group consisting of Li and Yb.

[0320] According to one embodiment of the present invention, the metal dopant is Yb.

[0321] [Organic Hole Transport Compounds] According to one embodiment of the present invention, the organic hole transport compound is prepared by dissolving 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying said hybrid functional B3LYP having a basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level being zero, is in the range of ≦-4.4 eV to ≧-5.2 eV, more preferably ≦-4.5 eV to ≧-5.1 eV, even more preferably ≦-4.6 eV to ≧-5.0 eV, and most preferably ≦-4.65 eV to ≧-4.9 eV.

[0322] According to one embodiment of the present invention, the organic hole transport compound is present in the first charge generating layer in an amount of at least 0.1 wt%, preferably at least 1 wt%, more preferably at least 5 wt%, more preferably at least 10 wt%, more preferably at least 20 wt%, more preferably at least 30 wt%, more preferably at least 40 wt%, more preferably at least 50 wt%, more preferably at least 60 wt%, more preferably at least 70 wt%, more preferably at least 80 wt%, and most preferably at least 90 wt%, based on the total weight of the first charge generating layer.

[0323] According to one embodiment of the present invention, the organic hole transport compound is a substantially covalent matrix compound.

[0324] Substantially Covalent Matrix Compounds The semiconducting layer and / or the charge generating layer may further comprise a substantially covalent matrix compound which may consist essentially of covalently bonded C, H, O, N, S, and optionally further comprise covalently bonded B, P, As and / or Se.

[0325] According to one embodiment, the substantially covalent matrix compound may be selected from organic compounds consisting essentially of covalently bound C, H, O, N, S, and optionally further comprising covalently bound B, P, As and / or Se.

[0326] In one embodiment, the substantially covalent matrix compound is devoid of metal atoms and the majority of its backbone atoms may be selected from C, O, S, N. Alternatively, the substantially covalent matrix compound is devoid of metal atoms and the majority of its backbone atoms may be selected from C and N.

[0327] According to one embodiment of the invention, the organic hole transport compound comprises at least 15 covalently bonded atoms, preferably at least 20 covalently bonded atoms, more preferably at least 25 covalently bonded atoms, more preferably at least 30 covalently bonded atoms, more preferably at least 35 covalently bonded atoms, more preferably at least 40 covalently bonded atoms, more preferably at least 45 covalently bonded atoms.

[0328] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≧400 g / mol and ≦2000 g / mol, preferably a molecular weight Mw of ≧450 g / mol and ≦1500 g / mol, further preferably a molecular weight Mw of ≧500 g / mol and ≦1000 g / mol, further preferably a molecular weight Mw of ≧550 g / mol and ≦900 g / mol, further preferably a molecular weight Mw of ≧600 g / mol and ≦800 g / mol.

[0329] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, alternatively a diarylamine moiety, or alternatively a triarylamine moiety.

[0330] Preferably, the substantially covalent matrix compound is free of metal and / or ionic bonds.

[0331] [Compound of formula (IV) or compound of formula (V)] According to another aspect of the invention, the at least one matrix compound, also called "substantially covalent matrix compound", may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (IV) or compound of formula (V),

[0332] [ka]

[0333] where: T 1 , T 2 , T 3 , T 4 and T 5 are independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthenylene, preferably a single bond or phenylene; T 6 is phenylene, biphenylene, terphenylene or naphthenylene; Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 is a substituted or unsubstituted C6-C 20 Aryl or substituted or unsubstituted C3-C 20Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted tetracene, substituted or unsubstituted tetraphene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted or unsubstituted are independently selected from the group consisting of unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene], or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from the group consisting of substituted or unsubstituted non-hetero, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene, or fused ring systems comprising 2 to 6 substituted or unsubstituted 5- to 7-membered rings, wherein the rings are independently selected from the group consisting of (i) unsaturated 5- to 7-membered heterocyclic rings, (ii) 5- to 6-membered aromatic heterocyclic rings, (iii) unsaturated 5- to 7-membered non-heterocyclic rings, (iv) fused ring systems comprising 6-membered aromatic non-heterocyclic rings; Where: Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 The substituents are H, D, F, C(=O)R 2 , CN, Si(R 2 )3, P(=O)(R 2 )2, OR 2 , S(=O)R 2 , S(=O)2R 2, substituted or unsubstituted linear alkyl having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3-C 18 heteroaryl; a fused ring system containing 2 to 6 unsubstituted 5- to 7-membered rings, the rings being the same or different and selected from the group consisting of a fused ring system selected from the group consisting of a heterocyclic unsaturated 5- to 7-membered ring, an aromatic heterocyclic 5- to 6-membered ring, a non-heterocyclic unsaturated 5- to 7-membered ring, and an aromatic non-heterocyclic 6-membered ring; Here, R 2 is H, D, a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an alkenyl or alkynyl group having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3-C 18 Heteroaryl may be selected from the group consisting of aryl, heteroaryl, and heteroaryl.

[0334] According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a single bond, phenylene, biphenylene or terphenylene. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene, biphenylene or terphenylene; T 1 , T 2 , T 3 , T 4 and T 5 is a single bond. According to one embodiment, T1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene or biphenylene; T 1 , T 2 , T 3 , T 4 and T 5 is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene or biphenylene; T 1 , T 2 , T 3 , T 4 and T 5 Two of the are single bonds.

[0335] According to one embodiment, T 1 , T 2 and T 3 may be independently selected from phenylene; T 1 , T 2 and T 3 is a single bond. According to one embodiment, T 1 , T 2 and T 3 may be independently selected from phenylene; T 1 , T 2 and T 3 Two of the are single bonds.

[0336] According to one embodiment, T 6 may be phenylene, biphenylene, terphenylene. According to one embodiment, T 6 may be phenylene. According to one embodiment, T 6 may be biphenylene. According to one embodiment, T 6 may be terphenylene.

[0337] According to one embodiment, Ar' 1, Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 may be independently selected from D1-D16:

[0338] [ka]

[0339] Here, the asterisk "*" indicates the binding position.

[0340] According to one embodiment, Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 may be independently selected from D1 to D15; or may be selected from D1 to D10 and D13 to D15.

[0341] According to one embodiment, Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 may be independently selected from the group consisting of D1, D2, D5, D7, D9, D10, and D13 to D16.

[0342] Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 When is selected in this range, the rate onset temperature can be in a range that is particularly suitable for mass production.

[0343] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, a carbazole group, a dibenzofuran group, a dibenzothiophene group and / or a substituted fluorenyl group, the substituents being independently selected from methyl, phenyl or fluorenyl.

[0344] According to an embodiment of the present invention, the matrix compound of formula (IV) or formula (V) is selected from F1 to F18:

[0345] [ka] JPEG2025500369000136.jpg174169JPEG2025500369000137.jpg97169.

[0346] [Organic electron transport compound] According to one embodiment of the invention, the organic electron transport compound is a substantially organic covalent electron transport compound.

[0347] According to one embodiment of the invention, the organic electron transport compound is devoid of metal atoms and the majority of its backbone atoms may be selected from C, H, O, N, S, and optionally further includes covalently bound B, P, As and / or Se.

[0348] The organic electron transport compound can consist essentially of covalently bound C, H, O, N, S, and optionally further contain covalently bound B, P, As, and / or Se.

[0349] According to one embodiment of the present invention, the organic electron transport compound preferably has at least one C2-C 24 It includes N-heteroaryl groups or P=X groups, where X is O, P, Se, with P=O being particularly preferred.

[0350] According to one embodiment of the present invention, at least one of C2 to C 24 The N-heteroaryl may be selected from compounds containing at least one azine group, preferably at least two azine groups, and more preferably three azine groups.

[0351] According to one embodiment of the present invention, the organic electron transport compound comprises at least one group selected from the list consisting of pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzoxazole, quinone, benzoquinone, quinoxaline, benzoquinoxaline, acridine, phenanthroline, benzoacridine, and dibenzoacridine.

[0352] According to one embodiment of the present invention, the organic electron transport compound comprises at least 15 covalently bonded atoms, preferably at least 20 covalently bonded atoms, more preferably at least 25 covalently bonded atoms, and most preferably at least 30 covalently bonded atoms.

[0353] According to one embodiment of the present invention, the substantially organic covalently bonded electron transport compound comprises at least 15 covalently bonded atoms, preferably at least 20 covalently bonded atoms, more preferably at least 25 covalently bonded atoms, and most preferably at least 30 covalently bonded atoms.

[0354] According to one embodiment of the present invention, the organic electron transport compound may have a molecular weight Mw of ≧400 g / mol and ≦2000 g / mol, preferably a molecular weight Mw of ≧450 g / mol and ≦1500 g / mol, more preferably a molecular weight Mw of ≧500 g / mol and ≦1000 g / mol, more preferably a molecular weight Mw of ≧550 g / mol and ≦900 g / mol, more preferably a molecular weight Mw of ≧580 g / mol and ≦800 g / mol, and more preferably a molecular weight Mw of ≧600 g / mol and ≦800 g / mol.

[0355] According to one embodiment of the present invention, the organic electron transport compound is B3LYP / 6-31G *In particular, according to one embodiment of the present invention, the organic electron transport compound has a LUMO of <-1.75 eV as calculated by DFT using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) in the gas phase. * When calculated by applying the hybrid functional B3LYP with the basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level being zero, is <-1.75 eV.

[0356] According to one embodiment of the invention, the organic electron transport compound is present in the second charge generating layer in an amount of at least 0.1 weight percent, preferably at least 1 weight percent, more preferably at least 5 weight percent, more preferably at least 10 weight percent, more preferably at least 20 weight percent, more preferably at least 30 weight percent, more preferably at least 40 weight percent, more preferably at least 50 weight percent, more preferably at least 60 weight percent, more preferably at least 70 weight percent, more preferably at least 80 weight percent, more preferably at least 90 weight percent, more preferably at least 95 weight percent, more preferably at least 96 weight percent, more preferably at least 97 weight percent, and most preferably at least 98 weight percent, based on the total weight of the second charge generating layer.

[0357] Compound of formula (I) According to one embodiment of the present invention, Ar 1 is C6~C 30 Aryl and substituted or unsubstituted C2-C 30 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0358] According to one embodiment of the present invention, Ar 1 is C6~C 24 Aryl and substituted or unsubstituted C2-C 24 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0359] According to one embodiment of the present invention, Ar 1 is C6~C 18 Aryl and substituted or unsubstituted C3-C 18 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0360] According to one embodiment of the present invention, Ar 1 is C6~C 12 Aryl and substituted or unsubstituted C3-C 12 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0361] According to one embodiment of the present invention, Ar 1 When is substituted, one or more of said substituents are independently selected from the group consisting of F, CN, partially or perfluorinated C1-C8 alkyl, particularly CF3, and -NO2.

[0362] According to one embodiment of the present invention, Ar 1 When is substituted, one or more of said substituents are independently selected from the group consisting of F, CN, and partially or perfluorinated C1-C8 alkyl, particularly CF3.

[0363] According to one embodiment of the present invention, Ar 2 is C6~C 30 Aryl and substituted or unsubstituted C2-C 30 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0364] According to one embodiment of the present invention, Ar 2 is C6~C 24 Aryl and substituted or unsubstituted C2-C 24 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0365] According to one embodiment of the present invention, Ar 2 is C6~C 18 Aryl and substituted or unsubstituted C3-C 18 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0366] According to one embodiment of the present invention, Ar 2 is C6~C 12 Aryl and substituted or unsubstituted C3-C 12 Heteroaryl is selected from the group consisting of aryl, hetero ...

[0367] According to one embodiment of the present invention, Ar 2 When is substituted, one or more of said substituents are independently selected from the group consisting of F, CN, partially or perfluorinated C1-C8 alkyl, particularly CF3, and -NO2.

[0368] According to one embodiment of the present invention, Ar 2 When is substituted, one or more of said substituents are independently selected from the group consisting of F, CN, and partially or perfluorinated C1-C8 alkyl, particularly CF3.

[0369] According to one embodiment of the present invention, R' is independently selected from the group consisting of electron withdrawing groups, CN, halogen, F, partially fluorinated C1-C8 alkyl, and perfluorinated C1-C8 alkyl, in particular CF3.

[0370] According to one embodiment of the present invention, R' is independently selected from the group consisting of CN, F, partially fluorinated C1-C8 alkyl, and perfluorinated C1-C8 alkyl, in particular CF3.

[0371] According to one embodiment of the present invention, R' is independently selected from CN.

[0372] According to one embodiment of the present invention, formula (II) is selected from formula (VI):

[0373] [ka]

[0374] In the formula (VI), X 1 CR 1or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 or N; X 5 CR 5 or N; R 1 , R 2 , R 3 , R 4 and R 5 (when present) are independently selected from an electron withdrawing group, CN, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H, whereby R 1 , R 2 , R 3 , R 4 and R 5 If any of X exists, 1 , X 2 , X 3 , X 4 and X 5 is not N.

[0375] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, CN, -NO2, halogen, Cl, or F.

[0376] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, or CN.

[0377] According to one embodiment of the present invention, X 1 is CR 1 and R1 is selected from partially fluorinated C1-C8 alkyl or perfluorinated C1-C8 alkyl.

[0378] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from CF3.

[0379] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 are independently selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, CN, -NO2, halogen, Cl, or F.

[0380] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, or CN.

[0381] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from partially fluorinated C1-C8 alkyl or perfluorinated C1-C8 alkyl.

[0382] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from CF3.

[0383] According to one embodiment of the present invention, in formula (I), A 1 is independently selected from the group of formula (IIa):

[0384] [ka]

[0385] Here, B 1 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 1 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 3 is independently selected from the group of formula (IIIa):

[0386] [ka]

[0387] Here, B 3 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 3 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 5 is independently selected from the group of formula (IIIb):

[0388] [ka]

[0389] Here, B5 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 5 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 2 , B 4 , and B. 6 is a substituted or unsubstituted C6-C 18 Aryl, C3-C 18 are each independently selected from heteroaryl, an electron withdrawing group, a partially fluorinated C1-C8 alkyl, a perfluorinated C1-C8 alkyl, a halogen, F or CN.

[0390] According to one embodiment of the present invention, in formula (I), A 1 is independently selected from the group of formula (IIa):

[0391] [ka]

[0392] Here, B 1 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 1 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 3 is independently selected from the group of formula (IIIa):

[0393] [ka]

[0394] Here, B 3 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 3 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 5 is independently selected from the group of formula (IIIb):

[0395] [ka]

[0396] Here, B 5 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; B 5 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 2 , B 4 , and B. 6 is a substituted or unsubstituted C6-C 18 Aryl, C3-C 18 are each independently selected from heteroaryl, an electron withdrawing group, a partially fluorinated C1-C8 alkyl, a perfluorinated C1-C8 alkyl, a halogen, F or CN; Here, the obtained compound of formula (I) is represented by any one of the following compounds (Ia) to (Ie).

[0397] [ka]

[0398] According to one embodiment of the invention, said groups of formula (IIa) are selected from the same preferred groups as said groups according to formula (II). According to one embodiment of the invention, said groups of formula (IIa) are selected from the same preferred groups as said groups according to formula (VI).

[0399] According to one embodiment of the present invention, said groups of formulae (IIIa) and (IIIb) are independently selected from the same preferred groups as said groups according to formula (III).

[0400] According to one embodiment of the present invention, the groups of formula (IIa) are selected from the same preferred groups as the groups according to formula (II), and the groups of formulas (IIIa) and (IIIb) are independently selected from the same preferred groups as the groups according to formula (III). In particular, according to one embodiment of the present invention, the groups of formulas (IIa), (IIIa) and (IIIb) are independently selected from the same preferred groups as the groups according to formula (III). 1 , A 2 and A 3 The preferred combinations are selected from:

[0401] According to one embodiment of the present invention, the compound of formula (I) is represented by a compound of formula (Ia):

[0402] [ka]

[0403] wherein B is as defined for formula (I); 1 Ar 1 And B 3 and B. 5 Ar 2 and B. 2 And B 4 and B. 6 is R'.

[0404] According to one embodiment of the present invention, the compound of formula (I) is represented by a compound of formula (Ia):

[0405] [ka]

[0406] Here, B 1 Ar 1 and Ar 1 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 1 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 3 and B. 5 Ar 2 and Ar 2 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 2 is substituted, one or more of the substituents are independently selected from the group consisting of electron-withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO2; B 2 , B 4 and B. 6 is R', each R' being a substituted or unsubstituted C6-C 18 Aryl, C3-C 18 are independently selected from heteroaryl, electron withdrawing groups, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, halogen, F or CN.

[0407] According to one embodiment of the present invention, the compound of formula (I) is represented by a compound of formula (Ia):

[0408] [ka]

[0409] Here, B 1 is selected from formula (VIa):

[0410] [ka]

[0411] B 3 and B. 5 Ar 2 and B. 2 And B 4 and B. 6 is R'; In formula (VIa), X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 or N; X 5 CR 5 or N; R 1 , R 2 , R 3 , R 4 and R 5 (when present) are independently selected from an electron withdrawing group, CN, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H, whereby R 1 , R 2 , R 3 , R 4 and R 5 If any of X exists, 1 , X 2 , X 3 , X 4 and X 5 is not N, Here, formula (VIa) is linked to the methylene C atom via the atom indicated as "*".

[0412] According to one embodiment of the present invention, the compound of formula (I) is represented by a compound of formula (Ia):

[0413] [ka]

[0414] Here, B 1 is selected from formula (VIa):

[0415] [ka]

[0416] In the formula (Via), X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 or N; X 5 CR 5 or N; R 1 , R 2 , R 3 , R 4 and R 5 (when present) are independently selected from an electron withdrawing group, CN, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H, whereby R 1 , R 2 , R 3 , R 4 and R 5 If any of X exists, 1, X 2 , X 3 , X 4 and X 5 is not N, wherein formula (VIa) is linked to the methylene C atom via the atom indicated as "*"; B 3 and B. 5 are independently selected from:

[0417] [ka]

[0418] In the formula (xxxxxIII), X 1 ' is a CR 1 ' or N; X 2 ' is a CR 2 ' or N; X 3 ' is a CR 3 ' or N; X 4 ' is a CR 4 ' or N; X 5 ' is a CR 5 ' or N; R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ' (when present) is independently selected from an electron withdrawing group, CN, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H, whereby R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ', if any of the corresponding X 1 ', X 2 ', X 3 ', X 4 ' and X 5 ' is not an N, wherein formula (VIb) is linked to the methylene C atom via the atom indicated as "*"; and B 2 , B 4 and B. 6 is R'.

[0419] According to one embodiment, the first charge generating layer comprises a composition containing, as the compound of formula (I), a compound of formula (Ia) and at least one compound of formulas (Ib) to (Ie).

[0420] [ka]

[0421] According to one embodiment of the present invention, the compound of formula (I) is selected from the compounds of formula (VII)

[0422] [ka]

[0423] Where: Ar 1 is substituted C6~C 36 Aryl or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 1 is substituted, said one or more substituents are independently selected from electron withdrawing groups, F, CN, partially or perfluorinated alkyl, and -NO2; and Ar 2 is a substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 36 heteroaryl; Ar 2is substituted, said one or more substituents are independently selected from electron withdrawing groups, F, CN, partially or perfluorinated alkyl, and -NO2; The compound of formula (VII) can be dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦459 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * When calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with the basis set, the absorption maximum λ is ≦494 nm. max and / or using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) and using the hybrid functional B3LYP / 6-31G * It has an integral of ≦50 a.u.× nm in the UV-Vis spectrum in the range of 400-650 nm when calculated by TDDFT including the first 30 singlet transitions from an optimized geometry using a basis set.

[0424] According to one embodiment of the present invention, the compound of formula (I) is selected from the compounds of formula (VIII)

[0425] [ka]

[0426] each X 1 CR 1 or N; each X2 CR 2 or N; each X 3 CR 3 or N; each X 4 CR 4 or N; each X 5 CR 5 or N; Each R 1 , R 2 , R 3 , R 4 and R 5 (when present) are independently selected from CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D, or H, whereby R 1 , R 2 , R 3 , R 4 and R 5 If any of X exists, 1 , X 2 , X 3 , X 4 and X 5 is not N; The compound of formula (VIII) can be dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦459 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) and using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase and * When calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with the basis set, the absorption maximum λ is ≦494 nm. maxand / or using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), and * It has an integral of ≦50 a.u.×nm in the UV-Vis spectrum in the range of 400-650 nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with basis set.

[0427] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, CN, -NO2, halogen, Cl, or F.

[0428] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, or CN.

[0429] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from partially fluorinated C1-C8 alkyl or perfluorinated C1-C8 alkyl.

[0430] According to one embodiment of the present invention, X 1 is CR 1 and R 1 is selected from CF3.

[0431] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R5 are independently selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, CN, -NO2, halogen, Cl, or F.

[0432] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, or CN.

[0433] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from partially fluorinated C1-C8 alkyl or perfluorinated C1-C8 alkyl.

[0434] According to one embodiment of the present invention, X 1 is CR 1 and X 5 is CR 5 and R 1 and R 5 is independently selected from CF3.

[0435] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦455 nm. max and preferably has an absorption maximum λ ≦450 nm, more preferably ≦445 nm, more preferably ≦441 nm, and most preferably ≦440 nm. max has.

[0436] According to one embodiment of the present invention, the compound of formula (I) can be prepared by the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) using the hybrid functional PBE0 with def2-SVP in the gas phase and 6-31G in the gas phase. * When calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with the basis set, the absorption maximum λ is ≦475 nm. max and preferably has an absorption maximum λ ≦455 nm max has.

[0437] According to one embodiment of the present invention, the compound of formula (I) has an absorption maximum λ ≦475 nm, preferably ≦455 nm. max has.

[0438] According to one embodiment of the present invention, the compound of formula (I) can be prepared by the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase and 6-31G * When calculated by TDDFT including the first 30 singlet transitions from an optimized geometry using the hybrid functional B3LYP having a basis set, it has an integral of ≦49 a.u.×nm in the UV-Vis spectrum in the range of 400-650 nm, preferably ≦48 a.u.×nm, more preferably ≦47 a.u.×nm, more preferably ≦46 a.u.×nm, more preferably ≦45 a.u.×nm, more preferably ≦44 a.u.×nm, more preferably ≦43 a.u.×nm, and most preferably ≦42 a.u.×nm.

[0439] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4When measured at a concentration of mol / L, the absorption maximum λ is ≦455 nm. max (absorption), using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), and * The compound of formula (I) has an integral of ≦50 a.u.×nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with basis set. According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at concentrations in mol / L, the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) was used to measure the concentration of 6-31G in the gas phase using the hybrid functional PBE0 with the def2-SVP basis set in the gas phase. * When calculated by TDDFT including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with basis set, it has an integral value of ≦46 a.u.×nm.

[0440] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦445 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and *When calculated by TDDFT including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with basis set, it has an integral value of ≦45 a.u.×nm.

[0441] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦441. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * When calculated by TDDFT including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with basis set, it has an integral value of ≦45 a.u.×nm.

[0442] According to one embodiment of the present invention, the compound of formula (I) can be prepared by the addition of 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying said hybrid functional B3LYP having a basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level being zero, is in the range of ≧−5.7 eV to ≦−4.7 eV, preferably ≧−5.6 eV to ≦−4.7 eV, more preferably ≧−5.55 eV to ≦−4.75 eV, more preferably ≧−5.50 eV to ≦4.80 eV, and most preferably ≧−5.45 eV to ≦−4.85 eV.

[0443] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦455 nm.max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * The compound of formula (I) has an integral of ≦50 a.u.×nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying the hybrid functional B3LYP with the basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level zero, is in the range ≧−5.45 eV and ≦−4.85 eV.

[0444] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦450 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * The compound of formula (I) has an integral of ≦46 a.u.×nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).* When calculated by applying the hybrid functional B3LYP with the basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level zero, is in the range ≧−5.45 eV and ≦−4.85 eV.

[0445] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦445 nm. max using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * The compound of formula (I) has an integral of ≦45 a.u.×nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying the hybrid functional B3LYP with the basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level being zero, is in the range ≧−5.45 eV and ≦−4.85 eV.

[0446] According to one embodiment of the present invention, the compound of formula (I) is dissolved in DCM at 20° C. for 10 -5 ~10 -4 When measured at a concentration of mol / L, the absorption maximum λ is ≦441. maxusing the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase, and * The compound of formula (I) has an integral of ≦45 a.u.×nm when calculated by TDDFT including the first 30 singlet transitions from optimized geometries using the hybrid functional B3LYP with basis set 6-31G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying the hybrid functional B3LYP with the basis set, the LUMO, expressed in absolute scale with reference to the vacuum energy level zero, is in the range ≧−5.45 eV and ≦−4.85 eV.

[0447] According to one embodiment of the present invention, the group of formula (II) or formula (IIa) is selected from one of the following formulae:

[0448] [ka] JPEG2025500369000157.jpg225169.

[0449] According to one embodiment of the present invention, the group of formula (II) or formula (IIa) is selected from one of the following formulae:

[0450] [ka] JPEG2025500369000159.jpg145169.

[0451] According to one embodiment of the present invention, the group of formula (II) or formula (IIa) is selected from one of the following formulae:

[0452] [ka] .

[0453] According to one embodiment of the present invention, the group of formula (III) or independently of formulas (IIIa) and (IIIb) is selected from one of the following formulae:

[0454] [ka] JPEG2025500369000162.jpg226169JPEG2025500369000163.jpg24169.

[0455] According to one embodiment of the present invention, the group of formula (III) or independently of formulas (IIIa) and (IIIb) is selected from one of the following formulae:

[0456] [ka] JPEG2025500369000165.jpg45169.

[0457] According to one embodiment of the present invention, the group of formula (III) or independently of formulas (IIIa) and (IIIb) is selected from one of the following formulae:

[0458] [ka] .

[0459] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds A1 to A80, and A of the compound of formula (I) 1 , A 2 and A 3 is selected according to the following formula:

[0460] [ka] JPEG2025500369000168.jpg227169JPEG2025500369000169.jpg226169JPEG202 5500369000170.jpg227169JPEG2025500369000171.jpg211169JPEG20255003690 00172.jpg214169JPEG2025500369000173.jpg229169JPEG2025500369000174.j pg213169JPEG2025500369000175.jpg220169JPEG2025500369000176.jpg50169.

[0461] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds A1 to A29, A57, A59, A60, A61, A64, A70 to A72, A77, A78, and A80, and A of the compound of formula (I) is 1 , A 2 and A 3 is selected according to the following formula:

[0462] [ka] JPEG2025500369000178.jpg222169JPEG2025500369000179.jpg231169JPEG2025500369000180.jpg230169JPEG2025500369000181.jpg91169.

[0463] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds A1 to A18, A57, A59, A60, A61, A64, A77, A78, and A80, and A of the compound of formula (I) is 1 , A 2 and A 3 is selected according to the following formula:

[0464] [ka] JPEG2025500369000183.jpg222169JPEG2025500369000184.jpg194169.

[0465] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds B1 to B80:

[0466] [ka] JPEG2025500369000186.jpg193169JPEG2025500369000187.jpg201169JPEG2025500369000188.jpg208169 JPEG2025500369000189.jpg196169JPEG2025500369000190.jpg225169JPEG2025500369000191.jpg189169.

[0467] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds B1 to B29, B56, B57, B59, B60, B61, B64, B67, B70 to B73, B77 B78, and B80:

[0468] [ka] JPEG2025500369000193.jpg193169JPEG2025500369000194.jpg233169JPEG2025500369000195.jpg144169.

[0469] According to one embodiment of the present invention, the compound of formula (I) is selected from compounds B1 to B18, B56, B57, B59, B60, B61, B64, B67, B70 to B73, B77 and B78:

[0470] [ka] JPEG2025500369000197.jpg218169JPEG2025500369000198.jpg141169.

[0471] [CGL Properties] According to one embodiment of the invention, the first charge generating layer has a thickness of ≦30 nm, preferably ≦25 nm, more preferably ≦20 nm, more preferably ≦15 nm, and most preferably ≦10 nm.

[0472] According to one embodiment of the present invention, the first charge generating layer has a thickness of ≧1 nm, preferably ≧2 nm.

[0473] According to one embodiment of the invention, the second charge generating layer has a thickness of ≦30 nm, preferably ≦25 nm, more preferably ≦20 nm, more preferably ≦15 nm, and most preferably ≦10 nm.

[0474] According to one embodiment of the present invention, the second charge generating layer has a thickness of ≧1 nm, preferably ≧2 nm.

[0475] According to one embodiment of the present invention, the first charge generating layer is disposed closer to the cathode layer than the second charge generating layer.

[0476] According to one embodiment of the present invention, the first charge generating layer is in direct contact with the second charge generating layer.

[0477] According to one embodiment of the invention, the charge generating layer has a total thickness of ≦60 nm, preferably ≦55 nm, more preferably ≦50 nm, more preferably ≦45 nm, more preferably ≦40 nm, more preferably ≦35 nm, more preferably ≦30 nm, more preferably ≦25 nm, and most preferably ≦20 nm.

[0478] According to one embodiment of the present invention, the charge generating layer has a thickness of ≧2 nm, preferably ≧4 nm.

[0479] According to one embodiment of the invention, the first charge generating layer and / or the second charge generating layer and / or the compound of formula (I) are non-emissive.

[0480] In the context of this specification, the term "essentially non-emissive" or "non-emissive" means that the contribution of said compound or layer to the visible emission spectrum from the device is less than 10%, preferably less than 5%, of said visible emission spectrum, said visible emission spectrum being an emission spectrum having a wavelength of about ≧380 nm to about ≦780 nm.

[0481] [Organic Electronic Devices] The present invention further relates to an organic electronic device comprising a charge generating layer according to the present invention.

[0482] According to one embodiment of the present invention, the organic electronic device is an electroluminescent device, preferably an organic light emitting diode.

[0483] The present invention further relates to an organic electronic device comprising at least two vertically stacked electroluminescent units according to the present invention and a charge generating layer, each electroluminescent unit comprising at least one light-emitting layer.

[0484] According to the present invention, the term "vertically stacked" particularly means that the electroluminescent units are stacked in a direction essentially perpendicular to said charge generating layer.

[0485] According to one embodiment of the present invention, the electroluminescent device according to the present invention is an organic light emitting diode, in particular a stacked organic light emitting diode.

[0486] According to one embodiment of the present invention, a charge generating layer according to the present invention is disposed between two of the at least two vertically stacked electroluminescent units.

[0487] According to one embodiment of the invention, the organic electronic device is part of a display device.

[0488] According to one embodiment of the invention, the electroluminescent device is a pixel, in particular a pixel of a display device.

[0489] According to one embodiment of the present invention, the organic electronic device comprises at least three or at least four vertically stacked electroluminescent units, each of which comprises at least one light-emitting layer.

[0490] According to one embodiment of the present invention, the organic electronic device comprises at least three or at least four vertically stacked electroluminescent units, each of which comprises at least one light-emitting layer, a hole-transporting layer, and an electron-transporting layer.

[0491] [Display Device] The present invention further relates to a display device comprising a plurality of organic electronic devices according to the present invention, at least two of the plurality of organic electronic devices sharing a common charge generating layer as a charge generating layer, the common charge generating layer being a charge generating layer according to the present invention.

[0492] The present invention further relates to a display device comprising a plurality of organic electronic devices according to the present invention, at least two of the plurality of organic electronic devices sharing a common charge generating layer as a charge generating layer, the common charge generating layer being a charge generating layer according to the present invention.

[0493] The present invention further relates to a display device comprising a plurality of organic electronic devices according to the invention, at least two of the plurality of organic electronic devices sharing as a charge generating layer a common charge generating layer extending across at least two of the plurality of organic electronic devices, Said common charge generating layer is the charge generating layer according to the present invention.

[0494] The present invention further relates to a display device comprising a plurality of organic electronic devices according to the present invention, at least two of the plurality of organic electronic devices sharing as a charge generating layer a common charge generating layer extending across at least two of the plurality of organic electronic devices, the common charge generating layer being a charge generating layer according to the present invention.

[0495] The present invention further relates to a display device comprising a plurality of organic electroluminescent devices according to the present invention, each of the plurality of electroluminescent devices sharing as a charge generating layer a common charge generating layer extending across all of the plurality of organic electroluminescent devices, the common charge generating layer being a charge generating layer according to the present invention.

[0496] The present invention further relates to a display device comprising a plurality of organic electroluminescent devices according to the present invention, each of the plurality of organic electroluminescent devices sharing as a charge generating layer a common charge generating layer extending across all of the plurality of organic electroluminescent devices, the common charge generating layer being a charge generating layer according to the present invention.

[0497] In other words, the present invention relates to a display device comprising a charge generating layer according to the present invention, and a plurality of at least two vertically stacked electroluminescent units arranged horizontally with said charge generating layer, whereby each of said at least two vertically stacked electroluminescent units forms an organic electroluminescent device according to the present invention having a common charge generating layer according to the present invention.

[0498] According to one embodiment of the present invention, the first charge generating layer of the common charge generating layer has a thickness of ≦30 nm, preferably ≦25 nm, more preferably ≦20 nm, more preferably ≦15 nm, and most preferably ≦10 nm.

[0499] According to one embodiment of the present invention, said first charge generating layer of said common charge generating layer has a thickness of ≧1 nm, preferably ≧2 nm.

[0500] According to one embodiment of the present invention, the second charge generating layer of the common charge generating layer has a thickness of ≦30 nm, preferably ≦25 nm, more preferably ≦20 nm, more preferably ≦15 nm, and most preferably ≦10 nm.

[0501] According to one embodiment of the present invention, said second charge generating layer of said common charge generating layer has a thickness of ≧1 nm, preferably ≧2 nm.

[0502] According to one embodiment of the present invention, the first charge generating layer is disposed closer to the cathode layer than the second charge generating layer in the common charge generating layer.

[0503] According to one embodiment of the present invention, the first charge generating layer is in direct contact with the second charge generating layer in the common charge generating layer.

[0504] According to one embodiment of the present invention, the common charge generating layer has a total thickness of ≦60 nm, preferably ≦55 nm, more preferably ≦50 nm, more preferably ≦45 nm, more preferably ≦40 nm, more preferably ≦35 nm, more preferably ≦30 nm, more preferably ≦25 nm, and most preferably ≦20 nm.

[0505] According to one embodiment of the present invention, said common charge generating layer has a thickness of ≧2 nm, preferably ≧4 nm.

[0506] According to one embodiment of the present invention, each electroluminescent device comprises at least three or at least four vertically stacked electroluminescent units, each of which comprises at least one light-emitting layer.

[0507] According to one embodiment of the invention, the display device is an active matrix display.

[0508] According to one embodiment of the present invention, the display device is an OLED display.

[0509] According to one embodiment of the invention, the display device includes a drive circuit configured to individually drive the pixels of the plurality of pixels.

[0510] [Further Layers] According to the invention, the organic electroluminescent device or the display device (further referred to as organic electronic device) may comprise further layers in addition to those already mentioned above. Exemplary embodiments of the respective layers are described below: substrate The substrate can be any substrate commonly used in the manufacture of electronic devices (such as organic light-emitting diodes). If light is emitted through the substrate, the substrate must be a transparent or semi-transparent material (e.g., a glass substrate or a transparent plastic substrate). If light is emitted from the top surface, the substrate can be both transparent and non-transparent materials (e.g., a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate).

[0511] anode layer The anode layer can be formed by evaporating or sputtering the material used to form the anode layer. The material used to form the anode layer can be a high work function material to facilitate hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent electrode or a reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO) and zinc oxide (ZnO), can be used to form the anode electrode. The anode layer can also be formed using a metal, typically silver (Ag), gold (Au), or a metal alloy.

[0512] Hole injection layer A hole injection layer (HIL) can be formed on the anode layer by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, and the like. When vacuum deposition is used to form the HIL, deposition conditions can vary depending on the compounds used to form the HIL, as well as the desired structure and thermal properties of the HIL. However, in general, conditions for vacuum deposition include a deposition temperature of 100°C to 500°C, a deposition pressure of 10 -8 ~10 -3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 nm / sec to 10 nm / sec.

[0513] When the HIL is formed using spin coating or printing, the coating conditions can vary depending on the compounds used to form the HIL and the desired structural 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. Coating is followed by a heat treatment to remove the solvent.

[0514] The HIL may be formed of any compound commonly used to form HILs. Examples of compounds that may 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-styrenesulfonic acid) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), and polyaniline) / poly(4-styrenesulfonic acid (PANI / PSS).

[0515] The HIL may comprise or consist of a p-type dopant, which may be selected from, but is not limited to, tetrafluoro-tetracyanoquinone dimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile, or 2,2',2''-(cyclopropane-1,2,3-triylidene) tris(2-(p-cyanotetrafluorophenyl)acetonitrile). The HIL may be selected from hole-transporting matrix compounds doped with p-type dopants. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc), which has a HOMO level of about -5.2ev and a LUMO level of about -5.2ev doped with tetrafluoro-tetracyanoquinone dimethane (F4TCNQ); zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO=-5.2eV); α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile. The p-type dopant concentration can be selected from 1% to 20% by weight, more preferably from 3% to 10% by weight.

[0516] However, according to a preferred embodiment of the invention, said HIL comprises a compound of formula (I) as defined above.

[0517] According to a preferred embodiment of the present invention, the HIL may comprise the same compound of formula (I) as the p-type charge generating layer.

[0518] According to a preferred embodiment of the invention, the HIL may comprise a substantially covalent matrix compound as described above.

[0519] According to a preferred embodiment of the present invention, the HIL may comprise a compound of formula (I) as defined above, and a compound of formula (IV) or (V) as defined above.

[0520] According to a preferred embodiment of the present invention, the p-type charge generating layer and the hole injection layer may comprise the same substantially covalent matrix compound.

[0521] The thickness of the HIL may be in the range of about 1 nm to about 100 nm, for example, in the range of about 1 nm to about 25 nm, When the HIL thickness is in this range, the HIL can have excellent hole injection properties without a substantial penalty in driving voltage.

[0522] Hole transport layer A hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions can be similar to the conditions for forming the HIL. However, the conditions of the vacuum deposition or the solution deposition may differ depending on the compounds used to form the HTL.

[0523] The HTL may be formed of any compound commonly used to form an HTL. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem.Rev.2007, 107,953-1010, which is incorporated by reference. Examples of compounds that can be used to form the HTL include carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole); benzidine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds (such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA)). Among these compounds, TCTA can transport holes and inhibit excitons from diffusing into the EML.

[0524] According to one embodiment of the present invention, the hole transport layer may comprise the substantially covalent matrix compound described above.

[0525] According to one embodiment of the present invention, the hole transport layer may comprise a compound of formula (VI) or (VII) as described above.

[0526] According to a preferred embodiment of the present invention, the hole injection layer and the hole transport layer may comprise the same compound of formula (VI) or (VII) above.

[0527] According to a preferred embodiment of the present invention, the p-type charge generating layer, the hole injection layer and the hole transport layer may comprise the same substantially covalent matrix compound.

[0528] According to a preferred embodiment of the present invention, the p-type charge generating layer, the hole injection layer and the hole transport layer may comprise the same compound of formula (IV) or (V) above.

[0529] 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. The preferred thickness of the HTL may be 170 nm to 200 nm.

[0530] When the HTL thickness is in this range, the HTL can have excellent hole transport properties without a substantial penalty in driving voltage.

[0531] electron blocking layer The function of the electron blocking layer (EBL) is to block electrons from migrating from the light emitting layer to the hole transport layer, thereby confining the electrons to the light emitting layer, thereby improving efficiency, operating voltage and / or lifetime. Typically, the electron blocking layer comprises a triarylamine compound. The triarylamine compound may have a LUMO level closer to the vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level further away from the vacuum level than the HOMO level of the hole transport layer. The thickness of the electron blocking layer may be selected between 2 and 20 nm.

[0532] When the electron blocking layer has a high triplet level, the electron blocking layer may be referred to as a triplet control layer.

[0533] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or blue light-emitting layer is used. This can increase the light emission efficiency from the phosphorescent light-emitting layer. The triplet control layer is selected from triarylamine compounds having triplet levels higher than the triplet levels of the phosphorescent emitters of the adjacent light-emitting layers. Compounds suitable for the triplet control layer, in particular the triarylamine compounds, are described in EP 2 722 908 A1.

[0534] Photoactive layer (PAL) According to one embodiment of the present invention, the organic electronic device may further include a photoactive layer, the photoactive layer being disposed between the anode layer and the cathode layer.

[0535] The photoactive layer converts electrical current into photons or photons into electrical current.

[0536] 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 deposition or coating conditions can be similar to the conditions for forming the HIL. However, the deposition and coating conditions may differ depending on the compounds used to form the PAL.

[0537] According to one embodiment of the invention, the photoactive layer does not comprise a compound of formula (I).

[0538] The photoactive layer may be a light-emitting layer or a light-absorbing layer.

[0539] Emitting layer (EML) According to one embodiment of the present invention, the organic electronic device may further include an emissive layer, the emissive layer being disposed between the anode layer and the cathode layer.

[0540] 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 deposition and coating conditions can be similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the EML.

[0541] According to one embodiment of the present invention, the light-emitting layer does not comprise a compound of formula (I).

[0542] The light-emitting layer (EML) can be formed by combining a host and an emitter dopant. Examples of the host include Alq3,4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), and bis(2-(2-hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).

[0543] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit via the thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their high efficiency. The emitter may be a small molecule or a polymer.

[0544] Examples of red emitter dopants include, but are not limited to, PtOEP, Ir(piq)3, and Btp2lr(acac). These compounds are phosphorescent emitters, but fluorescent red emitter dopants can also be used.

[0545] Examples of phosphorescent green emitter dopants include Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0546] Examples of phosphorescent blue emitter dopants include F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and ter-fluorene. 4.4'-Bis(4-diphenylamiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitting dopants.

[0547] The amount of the emitter dopant may range from about 0.01 parts by weight to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, the emissive layer may be made of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is in this range, the EML may have excellent luminescence without a substantial penalty in driving voltage.

[0548] Hole Blocking Layer (HBL) To prevent holes from diffusing into the ETL, a hole-blocking layer (HBL) may be formed on the EML by using vacuum deposition, spin-coating, slot-die coating, printing, casting, LB deposition, etc. When the EML contains a phosphorescent dopant, the HBL can also have a triplet exciton blocking function.

[0549] The HBL may also be referred to as an auxiliary ETL or a-ETL.

[0550] When the HBL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be the same as those for forming the HIL. However, depending on the compound used to form the HBL, the deposition and coating conditions may be different. Any compound commonly used to form the HBL can be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and azine derivatives, preferably triazine derivatives or pyrimidine derivatives.

[0551] The HBL may have a thickness 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 HBL thickness is in this range, the HBL can have excellent hole blocking properties Without a substantial penalty in driving voltage.

[0552] Electron transport layer (ETL) The organic electronic device according to the present invention can further comprise an electron transport layer (ETL).

[0553] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a triazine compound or a pyrimidine compound.

[0554] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali organic complexes, preferably LiQ.

[0555] The thickness of the ETL may be in the range of about 15 nm to about 50 nm, such as about 20 nm to about 40 nm, where the thickness of the EIL is in this range, and the ETL can have satisfactory electron injection properties without a substantial penalty in drive voltage.

[0556] According to another embodiment of the present invention, the organic electronic device may further comprise a hole blocking layer and an electron transport layer, the hole blocking layer and the electron transport layer comprising an azine compound. Preferably, the azine compound is a triazine compound.

[0557] According to one embodiment of the present invention, the n-type charge generating layer is sandwiched between and in contact with the electron transport layer and the p-type charge generating layer.

[0558] According to one embodiment of the present invention, the n-type charge generating layer is sandwiched between and in contact with the electron transport layer and the p-type charge generating layer, and the n-type charge generating layer and / or the electron transport layer comprises an azine compound. Particularly improved performance may be obtained.

[0559] According to one embodiment of the present invention, the n-type charge generating layer is sandwiched between and in contact with the electron transport layer and the p-type charge generating layer; the electron transport layer is sandwiched between and in contact with the first light emitting layer and the n-type charge generating layer; and the n-type charge generating layer and / or the electron transport layer comprises an azine compound. Particularly improved performance may be obtained.

[0560] According to one embodiment of the present invention, the n-type charge generating layer is sandwiched between and in contact with the electron transport layer and the p-type charge generating layer; the electron transport layer is sandwiched between and in contact with the first light emitting layer and the n-type charge generating layer; the n-type charge generating layer comprises a phenanthroline compound, and the electron transport layer comprises an azine compound, preferably a triazine compound or a pyrimidine compound. Particularly improved performance may be obtained.

[0561] Electron injection layer (EIL) An optional EIL may facilitate the injection of electrons from the cathode and may be formed directly on the ETL, preferably on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg, as 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 may vary depending on the material used to form the EIL.

[0562] The thickness of the EIL may be in the range of about 0.1 nm to about 10 nm, such as about 0.5 nm to about 9 nm, in which case the EIL may have satisfactory electron injection properties without a substantial penalty in drive voltage.

[0563] Cathode Layer The cathode layer is formed on the ETL or any EIL. The cathode layer 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 layer 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), etc. Alternatively, the cathode electrode can be formed of a transparent conductive oxide, such as ITO or IZO.

[0564] The thickness of the cathode layer may 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 layer is in the range of about 5 nm to about 50 nm, the cathode layer may be transparent or semi-transparent even if formed from a metal or metal alloy.

[0565] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0566] Organic Light Emitting Diode (OLED) The organic electronic device according to the present invention may be an organic light emitting device.

[0567] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising an anode layer formed on a substrate, a charge generating layer according to the present invention, at least one light emitting layer, and a cathode layer.

[0568] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising a substrate, an anode layer formed on the substrate, a charge generating layer according to the present invention, at least one light emitting layer, and a cathode layer.

[0569] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising an anode layer formed on a substrate, a charge generating layer according to the present invention, at least a first light emitting layer and a second light emitting layer, and a cathode layer, wherein the charge generating layer is disposed between the first light emitting layer and the second light emitting layer.

[0570] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising a substrate, an anode layer formed on the substrate, a charge generating layer according to the present invention, at least a first light emitting layer and a second light emitting layer, and a cathode layer, wherein the charge generating layer is disposed between the first light emitting layer and the second light emitting layer.

[0571] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising: a substrate; an anode layer formed on the substrate; a charge generating layer according to the present invention; at least a first light emitting layer and a second light emitting layer; and a cathode layer, wherein the charge generating layer is disposed between the first light emitting layer and the second light emitting layer, and the first charge generating layer is disposed closer to the cathode layer than the second charge generating layer.

[0572] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising: a substrate; an anode layer formed on the substrate; a hole injection layer, the hole injection layer being in direct contact with the anode layer; a charge generating layer according to the present invention; at least a first light emitting layer and a second light emitting layer; and a cathode layer, wherein the charge generating layer is disposed between the first light emitting layer and the second light emitting layer, and the first charge generating layer is disposed closer to the cathode layer than the second charge generating layer.

[0573] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising an anode layer formed on a substrate, a charge generating layer according to the present invention, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode layer.

[0574] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising a substrate, an anode layer formed on the substrate, a charge generating layer, the charge generating layer according to the present invention, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode layer.

[0575] According to another aspect of the present invention, there is provided an OLED comprising an anode layer formed on a substrate, a charge generating layer according to the present invention, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and a cathode layer.

[0576] According to another aspect of the present invention, there is provided an OLED comprising a substrate, an anode layer formed on the substrate, a charge generating layer according to the present invention, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and a cathode layer.

[0577] According to another aspect of the present invention, there is provided an OLED comprising an anode electrode formed on the substrate, a charge generating layer according to the present invention, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, an electron injection layer, and a cathode electrode.

[0578] According to another aspect of the present invention, there is provided an OLED comprising a substrate, an anode electrode formed on the substrate, a charge generating layer according to the present invention, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, an electron injection layer, and a cathode electrode.

[0579] According to various embodiments of the present invention, between the layers mentioned above, there may be provided an OLEDs layer disposed on the substrate or on the top electrode.

[0580] According to one embodiment, the OLED may include a layer structure of a substrate disposed adjacent to an anode layer, the anode electrode disposed adjacent to a first hole injection layer, the first hole injection layer disposed adjacent to a first hole transport layer, the first hole transport layer disposed adjacent to a first electron blocking layer, the first electron blocking layer disposed adjacent to a first light emitting layer, the first light emitting layer disposed adjacent to a first electron transport layer, and the first electron transport layer being a first charge generating layer according to the present invention. a second charge generating layer, the second charge generating layer being disposed adjacent to a first charge generating layer of the charge generating layer according to the present invention, the first charge generating layer of the charge generating layer according to the present invention being disposed adjacent to a second hole transport layer, the second hole transport layer being disposed adjacent to a second electron blocking layer, the second electron blocking layer being disposed adjacent to a second light-emitting layer, and an optional electron transport layer and / or optional injection layer being disposed between the second light-emitting layer and the cathode electrode.

[0581] The present invention further relates to a compound of formula (XI)

[0582] [ka]

[0583] In the formula (XI), A 1 is selected from the group of formula (XIIa)

[0584] [ka]

[0585] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; X 5 CR 5 or N; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 2 , R 3 and R 5 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 , R 3 and R 5 If any of X exists, 1 , X 2 , X 3 , and X 5 is not N; In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0586] [ka]

[0587] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, wherein said substituents on Ar are independently selected from electron withdrawing groups, CN, partially or perfluorinated C1-C6 alkyl, -NO2, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18It is selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN.

[0588] According to one embodiment of the present invention, the compound of formula (XI) is selected from the group consisting of the compounds of formula (XI) and the compounds of formula (XI) 1 , A 2 and A 3 is selected according to:

[0589] [ka] .

[0590] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0591] [ka]

[0592] In the formula (XI), A 1 is selected from the group of formula (XIIa)

[0593] [ka]

[0594] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; X 5 CR 5 or N; R 1(when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 2 , R 3 and R 5 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 , R 3 and R 5 If any of X exists, 1 , X 2 , X 3 , and X 5 is not N; and wherein in formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0595] [ka]

[0596] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, wherein said substituents on Ar are independently selected from electron withdrawing groups, CN, partially or perfluorinated C1-C6 alkyl, -NO2, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN; wherein said compound of formula (XI) comprises at least 5 CN groups; In the formula (XIIa), X n is N and X n+1 CR n+1 If so, then R n+1 cannot be CN (n = 1–4); In the formula (XIIa), X n is N and X n-1 CR n-1 If so, then R n-1 cannot be CN (n = 1 to 4).

[0597] According to one embodiment of the present invention, the charge generating layer, the organic electroluminescent device and / or the display device according to the present invention comprises, as the compound of formula (I), a compound according to formula (XI) above.

[0598] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0599] [ka]

[0600] Here, A 1 is selected from formula (XIIb)

[0601] [ka]

[0602] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1(when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, halogen, -NO2, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3 If any of X exists, 1 , X 2 , and X 3 is not N; In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0603] [ka]

[0604] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, said substituents on Ar being independently selected from electron withdrawing groups, CN, partially or perfluorinated C1-C6 alkyl, -NO2, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 It is selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN.

[0605] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0606] [ka]

[0607] Here, A 1 is selected from formula (XIIb)

[0608] [ka]

[0609] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3 If any of X exists, 1 , X 2 , and X 3 is not N; However, R 1 and R 4 exists and R 1 Or R4 If only CN is selected, then R 2 , R 3 and the remaining R 1 Or R 4 is independently selected from CN, and partially or perfluorinated C1-C8 alkyl, D, or R 2 and R 3 is selected from CN, partially or perfluorinated C2-C8 alkyl, halogen, Cl, FD, or H, or R 2 , R 3 and the remaining R 1 Or R 4 is independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D; Or, however, R 1 and R 4 exists and R 1 Or R 4 When only perfluorinated C1 is selected, R 2 and R 3 are independently selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D, or H, or R 2 , R 3 and the remaining R 1 Or R 4 is selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D; Or, but X 1 is N and R 4 If is selected from CN, then R 2 , R 3 is selected from H or D (if present), or R 2 and R 3 are independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, provided that R 2 and R 3 cannot both be CN, or R 2is selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D or H; Or, but X 1 is N and R 4 When R is selected from perfluorinated C alkyl, 2 is selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D, or R 3 is selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, or R 2 and R 3 are independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, or R 2 and R 3 is independently selected from H or D (if present); In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0610] [ka]

[0611] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, said substituents on Ar being independently selected from CN, partially or perfluorinated C1-C6 alkyl, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 It is selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN.

[0612] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0613] [ka]

[0614] Here, A 1 is selected from formula (XIIb)

[0615] [ka]

[0616] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3 If any of X exists, 1 , X 2 , and X 3 is not N; However, R 1 and R 4 exists and R 1Or R 4 If only CN is selected, then R 2 , R 3 and the remaining R 1 Or R 4 is independently selected from CN and partially or perfluorinated C1-C8 alkyl, D, or R 2 and R 3 is selected from CN, partially or perfluorinated C2-C8 alkyl, halogen, Cl, FD, or H, or R 2 , R 3 and the remaining R 1 Or R 4 is independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D; Or, however, R 1 and R 4 exists and R 1 Or R 4 When only perfluorinated C1 is selected, R 2 and R 3 are independently selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D, or H, or R 2 , R 3 and the remaining R 1 Or R 4 is selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D; Or, but X 1 is N and R 4 If is selected from CN, then R 2 , R 3 is selected from H or D (if present), or R 2 and R 3 are independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, provided that R 2 and R 3 cannot both be CN, or R 2is selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D or H; Or, but X 1 is N and R 4 When R is selected from perfluorinated C alkyl, 2 is selected from partially or perfluorinated C2-C8 alkyl, halogen, Cl, F, D, or R 3 is selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, or R 2 and R 3 are independently selected from CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, or R 2 and R 3 is independently selected from H or D (if present); In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0617] [ka]

[0618] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C1-C6 alkyl, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN; Here, the following formula (XIIb) is excluded:

[0619] [ka] .

[0620] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0621] [ka]

[0622] Here, A 1 is selected from formula (XIIb)

[0623] [ka]

[0624] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, halogen, -NO2, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3If any of X exists, 1 , X 2 , and X 3 is not N; In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0625] [ka]

[0626] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, said substituents on Ar being independently selected from electron withdrawing groups, CN, partially or perfluorinated C1-C6 alkyl, -NO2, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN; In this regard, the following formula (XIIb) is excluded:

[0627] [ka]

[0628] wherein said compound of formula (XI) is not a compound according to the following formula:

[0629] [ka] .

[0630] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XI)

[0631] [ka]

[0632] A 1 is selected from formula (XIIb)

[0633] [ka]

[0634] Where: X 1 CR 1 or N; X 2 CR 2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, halogen, -NO2, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3 If any of X exists, 1 , X 2 , and X 3 is not N; In the formula (XI), A 2 and A 3 are independently selected from formula (XIII):

[0635] [ka]

[0636] Ar is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 18 heteroaryl, said substituents on Ar being independently selected from electron withdrawing groups, CN, partially or perfluorinated C1-C6 alkyl, -NO2, halogen, Cl, F, D; and R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN; In this regard, the following formula (XIIb) is excluded:

[0637] [ka]

[0638] The compound of formula (XI) is not a compound according to the formula:

[0639] [ka] .

[0640] According to one embodiment of the present invention, the compound of formula (XI) is selected from the compounds of formula (XIV)

[0641] [ka]

[0642] Where: X 1 CR 1 or N; X 2 CR2 or N; X 3 CR 3 or N; X 4 CR 4 Selected from; R 1 (when present) is selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 2 and R 3 (when present) are independently selected from an electron withdrawing group, CN, partially or perfluorinated C1-C8 alkyl, -NO2, halogen, Cl, F, D or H; R 4 is selected from CN, and partially or perfluorinated C1-C8 alkyl; R 1 , R 2 and R 3 If any of X exists, 1 , X 2 , and X 3 is not N; R' is a substituted or unsubstituted C6-C 18 Aryl or C3-C 18 selected from heteroaryl, partially or perfluorinated C1-C8 alkyl, halogen, F or CN; Where: each X 1 ' is a CR 1 ' or N; each X 2 ' is a CR 2 ' or N; each X 3 ' is a CR 3 ' or N; each X 4 ' is a CR 4 ' or N; each X 5 ' is a CR 5 ' or N;grl Each R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ' (when present) is independently selected from an electron withdrawing group, F, CN, partially or perfluorinated C1-C8 alkyl, halogen, Cl, F, D, or H, whereby R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ', if any of the corresponding X 1 ', X 2 ', X 3 ', X 4 ' and X 5 ' is not N.

[0643] According to one embodiment of the present invention, X 1 CR 1 When selected from 1 is selected from electron withdrawing groups, F.CN, and partially or perfluorinated C1-C8 alkyl; According to one embodiment of the present invention, X 1 CR 1 When selected from 1 is selected from F, CN, and partially or perfluorinated C1-C8 alkyl; According to one embodiment of the present invention, X 1 CR 1 When selected from 1 is selected from CN, and partially or perfluorinated C1-C8 alkyl.

[0644] According to one embodiment, R 2 and R 3 (when present) are independently selected from partially or perfluorinated C1-C8 alkyl, CF3, -NO2, halogen, Cl, F, D or H; X 3 If N, then X 4 CR 4 R 4cannot be a CN, and X 2 is N and X1 is CR 1 If so, then R 1 cannot be a CN.

[0645] According to one embodiment of the present invention, R 4 is F, CN, and partially or perfluorinated C1-C8 alkyl.

[0646] According to one embodiment of the present invention, R 4 is CN, and partially fluorinated or perfluorinated C1-C8 alkyl.

[0647] According to one embodiment of the present invention, X 4 ' is a CR 4 ' is selected from.

[0648] According to one embodiment of the present invention, X 5 ' is selected from N.

[0649] According to one embodiment of the invention, the substituents on Ar are independently selected from CN, partially or perfluorinated C1-C6 alkyl, -NO2, F.

[0650] According to one embodiment of the present invention, R' is selected from CN.

[0651] According to one embodiment of the present invention, said compound of formula (XI) contains at least 5 CN groups, preferably at least 6 CN groups.

[0652] According to one embodiment of the present invention, the compound of formula (XI) contains 5 to 9 CN groups; preferably 6 to 9 CN groups.

[0653] According to one embodiment, R 2 and R 3 (when present) are independently selected from partially or perfluorinated C1-C8 alkyl, CF3, -NO2, halogen, Cl, F, D or H; X3 If N, then X 4 CR 4 R 4 cannot be CN, and X 2 is N and X 1 CR 1 If so, then R 1 cannot be CN, and said compound of formula (XI) contains at least 5 CN groups.

[0654] According to one embodiment of the present invention, A in the compound according to formula (XI) 1 is selected from one of the following formulas:

[0655] [ka] .

[0656] According to one embodiment of the present invention, A in the compound according to formula (XI) 1 is selected from one of the following formulas:

[0657] [ka] .

[0658] According to one embodiment of the present invention, A in the compound according to formula (XI) 1 is selected from one of the following formulas:

[0659] [ka]

[0660] Preferably, said compound of formula (XI) contains at least 5 CN groups, more preferably at least 6 CN groups.

[0661] According to one embodiment of the present invention, A in the compound according to formula (XI) 1 is selected from one of the following formulas:

[0662] [ka]

[0663] .

[0664] According to one embodiment of the present invention, A in the compound according to formula (XI) 1 is selected from one of the following formulas:

[0665] [ka]

[0666] Preferably, said compound of formula (XI) contains at least 5 CN groups, more preferably at least 6 CN groups.

[0667] According to one embodiment of the present invention, A in the compound according to formula (XI) 2 and A 3 is independently selected from one of the following formulas:

[0668] [ka] JPEG2025500369000233.jpg126169.

[0669] According to one embodiment of the present invention, A in the compound according to formula (XI) 2 and A 3 is independently selected from one of the following formulas:

[0670] [ka] JPEG2025500369000235.jpg151169.

[0671] According to one embodiment of the present invention, A in the compound according to formula (XI) 2 and A 3is independently selected from one of the following formulas:

[0672] [ka] JPEG2025500369000237.jpg126169

[0673] Preferably, said compound of formula (XI) contains at least 5 CN groups, more preferably at least 6 CN groups.

[0674] According to one embodiment of the present invention, the compound of formula (XI) is selected from C1 to C23 and C25 to C35 compounds, and A of the compound of formula (XI) 1 , A 2 and A 3 is selected according to the following formula:

[0675] [ka] JPEG2025500369000239.jpg221169JPEG2025500369000240.jpg227169JPEG2025500369000241.jpg194169.

[0676] According to one embodiment of the present invention, the compound of formula (XI) is selected from C2-C4, C6-C15, C17-C23 and C25-C35 compounds.

[0677] According to one embodiment of the present invention, the compound of formula (XI) is selected from E1 to E35:

[0678] [ka] JPEG2025500369000243.jpg225169JPEG2025500369000244.jpg141169.

[0679] According to one embodiment of the present invention, the compound of formula (XI) is selected from E2 to E4, E6 to E15, E17 to E22 and E24 to E35.

[0680] Hereinafter, the embodiments will be described in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Hereinafter, reference will be made in detail to exemplary embodiments.

[0681] Description of the drawings The aforementioned components, as well as the components claimed and used according to the invention in the described embodiments, are not subject to special exceptions with regard to their size, shape, material selection and technical concept, so that selection criteria known in the relevant art may be applied without limitation.

[0682] Additional details, features and advantages of the subject matter of the present invention are disclosed in the dependent claims and the following description of the figures, which exemplarily show preferred embodiments according to the present invention. However, any embodiment does not necessarily represent the full scope of the present invention, and therefore, reference is made to the claims and this specification to interpret the scope of the present 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 set forth in the claims.

[0683] FIG. 1 is a schematic cross-sectional view of an OLED including a charge generating layer in accordance with an illustrative embodiment of the invention.

[0684] FIG. 2 is a schematic cross-sectional view of a stacked OLED including a charge generating layer according to an exemplary embodiment of the invention.

[0685] The figures will now be described in more detail with reference to examples, but the present disclosure is not limited to the figures below.

[0686] As used herein, when a first element is referred to as being formed or disposed "on" or "onto" 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 "directly onto" a second element, no other elements are disposed therebetween.

[0687] FIG. 1 is a schematic cross-sectional view of an OLED 100 according to an exemplary embodiment of the invention.

[0688] 1, the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL1) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an n-type charge generation layer (n-CGL) 185, a p-type charge generation layer (p-GCL) 135 which may include a compound of Formula (I), a second hole transport layer (HTL2) 141, and an electron injection layer (EIL) 180, and a cathode layer 190. The HIL may include a compound of Formula (I).

[0689] Figure 2 is a schematic cross-sectional view of a stacked OLED 100 according to another exemplary embodiment of the present invention. Figure 2 differs from Figure 1 in that the OLED 100 in Figure 1 further includes a second light-emitting layer.

[0690] Referring to FIG. 2 , the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emissive layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generating layer (n-CGL) 185, a p-type charge generating layer (p-GCL) 135 which may include a compound of Formula (I), a second hole transport layer (HTL) 141, a second electron blocking layer (EBL) 146, a second emissive layer (EML) 151, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, an electron injection layer (EIL) 180, and a cathode layer 190. The HIL may comprise a compound of formula (I).

[0691] In the above description, the method of making an OLED 100 of the present invention starts with a substrate 110 having an anode layer 120 formed thereon, and then forming, in that order or in reverse order, a hole injection layer 130, a first hole transport layer 140, an optional first electron blocking layer 145, a first light-emitting layer 150, an optional first hole blocking layer 155, an optional at least one first electron transport layer 160, an n-CGL 185, a p-CGL 135, a second hole transport layer 141, an optional second electron blocking layer 146, a second light-emitting layer 151, an optional second hole blocking layer 156, an optional at least one second electron transport layer 161, an optional electron injection layer (EIL) 180, and a cathode layer 190 on the anode layer 120.

[0692] 1 and 2, an encapsulation and / or capping layer may be further formed on the cathode layer 190 to encapsulate the organic electronic device 100. Additionally, various other modifications may be made.

[0693] One or more exemplary embodiments of the present invention will now be described in detail with reference to the following examples, which are not intended to limit the spirit and scope of the one or more exemplary embodiments of the present invention.

[0694] Detailed Description The invention is further illustrated by the following examples, which are illustrative only and non-binding.

[0695] Compounds of formula (I) can be prepared as described in EP2180029A1 and WO2016097017A1.

[0696] [UV-VIS absorption measurement in solution] Experimental absorption spectra were recorded on a Shimadzu UV-2401 PC series spectrophotometer. For sample preparation, the material is weighed into an aluminum crucible and inserted into a 25 mL volumetric flask. The associated microbalance allows readings of mass changes in the range of 1-2 μg. The flask is then filled up to the mark with dichloromethane (spectroscopy grade, transmittance ≥ 90% at λ ≥ 248 nm according to the manufacturer) and shaken until the material is completely dissolved, obtaining a solution with a concentration of 10-4-10-5 mol / L. For measurements, the solution is placed in a standard cuvette (Hellma 110-QS: quartz, d = 10 mm, with a PTFE stopper). Spectra are recorded with a slit width of 1 nm, a sampling interval of 0.5 nm, and an ambient temperature of 20 °C. From all spectra, the background absorption of the pure solvent measured immediately before the measurement under the same measurement conditions is subtracted. The results are shown in Table 1.

[0697] [Measurement of light absorption rate of p-type charge generation layer] Mixed films of N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine and p-dopants according to Table 2 were prepared on quartz substrates (EN08, ≥99.98% SiO2, GVB GmbH) with a thickness of 35 nm by thermal evaporation using a vacuum system (Cluster Tool, Sunic System Ltd.) at a deposition rate of 1 Å / s and a pressure of approximately 3e-7 mbar. The samples are kept in a glove box with a pure nitrogen atmosphere until measurements are performed (maximum 1 h air exposure). Reflectance and transmittance are measured using a Filmetrics F10-RT Spectrometer with a spectral range of 380 nm to 1050 nm. Blank quartz substrates are used for reflectance standards. Absorbance is automatically calculated by subtracting the reflectance and transmittance values ​​from 100%. The results are shown in Table 2.

[0698] [Glass transition temperature] The glass transition temperature (Tg) is measured under nitrogen on a Mettler Toledo DSC 822e differential scanning calorimeter at a heating rate of 10 K per minute as described in DIN EN ISO 11357 published in March 2010.

[0699] [Calculated HOMO and LUMO] The HOMO and LUMO were calculated using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometries, as well as the HOMO and LUMO energy levels of the molecular structures, were calculated using the 6-31G * The conformation was determined by applying the hybrid functional B3LYP of the basis set. When more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0700] [Calculated absorption area or maximum absorption amount] Calculations were performed with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

[0701] The LUMO and HOMO energies, and the resulting HOMO-LUMO gap, are 6-31G in the gas phase. * Calculations were performed using the hybrid functional B3LYP with the basis set . Using the optimized geometry thus obtained, TDDFT calculations were performed in the gas phase applying the hybrid functional PBE0 with the def2-SVP basis set, including the first 30 singlet transitions. The calculated singlet transitions were used to calculate the absorption spectrum by applying a Gaussian fit (λ = 215-850 nm, SD = 20,200 sampling points) excluding transitions below 350 nm.

[0702] To calculate the general absorption in the relevant wavelength region (λ = 400-650 nm, blue and green emission), integrals under the calculated UV TDDFT spectra were determined.

[0703] [Calculated bond dissociation energies (BDE)] All calculations were performed with the program package ORCA Version 5.0.3-f.1 (Department of theory and spectroscopy, Max Planck Institute fur Kohlenforschung Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany).

[0704] Homolytic bond dissociation energy (BDE) is the amount of energy required to break one mole of a covalently bonded gas into a pair of radicals and was calculated according to a reported procedure (J. Phys. Chem. A, 1999, 103, 11, 1653-1661).

[0705] Molecular geometries were optimized in the gas phase using DFT functions BP86 and Def2-SVP basis set, and the lower energy conformer was selected when more than one conformer was available. The optimized geometries were identified as local minima by frequency analysis.

[0706] From the optimized geometry, ΔG (BP86 / Def2SVP) and electron energy (BP86 / Def2SVP) In the second calculation, the electronic energy (B3LYP / Def2TZVP) was obtained from single-point calculations using the DFT functional B3LYP and the Def2-TZVP basis set in the gas phase.

[0707] The energy correction values ​​were obtained as follows: (ΔG (BP86 / Def2SVP) -Electron Energy (BP86 / Def2SVP) ) + electron energy (B3LYP / Def2TZVP) .

[0708] [General procedure for manufacturing OLED] For bottom emission devices, see Table 2. 15 Ω / cm with 90 nm ITO 2 A glass substrate (available from Corning) was cut to a size of 50 mm×50 mm×0.7 mm, ultrasonically cleaned in isopropyl alcohol for 5 minutes, then in pure water for 5 minutes, and cleaned again by UV ozone for 30 minutes to prepare an anode.

[0709] Next, N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine was vacuum-deposited with 12 volume % of the compound according to formula (I) or the comparative compound according to Table 2 to form a hole injection layer having a thickness of 10 nm.

[0710] Next, N-([1,1′-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluorene]-2-amine was vacuum-deposited to form a first hole transport layer having a thickness of 130 nm.

[0711] Next, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′:4′,1″-terphenyl]-4-amine was vacuum-deposited onto the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0712] Then, 97 vol.% H09 (Sun Fine Chemicals, Korea) as an EML host and 3 vol.% BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant were evaporated onto the EBL to form a first blue-emitting EML with a thickness of 20 nm.

[0713] Next, 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was vacuum-deposited to form a first hole-blocking layer having a thickness of 25 nm.

[0714] Next, 6-31G was synthesized in the gas phase by co-evaporation of 99 vol. % of (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracen-9-yl)phenyl)dimethylphosphine oxide) using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * An an-type CGL having a thickness of 15 nm and a LUMO energy level of −1.80 eV expressed in absolute scale with reference to the vacuum energy level being zero, as calculated by applying the hybrid functional B3LYP with basis set and 1 vol% Yb, is formed on ETL1.

[0715] Next, a p-type CGL having a thickness of 20 nm is formed on the first n-type CGL by co-evaporating 20 volume % of N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine and a compound according to Formula (I) or a comparative example according to Table 3.

[0716] Next, a second hole transport layer having a thickness of 11 nm is formed on the first p-type CGL by evaporating N-([1,1′-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluorene]-2-amine.

[0717] Next, a second electron blocking layer having a thickness of 5 nm is formed on the second hole transport layer by evaporating N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine.

[0718] Then, 97 vol. % H09 (Sun Fine Chemicals, Korea) as an EML host and 3 vol. % BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant were evaporated onto the second EBL to form a second blue-emitting EML with a thickness of 20 nm.

[0719] Next, a second hole-blocking layer with a thickness of 10 nm was formed on the second blue-emitting EML by vacuum deposition of 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0720] Next, 50 wt % of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt % of LiQ were vacuum-deposited onto the second hole-blocking layer to form a second electron-transporting layer having a thickness of 25 nm.

[0721] Al to 10 -7 Evaporate at a rate of 0.01-1 Å / s at 100 mbar to form a cathode with a thickness of 100 nm.

[0722] To evaluate the performance of embodiments of the present invention compared to the prior art, the current efficiency is measured at 20°C. The current-voltage characteristic is determined by applying a voltage in V and measuring the current in mA flowing through the device under test using a Keithley 2635 source-measure unit. The voltage applied to the device is varied in steps of 0.1 V from 0 V to 10 V. Similarly, the luminance-voltage characteristic and CIE coordinates are measured in cd / m for each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminance is determined by measuring the luminance in units of 10 ...

[0723] For bottom emission devices, the light emission is predominantly Lambertian and is quantified by the external quantum efficiency (EQE) in %. To determine the efficiency EQE in %, the light output of the device is measured using a calibrated photodiode at 10 mA / cm 2 It is measured in.

[0724] In top-emitting devices, the light emission is forward-directed, non-Lambertian, and highly dependent on the Mirco cavity. Therefore, the efficiency EQE is higher compared to bottom-emitting devices. To determine the efficiency EQE in %, a calibrated photodiode was used, with a current of 10 mA / cm 2 Measure the light output of the device.

[0725] The device lifetime, LT, was measured using a Keithley 2400 source meter at ambient conditions (20°C) and 30 mA / cm 2 and recorded in hours.

[0726] The luminance of the device is measured using a calibrated photodiode. The lifetime, LT, is defined as the time until the luminance of the device drops to 97% of its initial value.

[0727] The increase in operating voltage, ΔU, is used as a measure of the operating voltage stability of the device. This increase is determined during the LT measurement by subtracting the operating voltage after 1 hour from the operating voltage after 100 hours.

[0728] ΔU = [U100h) - U(1h)].

[0729] Or the operating voltage after 400 hours, down from the operating voltage one hour after the device is put into operation.

[0730] ΔU = [U400h) - U(1h)].

[0731] The smaller the value of ΔU, the more stable the operating voltage becomes.

[0732] [Luminous flux] Samples were individually placed in an integrating sphere and measured at 10 mA / cm using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminous flux was measured at a current density of 1000 Hz. A Keithley 2635 source measurement unit was used as a constant current source.

[0733] [Technical effect of the invention]

[0734] [Table 1] JPEG2025500369000246.jpg94169JPEG2025500369000247.jpg94169JPEG2025500369000248.jpg94169JPEG2025500369000249.j pg105169JPEG2025500369000250.jpg94169JPEG2025500369000251.jpg94169JPEG2025500369000252.jpg98169JPEG2025500369 000253.jpg94169JPEG2025500369000254.jpg94169JPEG2025500369000255.jpg94169JPEG2025500369000256.jpg94169JPEG202 5500369000257.jpg99169JPEG2025500369000258.jpg94169JPEG2025500369000259.jpg94169JPEG2025500369000260.jpg93169

[0735] The compounds, particularly the compounds of the present invention, exhibit low absorption in the range of 300 to 650 nm.

[0736] Thus, the compounds may be useful in providing organic electronic or display devices with improved display brightness and, if low current densities are used, may extend the lifetime of the display.

[0737] [Table 2]

[0738] From Table 2 it can be seen that layers containing radialenes with λabs(max) less than 459 nm and organic hole transport compounds have lower absorption of visible light, especially in the green and blue portions of visible light.

[0739] This can be beneficial to increase the brightness of the display or to extend the life of the display when using lower current densities.

[0740] [Table 3]

[0741] According to Table 3, higher luminous flux could be measured for the charge generating layer according to the present invention.

[0742] This can be beneficial to increase the brightness of the display or to extend the life of the display when using lower current densities.

[0743] [Table 4] JPEG2025500369000264.jpg128169JPEG2025500369000265.jpg76169

[0744] [Table 5] JPEG2025500369000267.jpg35169

[0745] The particular combinations of elements and features in the above detailed embodiments are merely illustrative, and interchangeability and substitution of these teachings with other teachings in the specification and patents / applications incorporated by reference are also expressly contemplated. As one skilled in the art will recognize, variations, modifications, and other implementations of what is described herein may occur to one skilled in the art without departing from the spirit and scope of the invention as claimed. Thus, the foregoing description is illustrative only and is not intended to be limiting. In the claims, the word "comprises" does not exclude other elements or steps, and the indefinite articles "a" or "an" do not exclude a plurality. The mere fact that certain measures are recited in mutually different dependent claims does not indicate that a combination of these measures cannot be used to advantage. The scope of the invention is defined in the following claims and their equivalents. Moreover, the reference signs used in the specification and claims do not limit the scope of the invention as recited in the claims. [Brief description of the drawings]

[0746] [Figure 1] FIG. 1 is a schematic cross-sectional view of an OLED including a charge generating layer in accordance with an illustrative embodiment of the invention. [Diagram 2] FIG. 2 is a schematic cross-sectional view of a stacked OLED including a charge generating layer according to an exemplary embodiment of the invention.

Claims

1. A charge generating layer comprising a first charge generating layer and a second charge generating layer, the first charge generating layer comprising a compound of formula (I): 【Chemistry 1】 In the formula (I), A １ is independently selected from the group of formula (II): 【Chemistry 2】 Here, Ar １ is a substituted or unsubstituted C ６ ~C ３６ Aryl, and substituted or unsubstituted C ２ ~C ３６ heteroaryl; Ar １ When is substituted, one or more of the substituents may be selected from the group consisting of electron withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO. ２ are independently selected from the group consisting of: A ２ and A ３ is independently selected from the group of formula (III): 【Chemistry 3】 Here, Ar ２ is a substituted or unsubstituted C ６ ~C ３６ Aryl, and substituted or unsubstituted C ２ ~C ３６ heteroaryl; Ar ２ When is substituted, one or more of the substituents may be selected from the group consisting of electron withdrawing groups, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and -NO. ２ are independently selected from the group consisting of: Each R' is a substituted or unsubstituted C ６ ~C １８ Aryl, C ３ ~C １８ Heteroaryl, electron withdrawing group, partially fluorinated C １ ~C ８ Alkyl, perfluorinated C １ ~C ８ independently selected from alkyl, halogen, F or CN; Here, the compound of formula (I) is dissolved in DCM at 20° C. for 10 －５ ~10 －４ When measured at a concentration of mol / L, the absorption maximum λ is ≦459 nm. ｍａｘ using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) in the gas phase using the hybrid functional PBE0 with the def2-SVP basis set and ＊ When calculated by TDDFT including the first 30 singlet transitions from the optimized geometry using the hybrid functional B3LYP with basis set, the absorption maximum λ is ≦494 nm. ｍａｘ having and / or using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to use the hybrid functional PBE0 with the def2-SVP basis set in the gas phase and ＊ When calculated by TDDFT including the first 30 singlet transitions from an optimized geometry using the hybrid functional B3LYP with basis set, the UV-Vis spectrum has an integral of ≦50 a.u.×nm in the range of 400-650 nm; wherein the first charge generating layer comprises an organic hole transporting compound and the second charge generating layer comprises an organic electron transporting compound and a metal dopant.

2. The charge generating layer of claim 1, wherein the charge generating layer is not a charge generating layer selected from the group consisting of y) to vv): y) The first charge generating layer is １ , A ２ and A ３ 10.1% by volume of a compound of formula (I) selected according to: 【Chemistry 4】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; z) The first charge generating layer is １ , A ２ and A ３ 9.8% by volume of a compound of formula (I) selected according to: 【Chemistry 5】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; aa) The first charge generating layer is １ , A ２ and A ３ 12% by volume of a compound of formula (I) selected according to: 【Chemistry 6】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; bb) the first charge generating layer is １ , A ２ and A ３ 9.6% by volume of a compound of formula (I) selected according to: 【Chemistry 7】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; cc) the first charge generating layer is １ , A ２ and A ３ 10.1% by volume of a compound of formula (I) selected according to: 【Chemistry 8】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 81 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; dd) the first charge generating layer is １ , A ２ and A ３ 9.9% by volume of a compound of formula (I) selected according to: 【Chemistry 9】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; ee) the first charge generating layer is １ , A ２ and A ３ 10.8% by volume of a compound of formula (I) selected according to: 【Chemistry 10】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; ff) the first charge generating layer is １ , A ２ and A ３ 11.8% by volume of a compound of formula (I) selected according to: 【Chemistry 11】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 86 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; gg) the first charge generating layer is １ , A ２ and A ３ 9.9% by volume of a compound of formula (I) selected according to: 【Chemistry 12】 and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; hh) the first charge generating layer is １ , A ２ and A ３ 10.3% by volume of a compound of formula (I) selected according to: 【Chemistry 13】 and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; ii) The first charge generating layer is １ , A ２ and A ３ 10.3% by volume of a compound of formula (I) selected according to: 【Chemistry 14】 and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; jj) the first charge generating layer is １ , A ２ and A ３ % by volume of a compound of formula (I) selected according to: 【Chemistry 15】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; kk) the first charge generating layer is １ , A ２ and A ３ % by volume of a compound of formula (I) selected according to: 【Chemistry 16】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; ll) The first charge generating layer is １ , A ２ and A ３ % or 10% by volume of a compound of formula (I) selected according to: 【Chemistry 17】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; mm) the first charge generating layer is A １ , A ２ and A ３ % or 10% by volume of a compound of formula (I) selected according to: 【Chemistry 18】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; nn) the first charge generating layer is １ , A ２ and A ３ 10% by volume of a compound of formula (I) selected according to: 【Chemistry 19】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; oo) the first charge generating layer is １ , A ２ and A ３ 10% by volume of a compound of formula (I) selected according to: 【Chemistry 20】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; pp) the first charge generating layer is １ , A ２ and A ３ 10% by volume of a compound of formula (I) selected according to: 【Chemistry 21】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-4-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 vol. % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol. % or 3 vol. % Li, the second charge generating layer having a thickness of 10 nm; qq) The first charge generating layer is １ , A ２ and A ３ 10% by weight of a compound of formula (I) selected according to: 【Chemical 22】 the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; rr) the first charge generating layer is １ , A ２ and A ３ 10% by weight of a compound of formula (I) selected according to: 【Chemistry 23】 the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; ss) the first charge generating layer is １ , A ２ and A ３ 10% by weight of a compound of formula (I) selected according to: 【Chemistry 24】 the first charge generating layer has a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 10 nm; tt) the first charge generating layer is １ , A ２ and A ３ 10% by volume or weight of a compound of formula (I) selected according to: 【Chemistry 25】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer, the second charge generating layer comprising 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 15 nm; uu) The first charge generating layer is １ , A ２ and A ３ 10% by volume or weight of a compound of formula (I) selected according to: 【Chemistry 26】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; a charge generating layer comprising 99% by volume of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1% by volume of Li, the second charge generating layer having a thickness of 15 nm; and vv) the first charge generating layer is １ , A ２ and A ３ 10% by volume or weight of a compound of formula (I) selected according to: 【Chemical 27】 and N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, the first charge generating layer having a thickness of 10 nm; The second charge generating layer comprises 99 volume % 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume % Li, the second charge generating layer having a thickness of 15 nm.

3. 3. The charge generating layer of claim 1 or 2, wherein the organic electron transport compound contains 15 covalently bonded atoms.

4. 4. The charge generating layer according to claim 1, wherein the metal dopant is Yb or a metal alloy containing a metal selected from the group consisting of Li and Yb.

5. The organic electron transport compound is B3LYP / 6-31G ＊ The charge generating layer of any one of claims 1 to 4 having a LUMO of <-1.75 eV as calculated by DFT using

6. The compound of formula (I) was dissolved in DCM at 20° C. for 10 －５ ~10 －４ When measured at a concentration of mol / L, the absorption maximum λ is ≦455 nm. ｍａｘ The charge generating layer of any one of claims 1 to 5, having a wavelength of preferably ≦450 nm, more preferably ≦445 nm, more preferably ≦441 nm, and most preferably ≦440 nm.

7. The compounds of formula (I) have an absorption maximum λ ≦475 nm, preferably ≦455 nm. ｍａｘ The charge generating layer according to any one of claims 1 to 5, comprising:

8. The compound of formula (I) was prepared by precipitation in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). ＊ 8. The charge generating layer of claim 1, wherein the LUMO, expressed on an absolute scale with reference to the vacuum energy level of zero, when calculated by applying the hybrid functional B3LYP having a basis set, is in the range of ≧−5.7 eV to ≦−4.7 eV, preferably ≧−5.6 eV to ≦−4.7 eV, more preferably ≧−5.55 eV to ≦−4.75 eV, more preferably ≧−5.50 eV to ≦−4.80 eV, and most preferably ≧−5.45 eV to ≦−4.85 eV.

9. An organic electronic device comprising a charge generating layer according to any one of claims 1 to 8.

10. 9. An organic electronic device comprising at least two vertically stacked electroluminescent units and a charge generating layer according to any one of claims 1 to 8, wherein each electroluminescent unit comprises at least one light-emitting layer.

11. 11. An organic electronic device according to claim 9 or 10, comprising at least three or at least four vertically stacked electroluminescent units, each electroluminescent unit comprising at least one light-emitting layer.

12. A display device comprising a plurality of organic electronic devices according to any one of claims 9 to 11.

13. The display device of claim 12, wherein at least two of the plurality of organic electronic devices share a common charge generating layer as a charge generating layer, the common charge generating layer being a charge generating layer according to any one of claims 1 to 7.

14. A compound according to formula (XI), 【Chemistry 28】 In the formula (XI), A １ is selected from the group of formula (XIIa) 【Chemical 29】 Where: X １ is CR １ or N; X ２ is CR ２ or N; X ３ is CR ３ or N; X ４ is CR ４ Selected from: X ５ is CR ５ or N; R １ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ２ , R ３ and R ５ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, R １ , R ２ , R ３ and R ５ If any of X is present, then the corresponding １ , X ２ , X ３ , and X ５ is not N; In the formula (XI), A ２ and A ３ are independently selected from formula (XIII): 【Chemistry 30】 Ar is a substituted or unsubstituted C ６ ~C １８ Aryl, and substituted or unsubstituted C ２ ~C １８ heteroaryl, wherein the substituents on Ar are independently selected from electron withdrawing groups, CN, partially or perfluorinated C １ ~C ６ Alkyl, halogen, -NO ２ , Cl, F, D; and R′ is a substituted or unsubstituted C ６ ~C １８ Aryl or C ３ ~C １８ Heteroaryl, partially fluorinated or perfluorinated C １ ~C ８ A compound selected from alkyl, halogen, F or CN.

15. The compound of formula (XI) is selected from the compounds of formula (XI) 【Chemistry 31】 In the formula (XI), A １ is selected from the group of formula (XIIa) 【Chemistry 32】 Where: X １ is CR １ or N; X ２ is CR ２ or N; X ３ is CR ３ or N; X ４ is CR ４ Selected from: X ５ is CR ５ or N; R １ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ２ , R ３ and R ５ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, R １ , R ２ , R ３ and R ５ If any of X is present, then the corresponding １ , X ２ , X ３ , and X ５ is not N; In formula (XI), A ２ and A ３ are independently selected from formula (XIII): 【Chemical 33】 Ar is a substituted or unsubstituted C ６ ~C １８ Aryl, and substituted or unsubstituted C ２ ~C １８ heteroaryl, wherein the substituents on Ar are independently selected from electron withdrawing groups, CN, partially or perfluorinated C １ ~C ６ Alkyl, halogen, -NO ２ , Cl, F, D; and R′ is a substituted or unsubstituted C ６ ~C １８ Aryl or C ３ ~C １８ Heteroaryl, partially fluorinated or perfluorinated C １ ~C ８ selected from alkyl, halogen, F or CN; wherein said compound of formula (XI) comprises at least 5 CN groups; In the formula (XIIa), X ｎ is N and X ｎ＋１ is CR ｎ＋１ If R ｎ＋１ cannot be CN (n=1-4); In the formula (XIIa), X ｎ is N and X ｎ－１ is CR ｎ－１ If R ｎ－１ The compound of claim 14, wherein n cannot be CN (n=1-4).

16. The compound of formula (XI) is selected from the compounds of formula (XI) 【Chemical 34】 Here, A １ is selected from formula (XIIb): 【Chemistry 35】 Where: X １ is CR １ or N; X ２ is CR ２ or N; X ３ is CR ３ or N; X ４ is CR ４ Selected from: R １ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ２ and R ３ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, R １ , R ２ and R ３ If any of X is present, then the corresponding １ , X ２ , and X ３ is not N; However, R １ and R ４ exists and R １ Or R ４ If only CN is selected, then R ２ , R ３ and the remaining R １ Or R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, D, or R ２ and R ３ is CN, partially fluorinated or perfluorinated C ２ ~C ８ alkyl, halogen, Cl, F, D or H, or R ２ , R ３ and the remaining R １ Or R ４ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D; Or, where R １ and R ４ exists and R １ Or R ４ Only perfluorinated C １ When selected from ２ and R ３ is partially fluorinated or perfluorinated C ２ ~C ８ independently selected from alkyl, halogen, Cl, F, D, or H; or R ２ , R ３ and the remaining R １ Or R ４ is CN, partially fluorinated or perfluorinated C １ ~C ８ selected from alkyl, halogen, Cl, F, D; Or, where X １ is N and R ４ When is selected from CN, R ２ , R ３ is selected from H or D (if present), or R ２ and R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D, provided that R ２ and R ３ Both of them cannot be CNs, or R ２ is partially fluorinated or perfluorinated C ２ ~C ８ selected from alkyl, halogen, Cl, F, D or H; Or, where X １ is N and R ４ Perfluorinated C １ When selected from alkyl, R ２ is partially fluorinated or perfluorinated C ２ ~C ８ alkyl, halogen, Cl, F, D, or R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ alkyl, halogen, Cl, F, D, or R ２ and R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D, or R ２ and R ３ is (if present) independently selected from H or D; In the formula (XI), A ２ and A ３ are independently selected from formula (XIII): 【Chemical 36】 Ar is a substituted or unsubstituted C ６ ~C １８ Aryl, and substituted or unsubstituted C ２ ~C １８ heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C １ ~C ６ independently selected from alkyl, halogen, Cl, F, D; and R′ is a substituted or unsubstituted C ６ ~C １８ Aryl or C ３ ~C １８ Heteroaryl, partially fluorinated or perfluorinated C １ ~C ８ 16. The compound according to claim 14 or 15, selected from alkyl, halogen, F or CN.

17. The compound of formula (XI) is selected from the compounds of formula (XI) 【Chemical 37】 A １ is selected from formula (XIIb): 【Chemical 38】 Where: X １ is CR １ or N; X ２ is CR ２ or N; X ３ is CR ３ or N; X ４ is CR ４ Selected from: R １ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ２ , and R ３ (if present) partially or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; X ３ If N, then X ４ CR ４ R ４ cannot be CN; X ２ is N and X １ is CR １ If R １ cannot be a CN; R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, R １ , R ２ and R ３ If any of X is present, then the corresponding １ , X ２ , and X ３ is not N; However, R １ and R ４ exists and R １ Or R ４ If only CN is selected, then R ２ , R ３ and the remaining R １ Or R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, D, or R ２ and R ３ is CN, partially fluorinated or perfluorinated C ２ ~C ８ alkyl, halogen, Cl, F, D or H, or R ２ , R ３ and the remaining R １ Or R ４ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D; Or, where R １ and R ４ exists and R １ Or R ４ Only perfluorinated C １ When selected from ２ and R ３ is partially fluorinated or perfluorinated C ２ ~C ８ independently selected from alkyl, halogen, Cl, F, D, or H; or R ２ , R ３ and the remaining R １ Or R ４ is CN, partially fluorinated or perfluorinated C １ ~C ８ selected from alkyl, halogen, Cl, F, D; Or, where X １ is N and R ４ When is selected from CN, R ２ , R ３ is selected from H or D (if present), or R ２ and R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D, provided that R ２ and R ３ Both of them cannot be CNs, or R ２ is partially fluorinated or perfluorinated C ２ ~C ８ selected from alkyl, halogen, Cl, F, D or H; Or, where X １ is N and R ４ Perfluorinated C １ When selected from alkyl, R ２ is partially fluorinated or perfluorinated C ２ ~C ８ alkyl, halogen, Cl, F, D, or R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ alkyl, halogen, Cl, F, D, or R ２ and R ３ is CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D, or R ２ and R ３ is (if present) independently selected from H or D; In the formula (XI), A ２ and A ３ are independently selected from formula (XIII): 【Chemical Formula 39】 Ar is a substituted or unsubstituted C ６ ~C １８ Aryl, and substituted or unsubstituted C ２ ~C １８ heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C １ ~C ６ independently selected from alkyl, halogen, Cl, F, D; and R′ is a substituted or unsubstituted C ６ ~C １８ Aryl or C ３ ~C １８ Heteroaryl, partially fluorinated or perfluorinated C １ ~C ８ selected from alkyl, halogen, F or CN; The compound according to any one of claims 14 to 16, wherein the compound of formula (XI) comprises at least 5 CN groups.

18. A in the compound according to formula (XI) １ The compound according to any one of claims 14 to 17, wherein is selected from one of the following formulae: 【Chemistry 40】

19. A in the compound according to formula (XI) １ The compound according to any one of claims 14 to 18, wherein is selected from one of the following formulae: 【Chemistry 41】

20. A in the compound according to formula (XI) １ is selected from one of the following formulas: 【Chemistry 42】 The compound according to any one of claims 14 to 19, wherein the compound of formula (XI) comprises at least 5 CN groups.

21. A in the compound according to formula (XI) ２ and A ３ is independently selected from one of the following formulas: 【Chemistry 43】 【change】

22. A in the compound according to formula (XI) ２ and A ３ is independently selected from one of the following formulas: 【Chemistry 44】 【change】

23. A in the compound according to formula (XI) ２ and A ３ is independently selected from one of the following formulas: 【Chemistry 45】 【change】 23. The compound of claim 15 or 22, wherein the compound of formula (XI) comprises at least five CN groups.

24. The compound of formula (XI) is selected from the compounds of formula (XIV) 【Chemistry 46】 Where: X １ is CR １ or N; X ２ is CR ２ or N; X ３ is CR ３ or N; X ４ is CR ４ Selected from: R １ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ２ and R ３ (when present) is an electron withdrawing group, CN, partially fluorinated or perfluorinated C １ ~C ８ Alkyl, -NO ２ , halogen, Cl, F, D or H; R ４ CN, and partially or perfluorinated C １ ~C ８ alkyl, R １ , R ２ and R ３ If any of X is present, then the corresponding １ , X ２ and X ３ is not N; R′ is a substituted or unsubstituted C ６ ~C １８ Aryl or C ３ ~C １８ Heteroaryl, partially fluorinated or perfluorinated C １ ~C ８ selected from alkyl, halogen, F or CN; Where: Each X １ ' is CR １ ' or N; Each X ２ ' is CR ２ ' or N; Each X ３ ' is CR ３ ' or N; Each X ４ ' is CR ４ ' or N; Each X ５ ' is CR ５ ' or N; Each R １ ', R ２ ', R ３ ', R ４ ' and R ５ ' (if present) is an electron withdrawing group, F, CN, partially fluorinated or perfluorinated C １ ~C ８ independently selected from alkyl, halogen, Cl, F, D or H, whereby R １ ', R ２ ', R ３ ', R ４ ' and R ５ If any of X' is present, then the corresponding １ ', X ２ ', X ３ ', X ４ ' and X ５ The compound according to any one of claims 14 to 17, wherein ' is not N.

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