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, the organic material layer including the compound represented by chemical formula 1, and an electronic device including the organic electric element. Therefore, the driving voltage of the organic electric element can be reduced, and the luminous efficiency and the service life of the organic electric element 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] The so-called organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic electrical element based on this light-emitting phenomenon usually includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. In order to improve the light-emitting efficiency and stability of the organic electrical element, the organic layer is usually constituted as a multilayer structure formed by a variety of different organic materials. For example, the organic layer may include multiple sublayers such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] In organic electrical elements, the materials used as organic layers can be divided into luminescent materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. In addition, the luminescent materials can be divided into high molecular weight and low molecular weight according to the molecular weight, and can be divided into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to the luminescence mechanism. In addition, the luminescent materials can be divided into blue, green and red luminescent materials according to the luminescent colors, as well as yellow and orange luminescent materials required to better achieve natural colors.

[0004] On the other hand, when a substance is used as a light-emitting material, there are problems that the maximum emission wavelength is shifted to a longer wavelength due to the interaction between molecules, and the efficiency of the element is reduced due to the reduction of pure chromaticity or the effect of luminescence attenuation. Therefore, in order to increase the luminous efficiency by increasing the pure chromaticity and transferring energy, a matrix / doping type can be used as a light-emitting material. The principle is that if a small amount of dopant with a smaller energy band interval is mixed into the light-emitting layer compared to the main body forming the light-emitting layer, the excitons generated in the light-emitting layer are transferred to the dopant, so that light with high efficiency is emitted. At this time, since the wavelength of the main body moves to the wavelength band of the dopant, it is impossible to obtain light of the desired wavelength according to the type of dopant used.

[0005] Currently, the portable display market is experiencing a trend of increasing in size due to large-area displays, which requires a larger power consumption than conventional portable displays. Therefore, for portable displays with a limited power supply source, namely batteries, power consumption becomes a very important factor, and efficiency and lifespan issues also become situations that must be addressed.

[0006] Efficiency, lifespan, and driving voltage are interrelated. If efficiency increases, the driving voltage decreases relatively. When the driving voltage is reduced, the crystallization of organic substances based on Joule heating decreases, and ultimately the lifespan tends to increase. However, even if the organic layer is simply improved, the efficiency cannot be maximized. This is because only when the energy level and T between the organic layers are 1 Only when the optimal combination of value and the inherent properties of the material (mobility, surface properties, etc.) is achieved can long life and high efficiency be achieved at the same time.

[0007] Therefore, it is urgent to develop luminescent materials with high thermal stability and capable of effectively achieving charge balance in the luminescent layer. That is, in order to give full play to the excellent properties of organic electrical components, various substances constituting the organic layer in the components, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injection materials, must first be supported by stable and efficient materials. Among them, it is particularly necessary to develop host materials for the luminescent layer. Summary of the invention

[0008] Technical issues

[0009] 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.

[0010] Technical Solution

[0011] In one aspect, the present invention provides a compound represented by the following chemical formula.

[0012] (A is )

[0013] In another aspect, the present invention provides a method for recovering a compound, wherein the compound can be recovered and reused after evaporating the compound represented by the chemical formula.

[0014] In another aspect, the present invention provides an organic electric element and an electronic device using the compound represented by the chemical formula.

[0015] In another aspect, the present invention also provides an organic electrical element and an electronic device thereof comprising the compound represented by the chemical formula and a compound represented by the following chemical formula.

[0016]

[0017] Effects of the Invention

[0018] By using the compounds of the embodiments of the present invention, not only can the driving voltage of the element be reduced, but also the luminous efficiency and life span can be improved, and the compounds used in the evaporation process can be recovered for reuse. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0020] Description of Reference Numerals

[0021] 100, 200, 300: organic electrical element 110: first electrode

[0022] 120: hole injection layer 130: hole transport layer

[0023] 140: Light-emitting layer 150: Electron transport layer

[0024] 160: electron injection layer 170: second electrode

[0025] 180: Light efficiency improvement layer 210: Buffer layer

[0026] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0027] 330: first hole transport layer 340: first light emitting layer

[0028] 350: first electron transport layer 360: first charge generation layer

[0029] 361: second charge generation layer 420: second hole injection layer

[0030] 430: second hole transport layer 440: second light emitting layer

[0031] 450: Second electron transport layer CGL: Charge generation layer

[0032] ST1: First stack ST2: Second stack DETAILED DESCRIPTION

[0033] 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.

[0034] 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.

[0035]

[0036] 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.

[0037] 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 having 2 to 60 carbon atoms containing one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" used in the present invention, unless otherwise specified, means an element other than carbon, such as N, O, S, P or Si, and may also include SO in place of carbon forming the ring, as in the following compounds: 2 The heterocyclic group means a monocyclic type, a ring aggregate, a fused polycyclic type, a spirocyclic compound, etc. containing a heteroatom.

[0038]

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043]

[0044] 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.

[0045]

[0046] Also, unless otherwise specified in this specification, "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-ring may mean a single ring form. For example, naphthalene corresponds to a 2-ring condensed ring, anthracene corresponds to a 3-ring condensed ring, thiophene, furan, etc. correspond to 5-atom rings, and benzene and pyridine correspond to 6-atom rings.

[0047] Also, unless otherwise specified in this specification, a ring formed by the bonding of adjacent groups to each other is selected from the group consisting of C 6 ~C 60 aromatic ring group; fluorenyl group; C containing at least one heteroatom selected from O, N, S, Si, and P 2 ~C 60 heterocyclic group; and C 3 ~C 60 aliphatic ring group. Here, the aromatic ring group may be an aromatic ring, and the heterocyclic group may include a heteroaromatic ring.

[0048] Unless otherwise specified in this specification, "between adjacent groups" means that, taking the following chemical formula as an example, not only between R 1 and R 2 , between R 2 and R 3 , between R 3 and R 4 , between R 5 and R 6 , but also includes between R 7 and R 8 sharing a carbon, and may also include substituents bonded to ring-constituting elements (such as carbon or nitrogen) that are not directly adjacent like between R 1 and R 7 , between R 1 and R 8 or between R 4 and R 5 . That is, when there are substituents on directly adjacent ring-constituting elements such as carbon or nitrogen, they can be regarded as adjacent groups; but if there are no substituents on directly adjacent ring-constituting elements, the substituents bonded to the next ring-constituting element can be regarded as adjacent groups; in addition, substituents bonded to the same ring-constituting carbon can also be regarded as adjacent groups. In the following chemical formula, when substituents bonded to the same carbon like R 7 and R 8 combine with each other to form a ring, a compound containing a spiro ring part can be formed.

[0049]

[0050] Moreover, in the present specification, the expression "adjacent groups may combine with each other to form a ring" is used with the same meaning as "adjacent groups combine with each other to selectively form a ring", and means a case where at least one pair of adjacent groups combine with each other to form a ring.

[0051] Moreover, in the present specification, unless otherwise specified, substituents such as aryl, arylene, fluorenyl, fluorenylene, heterocyclic group, aliphatic cyclic group, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkylthio, arylthio, etc., and rings formed by the combination of adjacent groups, etc., can each be selected from the group consisting of deuterium, halogen, cyano, nitro, siloxy group, C 6 ~C 30 aryl, fluorenyl, C containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P 2 ~C 30 heterocyclic group, C 3 ~C 30 aliphatic cyclic group, C 1 ~C 20 alkyl, C 2 ~C 20 alkenyl, C 2 ~C 20 alkynyl, C 1 ~C 20 alkoxy, C 6 ~C 20 aryloxy, C 1 ~C 20 alkylthio, C 6 ~C 20 arylthio, C 1 ~C 20 alkyl or C 6 ~C 20 aryl-substituted or unsubstituted silyl group, and C 1 ~C 20 alkyl or C 6 ~C 20 aryl-substituted or unsubstituted phosphinyl group are further substituted by one or more substituents selected from the group consisting of.

[0052] Next, with reference to Figures 1 to 3 , the laminated structure of the organic electrical element containing the compound of the present invention will be described.

[0053] In the process of attaching reference numerals to the structural elements of each drawing, it should be noted that the same structural elements are given the same reference numerals as much as possible even if they are shown in different drawings. And, in the process of describing the present invention, in the case where the specific description of the relevant well-known structure or function will obscure the gist of the present invention, the detailed description will be omitted.

[0054] 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.

[0055] 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.

[0056] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0057] 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).

[0058] 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.

[0059] 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 containing no organic matter.

[0060] Specifically, 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 may be sequentially formed on the first electrode 110 .

[0061] Preferably, a light efficiency improvement layer 180 may be formed on the side of the first electrode 110 or the second electrode 170 that is 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] Although not shown in Figure 2 An electron transport auxiliary layer may also be formed between the light emitting layer 140 and the electron transport layer 150 .

[0066] 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.

[0067] 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.

[0068] 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 .

[0069] 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.

[0070] 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.

[0071] 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.

[0072] exist Figure 3 In 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.

[0073] 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.

[0074] 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 of the hole injection layer 120, 320, 420, the hole transport layer 130, 330, 430, the buffer layer 210, the light-emitting auxiliary layer 220, the electron transport layer 150, 350, 450, the light-emitting layer 140, 340, 440 or the light efficiency improvement layer 180, preferably, the material of the light-emitting layer 140, 340, 440, or / and the light efficiency improvement layer 180, more preferably, the main body of the light-emitting layer 140, 340, 440.

[0075] Even for the same or similar cores, the band gap, electrical properties, surface properties, etc. may differ depending on which substituent is bonded at which position, so 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 between the organic layers and T 1 When the optimal combination of the intrinsic properties of the material (mobility, surface properties, etc.) is achieved, long life and high efficiency can be achieved at the same time.

[0076] Therefore, the compound represented by Chemical Formula 1 in the present invention is used as the material of the light emitting layers 140, 340, and 440, so that the energy level between the organic layers and T 1 The value, inherent properties (mobility, surface properties, etc.) are optimized, while the life and efficiency of organic electrical components are improved.

[0077] The organic electrical light-emitting element of one embodiment of the present invention can be prepared by a variety of 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.

[0078] 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.

[0079] 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.

[0080] Furthermore, the organic electrical element according to an embodiment of the present invention may be 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.

[0081] 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.

[0082] Hereinafter, the compound according to one aspect of the present invention will be described.

[0083] A compound according to one aspect of the present invention is represented by Chemical Formula 1 below.

[0084]

[0085] In the chemical formula 1, each symbol can be defined as follows.

[0086] X and Y are independently N, O or S, and one of them is N and the other is O or S. In a five-membered ring containing X and Y, when X is N and Y is O or S, the bond between XCY represents Ar 1 The carbon bonded to X forms a double bond, and Ar 1 The carbon to which it is attached forms a single bond with Y; when X is O or S and Y is N, Ar 1 The carbon to which it is attached forms a single bond with X, and Ar 1 The bound carbon forms a double bond with Y.

[0087] Ar 1 and Ar 2 Independently selected from C 6 ~C 60 Aryl; Fluorenyl; C 3 ~C 60 and C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group.

[0088] L 1 and L 2 are independently selected from single bonds; C 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group.

[0089] A is the chemical formula A.

[0090] Z is selected from O or S.

[0091] R 1 To R 4 , R a independently selected from hydrogen; deuterium; halogen; cyano; nitro; C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 Heterocyclic group; C 3 ~C 60 Aliphatic ring group; C 1 ~C 20 Alkyl; C 2 ~C 20 Alkenyl; C 2 ~C 20 Alkynyl; C 1 ~C 20 Alkoxy; and C 6 ~C 60 The adjacent R 3 Between or adjacent R 4 The groups may combine with each other to form a ring.

[0092] a is an integer of 0 to 7, b and c are integers of 0 to 3 respectively, and d is an integer of 0 to 4.

[0093] Between adjacent groups, for example, adjacent R 3 Between, adjacent R 4 At least one pair of the rings formed by bonding to each other can be selected from C 6 ~C 60 An aromatic ring group; a fluorenyl group; a C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 60 A heterocyclic group; and C 6 ~C 60 A group consisting of aliphatic ring groups.

[0094] When the ring formed by the combination of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C 6 ~C 20 , C 6 ~C 18 , C 6 ~C 16 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C6 ~C 10 , C 6 , 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.

[0095] In the Ar 1 ,Ar 2 , R 1 To R 4 , R a When at least one of the groups is an aryl group, the aryl group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C15 , C 16 , C 17 , C 18 The aryl group includes phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene and the like.

[0096] In the L 1 and L 2 When at least one of the groups is an arylene group, the arylene group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18The arylene group includes phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene and the like.

[0097] In the Ar 1 ,Ar 2 , R 1 To R 4 , R a , L 1 and L 2 When at least one of the groups is a heterocyclic group, the heterocyclic group may be, for example, C 2 ~C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C6 , C 2 ~C 5 , C 2 ~C 4 , C 2 ~C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , 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 and the like, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, 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, dibenzocarbazole, indole

[0063] The invention also includes benzofuranopyridine, benzothienopyridine, benzofuranopyridine, benzothienopyrimidine, benzofuranopyrimidine, benzothienopyrazine, benzofuranopyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilane (benzosilol), 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], and the like.

[0098] In the Ar 1 ,Ar 2 , R1 To R 4 , R a , L 1 and L 2 When at least one of the groups is an aliphatic ring group, the aliphatic ring group may be, for example, C 3 ~C 30 , C 3 ~C 29 , C 3 ~C 28 , C 3 ~C 27 , C 3 ~C 26 , C 3 ~C 25 , C 3 ~C 24 , C 3 ~C 23 , C 3 ~C 22 , C 3 ~C 21 , C 3 ~C 20 , C 3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 The aliphatic ring group of the present invention is specifically, a cyclopentyl group, a cyclohexyl group, a norbornyl group, an adamantyl group and the like.

[0099] In the R1 To R 4 , R a When at least one of the alkyl groups is an alkyl group, the alkyl group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , C 4 The alkyl group of the present invention can be alkyl, for example, methyl, ethyl, tert-butyl, etc.

[0100] The aryl group, arylene group, fluorenyl group, fluorenyl group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and adjacent R 3 Between or adjacent R 4 The rings formed by the mutual bonding of the groups can be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

[0101] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, adjacent R3 Between or adjacent R 4 When at least one of the rings formed by the groups being bonded to each other is further substituted by an aryl group, the aryl group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Etc. aromatic groups.

[0102] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, adjacent R 3 Between or adjacent R 4 When at least one of the rings formed by the groups mutually bonded is further substituted by an aliphatic ring group, the aliphatic ring group may be, for example, C3 ~C 30 , C 3 ~C 29 , C 3 ~C 28 , C 3 ~C 27 , C 3 ~C 26 , C 3 ~C 25 , C 3 ~C 24 , C 3 ~C 23 , C 3 ~C 22 , C 3 ~C 21 , C 3 ~C 20 , C 3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 The aliphatic ring group of the present invention is specifically, a cyclopentyl group, a cyclohexyl group, a norbornyl group, an adamantyl group and the like.

[0103] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, adjacent R 3 Between or adjacent R 4When at least one of the rings formed by the groups mutually bonding is further substituted by an alkyl group, the alkyl group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , C 4 The alkyl group of the present invention can be alkyl, for example, methyl, ethyl, tert-butyl, etc.

[0104] The chemical formula 1 can be expressed as any one of the following chemical formulas 1-1 to 1-6.

[0105]

[0106] In the chemical formulas 1-1 to 1-6, X, Y, and R 1 , R 2 , R a , L 1 , L 2 ,Ar 1 ,Ar 2 , A, a and b are the same as defined in Chemical Formula 1.

[0107] The chemical formula A can be represented by any one of the following chemical formulas A-1 to A-4, but is not limited thereto.

[0108]

[0109] In the chemical formulas A-1 to A-4, Z, R 3 , R 4 , c and d are the same as defined in Chemical Formula 1.

[0110] The L 1 or L 2 The compound may be selected from the group consisting of the following Chemical Formula L-1 to Chemical Formula L-3.

[0111]

[0112] In the chemical formula L-1 to the chemical formula L-3, * represents the binding position, R 5 and R 6 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The group is composed of aliphatic ring groups, adjacent groups can be combined with each other to form a ring, e is an integer from 0 to 4, and f is an integer from 0 to 6.

[0113] The chemical formula L1 may be expressed as any one of the following chemical formulas L1-1 to L1-3.

[0114]

[0115] In the chemical formulas L1-1 to L1-3, R 5 , e and * are the same as defined in Chemical Formula L1.

[0116] The chemical formula L2 may be expressed as any one of the following chemical formulas L2-1 to L2-6.

[0117]

[0118]

[0119] In the chemical formulas L2-1 to L2-6, R 6 , f and * are the same as defined in Chemical Formula L2.

[0120] The chemical formula L3 may be expressed as any one of the following chemical formulas L3-1 to L3-4.

[0121]

[0122] In the chemical formula L3-1 to the chemical formula L3-4, R 6 , f and * are the same as defined in Chemical Formula L3.

[0123] Specifically, the compound represented by Chemical Formula 1 may be one of the following compounds, but is not limited thereto.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] The compound represented by the chemical formula 1 has a reorganization energy (RE) value of 0.10 to 0.19, preferably 0.11 to 0.17.

[0130] Next, the reorganization energy will be described.

[0131] Reorganization Energy refers to the energy consumed by the change in molecular structure arrangement when charges (electrons, holes) move. It depends on the molecular geometry, and has the characteristic that the smaller the difference between the potential energy surface (PES) of the neutral state and the PES of the charged state, the smaller the reorganization energy value. The RE value can be calculated by the calculation formula shown below.

[0132] RE hole :λ + =(E NOCE -E COCE )+(E CONE -E NONE )

[0133] RE elec :λ - =(E NOAE -E AOAE )+(E AONE -E NONE )

[0134] NONE: Neutral geometry of neutral molecules (=NO opt.)

[0135] NOAE: Anion geometry of neutral molecules

[0136] NOCE: Cation geometry of neutral molecules

[0137] AONE: Neutral Geometry of Anion Molecules

[0138] AOAE: Anion geometry of anionic molecules (=AO opt.)

[0139] CONE: Neutral geometry of cation molecules

[0140] COCE: cationic geometry of the cationic molecule (=CO optimization (CO opt.))

[0141] The reorganization energy value is inversely proportional to the charge mobility. Under the conditions of having the same r and T values, the RE value of each material directly affects the mobility.

[0142] The relationship between the RE value and the mobility is expressed as follows, and is explained using a charge transfer matrix element.

[0143]

[0144] λ: Reorganization energy

[0145] μ: mobility

[0146] r: dimer displacement

[0147] t: intermolecular charge transfer matrix element

[0148] According to the above formula, it can be seen that the smaller the RE value is, the faster the mobility of the charge is.

[0149] In order to find the reorganization energy value, a simulation tool that can calculate the potential energy based on the molecular structure is required. For example, Gaussian09 (hereinafter referred to as G09) and Schrodinger Materials Science's Jaguar (hereinafter referred to as JG) module can be used. Both G09 and JG are tools for analyzing the properties of molecules through quantum mechanics (QM) calculations, and have the function of optimizing molecular structures or calculating the energy (single-point energy) for existing molecular structures.

[0150] In molecular structures, the QM calculation process requires large computing resources. For example, two cluster servers can be used for such calculations. Each cluster server consists of four node workstations and one master workstation. Each node uses a central processing unit (CPU) with more than 36 cores to perform molecular QM calculations through symmetric multi-processing (SMP) parallel computing.

[0151] G09 was used to calculate the optimized molecular structures and their potential energies (NONE / COCE) in the neutral / charged states required for the reorganization energy. The charge potential energy (NOCE) of the structure optimized for the neutral state and the neutral potential energy (CONE) of the structure optimized for the charge state were calculated by changing only the charge in the two optimized structures. The reorganization energy was then calculated according to the following relationship.

[0152] RE charge :λ=(E NOCE -E COCE )+(E CONE -E NONE )

[0153] Since Schrödinger provides the function of automatically performing this calculation process, the potential energy of each state can be calculated in turn through the JG module, and the RE value can be calculated by only providing the molecular structure (NO) of the basic state.

[0154] According to another embodiment of the present invention, the present invention provides an organic electrical element, which includes 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 as shown in Chemical Formula 1.

[0155] The organic layer includes a phosphorescent light emitting layer, and the phosphorescent light emitting layer includes a compound shown in Chemical Formula 1 and a compound shown in the following Chemical Formula 2.

[0156] <Chemical Formula 2>

[0157]

[0158] In the chemical formula, each symbol can be defined as follows.

[0159] X 1 To X 3 are independently C(R') or N, and X 1 To X 3 At least one of them is N.

[0160] L 4 To L 6 are independently selected from single bonds; C 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group.

[0161] Ar 5 To Ar 7 Independently selected from C 6 -C 60 Aryl; Fluorenyl; C 3 -C 60 and a C 2 -C 60 A group consisting of a heterocyclic group.

[0162] R' is independently selected from hydrogen; deuterium; halogen; cyano; nitro; C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 Heterocyclic group; C 3 ~C 60 Aliphatic ring group; C 1 ~C 20 Alkyl; C 2 ~C 20 Alkenyl; C 2 ~C 20 Alkynyl; C 1 ~C 20 Alkoxy; and C 6 ~C 60 A group composed of aryloxy groups.

[0163] In the Ar 5 To Ar 7 When at least one of R and R' is an aryl group, the aryl group may be, for example, C6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , 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.

[0164] In the L 4 To L 6 When at least one of the groups is an arylene group, the arylene group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene, etc. Preferably, L 3 It may be phenyl, biphenyl or terphenyl.

[0165] In the Ar 5 To Ar 7 , R', L 4 To L 6 When at least one of the groups is a heterocyclic group, the heterocyclic group may be, for example, C 2 ~C 30 , C 2 ~C29 、C 2 ~C 28 、C 2 ~C 27 、C 2 ~C 26 、C 2 ~C 25 、C 2 ~C 24 、C 2 ~C 23 、C 2 ~C 22 、C 2 ~C 21 、C 2 ~C 20 、C 2 ~C 19 、C 2 ~C 18 、C 2 ~C 17 、C 2 ~C 16 、C 2 ~C 15 、C 2 ~C 14 、C 2 ~C 13 、C 2 ~C 12 、C 2 ~C 11 、C 2 ~C 10 、C 2 ~C 9 、C 2 ~C 8 、C 2 ~C 7 、C 2 ~C 6 、C 2 ~C 5 、C 2 ~C 4 、C 2 ~C 3 、C 2 、C 3 、C 4 、C 5 、C 6 、C 7 、C 8 、C 9 、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 and the like, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, 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, dibenzocarbazole, indole

[0063] The invention also includes benzofuranopyridine, benzothienopyridine, benzofuranopyridine, benzothienopyrimidine, benzofuranopyrimidine, benzothienopyrazine, benzofuranopyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilane (benzosilol), 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], and the like.

[0166] In the Ar 5 To Ar 7 At least one of R' is fluorenyl or L 4 To L 6 When at least one of the fluorenyl groups is a fluorenyl group, the fluorenyl group or the 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, etc.

[0167] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, can be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

[0168] When at least one of the aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, and aryloxy groups is further substituted with an aryl group, the aryl group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17, C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , 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 aryl groups such as etc.

[0169] When at least one of the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group is further substituted by a heterocyclic group, the heterocyclic group may be, for example, C 2 ~C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2~C 18 、C 2 ~C 17 、C 2 ~C 16 、C 2 ~C 15 、C 2 ~C 14 、C 2 ~C 13 、C 2 ~C 12 、C 2 ~C 11 、C 2 ~C 10 、C 2 ~C 9 、C 2 ~C 8 、C 2 ~C 7 、C 2 ~C 6 、C 2 ~C 5 、C 2 ~C 4 、C 2 ~C 3 、C 2 、C 3 、C 4 、C 5 、C 6 、C 7 、C 8 、C 9 、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 and other heterocyclic groups.

[0170] When at least one of the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group is further substituted by a fluorenylene group, the fluorenyl group can be 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.

[0171] Ar 5 To Ar 7 At least one of the compounds may be selected from the group consisting of the following chemical formulas Ar-1 to Ar-8.

[0172]

[0173]

[0174] In the chemical formula Ar-1 to the chemical formula Ar-8, each symbol can be defined as follows.

[0175] X 11 and X 12 Independently of each other, N(Ar 11 ), O, S or C (R 17 )(R 18 ).

[0176] R 11 To R 18 independently selected from hydrogen; deuterium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 17 and R 18 Can combine with each other to form a ring. 17 and R 18 When they combine with each other to form a ring, a spiro compound is formed.

[0177] ta, tb, td are each an integer from 0 to 4, tc is an integer from 0 to 6, te is an integer from 0 to 7, and tf is an integer from 0 to 5.

[0178] Ar 11 Choose from C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 Heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic cyclic groups.

[0179] The chemical formula 2 may be expressed as any one of the following chemical formulas 2-1 to 2-6.

[0180]

[0181]

[0182] In the chemical formula 2-1 to the chemical formula 2-6, L 4 To L 6 ,Ar 6 and Ar 7 Same as defined in Chemical Formula 2.

[0183] X 11 , X 13 , X 15 and X 21 Independently of each other 11 , O, S or C (R 17 )(R 18 ), X 12 , X 14 and X 16 are independently single bonds, N(Ar 12 ), O, S or C (R 21 )(R 22 ).

[0184] Ar 11 and Ar 12 Independently selected from C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic ring groups.

[0185] R 11 To R 18 , R 21 , R 22 independently selected from hydrogen; deuterium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 17 and R 18 Can combine with each other to form a ring, R 21 and R 22 Can combine with each other to form a ring. 17 and R 18 Combined with each other, or R 21 and R22 When they combine with each other to form a ring, a spiro compound is formed.

[0186] a', d', f' are integers from 0 to 4, b', c', e' are integers from 0 to 3, ta, tb, td are integers from 0 to 4, te is an integer from 0 to 7, and tf is an integer from 0 to 5.

[0187] In the chemical formula 2, L 4 To L 6 At least one of the compounds may be selected from the group consisting of the following Chemical Formula b-1 to Chemical Formula b-13.

[0188]

[0189]

[0190] In the chemical formula b-1 to chemical formula b-13, each symbol can be defined as follows.

[0191] Z 10 S, O, C (R 1 )(R 2 ) or N(R 3 ).

[0192] Z 49 To Z 51 Independently of each other, C(R 4 ) or N, and at least one of them is N.

[0193] R 19 To R 24 , R 1 To R 4 independently selected from hydrogen; deuterium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 1 and R 2 Can combine with each other to form a ring. 1 and R 2 When they combine with each other to form a ring, a spiro compound is formed.

[0194] a", c", d" and e" are each an integer from 0 to 4, b" is an integer from 0 to 6, f" and g" are each an integer from 0 to 3, h" is an integer from 0 to 2, and i" is an integer from 0 to 3.

[0195] Specifically, the compound represented by Chemical Formula 2 may be one of the following compounds, but is not limited thereto.

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] In another aspect, the present invention further provides an electronic device including a display device including an organic electric element, and a control unit for driving the display device, wherein the organic electric element includes the compound shown in Chemical Formula 1.

[0212] On the other hand, the present invention provides a compound represented by the chemical formula 1. In the process of preparing an organic electrical element, after evaporating an organic layer, the material of the organic layer is recovered from the evaporation device, and then the compound is obtained by purification. The purity of the recovered and purified compound is above 99.9%.

[0213] On another aspect, the present invention provides a method for recovering the compound represented by the chemical formula 1, comprising: a step of vapor-depositing an organic layer material containing the compound represented by the chemical formula 1; a step of recovering the organic layer material attached to the vapor-deposition equipment; and a step of purifying the recovered organic layer material to obtain a compound represented by the chemical formula 1 with a purity of more than 99.9%.

[0214] The purification step may include: a step of recrystallizing the recovered organic layer material using a recrystallization solvent; a step of performing adsorption separation using an adsorbent; and a step of sublimation purification.

[0215] The recrystallization step may include a preliminary purification process using a recrystallization solvent to obtain the compound represented by the Chemical Formula 1 with a purity of 98%.

[0216] Preferably, as the recrystallization solvent, a polar solvent having a polarity value (polarity index (PI)) of 5.5 to 7.2 or a mixture of a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7 can be used.

[0217] When a polar solvent and a non-polar solvent are mixed and used as a recrystallization solvent, the non-polar solvent can be used in a ratio of 15% (v / v) or less to the polar solvent.

[0218] Moreover, preferably, a single solvent of methylpyrrolidone (NMP) can be used; or a mixed polar solvent of any one selected from the group consisting of 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide can be mixed with the methylpyrrolidone; or a single or mixed non-polar solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate and butanone can be used; or a mixed polar solvent and a non-polar solvent can be used as the recrystallization solvent.

[0219] The preliminary purification process may include: after dissolving the unpurified organic light-emitting material recovered from the evaporation equipment in a polar solvent at 90° C. to 120° C., cooling to 0° C. to 5° C. to precipitate crystals.

[0220] The preliminary purification process may include: after dissolving the unpurified organic light-emitting material recovered from the evaporation equipment in a polar solvent at 90° C. to 120° C., cooling to 35° C. to 40° C., adding a non-polar solvent, cooling to 0° C. to 5° C., and precipitating crystals.

[0221] The preliminary purification process may include: after dissolving the unpurified organic light-emitting material recovered from the evaporation device in a non-polar solvent, concentrating the solvent and removing the non-polar solvent while precipitating crystals.

[0222] The preliminary purification process may include: firstly performing recrystallization with a polar solvent and then performing recrystallization again with a non-polar solvent.

[0223] In the adsorptive separation step using the adsorbent, activated carbon, silica gel, alumina or a substance known for adsorption purposes can be used as the adsorbent.

[0224] Hereinafter, examples are given to specifically describe the synthesis examples of the compounds represented by Chemical Formula 1 and Chemical Formula 2 and the preparation examples of the organic electric device of the present invention, but the present invention is not limited to the following examples.

[0225] [Synthesis Example 1] Compound of Chemical Formula 1

[0226] The compound represented by Chemical Formula 1 according to the present invention (ie, the final product) can be synthesized by reacting Sub1 with Sub2 as shown in the following Reaction Formula 1, but the present invention is not limited thereto.

[0227] <Reaction formula 1>

[0228]

[0229] I. Synthesis example of Sub1

[0230] Sub1 in the reaction formula 1 is synthesized according to the method disclosed in Korean registered patent No. 10-2112786 (registered on May 13, 2020). The compound belonging to Sub1 may be the same compound as the following compound, but is not limited thereto. The FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are respectively listed in Table 1.

[0231]

[0232]

[0233] [Table 1]

[0234] Compound FD-MS Compound FD-MS Sub1-1 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-2 <![CDATA[m / z=334.09(C 21 H 7 D 5 ClNO=334.81)]]> Sub1-3 <![CDATA[m / z = 405.09 (C 27 H 16 ClNO = 405.88)]]> Sub1-4 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-5 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]> Sub1-6 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-7 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]> Sub1-8 <![CDATA[m / z=471.08(C 31 H 18 ClNS=472)]]> Sub1-9 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-10 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-11 <![CDATA[m / z=411.14(C 27 H 22 ClNO=411.93)]]> Sub1-12 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-13 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-14 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-15 <![CDATA[m / z=455.11(C 31 H 18 ClNO=455.94)]]> Sub1-16 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]> Sub1-17 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-18 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]> Sub1-19 <![CDATA[m / z=350.07(C 21 H 7 D 5 ClNS=350.87)]]> Sub1-20 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-21 <![CDATA[m / z=334.09(C 21 H 7 D 5 ClNO=334.81)]]> Sub1-22 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-23 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-24 <![CDATA[m / z=405.09(C 27 H 16 ClNO=405.88)]]> Sub1-25 <![CDATA[m / z=455.11(C 31 H 18 ClNO=455.94)]]> Sub1-26 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]> Sub1-27 <![CDATA[m / z=329.06(C 21 H 12 ClNO=329.78)]]> Sub1-28 <![CDATA[m / z=345.04(C 21 H 12 ClNS=345.84)]]>

[0235] II. Synthesis example of Sub2

[0236] Sub2 of the reaction formula 1 can be synthesized through the reaction pathway of the following reaction formula 2, but is not limited thereto.

[0237] <Reaction 2>

[0238]

[0239] 1. Synthesis example of Sub2-1

[0240]

[0241] Sub2-1-a (10.0 g, 107 mmol) was dissolved in toluene (540 mL), and Sub2-1-b (34.7 g, 107 mmol), Pd 2 (dba) 3 (2.95 g, 3.22 mmol), P(t-Bu) 3 (1.30 g, 6.44 mmol) and NaOt-Bu (20.6 g, 215 mmol) were reacted at 80 °C. After the reaction, CH 2Cl 2 The organic layer was extracted with MgSO 4 After drying, the concentrate was concentrated, and then separated by passing through a silica gel column and recrystallized to obtain 25.9 g (yield 72%) of a product.

[0242] 2. Synthesis example of Sub2-4

[0243]

[0244] Sub2-1-a (10.0 g, 107 mmol) was dissolved in toluene (540 mL), and Sub2-4-b (34.7 g, 107 mmol), Pd 2 (dba) 3 (2.95 g, 3.22 mmol), P(t-Bu) 3 (1.30 g, 6.44 mmol) and NaOt-Bu (20.6 g, 215 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 27.4 g of the product (yield 76%).

[0245] 3. Synthesis example of Sub2-16

[0246]

[0247] Sub2-1-a (5.0 g, 53.7 mmol) was dissolved in toluene (270 mL), and Sub2-16-b (18.2 g, 53.7 mmol), Pd 2 (dba) 3 (1.47 g, 1.61 mmol), P(t-Bu) 3 (0.65 g, 3.22 mmol) and NaOt-Bu (10.3 g, 107 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 14.0 g of the product (yield 74%).

[0248] 4. Synthesis example of Sub2-19

[0249]

[0250] Sub2-19-a (5.0 g, 29.5 mmol) was dissolved in toluene (150 mL), and Sub2-19-b (10.0 g, 29.5 mmol), Pd 2 (dba) 3 (0.81 g, 0.89 mmol), P(t-Bu) 3(0.36 g, 1.77 mmol) and NaOt-Bu (5.7 g, 59.1 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 9.9 g of the product (yield 78%).

[0251] 5. Synthesis example of Sub2-24

[0252]

[0253] Sub2-1-a (5.0 g, 53.7 mmol) was dissolved in toluene (270 mL), and Sub2-24-b (17.4 g, 53.7 mmol), Pd 2 (dba) 3 (1.47 g, 1.61 mmol), P(t-Bu) 3 (0.65 g, 3.22 mmol) and NaOt-Bu (10.3 g, 107 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 12.2 g of the product (yield 68%).

[0254] 6. Synthesis example of Sub2-30

[0255]

[0256] Sub2-19-a (5.0 g, 29.5 mmol) was dissolved in toluene (150 mL), and Sub2-30-b (9.5 g, 29.5 mmol), Pd 2 (dba) 3 (0.81 g, 0.89 mmol), P(t-Bu) 3 (0.36 g, 1.77 mmol) and NaOt-Bu (5.7 g, 59.1 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 8.0 g of the product (yield 66%).

[0257] 7. Synthesis example of Sub2-39

[0258]

[0259] Sub2-1-a (5.0 g, 53.7 mmol) was dissolved in toluene (270 mL), and Sub2-39-b (20.9 g, 53.7 mmol), Pd 2 (dba) 3 (1.47 g, 1.61 mmol), P(t-Bu) 3(0.65 g, 3.22 mmol) and NaOt-Bu (10.3 g, 107 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 14.9 g of the product (yield 69%).

[0260] 8. Synthesis example of Sub2-41

[0261]

[0262] Sub2-1-a (5.0 g, 53.7 mmol) was dissolved in toluene (150 mL), and Sub2-41-b (18.2 g, 53.7 mmol), Pd 2 (dba) 3 (1.47 g, 1.61 mmol), P(t-Bu) 3 (0.65 g, 3.22 mmol) and NaOt-Bu (10.3 g, 107 mmol) were synthesized according to the method of the synthesis example of Sub2-1 to obtain 12.6 g of the product (yield 67%).

[0263] The compound belonging to Sub2 may be the compounds shown below, but is not limited thereto. Table 2 shows the FD-MS data of the compound.

[0264]

[0265]

[0266] [Table 2]

[0267]

[0268]

[0269] III. Synthesis example of final product

[0270] 1. Synthesis Example of P-1

[0271]

[0272] Sub1-1 (5.0 g, 15.2 mmol) was dissolved in toluene (76 mL), and Sub2-1 (5.1 g, 15.2 mmol) and Pd 2 (dba) 3 (0.42 g, 0.45 mmol), P(t-Bu) 3 (0.18 g, 0.91 mmol) and NaOt-Bu (2.9 g, 30.3 mmol) were reacted at 80 °C. After the reaction, CH 2Cl 2 The organic layer was extracted with MgSO 4 After drying, the concentrate was concentrated, and then separated by a silica gel column and recrystallized to obtain 7.4 g (yield 78%) of a product.

[0273] 2. Synthesis Example of P-19

[0274]

[0275] Sub1-5 (5.0 g, 14.5 mmol) was dissolved in toluene (72 mL), and Sub2-19 (6.2 g, 14.5 mmol), Pd 2 (dba) 3 (0.40 g, 0.43 mmol), P(t-Bu) 3 (0.18 g, 0.87 mmol) and NaOt-Bu (2.8 g, 28.9 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 8.0 g of the product (yield 75%).

[0276] 3. Synthesis Example of P-31

[0277]

[0278] Sub1-7 (5.0 g, 14.5 mmol) was dissolved in toluene (72 mL), and Sub2-24 (4.8 g, 14.5 mmol), Pd 2 (dba) 3 (0.40 g, 0.43 mmol), P(t-Bu) 3 (0.18 g, 0.87 mmol) and NaOt-Bu (2.8 g, 28.9 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 6.7 g of the product (yield 72%).

[0279] 4. Synthesis Example of P-38

[0280]

[0281] Sub1-9 (5.0 g, 14.5 mmol) was dissolved in toluene (72 mL), and Sub2-16 (4.8 g, 14.5 mmol), Pd 2 (dba) 3 (0.40 g, 0.43 mmol), P(t-Bu) 3(0.18 g, 0.87 mmol) and NaOt-Bu (2.8 g, 28.9 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 7.2 g of the product (yield 77%).

[0282] 5. Synthesis Example of P-45

[0283]

[0284] Sub1-17 (5.0 g, 15.2 mmol) was dissolved in toluene (76 mL), and Sub2-4 (5.1 g, 15.2 mmol), Pd 2 (dba) 3 (0.42 g, 0.45 mmol), P(t-Bu) 3 (0.18 g, 0.91 mmol) and NaOt-Bu (2.9 g, 30.3 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 7.5 g of the product (yield 79%).

[0285] 6. Synthesis Example of P-66

[0286]

[0287] Sub1-19 (5.0 g, 14.3 mmol) was dissolved in toluene (71 mL), and Sub2-41 (5.0 g, 14.3 mmol), Pd 2 (dba) 3 (0.39 g, 0.43 mmol), P(t-Bu) 3 (0.17 g, 0.86 mmol) and NaOt-Bu (2.7 g, 28.5 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 6.9 g of the product (yield 73%).

[0288] 7. Synthesis Example of P-70

[0289]

[0290] Sub1-20 (5.0 g, 15.2 mmol) was dissolved in toluene (76 mL), and Sub2-4 (5.1 g, 15.2 mmol), Pd 2 (dba) 3 (0.42 g, 0.45 mmol), P(t-Bu) 3(0.18 g, 0.91 mmol) and NaOt-Bu (2.9 g, 30.3 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 7.2 g of the product (yield 76%).

[0291] 8. Synthesis Example of P-106

[0292]

[0293] Sub1-27 (5.0 g, 15.2 mmol) was dissolved in toluene (76 mL), and Sub2-30 (6.2 g, 15.2 mmol), Pd 2 (dba) 3 (0.42 g, 0.45 mmol), P(t-Bu) 3 (0.18 g, 0.91 mmol) and NaOt-Bu (2.9 g, 30.3 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 7.5 g of the product (yield 70%).

[0294] 9. Synthesis Example of P-110

[0295]

[0296] Sub1-6 (5.0 g, 15.2 mmol) was dissolved in toluene (76 mL), and Sub2-39 (6.1 g, 15.2 mmol), Pd 2 (dba) 3 (0.42 g, 0.45 mmol), P(t-Bu) 3 (0.18 g, 0.91 mmol) and NaOt-Bu (2.9 g, 30.3 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 7.2 g of the product (yield 68%).

[0297] 10. Synthesis Example of P-122

[0298]

[0299] Sub1-23 (5.0 g, 12.3 mmol) was dissolved in toluene (62 mL), and Sub2-1 (4.1 g, 12.3 mmol), Pd 2 (dba) 3 (0.34 g, 0.37 mmol), P(t-Bu) 3(0.15 g, 0.74 mmol) and NaOt-Bu (2.4 g, 24.6 mmol) were synthesized according to the method of the synthesis example of P-1 to obtain 6.5 g of the product (yield 75%).

[0300] Table 3 shows the FD-MS data of the compounds P-1 to P-124 of the present invention prepared according to the synthesis examples.

[0301] [Table 3]

[0302]

[0303]

[0304] [Synthesis Example 2] Synthesis Example of Compound 1.N-19 of Chemical Formula 2

[0305]

[0306] 2,4-Di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (5.0 g, 11.9 mmol) and (5-phenyl-2-naphthyl)boronic acid (3.0 g, 11.9 mmol) were dissolved in tetrahydrofuran (THF, 60 mL), and Pd(PPh 3 ) 4 (0.83 g, 0.71 mmol), potassium carbonate (K 2 CO 3 ,4.9g,35.7mmol) and water (30mL), stirred and reacted under reflux. After the reaction, it was extracted with ether and water, the organic layer was concentrated and washed with anhydrous MgSO 4 The residue was dried, concentrated again, purified by silica gel column chromatography, and recrystallized to obtain 5.5 g (yield 78%) of the product.

[0307] 2. Synthesis Example of N-33

[0308]

[0309] 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.7 mmol) was dissolved in tetrahydrofuran (THF, 60 mL), and [2,2'-binaphthyl]-1-ylboronic acid (5.6 g, 18.7 mmol), Pd(PPh 3 ) 4 (1.29 g, 1.12 mmol) and potassium carbonate (K 2 CO 3 ,7.7g,56.0mmol), stirred and reacted under reflux conditions. After the reaction was completed, it was extracted with ether and water, the organic layer was concentrated and washed with anhydrous MgSO4 The product was dried, concentrated again, separated by silica gel column chromatography and recrystallized to obtain 6.4 g of the product (yield 71%).

[0310] Table 4 shows the FD-MS data of compounds 6-1 to 6-124 and compounds N-1 to N-148 of the present invention prepared according to the synthesis examples.

[0311] [Table 4]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317] Manufacturing and evaluation of organic electrical components

[0318] [Example 1] Red organic light emitting element (phosphorescent host)

[0319] A hole injection layer with a thickness of 60 nm was formed on the ITO layer (anode) by vacuum evaporation, and the layer was composed of N1-(2-naphthyl)-N4,N4-bis(4-(2-naphthyl(phenyl)amino)phenyl)-N1-phenyl-1,4-phenylenediamine (hereinafter referred to as "2-TNATA"). Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as "NPD") was vacuum evaporated to a thickness of 50 nm on the hole injection layer to form a hole transport layer.

[0320] Next, tri(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter referred to as “TCTA”) was vacuum-deposited on the hole transport layer to a thickness of 10 nm to form a light-emitting auxiliary layer.

[0321] Subsequently, on the hole transport layer, tri(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter referred to as “TCTA”) was vacuum-deposited to a thickness of 10 nm to form a light-emitting auxiliary layer.

[0322] Subsequently, on the light-emitting auxiliary layer, a mixture of the compound P-1 contained in the chemical formula 1 of the present invention and the compound N-19 contained in the chemical formula 2 in a mass ratio of 5:5 was used as a main material, and bis(1-phenylisoquinolyl)iridium(III)acetylacetone (hereinafter referred to as "(piq) 2Ir(acac)") was used as a dopant so that the mass ratio of the host to the dopant was 95:5, and a light-emitting layer with a thickness of 30 nm was formed by doping.

[0323] Subsequently, (1,1'-biphenyl-4-hydroxy)bis(2-methyl-8-hydroxyquinoline)aluminum was vacuum-deposited on the light-emitting layer to form a hole blocking layer with a thickness of 10 nm. Bis(10-hydroxybenzo[h]quinolinyl)beryllium (hereinafter referred to as "BeBq 2 ”) to form an electron transport layer with a thickness of 45 nm. 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.

[0324] [Example 2] to [Example 26]

[0325] The host material of the light-emitting layer used a mixture of the compound of Chemical Formula 1 of the present invention and Compound N-19 described in the following Table 6 instead of a mixture of Compound P-1 and Compound N-19 of the present invention. In addition, the method in Example 1 was used to manufacture an organic electroluminescent element.

[0326] [Comparative Example 1] and [Comparative Example 2]

[0327] The main material of the light-emitting layer uses a mixture of comparative compound A or comparative compound B and compound N-1 instead of a mixture of compound P-1 and compound N-19 of the present invention. In addition, the method in Example 1 is used to manufacture an organic electroluminescent element.

[0328]

[0329]

[0330] A forward bias DC voltage was applied to the organic light-emitting elements prepared by the embodiments and comparative examples of the present invention, and the electroluminescence (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 5 below.

[0331] [Table 5]

[0332]

[0333]

[0334] As can be seen from Table 5, compared with the use of comparative compound A or comparative compound B, when the compound of the present invention is used as the main material of the light-emitting layer, it can be confirmed that the driving voltage is reduced, and the efficiency and life are significantly improved. As for comparative compound A, the substituent corresponding to the chemical formula A of the present invention is a carbazole group, which is different from the compound of the present invention in which the substituent is dibenzofuran or dibenzothiophene. Due to this difference, compared with the use of comparative compound A, when the compound of the present invention is used as the main body, the characteristics of the element are improved. In view of this, it can be seen that even if it is a compound with a similar skeleton, the type of substituent will affect the characteristics of the element.

[0335] Table 6 below shows the reorganization energy (Reorganization Energy) values ​​of the comparative compound A and the compound P-45 of the present invention, and the RE calculated by the above-described formula: hole value.

[0336] [Table 6]

[0337] Compound Reorganization Energy (RE) Comparative Compound A 0.20 P-45 0.12

[0338] It can be seen from Table 6 that the compound P-45 of the present invention has a lower RE value than the comparative compound A. Therefore, the RE value may be different depending on the substituent type of the amine group. The smaller the RE value, the better the mobility of the hole, and the faster the HOD (Hole Only Device), so when the compound of the present invention is used as the main body, not only the driving voltage can be reduced, but also the efficiency and life can be improved.

[0339] In particular, when a mixture of two or more compounds is used as the main body of the light-emitting layer, the driving voltage, efficiency and life depend on the difficulty of injecting holes and electrons into the dopant. If the appropriate ratio of holes and electrons (charge balance) can be maintained, the efficiency and life will be significantly improved.

[0340] Therefore, it can be seen that when a specific substituent group is substituted on an amine, a positive effect is produced on the overall hole mobility, and since the ratio of holes to electrons, such as energy balance and stability, is improved, the overall performance of the device is improved. In view of this, even within the same skeleton, the RE value will differ depending on the type and substitution position of the substituent group, and the resulting device characteristics will also be different.

[0341] Comparative compound B is different from the compound of the present invention in which dibenzofuran or dibenzothiophene is substituted via a phenylene group in that dibenzofuran is directly substituted on the nitrogen of the amine group.

[0342] Since the characteristics of the element differ depending on the presence or absence of a linker, it is considered that the physical properties of these compounds will change, and therefore the bond dissociation energy (BDE) of the comparative compound B and the compound P-71 of the present invention was measured.

[0343] Table 7 below shows the values ​​of the weakest bond dissociation energy (BDE) of the comparative compound B and the compound P-71 of the present invention measured using molecular simulation (Gaussian09 Rev. C.01, Schrodinger Materials Science Suite 4.1.161).

[0344] The BDE recorded in the following Table 7 is the result of measurement in the oxidation state where electrons are released from the molecule. When electrons are released from the corresponding compound, positive charges are injected into the tertiary amine. That is, when measured in the oxidation state, stability against holes can be confirmed, and the higher the BDE, the higher the stability against holes.

[0345] [Table 7]

[0346] Structure Name Comparative Compound B P-71 BDE(eV) 40.4 43.2

[0347] By observing the above Table 7, it can be confirmed that the BDE value of the compound P-71 of the present invention is high compared to the comparative compound B. In organic electrical devices, the lower the crystallinity of the film, the more amorphous state can be formed. This amorphous state reduces the grain boundary of the crystal grains through isotropic and homogeneous properties, thereby making the mobility of charge and hole faster. However, according to the molecular structure, even in the same amorphous state, the quantum mechanical BDE of the solid phase molecules in the amorphous state will be different due to the interaction between molecules when it is a solid phase. The higher the value, the more the stability of the compound itself will be increased.

[0348] Therefore, when the compound P-71 of the present invention is used as the host of the organic electrical device, the stability of holes transferred from the hole transport layer to the light emitting layer is significantly increased compared to the use of the comparative compound B, thereby improving the life of the device.

[0349] Moreover, in the case of the compound of the present invention, the x value of CIE (color rendering index) is slightly increased compared to the comparative compound. In view of this, when the compound of the present invention is used as a main component, it will affect the color of the device. That is, as shown in the present invention, when phenanthroxazole and phenyl-dibenzofuran are substituted with an amino substituent, the effect is enhanced due to their synergistic effect.

[0350] 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 the following chemical formula 1: in, In the chemical formula 1, X and Y are independently N, O or S, and one of them is N and the other is O or S, Ar 1 and Ar 2 Independently selected from C 6 ~C 60 Aryl; Fluorenyl; C 3 ~C 60 and C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group, A is the chemical formula A, L 1 and L 2 are independently selected from single bonds; C 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group, Z is selected from O or S, R 1 To R 4 , R a independently selected from hydrogen; deuterium; halogen; cyano; nitro; C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 Heterocyclic group; C 3 ~C 60 Aliphatic ring group; C 1 ~C 20 Alkyl; C 2 ~C 20 Alkenyl; C 2 ~C 20 Alkynyl; C 1 ~C 20 Alkoxy; and C 6 ~C 60 The adjacent R 3 Between or adjacent R 4 The groups can combine with each other to form rings. a is an integer from 0 to 7, b and c are each an integer from 0 to 3, d is an integer from 0 to 4, and The aryl group, arylene group, fluorenyl group, fluorenyl group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and adjacent R 3 Between or adjacent R 4 The rings formed by the mutual bonding of the groups can be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

2. The compound according to claim 1, in, The chemical formula 1 is represented by the following chemical formula 1-1 or chemical formula 1-2, In the chemical formula 1-1 and the chemical formula 1-2, X, Y, R 1 , R 2 , R a , L 1 , L 2 ,Ar 1 ,Ar 2 , A, a and b are the same as defined in claim 1.

3. The compound according to claim 1, in, The chemical formula 1 is represented by chemical formula 1-3, <Chemical Formula 1-3> In the chemical formula 1-3, X, Y, R 1 , R 2 , R a , L 1 , L 2 ,Ar 1 ,Ar 2 , A, a and b are the same as defined in claim 1.

4. The compound according to claim 1, wherein the chemical formula A is represented by any one of the following chemical formulas A-1 to A-4, In the chemical formulas A-1 to A-4, Z, R 3 , R 4 , c and d are the same as defined in claim 1.

5. The compound according to claim 1, in, L 1 or L 2 Selected from the group consisting of the following chemical formulas L-1 to L-3, In the chemical formula L-1 to chemical formula L-3, R 5 and R 6 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring, and e is an integer from 0 to 4, and f is an integer from 0 to 6.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following compounds, 7. The compound according to claim 1, in, The reorganization energy of the compound represented by Chemical Formula 1 is 0.10 to 0.

19.

8. An organic electrical element comprising a first electrode, a second electrode and an organic layer located between the first electrode and the second electrode, in, The organic layer comprises the compound according to claim 1.

9. The organic electric element according to claim 8, in, The organic layer comprises a phosphorescent light-emitting layer, wherein the phosphorescent light-emitting layer comprises the compound according to claim 1 and a compound represented by Chemical Formula 2, <Chemical Formula 2> In the chemical formula 2, X 1 To X 3 are independently C(R') or N, and X 1 To X 3 At least one of them is N, L 4 To L 6 are independently selected from single bonds; C 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group, Ar 5 To Ar 7 Independently selected from C 6 ~C 60 Aryl; Fluorenyl; C 3 ~C 60 and a C 2 ~C 60 A group consisting of a heterocyclic group, R' is independently selected from hydrogen; deuterium; halogen; cyano; nitro; C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 Heterocyclic group; C 3 ~C 60 Aliphatic ring group; C 1 ~C 20 Alkyl; C 2 ~C 20 Alkenyl; C 2 ~C 20 Alkynyl; C 1 ~C 20 Alkoxy; and C 6 ~C 60 A group consisting of aryloxy groups, and The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy can be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

10. The organic electric element according to claim 9, in, Ar 5 To Ar 7 At least one of the following is selected from the group consisting of the following chemical formulas Ar-1 to Ar-8, In the chemical formula Ar-1 to chemical formula Ar-8, X 11 and X 12 Independently of each other, N(Ar 11 ), O, S or C (R 17 )(R 18 ), R 11 To R 18 are independently selected from hydrogen; Deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 17 and R 18 Can combine with each other to form a ring, ta, tb, td are each an integer from 0 to 4, tc is an integer from 0 to 6, te is an integer from 0 to 7, and tf is an integer from 0 to 5, and Ar 11 Choose from C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 Heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic cyclic groups.

11. The organic electric element according to claim 9, in, The chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-6, In the chemical formula 2-1 to the chemical formula 2-6, L 4 To L 6 ,Ar 6 and Ar 7 As defined in claim 10, X 11 , X 13 , X 15 and X 21 Independently of each other 11 , O, S or C (R 17 )(R 18 ), X 12 , X 14 and X 16 are independently single bonds, N(Ar 12 ), O, S or C (R 21 )(R 22 ), Ar 11 and Ar 12 Independently selected from C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic ring groups, R 11 To R 18 , R 21 , R 22 are independently selected from hydrogen; Deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 17 and R 18 Can combine with each other to form a ring, R 21 and R 22 can combine with each other to form a ring, and a', d', f' are integers from 0 to 4, b', c', e' are integers from 0 to 3, ta, tb, td are integers from 0 to 4, te is an integer from 0 to 7, and tf is an integer from 0 to 5.

12. The organic electric element according to claim 9, in, The L 4 To L 6 At least one of the following is selected from the group consisting of Chemical Formula b-1 to Chemical Formula b-13, In the chemical formula b-1 to chemical formula b-13, Z 10 S, O, C (R 1 )(R 2 ) or N(R 3 ), Z 49 To Z 51 Independently of each other, C(R 4 ) or N, at least one of which is N, R 19 To R 24 , R 1 To R 4 are independently selected from hydrogen; Deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 30 The aryloxy group, C 6 ~C 30 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 1 and R 2 can combine with each other to form a ring, and a", c", d" and e" are each an integer from 0 to 4, b" is an integer from 0 to 6, f" and g" are each an integer from 0 to 3, h" is an integer from 0 to 2, and i" is an integer from 0 to 3.

13. The organic electric element according to claim 9, wherein the compound represented by Chemical Formula 2 is any one of the following compounds:

14. The organic electric element according to claim 8, in, 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 electrode.

15. The organic electric element according to claim 14, in, The stack further includes a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer.

16. The organic electric element according to claim 15, in, The organic layer further includes a charge generation layer formed between the two or more stacks.

17. The organic electric element according to claim 8, in, The organic electrical element further includes a light efficiency improvement layer formed on a surface of the first electrode or the second electrode that is not in contact with the organic layer.

18. An electronic device, in, include: A display device comprising the organic electric element according to claim 8; as well as A control unit is used to drive the display device.

19. The electronic device according to claim 18, in, 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.

20. A compound, which is obtained by purifying the material of the organic layer after the organic layer is evaporated from the evaporation equipment in the preparation process of an organic electrical element, It is characterized in that The compound is a compound represented by Chemical Formula 1 of claim 1.

21. The compound according to claim 20, It is characterized in that The purity of the compound is above 99.9%.

22. A method for recovering a compound represented by chemical formula 1, in, include: A step of evaporating an organic layer material comprising a compound represented by Chemical Formula 1 of claim 1; A step of recovering the organic layer material attached to the evaporation equipment; and The step of purifying the recovered organic layer material to obtain the compound represented by the chemical formula 1 with a purity of more than 99.9%.

23. The method for recovering the compound represented by Chemical Formula 1 according to claim 22, in, The purification of the recovered organic layer material comprises: a step of recrystallizing the recovered organic layer material using a recrystallization solvent; a step of performing adsorption separation using an adsorbent; and a step of sublimation purification.

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