Compound for organic electronic element, organic electronic element using the same, and electronic device having the organic electronic element

Abstract

The present invention provides novel compounds, organic electronic components using the compounds, and electronic devices having the organic electronic components, and the novel compounds can improve the light-emitting efficiency, stability and service life of the components.

Description

Technical Field

[0001] The present invention relates to a compound for an organic electronic device, an organic electronic device 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 an organic material. An organic electronic device 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 device, the organic material layer is usually composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like.

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

[0004] Service life and efficiency are the biggest problems of the organic electroluminescent device, and as the display becomes larger, these problems of efficiency and service life must be solved. Efficiency, service life, and driving voltage are related to each other. When the efficiency increases, the driving voltage relatively decreases, and as the driving voltage decreases, the crystallization of the organic material due to Joule heating generated during driving decreases, so the service life tends to increase.

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

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

[0007] Generally, electrons transfer from the electron transport layer to the light-emitting layer, and holes transfer from the hole transport layer to the light-emitting layer, and excitons are generated by recombination.

[0008] However, since the material for the hole transport layer should have a low HOMO value, most of them have a low T1 value. As a result, the excitons generated in the light-emitting layer transfer to the hole transport layer, resulting in charge imbalance in the light-emitting layer, and thus light emission occurs at the hole transport layer interface.

[0009] When light emission occurs at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device decrease, and the service life is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer having a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0010] In addition, there is a need to develop a hole injection layer material that delays the penetration and diffusion of metal oxides from the anode electrode (ITO) to the organic layer (which is one of the reasons for shortening the service life of organic electronic devices), and has stable properties, that is, a high glass transition temperature, even resistant to Joule heating generated during device driving. The low glass transition temperature of the hole transport layer material has the property of reducing the uniformity of the film surface during device driving, which is reported to have a significant impact on the device service life. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand long-term deposition, that is, a material with strong heat resistance.

[0011] In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, light-emitting auxiliary layer materials, etc., which are composed of stable and effective materials, should be given priority to constitute the organic material layers in the device. However, the development of stable and effective organic material layer materials for organic electronic devices has not been fully realized. Therefore, there is a need to continuously develop new materials.

[0012] KR1020130076842 A is a prior art document used as a reference. Summary of the Invention

[0013] In order to solve the problems of the above-mentioned background art, the present invention discloses a compound having a new structure, and when the compound is applied to an organic electronic device, it has been found that the light-emitting efficiency, stability, and service life of the device can be significantly improved.

[0014] Therefore, an object of the present invention is to provide a new compound, an organic electronic device using the compound, and an electronic device thereof.

[0015] [Technical Solution]

[0016] The present invention provides a compound represented by Formula 1.

[0017] Formula 1

[0018]

[0019] On the other hand, the present invention provides an organic electronic device and an electronic device thereof containing the compound represented by Formula 1.

[0020] [Advantages 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 service life of the device can be significantly improved. BRIEF DESCRIPTION OF THE DRAWINGS

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

[0023] Figure 4 shows a formula according to an aspect of the present invention.

[0024] 100, 200, 300: organic electronic elements 110: first electrode

[0025] 120: hole injection layer 130: hole transport layer

[0026] 140: light emitting 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 emission assisting layer 320: first hole injection layer

[0030] 330: first hole transport layer 340: first light emitting 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 light emitting layer

[0034] 450: second electron transport layer CGL: charge generation layer

[0035] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0036] Hereinafter, some embodiments of the present invention will be described in detail. In addition, in the following description of the present invention, when the detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, such detailed description will be omitted.

[0037] 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 define the essence, order or sequence of the corresponding components, but only to distinguish the corresponding components from other components. It should be noted that if a component is described as "connected", "coupled" or "joined" to another component, the component may be directly connected or joined to the other component, but another component may be "connected", "coupled" or "joined" between the components.

[0038] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0039] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0040] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond with 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 with an alkyl group or an alkyl group substituted with a cycloalkyl group.

[0041] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond with 2 to 60 carbon atoms, but is not limited thereto, and includes a straight-chain or branched-chain group.

[0042] Unless otherwise specified, the term "cycloalkyl" means an alkyl group forming a ring with 3 to 60 carbon atoms, but is not limited thereto.

[0043] Unless otherwise specified, the term "alkoxy", "alkoxy group" or "alkyloxy" as used herein means an oxygen atom connected to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0044] Unless otherwise specified, the term "aryloxy group" or "aryloxy" as used herein means an oxygen atom connected to an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0045] 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 participating in a reaction through adjacent substituents.

[0046] For example, an aryl group may be a phenyl group, a biphenyl group, a fluorene group or a spirofluorene group.

[0047] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl can be an alkyl group substituted with an aryl group, and arylalkenyl can be an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0048] In addition, when the prefixes are named in sequence, this means listing the substituents in the order described first. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, where arylcarbonyl can be a carbonyl group substituted with an aryl group.

[0049] 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 either monocyclic or polycyclic, and can include heteroaliphatic rings and heteroaromatic rings. In addition, it can also combine with adjacent groups to form a heterocyclic group.

[0050] Unless otherwise specified, the term "heteroatom" as used herein represents at least one of N, O, S, P, or Si.

[0051] In addition, the term "heterocyclic group" can include a ring containing SO2 in place of the carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0052]

[0053] 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'' are all hydrogen in the following structure, 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.

[0054]

[0055] The term "spiro compound" as used herein has "spiro linkage", and spiro linkage means a connection in which two rings share only one atom. At this time, the atom shared in the two rings is called a "spiro atom", and these compounds are respectively called "monospiro-", "dispiro-", and "trispiro-" according to the number of spiro atoms in the compound.

[0056] 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.

[0057] Unless otherwise specified, as used herein, the term "ring" 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 fused ring formed by their combination, and includes a saturated ring or an unsaturated ring.

[0058] In addition to the hetero-compounds mentioned above, other hetero-compounds or hetero-groups contain, but are not limited to, one or more heteroatoms.

[0059] Furthermore, unless explicitly specified, as used herein, "substituted" in the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 alkyl group, C1-C 20 alkoxy group, C1-C 20 alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C3-C 20 cycloalkyl group, C6-C 20 aryl group, C6-C aryl group substituted by deuterium 20 aryl group, C8-C 20 arylalkenyl group, silyl group, boron group, germanium group and C2-C 20 heterocyclic group, but not limited to these substituents.

[0060] Furthermore, unless there is a clear explanation, the definitions of the substituents defined by the indices in the formulas used in the present invention are the same as those in the following formulas.

[0061]

[0062] Here, when a is an integer of zero, the substituent R 1 does not exist. When a is an integer of 1, the only substituent R 1 is bonded to any one of the carbons constituting the benzene ring. When a is an integer of 2 or 3, they are bonded as follows, where R 1 can be the same as or different from each other. When a is an integer of 4 to 6, it is bonded to the carbons of the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0063]

[0064] Hereinafter, compounds according to aspects of the present invention and organic electronic elements containing the compounds will be described.

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

[0066] Formula 1

[0067]

[0068] Wherein each symbol can be defined as follows.

[0069] 1) X is O or S,

[0070] 2) a and b are each independently 0 or 1, provided that a + b is 1 or greater than 1;

[0071] 3) Ar 1 and Ar 2 are each independently selected from C6-C 60 aryl groups; fluorenyl groups; C2-C 60 heterocyclic groups containing at least one heteroatom of O, N, S, Si or P; and C3-C 60 alicyclic rings and C6-C 60 fused ring groups of aromatic rings.

[0072] Wherein if Ar 1 and Ar 2 are aryl groups, it may preferably be a C6-C 30 aryl group, and more preferably a C6-C 25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0073] If Ar 1 and Ar 2 are heterocyclic groups, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0074] If Ar 1 and Ar 2 are fused ring groups, it may preferably be a C3-C 30 alicyclic ring and C6-C 30 fused ring group of aromatic rings, more preferably a C3-C 24 alicyclic ring and C6-C 24 fused ring group of aromatic rings.

[0075] 4) L 1 、L 2 、L3 , L 4 , L 5 and L 6 are each independently selected from a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; and a C3-C 60 alicyclic ring and a fused ring group of a C6-C 60 aromatic ring.

[0076] Wherein if L 1 , L 2 , L 3 , L 4 , L 5 and L 6 is an arylene group, it may preferably be a C6-C 30 arylene group, more preferably a C6-C 24 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0077] If L 1 , L 2 , L 3 , L 4 , L 5 and L 6 is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0078] If L 1 , L 2 , L 3 , L 4 , L 5 and L 6 is a fused ring group, it may preferably be a C3-C 30 alicyclic ring and a fused ring group of a C6-C 30 aromatic ring, more preferably a C3-C 24 alicyclic ring and a fused ring group of a C6-C 24 aromatic ring.

[0079] 5) i) If a is 0, R 1 is independently selected from hydrogen; deuterium; tritium; a C1-C 60 alkyl group; a C2-C60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; C3-C 60 aliphatic ring and C6-C 60 fused ring group of aromatic ring; or R 1 and R 2 bond to each other to form a ring.

[0080] Wherein if R 1 is an alkyl group, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0081] If R 1 is an alkenyl group, it may preferably be a C2-C 30 alkenyl group, more preferably a C2-C 24 alkenyl group.

[0082] If R 1 is an alkynyl group, it may preferably be a C2-C 30 alkynyl group, more preferably a C2-C 24 alkynyl group.

[0083] If R 1 is an alkoxy group, it may preferably be a C1-C 30 alkoxy group, more preferably a C1-C 24 alkoxy group.

[0084] If R 1 is an aryloxy group, it may preferably be a C6-C 30 aryloxy group, more preferably a C6-C 24 aryloxy group.

[0085] If R 1 is an aryl group, it may preferably be a C6-C 30 aryl group, more preferably a C6-C 25 aryl group.

[0086] If R 1 is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24Heterocyclic groups, for example, it can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0087] If R 1 is a fused ring group, it can preferably be a fused ring group of C3-C 30 aliphatic ring and C6-C 30 aromatic ring, more preferably a fused ring group of C3-C 24 aliphatic ring and C6-C 24 aromatic ring.

[0088] ii) When a is 1, R 1 is Z; where Z is selected from C6-C 60 arylene group; fluorenylene group; C2-C 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; or Z and R 2 can be bonded to each other to form a ring.

[0089] Where if Z is an arylene group, it can preferably be a C6-C 30 arylene group, and more preferably a C6-C 24 arylene group, for example, it can be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0090] If Z is a heterocyclic group, it can preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group, for example, it can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0091] If Z is a fused ring group, it can preferably be a fused ring group of C3-C 30 aliphatic ring and C6-C 30 aromatic ring, more preferably a fused ring group of C3-C 24 aliphatic ring and C6-C 24 aromatic ring.

[0092] 6) R 2 is independently selected from hydrogen; deuterium; tritium; C1-C 60Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C6-C 60 Aryloxy group; C6-C 60 Aryl group; Fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Fused ring group of aromatic ring.

[0093] Wherein if R 2 is an alkyl group, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0094] If R 2 is an alkenyl group, it may preferably be a C2-C 30 alkenyl group, more preferably a C2-C 24 alkenyl group.

[0095] If R 2 is an alkynyl group, it may preferably be a C2-C 30 alkynyl group, more preferably a C2-C 24 alkynyl group.

[0096] If R 2 is an alkoxy group, it may preferably be a C1-C 30 alkoxy group, more preferably a C1-C 24 alkoxy group.

[0097] If R 2 is an aryloxy group, it may preferably be a C6-C 30 aryloxy group, more preferably a C6-C 24 aryloxy group.

[0098] If R 2 is an aryl group, it may preferably be a C6-C 30 aryl group, more preferably a C6-C 25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0099] If R 2 is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24Heterocyclic groups, for example, it 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.

[0100] If R 2 is a fused ring group, it can preferably be a fused ring group of a C3-C 30 aliphatic ring and a C6-C 30 aromatic ring, more preferably a fused ring group of a C3-C 24 aliphatic ring and a C6-C 24 aromatic ring.

[0101] 7) R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are independently selected from hydrogen; deuterium; tritium; C1-C 60 alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C 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, or where if m, n, o, p, q, r, s and t are 2 or greater than 2, multiple R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are each the same or different, or multiple R 3 or multiple R 4 or multiple R 5 or multiple R 6 or multiple R 7 or multiple R 10 or multiple R 11 or multiple R12 They can be bonded to each other to form a ring.

[0102] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are alkyl groups, which can preferably be C1-C 30 alkyl groups, and more preferably C1-C 24 alkyl groups.

[0103] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are alkenyl groups, which can preferably be C2-C 30 alkenyl groups, more preferably C2-C 24 alkenyl groups.

[0104] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are alkynyl groups, which can preferably be C2-C 30 alkynyl groups, more preferably C2-C 24 alkynyl groups.

[0105] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are alkoxy groups, which can preferably be C1-C 30 alkoxy groups, more preferably C1-C 24 alkoxy groups.

[0106] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are aryloxy groups, which may preferably be C6-C 30 aryloxy groups, and more preferably C6-C 24 aryloxy groups.

[0107] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are aryl groups, which may preferably be C6-C 30 aryl groups, and more preferably C6-C 25 aryl groups, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0108] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 are heterocyclic groups, which may preferably be C2-C 30 heterocyclic groups, and more preferably C2-C 24 heterocyclic groups, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0109] If R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12is a fused ring group, which may preferably be a C3-C 30 aliphatic ring and a C6-C 30 fused ring group of an aromatic ring, more preferably a C3-C 24 aliphatic ring and a C6-C 24 fused ring group of an aromatic ring.

[0110] 8) R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 may be bonded to each other to form a ring. However, unless R 5 and R 8 or R 9 and R 12 are bonded to each other to form a ring,

[0111] 9) m, n, o, p, q, r, s and t are each independently an integer from 0 to 4,

[0112] 10) wherein, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene 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 deuterium; halogen; silyl group; siloxy 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 aryl group substituted by deuterium; fluorenyl group; C2-C 20 heterocyclic group; C3-C 20 cycloalkyl group; C7-C 20 arylalkyl group; and C8-C 20 arylalkenyl group; In addition, the substituents may be bonded to each other to form a saturated or unsaturated ring, where the term "ring" means a C3-C 20 aliphatic ring or a C6-C 60 aromatic ring or a C2-C 60 heterocyclic group or a fused ring formed by their combination. 60

[0113] In addition, Z is represented by any one of Formulas 2-1 to 2-3

[0114] ​

[0115] In Formulas 2-1 to 2-3, each symbol may be defined as follows.

[0116] 1) X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently CR a or N,

[0117] 2) R a is independently selected from hydrogen; deuterium; tritium; a C1-C 60 alkyl group; a C2-C 60 alkenyl group; a C2-C 60 alkynyl group; a C1-C 60 alkoxy group; a C6-C 60 aryloxy group; a C6-C 60 aryl group; a fluorenyl group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; a C3-C 60 aliphatic ring and a C6-C 60 fused ring group of an aromatic ring; or multiple Rs a may be bonded to each other to form a ring.

[0118] Wherein if R a is an alkyl group, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0119] If R a is an alkenyl group, it may preferably be a C2-C 30 alkenyl group, more preferably a C2-C 24 alkenyl group.

[0120] If R a is an alkynyl group, it may preferably be a C2-C 30 alkynyl group, more preferably a C2-C 24 alkynyl group.

[0121] If R a is an alkoxy group, it may preferably be a C1-C 30 alkoxy group, more preferably a C1-C 24Alkoxy group.

[0122] If R a is an aryloxy group, it may preferably be a C6-C 30 aryloxy group, more preferably a C6-C 24 aryloxy group.

[0123] If R a is an aryl group, it may preferably be a C6-C 30 aryl group, more preferably a C6-C 25 aryl group. For example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0124] If R a is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group. For example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0125] If R a is a fused ring group, it may preferably be a C3-C 30 aliphatic ring and C6-C 30 fused ring group of an aromatic ring, more preferably a C3-C 24 aliphatic ring and C6-C 24 fused ring group of an aromatic ring.

[0126] 3) represents the bonding position.

[0127] In addition, Formula 1 is represented by Formula 2 or Formula 3

[0128]

[0129] {wherein,

[0130] X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、L 1 、L 2 、L3 、L 4 、L 5 、L 6 、Ar 1 、Ar 2 、Z, m, n, o, p, q, r, s, and t are the same as defined above.

[0131] In addition, Formula 1 is represented by any one of Formulas 4 to 9. Preferably, Formula 1 is a compound represented by Formula 5, Formula 6, Formula 8, or Formula 9.

[0132]

[0133]

[0134] {Wherein,

[0135] X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、Ar 1 、Ar 2 、Z, m, n, o, p, q, r, s, and t are the same as defined above.

[0136] In addition, Formula 1 is represented by any one of Formulas 10 to 13

[0137]

[0138] {Wherein,

[0139] X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、L 1 、L 2 、L 3 、Ar 1 、m, n, o, p, and q are the same as defined above.

[0140] In addition, Ar 1 or Ar 2 is represented by Formula 1-1

[0141] Formula 1-1

[0142]

[0143] In Formula 1-1, each symbol can be defined as follows.

[0144] 1) Y is O, S, NR b or CR'R”,

[0145] 2) R 13 , R 14 , R b , R', and R” are independently selected from hydrogen; deuterium; tritium; C1-C 60 alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si, or P 60 heterocyclic group; C3-C 60 aliphatic ring and C6-C 60 fused ring group of an aromatic ring; or multiple adjacent R 13 or multiple R 14 or R' and R” can bond to each other to form a ring.

[0146] Wherein if R 13 , R 14 , R b , R', and R” are alkyl groups, it can preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0147] If R 13 , R 14 , R b , R', and R” are alkenyl groups, they can preferably be a C2-C 30 alkenyl group, more preferably a C2-C 24 alkenyl group.

[0148] If R 13 , R 14 , R b , R', and R” are alkynyl groups, they can preferably be a C2-C 30An alkynyl group, more preferably a C2-C 24 alkynyl group.

[0149] If R 13 、R 14 、R b 、R', and R'' are alkoxy groups, which may preferably be C1-C 30 alkoxy groups, more preferably C1-C 24 alkoxy groups.

[0150] If R 13 、R 14 、R b 、R', and R'' are aryloxy groups, which may preferably be C6-C 30 aryloxy groups, more preferably C6-C 24 aryloxy groups.

[0151] If R 13 、R 14 、R b 、R', and R'' are aryl groups, which may preferably be C6-C 30 aryl groups, and more preferably C6-C 25 aryl groups, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0152] If R 13 、R 14 、R b 、R', and R'' are heterocyclic groups, which may preferably be C2-C 30 heterocyclic groups, and more preferably C2-C 24 heterocyclic groups, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0153] If R 13 、R 14 、R b 、R', and R'' are fused ring groups, which may preferably be fused ring groups of C3-C 30 aliphatic rings and C6-C 30 aromatic rings, more preferably C3-C 24 aliphatic rings and C6-C 24 aromatic rings.

[0154] 3) w is an integer from 0 to 3, x is an integer from 0 to 4,

[0155] 4) Indicates the position to be bonded.

[0156] In addition, Formula 1 is represented by Formula 14 or Formula 15.

[0157]

[0158] {Wherein,

[0159] 1) X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , Z, m, n, o, p, q, r, s, t and

[0160] 2) Y, R 13 , R 14 , w and x are the same as defined above.}

[0161] In addition, Formula 1 is represented by any one of Formulas 16 to 21, and more preferably by Formula 17, Formula 18, Formula 20 or Formula 21.

[0162]

[0163]

[0164] {Wherein,

[0165] 1) X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6, Z, m, n, o, p, q, r, s, t and

[0166] 2) Y, R 13 , R 14 , w and x are the same as those defined above.}

[0167] In addition, Formula 1 is represented by any one of Formulas 22 to 25

[0168]

[0169] {Wherein,

[0170] 1) X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , L 1 , L 2 , L 3 , m, n, o, p, q and

[0171] 2) Y, R 13 , R 14 , w and x are the same as those defined above.}

[0172] In addition, Formula 1-1 is represented by any one of Formulas 1-2 to 1-5.

[0173]

[0174]

[0175] {Wherein,

[0176] Y, R 13 , R 14 , w and x are the same as the definitions of Formula 1-1, representing the position to be bonded.}

[0177] Specifically, the compound represented by Formula 1 can be any one of Compounds P1-1 to P7-4, but is not limited thereto.

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] Reference Figure 1 , the organic electronic device (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer containing a single compound represented by Formula 1 or two or more compounds between the first electrode (110) and the second electrode (170). In this case, the first electrode (110) may be an anode, and the second electrode (170) may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0187] 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). In this case, the remaining layers except for the light-emitting layer (140) may not be formed. A hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc. may also be included, and the electron transport layer (150) etc. may be used as a hole blocking layer (see Figure 2 ).

[0188] In addition, the organic electronic device 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 may be formed on one surface of the two surfaces of the first electrode that does not contact the organic material layer, or on one surface of the two surfaces of the second electrode that does not contact the organic material layer. The compound according to an embodiment of the present invention applicable to the organic material layer may be used as a host or a dopant of the hole injection layer (120), the hole transport layer (130), the light-emitting auxiliary layer (220), the electron transport auxiliary layer, the electron transport layer (150), and the electron injection layer (160), the light-emitting layer (140), or as a material for the 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 hole transport layer, a host of the light-emitting layer, and / or a material for the light-emitting auxiliary layer.

[0189] The organic material layer may include two or more stacked bodies, including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and further includes a charge generation layer formed between the two or more stacked bodies (see Figure 3 ).

[0190] In addition, even in the case of the same core, the band gap, electrical properties, interface properties, etc. can vary depending on the position where the substituent is bonded. Therefore, the selection of the combination of the core and the sub-substituents bonded thereto is also very important. In particular, when an optimal combination of the energy levels and T1 values of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) is achieved, long service life and high efficiency can be achieved simultaneously.

[0191] The organic light-emitting device according to an embodiment of the present invention can be manufactured using a PVD (Physical Vapor Deposition) method. For example, a conductive metal, metal oxide, or alloy thereof is deposited on a substrate to form an anode, and after forming 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) thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

[0192] In addition, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element containing the compound as an electron transport material.

[0193] As another specific example, the same or different compounds represented by Formula 1 are mixed and used in the organic material layer.

[0194] In addition, the present invention provides a composition containing the compound represented by Formula 1 for a hole transport layer, a light-emitting auxiliary layer, or a light-emitting layer, and provides an organic electronic element including a hole transport layer, a light-emitting auxiliary layer, or a light-emitting layer.

[0195] In addition, the present invention provides an electronic device including a display device containing an organic electronic element; and a control unit for driving the display device.

[0196] On the other hand, the organic electronic element is at least one of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, and a device for monochromatic or white illumination. At this time, the electronic device can be a current or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals such as mobile phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controls, navigation units, game consoles, various TVs, and various computers.

[0197] Hereinafter, the synthesis examples of the compound represented by Formula 1 of the present invention and the manufacturing examples of the organic electronic elements of the present invention will be described in detail with reference to the examples, but the present invention is not limited to the following examples.

[0198] [Synthesis Example 1]

[0199] The compound (final product) represented by Formula 1 according to the present invention is synthesized by the following Scheme 1, but not limited thereto. Hal 1 and Hal 2 are I, Br or Cl.

[0200] <Reaction Scheme 1>

[0201]

[0202]

[0203] I. Synthesis of Sub1

[0204] Sub1 in Reaction Scheme 1 is synthesized by the reaction route of Reaction Scheme 2, but not limited thereto. Hal 1 and Hal 2 are I, Br or Cl. Hal 3 is I or Br.

[0205] <Reaction Scheme 2>

[0206]

[0207] 1. Synthesis Example of Sub1-1

[0208]

[0209] (1) Synthesis Example of Sub1-1-a

[0210] Under a nitrogen atmosphere, in a round-bottomed flask, 1-(4-bromophenoxy)-2-iodobenzene (50.0 g, 133 mmol) was dissolved in THF (300 mL), and then cooled to -78 °C. Then, n-BuLi (53 mL) was slowly titrated and the mixture was stirred for 30 minutes. Then, propan-2-one (7.7 g, 133 mmol) was dissolved in THF (145 mL) and slowly titrated into the reaction round-bottomed flask. After stirring at -78 °C for another 1 hour, it was gradually warmed to room temperature. When the reaction was completed, the organic layer was extracted with ethyl acetate and water, dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 33.6 g (yield 82%) of the product.

[0211] (2) Synthesis Example of Sub1-1

[0212] The obtained Sub1-1-a (33.6 g, 109 mmol), acetic acid (273 mL), and concentrated hydrochloric acid (44 mL) were placed in a round-bottom flask and stirred at 60 to 80 °C for 3 hours under a nitrogen atmosphere. When the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 27.2 g (yield 86%) of the product.

[0213] 2. Synthesis Examples of Sub1-2 and Sub1-4

[0214]

[0215] (1) Synthesis Example of Sub1-2-a

[0216] Using the synthesis method of Sub1-1-a, 1-(3-chlorophenoxy)-2-iodobenzene (50.0 g, 151 mmol), n-BuLi (61 mL), and propan-2-one (8.8 g, 151 mmol) were used to obtain 31.8 g of the product (yield 80%).

[0217] (2) Synthesis Examples of Sub1-2 and Sub1-4

[0218] Using the synthesis method of Sub1-1, the obtained Sub1-2-a (31.8 g, 121 mmol), acetic acid (300 mL), and concentrated hydrochloric acid (48 mL) were used to obtain 17.5 g (yield: 59%) of Sub1-2 and 7.4 g (yield: 25%) of Sub1-4.

[0219] 3. Synthesis Example of Sub1-5

[0220]

[0221] (1) Synthesis Example of Sub1-5-a

[0222] Using the synthesis method of Sub1-1-a, 1-(4-bromophenoxy)-2-iodobenzene (25.0 g, 66.7 mmol), n-BuLi (27 mL), and benzophenone (12.1 g, 66.7 mmol) were used to obtain 22.4 g of the product (yield 78%).

[0223] (2) Synthesis Example of Sub1-5

[0224] Using the synthesis of Sub1-1, the obtained Sub1-5-a (22.4 g, 52.0 mmol), acetic acid (130 mL), and concentrated hydrochloric acid (21 mL) were used to obtain 17.6 g of the product (yield 82%).

[0225] Synthesis Example of Sub1-12

[0226]

[0227] (1) Synthesis Example of Sub1-12-a

[0228] Using the synthesis method of Sub1-1-a, 1-iodo-2-phenoxybenzene (25.0 g, 84.4 mmol), n-BuLi (34 mL), and (2-bromophenyl)(phenyl)methanone (22.0 g, 84.4 mmol) were used to obtain 29.5 g of the product (yield 81%).

[0229] (2) Synthesis Example of Sub1-12

[0230] Using the synthesis of Sub1-1, the obtained Sub1-12-a (29.5 g, 68.4 mmol), acetic acid (170 mL), and concentrated hydrochloric acid (27 mL) were used to obtain 22.6 g of the product (yield 80%).

[0231] 5. Synthesis Example of Sub1-13

[0232]

[0233] (1) Synthesis Example of Sub1-13-a

[0234] Using the synthesis method of Sub1-1-a, 1-iodo-2-phenoxybenzene (50.0 g, 169 mmol), n-BuLi (68 mL), and 2-bromo-9H-fluoren-9-one (43.8 g, 169 mmol) were used to obtain 59.4 g of the product (yield 82%).

[0235] (2) Synthesis Example of Sub1-13

[0236] Using the synthesis of Sub1-1, the obtained Sub1-13-a (59.4 g, 138 mmol), acetic acid (345 mL), and concentrated hydrochloric acid (55 mL) were used to obtain 47.3 g of the product (yield 83%).

[0237] 6. Synthesis Example of Sub1-18

[0238]

[0239] After dissolving Sub1-2 (5.0 g, 20.4 mmol) in THF (102 mL), (5-bromo-[1,1'-biphenyl]-3-yl)boronic acid (5.7 g, 20.4 mmol), NaOH (2.5 g, 61.3 mmol), Pd(PPh3)4 (1.42 g, 1.23 mmol) and water (51 mL) were added, and the mixture was stirred at 80 °C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated.

[0240] Thereafter, after applying a silica gel column, the resulting compound was recrystallized to give 6.6 g (yield 71%) of the product.

[0241] 7. Synthesis Example of Sub1-20

[0242]

[0243] (1) Synthesis Example of Sub1-20-a

[0244] Using the synthesis method of Sub1-1-a, (4-bromophenyl)(2-iodophenyl)sulfane (50.0 g, 128 mmol), n-BuLi (51 mL), and propan-2-one (7.4 g, 128 mmol) were used to obtain 34.3 g of the product (yield 83%).

[0245] (2) Synthesis Example of Sub1-20

[0246] Using the synthesis of Sub1-1, the obtained Sub1-20-a (34.3 g, 106 mmol), acetic acid (265 mL), and concentrated hydrochloric acid (42 mL) were used to obtain 26.2 g of the product (yield 81%).

[0247] 8. Synthesis Examples of Sub1-21, Sub1-23

[0248]

[0249] (1) Synthesis Example of Sub1-21-a

[0250] Using the synthesis method of Sub1-1-a, (3-chlorophenyl)(2-iodophenyl)sulfane (50.0 g, 144 mmol), n-BuLi (58 mL), and propan-2-one (8.4 g, 144 mmol) were used to obtain 32.3 g of the product (yield 80%).

[0251] (2) Synthesis Example of Sub1-21

[0252] Using the method of Sub1-1, Sub1-21-a (32.2 g, 115 mmol), acetic acid (290 mL), and concentrated hydrochloric acid (46 mL) were used to obtain 17.2 g of Sub1-21 (yield 57%) and 7.5 g (yield 25%) of Sub1-23.

[0253] 9. Synthesis Example of Sub1-25

[0254]

[0255] (1) Synthesis Example of Sub1-25-a

[0256] Using the synthesis method of Sub1-1-a, (4-bromophenyl)(2-iodophenyl)sulfane (30.0 g, 76.7 mmol), n-BuLi (31 mL), and benzophenone (14.0 g, 76.7 mmol) were used to obtain 28.1 g of the product (yield 82%).

[0257] (2) Synthesis Example of Sub1-25

[0258] Using the synthesis of Sub1-1, the obtained Sub1-25-a (28.1 g, 62.9 mmol), acetic acid (157 mL), and concentrated hydrochloric acid (25 mL) were used to obtain 23.0 g of the product (yield 85%).

[0259] 10. Synthesis Example of Sub1-29

[0260]

[0261] (1) Synthesis Example of Sub1-29-a

[0262] Using the synthesis method of Sub1-1-a, (4-bromophenyl)(2-iodophenyl)sulfane (50.0 g, 128 mmol), n-BuLi (51 mL), and 9H-fluoren-9-one (23.0 g, 128 mmol) were used to obtain 46.7 g of the product (yield 82%).

[0263] (2) Synthesis Example of Sub1-29

[0264] Using the synthesis of Sub1-1, the obtained Sub1-29-a (46.7 g, 105 mmol), acetic acid (262 mL), and concentrated hydrochloric acid (42 mL) were used to obtain 36.3 g of the product (yield 81%).

[0265] 11. Synthesis Example of Sub1-34

[0266]

[0267] (1) Synthesis example of Sub1-34-a

[0268] Using the synthesis method of Sub1-1-a, using (2-iodophenyl)(phenyl)sulfane (25.0 g, 80.1 mmol), n-BuLi (32 mL), (3-bromophenyl)(phenyl)methanone (20.9 g, 80.1 mmol) to obtain 27.9 g of the product (yield 78%).

[0269] (2) Synthesis example of Sub1-34

[0270] Using the synthesis of Sub1-1, using the obtained Sub1-34-a (27.9 g, 62.5 mmol), acetic acid (156 mL) and concentrated hydrochloric acid (25 mL) to obtain 22.0 g of the product (yield 82%).

[0271] 12. Synthesis example of Sub1-50

[0272]

[0273] (1) Synthesis example of Sub1-50-a

[0274] Using the synthesis method of Sub1-1-a, using 1-(4-bromophenoxy)-2-iodobenzene (5.0 g, 13.3 mmol), n-BuLi (5 mL), (4-chlorophenyl)(phenyl)methanone (2.9 g, 13.3 mmol) to obtain 4.9 g of the product (yield 79%).

[0275] (2) Synthesis example of Sub1-50

[0276] Using the synthesis of Sub1-1, using the obtained Sub1-50-a (4.9 g, 10.5 mmol), acetic acid (26 mL) and concentrated hydrochloric acid (4 mL) to obtain 3.7 g of the product (yield 78%).

[0277] The compounds belonging to Sub1 can be the following compounds, but are not limited thereto. Table 1 below shows the FD-MS (field desorption - mass spectrometry) values of some compounds belonging to Sub1.

[0278]

[0279]

[0280] [Table 1]

[0281]

[0282]

[0283] II. Synthesis of Sub2

[0284] Sub2 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 3, but not limited thereto. Hal 4 is I, Br, or Cl.

[0285] <Reaction Scheme 3>

[0286]

[0287] 1. Synthesis Example of Sub2-1

[0288]

[0289] In a round-bottom flask, 9-(4-bromophenyl)-9-phenyl-9H-fluorene (30.0 g, 75.5 mmol) was dissolved in toluene (380 mL), aniline (7.0 g, 75.5 mmol), Pd2(dba)3 (2.07 g, 2.27 mmol), P(t-Bu)3 (0.92 g, 4.53 mmol), and NaOt-Bu (14.5 g, 151 mmol) were added thereto, and the mixture was stirred at 60 °C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 23.2 g (yield 75%) of the product.

[0290] 2. Synthesis Example of Sub2-15

[0291]

[0292] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-phenyl-9H-fluorene (30.0 g, 75.5 mmol), [1,1'-biphenyl]-4-amine (12.8 g, 75.5 mmol), Pd2(dba)3 (2.07 g, 2.27 mmol), P(t-Bu)3 (0.92 g, 4.53 mmol), and NaOt-Bu (14.5 g, 151 mmol) were used to obtain 26.8 g (yield 73%) of the product.

[0293] 3. Synthesis Example of Sub2-34

[0294]

[0295] Using the synthesis method of Sub2-1, 9-(2-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), [1,1'-biphenyl]-3-amine (2.1 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.2 g (yield 68%) of the product.

[0296] 4. Synthesis Example of Sub2-56

[0297]

[0298] Using the synthesis method of Sub2-1, 9-(4-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 9,9-dimethyl-9H-fluoren-2-amine (2.6 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.9 g (yield 74%) of the product.

[0299] 5. Synthesis Example of Sub2-60

[0300]

[0301] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), dibenzo[b,d]thiophen-3-amine (2.5 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.7 g (yield 73%) of the product.

[0302] 6. Synthesis Example of Sub2-65

[0303]

[0304] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), naphtho[2,3-b]benzofuran-3-amine (2.9 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.9 g (yield 71%) of the product.

[0305] 7. Synthesis Example of Sub2-67

[0306]

[0307] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), dibenzo[b,d]furan-2-amine (2.3 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.6 g (yield 73%) of the product.

[0308] 8. Synthesis Example of Sub2-76

[0309]

[0310] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 9,9-dimethyl-9H-fluoren-2-amine (2.6 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 4.6 g (yield 70%) of the product.

[0311] 9. Synthesis Example of Sub2-95

[0312]

[0313] Using the synthesis method of Sub2-1, 9-(2-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 5-phenyl-5H-benzo[b]carbazol-3-amine (3.9 g, 12.6 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), P(t-Bu)3 (0.15 g, 0.76 mmol), and NaOt-Bu (2.4 g, 25.2 mmol) were used to obtain 5.1 g (yield 65%) of the product.

[0314] 10. Synthesis Example of Sub2-105

[0315]

[0316] Using the synthesis method of Sub2-1, 9-(3-bromophenyl)-9-methyl-9H-fluorene (2.0 g, 6.0 mmol), [1,1'-biphenyl]-4-amine (1.0 g, 6.0 mmol), Pd2(dba)3 (0.16 g, 0.18 mmol), P(t-Bu)3 (0.07 g, 0.36 mmol), and NaOt-Bu (1.1 g, 11.9 mmol) were used to obtain 1.8 g (yield 71%) of the product.

[0317] The compounds belonging to Sub 2 can be the following compounds, but are not limited thereto. Table 2 shows the FD-MS (field desorption - mass spectrometry) values of some compounds belonging to Sub 2.

[0318]

[0319]

[0320]

[0321]

[0322] [Table 2]

[0323]

[0324]

[0325]

[0326] III. Synthesis of the Final Product

[0327] 1. Synthesis Example of P1-1

[0328]

[0329] In a round-bottom flask, after dissolving Sub1-1 (2.0 g, 6.9 mmol) in toluene (35 mL), Sub2-2 (3.4 g, 6.9 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.08 g, 0.41 mmol), and NaOt-Bu (1.3 g, 13.8 mmol) were added and the mixture was refluxed. When the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 3.5 g (yield 72%) of the product.

[0330] 2. Synthesis Example of P1-14

[0331]

[0332] Using the synthesis method of P1-1, Sub1-18 (2.0 g, 4.5 mmol), Sub2-1 (1.9 g, 4.5 mmol), Pd2(dba)3 (0.12 g, 0.14 mmol), P(t-Bu)3 (0.06 g, 0.27 mmol), and NaOt-Bu (0.9 g, 9.1 mmol) were used to obtain 2.6 g (yield 74%) of the product.

[0333] 3. Synthesis Example of P2-2

[0334]

[0335] Using the synthesis method of P1-1, Sub1-5 (2.0 g, 4.8 mmol), Sub2-14 (2.0 g, 4.8 mmol), Pd2(dba)3 (0.13 g, 0.15 mmol), P(t-Bu)3 (0.06 g, 0.29 mmol), and NaOt-Bu (0.9 g, 9.7 mmol) were used to obtain 2.6 g (yield 72%) of the product.

[0336] 4. Synthesis Example of P2-11

[0337]

[0338] Using the synthesis method of P1-1, Sub1-13 (2.0 g, 4.9 mmol), Sub2-15 (2.4 g, 4.9 mmol), Pd2(dba)3 (0.13 g, 0.15 mmol), P(t-Bu)3 (0.06 g, 0.29 mmol), and NaOt-Bu (0.9 g, 9.7 mmol) were used to obtain 2.8 g (yield 70%) of the product.

[0339] 5. Synthesis Example of P2-18

[0340]

[0341] Using the synthesis method of P1-1, Sub1-25 (2.0 g, 4.7 mmol), Sub2-16 (2.3 g, 4.7 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), P(t-Bu)3 (0.06 g, 0.28 mmol), and NaOt-Bu (0.9 g, 9.3 mmol) were used to obtain 2.8 g (yield 72%) of the product.

[0342] 6. Synthesis Example of P2-29

[0343]

[0344] Using the synthesis method of P1-1, Sub1-7 (1.8 g, 4.4 mmol), Sub2-105 (1.9 g, 4.4 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol), P(t-Bu)3 (0.05 g, 0.26 mmol), and NaOt-Bu (0.8 g, 8.8 mmol) were used to obtain 2.4 g (yield 73%) of the product.

[0345] 7. Synthesis Example of P3-9

[0346]

[0347] Using the synthesis method of P1-1, Sub1-12 (2.0 g, 4.8 mmol), Sub2-32 (2.0 g, 4.8 mmol), Pd2(dba)3 (0.13 g, 0.15 mmol), P(t-Bu)3 (0.06 g, 0.29 mmol), and NaOt-Bu (0.9 g, 9.7 mmol) were used to obtain 2.1 g (yield 58%) of the product.

[0348] 8. Synthesis Example of P3-17

[0349]

[0350] Using the synthesis method of P1-1, Sub1-20 (2.0 g, 6.6 mmol), Sub2-34 (3.2 g, 6.6 mmol), Pd2(dba)3 (0.18 g, 0.20 mmol), P(t-Bu)3 (0.08 g, 0.39 mmol), and NaOt-Bu (1.3 g, 13.1 mmol) were used to obtain 2.9 g (yield 62%) of the product.

[0351] 9. Synthesis Example of P4-13

[0352]

[0353] Using the synthesis method of P1-1, Sub1-21 (2.0 g, 7.7 mmol), Sub2-56 (4.0 g, 7.7 mmol), Pd2(dba)3 (0.21 g, 0.23 mmol), P(t-Bu)3 (0.09 g, 0.46 mmol), and NaOt-Bu (1.5 g, 15.3 mmol) were used to obtain 4.3 g (yield 75%) of the product.

[0354] 10. Synthesis Example of P5-4

[0355]

[0356] Using the synthesis method of P1-1, Sub1-1 (2.0 g, 6.9 mmol), Sub2-76 (3.6 g, 6.9 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.08 g, 0.41 mmol), and NaOt-Bu (1.3 g, 13.8 mmol) were used to obtain 3.6 g (yield 71%) of the product.

[0357] 11. Synthesis Example of P5-28

[0358]

[0359] Using the synthesis method of P1-1, Sub1-29 (2.0 g, 4.7 mmol), Sub2-67 (2.3 g, 4.7 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), P(t-Bu)3 (0.06 g, 0.28 mmol), and NaOt-Bu (0.9 g, 9.4 mmol) were used to obtain 3.0 g (yield 75%) of the product.

[0360] 12. Synthesis Example of P5-31

[0361]

[0362] Using the synthesis method of P1-1, Sub1-34 (2.0 g, 4.7 mmol), Sub2-65 (2.6 g, 4.7 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), P(t-Bu)3 (0.06 g, 0.28 mmol), and NaOt-Bu (0.9 g, 9.3 mmol) were used to obtain 3.1 g (yield 72%) of the product.

[0363] Synthesis Example of P6-14

[0364]

[0365] Using the synthesis method of P1-1, Sub1-23 (1.5 g, 5.8 mmol), Sub2-85 (3.3 g, 5.8 mmol), Pd2(dba)3 (0.16 g, 0.17 mmol), P(t-Bu)3 (0.07 g, 0.35 mmol), and NaOt-Bu (1.1 g, 11.5 mmol) were used to obtain 2.4 g (yield 52%) of the product.

[0366] Synthesis Example of P7-3

[0367]

[0368] (1) Synthesis Example of Inter7-3

[0369] In a round-bottom flask, after dissolving Sub1-50 (1.5 g, 3.4 mmol) in toluene (17 mL), Sub2-60 (1.7 g, 3.4 mmol), Pd2(dba)3 (0.09 g, 0.10 mmol), P(t-Bu)3 (0.04 g, 0.20 mmol), and NaOt-Bu (0.6 g, 6.7 mmol) were added and stirred at 60 °C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 2.1 g (yield 72%) of the product.

[0370] (2) Synthesis Example of P7-3

[0371] In a round-bottom flask, after dissolving Inter7-3 (2.1 g, 2.4 mmol) in toluene (12 mL), Sub2-2 (1.2 g, 2.4 mmol), Pd2(dba)3 (0.07 g, 0.07 mmol), P(t-Bu)3 (0.03 g, 0.14 mmol), and NaOt-Bu (0.5 g, 4.8 mmol) were added and refluxed. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 2.5 g (yield 78%) of the product.

[0372] Meanwhile, the FD-MS values of the compounds P1-1 to P7-4 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[0373] [Table 3]

[0374]

[0375]

[0376]

[0377] Manufacture and evaluation of organic electronic components

[0378] [Example 1] Green organic light-emitting diode (hole transport layer)

[0379] An organic electroluminescent device was manufactured using the compound of the present invention as a hole transport layer material according to a conventional method.

[0380] First, on an ITO layer (anode) formed on a glass substrate, a film of N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated hereinafter as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. On the hole injection layer, the compound P1-1 of the present invention was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. After forming the hole transport layer, CBP [4,4'-N,N'-dicarbazole-biphenyl] was used as a host, and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] was used as a dopant, doped at a weight ratio of 95:5, and vacuum-deposited to a thickness of 30 nm to form a light-emitting layer on the hole transport layer. Then, (1,1'-biphenyl)-4-yl)bis(2-methyl-8-quinolinolato)aluminum (abbreviated hereinafter as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (abbreviated hereinafter as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. Then, LiF, which is 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 preparing an organic electroluminescent device.

[0381] [Example 2] to [Example 51] Green organic light-emitting diode (hole transport layer)

[0382] An organic electroluminescent device was manufactured in the same manner as in Example 1, but the compounds P1-2 to P7-3 of the present invention described in Table 4 were used instead of the compound P1-1 of the present invention as the hole transport layer material.

[0383] [Comparative Example 1] or [Comparative Example 2]

[0384] An organic electroluminescent device was manufactured in the same manner as in Example 1, but Comparative Compound A or Comparative Compound B was used instead of the compound P1-1 of the present invention as the hole transport layer material.

[0385]

[0386] By applying a forward bias DC voltage to the organic electroluminescent devices of the examples and comparative examples prepared in this manner, the electroluminescent (EL) characteristics were measured using a PR-650 from Photoresearch, and as a measurement result, the T95 service life was measured at a standard brightness of 5000 cd / m 2 using a service life measuring device manufactured by McScience. Table 4 below shows the device fabrication and evaluation results.

[0387] [Table 4]

[0388]

[0389]

[0390]

[0391] As can be seen from the results in Table 4, when the material for an organic electronic device of the present invention is used as a hole transport layer material to fabricate a green organic electronic device, the performance of the organic electroluminescent device can be improved as compared with the comparative examples using Comparative Compound A or Comparative Compound B.

[0392] In other words, if Comparative Example 1 using Comparative Compound A is compared with Comparative Example 2 using Comparative Compound B, the result of Comparative Example 1 shows excellent results in terms of driving voltage, and Comparative Example 2 shows excellent results in terms of efficiency and service life. In addition, Examples 1 to 51 of the compound of the present invention show significantly excellent results in terms of efficiency and service life.

[0393] [Example 52] Green Organic Light Emitting Diode (Luminescence-Assisting Layer)

[0394] An organic electroluminescent device was fabricated using the compound of the present invention as a luminescence-assisting layer material according to a conventional method.

[0395] First, on an ITO layer (anode) formed on a glass substrate, a film of N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated as 2-TNATA below) was vacuum deposited to form a thickness of 60 nm as a hole injection layer. 4,4-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB below) was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Then, the compound P1-1 of the present invention as a material for the light-emitting auxiliary layer was vacuum deposited to a thickness of 20 nm to form a light-emitting auxiliary layer. After forming the light-emitting auxiliary layer, CBP [4,4'-N,N'-dicarbazole-biphenyl] was used as a host, and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] was used as a dopant, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form a light-emitting layer on the light-emitting auxiliary layer. (1,1'-Biphenyl)-4-ylbis(2-methyl-8-quinolinolato)aluminum (abbreviated as BAlq below) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (abbreviated as Alq3 below) was deposited to a thickness of 40 nm as an electron transport layer. Then, 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 preparing an organic electroluminescent device.

[0396] [Example 53] to [Example 102] Green Organic Light-Emitting Diodes (Light-Emitting Auxiliary Layer)

[0397] An organic electroluminescent device was fabricated in the same manner as in Example 47, except that the compounds P1-2 to P7-3 of the present invention described in Table 5 were used instead of the compound P1-1 of the present invention as the light-emitting auxiliary layer material.

[0398] [Comparative Example 3]

[0399] An organic electroluminescent device was fabricated in the same manner as in Example 47, except that the light-emitting auxiliary layer was not used.

[0400] [Comparative Example 4] or [Comparative Example 5]

[0401] An organic electroluminescent device was fabricated in the same manner as in Example 47, except that Comparative Compound A or Comparative Compound B was used instead of the compound P1-1 of the present invention as the light-emitting auxiliary layer material.

[0402] By applying a forward bias DC voltage to the organic electroluminescent devices of the examples and comparative examples prepared in this way, the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch, and as a measurement result, the T95 service life was measured using a service life measuring device manufactured by McScience at a standard brightness of 5000 cd / m 2 The following Table 5 shows the device fabrication and evaluation results.

[0403] [Table 5]

[0404]

[0405]

[0406]

[0407]

[0408] From the results in Table 5, it can be seen that when the material for an organic electronic device of the present invention is used as the light-emitting auxiliary layer material to fabricate a green organic electronic device, the efficiency and service life of the organic electroluminescent device can be improved as compared with the comparative examples in which no light-emitting auxiliary layer is used or comparative compound A or comparative compound B is used.

[0409] In other words, the results of Comparative Example 4 or Comparative Example 5 using comparative compound A or comparative compound B are superior to those of Comparative Example 3 in which no light-emitting auxiliary layer is used, and Examples 52 to 102 of the compound of the present invention show significantly excellent results in terms of efficiency and service life.

[0410] First, if comparative compound A and the compound of the present invention are compared, the difference between comparative compound A and the compound of the present invention lies in the bonding position of the amino group to fluorene. When fluorene is bonded to the amino group, the energy levels (especially HOMO and LUMO) change according to the bonding position, and the physical properties of the compound change. Therefore, as the physical properties of the compound change, the charge balance in the light-emitting layer increases, and light emission occurs exactly inside the light-emitting layer rather than at the interface of the light-emitting layer. Therefore, the deterioration at the interface of the light-emitting layer is also reduced, and the efficiency and service life are improved. Therefore, it is determined that this is the main factor for improving the device performance during device deposition.

[0411] Secondly, the comparison compound B and the compound of the present invention are compared. The comparison compound B has a structure in which a dibenzofuran structure is bonded to an amino group, while the compound of the present invention has a structure in which a xanthene and a thioxanthene structure are bonded to an amino group. In other words, when comparing dibenzofuran and xanthene, due to the addition of sp3 carbon, it is judged that the xanthene structure has improved electron-donating ability and improved hole properties. Due to the introduction of the xanthene structure, the hole characteristics are improved, and the driving voltage, efficiency, and service life are improved.

[0412] Therefore, when diphenylfluorene and the xanthene structure are simultaneously substituted by an amino group as in the compound of the present invention, due to the synergistic effect between diphenylfluorene and xanthene, it is judged that the device performance is significantly excellent.

[0413] Although the exemplary embodiments of the present 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 present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims and should be interpreted to include all technical concepts within the scope equivalent to the claims as belonging to the present invention.

[0414] [Industrial Applicability]

[0415] According to the present invention, an organic device having excellent device characteristics of high brightness, high luminescence, and long service life can be manufactured, and thus has industrial applicability.

Claims

1. A compound represented by Formula 1: Formula 1 Wherein: 1) X is O or S, 2) a and b are each independently 0 or 1, provided that a + b is 1 or greater than 1; 3) Ar 1 and Ar 2 each independently selected from C6-C 25 aryl groups; C2-C containing at least one heteroatom of O, N, S, Si or P 24 heterocyclic groups; and C3-C 24 aliphatic rings and C6-C 24 fused ring groups of aromatic rings, 4) L 1 、L 2 、L 3 and L 5 each independently selected from a single bond; C6-C 24 arylene group, and L 4 and L 6 are each independently a single bond, 5) i) If a is 0, R 1 is independently selected from C1-C 24 alkyl groups; C6-C 25 aryl groups, ii) When a is 1, R 1 is Z; where Z is a C6-C 24 arylene group, 6)R 2 independently selected from C1-C 24 alkyl groups; C6-C 25 aryl groups, 7) R 3 and R 4 are independently selected from hydrogen; deuterium; C1-C 24 alkyl groups; C6-C 25 aryl groups, R 5 , R 7 , R 10 and R 12 are independently selected from hydrogen; deuterium; C1-C 24 alkyl groups, R 6 is independently selected from hydrogen; deuterium, R 8 and R 9 are independently selected from C1-C 24 alkyl groups; C6-C 25 aryl groups, R 11 is independently selected from hydrogen; deuterium; C1-C 24 alkyl groups; C1-C 24 alkenyl groups, or wherein if m, n, o, p, q, r, s and t are 2 or greater than 2, multiple R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each the same or different, or multiple R 10 or multiple R 11 may be bonded to each other to form a ring, 8) m, n, o, p, q, r, s, and t are each independently an integer from 0 to 4, 9) wherein, The aryl group, the arylene group, the heterocyclic group, the fused ring group, the alkyl group and the alkenyl group may be substituted with one or more substituents selected from deuterium; halogen; cyano group; nitro group; C1-C 20 alkoxy group; C1-C 20 alkyl group; C6-C 20 aryl group; C6-C aryl group substituted with deuterium 20 aryl group; C2-C 20 heterocyclic group; C3-C 20 cycloalkyl group; and C7-C 20 arylalkyl group.

2. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or Formula 3: wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、Ar 1 、Ar 2 、Z, m, n, o, p, q, r, s and t are the same as those defined in claim 1.

3. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 4 to 9: Wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、Ar 1 、Ar 2 、Z, m, n, o, p, q, r, s and t are the same as those defined in claim 1.

4. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 10 to 13: where X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , L 1 , L 2 , L 3 , Ar 1 , m, n, o, p, and q are the same as those defined in claim 1.

5. The compound according to claim 1, wherein Ar 1 or Ar 2 is represented by Formula 1-1: Formula 1-1 Wherein: 1) Y is O, S, NR b or CR'R”, 2)R 13 、R 14 、R b 、R', and R" are independently selected from hydrogen; deuterium; a C1-C 24 alkyl group; a C6-C 25 aryl group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, or P; or multiple adjacent R 13 or multiple R 14 or R' and R" may be bonded to each other to form a ring, 3) w is an integer from 0 to 3, and x is an integer from 0 to 4, 4) Indicates the position to be bonded.

6. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 14 or Formula 15: Wherein: 1) X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , Z, m, n, o, p, q, r, s and t are the same as defined in claim 1, and 2) Y, R 13 , R 14 , w and x are the same as those defined in claim 5.

7. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 16 to 21: Wherein: 1) X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、L 1 、L 2 、L 3 、L 4 、L 5 、L 6 、Z, m, n, o, p, q, r, s and t are the same as those defined in claim 1, 2) Y, R 13 , R 14 , w and x are the same as those defined in claim 5.

8. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 22 to 25: Wherein: 1) X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , L 1 , L 2 , L 3 , m, n, o, p, and q are the same as defined in claim 1, 2) Y, R 13 , R 14 , w and x are the same as those defined in claim 5.

9. The compound according to claim 5, wherein Formula 1-1 is represented by any one of Formulas 1-2 to 1-5: Wherein: Y, R 13 , R 14 , w and x are the same as those defined in claim 5, Indicates the position to be bonded.

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

11. A compound comprising any one of the following:

12. An organic electronic device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer contains the single compound represented by Formula 1 according to claim 1 or two or more compounds, or the compound according to claim 11.

13. The organic electronic device according to claim 12, wherein the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light-emission assisting layer, a light-emitting layer, an electron transport assisting layer, an electron transport layer, and an electron injection layer.

14. The organic electronic device according to claim 13, wherein the compound is used as a material for the hole transport layer.

15. The organic electronic device according to claim 13, wherein the compound is used as a material for the light-emission assisting layer.

16. The organic electronic device according to claim 13, wherein the compound is used as a phosphorescent host material for the light-emitting layer.

17. The organic electronic device according to claim 12, wherein the organic electronic device further includes a light efficiency enhancing layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

18. The organic electronic device according to claim 12, wherein the organic material layer includes two or more stacked bodies, the stacked bodies including a hole transport layer, a light-emitting layer, and an electron transport layer formed in sequence on the anode.

19. The organic electronic device according to claim 18, wherein the organic material layer further includes a charge generation layer formed between the two or more stacked bodies.

20. Electronic device, comprising: A display device including the organic electronic element according to claim 12; And a control unit for driving the display device.

21. The electronic device according to claim 20, wherein the organic electronic element is any one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white illumination.

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