Compound for organic electronic element, organic electronic element using the compound, and electronic device thereof

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and service life of an element, an organic electronic element using the compound and an electronic device thereof.

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 an organic material layer in an organic electronic element 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] Lifespan and efficiency are the biggest issues for organic light-emitting diodes, and as displays become larger, these efficiency and lifespan issues must be addressed. Efficiency, lifespan, and driving voltage are related to each other, and when efficiency increases, driving voltage decreases relatively, and as driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, and thus lifespan tends to increase.

[0005] However, efficiency cannot be maximized simply by improving the organic material layer. This is because long service life and high efficiency can be achieved simultaneously 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] Furthermore, recently, in organic electroluminescent devices, in order to solve the emission problem in the hole transport layer, an emission auxiliary layer must exist between the hole transport layer and the emission layer, and different emission auxiliary layers need to be developed according to each emission layer (R, G, B).

[0007] Generally, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, thereby generating excitons through recombination.

[0008] However, the material for the hole transport layer has a low HOMO value and thus mainly has a low T1 value, so excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge imbalance in the emission layer and light emission at the interface of the hole transport layer.

[0009] When light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device are reduced, and the service life is shortened. Therefore, it is urgent to develop an emission 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 emission layer.

[0010] At the same time, it is necessary to develop hole injection layer materials that have stable characteristics, i.e., high glass transition temperature, to resist the Joule heat generated when the device is driven, while delaying the penetration 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 devices. The low glass transition temperature of the hole transport layer material has the following characteristics: when the device is driven, the uniformity of the film surface is reduced, which is reported to have a great influence on the service life of the device. In addition, OLED devices are mainly formed by a deposition method, and it is necessary to develop materials that can withstand long-term deposition, i.e., materials with high heat resistance characteristics.

[0011] That is, in order to fully demonstrate the excellent properties of organic electronic components, the materials used to form the organic material layer in the component (such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, emission auxiliary layer materials) should be supported by stable and effective materials. However, such stable and effective organic material layer materials for organic electronic components have not been fully developed. Therefore, there is a continuous need to develop new materials, and there is an urgent need to develop materials for hole transport layers or emission auxiliary layers. Summary of the invention

[0012] In order to solve the above-mentioned problems of the background technology, the present invention discloses a compound with a new structure, and when the compound is applied to an organic electronic element, the luminous efficiency, stability and service life of the element are greatly improved.

[0013] 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.

[0014] Technical Solution

[0015] The present invention provides a compound represented by Formula 1.

[0016] <Formula 1>

[0017]

[0018] In another aspect, the present invention provides an organic electronic element including the compound represented by Formula 1 and an electronic device thereof.

[0019] Effects of the Invention

[0020] 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

[0021] Figures 1 to 3 Examples of the organic electronic element according to the present invention are illustrated.

[0022] Figure 4 A formula according to one aspect of the present invention is shown.

[0023] 100, 200, 300: organic electronic element 110: first electrode

[0024] 120: hole injection layer 130: hole transport layer

[0025] 140: Emission layer 150: Electron transport layer

[0026] 160: electron injection layer 170: second electrode

[0027] 180: Light efficiency enhancement layer 210: Buffer layer

[0028] 220: emission auxiliary layer 320: first hole injection layer

[0029] 330: first hole transport layer 340: first emission layer

[0030] 350: first electron transport layer 360: first charge generation layer

[0031] 361: second charge generation layer 420: second hole injection layer

[0032] 430: second hole transport layer 440: second emission layer

[0033] 450: Second electron transport layer CGL: Charge generation layer

[0034] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0035] 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.

[0036] 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.

[0037] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0038] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] Unless otherwise specified, the term “alkoxy,” “alkoxy group,” or “alkyloxy group” as used herein means an oxy group attached to an alkyl group and has 1 to 60 carbon atoms, but is not limited thereto.

[0043] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means an oxy group connected to an aryl group and has 6 to 60 carbon atoms, but is not limited thereto.

[0044] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. Herein, aryl groups or arylene groups mean monocyclic and polycyclic aromatic groups, and may also be formed by combining with adjacent groups. Examples of "aryl groups" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0045] 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.

[0046] 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.

[0047] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms (but not limited thereto), has 2 to 60 carbon atoms, includes any one of a monocyclic and polycyclic ring, and may include a heteroaliphatic ring and / or a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

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

[0049] In addition, the term "heterocyclic group" may include SO 2 A ring replacing a carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0050]

[0051] 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.

[0052]

[0053] 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 atoms in the compound.

[0054] 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.

[0055] 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.

[0056] In addition to the above-mentioned hetero compounds, other hetero compounds or hetero groups contain one or more hetero atoms, but are not limited thereto.

[0057] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substitution is substituted by at least one substituent 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, C 6 -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 not limited thereto.

[0058] Unless expressly stated otherwise, the formulae for the present invention as used herein apply in the same manner as the definition of substituents according to the definition of the exponents of the formulae below.

[0059]

[0060] When a is an integer equal to zero, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 When a is an integer of 2 or 3, each substituent R 1may be the same or different, and when a is an integer of 4 to 6, is connected to the benzene ring in a similar manner, but indication of hydrogen bonded to carbon forming the benzene ring is omitted.

[0061]

[0062] Hereinafter, a compound according to aspects of the present invention and an organic electronic element including the compound will be described.

[0063] The present invention provides a compound represented by Formula 1.

[0064] <Formula 1>

[0065]

[0066] Among them, each symbol can be defined as follows.

[0067] 1) X is O or S,

[0068] 2) L 1 and L 2 Each independently selected from C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring condensed ring group; C 2 -C 60 Heterocyclic groups;

[0069] When L 1 and L 2 When it is an arylene group, it is preferably C 6 -C 30 Arylene groups, more preferably C 6 -C 24 Arylene groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0070] When L 1 and L 2 When it is a fused ring group, it is preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 A fused aromatic ring group, and more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused ring group,

[0071] When L 1 and L 2 When it is a heterocyclic group, it is preferably C2 -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, phenothiazine, phenylphenothiazine, and the like.

[0072] 3) Ar 1 ,Ar 2 ,Ar 3 and Ar 4 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 condensed ring group; C 1 -C 60 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; C 6 -C 30 an aryloxy group; and -L 3 -Ar;

[0073] When Ar 1 ,Ar 2 ,Ar 3 and Ar 4 When it is an aryl group, it is preferably C 6 -C 30 Aryl groups, more preferably C 6 -C 25 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0074] When Ar 1 ,Ar 2 ,Ar 3 and Ar 4 When it is a fluorenyl group, it is preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorene, or the like.

[0075] When Ar 1 ,Ar2 ,Ar 3 and Ar 4 When it is a heterocyclic group, it is preferably 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, phenothiazine, phenylphenothiazine, and the like.

[0076] When Ar 1 ,Ar 2 ,Ar 3 and Ar 4 When it is a fused ring group, it is preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused group.

[0077] When Ar 1 ,Ar 2 ,Ar 3 and Ar 4 When it is an alkyl group, it is preferably C 1 -C 30 Alkyl groups, more preferably C 1 -C 24 Alkyl group.

[0078] 4) L 3 Selected from single bonds; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Aliphatic ring; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups; and combinations thereof.

[0079] When L 3 When it is an arylene group, it is preferably C 6 -C 30 Arylene groups, more preferably C 6 -C 24 Arylene groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0080] When L 3 When it is an aliphatic ring, it may preferably be C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0081] When L 3 When it is a heterocyclic group, it is preferably 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, phenothiazine, phenylphenothiazine, and the like.

[0082] 5) Ar is 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 groups;

[0083] When Ar is an aryl group, it is preferably C 6 -C 30 Aryl groups, more preferably C 6 -C 25 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0084] When Ar is a fluorenyl group, it is preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorene, and the like.

[0085] When Ar is a heterocyclic group, it is preferably 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, phenothiazine, phenylphenothiazine, and the like.

[0086] When Ar is a fused ring group, it is preferably C3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused group.

[0087] 6) R 1 and R 2 are the same as or different from each other and are each independently selected from hydrogen; deuterium; tritium; 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 condensed ring group; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b );

[0088] When R 1 and R 2 When it is an aryl group, it is preferably C 6 -C 30 Aryl groups, more preferably C 6 -C 25 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0089] When R 1 and R 2 When it is a fluorenyl group, it is preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorene, or the like.

[0090] When R 1 and R 2 When it is a heterocyclic group, it is preferably 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, phenothiazine, phenylphenothiazine, and the like.

[0091] When R 1 and R 2 When it is a fused ring group, it is preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring fused group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused group.

[0092] When R 1 and R 2 When it is an alkyl group, it is preferably C 1 -C 30 Alkyl groups, more preferably C 1 -C 24 Alkyl group.

[0093] 7) a is an integer from 0 to 4, b is an integer from 0 to 2,

[0094] 8) If a and b are 2 or greater, multiple R 1 and R 2 Each of the same or different adjacent R 1 or multiple R 2 can be bonded to each other to form a ring,

[0095] 9) L' is selected from a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Aliphatic ring; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; and combinations thereof, wherein R a and R b Each independently selected from C 6 -C 60 Aryl group; Fluorenyl group; C 3 -C 60 Aliphatic ring; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups; and combinations thereof,

[0096] Wherein if L' is an arylene group, it is preferably C 6 -C 30 Arylene groups, more preferably C 6 -C 24 Arylene groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0097] Where L' is an aliphatic ring, it may preferably be C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0098] Wherein if L' is a heterocyclic group, it is preferably 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, phenothiazine, phenylphenothiazine, and the like.

[0099] Where R a and R b is an aryl group, which is preferably C 6 -C 30 Aryl groups, more preferably C 6 -C 25 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0100] Where R a and R b is a fluorenylene group, which may be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene.

[0101] Where R a and R b is an aliphatic ring, which may preferably be C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0102] Where R a and R b is a heterocyclic group, which is preferably C 2 -C 30 A heterocyclic group, and more preferably C 2 -C 24Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, and the like.

[0103] 10) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring, condensed ring group, alkyl group, alkenyl 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; C 1 -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 Arylalkenyl group; and 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, C 6 -C 60 Aromatic ring or C 2 -C 60 A heterocyclic group or a condensed ring formed by combining them.

[0104] In addition, the compound represented by Formula 1 is represented by any one of the following Formula 1-1 to Formula 1-4.

[0105]

[0106] Among them, X, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 , L 1 , L2 , R 1 , R 2 , a and b are the same as defined in Formula 1.

[0107] In addition, the compound represented by Formula 1 is represented by Formula 2.

[0108] <Formula 2>

[0109]

[0110] in,

[0111] 1) X, Ar 2 ,Ar 3 ,Ar 4 , L 1 , L 2 , L 3 , R 1 , R 2 , a and b are the same as those defined in Formula 1,

[0112] 2)X 1 and X 2 Each independently is a single bond, NR, O, S or CR'R", excluding when X 1 and X 2 When it is a single key,

[0113] 3) R, R', R", R 3 and R 4 With R in formula 1 1 The same as defined above, R' and R" are bonded to each other to form a spiro ring, and adjacent multiple R 3 or multiple R 4 can be bonded to each other to form a ring,

[0114] 4) c is an integer from 0 to 3, and d is an integer from 0 to 4.

[0115] In addition, Ar 1 ,Ar 2 ,Ar 3 or Ar 4 It is represented by any one of the following formulas A-1 to A-5.

[0116]

[0117] in,

[0118] 1) Z 1 and Z 2 Each independently is NR, O, S or CR'R",

[0119] 2) R, R' and " are the same as defined in Formula 2,

[0120] 3) Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 16 , Y 17 and Y 18 Each is independently C-* or C(R c ),

[0121] 4) R c With R in formula 1 1 The definition is the same as

[0122] 5) In formula A-1 and formula A-2, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 At least one of them is C-*,

[0123] 6) In Formula A-3 to Formula A-5, Y 9 , Y 10 , Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 16 , Y 17 and Y 18 At least one of them is C-*,

[0124] 7) * indicates the binding position with N.

[0125] In addition, the compound represented by Formula 1 is represented by any one of Formula 3-1 to Formula 3-3.

[0126]

[0127] in,

[0128] 1) X, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4, L 2 , R 1 , R 2 , a and b are the same as those defined in Formula 1,

[0129] 2) R 5 , R 6 and R 7 With R in formula 1 1 The definition of is the same, and multiple adjacent R 5 or multiple R 6 , multiple R 7 can be bonded to each other to form a ring,

[0130] 3) e and f are each independently an integer of 0 to 4, and g is an integer of 0 to 6.

[0131] In addition, the compound represented by Formula 1 is represented by Formula 4.

[0132] <Formula 4>

[0133]

[0134] in,

[0135] 1) X, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 , R 1 , R 2 , a and b are the same as those defined in Formula 1,

[0136] 2) R 5 and e are the same as those defined in Formula 3-1,

[0137] 3) R 8 With R in formula 1 1 The definition of is the same, and multiple R 8 can be bonded to each other to form a ring,

[0138] 4)h is an integer from 0 to 4.

[0139] In addition, the compound represented by Formula 1 is represented by any one of the following Compound P-1 to Compound P-84.

[0140]

[0141]

[0142]

[0143]

[0144] refer to Figure 1The 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 more compounds represented by Formula 1 or Formula 2. Here, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode. In the case of an inverted organic electronic element, the first electrode may be a cathode, and the second electrode may be an anode.

[0145] The organic material layer may include a hole injection layer (120), a hole transport layer (130), an emission layer (140), an electron transport layer (150), and an electron injection layer (160) formed in sequence on the first electrode (110). Here, the remaining layers except the emission layer (140) may not be formed. The organic material layer may also include a hole blocking layer, an electron blocking layer, an emission 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 ).

[0146] 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 formed 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 material for a hole injection layer (120), a hole transport layer (130), an emission auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a host or dopant of an emission layer (140), or a material for 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 an emission auxiliary layer or a hole transport layer.

[0147] The organic material layer may include two or more stacks including a hole transport layer, an emission 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 ).

[0148] In addition, even if the same core is used, the band gap, electrical properties, interface properties, etc. may vary depending on the position where the substituent is bonded, so the selection of the combination of the core and the substituents connected thereto 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.

[0149] 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), an emission 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.

[0150] 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 a compound as an electron transport material.

[0151] 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.

[0152] In addition, the present invention provides an emission assisting layer composition including the compound represented by Formula 1, and provides an organic electronic element including the emission assisting layer.

[0153] In addition, the present invention provides a hole transport layer composition including the compound represented by Formula 1, and provides an organic electronic element including the hole transport layer.

[0154] In addition, the present invention provides a light efficiency enhancing layer composition including the compound represented by Formula 1, and provides an organic electronic element including the light efficiency enhancing layer.

[0155] 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.

[0156] 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.

[0157] Hereinafter, a synthesis example of the compound represented by Formula 1 of the present invention and a preparation example of the organic electronic element of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0158] [Synthesis example]

[0159] The compound (final product) represented by Formula 1 according to the present invention can be prepared by reacting as in Reaction Scheme 1, but is not limited thereto. (Hal 1 is Br, I or Cl)

[0160] <Reaction Scheme 1>

[0161]

[0162] I. Synthesis of Sub 1

[0163] Sub 1 of Reaction Scheme 1 can be synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0164] <Reaction Scheme 2>

[0165]

[0166] Sub 1-a of Reaction Scheme 2 can be synthesized through the reaction path of Reaction Scheme 2-1 or Reaction Scheme 2-2, but is not limited thereto.

[0167] <Reaction Scheme 2-1>

[0168]

[0169] <Reaction Scheme 2-2>

[0170]

[0171] 1. Synthesis example of Sub1-1

[0172]

[0173] After Sub1-b-1 (8.3 g, 28.7 mmol) was placed in a round-bottom flask and dissolved in THF (126 mL) and water (42 mL), Sub1-2a-1 (8.8 g, 31.9 mmol), Pd(PPh 3 ) 4 (1.0 g, 0.9 mmol), NaOH (52.6 g, 57.4 mmol) and stirred at 75 °C. When the reaction was complete, the mixture was washed with CH 2 Cl 2 The organic layer was extracted with water and MgSO 4It was dried, concentrated, and the resulting compound was recrystallized by a silica gel column to obtain 7.8 g (yield: 61%) of a product.

[0174] 2. Synthesis example of Sub1-8

[0175]

[0176] After Sub1-b-2 (7.2 g, 18.2 mmol) was placed in a round-bottom flask and dissolved in THF (108 mL) and water (27 mL), Sub1-2a-2 (5.6 g, 19.9 mmol), Pd(PPh 3 ) 4 (0.6 g, 0.6 mmol), NaOH (33.4 g, 36.4 mmol) and used to synthesize Sub 1-1 to obtain 5.9 g (yield: 59%) of the product.

[0177] 3. Synthesis example of Sub1-34

[0178]

[0179] After Sub1-b-3 (8.6 g, 29.6 mmol) was placed in a round-bottom flask and dissolved in THF (130 mL) and water (33 mL), Sub1-2a-3 (9.1 g, 32.3 mmol), Pd(PPh 3 ) 4 (1.03 g, 0.9 mmol), NaOH (54.3 g, 59.3 mmol) and used to synthesize Sub 1-1 to obtain 8.6 g (yield: 65%) of the product.

[0180] 4. Synthesis example of Sub1-71

[0181]

[0182] After Sub1-b-4 (7.4 g, 17.5 mmol) was placed in a round-bottom flask and dissolved in THF (112 mL) and water (28 mL), Sub1-1a-1 (5.7 g, 19.1 mmol), Pd(PPh 3 ) 4 (0.6 g, 0.5 mmol), NaOH (32.1 g, 35.1 mmol) and used to synthesize Sub 1-1 to obtain 7.0 g (yield: 67%) of the product.

[0183] 5. Synthesis example of Sub1-92

[0184]

[0185] After Sub1-b-5 (9.0 g, 26.5 mmol) was placed in a round-bottom flask and dissolved in THF (135 mL) and water (34 mL), Sub1-1a-2 (8.6 g, 28.9 mmol), Pd(PPh 3 ) 4 (0.9 g, 0.8 mmol), NaOH (48.6 g, 53.1 mmol) and used to synthesize Sub 1-1 to obtain 8.7 g (yield: 64%) of the product.

[0186] 6. Synthesis example of Sub1-103

[0187]

[0188] After Sub1-b-6 (8.1 g, 23.9 mmol) was placed in a round-bottom flask and dissolved in THF (122 mL) and water (31 mL), Sub1-1a-3 (9.1 g, 26.0 mmol), Pd(PPh 3 ) 4 (0.8 g, 0.7 mmol), NaOH (43.7 g, 47.8 mmol) and used to synthesize Sub 1-1 to obtain 8.8 g (yield: 66%) of the product.

[0189] Meanwhile, the compound belonging to Sub 1 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 Sub 1.

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] [Table 1]

[0196]

[0197]

[0198]

[0199]

[0200] II. Synthesis of Sub 2

[0201] Sub 2 of Reaction Scheme 1 can be synthesized through the reaction path of Reaction Scheme 3, but is not limited thereto.

[0202] <Reaction Scheme 3>

[0203]

[0204] The synthesis examples of specific compounds belonging to Sub 2 are as follows.

[0205] 1. Synthesis example of Sub 2-2

[0206]

[0207] 1) Synthesis of Sub2-c-1

[0208] Combine Sub2-a-1 (11.4g, 48.9mmol), Sub2-b-1 (8.3g, 48.9mmol), Pd 2 (dba) 3 (1.3 g, 1.5 mmol), P(t-Bu) 3 (50 wt% solution) (1.2 mL, 2.9 mmol), NaOt-Bu (14.1 g, 146.7 mmol), toluene (250 mL) were added to a round bottom flask and stirred at 80 °C. When the reaction was complete, the mixture was washed with CH 2 Cl 2 The organic layer was extracted with water and MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized by a silica gel column to obtain 13.5 g (yield: 86%) of a product.

[0209] 2) Synthesis of Sub2-2

[0210] Combine Sub2-c-1 (13.5g, 42.0mmol), Sub2-d-1 (6.6g, 42.0mmol), Pd 2 (dba) 3 (1.2 g, 1.3 mmol), P(t-Bu) 3 (50wt% solution) (1.02mL, 0.5mmol), NaOt-Bu (12.1g, 126.0mmol), toluene (280mL) were added to a round-bottom flask, and 15.2g (yield: 82%) of the product was obtained using the Sub2-c-1 synthesis method.

[0211] 2. Synthesis example of Sub 2-6

[0212]

[0213] 1) Synthesis of Sub2-c-2

[0214] Combine Sub2-a-2 (13.0g, 49.4mmol), Sub2-b-2 (4.6g, 49.4mmol), Pd 2 (dba) 3 (1.4 g, 1.5 mmol), P(t-Bu) 3 (50wt% solution) (1.2mL, 3.0mmol), NaOt-Bu (14.2g, 148.2mmol), toluene (260mL) were added to a round-bottom flask, and 11.4g (yield: 84%) of the product was obtained using the Sub2-c-1 synthesis method.

[0215] 2) Synthesis of Sub2-6

[0216] Combine Sub2-c-2 (11.4g, 41.4mmol), Sub2-d-2 (6.5g, 41.4mmol), Pd 2 (dba) 3 (1.1 g, 1.2 mmol), P(t-Bu) 3 (50wt% solution) (1.0 mL, 2.5 mmol), NaOt-Bu (11.9 g, 124.2 mmol), and toluene (250 mL) were added to a round-bottom flask, and 14.2 g (yield: 87%) of the product was obtained using the Sub2-c-1 synthesis method.

[0217] Meanwhile, the compound belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compound belonging to Sub 2.

[0218]

[0219]

[0220]

[0221]

[0222] [Table 2]

[0223]

[0224]

[0225]

[0226] III. Synthesis of the final product

[0227] 1. Synthesis Example of P-6

[0228]

[0229] After Sub2-6 (7.6 g, 19.2 mmol) was placed in a round-bottom flask and dissolved in THF (120 mL) and water (40 mL), Sub1-1 (9.3 g, 20.9 mmol), Pd(PPh 3 ) 4 (0.7 g, 0.6 mmol), NaOH (35.2 g, 38.5 mmol) and stirred at 75°C. When the reaction was complete, the mixture was washed with CH 2 Cl 2 The organic layer was extracted with water and MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized by a silica gel column to obtain 9.5 g (yield: 65%) of a product.

[0230] 2. Synthesis Example of P-17

[0231]

[0232] After Sub2-19 (8.4 g, 24.8 mmol) was placed in a round-bottom flask and dissolved in THF (126 mL) and water (42 mL), Sub1-25 (15.3 g, 27.0 mmol), Pd(PPh 3 ) 4 (0.86 g, 0.7 mmol), NaOH (45.4 g, 49.5 mmol) and the P-6 synthesis method was used to obtain 13.5 g (yield: 66%) of the product.

[0233] 3. Synthesis Example of P-58

[0234]

[0235] After Sub2-64 (6.8 g, 15.8 mmol) was placed in a round-bottom flask and dissolved in THF (102 mL) and water (34 mL), Sub1-92 (8.84 g, 17.3 mmol), Pd(PPh 3 ) 4 (0.6 g, 0.5 mmol), NaOH (29.0 g, 31.7 mmol) and the P-6 synthesis method was used to obtain 8.5 g (yield: 63%) of the product.

[0236] Meanwhile, the FD-MS values ​​of Compound P-1 to Compound P-84 of the present invention prepared according to the Synthesis Examples as described above are shown in Table 3.

[0237] [Table 3]

[0238]

[0239]

[0240] Fabrication and evaluation of organic electronic components

[0241] [Example 1] Green organic light-emitting diode (emission auxiliary layer)

[0242] An organic electroluminescent device is manufactured using the compound of the present invention as an emission auxiliary layer material according to a conventional method. First, after 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter, 2-TNATA) is vacuum deposited on an ITO layer (anode) formed on a glass substrate to a thickness of 60 nm to form a hole injection layer, N,N'-bis(1-naphthyl)-N,N'-bisphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter, NPB) is vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer.

[0243] Then, the compound P-1 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form an emission auxiliary layer, and 4,4'-N,N'-dicarbazole-biphenyl (hereinafter, CBP) as a host material and bis(1-phenylisoquinolyl)iridium(III) acetylacetonate (hereinafter, (piq)) as a dopant material were added. 2 Ir(acac)) was doped on the emission auxiliary layer at a weight ratio of 95:5 and then vacuum deposited to a thickness of 30 nm to form an emission layer. Then, (1,1'-biphenyl-4-ato)bis(2-methyl-8-quinolinato)aluminum (hereinafter, BAlq) was vacuum deposited on the emission layer to a thickness of 10 nm to form a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter, Alq) was vacuum deposited on the hole blocking layer to a thickness of 10 nm. 3 ) was vacuum deposited to a thickness of 40 nm to form an electron transport layer. Then, alkali metal halide LiF was deposited to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting diode.

[0244] [Example 2] to [Example 12] Red organic light emitting diode (emission auxiliary layer)

[0245] An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 4 were used instead of the compound P-1 of the present invention as the emission assisting layer material.

[0246] [Comparative Example 1] to [Comparative Example 3]

[0247] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Compounds 1 to 3 described in Table 4 were used instead of P-1 of the present invention as an emission auxiliary layer material.

[0248]

[0249]

[0250] By applying a forward bias DC voltage to the organic light emitting diodes prepared according to Examples 1 to 12 of the present invention and Comparative Examples 1 to 3, the electroluminescence (EL) characteristics were measured by PR-650 of Photoresearch, and the lifetime measurement equipment manufactured by McScience at 2500 cd / m 2 The T95 lifetime was measured at a brightness of , and the measurement results are shown in Table 4.

[0251] [Table 4]

[0252]

[0253]

[0254] According to the results in Table 4, when a red organic light-emitting diode is manufactured by using the material for an organic light-emitting diode of the present invention as an emission auxiliary layer material, it can be seen that not only the driving voltage of the organic light-emitting diode can be reduced, but also the luminous efficiency and service life can be significantly improved compared with the comparative examples using comparative compounds 1 to 3. In detail, the comparative compound and the compound of the present invention are similar in that dibenzofuran or dibenzothiophene is replaced with two amine groups, but there are differences in the binding position of the amine group and whether there is a connecting group between dibenzofuran or dibenzothiophene and the amine group.

[0255] First, the device results of Comparative Compound 2, in which two amine groups are substituted on the same benzene ring of dibenzofuran, are superior to those of Comparative Compound 1, in which the amine groups are substituted by directly bonding to different benzene rings of dibenzofuran. These results indicate that when two amine groups are bonded to the same ring of dibenzofuran, the overall Hall characteristics increase, and while the distance between the materials remains constant, the interaction with the adjacent layers can proceed smoothly, thus improving the efficiency and lifetime while reducing the overall driving voltage.

[0256] In addition, the element results of comparative compound 3, which is similar to comparative compound 2 but has one amine group directly bonded to dibenzofuran and another amine group bonded to phenyl (linking group), are further improved, and it can be confirmed that the results of the compound of the present invention, which is characterized in that 2 linking groups are bonded to dibenzofuran or dibenzothiophene and amine groups are bonded to each linking group, are significantly better than those of comparative compound 3.

[0257] These results show that by introducing a linker, the physical properties change as the conjugation length increases, and among them, the Hall characteristics are further increased, so that the overall performance of the element is significantly improved. First, it is judged that the stability of the unshared electron pair of dibenzofuran or dibenzothiophene is further maximized by introducing an additional linker between dibenzofuran or dibenzothiophene and the amine group, so that significantly excellent element results are obtained when the compound of the present invention is used.

[0258] In summary, it shows that the physical properties of the compounds (such as hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection and mobility characteristics, and electron blocking characteristics) vary depending on the binding position of the substituent and the presence or absence of the linking group, which may lead to completely different element results.

[0259] In the case of an emission-assisting layer, the relationship between the hole transport layer and the emission layer (host) needs to be understood, and it is difficult for those skilled in the art to infer the characteristics of an emission-assisting layer using the compounds of the present invention even if similar cores are used.

[0260] Furthermore, although the device characteristics in which the compound of the present invention is applied only to one emission assisting layer are described in the evaluation results of the above device fabrication, the case where the compound of the present invention is used to form a hole transport layer or both a hole transport layer and an emission assisting layer may also be applicable.

[0261] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be understood 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. The scope of the present invention should be interpreted based on the appended claims, and should be interpreted as all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0262] Industrial Applicability

[0263] According to the present invention, an organic device having excellent device characteristics of high brightness, high luminescence, and long lifespan can be manufactured, and thus there is industrial applicability.

Claims

1. A compound represented by Formula 1: <Formula 1> in: 1) X is O or S, 2) L 1 and L 2 each independently selected from phenylene, biphenylene, naphthylene and terphenylene; 3) Ar 1 ,Ar 2 ,Ar 3 and Ar 4 Each independently selected from C6-C 30 Aryl group; Fluorenyl group; C2-C 24 heterocyclic group; and -L 3 -Ar; 4) L 3 Selected from C6-C 30 Arylene group, 5) Ar is selected from C6-C 30 Aryl group; C2-C 24 Heterocyclic groups; 6) R 1 and R 2 are the same as or different from each other and are each independently selected from hydrogen; deuterium; phenyl; biphenyl; and naphthyl; 7) a is an integer from 0 to 4, b is an integer from 0 to 2, 8) If a and b are 2 or greater, multiple R 1 and R 2 Each of the same or different adjacent R 1 can be bonded to each other to form a ring, 9) Among them, The aryl group, the arylene group, the heterocyclic group and the fluorenyl group may be substituted with one or more substituents selected from deuterium; fluorine; a cyano group; a C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group.

2. The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-4: in, X、Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 , L 1 , L 2 , R 1 , R 2 , a and b are the same as defined in claim 1.

3. The compound according to claim 1, wherein Formula 1 is represented by Formula 2: <Formula 2> in: 1) X, Ar 2 ,Ar 3 ,Ar 4 , L 1 , L 2 , L 3 , R 1 , R 2 , a and b are the same as defined in claim 1, 2)X 1 and X 2 Each independently is a single bond, NR, O, S or CR'R", excluding when X 1 and X 2 When it is a single key, 3) R, R', R", R 3 and R 4 are each independently selected from hydrogen, deuterium and C1-C 20 an alkyl group, R' and R" are bonded to each other to form a spiro ring, 4) c is an integer from 0 to 3, and d is an integer from 0 to 4.

4. The compound of claim 1, wherein Ar 1 ,Ar 2 ,Ar 3 or Ar 4 It is represented by any one of the following formulas A-1 to A-5: in: 1) Z 1 and Z 2 Each independently is NR, O, S or CR'R", 2) R, R' and R" are the same as defined in claim 3, 3) Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 and Y 18 are each independently C-* or C(R c ) 4) R c is hydrogen, deuterium or C1-C 20 Alkyl groups, 5) In formula A-1 and formula A-2, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 At least one of them is C-*, 6) In Formula A-3 to Formula A-5, Y 9 , Y 10 , Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 16 , Y 17 and Y 18 At least one of them is C-*, 7) * indicates the binding position with N.

5. The compound according to claim 1, wherein Formula 1 is represented by any one of Formula 3-1 to Formula 3-3: in: 1) X, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 , L 2 , R 1 , R 2 , a and b are the same as defined in claim 1, 2) R 5 , R 6 and R 7 are each independently selected from hydrogen, deuterium and C1-C 20 Alkyl groups, 3) e and f are each independently an integer of 0 to 4, and g is an integer of 0 to 6.

6. The compound according to claim 1, wherein Formula 1 is represented by Formula 4: <Formula 4> in: 1) X, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 , R 1 , R 2 , a and b are the same as defined in claim 1, 2) R 5 and e is the same as defined in claim 5, 3) R 8 is hydrogen, deuterium or C1-C 20 Alkyl groups, 4)h is an integer from 0 to 4.

7. A compound represented by any one of the following compounds P-1 to P-84, 8 . An organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound or two or more compounds according to claim 1 . 9 . The organic electronic element of claim 8 , wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer, an emission layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

10. The organic electronic element according to claim 8, wherein the organic material layer is an emission assisting layer.

11. The organic electronic element according to claim 8, wherein the organic material layer is a hole transport layer. 12 . The organic electronic element of claim 8 , wherein the organic electronic device further comprises a light efficiency enhancement layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

13. The organic electronic element as claimed in claim 8, wherein the organic material layer is a light efficiency enhancing layer. 14 . The organic electronic element according to claim 8 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode. 15 . The organic electronic element according to claim 14 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies.

16. An electronic device comprising a display device including the organic electronic element according to claim 8; and a control unit for driving the display device. 17 . The electronic device of claim 16 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white lighting.

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