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

Abstract

The present invention provides a compound represented by chemical formula 1, an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric element. The organic material layer includes a compound represented by chemical formula 1, so that the driving voltage of the organic electric element can be reduced, and the luminous efficiency and lifetime can be improved.

Description

Technical Field

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

[0002] Generally, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electrical components using organic light emitting phenomenon generally have a structure including an anode, a cathode and an organic layer therebetween. Here, the organic layer is generally formed into a multilayer structure composed of various substances in order to improve the efficiency and stability of the organic electrical component. For example, it can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

[0003] The most serious problems in organic light-emitting devices are life and efficiency. As displays become larger, such efficiency and life problems have become issues that must be solved.

[0004] Efficiency, lifespan, and driving voltage are interrelated. If efficiency increases, driving voltage decreases relatively. Crystallization of organic substances due to Joule heating that occurs when driving at a lower driving voltage decreases, and ultimately the lifespan tends to increase.

[0005] However, simply improving the above-mentioned organic layer cannot maximize the efficiency. This is because only when the energy level and T1 value between the organic layers and the inherent properties of the material (mobility, surface properties, etc.) form an optimal combination can long life and high efficiency be achieved at the same time.

[0006] Therefore, in order to fully demonstrate the excellent characteristics of organic electrical devices, it is necessary to develop materials for the organic layers constituting the devices, especially the light-emitting auxiliary layer. Summary of the invention

[0007] Technical issues

[0008] An object of the present invention is to provide a compound capable of reducing the driving voltage of a device and improving the luminous efficiency and life, and an organic electric device and an electronic device using the compound.

[0009] Technical Solution

[0010] In one aspect, the present invention provides a compound represented by the following chemical formula.

[0011]

[0012] In another aspect, the present invention provides an organic electric element and an electronic device thereof using the compound represented by the above chemical formula.

[0013] Effects of the Invention

[0014] By using the compounds of the embodiments of the present invention, not only the driving voltage of the element can be reduced, but also the luminous efficiency and life of the element can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0016] Description of Reference Numerals

[0017] 100, 200, 300: organic electrical element 110: first electrode

[0018] 120: hole injection layer 130: hole transport layer

[0019] 140: Light-emitting layer 150: Electron transport layer

[0020] 160: electron injection layer 170: second electrode

[0021] 180: Light efficiency improvement layer 210: Buffer layer

[0022] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0023] 330: first hole transport layer 340: first light emitting layer

[0024] 350: first electron transport layer 360: first charge generation layer

[0025] 361: second charge generation layer 420: second hole injection layer

[0026] 430: second hole transport layer 440: second light emitting layer

[0027] 450: Second electron transport layer CGL: Charge generation layer

[0028] ST1: First stack ST2: Second stack DETAILED DESCRIPTION

[0029] The terms "aryl" and "arylene" used in the present invention have carbon numbers of 6 to 60, unless otherwise specified, but are not limited thereto. In the present invention, aryl or arylene includes monocyclic types, ring aggregates, fused polycyclic types, and spiro compounds.

[0030] The term "fluorenyl" used in the present invention means a substituted or unsubstituted fluorenyl, and "fluorenylene" means a substituted or unsubstituted fluorenylene. The fluorenyl or fluorenylene used in the present invention include spiro compounds formed by mutual bonding between R and R' in the following structure, and also include cyclic compounds formed by mutual bonding between adjacent R". "Substituted fluorenyl" and "substituted fluorenylene" mean that in the following structure at least one of the substituents R, R', R" is a substituent other than hydrogen, and R" in the following structure can have a valence of 1 to 8. Regardless of the valence, fluorenyl and fluorenylene can be named as fluorenylfluorene ring or fluorene in this specification.

[0031]

[0032] The term "spiro compound" used in the present invention means "spiro union", and spiro union means that two spiro atoms share only one atom to achieve connection. In this case, the atom shared by the two rings is called "spiro atom", and according to the number of spiro atoms contained in a compound, these are respectively called "monospiro", "bispiro" and "trispiro" compounds.

[0033] The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene", but also non-aromatic rings. Unless otherwise specified, it means a ring with 2 to 60 carbon atoms containing one or more heteroatoms, but the present invention is not limited to this. The term "heteroatom" used in the present invention, unless otherwise specified, is an element other than carbon, such as N, O, S, P or Si, and may also include compounds containing heteroatomic groups such as SO2, P=O, etc. in place of carbon forming the ring, as in the following compounds. Heterocyclic group means a monocyclic type, a ring aggregate, a fused polycyclic type, and a spirocyclic compound containing heteroatoms.

[0034]

[0035] The term "aliphatic cyclic group" used in the present invention means cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic types, ring aggregates, fused polycyclics, and spirocyclic compounds, etc. Unless otherwise specified, it means a ring with a carbon number of 3 to 60, but is not limited thereto. For example, a polycyclic ring formed by condensing an aromatic ring benzene and a non-aromatic ring cyclohexane also belongs to an aliphatic cyclic group.

[0036] In this specification, the "base name" corresponding to the aryl group, arylene group, heterocyclic group, etc. shown as examples of each symbol and its substituent may be recorded as the "base name reflecting the valence", but may also be recorded as the "parent compound name". For example, in the case of "phenanthrene" which is a kind of aryl group, the monovalent "base" is "phenanthryl", the divalent base is "phenanthrylene", etc., and the name of the base may be recorded by distinguishing the valence, but it may be recorded as "phenanthrene" as the name of the parent compound regardless of the valence. Similarly, in the case of pyrimidine, it may be recorded as "pyrimidine" regardless of the valence, or it may be recorded as the "base name" of the valence, for example, in the case of monovalent, it may be recorded as pyrimidinyl, in the case of divalent, it may be recorded as pyrimidinyl, etc.

[0037] In addition, when describing the names of compounds or substituents in the present invention, numerals or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofurano[2,3-d]pyrimidine may be described as benzofuranopyrimidine, 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene, etc. Therefore, benzo[g]quinoxaline or benzo[f]quinoxaline may be described as benzoquinoxaline.

[0038] Furthermore, unless otherwise specified, the chemical formulae used in the present specification can be applied in the same manner as the definitions of substituents defined by the indices in the following chemical formulae.

[0039]

[0040] When a is an integer of 0, the substituent R 1 In the case where a is not present, that is, a is 0, it means that the carbon atoms forming the benzene ring are all bonded with hydrogen atoms. In this case, the representation of the hydrogen atoms bonded to the carbon atoms can be omitted and the chemical formula or compound can be recorded. 1 It is bonded to one of the carbon atoms forming the benzene ring. When a is an integer of 2 or 3, it is bonded in the following manner. When a is an integer of 4 to 6, it is bonded to the carbon atoms of the benzene ring in a similar manner. When a is an integer of 2 or more, R 1 They may be the same as or different from each other.

[0041]

[0042] In addition, in this specification, unless otherwise specified, a ring means an aromatic ring, a heteroaromatic ring, a fluorene ring, an aliphatic ring, etc., a number-ring may mean a condensed ring, and a number-atom(s) ring may mean a single ring. For example, naphthalene is equivalent to a condensed ring of 2 rings, anthracene is equivalent to a condensed ring of 3 rings, thiophene, furan, etc. are equivalent to 5 atoms(s) rings, and benzene and pyridine are equivalent to 6 atoms(s) rings.

[0043] Furthermore, unless otherwise specified in the present specification, the ring formed by the bonding of adjacent groups is selected from C6 to C 60 Aromatic ring group; fluorenyl; C2-C 60 and C3~C 60 Here, the aromatic ring group may be an aromatic ring, and the heterocyclic group may include a heteroaromatic ring.

[0044] Unless otherwise specified in this specification, "adjacent groups" means, if the following chemical formula is used as an example, not only between R1 and R2, between R2 and R3, between R3 and R4, between R5 and R6, but also between R7 and R8 sharing a carbon, and may also include substituents bonded to non-directly adjacent ring-constituent elements (carbon or nitrogen, etc.) such as between R1 and R7, between R1 and R8, or between R4 and R5. That is, when there is a substituent in a ring-constituent element such as directly adjacent carbon or nitrogen, it can be an adjacent group, but when there is no substituent bonded to the ring-constituent element at the directly adjacent position, it can be an adjacent group with the substituent bonded to the next ring-constituent element, and the substituents bonded to the same ring-constituent carbon can also be called adjacent groups. In the following chemical formula, when substituents bonded to the same carbon such as R7 and R8 are bonded to each other to form a ring, a compound containing a spirocyclic portion can be formed.

[0045]

[0046] In the present specification, the expression 'adjacent groups may combine to form a ring' is used with the same meaning as 'adjacent groups combine to selectively form a ring' and means that at least one pair of adjacent groups combine to form a ring.

[0047] In addition, unless otherwise specified in the present specification, substituents such as aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkylthio, arylthio, and the like, and rings formed by adjacent groups bonding to each other, can be selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, C6~C 20 The arylthio group, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, and C1~C 20 Alkyl or C6~C 20 The aryl-substituted or unsubstituted phosphine oxide group may be further substituted with one or more substituents selected from the group consisting of the aryl-substituted or unsubstituted phosphine oxide group.

[0048] Below, refer to Figures 1 to 3 , the stacked structure of an organic electric device including the compound of the present invention is described.

[0049] In the process of adding reference numerals to the structural elements of each drawing, it is noted that the same structural elements are given the same reference numerals as much as possible even if they are shown in different drawings. In addition, in the process of describing the present invention, if it is judged that the detailed description of the relevant known structure or function will obscure the gist of the present invention, the detailed description will be omitted.

[0050] In the process of describing the structural elements of the present invention, the terms such as first, second, A, B, (a), (b) etc. may be used. Such terms are only used to distinguish from other structural elements, and the nature, order or sequence of the related structural elements will not be limited by such terms. When a structural element is "connected", "combined" or "coupled" to another structural element, the structural element can be directly connected or coupled to the other structural element, but it can also be understood that there are other structural elements "connected", "combined" or "coupled" between the structural elements.

[0051] Furthermore, when a structural element such as a layer, film, region, or plate is located "on" or "above" another structural element, this should be understood not only as being "directly above" the other structural element, but also as being other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood as being without other parts in between.

[0052] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0053] Reference Figure 1 An organic electrical element 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, an organic layer between the first electrode and the second electrode, and an inorganic layer between the first electrode and the second electrode, which are formed on a substrate (not shown).

[0054] For example, the first electrode 110 may be an anode, and the second electrode 170 may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode. The organic layer refers to a layer containing at least one organic substance. For example, the organic 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. However, the electron injection layer (160) may also be an inorganic layer that does not contain organic matter.

[0055] 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 .

[0056] Preferably, of the two surfaces of the first electrode 110 or the second electrode 170 , a light efficiency improvement layer 180 may be formed on the surface not in contact with the organic layer. When the light efficiency improvement layer 180 is formed, the light efficiency of the organic electrical element may be improved.

[0057] For example, a light efficiency improvement layer 180 may be formed on the second electrode 170. However, in the case of an organic light-emitting element with top emission, the light efficiency improvement layer 180 may reduce the loss of optical energy caused by SPPs (surface plasmon polarizations) in the second electrode 170. In the case of an organic light-emitting element with bottom emission, the light efficiency improvement layer 180 may perform a buffering effect on the second electrode 170.

[0058] 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. Figure 2 Provide explanation.

[0059] Reference Figure 2 According to another embodiment of the present invention, an organic electrical element 200 may include 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, which are sequentially formed on a first electrode 110, and a light efficiency improvement layer 180 may be formed on the second electrode.

[0060] Although not shown in Figure 2 An electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

[0061] In addition, according to another embodiment of the present invention, the organic layer may also be in the form of a stack of a plurality of hole transport layers, a light emitting layer, and an electron transport layer. Figure 3 Provide explanation.

[0062] Reference Figure 3 According to another embodiment of the present invention, the organic electrical element 300 may be formed with two or more stacks of organic layers (ST1, ST2) formed in multiple layers between the first electrode 110 and the second electrode 170, and a charge generation layer CGL is formed between the stacks of organic layers.

[0063] Specifically, the organic electrical device according to an embodiment of the present invention may include a first electrode 110 , a first stack ST1 , a charge generation layer CGL (Charge Generation Layer), a second stack ST2 , a second electrode 170 , and a light efficiency improvement layer 180 .

[0064] The first stack ST1, as an organic layer formed on the first electrode 110, 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. In this way, the first stack and the second stack may have organic layers with the same stacked structure, or may have organic layers with different stacked structures.

[0065] 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 current efficiency generated in each light emitting layer and smoothly distribute charges.

[0066] Although the first light-emitting layer 340 may include a light-emitting material containing a blue fluorescent dopant in a blue main body, and the second light-emitting layer 440 may include a material in which a green main body is doped with a greenish yellow dopant and a red dopant, the materials of the first light-emitting layer 340 and the second light-emitting layer 440 according to the embodiment of the present invention are not limited thereto.

[0067] exist Figure 3In the embodiment, n may be an integer of 1 to 5. However, when n is 2, a charge generation layer CGL and a third stack may be further stacked on the second stack ST2.

[0068] like Figure 3 By forming multiple light-emitting layers by means of a multi-layer stacking structure, it is possible to prepare not only an organic electrical light-emitting element that emits white light by means of a mixing effect of light emitted by each light-emitting layer, but also an organic electrical light-emitting element that emits light of multiple colors.

[0069] The compound represented by Chemical Formula 1 of the present invention may be included in an organic layer. For example, although the compound represented by Chemical Formula 1 of the present invention may be used as a material for the hole injection layer 120, 320, 420, the hole transport layer 130, 330, 430, the buffer layer 210, the luminescence auxiliary layer 220, the electron transport layer 150, 350, 450, the luminescence layer 140, 340, 440 or the light efficiency improvement layer 180, preferably, the material for the luminescence auxiliary layer 220 or / and the light efficiency improvement layer 180, more preferably, the material for the luminescence auxiliary layer 220.

[0070] Even for the same or similar cores, the band gap, electrical properties, surface properties, etc. may be different depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the core and the combination of the sub-substituents bonded to it. In particular, when the energy level and T1 value between each organic layer and the inherent properties of the material (mobility, surface properties, etc.) are optimally combined, long life and high efficiency can be achieved at the same time.

[0071] Therefore, the compound represented by Chemical Formula 1 in the present invention is used as the material of the light-emitting auxiliary layer 220, so that the energy level and T1 value between the organic layers, the inherent properties (mobility, surface properties, etc.), etc. can be optimized, while improving the life and efficiency of the organic electrical element.

[0072] The organic light-emitting element of one embodiment of the present invention can be prepared by various evaporation methods. It can be prepared by evaporation methods such as PVD or CVD. For example, the anode 110 can be formed by evaporating a metal or a conductive metal oxide or an alloy thereof on a substrate, and an organic layer including a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, an electron transport layer 150 and an electron injection layer 160 is formed thereon, and then a substance that can be used as a cathode 170 is evaporated thereon. In addition, a light-emitting auxiliary layer 220 can be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) can be formed between the light-emitting layer 140 and the electron transport layer 150. As described above, it can also be formed in a stacked structure.

[0073] Furthermore, the organic layer uses a variety of polymer materials and is formed into a smaller number of layers by a solvent treatment or solvent refining method other than the evaporation method, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process, or a thermal transfer method. Since the organic layer of the present invention can be formed by a variety of methods, the protection scope of the present invention is not limited by the formation method.

[0074] The organic electrical device according to an embodiment of the present invention can be classified into a front-emitting type, a rear-emitting type or a double-emitting type according to the materials used.

[0075] Furthermore, the organic electrical device according to an embodiment of the present invention is selected from the group consisting of an organic electrical light-emitting device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

[0076] Another embodiment of the present invention may include an electronic device, the electronic device including: a display device including the organic electrical element of the present invention; and a control unit for controlling the display device. In this case, the electronic device may be a current or future wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, navigation devices, game consoles, various TVs, and various computers.

[0077] Hereinafter, the compound according to one aspect of the present invention will be described.

[0078] A compound according to one aspect of the present invention is represented by Chemical Formula 1 below.

[0079] <Chemical Formula 1>

[0080]

[0081] In the above Chemical Formula 1, each symbol can be defined as follows.

[0082] A is the following chemical formula A-1 or chemical formula A-2.

[0083] <Chemical Formula A-1><Chemical Formula A-2>

[0084]

[0085] R 1 To R 9 independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ), and adjacent groups can be combined with each other to form a ring.

[0086] a is an integer of 0 to 5, b to d are integers of 0 to 4, e is an integer of 0 to 5, m is an integer of 0 to 2, f to i are integers of 0 to 3, and when they are integers of 2 or more, multiple R 1 Respectively, R 2 Respectively, R 3 Respectively, R 4 Respectively, R 5 Respectively, R 6 Respectively, R 7 Respectively, R 8 Respectively, R 9 The same or different respectively.

[0087] Between adjacent groups, for example, adjacent R 1 Between 2 Between 3 Between 4 Between 5 Between 6 Between 7 Between 8 Between 9 The ring formed by at least one pair of the two bonds can be selected from C6 to C 60 An aromatic ring group; a fluorene group; a C2-C 60 and C6~C 60 A group consisting of aliphatic ring groups.

[0088] When the ring formed by the combination of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 , C 12 , C 14 , C15 , C 16 , C 18 Specifically, it can form an aromatic ring group of benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0089] X 1 and X 2 are O or S independently of each other.

[0090] L 1 and L' are independently selected from single bonds; C6~C 60 Arylene; Fluorene; C3~C 60 and C2 to C2 containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 A group consisting of a heterocyclic group.

[0091] Ar 1 ,Ar 2 ,Ar 3 , R a and R b Independently selected from C6~C 60 Aryl; Fluorenyl; C3~C 60 and C2 to C2 containing at least one hetero atom selected from O, N, S, Si and P 60 A group consisting of a heterocyclic group. 2 and Ar 3 All can be C6~C 60 The aromatic group.

[0092] In the above R 1 To R 9 ,Ar 1 ,Ar 2 ,Ar 3 , R a and R b When at least one of the groups is an aryl group, the aryl group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23 、C6~C 22 、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 The aryl group includes phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene and the like.

[0093] In the above L 1 When at least one of L and L' is an arylene group, the arylene group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23 、C6~C 22 、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C 15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 phenyl, biphenylene, naphthylene, terphenyl, phenanthrene, triphenylene, etc. Preferably, L3 It may be phenyl, biphenyl or terphenyl.

[0094] In the above R 1 To R 9 ,Ar 1 ,Ar 2 ,Ar 3 , R a , R b , L 1 When at least one of L' and L' is a heterocyclic group, the heterocyclic group may be, for example, C2 to C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29and the like, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, thiorrole, indene, indole, phenyl-indole, benzindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, benz-carbazole, benzocarbazole, benz-benzocarbazole, naphthalene-benzocarbazole, dibenzo benzocarbazole, indolocarbazole, benzofuranopyridine, benzothienopyridine, benzofuranopyridine, benzothienopyrimidine, benzofuranopyrimidine, benzothienopyrazine, benzofuranopyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxine, benzodibenzodioxine, thianthrene, 9,9-dimethyl-9H-xanthene, 9,9-dimethyl-9H-thioxanthene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

[0095] In the above R 1 To R 9 ,Ar 1 ,Ar 2 ,Ar 3 , R a and R b At least one of them is fluorenyl or L 1 and when at least one of L' is a fluorenyl group, the fluorenyl group or fluorenyl group can be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0096] In the above R 1 To R 9 ,Ar 1 ,Ar 2 ,Ar 3 , R a and R b When at least one of the groups is an aliphatic ring group, the aliphatic ring group may be, for example, C3 to C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13, C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Aliphatic cyclic groups such as the above.

[0097] In the above R 1 To R 9 When at least one of the alkyl groups is an alkyl group, the alkyl group may be, for example, C1 to C 20 、C1~C 10 , C1-C4, C1, C2, C3, C4 and the like alkyl groups, for example, methyl, ethyl, tert-butyl and the like.

[0098] The above-mentioned aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and the ring formed by the adjacent groups are each selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C1~C 20 Alkylthio, and C6~C 30 The group consisting of arylthio and arylthio may be further substituted by one or more substituents selected from the group consisting of arylthio and arylthio.

[0099] When at least one of the above-mentioned aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups bonded to form a ring is further substituted with an aryl group, the above-mentioned aryl group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23、C6~C 22 、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C 15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 Etc. aromatic groups.

[0100] When at least one of the above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups bonded to form a ring is further substituted with a heterocyclic group, the above heterocyclic group may be, for example, C2 to C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 Heterocyclic groups such as those of

[0101] When at least one of the above-mentioned aryl groups, arylene groups, fluorenyl groups, fluorenylene groups, heterocyclic groups, aliphatic cyclic groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, and rings formed by mutual bonding of adjacent groups is further substituted by a fluorenyl group, the above-mentioned fluorenyl group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

[0102] When at least one of the above-mentioned aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups bonded to form a ring is further substituted with an aliphatic cyclic group, the above-mentioned aliphatic cyclic group may be, for example, C3 to C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12, C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Aliphatic cyclic groups such as the above.

[0103] When at least one of the above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups bonded to form a ring is further substituted with an alkyl group, the above alkyl group may be, for example, C1 to C 20 、C1~C 10 , C1~C4, C1, C2, C3, C4 and other alkyl groups.

[0104] The above Chemical Formula 1 may be represented by one of the following Chemical Formulas 2-1 to 2-6.

[0105]

[0106] In the above Chemical Formulae 2-1 to 2-6, R 1 To R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to d, and f to i are the same as defined in Chemical Formula 1.

[0107] In addition, the above Chemical Formula 1 may be represented by one of the following Chemical Formulas 3-1 to 3-8.

[0108]

[0109]

[0110] In the above Chemical Formulae 3-1 to 3-8, R 1 , R 2 , R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a, b, d, f to i are the same as defined in Chemical Formula 1.

[0111] R 3 is selected from deuterium; halogen; cyano; nitro; C6~C 60aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ) group.

[0112] In addition, the above Chemical Formula 1 may be represented by one of the following Chemical Formulas 4-1 to 4-8.

[0113]

[0114]

[0115] In the above Chemical Formulae 4-1 to 4-8, R 1 , R 2 , R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a, b, d, f to i are the same as defined in Chemical Formula 1.

[0116] R 3 is selected from deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ) group.

[0117] In addition, the above Chemical Formula 1 may be represented by the following Chemical Formula 5-1 or Chemical Formula 5-2.

[0118]

[0119] In the above Chemical Formula 5-1 and Chemical Formula 5-2, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as defined in Chemical Formula 1.

[0120] In addition, the above Chemical Formula 1 may be represented by one of the following Chemical Formulas 6-1 to 6-6.

[0121]

[0122]

[0123] In the above Chemical Formula 6-1 and Chemical Formula 6-6, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as defined in Chemical Formula 1.

[0124] In addition, the above Chemical Formula 1 may be represented by one of the following Chemical Formulas 7-1 to 7-4.

[0125]

[0126] In the above Chemical Formula 7-1 and Chemical Formula 7-4, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as defined in Chemical Formula 1.

[0127] In the above chemical formula, Ar 1 To Ar 3 At least one of the following chemical formulae Ar-1 to Ar-6 may be selected from the group consisting of.

[0128]

[0129]

[0130] In the above-mentioned chemical formula Ar-1 to chemical formula Ar-6, each symbol can be defined as follows.

[0131] R 11 To R16 independently selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, and C6~C 20 The adjacent groups can be combined with each other to form a ring.

[0132] m is an integer of 0 to 5, n, p, q, and r are integers of 0 to 4, and o is an integer of 0 to 3. When they are integers of 2 or more, R 13 Respectively, R 14 Respectively, R 15 Respectively, R 16 The same or different respectively.

[0133] The ring formed by the combination of adjacent groups can be selected from C6 to C 60 An aromatic ring group; a fluorene group; a C2-C 60 and C6~C 60 A group consisting of aliphatic ring groups.

[0134] When the ring formed by the combination of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 Specifically, it can form an aromatic ring group of benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0135] Y is S, O, C(R1)(R2) or N(R3).

[0136] R a is selected from a single bond; C1~C 20 Alkylene; C6~C 30 arylene; fluorene; C2~C 30 and C3~C 30 A group consisting of aliphatic ring groups.

[0137] R1 to R3, R b independently selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, and C6~C 20 The present invention relates to a group of arylthio groups, and R1 and R2 can be combined with each other to form a ring. When R1 and R2 are combined with each other to form a ring, a spiro compound can be formed, such as spirobifluorene.

[0138] Specifically, the compound represented by the above Chemical Formula 1 may be one of the following compounds, but is not limited thereto.

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] According to another aspect of the present invention, the present invention provides an organic electrical element including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes a compound represented by Chemical Formula 1.

[0155] The organic layer includes a light emitting layer between the first electrode and the second electrode, and a light emitting auxiliary layer between the light emitting layer and the first electrode, and the light emitting auxiliary layer may include the compound of Chemical Formula 1.

[0156] The organic layer includes two or more stacks, the stack includes a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode, and the organic layer also includes a charge generation layer formed between the two or more stacks.

[0157] The organic electrical element may further include a light efficiency improvement layer. In this case, the light efficiency improvement layer is formed on a surface of the first electrode or the second electrode that is not in contact with the organic layer.

[0158] According to another aspect of the present invention, the present invention provides an electronic device, which includes a display device and a control unit, wherein the control unit is used to drive the display device. In this case, the display device includes a compound represented by Chemical Formula 1.

[0159] Hereinafter, examples are given to specifically describe the synthesis examples of the compound represented by Chemical Formula 1 and the preparation examples of the organic electric device of the present invention, but the present invention is not limited to the following examples.

[0160] [Synthesis example]

[0161] The compound represented by Chemical Formula 1 according to the present invention (final product 1) may be prepared by reacting Sub1 with Sub2 as shown in the following Reaction Formula 1, but is not limited thereto.

[0162] <Reaction Formula 1> (Hal is Br, I or Cl)

[0163]

[0164] Sub2 is the following Sub2-A or Sub2-B.

[0165]

[0166] Synthesis example of Sub1

[0167] Sub1 of the above reaction formula 1 can be synthesized through the reaction pathway of the following reaction formula 2-1 or reaction formula 2-2, but is not limited thereto.

[0168] <Reaction Formula 2-1> (Hal, Hal 1 is Br, Cl or I. )

[0169]

[0170] <Reaction Formula 2-2>

[0171]

[0172] 1. Synthesis example of Sub1-3

[0173]

[0174] Suba1-3 (50 g, 115.80 mmol) and Subb1-3 (15.5 g, 127.38 mmol) were placed in a round-bottom flask and dissolved in 290 mL of THF and 100 mL of water, and then Pd(PPh3)4 (4.01 g, 3.47 mmol) and K2CO3 (32.00 g, 231.61 mmol) were added and reacted at 60°C. After the reaction was completed, the organic layer was extracted with toluene and water, dried over MgSO4, and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 43.8 g (yield: 88.2%) of the product.

[0175] 2. Synthesis example of Sub1-5

[0176]

[0177] Suba1-5 was used instead of Suba1-3, and the same method as the synthesis method of Sub1-3 was used to obtain 42.4 g of a product (yield: 85.4%).

[0178] 3. Synthesis example of Sub1-18

[0179]

[0180] Suba1-18 was used instead of Suba1-3, and Subb1-18 (21.9 g, 127.38 mmol) was used instead of Subb1-3. Synthesis was carried out in the same manner as the above-mentioned synthesis method of Sub1-3 to obtain 48.7 g of the product (yield: 87.8%).

[0181] 4. Synthesis example of Sub1-20

[0182]

[0183] Suba1-20 was used instead of Suba1-3, and Subb1-20 (21.9 g, 127.38 mmol) was used instead of Subb1-3. Synthesis was carried out in the same manner as the above-mentioned synthesis method of Sub1-3 to obtain 49.2 g of the product (yield: 88.7%).

[0184] 5. Synthesis example of Sub1-24

[0185]

[0186] Suba2-24 (50 g, 104.99 mmol) and Subb1-3 (14.1 g, 115.49 mmol) were placed in a round-bottom flask and dissolved in 270 mL of THF and 90 mL of water. Then Pd(PPh3)4 (3.63 g, 3.15 mmol) and K2CO3 (29.02 g, 209.99 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub1-3 to obtain 12.9 g of the product (yield: 25.9%).

[0187] 6. Synthesis example of Sub1-25

[0188]

[0189] Suba2-25 was used instead of Suba1-3, and the same method as the synthesis method of Sub1-3 was used to obtain 42.1 g of the product (yield: 84.7%).

[0190] The compounds belonging to Sub1 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are shown in Table 1.

[0191]

[0192]

[0193] [Table 1]

[0194] Compound FD-MS Compound FD-MS Sub 1-1 <![CDATA[m / z=396.05(C 26 H 17 Br=397.32)]]> Sub 1-2 <![CDATA[m / z=396.05(C 26 H 17 Br=397.32)]]> Sub 1-3 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-4 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-5 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-6 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-7 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-8 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-9 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-10 <![CDATA[m / z=484.20(C 35 H 29 Cl=485.07)]]> Sub 1-11 <![CDATA[m / z=510.21(C 37 H 31 Cl=511.11)]]> Sub 1-12 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-13 <![CDATA[m / z=478.155(C 35 H 23 Cl=479.02)]]> Sub 1-14 <![CDATA[m / z=518.14(C 37 H 23 C10=519.04)]]> Sub 1-15 <![CDATA[m / z=518.14(C 37 H 23 C10=519.04)]]> Sub 1-16 <![CDATA[m / z=594.18(C 43 H 27 C10=595.14)]]> Sub 1-17 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-18 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-19 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-20 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-21 <![CDATA[m / z=433.16(C 31 H 16 D5Cl=433.99)]]> Sub 1-22 <![CDATA[m / z=433.16(C 31 H 16 D5Cl=433.99)]]> Sub 1-23 <![CDATA[m / z=485.19(C 35 H 16 D7Cl=486.06)]]> Sub 1-24 <![CDATA[m / z=472.08(C 31 H 21 Br=473.41)]]> Sub 1-25 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-26 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]> Sub 1-27 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-28 <![CDATA[m / z=484.20(C 35 H 29 Cl=485.07)]]> Sub 1-29 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-30 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-31 <![CDATA[m / z=504.16(C 37 H 25 Cl=505.06)]]> Sub 1-32 <![CDATA[m / z=433.16(C 31 H 16 D5Cl=433.99)]]> Sub 1-33 <![CDATA[m / z=433.16(C 31 H 16 D5Cl=433.99)]]> Sub 1-34 <![CDATA[m / z=485.19(C 35 H 16 D7Cl=486.06)]]> Sub 1-35 <![CDATA[m / z=485.19(C 35 H 16 D7Cl=486.06)]]> Sub 1-36 <![CDATA[m / z=402.12(C 29 H 19 Cl=402.92)]]> Sub 1-37 <![CDATA[m / z=402.12(C 29 H 19 Cl=402.92)]]> Sub 1-38 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-39 <![CDATA[m / z=478.15(C 35 H 23 Cl=479.02)]]> Sub 1-40 <![CDATA[m / z=528.16(C 39 H 25 Cl=529.08)]]> Sub 1-41 <![CDATA[m / z=528.16(C 39 H 25 Cl=529.08)]]> Sub 1-42 <![CDATA[m / z=428.13(C 31 H 21 Cl=428.96)]]>

[0195] Synthesis example of Sub2

[0196] Sub2 in the above reaction formula 1 can be synthesized through the reaction pathway of the following reaction formula 3, but is not limited thereto.

[0197] <Reaction 3> (Hal 2 Hal 3 is Br, Cl or I. )

[0198]

[0199] 1. Synthesis example of Sub2-2

[0200]

[0201] (1) Synthesis example of Sub2c-2

[0202] Sub2a-2 (50 g, 177.60 mmol) and Sub2b-2 (23.82 g, 195.36 mmol) were placed in a round-bottom flask and dissolved in 450 mL of THF and 150 mL of water, and then Pd(PPh3)4 (6.15 g, 5.32 mmol) and K2CO3 (49.08 g, 355.20 mmol) were added and reacted at 70°C. After the reaction was completed, the organic layer was extracted with toluene and water, dried over MgSO4, and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 42.4 g (yield: 85.6%) of the product.

[0203] (2) Synthesis example of Sub2-2

[0204] Sub2c-2 (20 g, 71.75 mmol) and Sub2d-2 (12.14 g, 71.75 mmol) were placed in a round-bottom flask and dissolved in 240 mL of toluene, and then Pd2(dba)3 (1.97 g, 2.15 mmol), X-Phos (2.05 g, 4.30 mmol) and t-BuONa (13.79 g, 143.50 mmol) were added and reacted at 60°C. After the reaction was completed, the organic layer was extracted with toluene and water, dried over MgSO4, and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 23.5 g (yield: 79.6%) of the product.

[0205] 2. Synthesis example of Sub2-75

[0206]

[0207] (1) Synthesis example of Sub2c-75

[0208] Sub2a-75 (50 g, 168.01 mmol) and Sub2b-2 (22.53 g, 184.81 mmol) were placed in a round-bottom flask and dissolved in 450 mL of THF and 150 mL of water. Then Pd(PPh3)4 (5.82 g, 5.04 mmol) and K2CO3 (46.43 g, 336.03 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub2c-2 to obtain 34.6 g of the product (yield: 69.8%).

[0209] (2) Synthesis example of Sub2-75

[0210] Sub2c-75 (20 g, 67.84 mmol) and Sub2d-2 (11.48 g, 67.84 mmol) were placed in a round-bottom flask and dissolved in 240 mL of toluene. Then Pd2(dba)3 (1.86 g, 2.03 mmol), X-Phos (4.70 g, 4.07 mmol) and t-BuONa (13.04 g, 135.68 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub2-2 to obtain 23.4 g of the product (yield: 80.7%).

[0211] 3. Synthesis example of Sub2-76

[0212]

[0213] (1) Synthesis example of Sub2c-76

[0214] Sub2a-76 (50 g, 177.60 mmol) and Sub2b-2 (23.82 g, 195.36 mmol) were placed in a round-bottom flask and dissolved in 450 mL of THF and 150 mL of water. Then Pd(PPh3)4 (6.15 g, 5.32 mmol) and K2CO3 (49.08 g, 355.20 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub2c-2 to obtain 40.8 g of the product (yield: 82.4%).

[0215] (2) Synthesis example of Sub2-76

[0216] Sub2c-76 (20 g, 71.75 mmol) and Sub2d-76 (12.14 g, 71.75 mmol) were placed in a round-bottom flask and dissolved in 240 mL of toluene. Then Pd2(dba)3 (1.97 g, 2.15 mmol), X-Phos (2.05 g, 4.30 mmol) and t-BuONa (13.79 g, 143.50 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub2-2 to obtain 26.3 g of the product (yield: 81.2%).

[0217] 4. Synthesis example of Sub2-82

[0218]

[0219] Sub2c-76 (20 g, 71.75 mmol) and Sub2d-82 (13.14 g, 71.75 mmol) were placed in a round-bottom flask and dissolved in 240 mL of toluene. Then Pd2(dba)3 (1.97 g, 2.15 mmol), X-Phos (2.05 g, 4.30 mmol) and t-BuONa (13.79 g, 143.50 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of Sub2-2 to obtain 25.8 g of the product (yield: 84.5%).

[0220] The compounds belonging to Sub2 may be the same compounds as those described below, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 2.

[0221]

[0222]

[0223]

[0224]

[0225] [Table 2]

[0226]

[0227]

[0228]

[0229] Synthesis example of final product

[0230] 1. Synthesis Example of P1-2

[0231]

[0232] Sub1-1 (CASRN: 1257251-75-4, 15.00 g, 37.75 mmol) and Sub2-2 (15.53 g, 37.75 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene, and then Pd2(dba)3 (1.03 g, 1.13 mmol), P(t-Bu)3 (0.45 g, 2.26 mmol) and t-BuONa (7.25 g, 75.50 mmol) were added and reacted at 120°C. After the reaction was completed, the organic layer was extracted with toluene and water, dried over MgSO4, and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 23.7 g (yield: 86.3%) of the product.

[0233] 2. Synthesis Example of P1-75

[0234]

[0235] Sub1-2 (15.00 g, 37.75 mmol) and Sub2-75 (16.14 g, 37.75 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene. Then Pd2(dba)3 (1.03 g, 1.13 mmol), P(t-Bu)3 (0.45 g, 2.26 mmol) and t-BuONa (7.25 g, 75.50 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 22.5 g of the product (yield: 80.1%).

[0236] 3. Synthesis Example of P1-76

[0237]

[0238] Sub1-2 (15.00 g, 37.75 mmol) and Sub2-76 (17.04 g, 37.75 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene. Then Pd2(dba)3 (1.03 g, 1.13 mmol), P(t-Bu)3 (0.45 g, 2.26 mmol) and t-BuONa (7.25 g, 75.50 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 22.7 g of the product (yield: 78.3%).

[0239] 4. Synthesis Example of P2-50

[0240]

[0241] Sub1-5 (15.00 g, 34.96 mmol) and Sub2-50 (15.44 g, 34.96 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene. Then Pd2(dba)3 (0.96 g, 1.04 mmol), P(t-Bu)3 (0.42 g, 2.09 mmol) and t-BuONa (6.72 g, 69.93 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 24.1 g of the product (yield: 82.6%).

[0242] 5. Synthesis Example of P2-91

[0243]

[0244] Sub1-3 (15.00 g, 34.96 mmol) and Sub2-91 (21.18 g, 34.96 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene. Then Pd2(dba)3 (0.96 g, 1.04 mmol), P(t-Bu)3 (0.42 g, 2.09 mmol) and t-BuONa (6.72 g, 69.93 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 29.3 g of the product (yield: 83.9%).

[0245] 6. Synthesis Example of P2-105

[0246]

[0247] Sub1-5 (15.00 g, 34.96 mmol) and Sub2-105 (16.17 g, 34.96 mmol) were placed in a round-bottom flask and dissolved in 125 mL of toluene. Then Pd2(dba)3 (0.96 g, 1.04 mmol), P(t-Bu)3 (0.42 g, 2.09 mmol) and t-BuONa (6.72 g, 69.93 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 22.2 g of the product (yield: 74.2%).

[0248] 7. Synthesis Example of P3-6

[0249]

[0250] Sub1-30 (15.00 g, 31.31 mmol) and Sub2-6 (15.26 g, 31.31 mmol) were placed in a round-bottom flask and dissolved in 110 mL of toluene. Then Pd2(dba)3 (0.86 g, 0.94 mmol), P(t-Bu)3 (0.38 g, 1.88 mmol) and t-BuONa (6.02 g, 62.70 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 23.7 g of the product (yield: 81.36%).

[0251] 8. Synthesis Example of P3-16

[0252]

[0253] Sub1-24 (15.00 g, 31.68 mmol) and Sub2-16 (13.61 g, 31.68 mmol) were placed in a round-bottom flask and dissolved in 110 mL of toluene. Then Pd2(dba)3 (0.87 g, 0.95 mmol), P(t-Bu)3 (0.38 g, 1.90 mmol) and t-BuONa (6.09 g, 63.37 mmol) were added and synthesized in the same way as the above-mentioned synthesis method of P1-2 to obtain 20.1 g of the product (yield: 77.1%).

[0254] 9. Synthesis Example of P3-100

[0255]

[0256] Sub1-33 (15.00 g, 31.35 mmol) and Sub2-100 (17.04 g, 31.35 mmol) were placed in a round-bottom flask and dissolved in 110 mL of toluene. Then Pd2(dba)3 (0.86 g, 0.94 mmol), P(t-Bu)3 (0.38 g, 1.88 mmol) and t-BuONa (6.02 g, 62.70 mmol) were added and synthesized in the same manner as the above-mentioned synthesis method of P1-2 to obtain 22.8 g of the product (yield: 77.2%).

[0257] The FD-MS values ​​of the compounds of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 3 below.

[0258] [Table 3]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] Manufacturing and evaluation of organic electrical components

[0267] [Example 1] Green organic electric light emitting element (light emitting auxiliary layer)

[0268] After a 60 nm thick hole injection layer is formed by vacuum depositing a film of 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as "2-TNATA") on an ITO layer (anode) formed on a glass substrate, N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as "NPB") is vacuum deposited to form a 60 nm thick hole transport layer.

[0269] Afterwards, the compound P1-2 of the present invention was vacuum-deposited on the hole transport layer with a thickness of 20 nm to form a light-emitting auxiliary layer. 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") was used as the main body in the light-emitting auxiliary layer, and tri(2-phenylpyridine)iridium (hereinafter referred to as "Ir(ppy)3") was used as the doping material, and the weight ratio was 95:5. The light-emitting layer was vacuum-deposited with a thickness of 30 nm.

[0270] Next, (1,1'-biphenyl-4-hydroxy)bis(2-methyl-8-hydroxyquinoline)aluminum (hereinafter referred to as "BAlq") was vacuum deposited on the light-emitting layer with a thickness of 10 nm to form a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq3") was vacuum deposited on the hole blocking layer with a thickness of 40 nm to form an electron transport layer. Then, LiF was deposited on the electron transport layer with a thickness of 0.2 nm to form an electron injection layer, and then aluminum was deposited with a thickness of 150 nm to form a cathode.

[0271] [Example 2] to [Example 15]

[0272] An organic light emitting device was prepared in the same manner as in Example 1 except that the compounds of the present invention listed in the following Table 4 were used instead of the compound P1-2 of the present invention as the material of the light emitting auxiliary layer.

[0273] [Comparative Example 1] to [Comparative Example 3]

[0274] An organic light emitting device was prepared in the same manner as in Example 1 except that the following comparative compounds 1 to 3 were used instead of the compound P1-2 of the present invention as the material of the light emitting auxiliary layer.

[0275]

[0276] A forward bias DC voltage was applied to the organic electric light emitting elements prepared by Examples 1 to 15 of the present invention and Comparative Examples 1 to 3, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. 2 In the reference brightness, the T95 life was measured by a life measuring device manufactured by MC Science Co., Ltd. The measurement results are shown in Table 4 below.

[0277] [Table 4]

[0278]

[0279] It can be seen from Table 4 that when the organic light-emitting element material of the present invention is used as the material of the light-emitting auxiliary layer to prepare the organic light-emitting element, compared with the case of using comparison compounds 1 to 3, not only the driving voltage of the organic light-emitting element can be reduced, but also the efficiency and life can be significantly improved.

[0280] Comparative compounds 1 to 3 and the compound of the present invention have the same structure in which an amine group is bonded to the phenyl group of 9,9-diphenyl-9H-fluorene, but differ in the substituent bonded to the benzene portion of dibenzofuran substituted with an amine group.

[0281] Comparative compound 1 is similar to the compound of the present invention wherein A is the compound of the chemical formula A-1, but in the chemical formula A-1 of the compound of the present invention, Ar is substituted at a specific position of the benzene portion of dibenzofuran. 2 Instead of hydrogen, in Comparative Compounds 1 and 2, the corresponding 2 There is a difference in that the substituent is hydrogen.

[0282] Moreover, the comparative compound 3 is similar to the compound of the chemical formula A-2 in the chemical formula 1 of the present invention, but in the chemical formula A-2 of the compound of the present invention, Ar must be substituted at a specific position of the benzene part of dibenzofuran. 3 Instead of hydrogen, in comparative compound 3, it corresponds to Ar 3 There is a difference in that the substituent is hydrogen.

[0283] The compound of the present invention is based on dibenzofuran, amine and Ar 2 or Ar 3 Substitution is performed at an asymmetric position. That is, the amino group is substituted at the 1st position of dibenzofuran and the Ar 2 , or replace the amine at position 2 and Ar at position 9 3 .

[0284] On the contrary, it can be seen that the comparison compounds 2 and 3 are based on dibenzofuran, and the amino group and the phenyl group are substituted at symmetrical positions. That is, the comparison compound 2 replaces the amino group at the 1st position of dibenzofuran and replaces the phenyl group at the 9th position, and the comparison compound 3 replaces the amino group at the 2nd position of dibenzofuran and replaces the phenyl group at the 8th position.

[0285] Due to this difference, when the compound of the present invention is used as a light-emitting auxiliary layer material, the driving voltage, efficiency and lifespan are significantly improved compared to the comparative compound.

[0286] This can be explained by the LUMO values ​​of Comparative Compound 2, Comparative Compound 3, and the compound of the present invention. Referring to Table 5 below, it can be seen that the LUMO values ​​of the compound of the present invention in which the amino group and the phenyl group are symmetrically substituted based on dibenzofuran are higher than those of Comparative Compounds 2 and 3 in which the amino group and the phenyl group are symmetrically substituted.

[0287] [Table 5]

[0288] Comparative Compound 2 Comparative Compound 3 P1-1 P1-73 LUMO(eV) -1.089 -1.066 -1.028 -1.004

[0289] Therefore, the LUMO value of the compound of the present invention is higher, so that the blocking ability of electrons migrating from the light-emitting layer to the light-emitting auxiliary layer is improved compared with the comparative compound 2 or the comparative compound 3, and the light emission at the interface of the layer adjacent to the light-emitting layer of the non-light-emitting layer can be prevented, and the degradation of the interface can be prevented. The results show that when the compound of the present invention is used as a light-emitting auxiliary layer material, the life, efficiency and color purity of the element are improved.

[0290] Such results indicate that even if the core structure is similar, the physical properties of the compound, such as hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO energy levels; T1 energy levels), hole injection and mobility characteristics, and electron blocking characteristics, can differ depending on the type of substituent and the binding position of the substituent, thereby leading to completely different device results.

[0291] [Example 16] to [Example 28] Green organic electric light emitting element (light emitting auxiliary layer)

[0292] An organic light emitting device was prepared in the same manner as in Example 1 except that the compounds of the present invention listed in the following Table 5 were used instead of the compound P1-2 of the present invention as the material of the light emitting auxiliary layer.

[0293] [Comparative Example 4]

[0294] An organic light emitting device was prepared in the same manner as in Example 1 except that the following comparative compound 4 was used as the material of the light emitting auxiliary layer instead of the compound P1-2 of the present invention.

[0295] <Comparative Compound 4>

[0296]

[0297] A forward bias DC voltage was applied to the organic electric light emitting elements prepared by Examples 16 to 30 of the present invention and Comparative Examples 1 to 4, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. 2 In the reference brightness, the T95 life was measured by a life measuring device manufactured by MC Science Co., Ltd. The measurement results are shown in Table 6 below.

[0298] [Table 6]

[0299]

[0300] It can be seen from Table 6 that when the material for organic electrical light-emitting element of the present invention is used as the material of the light-emitting auxiliary layer to prepare a green organic electrical light-emitting element, compared with the case of using comparative compound 1 or comparative compound 4, not only the driving voltage of the organic electrical light-emitting element can be reduced, but also the light-emitting efficiency and life can be significantly improved.

[0301] Although Comparative Compound 1 and Comparative Compound 4 have very similar structures, they differ in that in Comparative Compound 1, hydrogen is bonded to the 4-position of 9,9-diphenyl-9H-fluorene, whereas in Comparative Compound 4, a phenyl group is substituted at the 4-position.

[0302] Comparison of Comparative Examples 1 and 4 shows that the characteristics of the device, especially the lifespan, are greatly improved in Comparative Example 4. Therefore, it can be seen that even if the compounds have similar structures, if a compound having a substituent other than hydrogen in the benzene part of 9,9-diphenyl-9H-fluorene is used as the material of the light-emitting auxiliary layer like Comparative Compound 4, it is beneficial to improve the lifespan of the device.

[0303] The compounds of the present invention used in the examples of Table 6 are the same as the comparative compound 4 in that the benzene portion of 9,9-diphenyl-9H-fluorene is substituted with a non-hydrogen substituent. However, the comparative compound 4 is different from the compounds of the present invention in that the amine group is substituted at the 1st position based on dibenzofuran, but the hydrogen is bonded at the 8th position.

[0304] That is, the compounds of the present invention used in the examples are based on dibenzofuran, with an amine group substituted at position 1 and Ar substituted at position 8. 2 , or replace the amine group at the 2nd position of dibenzofuran, replace Ar at the 9th position 3 In this way, there are substituents substituted in an asymmetrical manner on the benzene rings on both sides of dibenzofuran. In contrast, in comparative compound 4, the amino group is substituted only on the benzene ring on one side of dibenzofuran, and the benzene ring on the other side is not substituted with a substituent other than hydrogen, which is different in this point.

[0305] As can be seen from Table 6, the presence or absence of such a substituent and the bonding position etc. can lead to a significant difference in hole mobility, and such a difference may ultimately affect the characteristics of the device.

[0306] Moreover, by using the compound of the present invention as a material for the light-emitting auxiliary layer, the HOMO or LUMO energy level of the compound of the present invention can have an appropriate value between the energy levels of the hole transport layer and the light-emitting layer, thereby achieving charge balance between holes and electrons, and luminescence is formed inside the light-emitting layer rather than at the hole transport layer interface, thereby maximizing efficiency and life.

[0307] [Example 29] to [Example 41] Green organic electric light emitting element (light emitting auxiliary layer)

[0308] An organic light emitting device was prepared in the same manner as in Example 1 except that the compounds of the present invention listed in the following Table 6 were used instead of the compound P1-2 of the present invention as the material of the light emitting auxiliary layer.

[0309] [Comparative Example 5]

[0310] An organic light emitting device was prepared in the same manner as in Example 1 except that the following comparative compound 5 was used as the material of the light emitting auxiliary layer instead of the compound P1-2 of the present invention.

[0311] <Comparative Compound 5>

[0312]

[0313] A forward bias DC voltage was applied to the organic electric light emitting elements prepared by Examples 29 to 41 of the present invention and Comparative Examples 1 to 5, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. 2 In the reference brightness, the T95 life was measured by a life measuring device manufactured by MC Science Co., Ltd. The measurement results are shown in Table 7 below.

[0314] [Table 7]

[0315]

[0316] It can be seen from Table 7 that when the organic light-emitting element material of the present invention is used as the material of the light-emitting auxiliary layer to prepare a green organic light-emitting element, compared with the case of using comparative compound 1 or comparative compound 5, not only the driving voltage of the organic light-emitting element can be reduced, but also the light-emitting efficiency and life can be significantly improved.

[0317] Compared with comparison compound 1, when comparison compound 5 is used as the material of the light-emitting auxiliary layer, the device characteristics are better. In view of this, it can be seen that the characteristics of the device can be different depending on whether the phenyl group at the 9th position of 9,9-diphenyl-9H-fluorenyl is further substituted with a substituent and the type of substituent substituted on the amino group.

[0318] The compounds of the present invention used in the examples of Table 7 are the same as the comparative compound 5 in that one of the phenyl groups at the 9th position of the 9,9-diphenyl-9H-fluorenyl group is replaced with a non-hydrogen substituent, but are different in that the dibenzofuran to which the amine group substituted by the phenyl group on the other side is substituted is replaced. That is, in the compounds of the present invention, the amine group is substituted at the 1st position of the dibenzofuran, and the Ar-substituted group is substituted at the 8th position. 2 , or replace the amine group at the 2nd position of dibenzofuran, replace Ar at the 9th position 3 On the contrary, in comparative compound 5, the amine group is substituted at the 2-position of dibenzofuran and hydrogen is bonded at the 9-position, so there is a difference in this point.

[0319] Due to this difference, when the compound of the present invention is used as the material of the light-emitting auxiliary layer, the characteristics of the device are improved. In view of this, it can be seen that when substituents are substituted at specific positions of dibenzofuran, the chemical and physical properties of the compound are different, which may also affect the performance of the device.

[0320] Therefore, it can be seen from Table 4, Table 6 and Table 7 that among the amino compounds substituted with 9,9-diphenyl-9H-fluorenyl and dibenzofuran, taking dibenzofuran as the reference, in the case where the amine group is substituted on one side of the benzene ring, the compound substituted with a substituent on the other side of the benzene ring is more suitable as the material of the light-emitting auxiliary layer, and the amine group substituted on one side of the benzene ring and the substituent substituted on the other side of the benzene ring are more suitable when they are substituted at mutually asymmetric positions (when the amine group is substituted at position 1, other substituents are substituted at position 8, and when the amine group is substituted at position 2, other substituents are substituted at position 9). Moreover, the form in which at least one of the substituents is substituted in the benzene rings on both sides of the 9,9-diphenyl-9H-fluorenyl or the phenyl group combined at position 9 is substituted with a substituent is more suitable as the material of the light-emitting auxiliary layer than the compound not substituted at these positions.

[0321] The above description is for illustration only, and any person skilled in the art can make various modifications without departing from the essential characteristics of the present invention. The protection scope of the present invention should be interpreted according to the protection scope of the invention claims, and all technologies within the equivalent scope should be interpreted as included in the scope of the present invention.

Claims

1. A compound represented by chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, A is the following chemical formula A-1 or chemical formula A-2, <Chemical Formula A-1><Chemical Formula A-2> R 1 To R 9 independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ), and adjacent groups can be combined with each other to form a ring, a is an integer of 0 to 5, b to d are integers of 0 to 4, e is an integer of 0 to 5, m is an integer of 0 to 2, and f to i are integers of 0 to 3, X 1 and X 2 is O or S, L 1 and L' are independently selected from single bonds; C6~C 60 Arylene; Fluorene; C3~C 60 and C2 to C2 containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 A group consisting of a heterocyclic group, Ar 1 ,Ar 2 ,Ar 3 , R a and R b Independently selected from C6~C 60 Aryl; Fluorenyl; C3~C 60 and C2 to C2 containing at least one hetero atom selected from O, N, S, Si and P 60 A group consisting of a heterocyclic group, and The above-mentioned aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and the ring formed by the adjacent groups are each selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C1~C 20 Alkylthio, and C6~C 30 The group consisting of arylthio and arylthio may be further substituted by one or more substituents selected from the group consisting of arylthio and arylthio.

2. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by one of the following Chemical Formulas 2-1 to 2-4, In the above Chemical Formulae 2-1 to 2-4, R 1 To R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to d, f to i are the same as those defined in claim 1.

3. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by one of the following Chemical Formulas 3-1 to 3-4, In the above Chemical Formulae 3-1 to 3-4, R 1 , R 2 , R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a, b, d, f to i are the same as those defined in claim 1, R 3 is selected from deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ) group.

4. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by one of the following Chemical Formulas 4-1 to 4-8, In the above Chemical Formulae 4-1 to 4-8, R 1 , R 2 , R 4 , R 6 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a, b, d, f to i are the same as those defined in claim 1, R 3 is selected from deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; C6~C 60 The aryloxy group and -L'-N(R a )(R b ) group.

5. The compound according to claim 1, wherein The above chemical formula 1 is represented by the following chemical formula 5-1 or chemical formula 5-2, In the above Chemical Formula 5-1 and Chemical Formula 5-2, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as those defined in claim 1.

6. The compound according to claim 1, wherein The above chemical formula 1 is represented by the following chemical formula 6-1 or chemical formula 6-2, In the above Chemical Formula 6-1 and Chemical Formula 6-2, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as those defined in claim 1.

7. The compound according to claim 1, wherein The above chemical formula 1 is composed of the following chemical formulas 7-1 to 7-4, In the above Chemical Formula 7-1 to Chemical Formula 7-4, R 1 To R 9 , X 1 , X 2 , L 1 ,Ar 1 To Ar 3 , a to i are the same as those defined in claim 1.

8. The compound according to claim 1, wherein Ar 1 To Ar 3 At least one of the following chemical formulae Ar-1 to Ar-6 is selected from the group consisting of: In the above chemical formula Ar-1 to chemical formula Ar-6, R 11 To R 16 independently selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, and C6~C 20 The adjacent groups can be combined with each other to form a ring. m is an integer of 0 to 5, n, p, q, and r are integers of 0 to 4, and o is an integer of 0 to 3. When they are integers of 2 or more, R 13 Respectively, R 14 Respectively, R 15 Respectively, R 16 The same or different, Y is S, O, C(R1)(R2) or N(R3), R a is selected from a single bond; C1~C 20 Alkylene; C6~C 30 arylene; fluorene; C2~C 30 A heterocyclic group; and C2~C 30 aliphatic ring groups, and R1 to R3, R b independently selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, and C6~C 20 and R1 and R2 may be combined with each other to form a ring.

9. The compound according to claim 1, wherein Ar 2 and Ar 3 C6~C 60 The aromatic group.

10. The compound according to claim 1, wherein The compound represented by the above chemical formula 1 is one of the following compounds:

11. An organic electrical element, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein: The organic layer comprises the compound of Chemical Formula 1 of claim 1.

12. The organic electric element according to claim 11, wherein The organic layer includes a light-emitting layer between the first electrode and the second electrode, and a light-emitting auxiliary layer between the light-emitting layer and the first electrode, wherein the light-emitting auxiliary layer includes the compound.

13. The organic electric element according to claim 11, wherein The organic layer includes two or more stacks, and the stack includes a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first layer.

14. The organic electric element according to claim 13, wherein The organic layer further includes a charge generation layer formed between the two or more stacks.

15. The organic electric element according to claim 11, wherein The organic electrical element further includes a light efficiency improvement layer, and the light efficiency improvement layer is formed on a surface of the first electrode or the second electrode that is not in contact with the organic layer.

16. An electronic device, wherein: include: A display device comprising the organic electric element according to claim 11; as well as The control unit is used to drive the display device.

17. The electronic device according to claim 16, wherein: The organic electrical element is selected from the group consisting of an organic electrical light-emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, an element for monochromatic lighting, and an element for quantum dot display.

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