Organic electronic element comprising compound for organic electronic element and electronic device thereof

Abstract

There is provided an organic electronic element including a first electrode, a second electrode, and a light emitting layer formed between the first electrode and the second electrode; and an electronic device including the organic electronic element, in which the organic material layer contains the compounds represented by Formula 1 and Formula 2 according to the present invention, thereby reducing the driving voltage of the organic electronic element and improving luminous efficiency and lifespan.

Description

Technical Field

[0001] The present invention relates to an organic electronic element and an electronic device thereof using a compound for an organic electronic element. Background Art

[0002] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic electronic element using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is generally composed of a multilayer structure composed of different materials and may include, for example, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and the like.

[0003] Materials used as an organic material layer in an organic electronic element can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like.

[0004] The most problematic issues of organic electroluminescent devices are service life and efficiency, and as the display area becomes larger, these efficiency and service life issues must be resolved. Efficiency, service life and driving voltage are related to each other, and when efficiency increases, driving voltage is relatively reduced, and as driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, and thus service life tends to increase.

[0005] However, efficiency cannot be maximized simply by improving the organic material layer. This is because long service life and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined.

[0006] Furthermore, recently, in organic electroluminescent devices, in order to solve the emission problem in the hole transport layer, an emission auxiliary layer must exist between the hole transport layer and the emission layer, and different emission auxiliary layers need to be developed according to each emission layer (R, G, B).

[0007] Generally, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, thereby generating excitons through recombination.

[0008] However, the material for the hole transport layer has a low HOMO value and thus mainly has a low T1 value, so excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge imbalance in the emission layer and light emission at the interface of the hole transport layer.

[0009] When light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic element are reduced, and the service life is shortened. Therefore, it is urgent to develop an emission auxiliary layer with a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the emission layer.

[0010] At the same time, it is necessary to develop hole injection layer materials that have stable characteristics, i.e., high glass transition temperature, to resist the Joule heat generated when the device is driven, while delaying the penetration of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the reasons for shortening the service life of organic electronic components. The low glass transition temperature of the hole transport layer material has the following characteristics: when the device is driven, the uniformity of the film surface is reduced, which is reported to have a great influence on the service life of the device. In addition, OLED devices are mainly formed by a deposition method, and it is necessary to develop materials that can withstand long-term deposition, i.e., materials with high heat resistance characteristics.

[0011] That is, in order to fully demonstrate the excellent characteristics of organic electronic components, the materials used to form the organic material layer in the component (such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, emission auxiliary layer materials) should be supported by stable and effective materials. However, such stable and effective organic material layer materials for organic electronic components have not been fully developed. Therefore, it is necessary to continuously develop new materials.

[0012] Therefore, there is a continuous demand for the development of new materials, and in particular, there is an urgent demand for the development of materials for a light-emitting auxiliary layer.

[0013] [Prior art literature]

[0014] [Patent document]

[0015] (Patent Document 1) Korean Document 10-2023-0014596A

[0016] (Patent Document 2) Korean Document 10-2023-0113120A

[0017] (Patent Document 3) Korean Document 10-2023-0112776A

[0018] (Patent Document 4) Korean Document 10-2428232B

[0019] (Patent Document 5) Korean Document 10-2428237B Summary of the invention

[0020] An object of the present invention is to provide an organic electronic element and an electronic device thereof comprising a compound that can reduce the driving voltage of the element and improve the luminous efficiency, color purity, stability and service life of the element.

[0021] [Technical solution]

[0022] In one aspect, the present invention provides an organic electronic element, which includes a first electrode; a second electrode; and an organic material layer including a light-emitting layer formed between the first electrode and the second electrode, wherein the organic material layer includes a hole transport layer formed between the first electrode and the light-emitting layer, and includes a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, wherein the plurality of light-emitting auxiliary layers include a first light-emitting auxiliary layer and a second light-emitting auxiliary layer, wherein the first light-emitting auxiliary layer is adjacent to the hole transport layer, wherein the second light-emitting auxiliary layer is adjacent to the light-emitting layer, wherein the first light-emitting auxiliary layer contains a compound represented by formula (1), and the second light-emitting auxiliary layer contains a compound represented by formula (2).

[0023] <Formula 1>

[0024]

[0025] <Formula 2>

[0026]

[0027] [Effects of the invention]

[0028] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and service life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figures 1 to 3 Examples of the organic electronic element according to the present invention are illustrated. DETAILED DESCRIPTION

[0030] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when a detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0031] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. It should be noted that if a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected", "coupled" or "connected" between the components.

[0032] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0033] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0034] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0035] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0036] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0037] Unless otherwise specified, the term “alkoxy,” “alkoxy group,” or “alkyloxy group” as used herein means an oxy group attached to an alkyl group and has 1 to 60 carbon atoms, but is not limited thereto.

[0038] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means an oxy group connected to an aryl group and has 6 to 60 carbon atoms, but is not limited thereto.

[0039] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. Herein, aryl groups or arylene groups mean monocyclic and polycyclic aromatic groups, and may also be formed by combining with adjacent groups. Examples of "aryl groups" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0040] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0041] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0042] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms (but not limited thereto), has 2 to 60 carbon atoms, includes any one of a monocyclic and polycyclic ring, and may include a heteroaliphatic ring and / or a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0043] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0044] Furthermore, the term "heterocyclic group" may include a ring containing SO2 in place of carbon constituting the ring.

[0045] For example, the "heterocyclic group" includes the following compounds.

[0046]

[0047] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0048]

[0049] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to the number of atoms in the compound.

[0050] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0051] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0052] In addition to the above-mentioned hetero compounds, other hetero compounds or hetero groups contain one or more hetero atoms, but are not limited thereto.

[0053] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substitution is substituted by at least one substituent selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterated C6-C 20 Aryl group, C8-C 20 Arylene groups, silane groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not limited thereto.

[0054] Unless expressly stated otherwise, the formulae for the present invention as used herein apply in the same manner as the definition of substituents according to the definition of the exponents of the formulae below.

[0055]

[0056] When a is an integer of 0, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 When a is an integer of 2 or 3, each substituent R 1 may be the same or different, and when a is an integer of 4 to 6, is connected to the benzene ring in a similar manner, but indication of hydrogen bonded to carbon forming the benzene ring is omitted.

[0057]

[0058] In the following, reference will be made to Figures 1 to 3Layer structures of organic electronic components comprising the compounds according to the invention are described.

[0059] When adding reference numerals to components in each drawing, it should be noted that even if the same components are shown in different drawings, the same components should be given the same reference numerals as much as possible. In addition, when describing the present invention, if it is determined that the detailed description of related known configurations or functions may confuse the main points of the present invention, the detailed description will be omitted.

[0060] Figures 1 to 3 is an exemplary diagram of an organic electronic element according to an embodiment of the present invention.

[0061] refer to Figure 1 The organic electrical element (100) according to the present invention includes a first electrode (110) formed on a substrate (not shown), a second electrode (170), and an organic material layer formed between the first electrode (110) and the second electrode (170).

[0062] Among them, the first electrode (110) may be an anode (positive electrode), and the second electrode (170) may be a cathode (negative electrode), and in the case of an inverted organic electrical element, the first electrode may be a cathode, and the second electrode may be an anode.

[0063] The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160). Specifically, the organic material layer may include a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) sequentially formed on the first electrode (110).

[0064] Preferably, the light efficiency enhancement layer (180) can be formed on one of the two surfaces of the first electrode (110) or the second electrode (120), which surface does not contact the organic material layer. When the light efficiency enhancement layer (180) is formed, the light efficiency of the organic electronic element can be improved.

[0065] For example, a light efficiency enhancement layer (180) can be formed on the second electrode (170), and in the case of a top-emitting organic light-emitting device, the light efficiency enhancement layer (180) is formed to reduce light energy loss due to surface plasmon polaritons (SPP) in the second electrode (170), and in the case of a bottom-emitting organic light-emitting device, the light efficiency enhancement layer (180) can be used as a buffer for the second electrode (170).

[0066] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will be referred to in detail. Figure 2 Give a description.

[0067] refer to Figure 2 According to another embodiment of the present invention, an organic electronic device (200) includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) formed in sequence on a first electrode (110), and a light efficiency enhancement layer (180) is formed on the second electrode.

[0068] although Figure 2 Although not shown, an electron transport auxiliary layer may be further formed between the light emitting layer (140) and the electron transport layer (150).

[0069] In addition, according to another embodiment of the present invention, the organic material layer may have a plurality of stacks including a hole transport layer, a light emitting layer and an electron transport layer. Figure 3 Give a description.

[0070] refer to Figure 3 In an organic electronic element (300) according to another embodiment of the present invention, 2 or more stacks (ST1 and ST2) made of a plurality of organic material layers may be formed between a first electrode (110) and a second electrode (170), and a charge generating layer (CGL) may be formed between the stacks of the organic material layers.

[0071] Specifically, the organic electronic element according to the embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL), a second stack (ST2), a second electrode (170), and a light efficiency enhancement layer (180).

[0072] The first stack (ST1) is an organic material layer formed on the first electrode (110), and may include a first hole injection layer (320), a first hole transport layer (330), a first light emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light emitting layer (440), and a second electron transport layer (450). Like this, the first stack and the second stack may be organic material layers having the same laminated structure, but may also be organic material layers having different laminated structures.

[0073] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). The charge generation layer (CGL) is formed between the first light emitting layer (340) and the second light emitting layer (440) to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.

[0074] When through Figure 3 When a plurality of light-emitting layers are formed by the multilayer stack structure method shown in FIG. 1 , an organic electronic element that emits white light by a mixing effect of light emitted from each light-emitting layer and an organic electronic element that emits light of various colors can be manufactured.

[0075] The compounds represented by Formula 1 and Formula 2 of the present invention can be used as materials for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a luminescence auxiliary layer (220), an electron transport layer (150, 350, 450), an electron injection layer (160), a luminescent layer (140, 340, 440) or a light efficiency enhancement layer (180), but preferably, the compounds represented by Formula 1 or Formula 2 of the present invention can be used as a luminescence auxiliary layer (220).

[0076] Even if the same or similar core is used, the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is bonded at what position. Therefore, it is necessary to study the selection of the core and the combination of the sub-substituents bonded thereto, especially when achieving the optimal combination of the energy levels and T1 values ​​of each organic material layer and the unique properties of the material (mobility, interface properties, etc.), so that long service life and high efficiency can be achieved at the same time.

[0077] The organic light-emitting device according to the embodiment of the present invention can be manufactured using various deposition methods. It can be manufactured using a vapor deposition method such as PVD or CVD. For example, an anode (110) is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150) and an electron injection layer (160) is formed thereon. After that, an organic electroluminescent device according to the embodiment of the present invention can be manufactured by depositing a material that can be used as a cathode (170) thereon. In addition, a light-emitting auxiliary layer (220) can also be formed between the hole transport layer (130) and the light-emitting layer (140), and an electron transport auxiliary layer (not shown) can also be formed between the light-emitting layer (140) and the electron transport layer (150), and as described above, can be formed in a stacked structure.

[0078] In addition, the organic material layer can be manufactured with a smaller number of layers by using various polymer materials and not by a deposition method, but by a solution process or a solvent process, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process or a roll-to-roll process, a doctor blade process, a screen printing process or a thermal transfer method, etc. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0079] Furthermore, the organic electronic element according to an embodiment of the present invention may be selected from an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

[0080] Another embodiment of the present invention may include an electronic device, which includes a display device including the organic electronic element of the present invention; and a control unit for driving the display device. At this time, the electronic device may be a current or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various kinds of televisions, and various kinds of computers.

[0081] Hereinafter, an organic electronic element according to aspects of the present invention will be described.

[0082] An organic electronic element according to an embodiment of the present invention includes a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer includes a hole transport layer formed between the first electrode and the light-emitting layer, and includes a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, wherein the plurality of light-emitting auxiliary layers include a first light-emitting auxiliary layer and a second light-emitting auxiliary layer, wherein the first light-emitting auxiliary layer is adjacent to the hole transport layer, wherein the second light-emitting auxiliary layer is adjacent to the light-emitting layer, wherein the first light-emitting auxiliary layer includes a compound represented by Formula 1, and the second light-emitting auxiliary layer includes a compound represented by Formula 2:

[0083] <Formula 1>

[0084]

[0085] <Formula 2>

[0086]

[0087] In equations (1) and (2), each symbol can be defined as follows.

[0088] R a , R b , R 1 and R2 are independently the same or different and are independently selected from hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; or multiple adjacent R a and multiple R b can be bonded to each other to form a ring,

[0089] When R a , R b , R 1 and R 2 When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 20 Aryl group, C6-C 18 Aryl group, C6-C 16 Aryl group, C6-C 14 Aryl group, C6-C 12 Aryl group, C6-C 10 Aryl group, C6 aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0090] When R a , R b , R 1 and R 2 When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic group, C2-C 20 Heterocyclic group, C2-C 18 Heterocyclic group, C2-C 16 Heterocyclic group, C2-C 12 Heterocyclic group, C 12 Heterocyclic groups such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, dibenzoquinazoline, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, and the like,

[0091] When R a , R b , R 1 and R 2 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0092] When R a , R b , R 1 and R 2 When it is an alkyl group, it is preferably C1-C 30 Alkyl groups, more preferably C1-C 24 Alkyl groups, C1-C 10 Alkyl group, C1-C4 alkyl group, such as methyl, ethyl, isopropyl, tert-butyl, etc.

[0093] When R a , R b , R 1 and R 2 When it is an alkoxy group, it is preferably C1-C 24 Alkoxy groups, more preferably C1-C 10 Alkoxy group, C1-C4 alkoxy group, such as methoxy, ethoxy, isopropoxy, tert-butoxy and the like.

[0094] When R a , R b , R 1 and R 2 When it is an aryloxy group, it is preferably C6-C 24 Aryloxy groups, more preferably C6-C 18 Aryloxy groups, C6-C 16 Aryloxy groups, C6-C 14 Aryloxy groups, C6-C 12 Aryloxy groups, C6-C 10 Aryloxy group, C6 aryloxy group,

[0095] R c and R d Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 an aryloxy group; or R c and R d may be bonded to each other to form a spiro ring,

[0096] When R c and R d When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 20 Aryl group, C6-C 18 Aryl group, C6-C 16 Aryl group, C6-C 14 Aryl group, C6-C 12 Aryl group, C6-C 10 Aryl groups, C6 aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0097] When R c and R d When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic group, C2-C 20 Heterocyclic group, C2-C 18 Heterocyclic group, C2-C 16 Heterocyclic group, C2-C 12 Heterocyclic group, C 12 Heterocyclic groups such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, dibenzoquinazoline, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, and the like,

[0098] When R c and R d When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0099] When R c and R d When it is an alkyl group, it is preferably C1-C30 Alkyl groups, more preferably C1-C 24 Alkyl groups, C1-C 10 Alkyl group, C1-C4 alkyl group, for example methyl, ethyl, isopropyl, tert-butyl.

[0100] When R c and R d When it is an alkoxy group, it is preferably C1-C 24 Alkoxy groups.

[0101] When R c and R d When it is an aryloxy group, it is preferably C6-C 24 Aryloxy group.

[0102] L a , L b , L c , L 1 and L 2 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups;

[0103] When L a , L b , L c , L 1 and L 2 When it is an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C 25 Arylene group, C6-C 20 Arylene group, C6-C 18 Arylene group, C6-C 16 Arylene group, C6-C 14 Arylene group, C6-C 12 Arylene group, C6-C 10 Arylene group, C6 arylene group, such as phenylene, biphenylene, naphthylene, triphenylene, anthracene and the like.

[0104] When L a , L b , L c , L 1 and L 2 When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24Heterocyclic group, C2-C 20 Heterocyclic group, C2-C 18 Heterocyclic group, C2-C 16 Heterocyclic group, C2-C 12 Heterocyclic group, C 12 Heterocyclic groups such as pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene and the like.

[0105] When L a , L b , L c , L 1 and L 2 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0106] Ar a ,Ar b ,Ar 1 and Ar 2 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Cycloalkyl group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 Aryloxy groups;

[0107] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 20 Aryl group, C6-C 18 Aryl group, C6-C 16 Aryl group, C6-C 14 Aryl group, C6-C 12Aryl group, C6-C 10 Aryl group, C6 aryl group, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene and the like.

[0108] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is a heterocyclic group, it may preferably be C2-C 30 A heterocyclic group, and more preferably a C2-C 24 Heterocyclic group, C2-C 20 Heterocyclic group, C2-C 18 Heterocyclic group, C2-C 16 Heterocyclic group, C2-C 12 Heterocyclic group, C 12 Heterocyclic groups such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, dibenzoquinazoline, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, and the like.

[0109] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is a cycloalkyl group, it is preferably C3-C 30 Cycloalkyl group; more preferably C3-C 24 Cycloalkyl groups, C3-C 18 Cycloalkyl groups, C3-C 14 Cycloalkyl groups, C3-C 10 Cycloalkyl groups, C6-C 10 Cycloalkyl groups such as cyclohexyl, norbornyl, adamantyl, and the like.

[0110] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0111] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is an alkyl group, it is preferably C1-C30 alkyl group, and more preferably C1-C 24 Alkyl groups, C1-C 10 Alkyl group, C1-C4 alkyl group, such as methyl, ethyl, isopropyl, tert-butyl, etc.

[0112] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is an alkoxy group, it is preferably C1-C 24 Alkoxy groups.

[0113] Among them, when Ar a ,Ar b ,Ar 1 and Ar 2 When it is an aryloxy group, it is preferably C6-C 24 Aryloxy group.

[0114] X 1 is O or S,

[0115] a and r1 are independently integers from 0 to 4, b and r2 are independently integers from 0 to 3,

[0116] However, r1+r2≥1,

[0117] wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; and C8-C 20 and further, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60A heterocyclic group or a condensed ring formed by combining them.

[0118] However, Formula 2 contains at least one deuterium.

[0119] In addition, Formula 1 is represented by any one of the following Formulas 1-1 to Compound 1-4:

[0120]

[0121] in:

[0122] R a , R b , a, b, L a , L b , L c ,Ar a and Ar b Same as defined above,

[0123] R e , R f , R g , R h , R i and R j With R a The definition is the same as

[0124] X 2 is O or S,

[0125] c and d are independently integers from 0 to 5, and e, f, g and h are independently integers from 0 to 4.

[0126] Ar a and Ar b At least one of can be represented by Formula A-1.

[0127] <Formula A-1>

[0128]

[0129] in:

[0130] R k and R l With R a The definition of R is the same, or multiple adjacent R k or multiple R l can be bonded to each other to form a ring,

[0131] X 3 is O, S or CR'R",

[0132] Where R' and R" are c or R' and R" may be bonded to each other to form a spiro,

[0133] i is an integer from 0 to 3, and j is an integer from 0 to 3.

[0134] Formula A-1 is represented by any one of the following Formulas A-1-1 to A-1-4.

[0135]

[0136] Among them, X 3 , R k , R l , i and j are the same as defined in Formula A-1.

[0137] Ar 1 and Ar 2 At least one of them is represented by the following formula A-2 or formula A-3.

[0138]

[0139]

[0140] in:

[0141] R 3 , R 4 , R 5 , R 6 , R 7 and R 8 With R a or adjacent groups may be bonded to each other to form a ring,

[0142] However, when R 5 and R 6 When they are bonded to each other to form a ring, they form a single bond,

[0143] X 4 is O, S or CR'R",

[0144] Where R' and R" are c or R' and R" may be bonded to each other via a single bond to form a spiro,

[0145] r3, r5, r7 and r8 are each independently an integer from 0 to 4, r4 is an integer from 0 to 3, and r6 is an integer from 0 to 5.

[0146] However, when Ar 1 and Ar 2 When at least one of the compounds is a compound represented by formula A-2, it is preferred to exclude X 4 This is the case with NR'.

[0147] However, it is preferred to exclude Ar 1 and Ar 2At least one of the cases is represented by formula A-4.

[0148] <Formula A-4>

[0149]

[0150] in:

[0151] Y is O or S,

[0152] R 9 , R 10 , R 11 and R 12 With R 1 The same definition as R 11 and R 12 can be bonded to each other to form a ring,

[0153] r9 is an integer of 0-3, and r10 is an integer of 0-4.

[0154] Formula A-2 is represented by any one of the following Formulas A-2-1 to A-2-4.

[0155]

[0156] Among them, X 4 , R 3 , R 4 , r3 and r4 are the same as defined in formula A-2.

[0157] Formula A-3 is represented by the following Formula A-3-1 to Formula A-3-3.

[0158]

[0159] Among them, R 5 , R 6 , R 7 , R 8 , r5, r6, r7 and r8 are the same as defined in formula A-3.

[0160] L a , L b , L c , L 1 and L 2 They may be independently represented by a single bond or any one of the following Formulae L-1 to L-4.

[0161]

[0162]

[0163] in:

[0164] R A, R B , R C , R D , R E , R F and R G With R a or adjacent groups may be bonded to each other to form a ring,

[0165] X 5 and X 6 are each independently O or S,

[0166] ra, rb, rc and rf are each independently an integer from 0 to 4, rd and re are each independently an integer from 0 to 3, and rg is an integer from 0 to 2.

[0167] Formula L-1 is represented by any one of the following Formula L-1-1 to Formula L-1-3.

[0168]

[0169] Among them, R A and ra are the same as defined in formula L-1.

[0170] Formula L-2 is represented by any one of the following Formulas L-2-1 to L-2-6.

[0171]

[0172]

[0173] Among them, R B , R C , rb and rc are the same as those defined in Formula L-2. Formula L-3 is represented by any one of the following Formulas L-3-1 to L-3-9.

[0174]

[0175] Among them, X 5 , R D , R E , rd and re are the same as defined in formula L-3.

[0176] Formula L-4 is represented by any one of the following Formulas L-4-1 to L-4-3.

[0177]

[0178] Among them, X 6 , R F , R G , rf and rg are the same as defined in formula L-4.

[0179] Furthermore, the present invention provides an organic electronic component comprising a compound, wherein R 1 and R 2 At least one of is deuterium; or a substituent comprising deuterium;

[0180] Specifically, the compound represented by Formula 1 may be any one of the following compounds, but is not limited thereto.

[0181]

[0182]

[0183]

[0184]

[0185] Specifically, the compound represented by Formula 2 may be any one of the following compounds, but is not limited thereto.

[0186]

[0187]

[0188]

[0189]

[0190] The present invention may further include a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

[0191] In addition, the organic material layer may include 2 or more stacked bodies including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the 2 or more stacked bodies.

[0192] In addition, the present invention provides an electronic device comprising a display device including an organic electronic element; and a control unit for driving the display device, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochrome or white lighting.

[0193] Hereinafter, examples of synthesis of the compound represented by the formula according to the present invention and examples of manufacturing an organic electronic element will be described in detail through examples, but the present invention is not limited to the following examples.

[0194] [Synthesis example 1]

[0195] The compound represented by Formula 1 according to the present invention (final product 1) is synthesized by reacting Sub1 and Sub2 as shown in Reaction Scheme 1, but is not limited thereto.

[0196] <Reaction Scheme 1>

[0197]

[0198] in,

[0199] Hal 1 is Cl, Br or I,

[0200] G 1 Yes = L b -Ar a ,

[0201] G 2 Yes-L C -Ar b .

[0202] I. Synthesis of Sub1

[0203] The compounds belonging to Sub 1 of Reaction Scheme 1 may be the following compounds, but are not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub 1.

[0204]

[0205] [Table 1]

[0206] Compound FD-MS Compound FD-MS Sub1-1 <![CDATA[m / z=272.02(C 15 H 13 Br=273.17)]]> Sub1-2 <![CDATA[m / z=286.04(C 16 H 15 Br=287.2)]]> Sub1-3 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub1-4 <![CDATA[m / z=279.06(C 15 H6D7Br=280.22)]]> Sub1-5 <![CDATA[m / z=358.11(C 21 H7D 10 Br=359.33)]]> Sub1-6 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub1-7 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub1-8 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub1-9 <![CDATA[m / z=394.04(C 25 H 15 Br=395.3)]]> Sub1-10 <![CDATA[m / z=405.1(C 25 H4D 11 Br=406.37)]]> Sub1-11 <![CDATA[m / z=444.05(C 29 H 17 Br=445.36)]]> Sub1-12 <![CDATA[m / z=410.03(C 25 H 15 BrO=411.3)]]> Sub1-13 <![CDATA[m / z=460.05(C 29 H 17 BrO=461.36)]]> Sub1-14 <![CDATA[m / z=354.1(C 21 H 23 Br=355.32)]]>

[0207] II. Synthesis of Sub2

[0208] The compounds belonging to Sub 2 of Reaction Scheme 1 may be the following compounds, but are not limited thereto, and Table 2 shows the FD-MS values ​​of the compounds belonging to Sub 2.

[0209]

[0210]

[0211]

[0212] [Table 2]

[0213]

[0214]

[0215] III. Synthesis of Final Product 1

[0216] 1. Synthesis Example of P1-1

[0217]

[0218] In a round-bottom flask, Sub1-1 (10.0 g, 36.6 mmol) was dissolved in toluene (185 mL), Sub2-1 (11.8 g, 36.6 mmol), Pd2(dba)3 (1.01 g, 1.10 mmol), P(t-Bu)3 (0.44 g, 2.20 mmol), NaOt-Bu (7.0 g, 73.2 mmol) were added, and the reaction was carried out at 80°C. When the reaction was completed, extraction was carried out with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting organic material was recrystallized using a silica gel column to obtain 14.9 g of the product. (Yield 79%)

[0219] 2. Synthesis Example of P1-17

[0220]

[0221] In a round-bottom flask, Sub1-3 (10.0 g, 28.6 mmol) was dissolved in toluene (145 mL), Sub2-48 (9.6 g, 28.6 mmol), Pd2(dba)3 (0.79 g, 0.86 mmol), P(t-Bu)3 (0.35 g, 1.72 mmol), NaOt-Bu (5.5 g, 57.3 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 13.1 g of the product. (Yield 76%)

[0222] 3. Synthesis Example of P1-23

[0223]

[0224] In a round-bottom flask, Sub1-1 (10.0 g, 36.6 mmol) was dissolved in toluene (185 mL), Sub2-55 (13.7 g, 36.6 mmol), Pd2(dba)3 (1.01 g, 1.10 mmol), P(t-Bu)3 (0.44 g, 2.20 mmol), NaOt-Bu (7.0 g, 73.2 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 15.0 g of the product. (Yield 72%)

[0225] 4. Synthesis Example of P1-35

[0226]

[0227] In a round-bottom flask, Sub1-7 (10.0 g, 28.6 mmol) was dissolved in toluene (145 mL), Sub2-48 (9.6 g, 28.6 mmol), Pd2(dba)3 (0.79 g, 0.86 mmol), P(t-Bu)3 (0.35 g, 1.72 mmol), NaOt-Bu (5.5 g, 57.3 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 13.3 g of the product. (Yield 77%)

[0228] 5. Synthesis Example of P1-39

[0229]

[0230] In a round-bottom flask, Sub1-9 (10.0 g, 25.3 mmol) was dissolved in toluene (130 mL), Sub2-12 (9.1 g, 25.3 mmol), Pd2(dba)3 (0.69 g, 0.76 mmol), P(t-Bu)3 (0.31 g, 1.52 mmol), NaOt-Bu (4.9 g, 50.6 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 12.8 g of the product. (Yield 75%)

[0231] 6. Synthesis Example of P1-40

[0232]

[0233] In a round-bottom flask, Sub1-12 (10.0 g, 24.3 mmol) was dissolved in toluene (125 mL), Sub2-12 (8.8 g, 24.3 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol), P(t-Bu)3 (0.30 g, 1.46 mmol), NaOt-Bu (4.7 g, 48.6 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 12.8 g of the product. (Yield 76%)

[0234] 7. Synthesis Example of P1-42

[0235]

[0236] In a round-bottom flask, Sub1-1 (10.0 g, 36.6 mmol) was dissolved in toluene (185 mL), Sub2-8 (14.6 g, 36.6 mmol), Pd2(dba)3 (1.01 g, 1.10 mmol), P(t-Bu)3 (0.44 g, 2.20 mmol), NaOt-Bu (7.0 g, 73.2 mmol) were added, and the experiment was carried out in the same manner as in P1-1 to obtain 16.8 g of the product. (Yield 78%)

[0237] Meanwhile, the FD-MS values ​​of Compound P1-1 to Compound P1-52 of the present invention prepared according to the above Synthesis Examples are shown in Table 3.

[0238] [Table 3]

[0239] Compound FD-MS Compound FD-MS P1-1 <![CDATA[m / z=513.25(C 39 H 31 N=513.68)]]> P1-2 <![CDATA[m / z=513.25(C 39 H 31 N=513.68)]]> P1-3 <![CDATA[m / z=513.25(C 39 H 31 N=513.68)]]> P1-4 <![CDATA[m / z=513.25(C 39 H 31 N=513.68)]]> P1-5 <![CDATA[m / z=527.22(C 39 H 29 NO=527.67)]]> P1-6 <![CDATA[m / z=527.22(C 39 H 29 NO=527.67)]]> P1-7 <![CDATA[m / z=527.22(C 39 H 29 NO=527.67)]]> P1-8 <![CDATA[m / z=527.22(C 39 H 29 NO=527.67)]]> P1-9 <![CDATA[m / z=543.2(C 39 H 29 NS=543.73)]]> P1-10 <![CDATA[m / z=543.2(C 39 H 29 NS=543.73)]]> P1-11 <![CDATA[m / z=543.2(C 39 H 29 NS=543.73)]]> P1-12 <![CDATA[m / z=543.2(C 39 H 29 NS=543.73)]]> P1-13 <![CDATA[m / z=553.28(C 42 H 35 N=553.75)]]> P1-14 <![CDATA[m / z=553.28(C 42 H 35 N=553.75)]]> P1-15 <![CDATA[m / z=553.28(C 42 H 35 N=553.75)]]> P1-16 <![CDATA[m / z=553.28(C 42 H 35 N=553.75)]]> P1-17 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-18 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-19 <![CDATA[m / z=705.34(C 54 H 43 N=705.94)]]> P1-20 <![CDATA[m / z=581.31(C 44 H 39 N=581.8)]]> P1-21 <![CDATA[m / z=567.26(C 42 H 33 NO=567.73)]]> P1-22 <![CDATA[m / z=567.26(C 42 H 33 NO=567.73)]]> P1-23 <![CDATA[m / z=567.26(C 42 H 33 NO=567.73)]]> P1-24 <![CDATA[m / z=583.23(C 42 H 33 NS=583.79)]]> P1-25 <![CDATA[m / z=629.31(C 48 H 39 N=629.85)]]> P1-26 <![CDATA[m / z=629.31(C 48 H 39 N=629.85)]]> P1-27 <![CDATA[m / z=643.29(C 48 H 37 NO=643.83)]]> P1-28 <![CDATA[m / z=629.31(C 48 H 39 N=629.85)]]> P1-29 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-30 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-31 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-32 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-33 <![CDATA[m / z=589.28(C 45 H 35 N=589.78)]]> P1-34 <![CDATA[m / z=589.28(C 45 H 35 N=589.78)]]> P1-35 <![CDATA[m / z=603.26(C 45 H 33 NO=603.76)]]> P1-36 <![CDATA[m / z=629.31(C 48 H 39 N=629.85)]]> P1-37 <![CDATA[m / z=753.34(C 58 H 43 N=753.99)]]> P1-38 <![CDATA[m / z=751.32(C 58 H 41 N=751.97)]]> P1-39 <![CDATA[m / z=675.29(C 52 H 37 N=675.88)]]> P1-40 <![CDATA[m / z=691.29(C 52 H 37 NO=691.87)]]> P1-41 <![CDATA[m / z=525.34(C 39 H 43 N=525.78)]]> P1-42 <![CDATA[m / z=589.37(C 44 H 47 N=589.87)]]> P1-43 <![CDATA[m / z=537.34(C 40 H 43 N=537.79)]]> P1-44 <![CDATA[m / z=555.39(C 41 H 49 N=555.85)]]> P1-45 <![CDATA[m / z=725.31(C 56 H 39 N=725.93)]]> P1-46 <![CDATA[m / z=741.3(C 56 H 39 NO=741.93)]]> P1-47 <![CDATA[m / z=577.24(C 43 H 31 NO=577.73)]]> P1-48 <![CDATA[m / z=527.26(C 40 H 33 N=527.71)]]> P1-49 <![CDATA[m / z=576.42(C 42 H 12 D 23 N=576.89)]]> P1-50 <![CDATA[m / z=629.42(C 45 H7D 26 NO=629.92)]]> P1-51 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=788.56(C <h2 style=";text-align:left;direction:ltr"> 58 <h2 style=";text-align:left;direction:ltr"> H8D<h2 style=";text-align:left;direction:ltr"> 35 <h2 style=";text-align:left;direction:ltr"> N=789.2)]]><h2 style=";text-align:left;direction:ltr"> P1-52 <![CDATA[m / z=702.46(C 52 H 10 D 27 N=703.04)]]> P1-53 <![CDATA[m / z=635.36(C 48 H 45 N=635.89)]]> P1-54 <![CDATA[m / z=577.24(C 43 H 31 NO=577.73) <!-- 28 -->]]> P1-55 <![CDATA[m / z=630.3(C 45 H 22 D 11 NS=630.89)]]> P1-56 <![CDATA[m / z=583.29(C 43 H 37 NO=583.77)]]>

[0240] [Synthesis example 2]

[0241] The compound represented by Formula 2 according to the present invention (final product 2) is synthesized by reacting Sub3 and Sub4 as shown in Reaction Scheme 2, but is not limited thereto.

[0242] <Reaction Scheme 2>

[0243]

[0244] in,

[0245] Hal 2 is Cl, Br or I,

[0246] G 1 Yes-L 1 -Ar 1 ,

[0247] G 2 Yes-L 2 -Ar 2 .

[0248] I. Synthesis of Sub3

[0249] The compound belonging to Sub3 in Reaction Scheme 2 may be, but is not limited to, the following compounds, and Table 4 shows the FD-MS values ​​of the compounds belonging to Sub3.

[0250]

[0251] [Table 4]

[0252] Compound FD-MS Compound FD-MS Sub3-1 <![CDATA[m / z=253.01(C 12 D7BrO=254.13)]]> Sub3-2 <![CDATA[m / z=333.07(C 18 D 11 BrO=334.26)]]> Sub3-3 <![CDATA[m / z=333.07(C 18 D 11 BrO=334.26)]]> Sub3-4 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=418.05(C <h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H7D6BrO2 = 419.31<h2 style=";text-align:left;direction:ltr"> Sub3-5 <![CDATA[m / z=328.04(C 18 H5D6BrO=329.23)]]> Sub3-6 <![CDATA[m / z=328.04(C 18 H5D6BrO=329.23)]]> Sub3-7 <![CDATA[m / z=268.99(C 12 D7BrS=270.19)]]> Sub3-8 <![CDATA[m / z=344.01(C 18 H5D6BrS=345.29)]]> Sub3-9 <![CDATA[m / z=349.05(C 18 D 11 BrS=350.32)]]> Sub3-10 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=450(C <h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H7D6BrS2=451.43)]]><h2 style=";text-align:left;direction:ltr"> Sub3-11 <![CDATA[m / z=344.01(C 18 H5D6BrS=345.29)]]> Sub3-12 <![CDATA[m / z=344.01(C 18 H5D6BrS=345.29)]]>

[0253] II. Synthesis of Final Product 2

[0254] 1. Synthesis Example of P2-3

[0255]

[0256] In a round-bottom flask, Sub3-2 (10.0 g, 29.9 mmol) was dissolved in toluene (150 mL), Sub2-57 (13.8 g, 29.9 mmol), Pd2(dba)3 (0.82 g, 0.90 mmol), P(t-Bu)3 (0.36 g, 1.80 mmol), NaOt-Bu (5.8 g, 59.8 mmol) were added, and the reaction was carried out at 80°C. When the reaction was completed, it was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting organic material was recrystallized using a silica gel column to obtain 13.9 g of the product. (Yield 65%)

[0257] 2. Synthesis Example of P2-11

[0258]

[0259] In a round-bottom flask, Sub3-1 (10.0 g, 39.3 mmol) was dissolved in toluene (200 mL), Sub2-14 (17.2 g, 39.3 mmol), Pd2(dba)3 (1.08 g, 1.18 mmol), P(t-Bu)3 (0.48 g, 2.36 mmol), NaOt-Bu (7.6 g, 78.7 mmol) were added, and the same experiment as P2-3 was performed to obtain 17.3 g of the product. (Yield 72%)

[0260] 2. Synthesis Example of P2-18

[0261]

[0262] In a round-bottom flask, Sub3-1 (10.0 g, 39.3 mmol) was dissolved in toluene (200 mL), Sub2-65 (22.7 g, 39.3 mmol), Pd2(dba)3 (1.08 g, 1.18 mmol), P(t-Bu)3 (0.48 g, 2.36 mmol), NaOt-Bu (7.6 g, 78.7 mmol) were added, and the same experiment as P2-3 was performed to obtain 20.6 g of the product. (Yield 70%)

[0263] 4. Synthesis Example of P2-21

[0264]

[0265] In a round-bottom flask, Sub3-1 (10.0 g, 39.3 mmol) was dissolved in toluene (200 mL), Sub2-62 (17.0 g, 39.3 mmol), Pd2(dba)3 (1.08 g, 1.18 mmol), P(t-Bu)3 (0.48 g, 2.36 mmol), NaOt-Bu (7.6 g, 78.7 mmol) were added, and the same experiment as P2-3 was performed to obtain 17.1 g of the product. (Yield 72%)

[0266] 5. Synthesis Example of P2-42

[0267]

[0268] In a round-bottom flask, Sub3-7 (10.0 g, 37.0 mmol) was dissolved in toluene (185 mL), Sub2-23 (17.9 g, 37.0 mmol), Pd2(dba)3 (1.02 g, 1.11 mmol), P(t-Bu)3 (0.45 g, 2.22 mmol), NaOt-Bu (7.1 g, 74.0 mmol) were added, and the same experiment as P2-3 was performed to obtain 17.2 g of the product. (Yield 69%)

[0269] Meanwhile, the FD-MS values ​​of Compound P2-1 to Compound P2-52 of the present invention prepared according to the above Synthesis Examples are shown in Table 5.

[0270] [Table 5]

[0271] Compound FD-MS Compound FD-MS P2-1 <![CDATA[m / z=494.24(C 36 H 18 D7NO=494.64)]]> P2-2 <![CDATA[m / z=508.22(C 36 H 16 D7NO2=508.63)]]> P2-3 <![CDATA[m / z=715.4(C 51 H 13 D 22 NO2=715.98)]]> P2-4 <![CDATA[m / z=515.26(C 36 H9D 14 NO2=515.67)]]> P2-5 <![CDATA[m / z=534.27(C 39 H 22 D7NO=534.71)]]> P2-6 <![CDATA[m / z=614.33(C 45 H 22 D 11 NO=614.83)]]> P2-7 <![CDATA[m / z=584.25(C 42 H 20 D7NO2=584.73)]]> P2-8 <![CDATA[m / z=654.36(C 48 H 26 D 11 NO=654.9)]]> P2-9 <![CDATA[m / z=584.25(C 42 H 20 D7NO2=584.73)]]> P2-10 <![CDATA[m / z=726.36(C 54 H 26 D 11 NO=726.96)]]> P2-11 <![CDATA[m / z=610.3(C 45 H 26 D7NO=610.81)]]> P2-12 <![CDATA[m / z=631.32(C 45 H 17 D 14 NO2=631.83)]]> P2-13 <![CDATA[m / z=690.24(C 48 H 22 D7NO2S=690.87)]]> P2-14 <![CDATA[m / z=673.25(C 48 H 23 D6NO3=673.8)]]> P2-15 <![CDATA[m / z=600.23(C 42 H 20 D7NOS=600.79)]]> P2-16 <![CDATA[m / z=512.35(C 36 D 25 NO=512.75)]]> P2-17 <![CDATA[m / z=658.3(C 49 H 26 D7NO=658.85)]]> P2-18 <![CDATA[m / z=748.31(C 55 H 28 D7NO2=748.93)]]> P2-19 <![CDATA[m / z=584.25(C 42 H 20 D7NO2=584.73)]]> P2-20 <![CDATA[m / z=614.2(C 42 H 18 D7NO2S=614.77)]]> P2-21 <![CDATA[m / z=604.37(C 42 D 27 NO2=604.85)]]> P2-22 <![CDATA[m / z=584.25(C 42 H 20 D7NO2=584.73)]]> P2-23 <![CDATA[m / z=609.29(C 45 H 27 D6NO=609.8)]]> P2-24 <![CDATA[m / z=658.3(C 49 H 26 D7NO=658.85)]]> P2-25 <![CDATA[m / z=656.28(C 49 H 24 D7NO=656.84)]]> P2-26 <![CDATA[m / z=656.28(C 49 H 24 D7NO=656.84)]]> P2-27 <![CDATA[m / z=746.3(C 55 H 26 D7NO2=746.92)]]> P2-28 <![CDATA[m / z=656.28(C 49 H 24 D7NO=656.84)]]> P2-29 <![CDATA[m / z=656.28(C 49 H 24 D7NO=656.84)]]> P2-30 <![CDATA[m / z=558.23(C 40 H 18 D7NO2=558.69)]]> P2-31 <![CDATA[m / z=656.28(C 49 H 24 D7NO=656.84)]]> P2-32 <![CDATA[m / z=658.3(C 49 H 26 D7NO=658.85)<!-- 31 --> ]]> P2-33 <![CDATA[m / z=658.3(C 49 H 26 D7NO=658.85)]]> P2-34 <![CDATA[m / z=732.32(C 55 H 28 D7NO=732.93)]]> P2-35 <![CDATA[m / z=734.33(C 55 H 30 D7NO=734.95)]]> P2-36 <![CDATA[m / z=583.24(C 42 H 21 D6NO2=583.72)]]> P2-37 <![CDATA[m / z=510.21(C 36 H 18 D7NS=510.71)]]> P2-38 <![CDATA[m / z=510.21(C 36 H 18 D7NS=510.71)]]> P2-39 <![CDATA[m / z=550.25(C 39 H 22 D7NS=550.77)]]> P2-40 <![CDATA[m / z=665.3(C 48 H 31 D6NS=665.93)]]> P2-41 <![CDATA[m / z=626.28(C 45 H 26 D7NS=626.87)]]> P2-42 <![CDATA[m / z=672.26(C 49 H 24 D7NS=672.9)]]> P2-43 <![CDATA[m / z=749.3(C 55 H 31 D6NS=750)]]> P2-44 <![CDATA[m / z=580.2(C 39 H 20 D7NS2=580.81)]]> P2-45 <![CDATA[m / z=620.35(C 42 D 27 NOS=620.91)]]> P2-46 <![CDATA[m / z=600.23(C 42 H 20 D7NOS=600.79)]]> P2-47 <![CDATA[m / z=620.23(C 42 H 16 D 11 NS2=620.87)]]> P2-48 <![CDATA[m / z=855.29(C 61 H 33 D6NS2=856.15)]]> P2-49 <![CDATA[m / z=564.26(C 40 H 24 D7NS=564.8)]]> P2-50 <![CDATA[m / z=599.22(C 42 H 21 D6NOS=599.78)]]> P2-51 <![CDATA[m / z=566.35(C 39 H6D 23 NS=566.87)]]> P2-52 <![CDATA[m / z=599.22(C 42 H 21 D6NOS=599.78)]]>

[0272] Meanwhile, exemplary synthesis examples of the present invention represented by Formula 1 or Formula 2 have been described above, but these are all based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and those skilled in the art should easily understand that the above reactions can be carried out even when bonded to substituents other than those specified in the specific synthesis examples.

[0273] Manufacturing and evaluation of organic electronic components

[0274] [Example 1] Red organic light emitting device

[0275] First, a hole injection layer was formed by vacuum depositing 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as 2-TNATA) on an ITO layer (anode) formed on a glass substrate to a thickness of 70 nm, and N,N'-bis(1-naphthyl)-N,N'-bisphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as NPB) as a hole transport compound was vacuum deposited on the hole injection layer to a thickness of 70 nm to form a hole transport layer. Next, the compound P1-3 of the present invention was vacuum deposited on the hole transport layer to a thickness of 70 nm to form a first light-emitting auxiliary layer, and then the compound P2-11 of the present invention was vacuum deposited on the first light-emitting auxiliary layer to a thickness of 5 nm to form a second light-emitting auxiliary layer. Subsequently, on the second On the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as CPB) is used as a main material, and bis(1-phenylisoquinolyl)iridium acetylacetonate (hereinafter referred to as (piq)2Ir(acac)) is used as a dopant material, and a light-emitting layer with a thickness of 40nm is formed by vacuum deposition at a weight ratio of 95:5. Next, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (hereinafter referred to as BCP) is vacuum deposited on the light-emitting layer to a thickness of 30nm to form an electron transport layer. Then, LiF as a halogenated alkali metal is deposited on the electron transport layer to a thickness of 0.2nm to form an electron injection layer, and then Al is deposited on the electron injection layer to a thickness of 150nm to form a cathode to manufacture an organic electroluminescent device.

[0276] [Example 2] to [Example 40] and [Comparative Example 1]

[0277] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention shown in Table 6 were used instead of P1-3 and P2-11 as materials for the first and second light-emitting auxiliary layers.

[0278] For the organic electroluminescent devices manufactured by the examples and comparative examples, electroluminescent (EL) characteristics were measured by applying a forward bias DC voltage using PR-650 manufactured by PhotoResearch Co. As a result of the measurement, the lifetime measurement device manufactured by McScience measured the EL characteristics at 2,500 cd / m 2 Table 6 shows the results of the manufacturing evaluation of the element.

[0279] The measuring device is not affected by possible daily fluctuations in deposition rate, vacuum quality or other parameters and can evaluate the performance of new materials compared to comparative compounds under identical conditions.

[0280] In the evaluation, since one batch contained 4 identically prepared OLEDs containing comparative compounds and the performance of a total of 12 OLEDs was evaluated in 3 batches, the experimental results obtained in this way showed statistical significance.

[0281] [Table 6]

[0282]

[0283]

[0284] [Example 41] Green organic light-emitting device

[0285] First, 2-TNATA is vacuum deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 70nm to form a hole injection layer, and then NPB is vacuum deposited on the hole injection layer to a thickness of 70nm as a hole transport compound to form a hole transport layer. Subsequently, the compound P1-1 of the present invention is vacuum deposited on the hole transport layer to a thickness of 30nm to form the first luminescent auxiliary layer, and then the compound P2-3 of the present invention is vacuum deposited on the first luminescent auxiliary layer to a thickness of 5nm to form the second luminescent auxiliary layer. Subsequently, on the second luminescent auxiliary layer, CBP is used as a host material, and tris (2-phenylpyridine)-iridium is used as a dopant material, and a light-emitting layer is formed by vacuum deposition to a thickness of 40nm with a weight ratio of 95:5. Then, BCP is vacuum deposited on the light-emitting layer to a thickness of 30nm to form an electron transport layer. Then, LiF as a halogenated alkali metal was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[0286] [Example 42] to [Example 94] and [Comparative Example 2] to [Comparative Example 5]

[0287] An organic light-emitting device was manufactured in the same manner as in Example 41, except that the compounds of the present invention shown in Table 7 were used instead of P1-1 and P2-3 as materials for the first and second light-emitting auxiliary layers.

[0288]

[0289] For the organic electroluminescent devices manufactured by the examples and comparative examples, electroluminescent (EL) characteristics were measured by applying a forward bias DC voltage using PR-650 manufactured by PhotoResearch Co. As a result of the measurement, the lifetime measurement device manufactured by McScience was used at 5,000 cd / m 2Table 7 shows the results of the manufacturing evaluation of the element.

[0290] The measuring device is not affected by possible daily fluctuations in deposition rate, vacuum quality or other parameters and can evaluate the performance of new materials compared to comparative compounds under identical conditions.

[0291] In the evaluation, since one batch contained 4 identically prepared OLEDs containing comparative compounds and the performance of a total of 12 OLEDs was evaluated in 3 batches, the experimental results obtained in this way showed statistical significance.

[0292] [Table 7]

[0293]

[0294]

[0295]

[0296] It can be seen from the results of Tables 6 and 7 that, compared with the comparative example, when a red or green organic light-emitting device is manufactured by using the material for an organic light-emitting device of the present invention as a material for a light-emitting auxiliary layer, it can be confirmed that the compound of the present invention has an effect on improving the overall performance of the device, and in particular, it can be confirmed that the service life is significantly improved.

[0297] First, in the case of Comparative Examples 1 to 6, a compound having an amino group bonded to the 1-position of benzofuran or dibenzothiophene is used as the second luminescent auxiliary layer, and the difference of the compound of the present invention is that the second luminescent auxiliary layer is composed of a compound represented by Formula 2. To explain in more detail, in the case of the compound represented by Formula 2, the same thing is that it is a compound having an amino group bonded to the 1-position of dibenzofuran or dibenzothiophene, but the difference is that dibenzofuran or dibenzothiophene must be substituted by deuterium. When deuterium is substituted in this way, the second luminescent auxiliary layer may be affected by the degradation phenomenon or exciton occurring in the luminescent layer, and the stability against such degradation phenomenon or exciton is increased by deuterium, resulting in an increase in service life. In addition, when the amino group is bonded to the 1-position of dibenzofuran or dibenzothiophene, it shows a better service life than when the amino group is bonded at other positions, especially when deuterium is further substituted at the 1-position of dibenzofuran or dibenzothiophene, the synergistic effect seems to lead to a very significant service life.

[0298] Specifically, as can be seen in Comparative Example 3, if the first light-emitting auxiliary layer does not contain a compound in which an amino group is bonded to the 2-position of fluorene, the hole transport characteristics are significantly reduced, which reduces the driving voltage and efficiency of the entire device. Therefore, when the amino group is bonded to the 2-position of fluorene, it can be considered that it is very excellent in terms of driving voltage and efficiency.

[0299] In summary, as described above, the device composed of the first light-emitting auxiliary layer represented by Formula 1 and the second light-emitting auxiliary layer represented by Formula 2 shows very excellent characteristics in terms of driving voltage, efficiency and service life. Specifically, it can be seen that it is significantly excellent in terms of service life.

[0300] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be understood by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims, and should be interpreted as all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0301] [Digital description]

[0302] 100, 200, 300: organic electronic element 110: first electrode

[0303] 120: hole injection layer 130: hole transport layer

[0304] 140: Light-emitting layer 150: Electron transport layer

[0305] 160: electron injection layer 170: second electrode

[0306] 180: Light efficiency enhancement layer 210: Buffer layer

[0307] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0308] 330: first hole transport layer 340: first light emitting layer

[0309] 350: first electron transport layer 360: first charge generation layer

[0310] 361: second charge generation layer 420: second hole injection layer

[0311] 430: second hole transport layer 440: second light emitting layer

[0312] 450: Second electron transport layer CGL: Charge generation layer

[0313] ST1: first stack ST2: second stack

Claims

1. An organic electronic component comprising a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer comprises a hole transport layer formed between the first electrode and the light-emitting layer, and comprises a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, wherein the plurality of light-emitting auxiliary layers comprises a first light-emitting auxiliary layer and a second light-emitting auxiliary layer, wherein the first light-emitting auxiliary layer is adjacent to the hole transport layer, wherein the second light-emitting auxiliary layer is adjacent to the light-emitting layer, The first light-emitting auxiliary layer includes a compound represented by Formula 1, and the second light-emitting auxiliary layer includes a compound represented by Formula 2: <Formula 1> <Formula 2> in: R a , R b , R 1 and R 2 are independently the same or different and are independently selected from hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; or multiple adjacent R a and multiple R b can be bonded to each other to form a ring, R c and R d Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 an aryloxy group; or R c and R d may be bonded to each other to form a spiro ring, L a , L b , L c , L 1 and L 2 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; Ar a ,Ar b ,Ar 1 and Ar 2 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Cycloalkyl group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 Aryloxy groups; X 1 is O or S, a and r1 are independently integers from 0 to 4, b and r2 are independently integers from 0 to 3, However, r1+r2≥1, wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; and C8-C 20 and further, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by combining them, However, Formula 2 contains at least one deuterium.

2. The organic electronic device according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-4: in: R a , R b , a, b, L a , L b , L c ,Ar a and Ar b Same as defined in claim 1, R e , R f , R g , R h , R i and R j R of claim 1 a The definition is the same as X 2 is O or S, c and d are independently integers from 0 to 5, and e, f, g and h are independently integers from 0 to 4.

3. The organic electronic device according to claim 1, wherein R 1 and R 2 At least one of the compounds is deuterium or a substituent containing deuterium.

4. The organic electronic element according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following compounds:

5. The organic electronic element according to claim 1, wherein the compound represented by Formula 2 is represented by any one of the following compounds: 6 . The organic electronic element of claim 1 , further comprising a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 7 . The organic electronic element according to claim 1 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 8 . The organic electronic element according to claim 7 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies.

9. An electronic device comprising a display device including the organic electronic element according to claim 1; and a control unit for driving the display device.

10. The electronic device of claim 9, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white lighting.

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