Compound for organic electric element, organic electric element using the compound, and electronic device having the organic electric element

Abstract

Provided are: a novel compound that can improve the light-emitting efficiency, stability, and lifespan of an element; an organic electrical device using the compound; and an electronic device having the organic electrical device.

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 an organic material layer disposed therebetween. Here, to improve the efficiency and stability of the organic electronic component, the organic material layer is typically composed of a multilayer structure made of different materials, and for example, the organic material layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, etc.

[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] The biggest issues with organic electroluminescent devices are lifespan and efficiency, and these issues must be addressed as display sizes become larger.

[0005] Efficiency, lifetime, and drive voltage are interrelated. As efficiency increases, the drive voltage relatively decreases. As the drive voltage decreases, the Joule heating generated during operation leads to less crystallization of the organic material, which results in a tendency for increased lifetime.

[0006] However, simply improving the organic material layers cannot maximize efficiency. This is because long lifetime and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between the various organic material layers, as well as the intrinsic properties of the materials (mobility, interface properties, etc.), are optimally combined.

[0007] Furthermore, in order to solve the light emission problem 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 it is now necessary to develop different light-emitting auxiliary layers according to each light-emitting layer (R, G, B).

[0008] 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.

[0009] However, the materials used in the hole transport layer must have low HOMO values, and therefore most of them have low T1 values. As a result, excitons generated in the emissive layer migrate to the hole transport layer, causing a charge imbalance within the emissive layer, and thus emitting light at the interface of the hole transport layer.

[0010] When light is emitted at the interface of the hole transport layer, problems arise such as reduced color purity and efficiency of organic electronic components, as well as shortened lifetime. 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.

[0011] Simultaneously, there is a need to develop hole injection layer materials with high glass transition temperatures that delay the penetration and diffusion of metal oxides from the inductively coupled oxide (ITO) layer to the organic layer (one of the reasons for the shortened lifetime of organic electronic components), while also exhibiting stable properties against Joule heating generated during device operation. It has been reported that low glass transition temperatures of hole transport layer materials reduce the uniformity of the film surface during device operation, which significantly affects device lifetime. Furthermore, since OLED devices are primarily formed through deposition methods, there is a need to develop materials that can withstand long-term deposition, particularly those with strong heat resistance.

[0012] In other words, in order to fully realize the superior characteristics of organic electronic components, the materials used to form organic material layers within the components (such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials) must be supported by stable and effective materials; however, the development of stable and effective organic material layer materials for organic electronic components has not yet been fully realized.

[0013] Therefore, there is a continued need to develop new materials, and in particular, there is an urgent need to develop materials for light-emitting auxiliary layers. Summary of the Invention

[0014] To address the problems mentioned above in the background art, the present invention has discovered compounds with novel structures, and further found that when these compounds are applied to organic electronic components, they can significantly improve the luminous efficiency, stability, and lifespan of the components.

[0015] Therefore, the object of the present invention is to provide novel compounds, organic electronic components using said compounds, and electronic devices thereof.

[0016] [Technical Solution]

[0017] The present invention provides compounds represented by Formula 1.

[0018]

[0019] In another aspect, the present invention provides organic electronic components and electronic devices thereof comprising compounds represented by Formula 1.

[0020] [The effects of the invention]

[0021] By using the compounds according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved. Attached Figure Description

[0022] Figures 1 to 3 This is an exemplary view of an organic electroluminescent device according to the present invention.

[0023] Figure 4 This is one aspect of the invention.

[0024] 100, 200, 300: Organic electronic components; 110: First electrode

[0025] 120: Hole injection layer; 130: Hole transport layer

[0026] 140: Emissive layer; 150: Electron transport layer

[0027] 160: Electron injection layer; 170: Second electrode

[0028] 180: Light efficiency enhancement layer; 210: Buffer layer

[0029] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0030] 330: First hole transport layer; 340: First luminescent layer

[0031] 350: First electron transport layer; 360: First charge generation layer

[0032] 361: Second charge generation layer; 420: Second hole injection layer

[0033] 430: Second hole transport layer; 440: Second luminescent layer

[0034] 450: Second electron transport layer; CGL: Charge generation layer

[0035] ST1: First stack; ST2: Second stack Detailed Implementation

[0036] 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 may render the subject matter of the invention rather unclear, and such descriptions will be omitted.

[0037] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b), etc., may be used herein. Each of these terms is not intended to define the nature, order, or sequence of the respective components, but merely 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 linked to the other component, but the other component may be “connected,” “linked,” or “attached” between the various components.

[0038] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0039] Unless otherwise stated, the term “halogen” or “halogen” as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0040] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein refers to a single bond having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms, or 1 to 10 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.

[0041] Unless otherwise stated, the term "alkenyl" or "alkynyl" as used herein refers to, but is not limited to, a double or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, 2 to 12 carbon atoms, or 2 to 10 carbon atoms, and includes straight or branched groups.

[0042] Unless otherwise stated, the term "cycloalkyl" as used herein refers to, but is not limited to, an alkyl group forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 3 to 10 carbon atoms.

[0043] Unless otherwise stated, the terms “alkoxy group”, “alkoxy group” or “alkyloxy” as used herein refer to, but are not limited to, an alkyl group bonded to an alkyl group and having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms or 1 to 10 carbon atoms.

[0044] Unless otherwise stated, the term "aryloxy group" or "aryloxy group" as used herein refers to, but is not limited to, an aryl group bonded to an oxygen group, and has 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms.

[0045] Unless otherwise stated, the terms "aryl group" and "arylene group" as used in this invention refer to groups having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms, but are not limited thereto. In this invention, an aryl group or arylene group refers to an aromatic group with a single ring or multiple rings, and includes aromatic rings formed by bonding or reaction of adjacent substituents. For example, an aryl group can be a phenyl, biphenyl, fluorene, or spirofluorene group.

[0046] The prefix "aryl" or "aromatic" refers to a group substituted with an aryl group. For example, aralkyl can be an alkyl group substituted with an aryl group, and arylenyl can be an alkenyl group substituted with an aryl group, and the aryl-substituted group has the number of carbon atoms as defined herein. Furthermore, when prefixes are named sequentially, this means that the substituents are listed in the order described first. For example, arylalkoxy refers to an alkoxy group substituted with an aryl group, alkoxycarbonyl refers to a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also refers to an alkenyl group substituted with an arylcarbonyl group, wherein the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0047] Unless otherwise stated, the term "heterocyclic group" as used herein contains one or more heteroatoms and has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, 2 to 16 carbon atoms, or 2 to 12 carbon atoms, and includes any of a single ring or multiple rings, and may include heteroaliphatic rings and heteroaromatic rings. Furthermore, heterocyclic groups may also be formed together with adjacent groups.

[0048] Unless otherwise stated, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0049] Furthermore, "heterocyclic rings" can include rings containing SO2 instead of carbon atoms. For example, "heterocyclic rings" include the following compounds.

[0050]

[0051] Unless otherwise stated, the terms “fluorenyl group”, “fluoreneyl group”, as used herein refer to a monovalent, divalent, or trivalent functional group, wherein R, R', and R'' are all hydrogen in the following structures, and the terms “substituted fluorenyl group”, “substituted fluoreneyl group”, or “substituted fluorentriyl 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 spirocyclic compound together with the carbon to which they are bonded.

[0052]

[0053] The term "spirocyclic compound" used in this invention refers to a "spiro union," which is a connection formed by two rings sharing only one atom. The atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms in the compound, they are referred to as "single-spiro" compounds, "two-spiro" compounds, and "triple-spiro" compounds, respectively.

[0054] Unless otherwise stated, the term "aliphatic" as used herein refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms, or 1 to 10 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 3 to 10 carbon atoms.

[0055] Unless otherwise stated, the term "ring" as used herein refers to an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 3 to 10 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heterocycle having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, 2 to 14 carbon atoms, 2 to 12 carbon atoms, or 2 to 10 carbon atoms, or a fused ring formed by combinations thereof, and includes saturated or unsaturated rings.

[0056] Other hetero compounds or heterogroups besides those mentioned above include one or more heteroatoms, but are not limited thereto.

[0057] Furthermore, unless otherwise stated, the term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from: deuterium, halogen, amino group, nitrile group, nitro group, C1-C20 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 groups, silyl groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not limited to these substituents.

[0058] Furthermore, unless otherwise explicitly explained, the formulas used in this invention are the same as the substituents defined by exponentiation in the following formulas.

[0059]

[0060] 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, it is attached to any of the carbon atoms that make up the benzene ring, and the combinations are 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 bonds to the carbons of the benzene ring in a similar manner, while omitting the hydrogens that indicate the bonds to the carbons forming the benzene ring.

[0061]

[0062] The term "composition" as used in this invention is intended to be interpreted broadly to include not only compounds but also solutions, dispersions, and mixtures and blends of liquids and solids.

[0063] The compositions of the present invention may contain only the compounds of the present invention, or the compounds may be contained in a combination of two or more different compounds, or the compounds may be contained in a combination of two or more other compounds. That is, the compositions may include only compounds corresponding to Formula 1, mixtures of two or more compounds of Formula 1, and mixtures of compounds of Formula 1 with compounds that do not correspond to the present invention. Here, compounds that do not correspond to the present invention may be a single compound or two or more compounds. In this case, if the compounds are contained in a combination of two or more compounds with other compounds, the other compounds may be known compounds of each organic material layer or compounds to be developed in the future. In this case, the compounds contained in the organic material layer may consist only of homogeneous compounds, but may also be mixtures of two or more heterogeneous compounds represented by Formula 1.

[0064] In the following, an organic electronic component according to one aspect of the present invention will be described.

[0065] The present invention provides compounds represented by Formula 1.

[0066]

[0067] in: X and Y are independently O or S. Z represents O, S, C(R) a (R) b ) or Si(R c (R) d ), R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d Independently identical or different from each other, and independently selected from: hydrogen; deuterium; cyano group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom selected from O, N, S, Si and P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C3-C 60 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 An aryloxy group; or multiple adjacent groups thereof may bond together to form a ring. Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 aryl group, C6-C 18 aryl group or C6-C 12 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0068] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0069] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a Rb R d and R d When it is a fused ring group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, and more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0070] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d When it is an aliphatic ring, C3-C is preferred. 30 Aliphatic rings, more preferably C3-C 25 Aliphatic ring, C3-C 18 Aliphatic ring or C3-C 12 Aliphatic rings.

[0071] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d When the group is an alkyl group, C1-C is preferred. 30 Alkyl groups, more preferably C1-C 25 Alkyl groups, C1-C 18 alkyl groups or C1-C 12 Alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, etc.

[0072] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and Rd When the group is an alkoxy group, C1-C is preferred. 25 Alkoxy groups, more preferably C1-C 18 alkoxy groups, C1-C 12 Alkoxy group.

[0073] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d When the group is an aryloxy group, C6-C is preferred. 25 aryloxy groups, more preferably C6-C 18 aryloxy group, C6-C 12 Aryloxy group.

[0074] L 1 Independently selected from: single bond; C6-C 60 arylene group; fluorene group; C2-C group containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; Where L 1 When the group is arylene, C6-C is preferred. 30 aryl groups, more preferably C6-C 25 arylene group, C6-C 18 arylene group or C6-C 12 Aromatic groups, such as phenylene, biphenylene, naphthylene, terphenylene, anthraceneylene, phenanthrene, etc.

[0075] Where L 1 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0076] Ar 1It is the substituent represented by formula 1-1. a, e, and h are independent integers from 0 to 4, b and d are independent integers from 0 to 2, c and f are independent integers from 0 to 5, and g is an integer from 0 to 3. Indicates the bonding location.

[0077] The aryl group, arylene group, heterocyclic group, fluorenyl group, fluorene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be substituted by one or more substituents selected from the following: deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; 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 Aryl groups; and C8-C 20 The substituents are aryl groups; and the hydrogen atoms of these substituents may be further replaced by one or more deuterium atoms, or these substituents may bond to each other to form saturated or unsaturated rings, wherein the term "ring" refers to a C3-C ring. 60 Aliphatic ring or C6-C 60 Aroma rings or C2-C 60 Heterocyclic groups or fused rings formed by their combination.

[0078] Furthermore, Equation 1-1 is any one of Equations 1-1-a to 1-1-d.

[0079]

[0080] in: Z, R 7 R 8 , g, h and Same as defined in Equation 1-1.

[0081] Formula 1-1 is preferably any one of Formula 1-1-1 to Formula 1-1-16.

[0082]

[0083] in: R7, R8, g, h and Same as defined in Equation 1-1, R' and R'' are C1-C molecules that are independently substituted or unsubstituted with deuterium. 10 Alkyl groups; or C6-C groups that are substituted with or unsubstituted with deuterium. 20 Aryl groups; or R' and R'' can bond to each other to form a spirocycle. In addition, L 1 It can be represented by a single bond or any one of formulas L-1 to L-27.

[0084]

[0085] in: W represents O, S, C(R) 19 (R) 20 ) or N-Ar 2 , R 9 R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 10 R 11 and R 12 R in Equation 1 1 The definitions are the same, or their adjacent groups can bond with each other to form a ring. Ar 2 It is C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom selected from O, N, S, Si and P. 60 Heterocyclic groups; C1-C 50 alkyl groups; and C2-C 20 alkenyl groups; Among them, when Ar 2 When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0086] Among them, when Ar 2 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 24Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0087] Among them, when Ar 2 When the group is an alkyl group, C1-C is preferred. 30 Alkyl groups, more preferably C1-C 24 alkyl groups, i, k, m, n, o, and p are independent integers from 0 to 4, j is an integer from 0 to 6, l is an integer from 0 to 2, q is an integer from 0 to 3, and r is an integer from 0 to 5. Indicates the bonding location.

[0088] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-120, but is not limited thereto.

[0089]

[0090] In another aspect, the present invention provides a method for reusing a compound of formula 1, comprising: Crude organic light-emitting material containing a compound of formula 1 is recovered from a deposition apparatus used in a method for depositing organic light-emitting materials to prepare an organic light-emitting device; Remove impurities from crude organic light-emitting materials; Recycling organic light-emitting materials after removing impurities; and The recovered organic light-emitting materials are purified to a purity of 99.9% or higher.

[0091] The step of removing impurities from the crude organic light-emitting material recovered from the deposition equipment may preferably include a pre-purification process by recrystallization in a recrystallization solvent to obtain a purity of 98% or higher.

[0092] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0093] The recrystallization solvent can preferably be used by mixing a polar solvent having a polarity index of 5.5 to 7.2 with a nonpolar solvent having a polarity index of 2.0 to 4.7.

[0094] When using a mixture of polar and nonpolar solvents, the recrystallization solvent can be used such that the amount of nonpolar solvent is 15% (v / v) or less compared to the amount of polar solvent.

[0095] The recrystallization solvent is preferably a single solvent of N-methylpyrrolidone (NMP); a polar solvent selected from any one of 1,3-dimethyl-2-imidazolinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide mixed with N-methylpyrrolidone; or a single or mixed nonpolar solvent selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate and butanone; or a mixture of polar and nonpolar solvents.

[0096] The pre-purification process may include the step of precipitating crystals by dissolving crude organic light-emitting materials recovered from the deposition equipment in a polar solvent at 90°C to 120°C and then cooling to 0°C to 5°C.

[0097] The pre-purification process may include the steps of precipitating crystals by dissolving crude organic light-emitting materials recovered from the deposition equipment at 90°C to 120°C in a polar solvent, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C.

[0098] The pre-purification process may include steps such as dissolving the crude organic light-emitting material recovered from the deposition equipment in a nonpolar solvent, concentrating the solvent, removing the nonpolar solvent, and simultaneously precipitating crystals.

[0099] The pre-purification process may include steps such as recrystallization with a polar solvent followed by recrystallization with a non-polar solvent.

[0100] The step of purifying the recovered impurities to a purity of 99.9% or higher may include an adsorption separation process by adsorption on an adsorbent to adsorb and remove the impurities.

[0101] The adsorbent can be activated carbon, silica gel, alumina, or other materials used for known adsorption purposes.

[0102] The step of purifying the recovered impurities to a purity of 99.9% or higher may include sublimation purification.

[0103] Reference Figure 1 An organic electronic component (100) according to one embodiment of the present invention includes a first electrode (110), a second electrode (120), and an organic material layer between the first electrode (110) and the second electrode (170), said organic material layer comprising a single compound or two or more compounds represented by Formula 1. Here, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode, and in the case of an inverted organic electronic component, the first electrode may be a cathode and the second electrode may be an anode.

[0104] The organic material layer may sequentially 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) on the first electrode (110). Here, the layers other than the light-emitting layer (140) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc., can be used as a hole blocking layer (see...). Figure 2 ).

[0105] Furthermore, the organic electronic component according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer is formed on one of the two surfaces of the first electrode that is not in contact with the organic material layer, or on one of the two surfaces of the second electrode that is not in contact with the organic material layer.

[0106] The compound according to one embodiment of the present invention, applied to an organic material layer, can be used as a host, dopant, or light efficiency enhancement layer material for a hole injection layer (120), a hole transport layer (130), a light-emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), and a light-emitting layer (140). Preferably, for example, the compound of formula 1 according to the present invention can be used as a light-emitting auxiliary layer material.

[0107] The organic material layer may include two or more stacks, each stack comprising a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on an anode, and the organic material layer may further include a charge-generating layer formed between the two or more stacks (see [link to documentation]). Figure 3 ).

[0108] In addition, even when using the same core, band gap, electrical properties, interface properties, etc. may vary depending on which substituent is bonded to which position. Therefore, the choice of the combination of the core and its associated secondary substituents is also very important. In particular, when the optimal combination of energy level and T1 value and the unique properties of each organic material layer (mobility, interface properties, etc.) are achieved, long lifetime and high efficiency can be achieved simultaneously.

[0109] The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or alloy thereof is deposited on a substrate to form an anode, and an organic material layer 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) is formed thereon, and then a material that can be used as a cathode is deposited thereon.

[0110] Furthermore, the present invention provides an organic electronic component in which an organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process, and the organic material layer contains the compound as an electron transport material.

[0111] As another specific example, the same or different types of compounds represented by Formula 1 are mixed and used in an organic material layer.

[0112] Furthermore, the present invention provides a composition for a light-emitting auxiliary layer comprising a compound represented by Formula 1, and an organic electronic device comprising the light-emitting auxiliary layer.

[0113] Furthermore, the present invention also provides an electronic device comprising a display device and a control unit for driving the display device, the display device comprising the organic electronic components.

[0114] According to another aspect, the present invention provides a display device in which the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochrome or white illumination. Here, the electronic device can be a currently used or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals (e.g., cellular phones), personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP) devices, remote controls, navigation units, game consoles, various types of TVs, and various types of computers.

[0115] In the following, examples of the synthesis of compounds represented by Formula 1 of the present invention and examples of the preparation of organic electronic components of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0116] [Synthesis example]

[0117] The compound (final product) represented by Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in reaction scheme 1, but is not limited thereto.

[0118] <Reaction Scheme 1>

[0119] Where: R 1 R 2 R 3 R 4 R 5 R 6 a, b, c, d, e, f, Ar 1 and L 1 It is the same as defined in Equation 1, and Hal is Br or Cl.

[0120] I. Synthesis of the final product

[0121] 1. Example of P-3 synthesis

[0122] 1-Chloro-4-phenyldibenzo[b,d]furan (20.0 g, 71.8 mmol) was dissolved in toluene (240 mL) in a round-bottom flask. N-(dibenzo[b,d]furan-3-yl)-4-phenyldibenzo[b,d]furan-1-amine (33.6 g, 78.9 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), 50% P(t-Bu)3 (1.7 mL, 4.4 mmol), and NaOt-Bu (13.8 g, 143.5 mmol) were added, and the mixture was stirred at 110 °C. After the reaction was complete, the mixture was extracted with an organic solvent and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was subjected to column chromatography and recrystallization to obtain the product (35.0 g, yield: 73%).

[0123] 2. Example of P-10 synthesis

[0124] Sub 1-1 (25.0 g, 89.7 mmol), Sub 2-10 (43.6 g, 98.7 mmol), Pd2(dba)3 (2.5 g, 2.7 mmol), 50% P(t-Bu)3 (2.2 ml, 5.4 mmol), and NaOt-Bu (17.2 g, 179.4 mmol) were placed in a round-bottom flask, and the product (42.3 g, yield: 69%) was obtained using the P-3 synthesis method.

[0125] 3. Example of P-25 synthesis

[0126] Sub 1-1 (23.0 g, 82.5 mmol), Sub 2-17 (41.0 g, 90.8 mmol), Pd2(dba)3 (2.3 g, 2.5 mmol), 50% P(t-Bu)3 (2.0 ml, 5.0 mmol), and NaOt-Bu (15.9 g, 165.0 mmol) were placed in a round-bottom flask, and the product (40.6 g, yield: 71%) was obtained using the P-3 synthesis method.

[0127] 4. Example of P-35 synthesis

[0128] Sub 1-2 (18.0 g, 61.1 mmol), Sub 2-23 (30.7 g, 67.2 mmol), Pd2(dba)3 (1.7 g, 1.8 mmol), 50% P(t-Bu)3 (1.5 ml, 3.7 mmol), and NaOt-Bu (11.7 g, 122.1 mmol) were placed in a round-bottom flask, and the product (34.1 g, yield: 78%) was obtained using the P-3 synthesis method.

[0129] 5. Synthesis example of P-42

[0130] Sub 1-1 (20.0 g, 71.8 mmol), Sub 2-34 (45.4 g, 78.9 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), 50% P(t-Bu)3 (1.8 ml, 4.4 mmol), and NaOt-Bu (13.8 g, 143.5 mmol) were placed in a round-bottom flask, and the product (49.9 g, yield: 85%) was obtained using the P-3 synthesis method.

[0131] 6. Example of P-55 synthesis

[0132] Sub 1-2 (10.0 g, 33.9 mmol), Sub 2-43 (18.0 g, 37.3 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), 50% P(t-Bu)3 (0.8 ml, 2.0 mmol), and NaOt-Bu (6.5 g, 67.8 mmol) were placed in a round-bottom flask, and the product (19.1 g, yield: 76%) was obtained using the P-3 synthesis method.

[0133] 7. Example of P-68 synthesis

[0134] Sub 1-2 (12.0 g, 40.7 mmol), Sub 2-52 (27.2 g, 44.8 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), 50% P(t-Bu)3 (1.0 ml, 2.4 mmol), and NaOt-Bu (7.8 g, 81.4 mmol) were placed in a round-bottom flask, and the product (23.3 g, yield: 66%) was obtained using the P-3 synthesis method.

[0135] 8. Synthesis example of P-79

[0136] 1) Synthesis of Sub 2-59-1

[0137] In a round-bottom flask, 2-bromoaniline (60.0 g, 348.8 mmol) was dissolved in THF (900 mL), followed by the addition of 4-dibenzofuranboronic acid (88.7 g, 418.5 mmol), Pd(PPh3)4 (12.1 g, 10.5 mmol), NaOH (41.9 g, 1046.3 mmol), and water (300 mL). The mixture was stirred at 75 °C. After the reaction was complete, the mixture was extracted with an organic solvent and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was subjected to column chromatography and recrystallization to obtain the product (74.2 g, yield: 82%).

[0138] 2) Synthesis of Sub 2-59

[0139] Sub 2-59-1 (26.4 g, 101.8 mmol), Sub 1-2 (30.0 g, 101.8 mmol), Pd2(dba)3 (2.8 g, 3.1 mmol), 50% P(t-Bu)3 (2.5 ml, 6.2 mmol), and NaOt-Bu (19.6 g, 203.5 mmol) were placed in a round-bottom flask, and the product (69.6 g, yield: 79%) was obtained using the P-3 synthesis method.

[0140] 3) Synthesis of P-79

[0141] Sub 2-59 (20.9 g, 40.4 mmol), Sub 1-4 (15.0 g, 40.4 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), 50% P(t-Bu)3 (1.0 ml, 2.4 mmol), and NaOt-Bu (7.8 g, 80.9 mmol) were placed in a round-bottom flask, and the product (23.8 g, yield: 68%) was obtained using the P-3 synthesis method.

[0142] 9. Example of P-110 synthesis

[0143] 1) Synthesis of Sub 2-81

[0144] Sub 1-8 (30.0 g, 100.1 mmol), 3-(9,9-diphenyl-9H-fluorene-2-yl)aniline (41.0 g, 100.1 mmol), Pd2(dba)3 (2.8 g, 3.0 mmol), 50% P(t-Bu)3 (2.4 ml, 6.0 mmol), and NaOt-Bu (19.2 g, 200.1 mmol) were placed in a round-bottom flask to obtain the product (55.2 g, yield: 49.3%) using the synthesis method of P-3.

[0145] 2) Synthesis of P-110

[0146] Sub 2-81 (33.2 g, 49.3 mmol), Sub 1-16 (20.0 g, 49.3 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), 50% P(t-Bu)3 (1.2 ml, 3.0 mmol), and NaOt-Bu (9.5 g, 98.8 mmol) were placed in a round-bottom flask, and the product (38 g, yield: 74%) was obtained using the P-3 synthesis method.

[0147] Sub 1 of reaction scheme 1 can be, but is not limited to, the compounds shown below, and the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 1 are shown in Table 1.

[0148]

[0149] [Table 1]

[0150] Sub 2 of reaction scheme 1 can be, but is not limited to, the following compounds, and the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 2 are shown in Table 2.

[0151]

[0152] [Table 2]

[0153] The FD-MS (field desorption-mass spectrometry) values ​​of compounds P-1 to P-120 of the present invention prepared according to the above synthesis examples are shown in Table 3.

[0154] [Table 3]

[0155] Meanwhile, exemplary synthetic examples of the present invention represented by Formula 1 have been described, but these are all based on the Buchwald-Hartwig cross-coupling reaction, the Miyaura borylation reaction, the Suzuki cross-coupling reaction, and intramolecular acid-induced cyclization reactions ( J. mater. Chem. 1999, 9, 2095. Pd(II)-catalyzed oxidative cyclization reaction Org. Lett. 2011, 13, 5504 ) and PPh3-mediated reductive cyclization reaction ( J. Org. Chem. 2005, 70, 5014. Furthermore, those skilled in the art will readily understand that the reaction proceeds even with substituents other than those specified in the specific synthetic example as defined in Bond Formula 1.

[0156] Manufacturing and evaluation of organic electroluminescent devices

[0157] [Example 1] Red organic electroluminescent device (light-emitting auxiliary layer)

[0158] Compound A and Compound B were used on an ITO layer (anode) formed on a glass substrate, with Compound B being doped at a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm. Then, Compound A was vacuum deposited on the hole injection layer with a thickness of 110 nm to form a hole transport layer.

[0159] Next, a light-emitting auxiliary layer is formed by vacuum depositing the compound P-1 of the present invention to a thickness of 10 nm on the hole transport layer. Subsequently, using compound DR as the host material of the light-emitting layer and bis(1-phenylisoquinolinyl)iridium(III)acetylacetonate (hereinafter referred to as "(piq)2Ir(acac)") as the dopant material, and said dopant is doped such that the weight ratio of host to dopant is 95:5, to form a light-emitting layer with a thickness of 30 nm.

[0160] Next, a hole-blocking layer with a thickness of 10 nm was formed by vacuum deposition of compound E on the light-emitting layer, and an electron transport layer with a thickness of 30 nm was formed on the hole-blocking layer using a mixture of compound F and compound G mixed in a 5:5 weight ratio. Subsequently, compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0161] Compound A: N -([1,1'-biphenyl]-4-yl)-9,9-dimethyl- N -(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9 H -fluorene-2-amine

[0162] Compound B: 4,4',4''-((1 E ,1' E ,1'' E )-Cyclopropane-1,2,3-trimethyltri(cyanomethylene))tri(2,3,5,6-tetrafluorobenzonitrile)

[0163] Compound DR: 14-(4-phenylquinazolin-2-yl)-14 H -benzo[ c ]benzo[4,5]thieno[2,3- a ] carbazole

[0164] Compound E: 2-(4'-(9,9-dimethyl-9 H -fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0165] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0166] Compound G: (8-hydroxyquinoline)lithium

[0167] Example 2 to Example 20

[0168] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention listed in Table 4 were used instead of compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0169] [Comparative Example 1] and [Comparative Example 2]

[0170] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A or comparative compound B was used instead of compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0171]

[0172] Electroluminescence (EL) characteristics were measured using a PR-650 from PhotoResearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 20 and Comparative Examples 1 and 2 of the present invention, and a lifetime measurement device manufactured by Maxscience was used at 2500 cd / m². 2 The standard brightness measurement T95 lifetime is used. Table 4 shows the results of device manufacturing and evaluation.

[0173] Under the same conditions, the measuring equipment can evaluate the performance of a new material compared to a comparative compound, without being affected by possible daily fluctuations in deposition rate, vacuum quality, or other parameters.

[0174] During the evaluation process, each batch contained four identically prepared OLEDs containing the comparison compound, and since the performance of a total of 12 OLEDs from three batches was evaluated separately, the experimental results obtained in this manner showed statistical significance.

[0175] [Table 4]

[0176] As can be seen from the results in Table 4, when a red organic electroluminescent device is manufactured using materials for organic electroluminescent devices, it can be confirmed that, compared with the comparative examples using comparative compound A or comparative compound B as the luminescent auxiliary layer, the driving voltage, lifetime, and luminous efficiency of the organic electroluminescent device are significantly improved in the examples using the compounds of the present invention. Comparative compound A or comparative compound B is similar to the compounds of the present invention in that it is a tertiary amine compound, wherein 1-dibenzofuran or 1-dibenzothiophene is disubstituted at the 4-position of the molecule, but differs in that it does not have a 3-fused ring represented by Formula 1-1 as a substituent as in the compounds of the present invention.

[0177] To examine the effect of the compositional differences of these compounds, data for the comparative compounds and the compounds of the present invention, measured using the DFT method (B3LYP / 6-31g(D)) with a Gaussian procedure, are shown in Table 5.

[0178] [Table 5]

[0179] The results in the table confirm that the HOMO value of the compound of the present invention is shallower than the HOMO energy level (hereinafter referred to as HOMO) values ​​of comparative compound A and comparative compound B. Therefore, it is believed that when the compound of the present invention is applied to a device, hole injection and hole transfer from the hole transport layer to the light-emitting auxiliary layer become easier than with the comparative compounds, thereby reducing hole accumulation in the hole transport region. This, in turn, reduces the driving voltage of the device and improves the charge balance of the light-emitting layer, resulting in increased efficiency. Furthermore, in the case of the LUMO energy level (hereinafter referred to as LUMO), the compound of the present invention forms a shallower level than the comparative compounds. Therefore, when the compound of the present invention is applied to a device, electrons from the light-emitting layer can be effectively blocked compared to the comparative compounds, thus confirming a significantly improved device lifetime.

[0180] That is, as can be seen from the results in Tables 4 and 5, it can be confirmed that, compared with comparative compound A or comparative compound B, which have a similar composition to the compounds of the present invention, the compounds satisfying all the structural features and compositions disclosed in the present invention exhibit significant effects in organic electronic devices. This indicates that the compounds of the present invention satisfying all specific compositions exhibit significant effects compared with other comparative compounds not described in this specification.

[0181] These results indicate that even with similar molecular components, the properties of compounds, such as hole characteristics, light efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density and intermolecular distance, can differ significantly to some extent. This difference is difficult to predict and depends on the type and position of the substituents. Furthermore, the performance of the devices varies not only due to a single component but also due to complex factors.

[0182] In the case of a light-emitting auxiliary layer, the relationship between the hole transport layer and the light-emitting layer (the main body) must be understood; therefore, even with similar cores, it is difficult for those skilled in the art to deduce the characteristics exhibited by the light-emitting auxiliary layer using the compounds of the present invention.

[0183] Furthermore, although the evaluation results of the above-mentioned device manufacturing explain the device characteristics when the compound of the present invention is applied only to the light-emitting auxiliary layer, the compound of the present invention can be applied to the hole transport layer or to both the hole transport layer and the light-emitting auxiliary layer.

[0184] Although 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 technical ideas of the invention, and the scope of the invention is not limited to the described embodiments. The scope of the invention should be interpreted based on the appended claims, and should be construed as including all technical ideas within the scope of the claims' equivalents.

[0185] [Industrial Applicability]

[0186] According to the present invention, organic devices with excellent device characteristics (e.g., high brightness, high luminescence, and long lifespan) can be manufactured, thus demonstrating industrial applicability.

Claims

1. Compounds represented by Formula 1: in: X and Y are independently O or S. Z is O, S, C(R a )(R b ) or Si(R c )(R d ), R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R a R b R d and R d Independently identical or different from each other, and independently selected from: hydrogen; deuterium; cyano group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom selected from O, N, S, Si and P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C3-C 60 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 An aryloxy group; or multiple adjacent groups thereof may bond together to form a ring. L 1 Independently selected from: single bond; C6-C 60 arylene group; fluorene group; C2-C group containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; Ar 1 It is the substituent represented by formula 1-1. a, e, and h are independent integers from 0 to 4, b and d are independent integers from 0 to 2, c and f are independent integers from 0 to 5, and g is an integer from 0 to 3. Indicates the bonding location, The aryl group, the arylene group, the heterocyclic group, the fluorene group, the fluorene group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, and the aryloxy group may be substituted by one or more substituents selected from the following: deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; 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 Aryl groups; and C8-C 20 The aromatic alkyl group; and the hydrogens of these substituents may be further substituted with one or more deuteriums, or these substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" refers to a C3-C ring. 60 Aliphatic ring or C6-C 60 Aroma rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof.

2. The compound according to claim 1, wherein formula 1-1 is represented by any one of formulas 1-1-a to 1-1-d: in: Z, R 7 R 8 , g, h and Same as defined in claim 1.

3. The compound according to claim 1, wherein L 1 Represented by a single bond or any of the formulas L-1 to L-27: in: W is O, S, C(R 19 )(R 20 ) or N-Ar 2 , R 9 R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 10 R 11 and R 12 With claim 1, R 1 The definitions are the same. Ar 2 It is C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom selected from O, N, S, Si and P. 60 Heterocyclic groups; C1-C 50 alkyl groups; and C2-C 20 alkenyl groups; i, k, m, n, o, and p are independent integers from 0 to 4, j is an integer from 0 to 6, l is an integer from 0 to 2, q is an integer from 0 to 3, and r is an integer from 0 to 5. Indicates the bonding location.

4. The compound according to claim 1, wherein the compound represented by formula 1 is any one of compounds P-1 to P-120: 。 5. An organic electronic component comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode; wherein the organic material layer comprises a single compound or two or more compounds represented by Formula 1 according to claim 1.

6. The organic electronic component according to claim 5, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

7. The organic electronic component according to claim 5, wherein the organic material layer is a light-emitting auxiliary layer.

8. The organic electronic component of claim 5, further comprising a light efficiency enhancement layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

9. The organic electronic component of claim 5, 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 an anode.

10. The organic electronic component of claim 9, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacked bodies.

11. An electronic device, comprising a display device and a control unit for driving the display device, the display device comprising the organic electronic element of claim 5.

12. The electronic device of claim 11, 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.

13. A method for reusing the compound represented by Formula 1 according to claim 1, comprising: Crude organic light-emitting material comprising the compound represented by Formula 1 of claim 1 is recovered from a deposition apparatus used in a method for depositing organic light-emitting material to prepare an organic light-emitting device; Remove impurities from the crude organic photoluminescent material; The organic light-emitting material after the impurities have been removed is recycled; as well as The recovered organic light-emitting material is purified to a purity of 99.9% or higher.

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