Organic electronic components and electronic devices containing compounds for use in organic electronic components

Abstract

Provided are an organic electronic element including an anode, a cathode, and an organic material layer between the anode and the cathode, and an electronic device including the organic electronic element, wherein the organic material layer respectively contains a compound represented by Formula 1 and Formula 2, and thus is capable of reducing a driving voltage of the organic electronic element and improving brightness and a service life of the organic electronic element.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic components, organic electronic components using said compounds, and electronic devices thereof. Background Technology

[0002] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electronic components utilizing organic light emission generally have a structure comprising an anode, a cathode, and layers of organic material interposed therebetween. To increase the efficiency and stability of the organic electronic components, the organic material layers are typically composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

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

[0004] Lifespan and efficiency are the biggest challenges for organic electroluminescent devices, and these issues must be addressed as displays become larger. Efficiency, lifespan, and driving voltage are interrelated, and as efficiency increases, the driving voltage relatively decreases. Conversely, as the driving voltage decreases, the lifespan tends to increase due to reduced crystallization of the organic material caused by Joule heating during driving.

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

[0006] Furthermore, in order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, a light-emitting auxiliary layer must exist between the hole transport layer and the light-emitting layer, and different light-emitting auxiliary layers should be developed according to each type of light-emitting layer (R, G, B).

[0007] Typically, electrons transfer from the electron transport layer to the luminescent layer, and holes transfer from the hole transport layer to the luminescent layer, and excitons are generated through recombination.

[0008] However, since the materials used for the hole transport layer should have low HOMO values, most have low T1 values. As a result, excitons generated in the luminescent layer are transferred to the hole transport layer, causing a charge imbalance in the luminescent layer, which in turn leads to luminescence at the hole transport layer interface.

[0009] When light is emitted at the hole transport layer interface, the color purity and efficiency of organic electronic components decrease, and their lifespan is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer with a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0010] Furthermore, there is a need to develop hole injection layer materials that delay the penetration and diffusion of metal oxides from the inductively coupled oxide (ITO) electrode into the organic layer (one of the reasons for the shortened lifespan of organic electronic devices) and possess stable properties, namely, a high glass transition temperature, and even resistance to Joule heating generated during device operation. The low glass transition temperature of hole transport layer materials has the property of reducing the uniformity of the film surface during device operation, which has been reported to have a significant impact on device lifespan. In addition, OLED devices are mainly formed by deposition methods, and there is a need to develop materials that can withstand long-term deposition, i.e., materials with strong heat resistance.

[0011] In other words, to fully realize the superior characteristics of organic electronic components, priority should be given to materials that are stable and effective in constituting the organic material layers in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials. However, the development of stable and effective organic material layer materials for organic electronic devices has not yet been fully realized. Therefore, it is necessary to continuously develop new materials.

[0012] KR 1020130076842 A is the prior art document used for reference. Summary of the Invention

[0013] The purpose of this invention is to provide organic electronic components and electronic devices thereof that contain compounds that can reduce the driving voltage of the components and improve the luminous efficiency, color purity, stability and lifespan of the components.

[0014] Technical solution

[0015] In one aspect, the present invention provides an organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a light-emitting layer and a hole transport band formed between the light-emitting layer and the anode, wherein the hole transport band comprises a compound represented by Formula 1, and the light-emitting layer comprises an organic electronic element comprising a compound represented by Formula 2.

[0016]

[0017] In another aspect, the present invention provides an electronic device including the organic electrical element.

[0018] Invention Effects

[0019] By using the compounds according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the element can be achieved, and the color purity and lifespan of the element can be significantly improved. Attached Figure Description

[0020] Figures 1 to 3 This is an exemplary view of an organic electroluminescent device according to the present invention.

[0021] 100, 200, 300: Organic electronic components; 110: First electrode

[0022] 120: Hole injection layer; 130: Hole transport layer

[0023] 140: Emissive layer; 150: Electron transport layer

[0024] 160: Electron injection layer; 170: Second electrode

[0025] 180: Light efficiency enhancement layer; 210: Buffer layer

[0026] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0027] 330: First hole transport layer; 340: First luminescent layer

[0028] 350: First electron transport layer; 360: First charge generation layer

[0029] 361: Second charge generation layer; 420: Second hole injection layer

[0030] 430: Second hole transport layer; 440: Second luminescent layer

[0031] 450: Second electron transport layer; CGL: Charge generation layer

[0032] ST1: First stack; ST2: Second stack Detailed Implementation

[0033] Some embodiments of the invention will be described in detail below. Furthermore, in the following description of the invention, detailed descriptions of known functions and configurations incorporated herein will be omitted where such inclusion would make the subject matter of the invention considerably unclear.

[0034] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b) may be used herein. Each of these terms is not intended to define the substance, order, or sequence of the respective component, but only to distinguish the respective component from other components. It should be noted that if a component is described as “connected,” “linked,” or “attached” to another component, the component may be directly connected to or connected to other components, but may be “connected,” “linked,” or “attached” between components.

[0035] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0036] Unless otherwise stated, the term "halogenated" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0037] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein means having a single bond of 1 to 60 carbon atoms and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), alkyl-substituted cycloalkyl groups, or cycloalkyl-substituted alkyl groups.

[0038] Unless otherwise stated, the terms “alkenyl” or “alkynyl” as used herein have, but are not limited to, two to 60 carbon atoms in double or triple bonds, and include straight or branched groups.

[0039] Unless otherwise stated, the term "cycloalkyl" as used herein means, but is not limited to, an alkyl group that forms a ring having 3 to 60 carbon atoms.

[0040] Unless otherwise stated, the terms “alkoxy,” “alkoxy group,” or “alkyloxy” as used herein mean, but are not limited to, an oxygen group attached to an alkyl group having 1 to 60 carbon atoms.

[0041] Unless otherwise stated, the terms “aryloxy group” or “aryloxy group” as used herein mean, but are not limited to, an oxygen group attached to an aryl group having 6 to 60 carbon atoms.

[0042] Unless otherwise stated, the terms "aryl group" and "arylene group" as used in this invention have 6 to 60 carbon atoms, but are not limited thereto. In this invention, aryl group or arylene group means monocyclic or polycyclic aromatic, and includes aromatic rings formed by linkage or reaction of adjacent substituents.

[0043] For example, the aryl group can be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0044] The prefix “aryl” or “aromatic” indicates a group that is substituted by an aryl group. For example, an arylalkyl group can be an aryl-substituted alkyl group, and an arylalin group can be an aryl-substituted alkenyl group, and the aryl-substituted group has the number of carbon atoms as defined herein.

[0045] Furthermore, when prefixes are named sequentially, this means that substituents are listed in the order they are first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0046] Unless otherwise stated, the term "heterocyclic group" as used herein contains one or more heteroatoms and has, but is not limited to, 2 to 60 carbon atoms, including any of monocyclic and polycyclic rings, and may include heteroaliphatic and heteroaromatic rings. Furthermore, it may combine with adjacent groups to form a heterocyclic group.

[0047] Unless otherwise stated, the term "heteroatom" as used herein means at least one of N, O, S, P, or Si.

[0048] Furthermore, the term "heterocyclic group" can include rings in which SO2 replaces the carbon atoms that make up the ring. For example, "heterocyclic group" includes the following compounds.

[0049]

[0050] Unless otherwise stated, the terms “fluorenyl group” or “fluoreneyl group” as used herein mean that R, R' and R” are all monovalent or divalent functional groups of hydrogen in the following structures, and the terms “substituted fluorenyl group” or “substituted fluoreneyl group” mean that at least one of the substituents R, R', and R” is a substituent other than hydrogen, and include those in which R and R' are bonded to each other to form a spiro compound together with the carbons they are bonded to.

[0051]

[0052] As used in this article, the term "spiro compound" has a "spiral connection," and a spiral connection means a connection in which two rings share only one atom. In this case, the atom shared by the two rings is called a "spiro atom," and these compounds are called "single-spiro," "double-spiro," and "triple-spiro," respectively, depending on the number of spiro atoms in the compound.

[0053] Unless otherwise stated, as used herein, the term "aliphatic" means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0054] Unless otherwise stated, as used herein, the term "ring" means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by combination thereof, and includes saturated or unsaturated rings.

[0055] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain, but are not limited to, one or more hetero atoms.

[0056] Furthermore, unless explicitly stated otherwise, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogens, amino groups, nitrile groups, nitro groups, C1-C6 groups, and C2-C4 groups. 20 Alkyl groups, C1-C 20 alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 aryl group, deuterated C6-C 20 aryl group, C8-C 20 Aryl alkenyl groups, silyl groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not limited to these substituents.

[0057] Furthermore, unless otherwise explicitly explained, the formulas used in this invention are identical to the definitions of substituents defined by the index in the following formulas.

[0058]

[0059] Here, when a is an integer of 0, the substituent R 1 There is no unique substituent R when a is an integer of 1. 1 When a is an integer of 2 or 3, the carbon atom attached to any one of the carbon atoms forming the benzene ring is bonded as follows, where R 1 They can be the same or different from each other. When a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, but the indication of the hydrogens bonded to the carbons that form the benzene ring is omitted.

[0060]

[0061] In the following text, reference will be made to Figures 1 to 3 Describes the laminated structure of an organic electronic device comprising the compounds of the present invention.

[0062] When adding reference numerals to components in each figure, it should be noted that even if the same component is shown in different figures, the same component should be given the same reference numerals as much as possible. Furthermore, in describing the invention, detailed descriptions of known configurations or functions will be omitted if it is determined that such detailed descriptions might obscure the essential points of the invention.

[0063] Figures 1 to 3 This is a schematic diagram of an organic electronic component according to an embodiment of the present invention.

[0064] refer to Figure 1 According to an embodiment of the present invention, an organic electronic component (100) includes a first electrode (110), a second electrode (170) formed on a substrate (not shown) and an organic material layer formed between the first electrode (110) and the second electrode (170).

[0065] The first electrode (110) can be an anode (anode), and the second electrode (170) can be a cathode (cathode). In the case of the inverted type, the first electrode can be a cathode and the second electrode can be an anode.

[0066] The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). Specifically, the hole injection layer (120), the hole transport layer (130), 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).

[0067] Preferably, the light efficiency enhancement layer (180) can be formed on one surface of the organic material layer that is not in contact with the first electrode (110) or the second electrode (170), and when the light efficiency enhancement layer (180) is formed, the light efficiency of the organic electronic component can be improved.

[0068] For example, a light efficiency enhancement layer (180) can be formed on the second electrode (170). In the case of top-emitting organic light-emitting device, the light energy loss caused by surface plasmon polaritons (SPP) in the second electrode (170) can be reduced by forming a light efficiency enhancement layer (180). In the case of bottom-emitting organic light-emitting device, the light efficiency improvement layer (180) can be used as a buffer for the second electrode (170).

[0069] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will refer to Figure 2 Describe it.

[0070] refer to Figure 2According to an embodiment of the present invention, the organic electronic element (200) includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) sequentially formed on a first electrode (110), and a light efficiency enhancement layer (180) may be formed on the second electrode.

[0071] although Figure 2 The electron transport auxiliary layer may be further formed between the light-emitting layer (140) and the electron transport layer (150), but it is not shown in the figure.

[0072] Furthermore, according to another embodiment of the invention, the organic material layer can have the form of a plurality of stacks in which a hole transport layer, a light-emitting layer, and an electron transport layer are formed. This will be referred to Figure 3 Describe it.

[0073] refer to Figure 3 In an organic electronic component (300) according to another embodiment of the present invention, two or more sets of organic material layer stacks (ST1, ST2) including a multilayer structure may be formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the organic material layer stacks.

[0074] Specifically, an organic electronic component according to an embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL), a second stack (ST2), a second electrode (170), and a light efficiency enhancement layer (180).

[0075] The first stack (ST1), which is an organic material layer formed on the first electrode (110), may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). Thus, the first stack and the second stack can be organic material layers having the same stack structure or organic material layers having different stack structures.

[0076] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). The charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute the charge.

[0077] When passing through, as Figure 3 The multilayer stacked structure method shown in the figure can form multiple light-emitting layers, and can also manufacture organic electroluminescent devices that emit white light through the mixing effect of light emitted from each light-emitting layer, and can also manufacture organic electroluminescent devices that emit light of various colors.

[0078] The compounds of Formula 1 of the present invention can be used as materials for hole injection layers (120, 320, 420), hole transport layers (130, 330, 430), buffer layers (210), light-emitting auxiliary layers (220), electron transport layers (150, 350, 450), electron injection layers (160), light-emitting layers (140, 340, 440), or light efficiency enhancement layers (180). Preferably, the compounds of Formula 1 of the present invention can be used as materials for hole transport band layers, such as hole transport layers (130, 330, 430) and / or light-emitting auxiliary layers (220), and the compounds of Formula 2 of the present invention can be used as the main body of light-emitting layers (140, 340, and 440).

[0079] Even with identical or similar nuclei, band gaps, electrical properties, and interfacial properties can vary depending on the position of the substituents. Therefore, it is necessary to study the selection of the nucleus and the combination of substituents bonded to it. In particular, when the energy levels and T1 values ​​between the layers of organic materials are optimally combined with the inherent properties of the material (mobility, interfacial properties, etc.), long service life and high efficiency can be achieved simultaneously.

[0080] The organic electroluminescent device according to embodiments of the present invention can be manufactured using various deposition methods. It can be manufactured using deposition methods such as PVD or CVD, for example, by depositing a conductive metal or metal oxide or alloy thereof on a substrate to form an anode (110), and after forming an organic material layer thereon comprising 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), it can be manufactured by depositing a material thereon that can serve as a cathode (170). Furthermore, a light-emitting auxiliary layer (220) can be formed between the hole transport layer (130) and the light-emitting layer (140), and an electron transport auxiliary layer (not shown) can also be formed between the light-emitting layer (140) and the electron transport layer (150), which can also be formed as a stacked structure as shown.

[0081] Furthermore, the organic material layer can be manufactured with fewer layers using various polymer materials, without vapor deposition methods, but through methods such as solution or solvent processes, for example, spin coating or nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll coating, doctor blade coating, screen printing, or thermal transfer. Since the organic material layer according to the invention can be formed by various methods, the scope of the invention is not limited to the method of formation.

[0082] Furthermore, the organic electronic components according to embodiments of the present invention can be selected from organic electroluminescent devices, organic solar cells, organic photosensitive materials, organic transistors, monochrome lighting devices, and quantum dot display devices.

[0083] Another embodiment of the present invention may include: a display device comprising the organic electronic elements of the present invention described above, and an electronic device including a control unit for driving the display device. In this case, the electronic device may be a current or future wired / wireless communication terminal, and includes all electronic devices, such as mobile communication terminals like portable phones, PDAs, electronic dictionaries, PMPs, remote controllers, navigation systems, game consoles, various TVs, and various computers.

[0084] Organic electronic devices according to aspects of the present invention will be described below.

[0085] An organic electronic component according to an embodiment of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes a light-emitting layer and a hole transport band layer formed between the light-emitting layer and the anode, wherein the hole transport band layer contains a compound represented by Formula 1, and the light-emitting layer contains a compound represented by Formula 2.

[0086]

[0087] in:

[0088] 1) X is O, S, or NR 5 .

[0089] 2) Y is O, S, or NR 6 .

[0090] 3) Rings A, B, and C are each independently C6-C 14 aryl group, in addition, ring A can be R 7 Replacement, ring B can be R 8 Replacement, and ring C can be R 9 replace.

[0091] 4)R 1 R 2 R 3 R 4 R 7 R 8 and R 9 Each is independently the same as or different from the others, and each is independently selected from hydrogen; deuterium; halogen; C1-C. 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; and C6-C 60 Arylamine group; or if a, b, c, and d are 2 or greater than 2, multiple adjacent R groups. 1 One or more R 2 One or more R 3 One or more R 4 They can bond together to form a ring.

[0092] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is an alkyl group, which can preferably be C1-C. 30 Alkyl groups, more preferably C1-C 24 Alkyl groups.

[0093] Where R1 R 2 R 3 R 4 R 7 R 8 and R 9 It is an alkoxy group, which can preferably be C1-C. 24 Alkoxy group.

[0094] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is an aryloxy group, which can preferably be C1-C. 24 Aryloxy group.

[0095] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is an aryl group, and it can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24 The aryl group can be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0096] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0097] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is a fused ring group, and it can preferably be C3-C. 30 Aliphatic rings and C6-C 30The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0098] Where R 1 R 2 R 3 R 4 R 7 R 8 and R 9 It is an arylamine group, which can preferably be C6-C. 30 arylamine groups, more preferably C6-C 24 arylamine group,

[0099] 5)R 5 It is C6-C 60 An aryl group; or a C2-C group containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups;

[0100] R 6 It is C6-C 60 An aryl group; or a C2-C group containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups; or L-Ar; L and L 1 The same, Ar and Ar 1 same,

[0101] Where R 5 and R 6 It is an aryl group, and it can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24 The aryl group can be, for example, phenylene, biphenyl, naphthyl, phenanthrene, terphenyl, etc.

[0102] Where R 5 and R 6 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, and more preferably C2-C 24 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine triazine, or quinoxaline.

[0103] 6) a, b, c and d are each an integer from 0 to 4.

[0104] 7) i and j are each an integer from 0 to 2, provided that i+j is an integer of 1 or greater than 1.

[0105] 8)L 1 L 2 and L 3 Each is independently selected from a single bond; C6-C 60 arylene group; fluorene group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C2-C 60 Heterocyclic groups;

[0106] Where L 1 L 2 and L 3 It is an aryl group, which can preferably be C6-C. 30 arylene groups, more preferably C6-C 24 Aromatic groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.

[0107] Where L 1 L 2 and L 3 It is a fused ring group, and it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0108] Where L 1 L 2 and L 3 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0109] 9)Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Each is independently selected from C1-C 60 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy group; C6-C 60aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; or Ar 1 and Ar 2 Or Ar 3 and Ar 4 They can bond together to form a ring.

[0110] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is an alkyl group, which can preferably be C1-C. 30 Alkyl groups, more preferably C1-C 24 Alkyl groups.

[0111] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is an alkoxy group, which can preferably be C1-C. 24 Alkoxy group.

[0112] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is an aryloxy group, which can preferably be C1-C. 24 Aryloxy group.

[0113] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is an aryl group, and it can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24 The aryl group can be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0114] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0115] If Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It is a fused ring group, and it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0116] 10) Wherein, the aryl group, arylene group, arylamine group, heterocyclic group, fluorenyl group, fluorene group, fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxy group may be substituted by one or more substituents, wherein the substituents are selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups; C7-C 20 arylalkyl groups; and C8-C 20 Aryl alkenyl groups; furthermore, substituents can bond to each other to form saturated or unsaturated rings, where the term "ring" refers to C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by their combination.

[0117] Furthermore, the compounds represented by Formula 1 are represented by any one of Formulas 1-1 to 1-7.

[0118]

[0119] in,

[0120] 1) X, R1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 and Ar 4 Same as defined above,

[0121] 2) a', b', c', and d' are each an independent integer from 0 to 3.

[0122] 3) b" and d" are each an integer from 0 to 2.

[0123] Furthermore, compounds represented by Formula 1 are represented by any one of Formulas 1-8 to 1-10.

[0124]

[0125] Among them, R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 Ar 4 The same applies to i and j as above.

[0126] Furthermore, Ar in Equation 1 1 To Ar 4 At least one of them is represented by equation B-1.

[0127] Formula B-1

[0128]

[0129] in,

[0130] 1)V 1 and V 2 Each is an independent single bond, NR 10 CR 11 R 12 O or S

[0131] 2)R 10 R 11 and R 12 With R 5 The definitions are the same, or R 11 and R 12 They can bond together to form a ring.

[0132] 3) Rings D and E are each independently C6-C 20 aryl group; or C4-C 20 Heterocyclic groups;

[0133] Furthermore, in Equation 1, R 1 To R 4 In any one of them, adjacent pairs bond to each other to form any one of benzene, indole, indene, benzofuran, and benzothiophene.

[0134] Specifically, the compound represented by Formula 1 can be any of the following compounds.

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] Furthermore, the compound represented by Formula 2 is represented by any one of Formulas 2-1 to 2-3.

[0145]

[0146] in

[0147] 1) Rings A, C, and R 8 L 3 Ar 5 Y is the same as defined above.

[0148] 2) e is 0 to 2, g and h are 0 or 1, and the condition is that g + h is 1.

[0149] Furthermore, the main compound represented by Formula 2 is represented by any one of Formulas 2-4 to 2-27.

[0150]

[0151]

[0152] in,

[0153] 1) Rings A, C, and R 8 L 3 and Ar 5 Same as defined above,

[0154] 2) e is between 0 and 2.

[0155] 3) R' and R" with R 1 The definitions are the same.

[0156] 4) L and L 1 The definitions are the same.

[0157] 5) Ar and Ar 1 The definitions are the same.

[0158] In addition, R 6 To R 9 and Ar 5 At least one of the expressions in is represented by any one of the formulas A-1 to A-6.

[0159]

[0160]

[0161] in,

[0162] 1)X 1 X 2 X 3 X 4 X 5 X 6 X 7 and X 8 Each can be independently C, C(R1), or N.

[0163] 2) Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently C(R1) or N.

[0164] 3) In equation A-1, X 1 To X 6 At least one of them is N,

[0165] 4) In equation A-2, X 1 To X 4 And at least one of Y1 to Y4 is N,

[0166] 5) In equation A-3, X 1 To X 6 At least one of them is N,

[0167] 6) In equation A-4, X 5 To X 8And at least one of Y1 to Y8 is N,

[0168] 7) In equation A-5, X 1 To X 4 At least one of them is N,

[0169] 8) In equation A-6, X 1 X 2 X 3 X 4 and X 6 Each is independently C, C(R1) or N, Y 1 Is it O, S, N-L'-Ar' or CR? 13 C 14 Y 2 It is N.

[0170] 9) V and W are independently O, S, N-L'-Ar' or CR 13 C 14 ,

[0171] 10) m and n are each independently 0 or 1, provided that at least one of m and n is 1.

[0172] 11) R1, R 13 and R 14 Each is independently selected from hydrogen; deuterium; halogen; C1-C 20 Alkyl groups; or unsubstituted or C6-C 20 aryl-substituted silane groups; cyano groups; nitro groups; C1-C 20 Alkyl thio 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 group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic ring; C7-C 20 arylalkyl groups; and C8-C 20 Aryl alkenyl groups; adjacent R1, adjacent R 13 and adjacent R 14 They can bond together to form a ring.

[0173] 12) Where Ar' is selected from C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20Heterocyclic group; C3-C 20 Aliphatic rings; and their combinations,

[0174] 13) Where L' is independently selected from single bonds; C6-C 20 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 20 Heterocyclic groups; and C3-C 20 Aliphatic cyclic groups;

[0175] Specifically, the compound represented by Formula 2 can be any of the following compounds.

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] Furthermore, the present invention provides a compound comprising at least one hole transport band layer between a first electrode and a light-emitting layer, wherein the hole transport band layer comprises a hole transport layer, a light-emitting auxiliary layer, or both, and the hole transport band layer comprises a compound represented by Formula 1.

[0192] It may also include a light efficiency enhancement layer formed on at least one surface of the anode and cathode opposite the organic material layer.

[0193] In addition, the organic material layer may include two or more stacks, each stack including a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the anode, and the organic material layer may also include a charge-generating layer formed between the two or more stacks.

[0194] In another aspect, the present invention provides an electronic device comprising a display device including organic electronic components; and a control unit for driving the display device. In this case, the organic electronic components are at least one of OLED, organic solar cell, organic photoconductor (OPC), organic transistor (organic TFT), and components for monochrome or white illumination.

[0195] In the following, examples of the synthesis of compounds represented by formulas according to the present invention and examples of the preparation of organic electronic devices will be described in detail with reference to the embodiments, but the present invention is not limited to the following embodiments.

[0196] [Synthesis example 1]

[0197] The compound represented by Formula 1 according to the invention (final product 1) can be prepared by the reaction shown in reaction scheme 1, but is not limited thereto.

[0198] <Reaction Scheme 1>

[0199]

[0200] Hal1 and Hal2 are Cl, Br, or I, and G1 is Ar. 1 Or Ar 3 G2 is Ar 2 Or Ar 4 .

[0201] I. Example of Sub 1 Synthesis

[0202] Sub 1 of reaction scheme 1 can be synthesized through the reaction pathway of reaction scheme 2, but is not limited to this.

[0203] <Reaction Scheme 2>

[0204]

[0205] Examples of the synthesis of specific compounds belonging to Sub 1 are as follows.

[0206] Synthesis example of Sub 1-1

[0207]

[0208] (1) Synthesis of Sub 1-1A

[0209] 4-Chloro-9H-xanthon-9-one (20 g, 86.71 mmol) and 2-bromo-1,1'-biphenyl (21.22 g, 91.05 mmol) were dissolved in THF (600 mL), and the reaction mixture was then cooled to -78 °C. After the slow addition of n-BuLi (2.5 M in hexane) (6.11 g, 95.38 mmol), the reaction mixture was stirred at room temperature for 4 hours. When the reaction was complete, the reactants were quenched in H₂O, and then the water was removed. The mixture was filtered under reduced pressure, and the product obtained by concentrating the organic solvent was separated by column chromatography to obtain 29.7 g of product (yield: 89%).

[0210] (2) Synthesis of Sub 1-1

[0211] Sub 1-1A (20 g, 51.97 mmol), HCl (4 ml), and acetic acid (208 ml) were added, and the mixture was stirred at 80 °C for 1 hour. When the reaction was complete, the mixture was filtered under reduced pressure, and the product obtained by concentrating the organic solvent was then separated by column chromatography to obtain 17.54 g of product. (Yield: 92%)

[0212] Synthesis examples in Sub 1-6

[0213]

[0214] (1) Synthesis of Sub 1-6A

[0215] 4-Chloro-9H-xanthon-9-one (20 g, 101.93 mmol) and 2-bromo-1,1'-biphenyl (28.64 g, 107.03 mmol), THF (680 ml), and n-BuLi (2.5 M in hexane) (7.18 g, 112.12 mmol) were synthesized in the same manner as in Sub1-1A to obtain the product (33.3 g, 85%).

[0216] (2) Synthesis of Sub 1-6

[0217] Sub 1-6A (20 g, 51.97 mmol), HCl (4 ml), and acetic acid (208 ml) were synthesized in the same manner as in the synthesis of Sub 1-1 to obtain the product (16.78 g, 88%).

[0218] Synthesis examples in Sub 1-46

[0219]

[0220] (1) Synthesis of Sub 1-46A

[0221] 3-Chloro-9H-thioxanthone-9-one (20 g, 81.07 mmol) and 2-bromo-1,1'-biphenyl (19.84 g, 85.12 mmol), THF (600 ml), and n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol) were synthesized in the same manner as in Sub1-1A to obtain the product (25.7 g, 79%).

[0222] (2) Synthesis of Sub 1-46

[0223] Sub 1-46A (20.8 g, 51.97 mmol), HCl (4 ml), and acetic acid (200 ml) were synthesized in the same manner as in the synthesis of Sub 1-1 to obtain the product (15.47 g, 81%).

[0224] Synthesis examples in Sub 1-55

[0225]

[0226] (1) Synthesis of Sub 1-55A

[0227] 2-Chloro-9H-thioxanthone-9-one (20 g, 81.07 mmol) and 4-bromo-2-iodo-1,1'-biphenyl (30.56 g, 85.12 mmol), THF (600 ml), and n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol) were synthesized in the same manner as in Sub1-1A to obtain the product (33.06 g, 85%).

[0228] (2) Synthesis of Sub 1-55

[0229] Sub 1-55A (20 g, 41.68 mmol), HCl (3.5 ml), and acetic acid (167 ml) were synthesized in the same manner as in the synthesis of Sub 1-1 to obtain the product (16.75 g, 87%).

[0230] Synthesis examples in Sub 1-72

[0231]

[0232] (1) Synthesis of Sub 1-72A

[0233] 3-(3-chlorophenyl)-10-phenylacridin-9(10H)-one (20 g, 52.38 mmol), 2-bromo-1,1'-biphenyl (12.82 g, 54.99 mmol), THF (500 ml), and n-BuLi (2.5 M in hexane) (3.7 g, 57.61 mmol) were synthesized in the same manner as in Sub1-1A to obtain the product (25 g, 89%).

[0234] (2) Synthesis of Sub 1-72

[0235] Sub 1-72A (20 g, 37.31 mmol), HCl (3 ml), and acetic acid (150 ml) were synthesized in the same manner as in the synthesis of Sub 1-1 to obtain the product (17.59 g, 91%).

[0236] In addition, compounds belonging to Sub 1 can be, but are not limited to, the following compounds.

[0237]

[0238]

[0239]

[0240] Table 1 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub 1.

[0241] [Table 1]

[0242]

[0243]

[0244] II. Example of Sub 2 Synthesis

[0245] Sub 1 of reaction scheme 2 can be synthesized through the reaction pathway of reaction scheme 3, but is not limited to this.

[0246] <Reaction Scheme 3>

[0247]

[0248] Among them, G1 is Ar 1 Or Ar 3 G2 is Ar 2 Or Ar 4 .

[0249] Synthesis example in Sub 2-1

[0250]

[0251] After adding bromobenzene (37.1 g, 236.2 mmol) to a round-bottom flask and dissolving it in toluene (2,200 mL), aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol), and NaOt-Bu (62 g, 644.3 mmol) were added sequentially and the mixture was stirred at 100 °C. When the reaction was complete, the mixture was extracted with diethyl ether and water, the organic layer was dried over MgSO₄, concentrated, and the resulting compound was recrystallized from a silica gel column to obtain 28 g (77% yield) of Sub 2-1.

[0252] Synthesis example in Sub 2-37

[0253]

[0254] 3-Bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1,550 mL), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), Pd2(dba)3 (6.76 g, 7.4 mmol), P(t-Bu)3 (3 g, 14.8 mmol), and NaOt-Bu (42.6 g, 443.2 mmol) were synthesized in the same manner as in the synthesis of Sub 2-1 to obtain Sub 2-37 (37.9 g, 73%).

[0255] Compounds belonging to Sub 2 can be, but are not limited to, the following compounds.

[0256]

[0257]

[0258]

[0259] Table 2 shows the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 2.

[0260] [Table 2]

[0261]

[0262]

[0263] III. Synthesis Example of Final Product 1

[0264] Synthesis example 1-1

[0265]

[0266] After adding Sub 1-1 (10 g, 27.26 mmol) to a round-bottom flask and dissolving it in toluene (300 mL), Sub 2-1 (5.07 g, 29.99 mmol), Pd 2(dba) 3 (1.25 g, 1.36 mmol), P(t-Bu) 3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were added and the mixture was stirred at 100 °C. When the reaction was complete, the mixture was extracted with CH 2Cl 2 and water, the organic layer was dried over MgSO 4, concentrated, and the resulting compound was recrystallized from a silica gel column to obtain 11.7 g (86% yield) of the product.

[0267] Synthesis Example 1-15

[0268]

[0269] Sub 1-3 (10 g, 27.26 mmol), toluene (500 mL), Sub 2-27 (12.22 g, 29.99 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (15.89 g, 79%).

[0270] Synthesis Example 1-27

[0271]

[0272] Sub 1-3 (10 g, 27.26 mmol), toluene (500 mL), Sub 2-56 (9.22 g, 29.99 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (14.6 g, 84%).

[0273] Synthesis example 1-42

[0274]

[0275] Sub 1-50 (10 g, 23.40 mmol), toluene (500 mL), Sub 2-14 (5.64 g, 25.74 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (10.85 g, 82%).

[0276] Synthesis example 1-74

[0277]

[0278] Sub 1-59 (10 g, 18.07 mmol), toluene (500 mL), Sub 2-1 (3.36 g, 19.87 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (9.9 g, 85%).

[0279] Synthesis example 1-103

[0280]

[0281] Sub 1-56 (10 g, 21.65 mmol), toluene (500 mL), Sub 2-1 (4.03 g, 23.82 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (12.63 g, 90%).

[0282] Synthesis example 1-126

[0283]

[0284] Sub 1-70 (10 g, 20.32 mmol), toluene (500 mL), Sub 2-19 (3.81 g, 22.36 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (11.28 g, 89%).

[0285] Synthesis example 1-142

[0286]

[0287] Sub 1-85 (10 g, 18.24 mmol), toluene (500 mL), Sub 2-1 (3.4 g, 20.07 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were synthesized in accordance with Synthesis Example 1-1 to obtain the product (9.44 g, 76%).

[0288] Table 3 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to final product 1.

[0289] [Table 3]

[0290]

[0291]

[0292]

[0293]

[0294] [Synthesis example 2]

[0295] The compound represented by formula 2 according to the invention (final product 2) can be synthesized by reacting Sub 3 and Sub 4 according to reaction scheme 2, but is not limited thereto.

[0296] <Reaction Scheme 4>

[0297]

[0298] I. Example of Sub 3 Synthesis

[0299] Sub 3 of Scheme 4 can be synthesized through the reaction pathway of Scheme 5, but is not limited to this.

[0300] <Reaction Scheme 5>

[0301]

[0302]

[0303] 1. Synthesis example of Sub 3-1

[0304]

[0305] (1) Synthesis of Sub 3-1a

[0306] 2-Bromo-9-phenyl-9H-carbazole (50 g, 155.18 mmol), bis(pinacol)diboron (32.17 g, 126.70 mmol), KOAc (45.69 g, 465.54 mmol), and PdCl2(dppf) (3.41 g, 4.66 mmol) were dissolved in DMF (1 L) solvent and then refluxed at 120 °C for 12 hours. When the reaction was complete, the reactants were cooled to room temperature, extracted with CH2Cl2, and washed with water. The organic material layer was dried over MgSO4 and concentrated, and the resulting organic material was recrystallized from CH2Cl2 and methanol solvent to obtain the desired product (47.03 g, 81%).

[0307] (2) Synthesis of Sub 3-1b

[0308] The obtained Sub 3-1a (46.94 g, 127.12 mmol), 1-bromo-2-nitrobenzene (25.68 g, 127.12 mmol), K₂CO₃ (52.70 g, 381.36 mmol), and Pd(PPh₃)₄ (4.41 g, 3.81 mmol) were placed in a round-bottom flask, and then THF (600 mL) and water (300 mL) were added to dissolve them. The mixture was then refluxed at 80 °C for 12 hours. When the reaction was complete, the reactants were cooled to room temperature, extracted with CH₂Cl₂, and washed with water. The organic layer was dried over MgSO₄ and concentrated, and the resulting organic material was separated using a silica gel column to obtain the desired product (31.97 g, 69%).

[0309] (3) Synthesis of Sub 3-1

[0310] The obtained Sub 3-1b (31.97 g, 87.73 mmol) and triphenylphosphine (57.53 g, 219.33 mmol) were dissolved in o-dichlorobenzene (500 ml) and refluxed at 200 °C for 24 hours. When the reaction was complete, the solvent was removed by vacuum distillation, and the concentrated product was recrystallized using a silica gel column to obtain the desired product (20.42 g, 70%).

[0311] 2. Synthesis example of Sub 3-16

[0312]

[0313] (1) Synthesis of Sub 3-16a

[0314] 5-Bromobenzo[b]naphtho[1,2-d]thiophene (50 g, 159.64 mmol), bis(pinacol)diboron (44.59 g, 175.60 mmol), KOAc (47 g, 478.91 mmol), and PdCl2(dppf) (3.50 g, 4.79 mmol) were prepared in the same manner as in Sub 1-1a to obtain the product (46.01 g, 80%).

[0315] (2) Synthesis of Sub 3-16b

[0316] The obtained Sub 3-16a (45.94 g, 156.17 mmol), 1-bromo-2-nitrobenzene (38.90 g, 156.17 mmol), K2CO3 (64.75 g, 468.51 mmol), Pd(PPh3)4 (5.41 g, 4.69 mmol), THF (680 ml), and water (340 ml) were subjected to the same experimental method as that for Sub 1-1b to obtain the product (38.85 g, 70%).

[0317] (3) Synthesis of Sub 3-16

[0318] The obtained 3-16b (38.85 g, 109.31 mmol) and triphenylphosphine (71.68 g, 273.28 mmol), o-dichlorobenzene (547 mL) were processed in the same manner as in Sub 3-1 to obtain the product (25.81 g, 73%).

[0319] 3. Synthesis example of Sub 3-115

[0320]

[0321]

[0322] (1) Synthesis of Sub 3-115a

[0323] 2-Bromodibenzo[b,d]thiophene (50 g, 190 mmol), bis(pinacol)diboron (53.07 g, 209 mmol), KOAc (55.94 g, 570 mmol), and PdCl2(dppf) (4.17 g, 5.7 mmol) were prepared in the same manner as in Sub 3-1a to obtain the product (46.87 g, 81%).

[0324] (2) Synthesis of Sub 3-115b

[0325] The obtained Sub 3-115a (46.87 g, 151.09 mmol), 1-bromo-2-nitrobenzene (30.52 g, 151.09 mmol), K2CO3 (62.64 g, 453.27 mmol), Pd(PPh3)4 (5.24 g, 4.53 mmol), THF (540 ml), and water (270 ml) were subjected to the same experimental method as that for Sub 3-1b to obtain the product (32.68 g, 71%).

[0326] (3) Synthesis of Sub 3-115

[0327] The obtained Sub 3-115b (32.68 g, 107.02 mmol), triphenylphosphine (70.18 g, 267.55 mmol), and o-dichlorobenzene (466 mL) were subjected to the same procedure as in the Sub 3-1 experiment to obtain the product (19.83 g, 68%).

[0328] 4. Synthesis example of Sub 3-160

[0329]

[0330] (1) Synthesis of Sub 3-160a

[0331] 12-Bromophenanthro[9,10-b]benzofuran (34.2 g, 98.50 mmol), bis(pinacol)diboron (27.51 g, 108.35 mmol), KOAc (29 g, 295.50 mmol), PdCl2(dppf) (2.16 g, 2.95 mmol), and DMF (621 mL) were prepared in the same manner as in Sub 3-1a to obtain the product (26.02 g, 67%).

[0332] (2) Synthesis of Sub 3-160b

[0333] The obtained Sub 3-160a (26 g, 65.94 mmol), 1-bromo-2-nitrobenzene (13.32 g, 65.94 mmol), K2CO3 (27.34 g, 197.93 mmol), Pd(PPh3)4 (2.29 g, 1.98 mmol), THF (290 ml), and water (145 ml) were reacted in the same manner as in the experiment for Sub 3-1b to obtain the product (20.03 g, 78%).

[0334] (3) Synthesis of Sub 3-160

[0335] The obtained Sub 3-160b (19.87 g, 51.03 mmol), triphenylphosphine (33.46 g, 127.56 mmol), and o-dichlorobenzene (255 ml) were subjected to the same procedure as that for Sub 3-1 to obtain the product (7.11 g, 39%).

[0336] 5. Synthesis example of Sub 3-208

[0337]

[0338] (1) Synthesis of Sub 3-208a

[0339] 6-Bromobenzo[b]naphtho[2,1-d]thiophene (60 g, 191.56 mmol), bis(pinacol)diboron (53.51 g, 210.72 mmol), KOAc (56.40 g, 574.69 mmol), PdCl2(dppf) (4.21 g, 5.75 mmol), and DMF (1,207 mL) were prepared in the same manner as in Sub 3-1a to obtain the product (53.14 g, 77%).

[0340] (2) Synthesis of Sub 3-208b

[0341] The obtained Sub 3-208a (53.14 g, 147.50 mmol), 1-bromo-2-nitrobenzene (29.80 g, 147.50 mmol), K2CO3 (61.16 g, 442.49 mmol), and Pd(PPh3)4 (5.11 g, 4.42 mmol) were processed in the same manner as those used for Sub 3-1b to obtain the product (41.94 g, 80%).

[0342] (3) Synthesis of Sub 3-208

[0343] The obtained Sub 3-208b (41.94 g, 118.00 mmol) and triphenylphosphine (77.38 g, 295.01 mmol), o-dichlorobenzene (590 ml) were processed in the same manner as in the Sub 3-1 experiment to obtain the product (19.85 g, 52%).

[0344] 6. Synthesis example of Sub 3-282

[0345]

[0346] (1) Synthesis of Sub 3-282b

[0347] Sub 3-282a (45 g, 124.90 mmol), 3-bromo-4-nitro-1,1'-biphenyl (35.74 g, 124.90 mmol), K2CO3 (51.79 g, 374.71 mmol), Pd(PPh3)4 (4.33 g, 3.75 mmol), THF (550 ml), and water (275 ml) were prepared in the same manner as in Sub 3-1b to obtain the product (38.27 g, 71%).

[0348] (2) Synthesis of Sub 3-282

[0349] The obtained Sub 3-282b (38.27 g, 88.69 mmol), triphenylphosphine (58.16 g, 221.72 mmol), and o-dichlorobenzene (443 mL) were processed in the same manner as in the Sub 3-1 experiment to obtain the product (14.53 g, 41%).

[0350] Examples of Sub 3 are shown below, but not limited to, and Table 4 shows the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 3.

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359] [Table 4]

[0360]

[0361]

[0362]

[0363]

[0364] II. Example of Sub 4 Synthesis

[0365] Sub 4 of reaction scheme 4 can be synthesized via the reaction pathway of reaction scheme 6, but is not limited to this. In this case, Hal 1 It is I, Br, or Cl, and Hal 2 It is Br or Cl.

[0366] <Reaction Scheme 6>

[0367]

[0368] 1. Synthesis example of Sub 4-35

[0369]

[0370] (1) Synthesis of Sub 4-35a

[0371] The starting material 1-amino-2-naphthoic acid (CAS Registry No.: 4919-43-1) (75.11 g, 401.25 mmol) was placed in a round-bottom flask containing urea (CAS Registry No.: 57-13-6) (168.69 g, 2808.75 mmol) and stirred at 160 °C.

[0372] After confirming the reaction by TLC, the mixture was cooled to 100°C, water (200 ml) was added, and the mixture was stirred for 1 hour. When the reaction was complete, the resulting solid was filtered under reduced pressure, washed with water, and dried to obtain 63.86 g (yield: 75%) of product.

[0373] (2) Synthesis of Sub 4-35b

[0374] At room temperature, the obtained Sub 4-35a (63.86 g, 300.94 mmol) was dissolved in POCl3 (200 mL) in a round-bottom flask, followed by the slow, dropwise addition of N,N-diisopropylethylamine (97.23 g, 752.36 mmol) and stirring at 90 °C. After the reaction was complete, the mixture was concentrated and then added to ice water (500 mL), and stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 67.47 g of product (yield: 90%).

[0375] (3) Synthesis of Sub 4-35

[0376] The obtained Sub 4-35b (67.47 g, 270.86 mmol) was dissolved in THF (950 mL) in a round-bottom flask, and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborhecyclopentane (CAS Registry No.: 24388-23-6) (60.80 g, 297.94 mmol), Pd(PPh3)4 (12.52 g, 10.83 mmol), K2CO3 (112.30 g, 812.57 mmol), and water (475 mL) were added and stirred at 90 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized by silica gel column chromatography to obtain 44.89 g (yield: 57%) of product.

[0377] 2. Synthesis example of Sub 4-40

[0378]

[0379] Add 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane (CAS Registry No.: 947770-80-1) (22.44 g, 76.28 mmol), Pd(PPh3)4 (1.32 g, 1.14 mmol), K2CO3 (15.81 g, 114.42 mmol), THF (336 ml), and water (168 ml) to the starting material Sub 4-40b (19 g, 76.28 mmol) and use the synthetic method of Sub 4-35 to obtain 15.69 g (yield: 54%) of product.

[0380] 3. Synthesis examples of Sub 4-43

[0381]

[0382] Add 4,4,5,5-tetramethyl-2-(naphthio-1-yl)-1,3,2-dioxaborhexacyclopentane (CAS Registry No.: 160199-05-3) (32.01 g, 125.47 mmol), Pd(PPh3)4 (5.80 g, 5.02 mmol), K2CO3 (52.02 g, 376.41 mmol), THF (336 ml), and water (168 ml) to the starting material 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (CAS Registry No.: 160199-05-3) (32.01 g, 125.47 mmol), and use the synthetic method of Sub 4-35 to obtain 19.58 g (yield: 45%) of product.

[0383] The compounds belonging to Sub 4 can be, but are not limited to, the following compounds, and Table 5 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub 4.

[0384]

[0385]

[0386] [Table 5]

[0387]

[0388]

[0389] III. Synthesis Example of Final Product 2

[0390] Sub 3 (1 equivalent) was dissolved in toluene in a round-bottom flask, followed by the addition of Sub 4 (1.1 equivalent), Pd2(dba)3 (0.03 equivalent), P(t-Bu)3 (0.1 equivalent), and NaOt-Bu (3 equivalent), and the mixture was stirred at 100 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain the final product 1.

[0391] 1. Synthesis example 2-1

[0392]

[0393] After dissolving Sub 3-1 (10 g, 30.08 mmol) in toluene (302 mL) in a round-bottom flask, Sub 4-1 (5.19 g, 33.09 mmol), Pd2(dba)3 (0.83 g, 0.90 mmol), P(t-Bu)3 (0.61 g, 3.01 mmol), and NaOt-Bu (8.67 g, 90.24 mmol) were added and the mixture was stirred at 100 °C. After the reaction was complete, the organic layer was extracted with CH2Cl2 and water, dried over MgSO4, concentrated, and recrystallized from the compound using a silica gel column to obtain 8.14 g (yield: 66%) of the product.

[0394] 2. Synthesis example 2-23

[0395]

[0396] Sub 3-11 (10 g, 30.92 mmol), toluene (325 mL), Sub 4-35 (9.89 g, 34.01 mmol), Pd2(dba)3 (0.85 g, 0.93 mmol), P(t-Bu)3 (0.38 g, 1.86 mmol), and NaOt-Bu (8.91 g, 92.76 mmol) were synthesized using the method described for Sub 2-1 to obtain the final product (13.04 g, 73%).

[0397] 3. Synthesis example 2-53

[0398]

[0399] Sub 3-36 (10 g, 27.98 mmol), toluene (294 mL), Sub 4-47 (8.64 g, 30.78 mmol), Pd2(dba)3 (0.77 g, 0.84 mmol), P(t-Bu)3 (0.34 g, 1.68 mmol), and NaOt-Bu (8.07 g, 83.94 mmol) were synthesized using a 2-1 method to obtain the final product (11.45 g, 68%).

[0400] 4. Synthesis example 2-92

[0401]

[0402] Sub 3-79 (10 g, 26.78 mmol), toluene (281 mL), Sub 4-55 (9.67 g, 26.78 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), P(t-Bu)3 (0.16 g, 0.80 mmol), and NaOt-Bu (3.86 g, 40.16 mmol) were synthesized using a 2-1 method to obtain the final product (12.25 g, 70%).

[0403] 5. Synthesis Example 3-21

[0404]

[0405] After dissolving Sub 3-111 (3.90 g, 12.06 mmol) in toluene (127 ml), Sub 4-28 (2.90 g, 12.06 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), P(t-Bu)3 (0.24 g, 1.21 mmol), and NaOt-Bu (3.48 g, 36.18 mmol) were synthesized using a 2-1 method to obtain the final product (6.61 g, 76%).

[0406] 6. Synthesis example 4-1

[0407]

[0408] After dissolving Sub 3-164 (5.3 g, 16.39 mmol) in toluene (172 ml), Sub 4-1 (4.86 g, 16.39 mmol), Pd2(dba)3 (0.45 g, 0.49 mmol), P(t-Bu)3 (0.20 g, 0.98 mmol), and NaOt-Bu (4.72 g, 49.16 mmol) were synthesized using a 2-1 method to obtain the product (7.56 g, 79%).

[0409] 7. Synthesis Example 4-37

[0410]

[0411] Sub 3-190 (7 g, 19.59 mmol), toluene (206 ml), Sub 4-47 (5.50 g, 19.59 mmol), Pd2(dba)3 (0.54 g, 0.59 mmol), P(t-Bu)3 (0.24 g, 1.18 mmol), and NaOt-Bu (5.65 g, 58.76 mmol) were synthesized using a 2-1 method to obtain the product (7.54 g, 64%).

[0412] Table 6 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to final product 2.

[0413] [Table 6]

[0414]

[0415]

[0416]

[0417]

[0418] [Example 1] Red Organic Light Emitting Diode

[0419] First, on an ITO layer (anode) formed on a glass substrate, a 60 nm thick film of N1-(naphthyl-2-yl)-N4,N4-bis(4-(naphthyl-2-yl(phenyl)amino)phenyl)-N1-phenylphenyl-1,4-diamine (hereinafter abbreviated as 2-TNATA) is vacuum deposited to form a hole injection layer. Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) is vacuum deposited on this film to a thickness of 60 nm to form a hole transport layer. Finally, compounds (1-11) of the present invention are vacuum deposited to a thickness of 30 nm as a light-emitting auxiliary layer material to form a light-emitting auxiliary layer. Then, by doping (piq)2Ir(acac)[bis-(1-phenylisoquinolinyl)acetylacetonate iridium(III)] as a dopant with the main component of the present invention, compound 2-14, at a weight ratio of 95:5, a light-emitting layer with a thickness of 30 nm is deposited on the light-emitting auxiliary layer. Then, on the light-emitting layer, (1,1'-biphenyl)-4-oxo)bis(2-methyl-8-quinoline oxo)aluminum (hereinafter abbreviated as BAlq) is vacuum-deposited to a thickness of 10 nm to form a hole-blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited on the hole-blocking layer to a thickness of 40 nm to form an electron transport layer. Then, on the electron transport layer, LiF, as an alkali metal halide, is deposited to a thickness of 0.2 nm as an electron injection layer, and then Al is deposited to a thickness of 150 nm and used as a cathode, thereby fabricating an organic electroluminescent device.

[0420] [Example 2] to [Example 20]

[0421] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the compounds of the present invention shown in Table 7 were used for the light-emitting auxiliary layer and the light-emitting layer.

[0422] [Example 21]

[0423] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the compounds of the present invention were used in the hole transport layer, the light-emitting auxiliary layer, and the light-emitting layer as shown in Table 7.

[0424] [Comparative Example 1]

[0425] The organic electroluminescent device was manufactured in the same manner as in Example 1, but without using the light-emitting auxiliary layer.

[0426] Comparative Examples 2 through 6

[0427] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the light-emitting auxiliary layer material and the main material were used as shown in Table 7.

[0428]

[0429] Electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 21 and Comparative Examples 1 to 6 of the present invention, and lifetime measurement was performed at 2500 cd / m² using a lifetime measurement device manufactured by McScience. 2 The lifespan of the T95 was measured under standard brightness. The measurement results are shown in Table 7.

[0430] [Table 7]

[0431]

[0432]

[0433] As can be seen from the results in Table 7, the driving voltage of Examples 1 to 20, which used the compound of the present invention represented by Formula 1 as the light-emitting auxiliary layer material and the compound of the present invention represented by Formula 2 as the light-emitting layer material, was reduced, and the efficiency and lifespan were significantly improved. For Comparative Examples 2 to 4, which used one of Comparative Compounds 1 to 3 in the light-emitting auxiliary layer, the driving voltage of the device was reduced, and the efficiency and lifespan were improved compared to Comparative Example 1, which used Comparative Compound 4 as the main body without forming a light-emitting auxiliary layer. Furthermore, the device performance of Comparative Examples 5 and 6 was superior to that of Comparative Examples 2 to 4, and compared to Comparative Examples 1 to 6, when the light-emitting auxiliary layer was formed using the compound of the present invention represented by Formula 1 and the compound represented by Formula 2 was used as the main body, the driving voltage, efficiency, and lifespan of the device were significantly improved.

[0434] This is believed to be because the compounds of the present invention, represented by Formula 1, possess deep HOMO energy levels, which, when used as a light-emitting auxiliary layer, allow holes and electrons to achieve charge balance and emit light within the light-emitting layer rather than at the hole transport layer interface, thereby maximizing efficiency. Furthermore, by using the compounds of the present invention, represented by Formula 2, as the phosphorescent host, it has been determined that the combination of these elements exhibits an electrochemical synergistic effect to improve overall element performance.

[0435] Furthermore, in the evaluation results of the above-mentioned device manufacturing, the device characteristics in which the compound represented by Formula 1 is applied to the light-emitting auxiliary layer are described. However, as in the device results of Example 21, excellent performance is also shown when applied to one or more of the hole transport layer and the light-emitting auxiliary layer.

[0436] While exemplary embodiments of the invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the invention as disclosed in the appended claims. Therefore, the embodiments disclosed herein are intended to illustrate the scope of the inventive concept, and the scope of the invention is not limited by the embodiments. The scope of the invention should be interpreted based on the appended claims, and should be construed as including all inventive concepts within the scope of equivalent claims.

[0437] Industrial applicability

[0438] According to the present invention, an organic device with excellent device characteristics such as high brightness, high luminescence and long service life can be manufactured, thus possessing industrial applicability.

Claims

1. An organic electronic element, comprising: An anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes a light-emitting layer and a hole transport band layer formed between the light-emitting layer and the anode, wherein the hole transport band layer comprises a compound represented by Formula 1, and the light-emitting layer comprises a compound represented by Formula 2-6, Formula 2-8, Formula 2-9, Formula 2-10, Formula 2-12, Formula 2-13, Formula 2-14, Formula 2-16, Formula 2-17, Formula 2-18, Formula 2-20, Formula 2-21, Formula 2-22, Formula 2-25, or Formula 2-26. Formula 1 in: 1) X is O, S or NR 5 , 2) each of ring A and ring C is independently C6-C 14 aryl group, in addition, ring A can be substituted with R 7 and ring C can be substituted with R 9 and ring C can be substituted with R 3) R 1 R 2 R 3 R 4 R 7 R 8 and R 9 Each is independently the same as or different from the others, and each is independently selected from hydrogen; deuterium; halogen; C1-C. 50 Alkyl group; C2-C 20 alkenyl group; C1-C 30 Alkoxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C6-C 60 Arylamine group; or if a, b, c, and d are 2 or greater than 2, multiple adjacent R groups. 1 One or more R 2 One or more R 3 One or more R 4 They can bond together to form a ring. 4) R 5 is a C6-C 60 aryl group; or a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; L and L 1 identical, Ar and Ar 1 identical, 5) a, b, c, and d are each independent integers from 0 to 4, and e is from 0 to 2. 6) i and j are each independent integers from 0 to 2, provided that i + j is 1 or an integer greater than 1. 7) L 1 , L 2 and L 3 are each independently selected from a single bond; a C6-C 60 arylene group; a fluorenylene group; and a C2-C 60 heterocyclic group; 8) Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Each is independently selected from C1-C 60 Alkyl groups; C6-C 60 aryl group; fluorenyl group; and C2-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; or Ar 1 and Ar 2 Or Ar 3 and Ar 4 They can bond together to form a ring. 9) Wherein, the aryl group, the arylene group, the arylamine group, the heterocyclic group, the fluorenyl group, the fluorene group, the alkyl group, the alkenyl group, and the alkoxy group may be substituted by one or more substituents, wherein the substituents are selected from deuterium; halogens; cyano groups C1-C 20 Alkyl group; C2-C 20 alkenyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 aryl group; fluorenyl group; and C2-C 20 Heterocyclic groups; furthermore, substituents can bond to each other to form saturated or unsaturated rings, where the term "ring" refers to C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by their combination.

2. The organic electronic device of claim 1, wherein the compound represented by formula 1 is represented by any one of formulas 1-1 to 1-7: Equation 1-1 Equation 1-2 Equation 1-3 Equation 1-4 Equation 1-5 Equation 1-6 Equation 1-7 in: 1) X, R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 and Ar 4 Same as defined in claim 1, 2) a', b', c', and d' are each an independent integer from 0 to 3. 3) b" and d" are each an integer from 0 to 2.

3. The organic electronic device of claim 1, wherein the compound represented by formula 1 is represented by any one of formulas 1-8 to 1-10: Formula 1-8 Formula 1-9 Formula 1-10 Where R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 Ar 4 i and j are the same as those defined in claim 1.

4. The organic electronic element according to claim 1, wherein at least one of Ar in Formula 1 1 to Ar 4 is represented by Formula B-1: Formula B-1 in: 1) V 1 and V 2 each independently is a single bond, NR 10 , CR 11 R 12 , O or S, 2) R 10 , R 11 , and R 12 are the same as the definition of R 5 in claim 1, or R 11 and R 12 may be linked to each other to form a ring, 3) Rings D and E are each independently C6-C 20 aryl group; or C4-C 20 Heterocyclic groups.

5. The organic electronic element according to claim 1, wherein R in formula 1 1 to any one of R 4 in any one of R to R are bonded to each other to form any one of benzene, indole, indene, benzofuran and benzothiophene.

6. The organic electronic device of claim 1, wherein the compound represented by formula 1 can be any of the following compounds: 。 7. The organic electronic element of claim 1, wherein R 7 to R 9 and Ar 5 is represented by any one of Formula A-1 to Formula A-6: in: 1) X 1 X 2 X 3 X 4 X 5 X 6 X 7 and X 8 Each can be independently C, C(R1), or N. 2) Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently C(R1) or N. 3) In equation A-1, X 1 To X 6 At least one of them is N, 4) in formula A-2, X 1 to X 4 and at least one of Y1to Y4is N, 5) In formula A-3, X 1 to X 6 is N, 6) In formula A-4, X 5 to X 8 and at least one of Y1to Y8is N, 7) In formula A-5, X 1 to X 4 is N, 8) In equation A-6, X 1 X 2 X 3 X 4 and X 6 Each is independently C, C(R1) or N, Y 1 Is it O, S, N-L'-Ar' or CR? 13 C 14 Y 2 It is N. 9) V and W are each independently O, S, N-L'-Ar' or CR 13 C 14 , 10) m and n are each independently 0 or 1, provided that at least one of m and n is 1. 11) R1, R 13 and R 14 Each is independently selected from hydrogen; deuterium; halogen; cyano group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C6-C 20 aryl group; fluorenyl group; and C2-C containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; adjacent R1, adjacent R 13 and adjacent R 14 They can bond together to form a ring. 12) Where Ar' is selected from C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and their combinations, 13) Where L' is a single bond.

8. The organic electronic device of claim 1, wherein the compound represented by formula 2-6, formula 2-8, formula 2-9, formula 2-10, formula 2-12, formula 2-13, formula 2-14, formula 2-16, formula 2-17, formula 2-18, formula 2-20, formula 2-21, formula 2-22, formula 2-25 or formula 2-26 is any one of the following compounds: 。 9. The organic electronic device of claim 1, comprising at least one hole transport band layer between the anode and the light-emitting layer, wherein the hole transport band layer comprises a hole transport layer, a light-emitting auxiliary layer, or both, wherein the hole transport band layer comprises a compound represented by Formula 1.

10. The organic electronic component of claim 1, further comprising a light efficiency enhancement layer formed on at least one surface opposite the organic material layer in the surfaces of the anode and the cathode.

11. The organic electronic component of claim 1, wherein the organic material layer comprises two or more stacks, the stacks comprising a hole transport layer, a light-emitting layer and an electron transport layer sequentially formed on the anode.

12. The organic electronic component of claim 11, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacks.

13. An electronic device comprising: A display device comprising the organic electronic components as described in claim 1; And a control unit for driving the display device.

14. The electronic device of claim 13, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white illumination.

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