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

Abstract

The present invention provides an organic electronic element and an electronic device including the organic electronic element, wherein the organic electronic element includes a positive electrode, a negative electrode, and an organic material layer arranged between the positive electrode and the negative electrode. The organic material layer includes a compound represented by Formula 1, Formula 2, or Formula 3 of the present invention, thereby reducing the driving voltage and improving the luminous efficiency and service life of the organic electronic element.

Description

Technical Field

[0001] The present invention relates to an organic electronic element including a compound for an organic electronic element 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, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

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

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

[0005] Lifespan and efficiency are the biggest issues for organic electroluminescent 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.

[0006] Short-wavelength dopants are used as a method to improve the maximum luminous efficiency. Short-wavelength dopants have higher maximum luminous efficiency than existing long-wavelength dopants, so they can be used to improve the overall device efficiency. However, the x color coordinate is very low, which is disadvantageous in terms of color purity. In order to solve these shortcomings, it is necessary to shift the maximum emission wavelength to a host with a longer wavelength, and this host not only affects the maximum emission efficiency but also the service life.

[0007] However, efficiency cannot be maximized simply by improving the organic material layer. This is because, 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, long service life and high efficiency can be achieved simultaneously. Therefore, it is necessary to develop materials with high thermal stability and capable of effectively balancing the charges in the light-emitting layer. That is, in order to fully demonstrate the excellent properties of organic electronic components, priority should be given to materials that are competent for forming the organic material layers in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. However, the development of stable and effective organic material layer materials for organic electronic components has not yet been fully realized. Therefore, there is a continuous need to develop new materials, and specifically, there is an urgent need to develop host materials for the light-emitting layer. Summary of the invention

[0008] An object of the present invention is to provide an organic electronic element and an electronic device thereof including a compound capable of reducing the driving voltage of the element and improving the luminous efficiency, color purity, stability and service life of the element.

[0009] [Technical solution]

[0010] In one aspect, the present invention provides an organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound represented by Formula 1; and a compound represented by Formula 2 or Formula 3.

[0011]

[0012] In another aspect, the present invention provides an electronic device comprising the organic electronic element.

[0013] [Effects of the invention]

[0014] 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

[0015] Figures 1 to 3is an exemplary view of an organic electroluminescent device according to the present invention.

[0016] 100, 200, 300: organic electronic element 110: first electrode

[0017] 120: hole injection layer 130: hole transport layer

[0018] 140: Light-emitting layer 150: Electron transport layer

[0019] 160: electron injection layer 170: second electrode

[0020] 180: Light efficiency enhancement layer 210: Buffer layer

[0021] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0022] 330: first hole transport layer 340: first light emitting layer

[0023] 350: first electron transport layer 360: first charge generation layer

[0024] 361: second charge generation layer 420: second hole injection layer

[0025] 430: second hole transport layer 440: second light emitting layer

[0026] 450: Second electron transport layer CGL: Charge generation layer

[0027] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0028] 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.

[0029] 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.

[0030] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0031] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] Unless otherwise specified, the term “alkoxy,” “alkoxy group,” or “alkyloxy group” as used herein means an alkyl group bonded to an oxy group, but is not limited thereto, and has 1 to 60 carbon atoms.

[0036] Unless otherwise specified, the term "aryloxy group" or "aryloxy group" as used herein means an aryl group bonded to an oxy group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0037] Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, but are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by connecting or reacting adjacent substituents.

[0038] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0039] 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.

[0040] 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.

[0041] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any of a monocyclic and polycyclic ring, and may include heteroaliphatic rings and heteroaromatic rings. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0042] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0043] In addition, the term "heterocyclic group" may include a ring containing SO2 instead of carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0044]

[0045] 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.

[0046]

[0047] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to the number of spiro atoms in the compound.

[0048] 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.

[0049] 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.

[0050] In addition to the above mentioned hetero compounds, other hetero compounds or hetero groups contain but are not limited to one or more hetero atoms.

[0051] In addition, unless otherwise specified, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterated C6-C 20 Aryl group, C8-C 20 Arylene groups, silane groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but are not limited to these substituents.

[0052] In addition, unless otherwise specifically explained, the formulae used in the present invention have the same definitions as those of the substituents defined by the indices in the following formulae.

[0053]

[0054] Here, when a is an integer of 0, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 Connected to any one of the carbon atoms constituting the benzene ring, when a is an integer of 2 or 3, each is combined as follows, wherein R 1 may be the same as or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, but indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

[0055]

[0056] In the following, reference will be made to the Figure 1 To Attachment Figure 3 Layer structures of organic electronic components comprising the compounds according to the invention are described.

[0057] When adding reference numbers to the components of each drawing, it should be noted that even if the same components are shown on different drawings, the same components should have the same numbers as much as possible. In addition, in describing the present invention, if it is determined that the detailed description of the related known configuration or function may confuse the main points of the present invention, the detailed description will be omitted.

[0058] Figures 1 to 3 is an exemplary view of an organic electronic element according to an embodiment of the present invention.

[0059] refer to Figure 1 , an organic electronic element (100) according to an embodiment of the present invention includes a first electrode (110), a second electrode (170) formed on a substrate (not shown), and an organic layer formed between the first electrode (110) and the second electrode (170).

[0060] The first electrode (110) may be an anode, the second electrode (170) may be a cathode, and in the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0061] The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160). Specifically, the hole injection layer (120), the hole transport layer (130), the light emitting layer (140), the electron transport layer (150), and the electron injection layer (160) may be sequentially formed on the first electrode (110).

[0062] Preferably, the light efficiency enhancement layer (180) can be formed on at least one surface of the first electrode (110) and the second electrode (170) that does not contact the organic material layer, and when the light efficiency enhancement layer (180) is formed, the light efficiency of the organic electronic element can be improved.

[0063] For example, a light efficiency enhancement layer (180) can be formed on the second electrode (170), and in the case of a top-emitting organic light-emitting device, the light efficiency enhancement layer (180) is formed to reduce light energy loss due to surface plasmon polaritons (SPP) in the second electrode (170), and in the case of a bottom-emitting organic light-emitting device, the light efficiency enhancement layer (180) can be used as a buffer for the second electrode (170).

[0064] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will be referred to in detail. Figure 2 Give a description.

[0065] refer to Figure 2 According to another embodiment of the present invention, an organic electronic device (200) includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) formed in sequence on a first electrode (110), and a light efficiency enhancement layer (180) is formed on the second electrode.

[0066] although Figure 2Although not shown, an electron transport auxiliary layer may be further formed between the light emitting layer (140) and the electron transport layer (150).

[0067] In addition, according to another embodiment of the present invention, the organic material layer may have a plurality of stacks including a hole transport layer, a light emitting layer and an electron transport layer. Figure 3 Give a description.

[0068] refer to Figure 3 In an organic electronic element (300) according to another embodiment of the present invention, 2 or more stacks (ST1 and ST2) made of a plurality of organic material layers may be formed between a first electrode (110) and a second electrode (170), and a charge generating layer (CGL) may be formed between the stacks of the organic material layers.

[0069] Specifically, the organic electronic element according to the embodiment of the present invention includes a first electrode (110), a first stack (ST1), a charge generation layer (CGL), a second stack (ST2), and a second electrode (170), and may include a light efficiency enhancement layer (180).

[0070] The first stack (ST1) is an organic material layer formed on the first electrode (110), and may include a first hole injection layer (320), a first hole transport layer (330), a first light emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light emitting layer (440), and a second electron transport layer (450). As described above, the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.

[0071] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). The charge generation layer (CGL) is formed between the first light emitting layer (340) and the second light emitting layer (440) to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.

[0072] When through Figure 3 When a plurality of light-emitting layers are formed by the multilayer stack structure method shown in FIG. 1 , an organic electronic element that emits white light by a mixing effect of light emitted from each light-emitting layer and an organic electronic element that emits light of various colors can be manufactured.

[0073] The compounds represented by Formula 1, Formula 2 and Formula 3 of the present invention can be used as materials for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), an electron injection layer (160), a light-emitting layer (140, 340, 440) or a light efficiency enhancement layer (180), but preferably, are used as the main body of the light-emitting layer (140, 340, 440).

[0074] Otherwise, even if the same or similar core is used, the band gap, electrical properties, interface properties, etc. may vary depending on what substituent is bonded at what position. Therefore, it is necessary to study the selection of the core and the combination of the sub-substituents bonded thereto, and in particular, when the 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 at the same time.

[0075] The organic electronic element according to the embodiment of the present invention can be manufactured using various deposition methods. It can be manufactured using a vapor deposition method such as PVD or CVD. For example, an anode (110) is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150) and an electron injection layer (160) is formed thereon. After that, an organic electroluminescent device according to the embodiment of the present invention can be manufactured by depositing a material that can be used as a cathode (170) thereon. In addition, a light-emitting auxiliary layer (220) can also be formed between the hole transport layer (130) and the light-emitting layer (140), and an electron transport auxiliary layer (not shown) can also be formed between the light-emitting layer (140) and the electron transport layer (150), and as described above, a stacked structure can be formed.

[0076] In addition, the organic material layer can be manufactured with a small number of layers by using various polymer materials and not by a deposition method, but by a solution process, a solvent process such as 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, a doctor blade process, a screen printing process or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0077] Furthermore, the organic electronic element according to an embodiment of the present invention may be selected from an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

[0078] Another embodiment of the present invention may include an electronic device including a display device including an organic electronic element; and a control unit for driving the display device. At this time, the electronic device may be a current or future wired / wireless communication terminal, 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 kinds of televisions, and various kinds of computers.

[0079] Hereinafter, an organic electronic element according to aspects of the present invention will be described.

[0080] The organic electronic element according to the present invention comprises a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3.

[0081]

[0082]

[0083] In Equations 1 to 3, each symbol can be defined as follows.

[0084] 1) L 1 is a substituent represented by any one of Formula L-1 to Formula L-4,

[0085]

[0086] 2) L 2 is a single bond; or C6-C 60 arylene groups;

[0087] Among them, L 2 In the case of an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C 24 The arylene group, for example, may be phenylene, biphenylene, naphthylene, phenanthrene or the like.

[0088] 3) L 3 , L 4 , L 5 and L 6 are each independently selected from a single bond; or C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups;

[0089] Among them, L 3 , L 4 , L 5 and L 6 In the case of an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C 24 The arylene group, for example, may be phenylene, biphenylene, naphthylene, terphenylene or the like.

[0090] Among them, L 3 , L 4 , L 5 and L 6 In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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] Among them, L 3 , L 4 , L 5 and L 6 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0092] 4) Ar is C6-C 60 Aryl groups, preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group may be, for example, phenylene, biphenylene, naphthalene, phenanthrene, and the like.

[0093] 5)Ar 1 ,Ar 2 and Ar 3 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups;

[0094] Among them, in Ar 1 ,Ar2 and Ar 3 In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0095] Among them, in Ar 1 ,Ar 2 and Ar 3 In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0096] Among them, in Ar 1 ,Ar 2 and Ar 3 In the case of a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0097] 6) Ar 4 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group; and -L'-NR b R c ;

[0098] Among them, in Ar 4 In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0099] Among them, in Ar 4 In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24The heterocyclic group, for example, may be 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.

[0100] Among them, in Ar 4 In the case of a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0101] 7) L' is each independently selected from a single bond; and C6-C 60 Arylene group; C2-C 60 Heterocyclic groups;

[0102] Where L' is an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C 24 The arylene group, for example, may be phenylene, biphenylene, naphthylene, terphenylene or the like.

[0103] Where L' is a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0104] 8) R a and R b Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Aliphatic ring and C6-C 60 A fused aromatic ring group; a C2-C 60 Heterocyclic group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 Aryloxy groups;

[0105] Among them, a and R b In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0106] Among them, a and R b In the case of a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0107] Among them, a and R b In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0108] Among them, a and R b In the case of an alkyl group, it is preferably C1-C 30 An alkyl group, and more preferably a C1-C 24 Alkyl group.

[0109] Among them, a and R b In the case of an alkoxy group, it is preferably C1-C 24 Alkoxy groups.

[0110] Among them, a and R b In the case of an aryloxy group, it is preferably C6-C 24 Aryloxy group.

[0111] 9) Ring A is a substituent represented by the following formula a; or formula b;

[0112]

[0113] 10) Ring B is C6-C 20 Aryl groups;

[0114] 11) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are independently hydrogen; or deuterium;

[0115] 12) R 8 and R 9 are the same or different and are independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy groups; and C6-C 60 Aryloxy group; or multiple adjacent R 8 or multiple R 9 can be bonded to each other to form a ring,

[0116] Among them, 8 and R 9 In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0117] Among them, 8 and R 9 In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0118] Among them, 8 and R 9 In the case of a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0119] Among them, 8 and R 9 In the case of an alkyl group, it is preferably C1-C 30 An alkyl group, and more preferably a C1-C 24 Alkyl groups,

[0120] Among them, 8 and R 9 In the case of an alkenyl group, it is preferably C2-C 30 Alkenyl groups, and more preferably C2-C 24 Alkenyl groups,

[0121] Among them, 8 and R 9 In the case of an alkynyl group, it is preferably C2-C 30 Alkynyl group, and more preferably C2-C 24 Alkynyl group,

[0122] Among them, 8 and R 9 In the case of an alkoxy group, it is preferably C1-C 30 Alkoxy groups, and more preferably C1-C 24 Alkoxy groups,

[0123] Among them, 8 and R 9 In the case of an aryloxy group, it is preferably C6-C 30 aryloxy group, and more preferably C6-C 24 Aryloxy groups,

[0124] 13) a and d are each independently an integer from 0 to 5, b and f are each independently an integer from 0 to 6, c, e, g, h, n and o are each independently an integer from 0 to 4, and i is an integer from 0 to 7,

[0125] 14) z is 0 or 1, provided that when z is 0, L 1 is a substituent represented by the formula L-4,

[0126] 15)Y is O, S, CR'R" or NR a ,

[0127] 16) wherein R' and R" are each independently selected from hydrogen; deuterium; C6-C 60Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 aryloxy group; alternatively, R' and R" may be bonded to each other to form a spiro ring,

[0128] Where R' and R" are aryl groups, they are preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0129] Where R' and R" are heterocyclic groups, they are preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0130] Where R' and R" are fused ring groups, they are preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0131] Where R' and R" are alkyl groups, they are preferably C1-C 30 An alkyl group, and more preferably a C1-C 24 Alkyl groups,

[0132] Where R' and R" are alkoxy groups, they are preferably C1-C 24 Alkoxy groups.

[0133] Where R' and R" are aryloxy groups, they are preferably C6-C 24 Aryloxy groups,

[0134] 17) R a It is C6-C60 or a C2-C ... 60 Heterocyclic groups;

[0135] Among them, a In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0136] Among them, a In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, may be 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.

[0137] 18)* indicates the position to be bonded,

[0138] 19) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; and C8-C 20 Arylalkenyl group; In addition, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by combining them.

[0139] L 2It can be represented by any one of the following formulas a-1 to a-20.

[0140]

[0141]

[0142] In the above formula a-1 to formula a-20, each symbol can be defined as follows.

[0143] 1) R 101 and R 102 are the same as or different from each other and each independently represents hydrogen; deuterium; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl groups;

[0144] Among them, 101 and R 102 In the case of aryl groups, they may be phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0145] 2) aa, ab and ac are each independently an integer from 0 to 4, ad is an integer from 0 to 6, and ae is an integer from 0 to 8,

[0146] 3)** indicates the position to be bonded.

[0147] Ar may be represented by any one of the following Formula b-1 to Formula b-8.

[0148]

[0149] In Formula b-1 to Formula b-8, each symbol can be defined as follows.

[0150] 1) R 103 It is hydrogen; deuterium; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl groups;

[0151] Among them, 103 In the case of an aryl group, it may be phenylene, biphenyl, naphthalene, terphenyl, or the like.

[0152] 2) ba is an integer from 0 to 5, bb is an integer from 0 to 7, bc is an integer from 0 to 9,

[0153] 3) It means the position bonded to L.

[0154] Formula L-1 can be represented by any one of the following Formulas L-1-1 to L-1-3:

[0155]

[0156]

[0157] Among them, R 5 , e and * are as defined above.

[0158] Formula L-2 can be represented by any one of the following Formulas L-2-1 to L-2-4:

[0159]

[0160] Among them, R 5 , f and * are as defined above.

[0161] Formula L-3 can be represented by any one of the following Formulas L-3-1 to L-3-8:

[0162]

[0163] Among them, R 5 , f and * are as defined above.

[0164] Formula L-4 can be represented by any one of the following Formulas L-4-1 to L-4-6:

[0165]

[0166] Among them, R 5 , R 6 , g, h and * are as defined above.

[0167] In addition, the compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2.

[0168]

[0169] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 1 , L 2 , Ar, a, b, c, d, g, h and i are as defined above.

[0170] The compound represented by Formula 1 is represented by Formula 1-1-a or Formula 1-1-b

[0171]

[0172] Where R 1 , R 2 , R 3 , R 7 , L1 , L 2 , Ar, a, b, c and i are as defined above.

[0173] The compound represented by Formula 1 is represented by any one of the following Formulas 1-1-1 to 1-1-5.

[0174]

[0175] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, c, d, e, f, g, h and i are as defined above.

[0176] The compound represented by Formula 1-1-1 is preferably represented by any one of the following Formulas 1-1-1-a to 1-1-1-c.

[0177]

[0178] Where R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and e are as defined above.

[0179] The compound represented by Formula 1-1-2 is preferably represented by any one of the following Formula 1-1-2-a to Formula 1-1-2-c.

[0180]

[0181]

[0182] Where R 1 , R 2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and f are as defined above.

[0183] The compound represented by Formula 1-1-3 is preferably represented by any one of the following Formula 1-1-3-a or Formula 1-1-3-b.

[0184]

[0185] Where R 1 , R2 , R 3 , R 4 , R 5 , L 2 , Ar, a, b, c, d and f are as defined above.

[0186] The compound represented by Formula 1-1-4 is preferably represented by Formula 1-1-4-a.

[0187]

[0188] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are as defined above.

[0189] Formula 1-1-4 can be more preferably represented by Formula 1-1-4-b or Formula 1-1-4-c.

[0190]

[0191] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 2 , Ar, a, b, c, d, g and h are as defined above.

[0192] Formula 1-1-5 can be preferably represented by any one of Formula 1-1-5-a to Formula 1-1-5-c.

[0193]

[0194] Where R 1 , R 2 , R 3 , R 5 , R 7 , L 2 , Ar, a, b, c, e and i are as defined above.

[0195] The compound represented by Formula 1 is represented by Formula 1-2-a.

[0196]

[0197]

[0198] Where R 1 , R 2, R 5 , R 6 , R 7 , L 2 , Ar, a, b, g, h and i are as defined above.

[0199] The compound represented by Formula 1 is represented by any one of Formula 1-2-b to Formula 1-2-d.

[0200]

[0201] Where R 1 , R 2 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, g, h and i are as defined above. The compound represented by Formula 2 is represented by any one of Formula 2-1 to Formula 2-3:

[0202]

[0203]

[0204] in,

[0205] 1) L 3 , L 4 , L 5 ,Ar 2 and Ar 3 As defined above,

[0206] 2)X 1 , X 2 and X 3 Same as the definition of Y,

[0207] 3) R 10 , R 11 , R 12 , R 13 , R 14 and R 15 With R 8 The definition is the same as

[0208] 4) p, r and t are each independently an integer from 0 to 4,

[0209] 5) q, s and u are each independently an integer from 0 to 3.

[0210] The compound represented by Formula 3 is represented by any one of Formula 3-1 to Formula 3-6:

[0211]

[0212]

[0213] in,

[0214] 1) Y, R 8 , R 9 , L 6 ,Ar 4 , n and o are as defined above,

[0215] 2) R 16 With R 8 The definition is the same as

[0216] 3)v is an integer from 0 to 2.

[0217] The compound represented by Formula 3 is represented by any one of Formula 3-7 to Formula 3-9.

[0218]

[0219]

[0220] Among them, each symbol can be defined as follows.

[0221] 1) Y, ring B, R 9 , L 6 ,Ar 4 and o as defined above,

[0222] 2) R 17 Selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C6-C 60 Aryloxy groups;

[0223] Among them, 17 In the case of an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 25 The aryl group, for example, may be phenylene, biphenylene, naphthalene, terphenylene, etc.

[0224] Among them, 17 In the case of a heterocyclic group, it is preferably C2-C 30 A heterocyclic group, and more preferably a C2-C24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, etc.

[0225] Among them, 17 In the case of a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 A fused aromatic ring group, and more preferably a C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0226] Among them, 17 In the case of an alkyl group, it is preferably C1-C 30 An alkyl group, and more preferably a C1-C 24 Alkyl groups,

[0227] Among them, 17 In the case of an alkenyl group, it is preferably C2-C 30 Alkenyl groups, and more preferably C2-C 24 Alkenyl groups,

[0228] Among them, 17 In the case of an alkynyl group, it is preferably C2-C 30 Alkynyl group, and more preferably C2-C 24 Alkynyl group,

[0229] Among them, 17 In the case of an alkoxy group, it is preferably C1-C 30 Alkoxy groups, and more preferably C1-C 24 Alkoxy groups,

[0230] Among them, 17 In the case of an aryloxy group, it is preferably C2-C 30 aryloxy group, and more preferably C2-C 24 Aryloxy groups,

[0231] 3)w is an integer from 0 to 6.

[0232] In addition, the compound represented by Formula 3 is represented by any one of the following Formulas 3-10 to 3-12.

[0233]

[0234] in,

[0235] 1) Y, ring B, R 8 , L 6 ,Ar 4 and n is as defined above,

[0236] 2) R 18 With R 17 The definition is the same as

[0237] 3)x is an integer from 0 to 6.

[0238] In addition, the compound represented by Formula 3 is represented by any one of the following Formulas 3-13 to 3-18.

[0239]

[0240] in,

[0241] 1) Y, L 6 ,Ar 4 , R 8 , R 9 , R 17 , R 18 , n and o are as defined above,

[0242] 2) R 16 With R 8 The definition is the same as

[0243] 3) v is an integer from 0 to 2, w and x are each independently an integer from 0 to 6,

[0244] The compound represented by Formula 3 is represented by Formula 19.

[0245]

[0246] in

[0247] 1) L 6 ,Ar 4 , R a , R 9 , R 17 and o as defined above,

[0248] 2) R 16 With R 8 The definition is the same as

[0249] 3) v is an integer from 0 to 2, w is an integer from 0 to 6,

[0250] Specifically, the compound represented by Formula 1 may be any one of the following Compound P-1 to Compound P-100.

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] Specifically, the compound represented by Formula 2 may be any one of the following Compound N-1 to Compound N-96.

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264] Specifically, the compound represented by Formula 3 may be any one of the following Compounds S-1 to S-108.

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] The present invention may further include a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

[0272] In addition, the organic material layer may include 2 or more stacked bodies including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the 2 or more stacked bodies.

[0273] In another aspect, the present invention also provides an electronic device comprising a display device including an organic electronic element; and a control unit for driving the display device; here, 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.

[0274] Hereinafter, a synthesis example of the compound represented by the formula and an example of manufacturing an organic electronic element according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[0275] [Synthesis example 1]

[0276] The compound represented by Formula 1 according to the present invention (final product) may be synthesized by reacting Sub 1 with Sub 2 as shown in Reaction Scheme 1, but is not limited thereto.

[0277] <Reaction Scheme 1>

[0278]

[0279] I. Compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub 1.

[0280]

[0281]

[0282] [Table 1]

[0283]

[0284]

[0285] II. Synthesis of Sub 2

[0286] Sub 2 of Reaction Scheme 1 can be synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0287] <Reaction Scheme 2>

[0288]

[0289] 1. Synthesis example of Sub 2-1

[0290]

[0291] After Sus2b-1 (13.9 g, 61.5 mmol) was dissolved in THF (tetrahydrofuran) (310 mL) in a round-bottom flask, Sub2a-1 (25.0 g, 61.5 mmol), NaOH (7.4 g, 184.6 mmol), Pd(PPh3)4 (4.27 g, 3.69 mmol) and water (155 mL) were added and stirred at 80°C. When the reaction was completed, the reactant was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized by using a silica gel column to obtain 21.5 g of the product (yield 74.5%).

[0292] 2. Synthesis example of Sub 2-2

[0293]

[0294] (1) Synthesis example of Sub2a-2

[0295] After dissolving Sub2d-2 (22.9 g, 69.4 mmol) in THF (350 mL) in a round-bottom flask, Sub2c-2 (20.0 g, 69.4 mmol), NaOH (8.3 g, 208.2 mmol), Pd(PPh3)4 (4.81 g, 4.16 mmol), and water (175 mL) were added, and 20.4 g of the product was obtained using the above synthesis method of Sub2-1 (yield 71.4%).

[0296] (2) Synthesis example of Sub2-2

[0297] After dissolving Sub2b-1 (11.2 g, 49.5 mmol) in THF (250 mL) in a round-bottom flask, Sub2a-2 (20.4 g, 49.5 mmol), NaOH (5.9 g, 148.6 mmol), Pd(PPh3)4 (3.44 g, 2.97 mmol), and water (125 mL) were added, and 16.9 g of the product was obtained using the above synthesis method of Sub2-1 (yield 71.7%).

[0298] 3. Synthesis example of Sub 2-9

[0299]

[0300] After dissolving Sub2b-9 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh3)4 (2.56 g, 2.21 mmol), and water (92 mL) were added, and 16.1 g of the product was obtained using the above synthesis method of Sub2-1 (yield 73.3%).

[0301] 4. Synthesis example of Sub 2-13

[0302]

[0303] After dissolving Sub2b-13 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh3)4 (2.56 g, 2.21 mmol), and water (92 mL) were added, and 16.0 g of the product was obtained using the above synthesis method of Sub2-1 (yield 72.7%).

[0304] 5. Synthesis example of Sub 2-20

[0305]

[0306] After dissolving Sub2b-1 (17.1 g, 75.7 mmol) in THF (380 mL) in a round-bottom flask, Sub2a-20 (25.0 g, 75.7 mmol), NaOH (9.1 g, 227.1 mmol), Pd(PPh3)4 (5.25 g, 4.54 mmol), and water (190 mL) were added, and 21.5 g of the product was obtained using the above synthesis method of Sub2-1 (yield 72.1%).

[0307] 6. Synthesis example of Sub 2-36

[0308]

[0309] (1) Synthesis example of Sub2b-36

[0310] After dissolving Sub2c-1 (8.4 g, 45.4 mmol) in THF (230 mL) in a round-bottom flask, Sub2a-20 (15.0 g, 45.4 mmol), NaOH (5.5 g, 136.3 mmol), Pd(PPh3)4 (3.15 g, 2.73 mmol), and water (115 mL) were added, and 10.2 g of the product was obtained using the above synthesis method of Sub2-1 (yield 63.7%).

[0311] (2) Synthesis example of Sub2-36

[0312] After dissolving Sub2b-36 (10.2 g, 28.9 mmol) in THF (145 mL) in a round-bottom flask, Sub2a-20 (9.6 g, 28.9 mmol), NaOH (3.5 g, 86.8 mmol), Pd(PPh3)4 (2.01 g, 1.74 mmol), and water (72 mL) were added, and 10.7 g of the product was obtained using the above synthesis method of Sub2-1 (yield 71.0%).

[0313] 7. Synthesis example of Sub 2-39

[0314]

[0315] After dissolving Sub2b-39 (16.0 g, 45.4 mmol) in THF (230 mL) in a round-bottom flask, Sub2a-20 (15.0 g, 45.4 mmol), NaOH (5.5 g, 136.3 mmol), Pd(PPh3)4 (3.15 g, 2.73 mmol), water (115 mL) were added, and 17.1 g of the product was obtained using the above synthesis method of Sub2-1 (yield 72.6%).

[0316] 8. Synthesis example of Sub 2-50

[0317]

[0318] (1) Synthesis example of Sub2a-50

[0319] After dissolving Sub2e-50 (10.7 g, 65.8 mmol) in THF (330 mL) in a round-bottom flask, Sub2c-50 (25.0 g, 65.8 mmol), NaOH (7.9 g, 197.3 mmol), Pd(PPh3)4 (4.56 g, 3.95 mmol), and water (165 mL) were added, and 17.9 g of the product was obtained using the above synthesis method of Sub2-1 (yield 81.1%).

[0320] (2) Synthesis example of Sub2-50

[0321] After dissolving Sub2b-1 (12.1 g, 53.3 mmol) in THF (270 mL) in a round-bottom flask, Sub2a-50 (17.9 g, 53.3 mmol), NaOH (6.4 g, 160.0 mmol), Pd(PPh3)4 (3.70 g, 3.20 mmol), and water (135 mL) were added, and 15.8 g of the product was obtained using the above synthesis method of Sub2-1 (yield 74.4%).

[0322] 9. Synthesis example of Sub 2-54

[0323]

[0324] After dissolving Sub2b-54 (9.3 g, 30.3 mmol) in THF (151 mL) in a round-bottom flask, Sub2a-20 (10.0 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), Pd(PPh3)4 (2.10 g, 1.82 mmol), and water (76 mL) were added, and 11.0 g of the product was obtained using the above synthesis method of Sub2-1 (yield 72.7%).

[0325] 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 compounds belonging to Sub 2.

[0326]

[0327]

[0328]

[0329]

[0330] [Table 2]

[0331]

[0332]

[0333] III. Synthesis of the final product

[0334] 1. Synthesis Example of P-1

[0335]

[0336] After Sus2b-1 (5.0 g, 10.7 mmol) was dissolved in THF (tetrahydrofuran) (54 mL) in a round-bottom flask, Sub1-1 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol), water (27 mL) were added and stirred at 80°C. When the reaction was completed, the reactant was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized by using a silica gel column to obtain 4.8 g of the product (yield 77%).

[0337] 2. Synthesis Example of P-8

[0338]

[0339] After dissolving Sub2-1 (4.9 g, 10.5 mmol) in THF (53 mL) in a round-bottom flask, Sub1-3 (3.0 g, 10.5 mmol), NaOH (1.3 g, 31.6 mmol), Pd(PPh3)4 (0.73 g, 0.63 mmol), and water (26 mL) were added, and 4.6 g of the product was obtained using the above synthesis method of P-1 (yield 74%).

[0340] 3. Synthesis Example of P-9

[0341]

[0342] After dissolving Sub2-1 (5.0 g, 10.7 mmol) in THF (54 mL) in a round-bottom flask, Sub1-4 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol), and water (27 mL) were added, and 4.5 g of the product was obtained using the above synthesis method of P-1 (yield 71%).

[0343] 4. Synthesis Example of P-16

[0344]

[0345] After dissolving Sub2-10 (5.4 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-5 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 5.0 g of the product was obtained using the above synthesis method of P-1 (yield 72%).

[0346] 5. Synthesis Example of P-19

[0347]

[0348] After dissolving Sub2-1 (4.3 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-7 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 4.3 g of the product was obtained using the above synthesis method of P-1 (yield 75%).

[0349] 6. Synthesis Example of P-22

[0350]

[0351] After dissolving Sub2-1 (4.2 g, 8.9 mmol) in THF (45 mL) in a round-bottom flask, Sub1-9 (3.0 g, 8.9 mmol), NaOH (1.1 g, 26.8 mmol), Pd(PPh3)4 (0.62 g, 0.54 mmol), and water (22 mL) were added, and 4.2 g of the product was obtained using the above synthesis method of P-1 (yield 73%).

[0352] 7. Synthesis Example of P-25

[0353]

[0354] After dissolving Sub2-1 (4.3 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-10 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 4.5 g of the product was obtained using the above synthesis method of P-1 (yield 77%).

[0355] 8. Synthesis Example of P-30

[0356]

[0357] After dissolving Sub2-1 (4.0 g, 8.4 mmol) in THF (42 mL) in a round-bottom flask, Sub1-12 (3.0 g, 8.4 mmol), NaOH (1.0 g, 25.3 mmol), Pd(PPh3)4 (0.58 g, 0.51 mmol), and water (21 mL) were added, and 4.1 g of the product was obtained using the above synthesis method of P-1 (yield 74%).

[0358] 9. Synthesis Example of P-34

[0359]

[0360] After dissolving Sub2-2 (4.3 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-15 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 4.6 g of the product was obtained using the above synthesis method of P-1 (yield 78%).

[0361] 10. Synthesis Example of P-40

[0362]

[0363] After dissolving Sub2-6 (5.0 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-16 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 5.0 g of the product was obtained using the above synthesis method of P-1 (yield 77%).

[0364] 11. Synthesis Example of P-42

[0365]

[0366] After dissolving Sub2-6 (5.0 g, 9.1 mmol) in THF (45 mL) in a round-bottom flask, Sub1-17 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh3)4 (0.63 g, 0.55 mmol), and water (23 mL) were added, and 4.5 g of the product was obtained using the above synthesis method of P-1 (yield 70%).

[0367] 12. Synthesis Example of P-45

[0368]

[0369] After dissolving Sub2-20 (2.9 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-19 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 4.0 g of the product was obtained using the above synthesis method of P-1 (yield 76%).

[0370] 13. Synthesis Example of P-53

[0371]

[0372] After dissolving Sub2-54 (3.5 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-19 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 4.0 g of the product was obtained using the above synthesis method of P-1 (yield 76%).

[0373] 14. Synthesis Example of P-56

[0374]

[0375] After dissolving Sub2-39 (3.8 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-19 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 4.4 g of the product was obtained using the above synthesis method of P-1 (yield 78%).

[0376] 15. Synthesis Example of P-65

[0377]

[0378] After dissolving Sub2-20 (2.9 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-22 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 3.8 g of the product was obtained using the above synthesis method of P-1 (yield 80%).

[0379] 16. Synthesis Example of P-77

[0380]

[0381] After dissolving Sub2-36 (3.8 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-22 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 4.3 g of the product was obtained using the above synthesis method of P-1 (yield 77%).

[0382] 17. Synthesis Example of P-80

[0383]

[0384] After dissolving Sub2-50 (2.9 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-22 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 3.7 g of the product was obtained using the above synthesis method of P-1 (yield 78%).

[0385] 18. Synthesis Example of P-85

[0386]

[0387] After dissolving Sub2-20 (2.9 g, 7.4 mmol) in THF (37 mL) in a round-bottom flask, Sub1-24 (3.0 g, 7.4 mmol), NaOH (0.9 g, 22.1 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), and water (18 mL) were added, and 3.0 g of the product was obtained using the above synthesis method of P-1 (yield 63%).

[0388] Meanwhile, FD-MS values ​​of Compound P-1 to Compound P-100 of the present invention prepared according to Synthesis Examples are shown in Table 3.

[0389] [Table 3]

[0390]

[0391]

[0392] [Synthesis example 2]

[0393] 1. Synthesis Example of N-12

[0394]

[0395] N-12a (30 g, 0.08 mol), N-12b (34.8 g, 0.08 mol), Pd2(dba)3 (2.3 g, 0.003 mol), NaOt-Bu (24.5 g, 0.25 mol), P(t-Bu)3 (2.1 g, 0.005 mol), toluene (170 mL) were added and reacted at 135° C. for 6 hours. When the reaction was completed, 53 g (85.8%) of the product N-12 was obtained using the isolation method of P-1 described above.

[0396] 2. Synthesis Example of N-19

[0397]

[0398] N-19a (50 g, 0.13 mol), N-19b (35 g, 0.13 mol), Pd2(dba)3 (3.6 g, 0.004 mol), NaOt-Bu (37.6 g, 0.40 mol), P(t-Bu)3 (3.2 g, 0.008 mol), toluene (260 mL) were added and reacted at 135° C. for 6 hours. When the reaction was completed, 67 g (83.4%) of the product N-19 was obtained using the isolation method of P-1 described above.

[0399] 3. Synthesis example of S-32

[0400]

[0401] S-32a (10 g, 0.04 mol), S-32b (15.6 g, 0.04 mol), Pd2(dba)3 (1.1 g, 0.001 mol), NaOt-Bu (11.7 g, 0.12 mol), P(t-Bu)3 (1.0 g, 0.002 mol), toluene (80 mL) were added and reacted at 135° C. for 6 hours. When the reaction was completed, 18 g (80.8%) of the product S-32 was obtained using the isolation method of P-1 described above.

[0402] 4. Synthesis Example of S-74

[0403]

[0404] S-74a (15 g, 0.06 mol), S-74b (20.9 g, 0.06 mol), Pd2(dba)3 (1.6 g, 0.002 mol), NaOt-Bu (16.9 g, 0.18 mol), P(t-Bu)3 (1.4 g, 0.004 mol), toluene (120 mL) were added and reacted at 135° C. for 6 hours. When the reaction was completed, 27 g (86.4%) of the product S-74 was obtained using the isolation method of P-1 described above.

[0405] 5. Synthesis Example of S-104

[0406]

[0407] S-104a (30 g, 0.13 mol), S-104b (48.2.9 g, 0.13 mol), Pd2(dba)3 (3.5 g, 0.004 mol), NaOt-Bu (36.4 g, 0.38 mol), P(t-Bu)3 (3.1 g, 0.008 mol), toluene (250 mL) were added and reacted at 135° C. for 6 hours. When the reaction was completed, 60 g (81.5%) of the product S-104 was obtained using the isolation method of P-1 described above.

[0408] Meanwhile, FD-MS values ​​of Compound N-1 to Compound N-96 and Compound S-1 to Compound S-108 of the present invention prepared according to Synthesis Examples are shown in Tables 4 and 5.

[0409] [Table 4]

[0410]

[0411]

[0412]

[0413] [Table 5]

[0414]

[0415]

[0416]

[0417] In addition, the synthesis examples of the present invention represented by Formula 1 to Formula 3 have been described, but these are all based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and those skilled in the art should easily understand that the reaction can be carried out even when other substituents defined in Formula 1 to Formula 3 other than the substituents specified in the specific synthesis example are bonded.

[0418] Organic Electronics Component Manufacturing Evaluation

[0419] [Example 1] Red organic light-emitting device (phosphorescent host)

[0420] An organic electroluminescent device is manufactured according to a conventional method using the compound obtained by synthesis as a light-emitting host material for a light-emitting layer.

[0421] First, a 60 nm thick hole injection layer is formed by vacuum depositing a N1-(naphthalene-2-yl)-N4,N4-bis(4-(naphthalene-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) film on an ITO layer (anode) formed on a glass substrate. A hole transport layer is formed by vacuum depositing 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound on the hole injection layer to a thickness of 50 nm. As a material for the light-emitting auxiliary layer, tris(4-(9H-carbazole-9-yl)phenyl)amine (hereinafter, TCTA) is vacuum deposited to a thickness of 10 nm on top of the hole transport layer to form a light-emitting auxiliary layer. After forming the light-emitting auxiliary layer, the compound of the present invention P-1 represented by Formula 1 and the compound of the present invention N-14 represented by Formula 2 are used as the main body on the top of the light-emitting auxiliary layer in a weight ratio of (5:5), and the light-emitting layer is deposited to a thickness of 30nm by doping (piq)2Ir(acac) with a weight ratio of 95:5 as a dopant material. Next, (1,1'-biphenyl)-4-root)bis(2-methyl-8-quinolinyl)aluminum (hereinafter, BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and bis(10-hydroxybenzo[h]quinoline)beryllium (hereinafter, BeBq2) is formed into a 25nm thick film as an electron transport layer. Afterwards, the alkali metal halide LiF is deposited to a thickness of 0.2nm as an electron injection layer, and then Al is deposited to a thickness of 150nm and used as a cathode to manufacture an organic electroluminescent device.

[0422] [Example 2] to [Example 156]

[0423] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention shown in Table 6 were used as host materials of the light-emitting layer instead of Compound P-1 and Compound N-14 of the present invention.

[0424] [Comparative Example 1] to [Comparative Example 10]

[0425] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 6 were used as host materials of the light-emitting layer instead of Compound P-1 and Compound N-14 of the present invention.

[0426]

[0427]

[0428] For the organic electroluminescent devices manufactured by Examples 1 to 156, Comparative Examples 1 and 10, electroluminescent (EL) characteristics were measured by applying a forward bias DC voltage using PR-650 manufactured by PhotoResearch Co. As a result of the measurement, the lifetime measurement device manufactured by McScience measured the EL characteristics at 2500 cd / m 2 Table 6 shows the results of device fabrication and evaluation.

[0429] The measuring device is not affected by possible daily fluctuations in deposition rate, vacuum quality or other parameters and makes it possible to evaluate the performance of the new material in comparison with the comparative compound under the same conditions. In the evaluation, since one batch contained four identically prepared OLEDs containing the comparative compound and since the performance of a total of 12 OLEDs was evaluated in three batches, the values ​​of the experimental results obtained in this way showed statistical significance.

[0430] [Table 6]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438] As can be seen from Table 6, when the compound of the present invention is used as the host material of the light-emitting layer, it can be seen that the device performance is greatly improved compared with Comparative Examples 1 to 10. In the case of Comparative Examples 5 to 10 using Comparative Compound A, Comparative Compound D, or Comparative Compound E as the first compound and using Compound N-75 or Compound S-104 as the second compound, improvements in efficiency and service life can be seen compared with Comparative Examples 1 to 4 using Comparative Compounds B to E as the first compound and using Comparative Compound F as the second compound.

[0439] In addition, compared with Comparative Examples 5 to 10, it can be seen that Examples 1 to 156 using the compound of the present invention represented by Formula 1 as the first compound exhibit significantly superior performance in terms of efficiency and service life, and thus it can be seen that the performance of the device varies depending on the composition of the compound. Therefore, it can be confirmed that the compound of the present invention represented by Formula 1 has better device performance than other comparative compounds not described in this specification.

[0440] That is, when the compound of the present invention represented by Formula 1 is compared with Comparative Compound A or Comparative Compound E, the type of substituent bonded to triazine is different, and the mobility varies depending on the type of substituent. That is, driving, efficiency and service life are determined by the ease of hole and electron injection into dopants. It can be judged that when the ratio (charge balance) of holes and electrons is properly maintained, efficiency and service life are significantly increased. This is expected to affect charge balance according to the degree of mobility of the first compound and the second compound.

[0441] Therefore, it is considered that the synergistic effect of the compound of the present invention represented by Formula 2 or Formula 3 and the compound of the present invention represented by Formula 1 leads to high efficiency and long service life.

[0442] In other words, in terms of overall characteristics, the compound of the present invention represented by Formula 1 has high electronic stability, and therefore shows high electronic stability and long service life compared with the comparative compound. Comparing the compounds of the present invention, it can be seen that the device performance is determined according to the components of the compound. In terms of driving voltage, it is highly dependent on the total EOD and HOD, and it can be seen that the mobility is determined by the type of substituents possessed by the compound, and the efficiency is determined by the balance of electrons and holes of the heterogeneous compound. Therefore, depending on the type and bonding position of the substituents substituted in the same skeleton, the performance of the device is greatly affected.

[0443] 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.

[0444] [Industrial Applicability]

[0445] According to the present invention, an organic device having excellent device characteristics such as high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. An organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound represented by Formula 1; and a compound represented by Formula 2 or Formula 3; in: 1) L 1 is a substituent represented by any one of the following formulas L-1 to L-4, 2) L 2 is a single bond; or C6-C 60 arylene groups; 3) L 3 , L 4 , L 5 and L 6 are each independently selected from a single bond; or C6-C 60 Arylene group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups; 4) Ar is C6-C 60 Aryl groups, 5)Ar 1 ,Ar 2 and Ar 3 Each independently selected from C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups; 6) Ar 4 Each independently selected from C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group; and -L'-NR b R c ; 7) L' is each independently selected from a single bond; and C6-C 60 Arylene group; C2-C 60 Heterocyclic groups; 8) R b and R c Each independently selected from C6-C 60 Aryl group; C3-C 60 Aliphatic ring and C6-C 60 A fused aromatic ring group; a C2-C 60 Heterocyclic group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 Aryloxy groups; 9) Ring A is a substituent represented by the following formula a; or formula b; 10) Ring B is C6-C 20 Aryl groups; 11) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are independently hydrogen; or deuterium; 12) R 8 and R 9 are the same or different and are independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; and C6-C 60 Aryloxy group; or multiple adjacent R 8 or multiple R 9 can be bonded to each other to form a ring, 13) a and d are each independently an integer from 0 to 5, b and f are each independently an integer from 0 to 6, c, e, g, h, n and o are each independently an integer from 0 to 4, and i is an integer from 0 to 7, 14) z is 0 or 1, provided that when z is 0, Formula 1 is represented by Formula 1-2: <Formula 1-2> 15)Y is O, S, CR'R" or NR a , 16) wherein R' and R" are each independently selected from hydrogen; deuterium; C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 aryloxy group; alternatively, R' and R" may be bonded to each other to form a spiro ring, 17) R a It is C6-C 60 or a C2-C ... 60 Heterocyclic groups; 18)* indicates the position to be bonded, 19) wherein the aryl group, arylene group, heterocyclic group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more than one substituent selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; 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, wherein the term "ring" means C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by combining them.

2. The organic electronic device according to claim 1, wherein Formula 1 is represented by Formula 1-1: <Formula 1-1> Where R 1 , R 2 , R 3 , L 1 , L 2 , Ar, Ring A, a, b and c are as defined in claim 1.

3. The organic electronic device according to claim 1, wherein Formula 1 is represented by Formula 1-1-a or Formula 1-1-b: Where R 1 , R 2 , R 3 , R 7 , L 1 , L 2 , Ar, a, b, c and i are as defined in claim 1.

4. The organic electronic device according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1-1 to 1-1-5: Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, c, d, e, f, g, h and i are as defined in claim 1.

5. The organic electronic device according to claim 1, wherein Formula 1 is represented by Formula 1-2-a: <Formula 1-2-a> Where R 1 , R 2 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, g, h and i are as defined in claim 1.

6. The organic electronic device according to claim 1, wherein Formula 1 is represented by any one of Formula 1-2-b to Formula 1-2-d: Where R 1 , R 2 , R 5 , R 6 , R 7 , L 2 , Ar, a, b, g, h and i are as defined in claim 1.

7. The organic electronic device according to claim 1, wherein Formula 2 is represented by Formula 2-1: <Formula 2-1> in: 1) L 3 , L 4 , L 5 ,Ar 2 and Ar 3 As defined in claim 1, 2)X 1 Same as the definition of Y in claim 1, 3) R 10 and R 11 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 4) p is an integer from 0 to 4, 5)q is an integer from 0 to 3.

8. The organic electronic device according to claim 1, wherein Formula 2 is represented by Formula 2-2: <Formula 2-2> in: 1) L 3 , L 4 , L 5 and Ar 3 As defined in claim 1, 2)X 1 and X 2 Same as the definition of Y in claim 1, 3) R 10 , R 11 , R 12 and R 13 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 4) p and r are each independently an integer from 0 to 4, 5) q and s are each independently an integer from 0 to 3.

9. The organic electronic device according to claim 1, wherein Formula 2 is represented by Formula 2-3: <Formula 2-3> in: 1) L 3 , L 4 and L 5 As defined in claim 1, 2)X 1 , X 2 and X 3 Same as the definition of Y in claim 1, 3) R 10 , R 11 , R 12 , R 13 , R 14 and R 15 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 4) p, r and t are each independently an integer from 0 to 4, 5) q, s and u are each independently an integer from 0 to 3.

10. The organic electronic device according to claim 1, wherein Formula 3 is represented by any one of Formula 3-1 to Formula 3-6: in: 1) Y, R 8 , R 9 , L 6 ,Ar 4 , n and o as defined in claim 1, 2) R 16 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 3)v is an integer from 0 to 2.

11. The organic electronic device according to claim 1, wherein Formula 3 is represented by any one of Formulas 3-7 to 3-9: in: 1) Y, ring B, R 9 , L 6 ,Ar 4 and o as defined in claim 1, 2) R 17 is selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; and C6-C 60 Aryloxy groups; 3)w is an integer from 0 to 6.

12. The organic electronic device according to claim 1, wherein Formula 3 is represented by any one of the following Formulas 3-10 to 3-12: in: 1) Y, ring B, R 8 , L 6 ,Ar 4 and n as defined in claim 1, 2) R 18 R in claim 11 17 The definition is the same as 3)x is an integer from 0 to 6.

13. The organic electronic device according to claim 1, wherein Formula 3 is represented by any one of the following Formulas 3-13 to 3-18: in: 1) Y, L 6 ,Ar 4 , R 8 , R 9 , n and o as defined in claim 1, 2) R 16 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 2) R 17 and R 18 are the same or different and are independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; and C6-C 60 Aryloxy groups; 4) v is an integer from 0 to 2, and w and x are each independently an integer from 0 to 6.

14. The organic electronic device according to claim 1, wherein Formula 3 is represented by Formula 19: <Formula 19> in: 1) L 6 ,Ar 4 , R a , R 9 and o as defined in claim 1, 2) R 16 Selected from deuterium; halogen; cyano group; nitro group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; C2-C 20 Heterocyclic group; and C3-C 20 Cycloalkyl groups, 3) R 17 As defined in claim 11, 4) v is an integer from 0 to 2, and w is an integer from 0 to 6.

15. The organic electronic device according to claim 1, wherein the compound represented by Formula 1 may be any one of the following compounds P-1 to P-100:

16. The organic electronic element according to claim 1, wherein the compound represented by Formula 2 may be any one of the following compounds N-1 to N-96:

17. The organic electronic device according to claim 1, wherein the compound represented by Formula 3 may be any one of the following compounds S-1 to S-108: 18 . The organic electronic element of claim 1 , wherein the organic electronic element further comprises a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 19 . The organic electronic element according to claim 1 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 20 . The organic electronic element of claim 19 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies.

21. An electronic device comprising a display device including the organic electronic element according to claim 1; and a control unit for driving the display device.

22. The electronic device of claim 21, wherein the organic electronic element is at least one of an OLED, an organic transistor, and an element for monochrome or white lighting.

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