Organic electrical component including multiple light-emitting auxiliary layers and electronic device including the same

Abstract

The present invention relates to an organic electrical component and an electronic device including the same. The organic electrical component includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode. The organic layer includes a plurality of light-emitting auxiliary layers. For the HOMO energy levels of the plurality of light-emitting auxiliary layers, in relation to the adjacent organic layers, they are defined under specific conditions, whereby the driving voltage, efficiency, and lifespan of the organic electrical component can be improved.

Description

Technical Field

[0001] The present invention relates to an organic electrical device including a plurality of light-emitting auxiliary layers and an electronic device including the same. More specifically, the present invention relates to an organic electrical device including a plurality of light-emitting auxiliary layers and an electronic device including the same, in which the HOMO energy level of each of the light-emitting auxiliary layers is lower than the HOMO energy level of the hole transport layer and higher than the HOMO energy level of the light-emitting layer. Technical Field

[0002] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using an organic substance. An organic electrical device using the organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer is generally formed as a multi-layer structure composed of various different substances in order to improve the efficiency and stability of the organic electrical device. For example, it may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like.

[0003] Generally, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated by recombination.

[0004] However, since the material for the hole transport layer should have a low HOMO value, most of them have a low T1 value. As a result, excitons generated in the light-emitting layer transition to the hole transport layer, ultimately leading to charge imbalance in the light-emitting layer. Therefore, there is a problem of light emission forming at the interface of the hole transport layer.

[0005] Therefore, in order to solve the problem of light emission in the hole transport layer, an organic electrical device having a plurality of hole transport layers formed or a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer has been proposed.

[0006] In Korean Patent Publication Nos. 10-2014-0001581, 10-2015-0023174, etc., an organic electrical device including a multi-layer structure of a hole transport layer is disclosed. Such an organic electrical device reduces the driving voltage of the device and improves the hole injection characteristics by doping a p-type doping substance into the hole transport layer having one kind of hole transporting substance or mixing a highly conductive hole injecting substance.

[0007] However, although this method can reduce the driving voltage of the element, it requires the use of a hole transporting material with high conductivity, resulting in excessive charge injection, which reduces the lifespan of the element. Moreover, the hole transporting material is prone to degradation due to the electrons injected into the element. As a result, light emission occurs near the interface between the hole transporting layer and the light emitting layer, and non-light-emitting quenching increases, still presenting the problem of low efficiency and lifespan of the element. Summary of the Invention

[0008] Technical Problem

[0009] Therefore, to solve the problems of the prior art, an object of the present invention is to provide an organic electrical element and an electronic device including the same. Regarding the above organic electrical element, a plurality of light emission assisting layers with a predetermined thickness are formed between the hole transporting layer and the light emitting layer, and the HOMO energy levels of these light emission assisting layers are appropriately adjusted by referring to the HOMO energy levels of adjacent organic layers. Thus, when forming the plurality of light emission assisting layers, even without using a p-type doping substance, the light emission efficiency, lifespan, etc. can be improved.

[0010] Technical Solution

[0011] In one aspect, the present invention provides an organic electrical element including a plurality of light emission assisting layers with a predetermined thickness, wherein the HOMO energy level of the light emission assisting layer is lower than the HOMO energy level of the hole transporting layer and higher than the HOMO energy level of the light emitting layer.

[0012] In another aspect, the present invention provides an electronic device including the above organic electrical element.

[0013] Technical Effect

[0014] According to the present invention, an organic electrical element and an electronic device including the same can be provided. In the above organic electrical element, a plurality of light emission assisting layers with a predetermined thickness are formed between the hole transporting layer and the light emitting layer, and the HOMO energy levels of these light emission assisting layers are adjusted to be lower than the HOMO energy level of the hole transporting layer and higher than the HOMO energy level of the light emitting layer. Thus, even without using a p-type doping substance and by using only a single substance to form each light emission assisting layer, the stability of the element can be improved, the light emission efficiency and lifespan can be enhanced, and there is no non-light-emitting quenching. Brief Description of the Drawings

[0015] Figure 1 It is a schematic configuration diagram of an organic electrical element according to an embodiment of the present invention.

[0016] Figure 2 It is a schematic configuration diagram of an organic layer showing the energy levels of an organic electrical element according to an embodiment of the present invention.

[0017] [Explanation of Reference Numerals]

[0018] 100: organic electric element 110: first electrode

[0019] 120: hole injection layer 130: hole transport layer

[0020] 140: Light-emitting layer 150: Electron transport layer

[0021] 160: electron injection layer 170: second electrode

[0022] 180: Light efficiency improvement layer 210: Buffer layer

[0023] 220: light-emitting auxiliary layer 221: first light-emitting auxiliary layer

[0024] 222: Second light-emitting auxiliary layer DETAILED DESCRIPTION

[0025] Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

[0026] In the process of adding reference numerals to the structural elements of each drawing, it is noted that the same structural elements are given the same reference numerals as much as possible even if they are shown in different drawings. In addition, in the process of describing the present invention, if it is judged that the detailed description of the relevant known structure or function will obscure the gist of the present invention, the detailed description will be omitted.

[0027] In the process of describing the structural elements of the present invention, the terms such as first, second, A, B, (a), (b) etc. may be used. Such terms are only used to distinguish from other structural elements, and the nature, order or sequence of the related structural elements will not be limited by such terms. When a structural element is "connected", "combined" or "coupled" to another structural element, the structural element can be directly connected or coupled to the other structural element, but it can also be understood that there are other structural elements "connected", "combined" or "coupled" between the structural elements.

[0028] Furthermore, when a structural element such as a layer, film, region, or plate is located "on" or "above" another structural element, this should be understood not only as being "directly above" the other structural element, but also as being other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood as being without other parts in between.

[0029] The terms "aryl" and "arylene" used in the present invention have carbon numbers of 6 to 60, unless otherwise specified, but are not limited thereto. In the present invention, aryl or arylene includes monocyclic types, ring aggregates, fused polycyclic types, and spiro compounds.

[0030] The term "fluorenyl" used in the present invention means a substituted or unsubstituted fluorenyl, and "fluorenylene" means a substituted or unsubstituted fluorenylene. The fluorenyl or fluorenylene used in the present invention includes a spiro compound formed by the mutual bonding between R and R' in the following structure, and also includes a cyclic compound formed by the mutual bonding between adjacent R". "Substituted fluorenyl" and "substituted fluorenylene" mean that at least one of the substituents R, R', and R" in the following structure is a substituent other than hydrogen, and R" in the following structure can be monovalent to octavalent. Regardless of the valence number, in this specification, fluorenyl, fluorenylene, and fluorenetriyl can all be named fluorenyl.

[0031]

[0032] The term "spirocyclic compound" used in the present invention means "spiro union", and spiro union means that two rings are connected by sharing only one atom. At this time, the atom shared in the two rings is called a "spiro atom", and according to the number of spiro atoms contained in a compound, these are respectively called "monospiro-", "dispiro-", "trispiro-" compounds.

[0033] The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene", but also non-aromatic rings. Unless otherwise specified, it means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" used in the present invention means N, O, S, P, or Si unless otherwise specified. The heterocyclic group means monocyclic, cyclic aggregates, fused polycyclic rings, spirocyclic compounds, etc. containing heteroatoms. In addition, it may also include compounds containing heteroatom groups such as SO2 and P=O in place of carbon forming the ring as in the following compounds.

[0034]

[0035] The term "alicyclic group" used in the invention means a cyclic hydrocarbon other than aromatic hydrocarbons, including monocyclic, cyclic aggregates, fused polycyclic rings, spirocyclic compounds, etc. Unless otherwise specified, it means a ring having 3 to 60 carbon atoms, but is not limited thereto. For example, when benzene as an aromatic ring and cyclohexane as a non-aromatic ring are fused, it also corresponds to an alicyclic ring.

[0036] In this specification, for the "base names" corresponding to aryl, arylene, heterocyclic group, etc., which are shown by examples of each symbol and its substituents, the "base name reflecting the valence" may be described, but it may also be described as the "parent compound name". For example, in the case of "phenanthrene" which is a kind of aryl, the monovalent "base" is "phenanthrenyl", the divalent base is "phenanthrenylene", etc. The base name may be described by distinguishing the valence, but regardless of the valence, it may also be described as "phenanthrene" which is the parent compound name. Similarly, in the case of pyrimidine, regardless of the valence, it may be described as "pyrimidine", or the "base name of this valence" may be described. For example, in the monovalent case, it may be described as pyrimidinyl, and in the divalent case, it may be described as pyrimidinylene, etc.

[0037] In addition, when describing the compound name or substituent name in the present invention, the numbers or letters indicating the position may also be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine may be described as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0038] And, as long as there is no clear description, the chemical formulas used in this specification can be applied in the same way as the definitions of the substituents defined by the exponents of the following chemical formulas.

[0039]

[0040] Among them, when a is an integer of 0, the substituent R 1 does not exist. That is, when a is 0, it means that the carbons forming the benzene ring are all bonded to hydrogens. In this case, the representation of the hydrogens bonded to the carbons may be omitted, and the chemical formula or compound may be described. And when a is an integer of 1, one substituent R 1 is bonded to one of the carbons used to form the benzene ring. When a is an integer of 2 or 3, they are bonded in the following ways respectively. When a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar way. When a is an integer of 2 or more, R 1 may be the same as or different from each other.

[0041]

[0042] And, in this specification, as long as there is no other description, when representing a condensed ring, the number in 'number-condensed ring' represents the number of condensed rings. For example, the form in which three rings such as anthracene, phenanthrene, and benzoquinazoline are condensed with each other may be shown as 3-condensed ring.

[0043] Also, in this specification, unless otherwise specified, when a ring is represented in the form of 'digital atoms' such as a five-membered ring or a six-membered ring, the number in 'number-atom' represents the number of elements forming the ring. For example, thiophene or furan corresponds to a five-membered ring, and benzene or pyridine corresponds to a six-membered ring.

[0044] Also, in this specification, unless otherwise specified, a ring formed by the combination of adjacent groups with each other is selected from C6-C 60 aromatic ring group; fluorenyl group; C2-C containing at least one heteroatom selected from O, N, S, Si, and P 60 heterocyclic group; and C3-C 60 aliphatic ring group.

[0045] At this time, in this specification, unless otherwise specified, 'between adjacent groups' means that, taking the following chemical formula as an example, not only between R1 and R2, between R2 and R3, between R3 and R4, between R5 and R6, but also between R7 and R8 sharing one carbon, and may also include substituents bonded to ring-constituting elements (such as carbon or nitrogen) that are not directly adjacent, such as between R1 and R7, between R1 and R8, or between R4 and R5. That is, when there is a substituent in a ring-constituting element such as directly adjacent carbon or nitrogen, it can be an adjacent group, but when there is no substituent bonded to the ring-constituting element at the directly adjacent position, it can form an adjacent group with the substituent bonded to the next ring-constituting element, and substituents bonded to the same ring-constituting carbon can also be called adjacent groups.

[0046] In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, combine with each other to form a ring, a compound containing a spiro ring part can be formed.

[0047]

[0048] Moreover, in this specification, the expression 'adjacent groups can combine with each other to form a ring' is used with the same meaning as 'adjacent groups can combine with each other to selectively form a ring', and means the case where at least one pair of adjacent groups combines with each other to form a ring.

[0049] Moreover, in this specification, unless otherwise specified, aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and a ring formed by the combination of adjacent groups with each other can each optionally be selected from deuterium, halogen, amino group substituted or unsubstituted by C1-C 20 alkyl group or C6-C 20 aryl group, and amino group substituted or unsubstituted by C1-C 20 alkyl group or C6-C 20Aryl-substituted or unsubstituted silyl, C1-C 20 alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxide, siloxanyl, cyano, nitro, C1-C 20 alkylthio, C1-C 20 alkoxy, C6-C 20 aryloxy, C6-C 20 arylthio, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, and C3-C 20 aliphatic cyclic group are further substituted by one or more substituents selected from the group consisting of these.

[0050] Figure 1 FIG. is an exemplary diagram of an organic electroluminescent device according to an embodiment of the present invention.

[0051] Referring to Figure 1 , an organic electrical device 100 according to an embodiment of the present invention includes: a first electrode 110 formed on a substrate (not shown), a second electrode 170, and an organic layer formed between the first electrode 110 and the second electrode 170.

[0052] The first electrode 110 may be an anode, and the second electrode 170 may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0053] The organic 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. A light-emitting auxiliary layer 220 may be formed between the hole transport layer 130 and the light-emitting layer 140. In addition, a buffer layer 210 may be formed between the hole transport layer 130 and the light-emitting auxiliary layer 220.

[0054] Specifically, the hole injection layer 120, the hole transport layer 130, the buffer layer 210, the light-emitting auxiliary layer 220, the light-emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.

[0055] Preferably, on either side of the first electrode 110 or the second electrode 170, a light efficiency improvement layer 180 may be formed on the side not in contact with the organic layer. In the case of forming the light efficiency improvement layer 180, the light efficiency of the organic electrical device can be improved.

[0056] For example, a light efficiency improvement layer 180 may be formed on the second electrode 170. However, in the case of a top-emission organic light-emitting diode, the formation of the light efficiency improvement layer 180 can reduce the optical energy loss caused by surface plasmon polaritons (SPPs) in the second electrode 170. In the case of a bottom-emission organic light-emitting diode, the light efficiency improvement layer 180 can act as a buffer for the second electrode 170.

[0057] Although not shown in Figure 1 , an electron transport auxiliary layer may also be formed between the light-emitting layer 140 and the electron transport layer 150.

[0058] Referring to Figure 2 , the light-emitting auxiliary layer 220 according to the present invention will be described in more detail.

[0059] Figure 2 FIG. is a schematic configuration diagram of an organic layer showing the energy levels of an organic electrical component according to an embodiment of the present invention.

[0060] Referring to Figure 2 , the organic layer according to an embodiment of the present invention includes a plurality of light-emitting auxiliary layers. Figure 2 FIG. shows an organic layer including two light-emitting auxiliary layers. The plurality of light-emitting auxiliary layers 220 include a first light-emitting auxiliary layer 221 adjacent to the hole transport layer 130 and a second light-emitting auxiliary layer 222 adjacent to the light-emitting layer 140.

[0061] Preferably, the HOMO energy level of the light-emitting auxiliary layer 220 is lower than the HOMO energy level of the hole transport layer 130 and higher than the HOMO energy level of the light-emitting layer 140. The HOMO energy level of the first light-emitting auxiliary layer 221 is higher than the HOMO energy level of the second light-emitting auxiliary layer 222.

[0062] The HOMO value is negative. Therefore, "lower HOMO energy level" means a larger absolute value. Therefore, preferably, the absolute value of the HOMO energy level of the light-emitting auxiliary layer 220 according to the present invention is larger than the absolute value of the HOMO energy level of the hole transport layer 130 and smaller than the absolute value of the HOMO energy level of the light-emitting layer 140. The absolute value of the HOMO energy level of the first light-emitting auxiliary layer 221 is smaller than the absolute value of the HOMO energy level of the second light-emitting auxiliary layer 222.

[0063] Preferably, the first light-emitting auxiliary layer 221 is formed of a single compound without additional doping, and the thickness is The second light-emitting auxiliary layer 222 is also formed of a single compound without additional doping, and the thickness is The total thickness of the above-mentioned light-emitting auxiliary layer is Among them, "additional doping" may mean doping with a p-doping substance.

[0064] In this way, the light-emitting auxiliary layer 220 of the present invention is formed of only one compound without additional doping with a p-doping substance or the like, but in relation to the adjacent organic layer, it is formed with a suitable HOMO energy level and a predetermined thickness, so that the life and efficiency of the organic electrical element can be improved.

[0065] Preferably, the HOMO energy level of the above-mentioned first light-emitting auxiliary layer 221 is 0.01 to 0.5 eV higher than the HOMO energy level of the second light-emitting auxiliary layer 222, and the HOMO energy levels of the first light-emitting auxiliary layer 221 and the second light-emitting auxiliary layer 222 are 5.50 to 5.69 eV respectively based on the absolute value. That is, the HOMO energy levels of the first light-emitting auxiliary layer 221 and the second light-emitting auxiliary layer 222 have values of -5.69 eV or more and -5.50 eV or less respectively, and it is preferable that the HOMO energy level of the first light-emitting auxiliary layer 221 is higher than the HOMO energy level of the second light-emitting auxiliary layer 222.

[0066] Preferably, the light-emitting layer according to the present invention is a red light-emitting layer or a green light-emitting layer.

[0067] According to another embodiment of the present invention, the organic layer may also be in a form in which a plurality of stacks are formed, and the stack includes a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, and an electron transport layer.

[0068] Generally, organic electroluminescent elements can be classified into single-emission structure elements (Single OLED) and multi-layer emission structure elements (Tandem OLED) according to the number of light-emitting parts. The multi-layer emission structure element (Tandem OLED), as an OLED element composed of two or more light-emitting parts (stacks), is easier to improve the driving voltage and efficiency compared with the existing single-emission structure element (Single OLED).

[0069] Specifically, the organic electrical element according to an embodiment of the present invention may include a first electrode, a first stack formed on the first electrode, a second stack formed on the first stack, and a second electrode. Among them, the so-called stack may correspond to the organic layer, and a light efficiency improvement layer may also be formed on the surface that does not contact the organic layer among the two surfaces of the first electrode and / or the second electrode.

[0070] The first stack and the second stack are organic layers respectively including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the first stack and the second stack may be formed into the same or different stacked structures.

[0071] In the first stack and the second stack, at least one of the stacks includes a plurality of light-emitting auxiliary layers according to the present invention. That is, a plurality of light-emitting auxiliary layers according to the present invention are included between the hole transport layer and the light-emitting layer, and such light-emitting auxiliary layers may be included in the first stack and / or the second stack.

[0072] In addition, 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 and a second charge generation layer. Such a charge generation layer CGL is formed between the light-emitting layers of the first stack and the second stack, increases the current efficiency generated in each light-emitting layer, and functions to smoothly distribute charges.

[0073] Stacks of two or more of these organic layers may be formed. For example, when forming a three-layer stack, a charge generation layer CGL and a third stack may be further stacked on the second stack.

[0074] In this way, when forming a plurality of light-emitting layers by means of a multi-layer stack structure, not only can an organic electroluminescent element that emits white light by means of the mixed effect of the light emitted by each light-emitting layer be manufactured, but also an organic electroluminescent element that emits light of various colors can be manufactured.

[0075] Since the organic layers of the present invention use a variety of polymer materials, they are made into a smaller number of layers by a solvent treatment or solvent purification method other than the evaporation method, such as spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, blade coating, screen printing, or thermal transfer methods. Since the organic layers of the present invention can be formed by a variety of methods, the scope of protection of the present invention is not limited by the formation method.

[0076] The organic electrical element according to an embodiment of the present invention can be classified into a front emission type, a back emission type, or a double-sided emission type according to the materials used.

[0077] And, the organic electrical element according to an embodiment of the present invention is selected from the group consisting of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, a monochromatic lighting element, and a quantum dot display element.

[0078] Another embodiment of the present invention may include an electronic device, the electronic device including: a display device including the organic electrical element of the present invention; and a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigators, game consoles, various TVs, and various computers.

[0079] According to the present invention, the HOMO energy level of the light-emitting auxiliary layer 220 is lower than that of the hole transport layer 130 and higher than that of the light-emitting layer 140.

[0080] Preferably, the plurality of light-emitting auxiliary layers according to the present invention include a first light-emitting auxiliary layer adjacent to the hole transport layer and a second light-emitting auxiliary layer adjacent to the light-emitting layer, and the first light-emitting auxiliary layer and the second light-emitting auxiliary layer include a compound represented by the following Chemical Formula 1 or a compound represented by the following Chemical Formula 2.

[0081] At this time, preferably, the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are formed of different compounds. That is, even if both the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are formed of a compound represented by the following Chemical Formula 1 or both are formed of a compound represented by the following Chemical Formula 2, it is preferred that each light-emitting auxiliary layer is formed of a different compound.

[0082]

[0083]

[0084] In the above Chemical Formulas 1 and 2, each symbol can be defined as follows.

[0085] Ar 1 to Ar 7 are independently selected from the group consisting of aryl groups having 6 to C 60 ; fluorenyl groups; heterocyclic groups having 2 to C 60 containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and aliphatic cyclic groups having 3 to C 60 , and Ar 4 and Ar 5 can be bonded to each other to form a ring, and Ar 6 and Ar 7 can be bonded to each other to form a ring. When Ar 4 and Ar 5 are bonded to each other or Ar 6 and Ar 7 are bonded to each other to form a ring, an N in the skeleton directly or indirectly connected to them can be included to form a heterocycle containing N.

[0086] When Ar 1 to Ar 7 are aryl groups, Ar 1 to Ar 7 can be, preferably, aryl groups having 6 to C 30 , more preferably, aryl groups having 6 to C 18 , for example, benzene, biphenyl, naphthalene, terphenyl, phenanthrene, anthracene, benzophenanthrene, pyrene, etc.

[0087] In the case where Ar 1 to Ar 7 is a heterocyclic group, Ar 1 to Ar 7 can be, preferably, a C2-C 30 heterocyclic group, more preferably, can be a C2-C 26 heterocyclic group, for example, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, thiophene, pyrrole, thiazole, indene, indole, phenyl-indole, benzindole, phenyl-benzindole, benzofuran, benzothiophene, benzimidazole, benzothiazole, benzoxazole, benzothiazole, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, phenanthroline, benzonaphthothiophene, benzonaphthofuran, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuranopyrimidine, benzothiophenopyrimidine, etc.

[0088] In the case where Ar 1 to Ar 7 is an aliphatic cyclic group, Ar 1 to Ar 7 can be, preferably, a C3-C 20 aliphatic cyclic group, more preferably, can be a C6-C 16 aliphatic cyclic group, for example, cyclohexane, fluoranthene, etc.

[0089] In the case where Ar 1 to Ar 7 is a fluorenyl group, Ar 1 to Ar 7 can be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)-9-phenyl-9H-fluorene, etc.

[0090] L 1 to L 7 are independently selected from the group consisting of a single bond; a C6-C 60 arylene group; a fluorenylene group; a C3-C 60 aliphatic cyclic group; and a C2-C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P.

[0091] In the case where L 1 to L 7 is an arylene group, L 1 to L7 is, preferably, C6-C 30 arylene, more preferably, more preferably, C6-C 18 arylene, for example, benzene, biphenyl, naphthalene, terphenyl, pyrene, phenanthrene, etc.

[0092] In the case where L 1 to L 7 is a heterocyclic group, L 1 to L 7 can be, preferably, a heterocyclic group of C2-C 30 more preferably, can be a heterocyclic group of C2-C 22 heterocyclic group, for example, carbazole, phenylcarbazole, naphthylcarbazole, dibenzothiophene, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, etc.

[0093] In the case where L 1 to L 7 is an indenylidene group, L 1 to L 7 can be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0094] L 8 is selected from the group consisting of C6-C 60 arylene; indenylidene group; C3-C 60 aliphatic cyclic group; and a C2-C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P.

[0095] In the case where L 8 is an aryl group, L 8 can be, preferably, a C6-C 30 arylene, more preferably, more preferably, C6-C 18 arylene, for example, benzene, biphenyl, naphthalene, terphenyl, anthracene, phenanthrene, pyrene, etc.

[0096] In the case where L 8 is a heterocyclic group, L 8 can be, preferably, a C2-C 30 heterocyclic group, more preferably, can be a C2-C 18 heterocyclic group, for example, dibenzothiophene, dibenzofuran, benzonaphthofuran, benzonaphthothiophene, carbazole, phenylcarbazole, etc.

[0097] In the case where L 8 is a fluorenyl group, L8 It may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)-9-phenyl-9H-fluorene, etc.

[0098] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic group, aliphatic cyclic group, Ar 4 and Ar 5 The rings formed by mutual combination between them, Ar 6 and Ar 7 The rings formed by mutual combination between them can each optionally be selected from the group consisting of deuterium, halogen, silyl, siloxanyl, cyano, nitro, C1-C 20 alkyl or C6-C 20 aryl-substituted or unsubstituted, alkylthio group of C1-C 20 , alkoxy group of C1-C 20 , aryloxy group of C6-C 20 , arylthio group of C6-C 20 , alkyl group of C1-C 20 , alkenyl group of C2-C 20 , alkynyl group of C2-C 20 , aryl group of C6-C 20 , fluorenyl group, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 , heterocyclic group of C3-C 20 , aliphatic cyclic group of C3-C a )(R b ) and further substituted by one or more substituents in the group.

[0099] The above L' is selected from the group consisting of a single bond; C6-C 20 , arylene; fluorenylene; C3-C 20 , aliphatic cyclic group; and C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 , heterocyclic group in the group.

[0100] The above R a and R b are independently selected from the group consisting of aryl group of C6-C 20 , fluorenyl group; C3-C 20 , aliphatic cyclic group; and C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 , heterocyclic group in the group.

[0101] The above Chemical Formula 1 is represented by the following Chemical Formula A-1 or Chemical Formula A-2.

[0102]

[0103] In the above Chemical Formula A-1 and Chemical Formula A-2, each symbol can be defined in the following manner.

[0104] L 1 to L 3 、Ar 2 、Ar 3 have the same definitions as those in Chemical Formula 1.

[0105] Y1 and Y2 are a single bond, O, S, or C(R5)(R6), and the case where both Y1 and Y2 are single bonds is excluded.

[0106] R1 to R6, Z1, and Z2 are independently selected from the group consisting of deuterium, halogen, a C1-C 20 alkyl or a C6-C 20 aryl-substituted or unsubstituted silyl group, siloxanyl group, cyano group, nitro group, a C1-C 20 alkylthio group, a C1-C 20 alkoxy group, a C6-C 20 aryloxy group, a C6-C 20 arylthio group, a C1-C 20 alkyl group, a C2-C 20 alkenyl group, a C2-C 20 alkynyl group, a C6-C 20 aryl group, fluorenyl group, a C2-C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ). Adjacent groups can combine with each other to form a ring, R5 and R6 can combine with each other to form a ring, and Z1 and Z2 can combine with each other to form a ring. When R5 and R6 combine with each other or Z1 and Z2 combine with each other, a spiro compound can be formed, for example, a spirofluorene can be formed.

[0107] a, c, and d are each an integer from 0 to 4, b is an integer from 0 to 3, and when these are each an integer of 2 or more, R1, R2, R3, and R4 are each the same or different.

[0108] The aryl group, fluorenyl group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, ring formed by the combination of adjacent groups, ring formed by the combination of R5 and R6, and ring formed by the combination of Z1 and Z2 can each optionally be selected from the group consisting of deuterium, halogen, cyano group, nitro group, C1-C 20 alkoxy group, C6-C 20 aryloxy group, C1-C 20 alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C6-C 20 aryl group, fluorenyl group, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ) and further substituted by one or more substituents selected from the group, and the above L', R a and R b have the same definitions as those in Chemical Formula 1.

[0109] The above Chemical Formula A-1 is represented by one of the following Chemical Formula A-3 or Chemical Formula A-6.

[0110]

[0111]

[0112] In the above Chemical Formulas A-3 to A-6, each symbol can be defined as follows.

[0113] L 1 to L 3 , Ar 2 , Ar 3 , R1, R2, a, b, Y1 have the same definitions as those in the above Chemical Formula A-1, and Y3 has the same definition as Y1.

[0114] R 1’ and R 2’ are independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C1-C 20 alkoxy group, C6-C 20 aryloxy group, C1-C 20 alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C6-C 20 aryl group, fluorenyl group, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C20 an aliphatic cyclic group and -L'-N(R a )(R b ), where L', R a and R b are as defined in Chemical Formula 1.

[0115] m is an integer from 0 to 4, n is an integer from 0 to 3, and when these are integers of 2 or more, R 1’ respectively, R 2’ are respectively the same or different.

[0116] The above Chemical Formula 2 is represented by the following Chemical Formula B-1.

[0117] <Chemical Formula B-1>

[0118]

[0119] In the above Chemical Formula B-1, each symbol can be defined as follows.

[0120] L 4 to L 7 , Ar 4 , Ar 5 , Ar 7 are as defined in Chemical Formula 2.

[0121] The A ring, B ring, C ring, and D ring are each independently selected from the group consisting of a C6-C 20 aromatic cyclic group, a fluorenyl group, a C2-C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and a C3-C 20 aliphatic cyclic group, and these can each be further substituted by one or more Rs.

[0122] X1 and X2 are each independently O, S, N(Ar), or C(R7)(R8).

[0123] L a to L e are each independently selected from the group consisting of a single bond; a C6-C 20 arylene group; a fluorenylene group; a C2-C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a C3-C 20 aliphatic cyclic group.

[0124] Ar d , Ar e and the above Ar are each independently selected from the group consisting of a C6-C 20aryl; fluorenyl; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group; and C3-C 20 aliphatic cyclic group.

[0125] The above R, R7, and R8 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 20 alkoxy, C6-C 20 aryloxy, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, and C3-C 20 aliphatic cyclic group, and R7 and R8 may combine with each other to form a ring.

[0126] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic group, aliphatic cyclic group, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and the ring formed by the combination of R7 and R8 can each optionally be selected from deuterium, halogen, cyano, nitro, C1-C 20 alkoxy, C6-C 20 aryloxy, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ) and further substituted by one or more substituents in the group, and the above L', R a and R b are the same as defined in Chemical Formula 2.

[0127] The above Chemical Formula B-1 is represented by one of the following Chemical Formulas B-2 to B-6.

[0128]

[0129]

[0130] In the above Chemical Formulas B-2 to B-6, Ar 4 、Ar 5, Ar 7 , Ar d , Ar e , X1, X2 have the same definitions as those in Chemical Formula B-1.

[0131] Preferably, when the above first light-emitting auxiliary layer is composed of a compound represented by Chemical Formula 1 or Chemical Formula 2, at least one of Ar 1 to Ar 7 and L 8 is represented by the following Chemical Formula 3.

[0132] <Chemical Formula 3>

[0133]

[0134] In the above Chemical Formula 3, each symbol can be defined in the following manner.

[0135] * represents the bonding position. X is N, N-(L a -Ar a ), O, S or C(R')(R”).

[0136] When Ar 1 to Ar 3 of Chemical Formula 1 is the above Chemical Formula 3, when X is N-(L a -Ar a ), O, S or C(R')(R”), L 1 to L 3 binds to the carbon represented by * in the above Chemical Formula 3. When X is N, L 1 to L 3 binds to X.

[0137] When Ar 4 to Ar 7 of Chemical Formula 2 is the above Chemical Formula 3, when X is N-(L a -Ar a ), O, S or C(R')(R”), L 4 to L 7 binds to the carbon represented by * in the above Chemical Formula 3. When X is N, L 4 to L 7 binds to X.

[0138] When L 8 of Chemical Formula 2 is the above Chemical Formula 3, when X is N-(L a -Ar a ), O, S or C(R')(R”), each N in the main chain binds to the carbon represented by * in the above Chemical Formula 3. When X is N, one of the two Ns in the main chain binds to X, and the other of the two Ns binds to the carbon represented by * in the above Chemical Formula 3.

[0139] R 1 、R 2 、R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C1-C 20 alkylthio, C1-C 20 alkoxy, C6-C 20 aryloxy, C6-C 20 arylthio, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ), and adjacent groups may combine with each other to form a ring, and R' and R'' may combine with each other to form a ring. L', R a and R b are as defined above.

[0140] a and b are each independently an integer from 0 to 4, and when these are integers of 2 or more, R 1 respectively, R 2 respectively are the same or different.

[0141] The above L a is selected from the group consisting of a single bond; C6-C 20 arylene; fluorenylene; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group; and C3-C 20 aliphatic cyclic group.

[0142] The above Ar a is selected from the group consisting of C6-C 20 aryl; fluorenyl; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group; and C3-C 20 aliphatic cyclic group.

[0143] Preferably, when the above second light-emitting auxiliary layer is composed of a compound represented by Chemical Formula 1 or Chemical Formula 2, the above Ar 1 to Ar 7 are C6-C 24 aryl, and L 8 is C6-C 24arylene group.

[0144] In addition, preferably, when the second light-emitting auxiliary layer is composed of a compound represented by Chemical Formula 1 or Chemical Formula 2, the above Ar 1 to Ar 7 and L 8 at least one of them may be dibenzofuran.

[0145] The first light-emitting auxiliary layer and the second light-emitting auxiliary layer may be formed of different compounds, and the first light-emitting auxiliary layer may include the compound represented by the above Chemical Formula A-1.

[0146] Specifically, the compound represented by the above Chemical Formula 1 may be one of the following compounds, but is not limited thereto.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Specifically, the compound represented by the above chemical formula 2 may be one of the following compounds, but is not limited thereto.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] Hereinafter, examples will be given to specifically illustrate the synthesis examples of the compounds represented by Chemical Formula 1 and Chemical Formula 2 of the present invention and the preparation examples of organic electrical components, but the present invention is not limited to the following examples.

[0190] Synthesis Example

[0191] [Synthesis Example 1] Compound Represented by Chemical Formula 1

[0192] The compound (Final Product 1) represented by Chemical Formula 1 according to the present invention was prepared by the synthesis methods disclosed in the Korean authorized patent 10-1786749 (authorized and announced on October 11, 2017), Korean patent application 2014-0152779 (filed on November 5, 2014), and Korean patent application 2014-0161275 (filed on November 19, 2014) of the present applicant.

[0193] <Reaction Formula 1> (Hal 1 is I, Br, or Cl.)

[0194]

[0195] Synthesis Example of Sub1

[0196] Sub1 in the above Reaction Formula 1 can be synthesized by the following Reaction Formula 2, but is not limited thereto.

[0197] <Reaction Formula 2> (Hal is I, Br, or Cl)

[0198]

[0199] 1. Synthesis Example of Sub1A-58

[0200]

[0201] Add [1,1'-biphenyl]-4-amine (50 g, 295.5 mmol), 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene (95.5 g, 295.5 mmol), Pd2(dba)3 (8.12 g, 8.9 mmol), P(t-Bu)3 (3.59 g, 17.7 mmol), NaOt-Bu (56.8 g, 590.9 mmol), and toluene (1,477 mL) into a round-bottom flask, and react at 100 °C. After the reaction is completed, extract with CH2Cl2 and water, dry and concentrate the organic layer with MgSO4, and then separate the generated organic matter by silica gel column and perform recrystallization to obtain 87.5 g of the product (yield: 72%).

[0202] Synthesis Example of Sub1A-59

[0203]

[0204] Aniline (50 g, 536.9 mmol), 3-bromonaphtho[2,3-b]benzofuran (158.9 g, 536.9 mmol), Pd2(dba)3 (14.75 g, 16.1 mmol), P(t-Bu)3 (6.52 g, 32.2 mmol), NaOt-Bu (103.2 g, 1,073.8 mmol) and toluene (2,684 mL) were added to a round-bottom flask, and the reaction was carried out in the same manner as the synthesis method of Sub1A-58 described above to obtain 129.5 g of the product (yield: 78%).

[0205] Synthesis Example of Sub1C-18

[0206]

[0207] 3-(9-Phenyl-9H-fluoren-9-yl)aniline (43 g, 128.96 mmol), 4-bromodibenz[b,d]furan (33.5 g, 135.4 mmol), Pd2(dba)3 (3.5 g, 3.8 mmol), P(t-Bu)3 (1.6 g, 7.7 mmol), NaOt-Bu (37.2 g, 386.9 mmol) and toluene (1,322 mL) were added to a round-bottom flask, and the reaction was carried out in the same manner as the synthesis method of Sub1A-58 described above to obtain 55.5 g of the product (yield: 86.2%).

[0208] The compound belonging to Sub1 may be the same as the following compounds, but is not limited thereto. The FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1 respectively.

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] [Table 1]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226] Synthesis Example of Sub2

[0227] Sub2 of the above Reaction Formula 1 can be synthesized by the following Reaction Formula 3, but is not limited thereto.

[0228] [Reaction Formula 3](Hal 1 and Hal 2 are each independently selected from I, Br or Cl.)

[0229]

[0230] 1. Synthesis Example of Sub2B-1

[0231]

[0232] (1) Synthesis Example of Sub2B-1-a

[0233] 5-Chloro-2-iodobenzoic acid (50.0 g, 177 mmol), phenol (33.3 g, 354 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (80.9 g, 531 mmol), pyridine (2.9 mL), copper powder (1.5 g, 23 mmol) and CuI (1.5 g, 7.97 mmol) were placed in a round-bottom flask, and DMF (1.2 L) was added, followed by refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and HCl (3 M) was added until precipitation was complete. Thereafter, the precipitate was washed with water and dried to obtain 38.3 g of the product (yield: 87%).

[0234] (2) Synthesis Example of Sub2B-1-b

[0235] Sub2B-1-a (38.3 g, 154 mmol) was placed in a round-bottom flask, and H2SO4 (1.1 mL, 21.5 mmol) was added. The mixture was refluxed until all the starting materials were dissolved. After all the starting materials were dissolved, it was cooled to room temperature and then precipitated with ice water. Thereafter, the precipitate was washed with water, dried and dissolved in CH2Cl2. After that, it was separated by a silica gel column and then recrystallized to obtain 23.09 g (yield: 65%) of the product.

[0236] (3) Synthesis example of Sub2B-1-c

[0237] 2-Bromo-1,1'-biphenyl (23.3 g, 99.7 mmol) was dissolved in THF (270 mL) in a round-bottom flask under a nitrogen atmosphere and then cooled to -78 °C. Thereafter, n-BuLi (40 mL) was slowly added dropwise and stirred for 30 minutes. After that, Sub2B-1-b (23 g, 99.7 mmol) was dissolved in THF (140 mL), slowly titrated into the reaction round-bottom flask, stirred at -78 °C for 1 hour, and then slowly warmed to room temperature. After the reaction was completed, it was extracted with ethyl acetate and water, the organic layer was dried over MgSO4 and then concentrated. After that, the concentrate was separated by a silica gel column and then recrystallized to obtain 32.6 g (yield: 85%) of the product.

[0238] (4) Synthesis example of Sub2B-1

[0239] Sub2B-1-c (32 g, 84.7 mmol), acetic acid (208 mL) and concentrated hydrochloric acid (34.6 mL) were placed in a round-bottom flask, and then stirred at 60 - 80 °C under a nitrogen atmosphere for 3 hours. After the reaction was completed, it was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and then concentrated. After that, the concentrate was separated by a silica gel column and then recrystallized to obtain 27.7 g (yield: 91%) of the product.

[0240] 2. Synthesis example of Sub2B-11

[0241]

[0242] (1) Synthesis example of Sub2B-11-a

[0243] 2-Iodobenzoic acid (50.0 g, 202 mmol), benzenethiol (22.2 g, 202 mmol), potassium hydroxide (56.6 g, 1008 mmol), and copper powder (1.3 g, 20.2 mmol) were placed in a round-bottom flask. After adding water (1.3 L), the mixture was refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, and then HCl (3 M) was added until precipitation was complete. Thereafter, the precipitate was washed with water and dried to obtain 41.3 g of the product (yield: 89%).

[0244] (2) Synthesis example of Sub2B-11-b

[0245] Sub2B-11-a (41.3 g, 179 mmol) was placed in a round-bottom flask, and H2SO4 (1.3 mL) was added. The mixture was refluxed until all the starting materials were dissolved. When all the starting materials were dissolved, it was cooled to room temperature, and then ice water was added for precipitation. Thereafter, the precipitate was washed with water, dried, and dissolved in CH2Cl2. Thereafter, after separation by a silica gel column, recrystallization was carried out to obtain 25.9 g of the product (yield: 68%).

[0246] (3) Synthesis example of Sub2B-11-c

[0247] 2-Bromo-4'-chloro-1,1'-biphenyl (32.6 g, 122 mmol) was dissolved in THF in a round-bottom flask under a nitrogen atmosphere, and then cooled to -78 °C. Thereafter, n-BuLi (49 mL) was slowly added dropwise and stirred for 30 minutes. Thereafter, Sub2B-11-b (25.9 g, 122 mmol) was dissolved in THF, slowly titrated into the reaction round-bottom flask, stirred at -78 °C for 1 hour, and then slowly warmed to room temperature. After the reaction was completed, it was extracted with ethyl acetate and water, the organic layer was dried over MgSO4 and then concentrated. Thereafter, the concentrate was separated by a silica gel column and then recrystallized to obtain 40.1 g of the product (yield: 82%).

[0248] (4) Synthesis example of Sub2B-11

[0249] Sub2B-11-c (40.1 g, 100 mmol), acetic acid (250 mL), and concentrated hydrochloric acid (40 mL) were placed in a round-bottom flask, and then stirred at 60 - 80 °C for 3 hours under a nitrogen atmosphere. After the reaction was completed, it was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and then concentrated. Thereafter, the concentrate was separated by a silica gel column and then recrystallized to obtain 31.8 g of the product (yield: 83%).

[0250] The compound belonging to Sub2 can be a compound the same as the following compound, but is not limited thereto. The FD-MS values of the following compounds are shown in Table 2 respectively.

[0251]

[0252]

[0253]

[0254] [Table 2]

[0255]

[0256]

[0257] Synthesis Example of the Final Compound

[0258] Synthesis Example of 1.1 - 76

[0259]

[0260] After dissolving Sub2C - 46 (142.0 g, 418.6 mmol) in toluene (2,093 mL), Sub1A - 59 (129.5 g, 418.6 mmol), Pd2(dba)3 (11.5 g, 12.6 mmol), P(t - Bu)3 (5.1 g, 25.1 mmol) and NaOt - Bu (80.5 g, 837.2 mmol) were added, and the reaction was carried out at 100 °C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and then the resulting organic matter was separated by silica gel column and recrystallized to obtain 173.5 g of the product (yield: 73%).

[0261] Synthesis Example of 2.1 - 110

[0262]

[0263] After dissolving Sub2C - 33 (52.5 g, 212.6 mmol) in toluene (1,063 mL), Sub1A - 58 (87.5 g, 212.6 mmol), Pd2(dba)3 (5.8 g, 6.4 mmol), P(t - Bu)3 (2.6 g, 12.8 mmol) and NaOt - Bu (40.9 g, 425.2 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 1 - 76 above to obtain 92.1 g of the product (yield: 75%).

[0264] Synthesis Example of 3. P - 1

[0265]

[0266] Sub2B-1 (20 g, 54.5 mmol) was dissolved in toluene (400 mL), and then Sub1B-1 (18.3 g, 54.5 mmol), Pd2(dba)3 (1.5 g, 1.64 mmol), P(t-Bu)3 (50 wt% solution) (1.3 mL, 3.3 mmol) and NaOt-Bu (15.7 g, 163.6 mmol) were added, followed by stirring at 80 °C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Subsequently, the concentrate was separated by silica gel column chromatography and then purified by sublimation to obtain 29.8 g (yield: 82%) of the product.

[0267] 4. Synthesis Example of P-73

[0268]

[0269] Sub2B-27 (17 g, 38.4 mmol) was dissolved in anhydrous toluene (340 mL), and then Sub1B-88 (16.4 g, 38.4 mmol), Pd2(dba)3 (1.05 g, 1.15 mmol), NaOt-Bu (11.06 g, 115.14 mmol) and P(t-Bu)3 (50 wt% solution) (0.93 mL, 2.3 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above to obtain 20.4 g (yield: 80%) of the product.

[0270] 5. Synthesis Example of P1-2

[0271]

[0272] Sub2B-1 (15 g, 40.9 mmol) was dissolved in anhydrous toluene (300 mL), and then Sub1B-95 (16.0 g, 40.9 mmol), Pd2(dba)3 (1.12 g, 1.2 mmol), NaOt-Bu (11.8 g, 122.7 mmol) and P(t-Bu)3 (50 wt% solution) (1.00 mL, 2.5 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above to obtain 24.2 g (yield: 84%) of the product.

[0273] 6. Synthesis Example of P1-13

[0274]

[0275] After dissolving Sub2B-1 (10.2 g, 27.8 mmol) in anhydrous toluene (210 mL), Sub1A-12 (12.6 g, 27.8 mmol), Pd2(dba)3 (0.8 g, 0.76 mmol), NaOt-Bu (8.0 g, 83.4 mmol), and P(t-Bu)3 (50 wt% solution) (0.7 mL, 1.7 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above to obtain 17.6 g of the product (yield: 81%).

[0276] 7. Synthesis Example of P1-86

[0277]

[0278] After dissolving Sub2B-1 (33 g, 89.9 mmol) in anhydrous toluene (922 mL), Sub1C-18 (47.2 g, 94.5 mmol), Pd2(dba)3 (2.5 g, 2.7 mmol), NaOt-Bu (25.9 g, 269.8 mmol), and P(t-Bu)3 (50 wt% solution) (1.1 mL, 5.4 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above to obtain 63.5 g of the product (yield: 85.1%).

[0279] 8. Synthesis Example of P2-3

[0280]

[0281] After dissolving Sub2B-1 (9.5 g, 25.9 mmol) in anhydrous toluene (200 mL), Sub1D-3 (13.3 g, 25.9 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), NaOt-Bu (7.5 g, 77.7 mmol), and P(t-Bu)3 (50 wt% solution) (0.6 mL, 0.8 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above to obtain 18.1 g of the product (yield: 83%).

[0282] 9. Synthesis of P3-80

[0283]

[0284] After dissolving Sub1C-2 (10 g, 20.59 mmol) in toluene (211 mL), Sub2C-33 (5.34 g, 21.62 mmol), Pd2(dba)3 (0.57 g, 0.62 mmol), P(t-Bu)3 (0.33 g, 1.65 mmol) and NaOt-Bu (5.94 g, 61.78 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above, thereby obtaining 10.87 g of the product (yield: 81%).

[0285] 10. Synthesis of P3-88

[0286]

[0287] After dissolving Sub1C-28 (8.9 g, 16.93 mmol) in toluene (174 mL), Sub2C-27 (4.86 g, 17.78 mmol), Pd2(dba)3 (0.47 g, 0.51 mmol), P(t-Bu)3 (0.27 g, 1.35 mmol) and NaOt-Bu (4.88 g, 50.79 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of P-1 above, thereby obtaining 9.72 g of the product (yield: 80%).

[0288] The FD-MS value of the compound represented by Chemical Formula 1 of the present invention prepared according to the above synthesis method is as shown in Table 3 below.

[0289] [Table 3]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298] [Synthesis Example 2] Compound Represented by Chemical Formula 2

[0299] As shown in the following Reaction Scheme 2, the compound (end product 2) represented by Chemical Formula 2 according to the present invention can be prepared by the reaction of Sub3 and Sub4, but is not limited thereto. Sub3 below may be the same as Sub1 in Reaction Scheme 1. In addition, the compound (end product 2) represented by Chemical Formula 2 according to the present invention is prepared by the synthesis methods disclosed in Korean Patent No. 10-1614739 (authorized and announced on April 18, 2016) and Korean Patent Application No. 10-2016-0110817 (filed on August 30, 2016) of the applicant, but is not limited thereto.

[0300] <Reaction Scheme 4> (Hal 3 is Br or Cl.)

[0301]

[0302] Synthesis Example of Sub3

[0303] Sub3 in the above Reaction Scheme 3 can be synthesized through the reaction route of the following Reaction Scheme 5, but is not limited thereto.

[0304] <Reaction Scheme 5> (Hal 4 is Br or Cl.)

[0305]

[0306] In Reaction Scheme 5, A' and B' correspond to Ar 6 and Ar 7 and C' and D' correspond to L 6 and L 7 .

[0307] 1. Synthesis Example of Sub3-1

[0308]

[0309] Aniline (12.0 g, 128.24 mmol) was placed in a round-bottom flask, dissolved in toluene (400 mL), and then bromobenzene (20.1 g, 128.24 mmol), Pd2(dba)3 (5.9 g, 6.44 mmol), 50% P(t-Bu)3 (5.21 mL, 12.89 mmol) and NaOt-Bu (37.16 g, 386.64 mmol) were added, and the mixture was stirred at 100 °C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and then the resulting organic matter was separated by a silica gel column and recrystallized to obtain 17.01 g of the product (yield: 78%).

[0310] 2. Synthesis Example of Sub3-22

[0311]

[0312] Aniline (7.09 g, 76.18 mmol) was placed in a round-bottom flask, dissolved in toluene (500 mL), and then 4-bromo-N,N-diphenylaniline (24.7 g, 76.18 mmol), Pd2(dba)3 (3.49 g, 3.81 mmol), 50% P(t-Bu)3 (3.08 mL, 7.62 mmol), and NaOt-Bu (21.96 g, 228.55 mmol) were added. The reaction was carried out in the same manner as the synthesis method of Sub3-1 above to obtain 19.22 g of the product (yield: 75%).

[0313] 3. Synthesis Example of Sub3-46

[0314]

[0315] Aniline (5.72 g, 61.45 mmol) was placed in a round-bottom flask, dissolved in toluene (400 mL), and then 2-bromo-9-phenyl-9H-carbazole (19.80 g, 61.45 mmol), Pd2(dba)3 (2.81 g, 3.07 mmol), 50% P(t-Bu)3 (2.49 mL, 6.15 mmol), and NaOt-Bu (17.72 g, 184.35 mmol) were added. The reaction was carried out in the same manner as the synthesis method of Sub3-1 above to obtain 14.39 g of the product (yield: 70%).

[0316] 4. Synthesis Example of Sub3-57

[0317]

[0318] [1,1'-Biphenyl]-4-amine (13.86 g, 81.89 mmol) was placed in a round-bottom flask, dissolved in toluene (430 mL), and then 2-bromodibenzo[b,d]thiophene (21.55 g, 81.89 mmol), Pd2(dba)3 (3.75 g, 4.09 mmol), 50% P(t-Bu)3 (3.31 mL, 8.19 mmol), and NaOt-Bu (23.61 g, 245.68 mmol) were added. The reaction was carried out in the same manner as the synthesis method of Sub3-1 above to obtain 20.44 g of the product (yield: 71%).

[0319] 5. Synthesis Example of Sub3-69

[0320]

[0321] 4-(Dibenz[b,d]furan-2-yl)aniline (12.60 g, 48.58 mmol) was placed in a round-bottom flask, dissolved in toluene (330 mL), and then 2-(4-bromophenyl)dibenz[b,d]thiophene (16.48 g, 48.58 mmol), Pd2(dba)3 (2.22 g, 2.43 mmol), 50% P(t-Bu)3 (1.97 mL, 4.86 mmol), and NaOt-Bu (14.0 g, 145.73 mmol) were added. The reaction was carried out in the same manner as the synthesis method of Sub3-1 above to obtain 11.78 g of the product (yield: 69%).

[0322] The compound belonging to Sub3 may be the following compounds, but is not limited thereto. The FD-MS values of the following compounds are shown in Table 4 respectively.

[0323]

[0324]

[0325] [Table 4]

[0326]

[0327]

[0328] Synthesis Example of Sub4

[0329] Sub4 of the above Reaction Formula 4 can be synthesized through the reaction pathway of the following Reaction Formula 6, but is not limited thereto. The following Sub4' may be the same as Sub1 or Sub3 in Reaction Formula 1.

[0330] <Reaction Formula 6> (Hal 4 is I or Br, Hal 3 is Br or Cl.)

[0331]

[0332] 1. Synthesis Example of Sub4-1

[0333]

[0334] After dissolving Sub3-2 (20.16 g, 91.92 mmol) in toluene (965 ml), 4-bromo-4'-iodo-1,1'-biphenyl (33 g, 91.92 mmol), Pd2(dba)3 (1.26 g, 1.38 mmol), P(t-Bu)3 (0.56 g, 2.76 mmol) and NaOt-Bu (13.25 g, 137.88 mmol) were added, and the mixture was stirred at 70 °C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and then the resulting organic matter was separated by silica gel column and recrystallized to obtain 28.15 g of the product (yield: 68%).

[0335] 2. Synthesis Example of Sub4-14

[0336]

[0337] After dissolving Sub3-65 (24.48 g, 69.64 mmol) in toluene (731 ml), 2-bromo-6-iodonaphthalene (25 g, 69.64 mmol), Pd2(dba)3 (0.96 g, 1.04 mmol), P(t-Bu)3 (0.42 g, 2.09 mmol) and NaOt-Bu (10.04 g, 104.46 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 27.18 g of the product (yield: 67%).

[0338] 3. Synthesis Example of Sub4-30

[0339]

[0340] After dissolving Sub3-74 (20.73 g, 66.99 mmol) in toluene (703 ml), 3,3”-dibromo-1,1':2',1”-terphenyl (26 g, 66.99 mmol), Pd2(dba)3 (0.92 g, 1 mmol), P(t-Bu)3 (0.41 g, 2.01 mmol) and NaOt-Bu (9.66 g, 100.49 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 24.78 g of the product (yield: 60%).

[0341] 4. Synthesis Example of Sub4-36

[0342]

[0343] After dissolving Sub3-106 (31.12 g, 69.08 mmol) in toluene (725 ml), 2-bromo-6-iodonaphthalene (23 g, 69.08 mmol), Pd2(dba)3 (0.95 g, 1.04 mmol), P(t-Bu)3 (0.42 g, 2.07 mmol) and NaOt-Bu (9.96 g, 103.61 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 28.98 g of the product (yield: 64%).

[0344] 5. Synthesis example of Sub4-44

[0345]

[0346] After dissolving Sub3-55 (25.96 g, 79.76 mmol) in toluene (837 ml), 3,7-dibromodibenzo[b,d]furan (26 g, 79.76 mmol), Pd2(dba)3 (1.10 g, 1.20 mmol), P(t-Bu)3 (0.48 g, 2.39 mmol) and NaOt-Bu (11.5 g, 119.64 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 30.94 g of the product (yield: 68%).

[0347] 6. Synthesis example of Sub4-56

[0348]

[0349] After dissolving Sub3-25 (20.37 g, 60.72 mmol) in toluene (638 ml), 2-bromo-7-(4-bromophenyl)-9,9-dimethyl-9H-fluorene (26 g, 60.72 mmol), Pd2(dba)3 (0.83 g, 0.91 mmol), P(t-Bu)3 (0.37 g, 1.82 mmol) and NaOt-Bu (8.75 g, 91.09 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 25.70 g of the product (yield: 62%).

[0350] 7. Synthesis example of Sub4-82

[0351]

[0352] After dissolving N-([1,1'-biphenyl]-4-yl)-9-bromo-N-(9-chlorodibenzo[b,d]furan-2-yl)dibenzo[b,d]furan-2-amine (33 g, 53.7 mmol) in toluene (550 ml), Sub3-1 (9.5 g, 56.4 mmol), Pd2(dba)3 (1.5 g, 1.6 mmol), P(t-Bu)3 (0.7 g, 3.2 mmol) and NaOt-Bu (15.5 g, 161 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of Sub4-1 above to obtain 33 g of the product (yield: 82.4%).

[0353] The compound belonging to Sub4 may be the following compounds, but is not limited thereto. The FD-MS values of the following compounds are shown in Table 5 respectively.

[0354]

[0355]

[0356]

[0357] [Table 5]

[0358]

[0359]

[0360] Synthesis Example of the Final Compound

[0361] Synthesis example of 1.2-1

[0362]

[0363] After dissolving Sub4-1 (10 g, 22.20 mmol) in toluene (233 ml), Sub3-2 (5.36 g, 24.42 mmol), Pd2(dba)3 (0.61 g, 0.67 mmol), P(t-Bu)3 (0.45 g, 2.22 mmol) and NaOt-Bu (6.40 g, 66.61 mmol) were added, and the mixture was stirred at 100 °C. After the reaction was completed, it was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and then the resulting organic matter was separated by a silica gel column and recrystallized to obtain 10.46 g of the product (yield: 80%).

[0364] Synthesis example of 2.2-10

[0365]

[0366] After dissolving Sub4-1 (8 g, 17.76 mmol) in toluene (187 ml), Sub3-35 (8.98 g, 19.54 mmol), Pd2(dba)3 (0.49 g, 0.53 mmol), P(t-Bu)3 (0.36 g, 1.78 mmol) and NaOt-Bu (5.12 g, 53.29 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 10.6 g of the product (yield: 72%).

[0367] Synthesis Example of 3.2-23

[0368]

[0369] After dissolving Sub4-20 (9 g, 15.91 mmol) in toluene (167 ml), Sub3-47 (5.85 g, 17.51 mmol), Pd2(dba)3 (0.44 g, 0.48 mmol), P(t-Bu)3 (0.32 g, 1.59 mmol) and NaOt-Bu (4.59 g, 47.74 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 10.04 g of the product (yield: 77%).

[0370] Synthesis Example of 4.2-50

[0371]

[0372] After dissolving Sub4-45 (9.5 g, 19.77 mmol) in toluene (208 ml), Sub3-11 (6.99 g, 21.75 mmol), Pd2(dba)3 (0.54 g, 0.59 mmol), P(t-Bu)3 (0.40 g, 1.98 mmol) and NaOt-Bu (5.70 g, 59.32 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 10.41 g of the product (yield: 73%).

[0373] Synthesis Example of 5.2-114

[0374]

[0375] After dissolving Sub4-68 (6.13 g, 13.20 mmol) in toluene (130 ml), Sub3-74 (4.08 g, 13.20 mmol), Pd2(dba)3 (0.36 g, 0.40 mmol), P(t-Bu)3 (0.27 g, 1.32 mmol) and NaOt-Bu (3.81 g, 39.60 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 7.32 g of the product (yield: 80%).

[0376] Synthesis Example of 6.2-128

[0377]

[0378] After dissolving Sub4-88 (22 g, 29 mmol) in toluene (297 ml), Sub3-1 (5.2 g, 30.5 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P(t-Bu)3 (0.4 g, 1.7 mmol) and NaOt-Bu (8.4 g, 87 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 19.2 g of the product (yield: 78.3%).

[0379] Synthesis Example of 7.P4-23

[0380]

[0381] After dissolving Sub4-75 (26 g, 34.8 mmol) in toluene (256 ml), Sub3-1 (6.2 g, 36.5 mmol), Pd2(dba)3 (0.96 g, 1.0 mmol), P(t-Bu)3 (0.4 g, 2.1 mmol) and NaOt-Bu (10 g, 104.3 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 24.2 g of the product (yield: 83.1%).

[0382] Synthesis Example of 8.P4-25

[0383]

[0384] After dissolving Sub4-77 (19 g, 25.4 mmol) in toluene (260 ml), Sub3-1 (4.5 g, 26.7 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol) and NaOt-Bu (7.3 g, 76.2 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 16 g of the product (yield: 75.4%).

[0385] 9. Synthesis Example of P4-146

[0386]

[0387] After dissolving Sub4-82 (23 g, 30.8 mmol) in toluene (315 ml), Sub3-1 (5.5 g, 32.3 mmol), Pd2(dba)3 (0.9 g, 0.9 mmol), P(t-Bu)3 (0.4 g, 1.9 mmol) and NaOt-Bu (8.9 g, 92.3 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 20.6 g of the product (yield: 80%).

[0388] 10. Synthesis Example of P4-150

[0389]

[0390] After dissolving Sub4-86 (24 g, 31 mmol) in toluene (318 ml), Sub3-1 (5.5 g, 32.6 mmol), Pd2(dba)3 (0.9 g, 0.9 mmol), P(t-Bu)3 (0.4 g, 1.9 mmol) and NaOt-Bu (8.9 g, 93.1 mmol) were added, and the reaction was carried out in the same manner as the synthesis method of 2-1 above, thereby obtaining 20.7 g of the product (yield: 77.3%). The FD-MS value of the compound represented by Chemical Formula 2 of the present invention prepared according to the above synthesis method is as shown in Table 6 below.

[0391] [Table 6]

[0392]

[0393]

[0394]

[0395] Next, for the method of measuring the HOMO energy level using the compound of the present invention prepared according to the synthesis example described above, examples will be given for specific illustration, but the present invention is not limited to the following examples.

[0396] Example for Measuring HOMO Energy Level

[0397] The HOMO energy level can be measured using a CV-chart.

[0398] Prepare a measurement sample in which an electrolyte and the compound to be measured are dissolved. Exemplarily, prepare a 0.1 M TBAP in ACN (acetonitrile) electrolyte, and dissolve 2.5 mg of the compound to be measured in 1 ml of chloroform as the solvent to prepare the measurement sample.

[0399] After that, at room temperature, measure the cyclic voltage-current (cyclic voltammetry) of the above measurement sample, and the HOMO energy level can be obtained using a CV-chart (current-voltage chart). The vertical axis of the CV-chart represents current, and the horizontal axis represents voltage (potential). The HOMO energy level is obtained using the lower curve in the two curves. That is, using the chart when scanning the voltage in the reverse direction, the HOMO energy level can be obtained from the potential value at the intersection of the two straight lines. That is, simply change the unit of the potential value to eV as the energy unit.

[0400] The above two straight lines mean the tangent line (horizontal line) drawn for the chart in the interval before the start of a meaningful reaction (interval with almost no current change), and the tangent line drawn for the curve between the start of a meaningful reaction and the location where the maximum oxidation current flows (interval where the current rapidly decreases as the voltage increases).

[0401] In addition, in order to obtain the HOMO energy level of the compound to be measured, it is necessary to correct it with the HOMO energy level of a reference sample. That is, like the following conversion formula, apply the correction value, which is the difference in CV values between the reference sample and the measurement sample, to the HOMO energy level inherent in the reference sample to calculate the HOMO energy level of the compound to be measured.

[0402] Conversion Formula:

[0403] HOMO energy level of the compound to be measured = HOMO energy level inherent in the reference sample + correction value

[0404] In the above conversion formula, the correction value is obtained using the following formula.

[0405] Correction value = (HOMO energy level in the CV-chart of the reference sample) - (HOMO level in the CV-chart of the measurement sample)

[0406] For example, when Alq3 is used as a reference sample, the HOMO energy level of the compound to be measured can be obtained by means of the following conversion formula. The inherent HOMO energy level of Alq3 is -5.8 eV.

[0407] HOMO energy level of the compound to be measured = -5.8 (eV) + correction value

[0408] [Correction value = (HOMO energy level in the CV-chart of Alq3) - (HOMO energy level in the CV-chart of the sample to be measured)]

[0409] The HOMO energy levels of the compounds of the present invention measured according to the energy level measurement method described above are shown in Table 7 below.

[0410] [Table 7]

[0411]

[0412] Hereinafter, examples will be given for the manufacture and evaluation of an organic electrical element using the compound of the present invention, but the present invention is not limited to the following examples.

[0413] Manufacturing Evaluation of Organic Electrical Components

[0414] [Example 1] Green organic electroluminescent element (luminescence assisting layer)

[0415] After forming a 60 nm-thick hole injection layer by vacuum depositing a 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter, simply referred to as "2-TNATA") film on an ITO layer (anode) formed on a glass substrate, a 60 nm-thick N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter simply referred to as "NPB") film was vacuum deposited on the hole injection layer to form a hole transport layer.

[0416] Next, a luminescence assisting layer was formed. The above luminescence assisting layer includes a first luminescence assisting layer formed by vacuum depositing Compound 1-3 of the present invention with a thickness of 30 nm on the above hole transport layer, and a second luminescence assisting layer formed by vacuum depositing Compound 1-16 of the present invention with a thickness of 5 nm. At this time, in the first luminescence assisting layer and the second luminescence assisting layer, it is preferred to preferentially deposit the substance with a higher HOMO energy level.

[0417] After that, on the luminescence assisting layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter simply referred to as "CBP") was used as a host, tris(2-phenylpyridine)iridium (hereinafter simply referred to as "Ir(ppy)3") was used as a doping substance, and doping was carried out at a weight ratio of 95:5, and a luminescence layer was vacuum deposited with a thickness of 30 nm.

[0418] Then, tris(8-hydroxyquinolinato)aluminum bis(2-methyl-8-hydroxyquinolinato) (hereinafter simply referred to as "BAlq") was vacuum deposited on the above-mentioned light-emitting layer with a thickness of 10 nm to form a hole-blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter simply referred to as "BeBq2") was vacuum deposited on the above-mentioned hole-blocking layer with a thickness of 50 nm to form an electron-transporting layer.

[0419] Then, LiF was deposited on the above-mentioned electron-transporting layer with a thickness of 0.2 nm, and then Al was deposited with a thickness of 150 nm to form a cathode, thereby fabricating an organic electroluminescent element.

[0420] [Example 2] to [Example 24]

[0421] An organic electroluminescent element was fabricated in the same manner as in Example 1 above, except that the compounds shown in Table 8 below were used as the materials for the first light-emitting auxiliary layer and the second light-emitting auxiliary layer.

[0422] [Comparative Example 1]

[0423] The following Comparative Compound 1 and 2 were mixed at a weight ratio of 98:2 and vacuum deposited with a thickness of 10 nm to form a first light-emitting auxiliary layer. Thereafter, an organic electroluminescent element was prepared in the same manner as in Example 1, except that Comparative Compound 1 was vacuum deposited with a thickness of 40 nm on the first light-emitting auxiliary layer to form a second light-emitting auxiliary layer.

[0424] [Comparative Example 2]

[0425] Compound 1-13 and the following Comparative Compound 2 were mixed at a weight ratio of 98:2 and vacuum deposited with a thickness of 5 nm to form a first light-emitting auxiliary layer. Thereafter, an organic electroluminescent element was prepared in the same manner as in Example 1, except that Compound 1-16 was vacuum deposited with a thickness of 30 nm on the first light-emitting auxiliary layer to form a second light-emitting auxiliary layer.

[0426]

[0427] [Comparative Example 3] to [Comparative Example 8]

[0428] As described in Table 8 below, an organic electroluminescent element was prepared in the same manner as in Example 1 above, except that a single compound was vacuum deposited with a thickness of 35 nm to form one light-emitting auxiliary layer without additional doping.

[0429] A forward bias DC voltage was applied to the organic electroluminescent elements prepared according to Examples 1 to 24 and Comparative Examples 1 to 8 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research Corporation. At a reference brightness of 5000 cd / m 2 The T95 lifetime was measured using a lifetime measurement device manufactured by MC Science Corporation, Korea. The measurement results are shown in Table 8 below.

[0430] [Table 8]

[0431]

[0432]

[0433] From the results in Table 8 above, it can be seen that when the materials for the organic electroluminescent elements of the present invention are used as materials for multiple light-emitting auxiliary layers to prepare green organic light-emitting elements, the driving voltage, efficiency, and lifetime are all improved compared to the comparative examples.

[0434] Regarding Comparative Examples 1 and 2, they are similar to the present invention in that two light-emitting auxiliary layers are formed, but the difference from the present invention is that the first light-emitting auxiliary layer is formed with Comparative Compound 1 or Comparative Compound 2 in which Compound 1-13 of the present invention is mixed as a p-type doping substance.

[0435] Comparative Examples 1 and 2 have differences in the formation materials of the light-emitting auxiliary layer and the thickness of the light-emitting auxiliary layer. It can be seen that in Comparative Example 2 where the total thickness of the light-emitting auxiliary layer and the thickness of each light-emitting auxiliary layer are thinner, the driving voltage, efficiency, and lifetime of the element are more improved compared to Comparative Example 1.

[0436] Moreover, compared to the element characteristics of Comparative Examples 1 and 2 prepared by mixing Comparative Compound 2 as a p-type doping substance, in Comparative Examples 3 to 8 where a single-layer light-emitting auxiliary layer is formed with one compound without using a p-type doping substance, the driving voltage and efficiency of the element are improved.

[0437] Moreover, it can be confirmed that compared to Comparative Examples 3 to 8, the driving voltage, efficiency, and lifetime of the elements of Examples 1 to 24 of the present invention are significantly improved. Regarding Examples 1 to 24 of the present invention above, multiple light-emitting auxiliary layers are formed such that the HOMO energy level is higher than that of the hole transport layer and lower than that of the light-emitting layer, and two light-emitting auxiliary layers are formed so that the HOMO energy level of the first light-emitting auxiliary layer is higher than that of the second light-emitting auxiliary layer.

[0438] This is because a compound with a high hole mobility and excellent hole injection characteristics is used as the first light-emitting auxiliary layer material, and a compound with excellent electron-blocking characteristics is used as the second light-emitting auxiliary layer material to form multiple light-emitting auxiliary layers, so that even without using a p-type doping material, the injection / flow characteristics of holes and electrons can be improved, and the charge balance in the light-emitting layer is increased.

[0439] [Examples 25] to [Examples 48] Red Organic Electroluminescent Element (Light-Emitting Auxiliary Layer)

[0440] An organic electroluminescent element was fabricated in the same manner as in Example 1 above, except that the compounds described in Table 9 below were used as the first light-emitting auxiliary layer material and the second light-emitting auxiliary layer material, and bis(1-phenylisoquinolinato)acetylacetonatoiridium(III) (hereinafter, simply referred to as "(piq)2Ir(acac)") was used as the dopant.

[0441] [Comparative Example 9]

[0442] An organic electroluminescent element was fabricated in the same manner as in Comparative Example 1 above, except that bis(1-phenylisoquinolinato)acetylacetonatoiridium(III) (hereinafter, simply referred to as "(piq)2Ir(acac)") was used as the dopant.

[0443] [Comparative Example 10]

[0444] An organic electroluminescent element was fabricated in the same manner as in Comparative Example 2 above, except that a mixture of Compound 1-9 of the present invention and Comparative Compound 2 at a weight ratio of 98:2 was used as the first light-emitting auxiliary layer material, Compound 1-5 of the present invention was used as the second light-emitting auxiliary layer material, and bis(1-phenylisoquinolinato)acetylacetonatoiridium(III) (hereinafter, simply referred to as "(piq)2Ir(acac)") was used as the dopant.

[0445] [Comparative Examples 11] to [Comparative Examples 16]

[0446] An organic electroluminescent element was fabricated in the same manner as in Comparative Example 3 above, except that the compounds described in Table 9 below were used as the light-emitting auxiliary layer material, and bis(1-phenylisoquinolinato)acetylacetonatoiridium(III) (hereinafter, simply referred to as "(piq)2Ir(acac)") was used as the dopant.

[0447] A forward bias DC voltage was applied to the organic electroluminescent elements prepared in Examples 25 to 48 and Comparative Examples 9 to 16 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. At 2500 cd / m 2At the reference brightness, the T95 lifetime was measured using a lifetime measurement device manufactured by MC Science Corporation of Korea. The measurement results are shown in Table 9 below.

[0448] [Table 9]

[0449]

[0450]

[0451] As can be seen from Table 9 above, Comparative Examples 11 and 12 are similar to the present invention in that two light-emitting auxiliary layers are formed, but the difference from the present invention is that Comparative Compound 2 in which Comparative Compound 1 or Compound 1-9 of the present invention is mixed as a p-type doping substance is used to form the first light-emitting auxiliary layer. The difference between Comparative Examples 11 to 16 and the present invention is that a single light-emitting auxiliary layer is formed of one compound.

[0452] Looking at Comparative Examples 9 to 16, the device characteristics of Comparative Examples 11 to 16 in which the light-emitting auxiliary layer is formed as a single layer are more excellent than those of Comparative Examples 9 and 10 in which two light-emitting auxiliary layers are formed. In particular, although Comparative Examples 10 and 11 are the same in that they include a light-emitting auxiliary layer formed of Compound 1-5, the characteristics of the device are slightly improved in Comparative Example 11 having a single light-emitting auxiliary layer.

[0453] However, even when multiple light-emitting auxiliary layers are formed, in Embodiments 25 to 48 of the present invention, the device characteristics are significantly improved. From such results, it can be confirmed that by selectively using compounds having a HOMO energy level correlation according to the conditions defined in the present invention, the device characteristics can be improved when multiple light-emitting auxiliary layers are formed with different thicknesses.

[0454] For the present invention, the reason for the improvement of the device characteristics is that compounds having mutually different HOMO energy levels between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer of the organic electroluminescent device are used as the light-emitting auxiliary layer material, and the thickness is adjusted to form the first light-emitting auxiliary layer and the second light-emitting auxiliary layer, thereby improving the injection of electrons and holes into the light-emitting layer and the charge balance in the light-emitting layer.

[0455] The above description is only illustrative, and those of ordinary skill in the art to which the present invention pertains can make various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are not used to limit the present invention, but to illustrate the present invention, and the idea and scope of the present invention will not be limited by such embodiments. The protection scope of the present invention should be interpreted according to the scope of the invention claimed, and all technologies within the equivalent scope should be interpreted as being included in the protection scope of the present invention.

[0456] Cross-Reference to Related Patent Applications

[0457] This patent application claims priority under Sections 119 to 121 and 365 of the United States Patent Law (35 U.S.C. §§ 119 to 121, § 365) with respect to Patent Application No. 10-2019-0138801 filed in Korea on November 01, 2019 and Patent Application No. 10-2020-0138278 filed in Korea on October 23, 2020, the entire contents of which are incorporated herein by reference. In addition, if this patent application claims priority for the same reason in other countries in addition to the United States, the entire contents thereof are incorporated herein by reference.

Claims

1. An organic electrical component, the organic electrical component including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein, the organic layer includes: a light-emitting layer; a hole transport layer formed between the first electrode and the light-emitting layer; and a plurality of light-emitting auxiliary layers formed between the light-emitting layer and the hole transport layer, the light-emitting auxiliary layer includes: a first light-emitting auxiliary layer adjacent to the hole transport layer; a second light-emitting auxiliary layer adjacent to the light-emitting layer, the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are respectively without additional doping and are formed of a single compound, the HOMO energy level of the light-emitting auxiliary layer is lower than the HOMO energy level of the hole transport layer and higher than the HOMO energy level of the light-emitting layer, the HOMO energy level of the first light-emitting auxiliary layer is higher than the HOMO energy level of the second light-emitting auxiliary layer, the first light-emitting auxiliary layer and the second light-emitting auxiliary layer contain a compound represented by the following Chemical Formula 1 or a compound represented by the following Chemical Formula 2: In the above Chemical Formula 1 and 2, Ar 1 to Ar 7 are each independently selected from the group consisting of aryl having 6 to 60 carbon atoms; fluorenyl; heterocyclic group having 2 to 60 carbon atoms and containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and aliphatic cyclic group having 3 to 60 carbon atoms, and Ar 4 and Ar 5 may combine with each other to form a ring, and Ar 6 and Ar 7 may combine with each other to form a ring. L 1 to L 7 each independently selected from the group consisting of a single bond; a C6-C 60 arylene group; a fluorene group; a C3-C 60 alicyclic group; and a C2-C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, L 8 is selected from the group consisting of arylene having 6 to C 60 ; fluorenylene; aliphatic cyclic group having 3 to C 60 ; and heterocyclic group having 2 to C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 ; The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic group, aliphatic cyclic group, Ar 4 and Ar 5 The rings formed by bonding with each other, and Ar 6 and Ar 7 The rings formed by bonding with each other can each optionally be selected from the group consisting of deuterium, halogen, a C1-C 20 alkyl or C6-C 20 aryl-substituted or unsubstituted silyl, siloxanyl, cyano, nitro, C1-C 20 alkylthio group, C1-C 20 alkoxy group, C6-C 20 aryloxy group, C6-C 20 arylthio group, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, a C2-C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ) and further substituted by one or more substituents selected from the group consisting of The above L’ is selected from the group consisting of a single bond; an arylene group having 6 to 20 carbon atoms; a fluorene group; an alicyclic group having 3 to 20 carbon atoms; and a heterocyclic group having 2 to 20 carbon atoms and containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, The above-mentioned R a and R b are each independently selected from the group consisting of aryl having 6 to C 20 ; fluorenyl; aliphatic cyclic group having 3 to C 20 ; and heterocyclic group having 2 to C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 .

2. The organic electrical component according to claim 1, wherein, The thickness of the first light-emitting auxiliary layer is 200 to The thickness of the second light-emitting auxiliary layer is 50 to The total thickness of the plurality of light-emitting auxiliary layers is 300 to 3. The organic electrical component according to claim 1, wherein, the HOMO energy level of the first light-emitting auxiliary layer is 0.01 to 0.5 eV higher than the HOMO energy level of the second light-emitting auxiliary layer.

4. The organic electrical component according to claim 1, wherein, The HOMO energy levels of the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are respectively 5.50 to 5.69 eV based on absolute value.

5. The organic electrical component according to claim 1, wherein, The Chemical Formula 1 is represented by the following Chemical Formula A-1 or Chemical Formula A-2, In the above chemical formulas A-1 and A-2, L 1 to L 3 , Ar 2 , Ar 3 are the same as defined in claim 1, Y1 and Y2 are a single bond, O, S or C(R5)(R6), and the case where both Y1 and Y2 are single bonds is excluded, R1 to R6, Z1, and Z2 are independently selected from the group consisting of deuterium, halogen, C1-C 20 alkyl or C6-C 20 aryl-substituted or unsubstituted silyl, siloxanyl, cyano, nitro, C1-C 20 alkylthio, C1-C 20 alkoxy, C6-C 20 aryloxy, C6-C 20 arylthio, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic ring, and -L'-N(R a )(R b ), and adjacent groups may combine with each other to form a ring, R5 and R6 may combine with each other to form a ring, and Z1 and Z2 may combine with each other to form a ring. a, c and d are respectively integers from 0 to 4, b is an integer from 0 to 3, and when these are integers of 2 or more, R1 respectively, R2 respectively, R3 respectively, R4 respectively are the same or different, The aryl, fluorenyl, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, the ring formed by the combination of adjacent groups with each other, the ring formed by the combination of R5 and R6 with each other, and the ring formed by the combination of Z1 and Z2 with each other can each optionally be selected from the group consisting of deuterium, halogen, cyano group, nitro group, C1-C 20 alkoxy groups of 20 aryloxy groups of C6-C 20 alkyl groups of C1-C 20 alkenyl groups of C2-C 20 alkynyl groups of C2-C 20 aryl groups of C6-C 20 heterocyclic groups of C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 aliphatic cyclic groups of C3-C a and -L'-N(R b )(R ) and further substituted by one or more substituents selected from the group consisting of L', R a and R b are the same as defined in claim 1.

6. The organic electrical component according to claim 5, wherein, the Chemical Formula A-1 is represented by the following Chemical Formula A-3 or Chemical Formula A-4, In the above Chemical Formula A-1 or Chemical Formula A-4, R 1' and R 2' are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C1-C 20 alkoxy, C6-C 20 aryloxy, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ), m is an integer from 0 to 4, n is an integer from 0 to 3, and when these are integers of 2 or more respectively, R 1‘ respectively, R 2‘ are the same or different respectively, L 1 to L 3 、Ar 2 、Ar 3 、R1, R2, a, b, L', R a and R b are the same as defined in claim 5.

7. The organic electrical component according to claim 5, wherein, the Chemical Formula A-1 is represented by the following Chemical Formula A-5 or Chemical Formula A-6, In the above chemical formulas A-5 and A-6, Y1, L 1 to L 3 , Ar 3 are the same as defined in claim 5.

8. The organic electrical component according to claim 1, wherein, the Chemical Formula 2 is represented by the following Chemical Formula B-1, <Chemical Formula B-1> In the above chemical formula B-1, L 4 to L 7 、Ar 4 、Ar 5 、Ar 7 have the same definition as that in claim 1, Ring A, Ring B, Ring C, and Ring D are each independently selected from the group consisting of C6-C 20 aromatic rings, fluorenyl groups, C2-C 20 heterocyclic groups containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and C3-C 20 aliphatic cyclic groups, and these can each be further substituted by one or more Rs X1 and X2 are independently O, S, N(Ar) or C(R7)(R8), L a to L e are each independently selected from the group consisting of a single bond; a C6-C 20 arylene; a fluorene group; a C2-C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a C3-C 20 alicyclic group Ar d 、 Ar e and, independently of each other, the above-mentioned Ar, are each selected from the group consisting of aryl groups having 6 to C 20 ; fluorenyl groups; heterocyclic groups having 2 to C 20 and containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and aliphatic cyclic groups having 3 to C 20 . R, R7 and R8 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C1-C 20 alkoxy, C6-C 20 aryloxy, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic group, and C3-C 20 alicyclic group, and R7 and R8 may combine with each other to form a ring, The aryl, arylene, fluorenyl, fluorenylene, heterocyclic group, aliphatic cyclic group, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and the ring formed by the combination of R7 and R8 can each optionally be selected from the group consisting of deuterium, halogen, cyano, nitro, C1-C 20 alkoxy, C6-C 20 aryloxy, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ) and further substituted by one or more substituents in the group consisting of L', R a and R b are the same as defined in claim 1.

9. The organic electrical component according to claim 8, wherein, the Chemical Formula B-1 is represented by the following Chemical Formula B-2, <Chemical Formula B-2> In the above chemical formula B-2, Ar 4 、Ar 5 、Ar 7 、Ar d 、Ar e 、X1, and X2 are the same as defined in claim 8.

10. The organic electrical component according to claim 8, wherein, the Chemical Formula B-1 is represented by one of the following Chemical Formulas B-3 to B-6, In the above chemical formulas B-3 to B-6, Ar 4 , Ar 5 , Ar 7 , Ar d , Ar e , X1, and X2 are the same as defined in claim 8.

11. The organic electrical component according to claim 1, wherein, the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are formed of different compounds from each other.

12. The organic electrical component according to claim 5, wherein, The first light-emitting auxiliary layer contains a compound represented by Chemical Formula A-1.

13. The organic electrical component according to claim 1, wherein, The compound represented by the above Chemical Formula 1 is one of the following compounds:

14. The organic electrical component according to claim 1, wherein, The compound represented by the above Chemical Formula 2 is one of the following compounds:

15. The organic electrical component according to claim 1, wherein, When the first light-emitting auxiliary layer is composed of the compound represented by the above Chemical Formula 1 or Chemical Formula 2, at least one of the above Ar 1 to Ar 7 and L 8 is represented by the following Chemical Formula 3: <Chemical Formula 3> In Chemical Formula 3, * represents the bonding position, X is N, N-(L a -Ar a ), O, S or C(R')(R”), R 1 、R 2 、R', and R" are independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C1-C 20 alkylthio, C1-C 20 alkoxy, C6-C 20 aryloxy, C6-C 20 arylthio, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group, C3-C 20 aliphatic cyclic group, and -L'-N(R a )(R b ), and adjacent groups can combine with each other to form a ring, and R' and R" can combine with each other to form a ring. a and b are integers from 0 to 4 respectively, and when these are integers of 2 or more, R 1 respectively, R 2 are the same or different respectively The above-mentioned L a is selected from the group consisting of a single bond; a C6-C 20 arylene group; a fluorenylene group; a C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 heterocyclic group; and a C3-C 20 alicyclic group, The above-mentioned Ar a is selected from the group consisting of aryl having 6 to C 20 ; fluorenyl; C2-C having at least one heteroatom selected from the group consisting of O, N, S, Si, and P 20 ; heterocyclic group; and C3-C 20 aliphatic cyclic group The above-mentioned L' and R a and R b are the same as the definition in Claim 1.

16. The organic electrical component according to claim 1, wherein, When the second light-emitting auxiliary layer is composed of the compound represented by the above Chemical Formula 1 or Chemical Formula 2, the above Ar 1 to Ar 7 is an aryl group having 6 to 24 carbon atoms, and L 8 is an arylene group having 6 to 24 carbon atoms.

17. The organic electrical component according to claim 1, wherein, the light-emitting layer is a red light-emitting layer or a green light-emitting layer.

18. The organic electrical component according to claim 1, wherein, It further includes a light efficiency improvement layer formed on one side of the first electrode and the second electrode that is not in contact with the organic layer.

19. The organic electrical component according to claim 1, wherein, The above-mentioned organic layer includes two or more stacks, which include a hole transport layer, a light-emitting layer, and an electron transport layer formed in sequence on the above-mentioned first electrode.

20. The organic electrical component according to claim 19, wherein The above-mentioned organic layer further includes a charge generation layer formed between the two or more stacks.

21. An electronic device, wherein, Comprising: A display device, including the organic electrical component according to claim 1; And A control unit for driving the above-mentioned display device.

22. The electronic device according to claim 21, wherein, The above-mentioned organic electrical component is selected from the group consisting of: an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, or an element for a quantum dot display.

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