Compound for organic electronic element, organic electronic element using same, and electronic device therefor

Abstract

The present invention provides: a novel compound capable of improving the luminous efficiency, stability, and lifespan of an element; an organic electronic element using the compound; the invention also provides an electronic device.

Description

Technical Field

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

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

[0003] Materials used as organic material layers in organic electronic elements can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Light-emitting materials can be classified into high molecular weight types and low molecular weight types according to molecular weight, and according to the light-emitting mechanism, light-emitting materials can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons. In addition, light-emitting materials can be classified into blue-emitting materials, green-emitting materials, and red-emitting materials according to emission colors, as well as yellow-emitting materials and orange-emitting materials necessary to achieve more natural colors.

[0004] However, when only one material is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and there is a problem of reduced color purity or reduced device efficiency due to the emission attenuation effect. Therefore, in order to increase color purity and increase luminous efficiency through energy transfer, a host / dopant system can be used as a light-emitting material. The principle is that when a small amount of a dopant having a smaller band gap than the band gap of the host forming the emission layer is mixed in the emission layer, the excitons generated in the emission layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light with a desired wavelength can be obtained according to the type of dopant used.

[0005] Currently, the portable display market is large displays, and their size is increasing day by day, therefore, more power consumption is required than that required by existing portable displays. Therefore, for portable displays with limited power supply such as batteries, power consumption becomes a very important factor, and the issues of efficiency and service life must also be addressed.

[0006] Efficiency, service life and driving voltage are related to each other, and when efficiency increases, driving voltage is relatively reduced, and as driving voltage decreases, the crystallization of organic materials caused by Joule heating generated during driving decreases, and thus service life tends to increase. However, efficiency cannot be maximized simply by improving the organic material layer. This is because when the energy level and T1 value between each organic material layer and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined, long service life and high efficiency can be achieved at the same time.

[0007] Therefore, while delaying the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the reasons for shortening the service life of organic electronic components, it should have stable characteristics against Joule heating generated during device driving, and OLED devices are mainly formed by a deposition method, and it is necessary to develop materials that can withstand long-term deposition, that is, materials with strong heat resistance.

[0008] That is, in order to fully demonstrate the excellent characteristics of organic electronic components, priority should be given to materials that are stable and effective as materials for the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. However, the development of stable and effective organic material layer materials for organic electronic components has not been fully realized. Therefore, there is a continuous need to develop new materials, and in particular, there is an urgent need to develop host materials for the emission layer. Summary of the invention

[0009] In order to solve the above-mentioned problems of the background art, the present invention discloses a compound having a novel structure, and when the compound is applied to an organic electronic element, it has been found that the luminous efficiency, stability and service life of the device can be significantly improved.

[0010] Therefore, an object of the present invention is to provide a novel compound, an organic electronic element using the compound, and an electronic device thereof.

[0011] [Technical solution]

[0012] The present invention provides a compound represented by Formula 1.

[0013] <Formula 1>

[0014]

[0015] In another aspect, the present invention provides an organic electric element and an electronic device including the compound represented by Formula 1.

[0016] [Effects of the invention]

[0017] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and service life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention. DETAILED DESCRIPTION

[0019] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when a detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0020] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. It should be noted that if a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected", "coupled" or "connected" between the components.

[0021] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0022] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0023] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0024] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0025] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0026] Unless otherwise specified, the term “alkoxy group,” “alkoxy group,” or “alkyloxy group” as used herein means an alkyl group bonded to an oxy group and has 1 to 60 carbon atoms, but is not limited thereto.

[0027] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means an aryl group bonded to an oxy group and has 6 to 60 carbon atoms, but is not limited thereto.

[0028] Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, but are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by connecting or reacting adjacent substituents.

[0029] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0030] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0031] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0032] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any of a monocyclic and polycyclic ring, and may include a heteroaliphatic ring and a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0033] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0034] In addition, the term "heterocyclic group" may include SO 2 A ring that replaces a carbon that constitutes the ring.

[0035] For example, the "heterocyclic group" includes the following compounds.

[0036]

[0037] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0038]

[0039] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to the number of spiro atoms in the compound.

[0040] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0041] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0042] In addition to the above mentioned hetero compounds, other hetero compounds or hetero groups contain but are not limited to one or more hetero atoms.

[0043] In addition, unless otherwise specified, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, C 1 -C 20 Alkylamine group, C 1 -C 20 Alkylthiophene group, C 6 -C 20 Arylthiophene group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 3 -C 20 Cycloalkyl groups, C6 -C 20 Aryl groups, deuterated C 6 -C 20 Aryl group, C 8 -C 20 Arylene groups, silane groups, boron groups, germanium groups and C 2 -C 20 Heterocyclic groups, but are not limited to these substituents.

[0044] In addition, unless otherwise specifically explained, the formulae used in the present invention are the same as the definitions of substituents by the following exponent definitions of the formulae.

[0045]

[0046] Here, when a is an integer of 0, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 Connected to any one of the carbon atoms constituting the benzene ring, when a is an integer of 2 or 3, each is combined as follows, wherein R 1 may be the same as or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, but indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

[0047]

[0048] Reorganization energy refers to the energy lost due to changes in the molecular structure arrangement during the movement of charges (electrons, holes). It depends on the molecular geometry and has the characteristic that the value becomes smaller as the difference between the PES (potential energy surface) in the neutral state and the PES in the charged state becomes smaller. The RE value can be obtained by the following formula.

[0049] RE 空穴 :λ + =(E NOCE -E COCE )+(E CONE -E NONE )

[0050] RE 电子 :λ - =(E NOAE -E AOAE )+(E AONE -E NONE )

[0051] Each factor is described as NONE: neutral geometry of neutral molecules (=NO opt.), NOAE: anionic geometry of neutral molecules, NOCE: cationic geometry of neutral molecules, AONE: neutral geometry of anionic molecules, AOAE: anionic geometry of anionic molecules (=AO opt.), CONE: neutral geometry of cationic molecules, COCE: cationic geometry of cationic molecules (=CO opt.).

[0052] The value of reorganization energy is inversely proportional to the mobility, and under the condition that they have the same r and T values, the RE value of each material directly affects the mobility. The relationship between the RE value and the mobility is expressed as follows.

[0053]

[0054]

[0055] Each factor is described as λ: reorganization energy / μ: mobility / r: dimer displacement / t: intermolecular charge transfer matrix element. According to the above equations, the lower the RE value, the faster the mobility.

[0056] The reorganization energy value requires a simulation tool that can calculate potential energy based on the molecular structure, and we use Gaussian09 (hereinafter, G09) and Jaguar module (hereinafter, JG) of SchrodingerMaterials Science. Both G09 and JG are tools for analyzing molecular properties through quantum mechanics (QM) calculations, and have the function of optimizing molecular structures or calculating the energy (single point energy) of a given molecular structure.

[0057] The process of performing QM calculations of molecular structures requires a large amount of computing resources, and our company uses 2 cluster servers to perform these calculations. Each cluster server consists of 4 node workstations and 1 master workstation, and each node performs molecular QM calculations through symmetric multi-processing (SMP) parallel computing using a CPU with more than 36 cores.

[0058] G09 was used to calculate the potential energy in the neutral state / charged state (NONE / COCE) required for the optimized molecular structure and its rearrangement energy. The charged potential energy (NOCE) of the structure optimized for the neutral state and the neutral potential energy (CONE) of the structure optimized for the charged state were calculated by charging only the charge to the two optimized structures. Thereafter, the rearrangement energy was calculated according to the following relationship.

[0059] RE 电荷 :λ=(ENOCE -E COCE )+(E CONE -E NONE )

[0060] Since Schrodinger provides a function of automatically performing such a calculation process, the potential energy according to each state is calculated in sequence through the JG module by providing the molecular structure (NO) of the ground state, and the RE value is calculated.

[0061] Hereinafter, a compound according to aspects of the present invention and an organic electric element including the compound will be described.

[0062] The present invention provides a compound represented by Formula 1.

[0063] <Formula 1>

[0064]

[0065] in:

[0066] Ar 1 is a substituent represented by formula 1-A; or a substituent represented by formula 1-B;

[0067]

[0068] Ar 2 is a substituent represented by formula 1-C; or a substituent represented by formula 1-D;

[0069]

[0070] Ar 3 and Ar 4 Each independently is C 6 -C 60 an aryl group; or a C 2 -C 60 Heterocyclic groups;

[0071] When Ar 3 and Ar 4 When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 The aryl group, for example, can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, wait,

[0072] When Ar 3 and Ar 4 When it is a heterocyclic group, it may preferably be C 2 -C 30A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0073] R 1 and R 2 are the same or different and are each independently selected from hydrogen; or deuterium;

[0074] L 1 and L 2 Each is independently a single bond; C 6 -C 60 Arylene group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups;

[0075] When L 1 and L 2 When it is an arylene group, it may preferably be C 6 -C 30 Arylene groups, more preferably C 6 -C 25 Arylene groups, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracene, etc.,

[0076] When L 1 and L 2 When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0077] a is an integer from 0 to 6, b is an integer from 0 to 3,

[0078] In Formula 1-A to Formula 1-D,

[0079] R 3 are the same or different and are independently hydrogen; or deuterium;

[0080] D stands for deuterium,

[0081] c is an integer from 0 to 5, d is an integer from 0 to 7, e is an integer from 1 to 5, f is an integer from 1 to 7,

[0082] * means the position to be bonded,

[0083] wherein the aryl group, arylene group and heterocyclic group may be substituted by one or more substituents selected from deuterium; C 6 -C 20 Aryl group; and C substituted by deuterium 6 -C 20 Aryl groups;

[0084] In addition, Formula 1 is represented by any one of Formula 1-1 to Formula 1-4.

[0085]

[0086]

[0087] Among them, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 3 ,Ar 4 , a, b, c, d, e, f and D are the same as defined in Formula 1.

[0088] In addition, L 1 and L 2 At least one of is represented by any one of the following formulas a-1 to a-20.

[0089]

[0090] in:

[0091] R 6 are the same or different and are each independently deuterated; C 6 -C 20 Aryl group; and C substituted by deuterium 6 -C 20 Aryl groups;

[0092] g, h and i are each independently an integer from 0 to 4, j is an integer from 0 to 6, k is an integer from 0 to 8,

[0093] * Means bonded to triazine or Ar 3 or Ar 4 part.

[0094] In addition, Ar 3 and Ar 4At least one of is represented by any one of the following Formula b-1 to Formula b-12.

[0095]

[0096] in:

[0097] X is NR 8 , O or S,

[0098] R 7 are the same or different and are each independently deuterated; C 6 -C 20 Aryl group; and C substituted by deuterium 6 -C 20 Aryl groups;

[0099] R 8 It is C 6 -C 60 an aryl group; or a C 2 -C 60 Heterocyclic groups;

[0100] When R 8 When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 The aryl group, for example, can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, wait,

[0101] When R 8 When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0102] l is an integer from 0 to 5, m and o are each independently an integer from 0 to 7, n is an integer from 0 to 9,

[0103] Means to bind to L 1 or L 2 part.

[0104] Specifically, the compound represented by Formula 1 may be any one of the following Compound P-1 to Compound P-76, but is not limited thereto.

[0105]

[0106]

[0107]

[0108]

[0109] In another aspect, the present invention provides an organic electronic element, comprising a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a light-emitting layer, wherein the light-emitting layer is a phosphorescent light-emitting layer and comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 3 or Formula 4.

[0110]

[0111] in:

[0112] L 3 , L 4 , L 5 and L 6 are each independently selected from a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring-fused ring groups;

[0113] When L 3 , L 4 , L 5 and L 6 When it is an arylene group, it may preferably be C 6 -C 30 Arylene groups, more preferably C 6 -C 25 Arylene groups, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracene, etc.,

[0114] When L 3 , L 4 , L 5 and L 6 When it is a heterocyclic group, it may preferably be C 2 -C30 A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, etc.

[0115] When L 3 , L 4 , L 5 and L 6 When it is a fused ring group, it may preferably be C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused ring group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group,

[0116] Ar 5 ,Ar 6 and Ar 7 Each independently selected from C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring-fused ring groups;

[0117] When Ar 5 ,Ar 6 and Ar 7 When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0118] When Ar 5 ,Ar 6 and Ar 7 When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0119] When Ar 5 ,Ar 6 and Ar 7 When it is a fused ring group, it may preferably be C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused ring group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group.

[0120] Ar 8 Each independently selected from C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring fused ring group; and -L'-NR b R c ;

[0121] When Ar 8 When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0122] When Ar 8 When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0123] When Ar 8 When it is a fused ring group, it may preferably be C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused ring group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group.

[0124] Z is O, S, CR'R" or NR a ,

[0125] Ring A is C 6 -C 20 Aryl groups,

[0126] R 9 and R 10 are each independently the same or different and are each independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring fused ring group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 Alkoxy group; and C 6 -C 60 Aryloxy group; or multiple adjacent R 9 or multiple R 10 can be bonded to each other to form a ring,

[0127] When R 9 and R 10 When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0128] When R 9and R 10 When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0129] When R 9 and R 10 When it is a fused ring group, it may preferably be C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused ring group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group.

[0130] When R 9 and R 10 When it is an alkyl group, it may preferably be C 1 -C 30 An alkyl group, and more preferably a C 1 -C 24 Alkyl group.

[0131] When R 9 and R 10 When alkoxy groups are present, they may preferably be C 1 -C 30 Alkoxy groups, and more preferably C 1 -C 24 Alkoxy groups,

[0132] When R 9 and R 10 When it is an aryloxy group, it may preferably be C 6 -C 30 Aryloxy groups, more preferably C 6 -C 24 aryloxy,

[0133] p and q are each independently an integer from 0 to 4,

[0134] L' is each independently selected from a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C containing at least one heteroatom of O, N, S, Si or P2 -C 60 Heterocyclic group; and C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring-fused ring groups;

[0135] When L' is an arylene group, it may preferably be C 6 -C 30 Arylene groups, more preferably C 6 -C 25 Arylene groups, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracene, etc.,

[0136] When L' is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 20 Heterocyclic groups, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthiobenzothiophene, naphthiobenzofuran, benzofuran, benzothiophene, etc.,

[0137] When L' is an aliphatic group, they may preferably be C 3 -C 30 aliphatic group, more preferably C 3 -C 24 Aliphatic group.

[0138] R b and R c Each independently selected from C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 60 Heterocyclic group; C 3 -C 60 aliphatic ring;

[0139] When R b and R c When they are aliphatic groups, they may preferably be C 3 -C 30 aliphatic group, more preferably C 3 -C 24 Aliphatic group.

[0140] When R b and R c When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2-C 20 Heterocyclic groups, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthiobenzothiophene, naphthiobenzofuran, benzofuran, benzothiophene, etc.,

[0141] R' and R" are each independently selected from hydrogen; deuterium; C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring fused ring group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 Alkoxy group; and C 6 -C 60 aryloxy group; or R' and R" may be bonded to each other to form a ring,

[0142] When R' and R" are aryl groups, they may preferably be C 6 -C 30 An aryl group, and more preferably a C 6 -C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0143] When R' and R" are heterocyclic groups, they may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0144] When R' and R" are fused ring groups, they may preferably be C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused ring group, more preferably C 3 -C 24Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group.

[0145] When R' and R" are alkyl groups, they may preferably be C 1 -C 30 An alkyl group, and more preferably a C 1 -C 24 Alkyl group.

[0146] When R' and R" are alkoxy groups, they may preferably be C 1 -C 24 Alkoxy groups,

[0147] When R' and R" are aryloxy groups, they may preferably be C 6 -C 24 Aryloxy groups,

[0148] R a It is C 6 -C 60 an aryl group; or a C 2 -C 60 Heterocyclic groups;

[0149] When R a When it is an aryl group, it may preferably be C 6 -C 30 Aryl group, and more preferably C 6 -C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0150] When R a When it is a heterocyclic group, it may preferably be C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0151] wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 Aryl group; C substituted by deuterium 6 -C 20 Aryl group; Fluorenyl group; C 2 -C 20 Heterocyclic group; C 3 -C 20 Cycloalkyl group; C 7 -C 20 Arylalkyl group; and C 8 -C 20 and further, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C 3 -C 60 Aliphatic ring or C 6 -C 60 Aromatic ring or C 2 -C 60 A heterocyclic group or a condensed ring formed by combining them.

[0152] Formula 3 is represented by any one of Formula 3-1 to Formula 3-3.

[0153]

[0154] in:

[0155] Ar 6 ,Ar 7 , L 3 , L 4 and L 5 Same as defined in Equation 3,

[0156] X 1 , X 2 and X 3 Same as the definition of Z,

[0157] R 11 , R 12 , R 13 , R 14 , R 15 and R 16 With R 9 The definition of R is the same, or multiple adjacent R 11, multiple R 12 , multiple R 13 , multiple R 14 , multiple R 15 , multiple R 16 can be bonded to each other to form a ring,

[0158] R, t and v are each independently an integer from 0 to 4, and s, u and w are each independently an integer from 0 to 3.

[0159] Formula 4 can be expressed by any one of Formulas 4-1 to 4-6.

[0160]

[0161] in:

[0162] Z, R 9 , R 10 ,Ar 8 , L 6 , p and q are the same as those defined in Equation 4,

[0163] R 17 With R 9 The definition is the same as

[0164] x is an integer from 0 to 2.

[0165] Formula 4 can be expressed by any one of Formulas 4-7 to 4-9.

[0166]

[0167]

[0168] in:

[0169] Z, Ring A, R 10 ,Ar 8 , L 6 and q are the same as those defined in Equation 4,

[0170] R 18 With R 9 The definition is the same as

[0171] y is an integer from 0 to 6.

[0172] Formula 4 can be expressed by any one of Formulas 4-10 to 4-12.

[0173]

[0174] in:

[0175] Z, Ring A, R 9 ,Ar 8 , L6 and q are the same as those defined in Equation 4,

[0176] R 19 With R 9 The definition is the same as

[0177] z is an integer from 0 to 6.

[0178] Formula 4 can be expressed by any one of Formulas 4-13 to 4-18.

[0179]

[0180]

[0181] in:

[0182] Z, R 9 , R 10 ,Ar 8 , L 6 , p and q are the same as those defined in Formula 4,

[0183] R 17 , R 18 and R 19 With R 9 The definition is the same as

[0184] x is an integer from 0 to 2, and y and z are each independently an integer from 0 to 6.

[0185] Formula 4 can be expressed by Formula 4-19.

[0186]

[0187] R 10 ,Ar 8 , L 6 , R a and q are the same as those defined in Equation 4,

[0188] R 17 and R 18 With R 9 The definition is the same as

[0189] x is an integer of 0-2, and y is an integer of 0-6.

[0190] Specifically, the compound represented by Formula 3 may be any one of the following Compound N-1 to Compound N-96, but is not limited thereto.

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] Specifically, the compound represented by Formula 4 may be any one of the following Compounds S-1 to S-108, but is not limited thereto.

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] In another aspect, the present invention provides a method for repeatedly using a compound represented by Formula 1, the method comprising:

[0203] a step of depositing an organic light-emitting material including a compound represented by Formula 1 in a manufacturing process of an organic light-emitting device;

[0204] a step of removing impurities from the crude organic light-emitting material recovered from the deposition apparatus;

[0205] a step of recovering the removed impurities; and

[0206] A step of purifying the recovered impurities to a purity of 99.9% or higher.

[0207] The step of removing impurities from the crude organic light emitting material recovered from the deposition apparatus may preferably include performing a pre-purification process to obtain a purity of 98% or more by recrystallization in a recrystallization solvent.

[0208] The recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0209] The recrystallization solvent may be preferably used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a nonpolar solvent having a polarity value of 2.0 to 4.7.

[0210] When a mixture of a polar solvent and a non-polar solvent is used, the recrystallization solvent may be used in an amount of 15% (v / v) or less of the non-polar solvent compared to the polar solvent.

[0211] The recrystallization solvent can be preferably used by mixing: N-methylpyrrolidone (NMP) single solvent; or a polar solvent in which any one selected from 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide is mixed with N-methylpyrrolidone; or a single non-polar solvent; or a mixed non-polar solvent; selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate and butanone; or a polar solvent and a non-polar solvent.

[0212] The pre-purification process may include a step of precipitating crystals by cooling to 0°C to 5°C after dissolving the crude organic light emitting material recovered from the deposition apparatus in a polar solvent at 90°C to 120°C.

[0213] The pre-purification process may include the step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C, precipitating crystals by cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C.

[0214] The pre-purification process may include, after dissolving the crude organic light-emitting material recovered from the deposition apparatus in a non-polar solvent, a step of precipitating crystals while concentrating the solvent and removing the non-polar solvent.

[0215] The pre-purification process may include a step of recrystallization with a non-polar solvent followed by a first recrystallization with a polar solvent.

[0216] The step of purifying the recovered impurities to a purity of 99.9% or more may include an adsorption separation process of adsorbing and removing the impurities by adsorption on an adsorbent.

[0217] The adsorbent may be activated carbon, silica gel, alumina or a material used for known adsorption purposes.

[0218] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0219] refer to Figure 1 The organic electronic element (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer between the first electrode (110) and the second electrode (170) containing a single compound or two or more compounds represented by Formula 1. 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. In the case of an inverted organic electronic element, the first electrode may be a cathode, and the second electrode may be an anode.

[0220] 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) formed on the first electrode (110) in sequence. Here, the remaining layers except the light emitting layer (140) may not be formed. The organic material layer may also 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. may be used as a hole blocking layer (see Figure 2 ).

[0221] In addition, the organic electronic element according to the embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer may be formed on a surface of the two surfaces of the first electrode that is not in contact with the organic material layer or on a surface of the two surfaces of the second electrode that is not in contact with the organic material layer. The compound according to the embodiment of the present invention suitable for the organic material layer may be used as a host or dopant 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), a light emitting layer (140), a hole blocking layer or a light efficiency enhancement layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a material for the light emitting layer.

[0222] The organic material layer may include two or more stacks, the stack including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks (see Figure 3 ).

[0223] In addition, even if the same core is used, the band gap, electrical properties, interface properties, etc. may vary depending on the position of the substituent bonding, so the selection of the combination of the core and the sub-substituents associated therewith is also very important, and in particular, when the optimal combination of the energy level and T1 value of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) is achieved, long service life and high efficiency can be achieved at the same time.

[0224] The organic electroluminescent device according to the embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or an alloy thereof is deposited on a substrate to form a cathode, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150) and an electron injection layer (160) is formed thereon, and then a material that can be used as a cathode is deposited thereon, thereby manufacturing the organic electroluminescent device according to the embodiment of the present invention.

[0225] In addition, the present invention provides an organic electronic element, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process or a roll-to-roll process, and the organic material layer provides an organic electronic element containing the compound as an electron transport material.

[0226] As another specific example, the present invention provides an organic electronic element which is used by mixing the same or different compounds among the compounds represented by Formula 1 into an organic material layer.

[0227] In addition, the present invention provides a light-emitting layer composition including the compound represented by Formula 1, and provides an organic electronic element including the light-emitting layer.

[0228] In addition, the present invention also provides an electronic device including a display device including an organic electronic element; and a control unit for driving the display device.

[0229] According to another aspect, the present invention provides a display device, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochrome or white lighting. Here, the electronic device may be a wired / wireless communication terminal currently used or to be used in the future, and covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various televisions, and various computers.

[0230] Hereinafter, a synthesis example of the compound represented by Formula 1 and a manufacturing example of an organic electronic element of the present invention will be described in detail through examples, but are not limited to the following examples.

[0231] [Synthesis example]

[0232] The compound represented by Formula 1 according to the present invention (final product) is synthesized by reacting Sub1 and Sub2 as in Reaction Scheme 1, but is not limited thereto.

[0233] <Reaction Scheme 1>

[0234]

[0235] I. Synthesis of Sub1

[0236] Sub1 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0237] <Reaction Scheme 2>

[0238]

[0239] 1. Synthesis example of Sub1-1

[0240]

[0241]

[0242] (1) Synthesis example of Sub1b-1

[0243] 1,3-Dibromo-5-chlorobenzene (100.0 g, 369.89 mmol) and (phenyl-d5)boronic acid (42.27 g, 332.90 mmol) were dissolved in THF (tetrahydrofuran) (1200 mL) in a round-bottom flask, and K 2 CO 3 (102.25g, 739.78mmol), Pd(PPh 3 ) 4 (12.82 g, 11.10 mmol), water (400 mL) and stirred at 80° C. When the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was purified by MgSO 4 Dried and concentrated. Thereafter, the obtained compound was recrystallized after using a silica gel column to obtain 76.63 g of a product (yield: 76.0%).

[0244] (2) Synthesis example of Sub1a-1

[0245] Sub1b-1 (50.0 g, 183.43 mmol) and (6-phenylnaphthalen-2-yl)boronic acid (45.51 g, 183.43 mmol) were dissolved in THF (tetrahydrofuran) (600 mL) in a round-bottom flask, and K 2 CO 3 (50.70g, 366.86mmol), Pd(PPh 3 ) 4 (6.36 g, 5.50 mmol), water (200 mL) and stirred at 80° C. When the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was purified by MgSO 4 Dried and concentrated. Thereafter, the obtained compound was recrystallized after using a silica gel column to obtain 58.1 g of a product (yield: 80.0%).

[0246] (3) Synthesis example of Sub1-1

[0247] Sub1a-1 (58.1 g, 146.49 mmol), (bis(pinacolato)diboron) (55.8 g, 219.73 mmol) were dissolved in toluene (500 mL) in a round bottom flask, and KOAc (28.75 g, 292.97 mmol), Xphos (3.49 g, 7.32 mmol), Pd 2 (dba) 3 (4.03 g, 4.39 mmol) and stirred at 120° C. When the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was purified by MgSO 4 Dried and concentrated. Thereafter, the obtained compound was recrystallized after using a silica gel column to obtain 46.41 g of a product (yield: 65.0%).

[0248] 2. Synthesis example of Sub1-2

[0249]

[0250] (1) Synthesis example of Sub1a-2

[0251] Sub1b-1 (20.1 g, 73.37 mmol), [2,2'-binaphthyl]-6-ylboronic acid (21.88 g, 73.37 mmol) were dissolved in THF (250 mL) in a round-bottom flask, and K 2 CO 3 (20.28g, 146.75mmol), Pd(PPh 3 ) 4 (2.54 g, 2.20 mmol), water (80 ml), and the method used for the synthesis of Sub1a-1 was used to obtain 26.83 g (yield: 82%) of the product.

[0252] (2) Synthesis example of Sub1-2

[0253] Sub1a-2 (25.0 g, 56.05 mmol) was dissolved in toluene (180 mL) in a round-bottom flask, and (bis(pinacolato)diboron) (21.35 g, 84.08 mmol), KOAc (11.0 g, 112.11 mmol), Xphos (1.34 g, 476.72 mmol), Pd 2 (dba) 3 (1.54 g, 1.67 mmol), and 20.19 g (yield: 67%) of the product was obtained using the method for the synthesis of Sub1a-1.

[0254] 3. Synthesis example of Sub1-4

[0255]

[0256] (1) Synthesis example of Sub1b-4

[0257] 1,3-Dibromo-5-chlorobenzene (50.0 g, 184.95 mmol), (naphthalen-2-yl-d7)boronic acid (29.80 g, 166.45 mmol) were dissolved in THF (600 mL) in a round-bottom flask, and K 2 CO 3 (51.12g, 369.89mmol), Pd(PPh 3 ) 4 (6.41 g, 5.55 mmol), water (200 ml), and the method for synthesizing Sub1b-1 was used to obtain 47.4 g (yield: 79%) of the product.

[0258] (2) Synthesis example of Sub1a-4

[0259] Sub1b-4 (25.0 g, 77.01 mmol), (6-phenylnaphthalen-2-yl)boronic acid (19.1 g, 77.01 mmol) were dissolved in THF (250 mL) in a round-bottom flask, and K 2 CO 3 (21.29g, 154.01mmol), Pd(PPh 3 ) 4 (2.67 g, 2.31 mmol), water (80 ml), and the method for the synthesis of Sub1a-1 was used to obtain 29.3 g (yield: 85%) of the product.

[0260] (3) Synthesis example of Sub1-4

[0261] Sub1a-4 (29.0 g, 64.73 mmol) was dissolved in toluene (220 mL) in a round-bottom flask, and (bis(pinacolato)diboron) (24.6 g, 97.10 mmol), KOAc (12.71 g, 129.46 mmol), Xphos (1.54 g, 3.24 mmol), Pd 2 (dba) 3 (1.78 g, 1.94 mmol), and 22.0 g (yield: 63%) of the product was obtained using the method for the synthesis of Sub1a-1.

[0262] 4. Synthesis example of Sub1-6

[0263]

[0264] (1) Synthesis example of Sub1a-6

[0265] Sub1b-4 (20.0 g, 61.60 mmol), [2,2'-binaphthyl]-6-ylboronic acid (18.37 g, 61.60 mmol) were dissolved in THF (210 mL) in a round-bottom flask, and K 2 CO 3 (17.03g, 123.21mmol), Pd(PPh 3 ) 4 (2.14 g, 1.85 mmol), water (70 ml), and the method used for the synthesis of Sub1a-1 was used to obtain 26.4 g (yield: 86%) of the product.

[0266] (2) Synthesis example of Sub1-6

[0267] Sub1a-6 (26.00 g, 52.20 mmol) was dissolved in toluene (170.0 mL) in a round-bottom flask, and (bis(pinacolato)diboron) (19.80 g, 78.30 mmol), KOAc (10.25 g, 104.40 mmol), Xphos (1.24 g, 2.61 mmol), Pd 2 (dba) 3 (1.43 g, 1.57 mmol), and 21.54 g (yield: 70%) of the product was obtained using the method for the synthesis of Sub1-1.

[0268] 5. Synthesis example of Sub1-9

[0269]

[0270] (1) Synthesis Example of Sub1b-9

[0271] 1,3-Dibromo-5-chlorobenzene (50.0 g, 184.95 mmol), (naphthalen-2-yl-d7)boronic acid (29.80 g, 166.45 mmol) were dissolved in THF (600 mL) in a round-bottom flask, and K 2 CO 3 (51.12g, 369.89mmol), Pd(PPh 3 ) 4 (6.41 g, 5.55 mmol), water (200 ml), and the method for synthesizing Sub1b-1 was used to obtain 39.7 g (yield: 85%) of the product.

[0272] (2) Synthesis example of Sub1a-9

[0273] Sub1b-9 (30.0 g, 92.41 mmol), (6-(phenyl-d5)naphthalen-2-yl)boronic acid (23.39 g, 92.41 mmol) were dissolved in THF (300 mL) in a round bottom flask, and K 2 CO 3 (25.54g, 184.81mmol), Pd(PPh 3 ) 4 (3.20 g, 2.77 mmol), water (100 ml), and the method used for the synthesis of Sub1a-1 was used to obtain 31.82 g (yield: 76%) of the product.

[0274] (3) Synthesis example of Sub1-9

[0275] Sub1a-9 (30.00 g, 66.22 mmol) was dissolved in toluene (220 mL) in a round bottom flask and (bis(pinacolato)diboron) (21.35 g, 99.33 mmol), KOAc (13.0 g, 132.44 mmol), Xphos (1.58 g, 3.31 mmol), Pd 2 (dba) 3 (1.82 g, 1.99 mmol), and 23.08 g (yield: 64%) of the product was obtained using the method for the synthesis of Sub1-1.

[0276] The compound belonging to Sub1 may be the following compounds, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub1.

[0277]

[0278] [Table 1]

[0279]

[0280] II. Synthesis of Sub2

[0281] Sub2 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 3, but is not limited thereto.

[0282] <Reaction Scheme 3>

[0283]

[0284] 1. Synthesis example of Sub2-2

[0285]

[0286] Sub2a-2 (30.00 g, 132.71 mmol) and Sub2b-2 (32.92 g, 132.71 mmol) were dissolved in THF (tetrahydrofuran) (450 mL) in a round-bottom flask, and NaOH (10.61 g, 265.42 mmol), Pd(PPh 3 ) 4 (4.60 g, 3.98 mmol), water (150 mL) and stirred at 80° C. When the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was purified by MgSO 4 Dried and concentrated. Thereafter, the obtained compound was recrystallized after using a silica gel column to obtain 39.73 g of a product (yield: 76.0%).

[0287] 2. Synthesis example of Sub2-18

[0288]

[0289] Sub2a-18 (30.00 g, 108.65 mmol), Sub2b-18 (23.03 g, 108.65 mmol) were dissolved in THF (360 mL) in a round-bottom flask, and NaOH (8.69 g, 217.30 mmol), Pd(PPh 3 ) 4 (3.77 g, 3.26 mmol), water (120 ml), and the method for synthesizing Sub2-1 was used to obtain 32.35 g (yield: 73.1%) of the product.

[0290] 3. Synthesis example of Sub2-40

[0291]

[0292] 2,4,6-Trichloro-1,3,5-triazine (20.00 g, 108.46 mmol), Sub2b-40 (18.65 g, 108.46 mmol) were dissolved in THF (360 mL) in a round bottom flask, and NaOH (13.02 g, 325.38 mmol), Pd(PPh 3 ) 4 (3.76 g, 3.25 mmol), water (80 ml), and the method for synthesizing Sub2-1 was used to obtain 25 g (yield: 65.0%) of the product.

[0293] 4. Synthesis example of Sub2-46

[0294]

[0295]

[0296] (1) Synthesis example of Sub2a-46

[0297] 2,4,6-Trichloro-1,3,5-triazine (30.00 g, 162.69 mmol), (7-phenylnaphthalen-2-yl)boronic acid (40.36 g, 162.69 mmol) were dissolved in THF (550 mL) in a round bottom flask, and NaOH (13.02 g, 325.38 mmol), Pd(PPh 3 ) 4 (5.64 g, 4.88 mmol), water (180 ml), and the method for synthesizing Sub2-1 was used to obtain 34.75 g (yield: 61%) of the product.

[0298] (2) Synthesis example of Sub2-46

[0299] Sub2a-46 (33.00 g, 93.69 mmol), Sub2b-46 (18.55 g, 93.69 mmol) were dissolved in THF (330 mL) in a round bottom flask, and NaOH (7.50 g, 187.38 mmol), Pd(PPh 3 ) 4 (3.25 g, 2.81 mmol), water (110 ml), and the method for synthesizing Sub2-1 was used to obtain 25.53 g (yield: 58%) of the product.

[0300] 5. Synthesis example of Sub2-60

[0301]

[0302] (1) Synthesis example of Sub2a-60

[0303] 2,4,6-Trichloro-1,3,5-triazine (30.00 g, 162.69 mmol), phenanthrene-1-ylboronic acid (36.13 g, 162.69 mmol) were dissolved in THF (550 mL) in a round bottom flask, and NaOH (13.02 g, 325.38 mmol), Pd(PPh 3 ) 4 (5.64 g, 4.88 mmol), water (180 ml), and the method for synthesizing Sub2-1 was used to obtain 31.10 g (yield: 58.6%) of the product.

[0304] (2) Synthesis example of Sub2-60

[0305] Sub2a-60 (30.00 g, 91.97 mmol), Sub2b-60 (19.05 g, 91.97 mmol) were dissolved in THF (300 mL) in a round bottom flask, and NaOH (7.36 g, 183.95 mmol), Pd(PPh 3 ) 4 (3.19 g, 2.76 mmol), water (100 ml), and the method for synthesizing Sub2-1 was used to obtain 22.88 g (yield: 55.0%) of the product.

[0306] The compound belonging to Sub2 may be the following compounds, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub2.

[0307]

[0308]

[0309]

[0310]

[0311]

[0312] III. Synthesis of the final product

[0313] 1. Synthesis Example of P-1

[0314]

[0315] Sub1-1 (15.00 g, 30.77 mmol) and Sub2-1 (8.23 g, 30.77 mmol) were dissolved in THF (tetrahydrofuran) (150 mL) in a round-bottom flask, and NaOH (2.46 g, 61.54 mmol), Pd(PPh 3 ) 4 (0.71 g, 0.62 mmol), water (50 mL) and stirred at 80° C. When the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was purified by MgSO 4 Dried and concentrated. Thereafter, the obtained compound was recrystallized after using a silica gel column to obtain 15.56 g of a product (yield: 85.3%).

[0316] 2. Synthesis Example of P-21

[0317]

[0318] Sub1-3 (15.00 g, 27.80 mmol), Sub2-18 (11.34 g, 27.80 mmol) were dissolved in THF (140 mL) in a round-bottom flask, and NaOH (2.22 g, 55.60 mmol), Pd(PPh 3 ) 4 (0.64 g, 0.56 mmol), water (45 ml), and the method used for the synthesis of P-1 was used to obtain 19.14 g (yield: 87.7%) of the product.

[0319] 3. Synthesis Example of P-49

[0320]

[0321] Sub1-2 (15.00 g, 27.91 mmol), Sub2-40 (10.26 g, 27.91 mmol) were dissolved in THF (140 mL) in a round-bottom flask, and NaOH (2.23 g, 55.81 mmol), Pd(PPh 3 ) 4 (0.64 g, 0.56 mmol), water (45 ml), and the method used for the synthesis of P-1 was used to obtain 16.79 g (yield: 81.0%) of the product.

[0322] 4. Synthesis Example of P-56

[0323]

[0324] Sub1-3 (15.00 g, 27.80 mmol), Sub2-46 (13.07 g, 27.80 mmol) were dissolved in THF (140 mL) in a round bottom flask, and NaOH (2.23 g, 55.60 mmol), Pd(PPh 3 ) 4 (0.64 g, 0.56 mmol), water (45 ml), and the method used for the synthesis of P-1 was used to obtain 19.19 g (yield: 81.5%) of the product.

[0325] 5. Synthesis Example of P-69

[0326]

[0327] Sub1-8 (15.00 g, 27.55 mmol), Sub2-58 (8.89 g, 27.55 mmol) were dissolved in THF (135 mL) in a round bottom flask, and NaOH (2.20 g, 55.09 mmol), Pd(PPh 3 )4 (0.64 g, 0.55 mmol), water (40 ml), and the method used for the synthesis of P-1 was used to obtain 15.34 g (yield: 79.0%) of the product.

[0328] Meanwhile, the FD-MS values ​​of Compound P-1 to Compound P-76 of the present invention prepared according to the Synthesis Examples as described above are shown in Table 3.

[0329] [Table 3]

[0330]

[0331]

[0332]

[0333] [Synthesis example 2]

[0334] 1. Synthesis Example of N-12

[0335]

[0336] Add N-12a (30 g, 0.08 mol), N-12b (34.8 g, 0.08 mol), Pd 2 (dba) 3 (2.3g, 0.003mol), NaOt-Bu (24.5g, 0.25mol), P(t-Bu) 3 (2.1 g, 0.005 mol), toluene (170 mL) and reacted at 135° C. for 6 hours. When the reaction was completed, 53 g (85.8%) of product N-12 was obtained using the separation method of P-1.

[0337] 2. Synthesis Example of N-19

[0338]

[0339] Add N-19a (50 g, 0.13 mol), N-19b (35 g, 0.13 mol), Pd 2 (dba) 3 (3.6g, 0.004mol), NaOt-Bu (37.6g, 0.40mol), P(t-Bu) 3 (3.2 g, 0.008 mol), toluene (260 mL) and reacted at 135° C. for 6 hours. When the reaction was completed, 67 g (83.4%) of product N-19 was obtained using the separation method of P-1.

[0340] 3. Synthesis example of S-32

[0341]

[0342] S-32a (10 g, 0.04 mol), S-32b (15.6 g, 0.04 mol), Pd 2 (dba) 3 (1.1g, 0.001mol), NaOt-Bu (11.7g, 0.12mol), P(t-Bu) 3 (1.0 g, 0.002 mol), toluene (80 mL) and reacted at 135° C. for 6 hours. When the reaction was completed, 18 g (80.8%) of the product S-32 was obtained using the separation method of P-1.

[0343] 4. Synthesis Example of S-74

[0344]

[0345] S-74a (15 g, 0.06 mol), S-74b (20.9 g, 0.06 mol), Pd 2 (dba) 3 (1.6g, 0.002mol), NaOt-Bu (16.9g, 0.18mol), P(t-Bu) 3 (1.4 g, 0.004 mol), toluene (120 mL) and reacted at 135° C. for 6 hours. When the reaction was completed, 27 g (86.4%) of the product S-74 was obtained using the separation method of P-1.

[0346] 5. Synthesis of S-104

[0347]

[0348] S-104a (30 g, 0.13 mol), S-104b (48.29 g, 0.13 mol), Pd 2 (dba) 3 (3.5g, 0.004mol), NaOt-Bu (36.4g, 0.38mol), P(t-Bu) 3 (3.1 g, 0.008 mol), toluene (250 mL) and reacted at 135° C. for 6 hours. When the reaction was completed, 60 g (81.5%) of product S-104 was obtained using the separation method of P-1.

[0349] Meanwhile, FD-MS values ​​of Compound N-1 to Compound N-96 and Compound S-1 to Compound S-108 of the present invention prepared according to the Synthesis Examples as described above are shown in Tables 4 and 5.

[0350] [Table 4]

[0351]

[0352]

[0353]

[0354] [Table 5]

[0355]

[0356]

[0357]

[0358] In addition, the synthesis examples of the present invention represented by Formula 1 to Formula 4 have been described, but these are based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh 3 -mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and it should be easily understood by those skilled in the art that the reaction can proceed even when other substituents defined in Formulae 2 to 5 are bonded in addition to the substituents specified in the specific synthesis examples.

[0359] [Device data]

[0360] [Example 1] Red organic light-emitting device (phosphorescent host)

[0361] An organic light-emitting device is manufactured using the compound obtained by synthesis as a light-emitting host material for a light-emitting layer according to a conventional method. 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1-phenylbenzene-1,4-diamine (hereinafter, abbreviated as 2-TNATA) is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60nm, and as a hole transport compound on the hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, abbreviated as NPD) is vacuum deposited to a thickness of 60nm to form a hole transport layer. A light-emitting auxiliary layer is formed by vacuum depositing tris(4-(9H-carbazole-9-yl)phenyl)amine (hereinafter, abbreviated as TCTA) as a light-emitting auxiliary layer material on the top of the hole transport layer to a thickness of 10nm. After the light-emitting auxiliary layer is formed, as the main body on the light-emitting auxiliary layer, the compound P-1 of the present application represented by Formula 1 and the compound N-12 of the present application represented by Formula 3 are used in a weight ratio of (5:5), and (piq) as a dopant material is doped at a weight ratio of 95:5. 2 Ir(acac) was used to deposit a light-emitting layer having a thickness of 30 nm. Next, (1,1'-biphenyl)-4-aluminum (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinolato)beryllium (hereinafter abbreviated as Alq) was vacuum deposited to a thickness of 10 nm as an electron transport layer. 3 ) was formed to have a thickness of 25 nm. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light-emitting device.

[0362] [Example 2] to [Example 26]

[0363] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 6 was used instead of the compound P-1 of the present invention as the host material of the light-emitting layer, and the compound of the present invention described in Table 6 was used instead of the compound N-12 of the present invention.

[0364] [Comparative Example 1] to [Comparative Example 3]

[0365] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound A, Comparative Compound B, or Comparative Compound C was used instead of Compound P-1 of the present invention as a host material of the light-emitting layer.

[0366]

[0367] For the organic electroluminescent devices manufactured in Examples 1 to 26 and Comparative Examples 1 to 3 prepared as described above, electroluminescent (EL) characteristics were measured by applying a forward bias DC voltage using PR-650 manufactured by PhotoResearch Co. As a result of the measurement, the lifetime measurement device manufactured by McScience at 2,500 cd / m 2 Table 6 shows the results of device fabrication and evaluation.

[0368] The measurement setup is independent of possible day-to-day variations in deposition rate, vacuum quality or other tool performance parameters and allows the performance of new materials to be evaluated compared to comparative compounds under identical conditions.

[0369] At the time of evaluation, each field contained 4 identically prepared OLEDs comprising comparative compounds, and since the performance of each of a total of 12 OLEDs in 3 fields was evaluated, the statistical evaluation of the experimental results obtained clearly showed statistical significance.

[0370] [Table 6]

[0371]

[0372]

[0373] It can be seen from the results of Table 6 that when the material for an organic light-emitting device of the present invention is used as a phosphorescent host material to manufacture a red organic light-emitting device, the compound of the present invention is very excellent in efficiency and exhibits significant characteristics compared with the case of using comparative compounds A to C.

[0374] From the above, it can be seen that when the main body of the light-emitting layer is formed by mixing multiple compounds, significant differences in characteristics occur depending on the types of the first compound and the second compound. Similarly, depending on the type of the second compound, it shows differences in driving voltage, efficiency and service life.

[0375] Comparing Comparative Compound C with the compound of the present invention, the compound of the present invention is different from Comparative Compound C in that the deuterium-substituted phenyl group or the deuterium-substituted naphthyl group is further substituted. In contrast, in the case of Comparative Compound A and Comparative Compound B, it can be seen that there is a structural difference in that the deuterium-substituted phenyl group or the deuterium-substituted naphthyl group is substituted instead of the deuterium-substituted phenyl group or the deuterium-substituted naphthyl group, unlike the compound of the present invention. That is, it can be seen that a difference occurs in the overall efficiency of the device due to the structural difference.

[0376] Therefore, it can be determined that the device results of Examples 1 to 26 prepared using the compounds of the present invention represented by Formula 1, Formula 3 or Formula 4 show significantly excellent results, and the device performance is superior to other comparative compounds not described herein.

[0377] Table 7 describes the calculated reorganization energy values ​​of Comparative Compounds A to C and P-1. The RE values ​​listed in Table 7 refer to the calculated RE 空穴 The value obtained.

[0378] [Table 7]

[0379] Comparative Compound A Comparative Compound B Comparative Compound C P-1 Reorganization Energy 0.182 0.219 0.155 0.235

[0380] Referring to Table 7 in detail, the compound P-1 of the present invention has a higher RE value than the comparative compounds A to C. These RE values ​​differ depending on the substituents of the triazine, and in the case of the present invention, a higher RE value is obtained, which means low mobility and slow HOD.

[0381] That is, due to the low RE value, by reducing the mobility of holes injected into the light-emitting layer, the light-emitting area can be narrowed, and light generation can be concentrated by the narrowed light-emitting area to improve efficiency. However, there is a disadvantage that the service life is reduced (tradeoff) in contrast to the efficiency, and the service life can be increased by using deuterium. That is, due to the substitution of deuterium, the reduction of diffusion and reaction rate such as the movement rate of molecules can be delayed, and thus the service life can be improved.

[0382] Therefore, due to the synergistic effect caused by substituting deuterium in a specific substituent as in the present invention, it seems that the efficiency is significantly improved while maintaining the service life.

[0383] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be appreciated by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments.

[0384] The scope of the present invention should be interpreted based on the appended claims, and should be interpreted that all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0385] [Code Description]

[0386] 100, 200, 300: organic electronic element 110: first electrode

[0387] 120: hole injection layer 130: hole transport layer

[0388] 140: Light-emitting layer 150: Electron transport layer

[0389] 160: electron injection layer 170: second electrode

[0390] 180: Light efficiency enhancement layer 210: Buffer layer

[0391] 220: Light-emitting auxiliary layer 320: First hole injection layer 330: first hole transport layer 340: first light emitting layer

[0392] 350: first electron transport layer 360: first charge generation layer 361: second charge generation layer 420: second hole injection layer 430: second hole transport layer 440: second light emitting layer 450: Second electron transport layer CGL: Charge generation layer ST1: first stack ST2: second stack

Claims

1. A compound represented by Formula 1: <Formula 1> in: Ar 1 is a substituent represented by formula 1-A; or a substituent represented by formula 1-B; Ar 2 is a substituent represented by formula 1-C; or a substituent represented by formula 1-D; Ar 3 and Ar 4 Each independently is C6-C 60 or a C2-C ... 60 Heterocyclic groups; R 1 and R 2 are the same or different and are independently hydrogen; or deuterium; L 1 and L 2 Each is independently a single bond; C6-C 60 Arylene group; C2-C 60 Heterocyclic groups; a is an integer from 0 to 6, b is an integer from 0 to 3, In Formula 1-A to Formula 1-D, R 3 are the same or different and are independently hydrogen; or deuterium; D stands for deuterium, c is an integer from 0 to 5, d is an integer from 0 to 7, e is an integer from 1 to 5, f is an integer from 1 to 7, * means the position to be bonded, wherein the aryl group, the arylene group and the heterocyclic group may be substituted by one or more substituents selected from deuterium; C6-C 20 Aryl groups; and deuterated C6-C 20 Aryl group.

2. The compound according to claim 1, wherein Formula 1 is represented by any one of Formula 1-1 to Formula 1-4: in, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 3 ,Ar 4 , a, b, c, d, e, f and D are the same as defined in claim 1.

3. The compound as claimed in claim 1, wherein L 1 and L 2 At least one of the following is represented by any one of Formula a-1 to Formula a-20: in: R 6 are the same or different and are each independently deuterated; C6-C 20 Aryl groups; and deuterated C6-C 20 Aryl groups; g, h and i are each independently an integer from 0 to 4, j is an integer from 0 to 6, k is an integer from 0 to 8, * Means bonded to triazine or Ar 3 or Ar 4 part.

4. The compound of claim 1, wherein Ar 3 and Ar 4 At least one of the following formulas b-1 to b-12 is represented by any one of: in: X is NR 8 , O or S, R 7 are the same or different and are each independently deuterated; C6-C 20 Aryl groups; and deuterated C6-C 20 Aryl groups; R 8 It is C6-C 60 or a C2-C ... 60 Heterocyclic groups; l is an integer from 0 to 5, m and o are each independently an integer from 0 to 7, n is an integer from 0 to 9, Means to bind to L 1 or L 2 part.

5. The compound according to claim 1, wherein the compound represented by Formula 1 can be any one of the following compounds P-1 to P-76:

6. Organic electronic components, including: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, wherein the light-emitting layer is a phosphorescent light-emitting layer and comprises a first host compound represented by Formula 1 of claim 1 and a second host compound represented by Formula 3 or Formula 4: in: L 3 , L 4 , L 5 and L 6 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; Ar 5 ,Ar 6 and Ar 7 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; Ar 8 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-NR b R c ; Z is O, S, CR'R" or NR a , Ring A is C6-C 20 Aryl groups, R 9 and R 10 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; and C6-C 60 Aryloxy group; or multiple adjacent R 9 or multiple R 10 can be bonded to each other to form a ring, p and q are each independently an integer from 0 to 4, L' is each independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; R b and R c Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 aliphatic ring; R' and R" are each independently selected from hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; and C6-C 60 aryloxy group; or R' and R" may be bonded to each other to form a ring, R a It is C6-C 60 or a C2-C ... 60 Heterocyclic groups; wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the condensed 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 deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; and C8-C 20 and further, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by a combination thereof.

7. The compound according to claim 6, wherein the compound represented by Formula 3 can be any one of the following compounds N-1 to N-96:

8. The compound according to claim 6, wherein the compound represented by Formula 4 can be any one of the following compounds S-1 to S-108: 9 . The organic electronic element of claim 6 , wherein the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 10 . The organic electronic element according to claim 6 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 11 . The organic electronic element according to claim 10 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies. 12 . An electronic device comprising a display device including the organic electronic element according to claim 6 ; and a control unit for driving the display device. 13 . The electronic device of claim 12 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white lighting.

14. A method for reusing the compound represented by Formula 1 according to claim 1, comprising: A step of depositing an organic light-emitting material including the compound represented by Formula 1 in claim 1 during the manufacturing process of an organic light-emitting device; a step of removing impurities from the crude organic light-emitting material recovered from the deposition apparatus; a step of recovering the removed impurities; as well as A step of purifying the recovered impurities to a purity of 99.9% or higher.

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