KR20200145961A - Compound for organic electric element and organic electric device comprising the same - Google Patents

Abstract

Embodiments of the present invention relate to a compound for an organic electric element and an organic electric element using the same, the compound capable of achieving high luminous efficiency, a low driving voltage, high heat resistance, an improved color purity or lifespan. The compound is represented by chemical formula (1).

Description

Compound for organic electric device and organic electric device using the same {COMPOUND FOR ORGANIC ELECTRIC ELEMENT AND ORGANIC ELECTRIC DEVICE COMPRISING THE SAME}

Embodiments of the present invention relate to a compound for an organic electric device and an organic electric device using the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic electric device using an organic light emission phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as an organic material layer in an organic electronic device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

In addition, the light-emitting material can be classified into a high-molecular type and a low-molecular type according to its molecular weight, and according to the light-emitting mechanism, it can be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. I can. In addition, the light-emitting materials may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. A host/dopant system may be used as a light-emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light-emitting layer is mixed in the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is increasing in size as a large-area display. Since the portable display has a battery, which is a limited power supply, more efficient power consumption than the power consumption required in the existing portable display is required. In addition, in addition to efficient power consumption, the problem of luminous efficiency and lifespan must be solved.

Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize efficiency. This is because the long life and high efficiency can be achieved at the same time when the optimum combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) is achieved. Accordingly, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer.

In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials, are stable and efficient. Supported by the material must precede, but the development of a stable and efficient organic material layer material for organic electric devices has not been sufficiently achieved. Accordingly, development of new materials is continuously required, and in particular, development of a host material for a light emitting layer is urgently required.

Embodiments of the present invention can provide a compound capable of improving 　 high heat resistance, color purity, and lifespan while lowering 　 driving voltage of a device, an organic electric device using the same, and an electronic device thereof.

In one aspect, embodiments of the present invention can provide a compound represented by the following formula (1), an organic electric device including the same, and an electronic device thereof.

Formula (1)

According to the embodiments of the present invention, by using the compound according to the embodiments of the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of the device, and the color purity and lifespan of the device are greatly improved. Device can be provided.

1 to 3 are schematic views of organic electric devices according to embodiments of the present invention.

Hereinafter, some embodiments of the present invention will be described in detail with reference to exemplary drawings.

In adding reference numerals to elements of each drawing, the same elements may have the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, when it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof may be omitted. When "include", "have", "consists of" and the like mentioned in the present specification are used, other parts may be added unless "only" is used. In the case of expressing the constituent elements in the singular, the case including plural may be included unless there is a specific explicit description.

In addition, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a) and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, order, or number of the component is not limited by the term.

In the description of the positional relationship of the components, when two or more components are described as being "connected", "coupled" or "connected", the two or more components are directly "connected", "coupled" or "connected" ", but it will be understood that two or more components and other components may be further "interposed" to be "connected", "coupled" or "connected". Here, the other components may be included in one or more of two or more components "connected", "coupled" or "connected" to each other.

In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.

In the description of the temporal flow relationship related to the components, the operation method or the manufacturing method, for example, the temporal predecessor relationship such as "after", "after", "after", "before", etc. Alternatively, a case where a flow forward and backward relationship is described may also include a case that is not continuous unless "direct" or "direct" is used.

On the other hand, when a numerical value for a component or its corresponding information is mentioned, the numerical value or its corresponding information may be caused by various factors (e.g., process factors, internal or external shock, noise, etc.) It can be interpreted as including a possible error range.

The term "halo" or "halogen" as used in the present application includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used in the present application has 1 to 60 carbons connected by a single bond unless otherwise specified, and a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted It may mean a radical of a saturated aliphatic functional group including a cycloalkyl group and a cycloalkyl-substituted alkyl group.

The terms "haloalkyl group" or "halogenalkyl group" as used in the present application may mean an alkyl group in which halogen is substituted unless otherwise specified.

The terms "alkenyl" or "alkynyl" used in the present application each have a double bond or a triple bond, unless otherwise specified, include a straight or branched chain group, and may have 2 to 60 carbon atoms.

The term "cycloalkyl" used in the present application may mean an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified.

The term "alkoxy group" or "alkyloxy group" as used herein refers to an alkyl group to which an oxygen radical is bonded, and may have 1 to 60 carbon atoms unless otherwise specified.

The terms "alkenyl group", "alkenoxy group", "alkenyloxy group", or "alkenyloxy group" as used in the present application mean an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 May have carbon number of.

The terms "aryl group" and "arylene group" as used in the present application each have 6 to 60 carbon atoms, but are not limited thereto. In the present application, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated multiple ring system, a spiro compound, and the like. For example, the aryl group includes, but is limited to, phenyl group, biphenyl, naphthyl, anthryl, indenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. It is not. The naphthyl includes 1-naphthyl and 2-naphthyl, and the anthryl may include 1-anthryl, 2-anthryl, and 9-anthryl.

In the present application, the terms "fluorenyl group" or "fluorenylene group" may each mean a monovalent or divalent functional group of fluorene unless otherwise specified. In addition, the "fluorenyl group" or "fluorenylene group" may mean a substituted fluorenyl group or a substituted fluorenylene group. "Substituted fluorenyl group" or "substituted fluorenylene group" may mean a monovalent or divalent functional group of substituted fluorene. "Substituted fluorene" may mean that at least one of the following substituents R, R', R" and R'" is a functional group other than hydrogen. It may include the case where R and R'are bonded to each other to form a spy compound with the carbon to which they are bonded.

The term "spyro compound" as used in the present application has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It can be called a compound.

The term "heterocyclic group" as used in the present application includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used in the present application represents N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type including a heteroatom, a ring aggregate, a conjugated ring system, spy It may mean a compound or the like.

In addition, the "heterocyclic group" may also include a ring including SO ₂ instead of carbon forming a ring. For example, the "heterocyclic group" may include the following compounds.

The term “ring” used in the present application includes monocyclic and polycyclic rings, and includes a heterocycle including at least one heteroatom as well as a hydrocarbon ring, and may include aromatic and non-aromatic rings.

The term "polycyclic" as used in the present application includes ring assemblies, fused ring systems and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon rings as well as at least one hetero It may contain a heterocycle containing an atom.

The term "aliphatic ring group" used in the present application refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic types, ring aggregates, conjugated ring systems, spiro compounds, etc., unless otherwise stated, It may mean 3 to 60 rings. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.

The term "ring assemblies" as used in this application means that two or more ring systems (single ring or fused ring system) are directly connected to each other through a single bond or a double bond. For example, in the case of an aryl group, it may be a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

The term "conjugated multiple ring systems" as used in the present application refers to a fused ring type that shares at least two atoms. For example, the aryl group may be a naphthalenyl group, a phenanthrenyl group, or a fluorenyl group, but is not limited thereto.

In addition, when the prefixes are named consecutively, it may mean that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonylalkenyl group, it may mean an alkenyl group substituted with an arylcarbonyl group. have. Here, the arylcarbonyl group may be a carbonyl group substituted with an aryl group.

In addition, unless expressly stated, the term "substituted or unsubstituted" used in the present application "substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group of, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a group, a germanium group, and at least one heteroatom selected from the group consisting of O, N, S, Si and P It can be, but is not limited to these substituents.

In the present application, the'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe the'name of the functional group reflecting the number', but it is described as the'parent compound name' You may. For example, in the case of'phenanthrene,' a kind of aryl group, the monovalent'group' is'phenanthryl (group)', and the divalent group is labeled with the name of the group by dividing the valence such as'phenanthrylene (group)'. Although it can be done, it can also be described as'phenanthrene', which is the name of the parent compound regardless of the valence. Similarly, even in the case of pyrimidine, it is described as'pyrimidine' regardless of the valence, or in the case of monovalent, it is described as pyrimidinyl (group), in the case of divalent, the'group' of the corresponding valency, such as pyrimidinylene (group). You can also write it as'name'. Therefore, when the type of the substituent is described as the parent compound name in the present application, it may mean an n-valent'group' formed by desorbing a carbon atom and/or a hydrogen atom bonded to a heteroatom of the parent compound.

In addition, unless there is an explicit description, the formula used in this application may be applied in the same manner as the definition of the substituent 　 in the index definition of the following formula.

Here, when a is 0, the substituent R ¹ means that the substituent R ¹ is absent, which means that all hydrogens are bonded to the carbons that form the benzene ring. Can be described. In addition, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming a benzene ring, and when a is 2 or 3, each can be bonded as follows, and a is 4 to 6 In the case of an integer, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different from each other.

In the present application, that substituents are bonded to each other to form a ring means that adjacent groups are bonded to each other to form a single ring or multiple conjugated rings, and the single ring and the formed conjugated multiple rings are hydrocarbon rings as well as at least one hetero It includes a heterocycle containing an atom, and may include aromatic and non-aromatic rings.

In the present application, the organic electric device may mean a component(s) between an anode and a cathode, or an organic light emitting diode including an anode and a cathode, and component(s) positioned therebetween.

In addition, in some cases, the organic electric device in the present application may refer to an organic light-emitting diode and a panel including the same, or may refer to an electronic device including a panel and a circuit. Here, for example, the electronic device is a display device, a lighting device, a solar cell, a portable or mobile terminal (eg, a smart phone, a tablet, a PDA, an electronic dictionary, a PMP, etc.), a navigation terminal, a game machine, various TVs, and various computers. Any type of device may be included as long as it includes all of the monitors and the like, but is not limited thereto.

Organic Electric Device FIGS. 1 to 3 are exemplary views of organic electric devices according to embodiments of the present invention.

First, referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). An organic material layer including the compound according to the present invention may be included between the and the second electrode 170, and the capping layer 180 may or may not be additionally formed.

The first electrode 110 of FIG. 1 may be an anode (anode), and the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode. .

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

In addition, referring to FIG. 2, the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 220, a hole transport layer 230, and a buffer layer sequentially disposed on the first electrode 210. 243), a light emission auxiliary layer 253, a light emission layer 240, an electron transport layer 250, an electron injection layer 260, and a second electrode 270 may be included, and an additional capping layer 280 may be formed. Yes, it may not be formed.

Meanwhile, although not shown in FIG. 2, an electron transport auxiliary layer may be further disposed between the light emitting layer 240 and the electron transport layer 250.

In addition, referring to FIG. 3, in the organic electric device 300 according to another embodiment of the present invention, a stack of multilayer organic material layers ST1 and ST2 is formed between the first electrode 310 and the second electrode 370. More than one set can be placed. For example, a first stack ST1 is disposed on the first electrode 310, a second stack ST2 is disposed on the first stack ST1, and a second stack ST2 is disposed on the second stack ST2. The electrode 370 may be disposed. A charge generation layer (CGL) may be disposed between the first stack ST1 and the second stack ST2. Additionally, the capping layer 380 may or may not be formed on the second electrode 370.

Specifically, in the present application, the organic electric device 300 includes a first electrode 310, a first stack ST1, a charge generation layer CGL, a second stack ST2, a second electrode 370, and a capping layer. (380) may be included.

The first stack ST1 is an organic material layer formed on the first electrode 310, which is a first hole injection layer 321, a first hole transport layer 331, a first emission layer 341 and a first electron transport layer 351 ), and the second stack ST2 may include a second hole transport layer 332, a second emission layer 342, and a second electron transport layer 352. Additionally, an electron injection layer 360 may be included between the second electrode and the second electron transport layer. As described above, the first stack and the second stack may be organic material layers having the same stacked structure.

The charge generation layer CGL may include a first charge generation layer 390 and a second charge generation layer 391. Since the charge generation layer CGL is disposed between the first and second emission layers 341 and 342, the current efficiency generated in each emission layer may be increased, and electric charges may be smoothly distributed.

The first emission layer 341 may include a light emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 342 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first and second emission layers 341 and 342 according to an embodiment of the present invention is not limited thereto.

The charge generation layer CGL and the second stack ST2 may be repeatedly positioned n times, which is a positive integer. For example, n may be an integer of 1 to 5. For example, when n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.

In the drawing, a capping layer 180 is formed on at least one of one surface of the first electrode 110, 210, and 310 opposite to the organic material layer and one surface of the second electrode 170, 270, 370 opposite to the organic material layer. , 280, 380) may be formed.

In addition, when the capping layer is formed, the light efficiency of the organic electric device may be improved.

In the case of a top emission organic light emitting device, the capping layers 180, 280, 380 play a role in reducing optical energy loss due to surface plasmon polaritons (SPPs) in the second electrodes 170, 270, 370. can do. In the case of a bottom emission organic electric device, the capping layers 180, 280, and 380 may serve as a buffer for the second electrodes 170, 270, and 370.

On the other hand, when a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electric device in which white light is emitted by a mixing effect of light emitted from each light emitting layer.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 220, 321), a hole transport layer (130, 230, 331, 332), a buffer layer (243), a light emission auxiliary layer (253), an electron transport layer (150). , 250, 351, 352), electron injection layers 160, 260, 360, light emitting layers 140, 240, 341, 342, or capping layers 180, 280, 380. For example, the compound of the present invention may be used as a material for the electron transport layers 150, 250, 351, 352, the host of the emission layers 140, 240, 341, 342, and the capping layers 180, 280, 380.

On the other hand, even with the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto may be changed. Research is needed. In particular, long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T1 value between each organic material layer, and intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved.

The organic electric device according to the embodiments of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (Physical Vapor Deposition) or CVD (Chemical Vapor Deposition), for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to deposit the anodes 110, 210, 310), and hole injection layers (120, 220, 321), hole transport layers (130, 230, 331, 332), light emitting layers (140, 240, 341, 342), electron transport layers (150, 250, 351) thereon. After forming an organic material layer including the, 352 and electron injection layers 160, 260, and 360, it may be manufactured by depositing a material that can be used as the cathodes 170, 270, and 370 thereon.

In addition, the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading. It can be manufactured with fewer layers by a method such as a process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and excellent processability, while there is an advantage that can be manufactured using the existing LCD color filter technology. Various structures for white organic electric devices mainly used as backlight devices have been proposed and patented. Typically, R(Red), G(Green), B(Blue) light emitting parts are arranged side-by-side in a mutually planar way, and R, G, B light emitting layers are stacked up and down. In addition, there is a color conversion material (CCM) method that uses electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to such WOLED.

Hereinafter, a compound according to an aspect of the present invention will be described. A compound according to an aspect of the present invention is represented by the following formula (1).

Formula (1)

The substituents and linking groups described in Formula (1) will be described below.

T can be CR'R'', NR''', O or S.

X ¹ and X ² may each independently be selected from the group consisting of CR′R″, NR″′, O and S.

Y ¹ and Y ² may each independently be selected from the group consisting of CR′R″, NR″′, O and S.

Z ¹ and Z ² may each independently be selected from the group consisting of CR′R″, NR″′, O and S.

a to f are each independently 0 or 1, and a+b, c+d, and e+f are 1. For example, when a is 0, it may mean that two carbons indicated as being bonded to X ¹ in Formula (1) are connected by a single bond.

R'and R'' are each independently hydrogen; C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; And O, N, S, Si, and is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom of P, may be bonded to each other to form a spy compound.

For example, R'and R'' are each independently hydrogen; It may be selected from the group consisting of a C ₁ ~ C ₆₀ alkyl group and a C ₆ ~ C ₆₀ aryl group.

When R'or R'' is an alkyl group, for example, each independently may be a C ₁ to C ₅₀ alkyl group, a C ₁ to C ₃₀ alkyl group, a C ₁ to C ₁₀ alkyl group or a methyl group.

When R'or R'' is an aryl group, for example, each independently C ₆ to C ₆₀ aryl group, C ₆ to C ₄₀ aryl group, C ₆ to C ₂₀ aryl group, C ₆ to C ₁₀ It may be an aryl group of or phenyl.

R''' is each independently hydrogen; C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; And O, N, S, Si and P may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

When R''' is an alkyl group, for example, it may be a C ₁ to C ₅₀ alkyl group, a C ₁ to C ₃₀ alkyl group, and a C ₁ to C ₁₀ alkyl group.

When R''' is an aryl group, for example, it may be a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₄₀ aryl group, or a C ₆ ~ C ₂₅ aryl group.

When R''' is a heterocyclic group, for example, it may be a C ₂ ~ C ₆₀ heterocyclic group, a C ₂ ~ C ₄₀ heterocyclic group, or a C ₂ ~ C ₂₀ heterocyclic group.

R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ¹ to R ⁴ may be bonded to each other to form a ring.

For example, R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Alternatively, it may be an alkenyl group of C ₂ to C ₂₀ , and neighboring R ¹ to R ⁴ may be bonded to each other to form a ring.

R ⁵ to R ⁸ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ⁵ to R ⁸ may be bonded to each other to form a ring.

For example, R ⁵ to R ⁸ are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Alternatively, it may be an alkenyl group of C ₂ to C ₂₀ , and neighboring R ⁵ to R ⁸ may be bonded to each other to form a ring.

R ⁹ to R ¹² are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ⁹ to R ¹² may be bonded to each other to form a ring.

For example, R ⁹ to R ¹² are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Alternatively, it may be an alkenyl group of C ₂ to C ₂₀ , and neighboring R ⁹ to R ¹² may be bonded to each other to form a ring.

L'is each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ of the heterocyclic group; may be selected from the group consisting of.

R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And O, N, S, Si, and a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of.

In the above R', R'', R''', R ¹ to R ¹² , L', R _a and R _b , the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group , An alkynyl group, an alkoxyl group, an aryloxy group, an alkylene group, an arylene group, and a fluorenylene group, respectively, deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; An alkoxyl group of C ₁ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of a C ₇ ~ C ₂₀ arylalkyl group and a C ₈ ~ C ₂₀ arylalkenyl group may be further substituted. Therefore, when the R', R'', R''', R ¹ to R ¹² , L', R _a and R _b are understood as primary substituents, the additionally substituted substituents will be understood as secondary substituents. I can.

In addition, the additionally substituted substituents (secondary substituents) may be bonded to each other to form a ring, and the additionally substituted substituents are each deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; An alkoxyl group of C ₁ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And one or more substituents selected from the group consisting of C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring. Accordingly, substituents further substituted on the secondary substituents may be understood as tertiary substituents.

The compound represented by Formula (1) may be represented by any one of Formulas (2) to (9) below.

Formula (2) Formula (3)

Formula (4) Formula (5)

Formula (6) Formula (7)

Formula (8) Formula (9)

In the above formulas (2) to (9), T, X ¹ , X ² , Y ¹ , Y ² , Z ¹ , Z ² and R ¹ to R ¹² are as defined in the formula (1).

Specifically, the compound represented by Formula (1) may be any one of the following compounds, but is not limited thereto.

As another embodiment, the present invention provides an organic electric device including the compound represented by the formula (1).

The organic electric device may include a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, and the organic material layer may include a compound represented by Formula (1).

In another aspect, the organic electric device includes a first electrode, a second electrode, an organic material layer positioned between the first electrode and the second electrode, and one surface of the first electrode opposite to the organic material layer, and the second electrode. A capping layer may be disposed on one or more of one or more of one surface of the organic material layer opposite to the organic material layer, and at least one of the organic material layer and the capping layer may include a compound represented by Formula (1).

The organic material layer and the capping layer may have a single layer or multilayer structure.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and a hole injection layer, a hole transport layer, and a light emission auxiliary included in the organic material layer At least one of a layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injection layer may include a compound represented by Formula (1).

Specifically, at least one of the electron transport auxiliary layer, the electron transport layer and the electron injection layer included in the organic material layer may include a compound represented by Formula (1).

In another embodiment, the compound represented by Formula (1) may be included in at least one emission layer included in the organic material layer.

Embodiments of the present invention provide an organic electric device including one of the compounds represented by formula (1) in the organic material layer, and more specifically, the individual formulas (P-1 to P-173) in the organic material layer. It provides an organic electric device including the compound represented by.

In another embodiment, the compound alone is included in at least one of the hole injection layer, the hole transport layer, the emission auxiliary layer, the emission layer, the electron transport layer, and the electron injection layer of the organic material layer, or the It provides an organic electric device, characterized in that the compound is included in a combination of two or more different compounds, or the compound is included in a combination of two or more different compounds.

In another embodiment, the compound is included alone, the compound is included in a combination of two or more different from each other, or a layer in which the compound is included in a combination of two or more different compounds may be a light emitting layer.

Each of the layers may contain a compound corresponding to formula (1) alone, or a mixture of two or more compounds of formula (1), a compound of formula (1), and a compound not corresponding to the present invention. Mixtures of and may be included. Herein, the compound not applicable to the present invention may be a single compound or two or more compounds.

The compound contained in the organic material layer may be composed of only the same type of compound, but may be a mixture of two or more different types of compounds represented by Formula (1).

For example, in the organic material layer, two types of compounds having different structures among the compounds may be mixed in a molar ratio of 99:1 to 1:99.

Another embodiment of the present invention is an organic layer further comprising a capping layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. Provides electric devices. The capping layer may include the compound represented by Formula (1) according to the present invention.

Organic electricity, characterized in that the compound of the present invention is included in the capping layer alone, the compound of the present invention is included in a combination of two or more different compounds, or the compound of the present invention is included in a combination of two or more different compounds Device.

Another embodiment of the present application provides an organic electric device, characterized in that the compound represented by Formula (1) is mixed in a ratio of 1:9 to 9:1 and used in the emission layer.

Hereinafter, examples for synthesizing the compound represented by Formula (1) according to the present invention and an example for preparing an organic electric device according to the present invention will be described in detail, but the present invention is not limited to the following examples.

[Synthesis Example]

Compounds represented by formula (1) according to the present invention (final products 1 to 28) react with Sub A to H in the (V) method as shown in Schemes 1, 3, 5, 7, 9, 11, 13 and 15 below. It can be manufactured.

(V) The details of the method were described in detail in the section on Scheme 17 to be described later.

1. Manufacturing method according to Scheme 1

<Reaction Scheme 1>

Sub A synthesis example

Sub A of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.

<Reaction Scheme 2>

Synthesis example of Sub A-2

(One) Synthesis of Sub 2-2

Sub 2-1 (50 g, 216.01 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (86.4mL, 216.01 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (73.02g, 648.03 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with MC (methylene chloride), and concentrate. By silicagel column and recrystallization, the product 30.54 g (yield: 72%) was obtained.

(2) Synthesis of Sub 2-4

Sub 2-2 (30 g, 152.75 mmol) and Sub 2-3 (53.33 g, 152.75 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (4.43 g, 2.82 mmol), Potassium carbonate (81.42 g, 589.19 mmol) ), water (150 ml), and THF (tetrahydrofuran) (300 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 42.77 g (yield: 77%) of the product.

(3) Synthesis of Sub A-2

Sub 2-4 (40 g, 110.00 mmol), Sub 2-5 (20.47g, 121.00mmol), Pd ₂ (dba) ₃ (5.03 g, 5.50 mmol) obtained in the above synthesis, t-BuONa (31.71 g, 330.00) mmol), P(t-Bu)3 (4.45 g, 11.00 mmol, Toluene (600 ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ . After concentration, the resulting compound was recrystallized with a silicagel column to obtain 31.87g (yield: 63%) of the product.

Synthesis example of Sub A-14

(One) Synthesis of Sub 14-2

Sub 14-1 (50 g, 201.99 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (80.79mL, 201.99 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (62.96g, 605.97 mmol) was added dropwise over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. A silicagel column and recrystallization gave 28.32 g (yield: 66%) of the product.

(2) Synthesis of Sub 14-4

Sub 14-2 (28 g, 131.79 mmol) and Sub 14-3 (38.16 g, 131.79 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (3.80 g, 3.29 mmol), Potassium carbonate (54.65 g, 395.38 mmol) ), water (140 ml), and THF (tetrahydrofuran) (280 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 37.29 g (yield: 75%) of the product.

(3) Synthesis of Sub A-14

Sub 14-4 (37 g, 98.06 mmol), Pd ₂ (dba) ₃ (2.24 g, 2.45 mmol) obtained in the above synthesis, t-BuONa (28.27 g, 294.19 mmol), P(t-Bu)3 (1.98) g, 4.90 mmol, Toluene (600 ml) was added and stirred at 110 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallization. Thus, the product 18.04g (yield: 54%) was obtained.

2. Manufacturing method according to Scheme 3

<Reaction Scheme 3>

Sub B synthesis example

Sub B of Scheme 3 may be synthesized by the reaction route of Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

Synthesis example of Sub B-30

(One) Synthesis of Sub 30-2

Sub 30-1 (50 g, 140.19 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (56.07mL, 140.19 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (43.70g, 420.58 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. The product 27.04 g (yield: 60%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 30-4

Sub 30-2 (27 g, 83.96 mmol) and Sub 30-3 (35.66 g, 83.96 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.42 g, 2.09 mmol), Potassium carbonate (34.81 g, 251.88 mmol) ), water (140 ml), and THF (tetrahydrofuran) (280 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 32.35 g (yield: 62%) of the product.

(3) Synthesis of Sub B-30

Sub 30-4 (32 g, 51.48 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (1.17 g, 1.28 mmol), t-BuONa (14.84 g, 154.45 mmol), P(t-Bu)3 (1.04 g, 2.57 mmol, Toluene (640 ml) was added and stirred at 110 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column. This gave the product 21.38 g (yield: 71%).

Synthesis example of Sub B-37

(One) Synthesis of Sub 37-2

Sub 37-1 (50 g, 130.65 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (52.26mL, 130.65 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (40.72g, 391.96 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. By silicagel column and recrystallization, the product 29.52 g (yield: 65%) was obtained.

(2) Synthesis of Sub 37-4

Sub 37-2 (29 g, 83.42 mmol) and Sub 37-3 (27.49 g, 83.42 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.41 g, 2.08 mmol), Potassium carbonate (34.58 g, 250.28 mmol) ), water (150 ml), and THF (tetrahydrofuran) (300 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 32.72 g (yield: 71%) of the product.

(3) Synthesis of Sub B-37

Sub 37-4 (32 g, 57.91 mmol), Pd ₂ (dba) ₃ (2.65 g, 2.89 mmol) obtained in the above synthesis, t-BuONa (16.69 g, 173.75 mmol), P(t-Bu)3 (2.34 g, 5.79 mmol, Toluene (600 ml) was added and stirred at 110 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallization. Thus, the product 13.79 g (yield: 49%) was obtained.

3. Manufacturing method according to Scheme 5

<Reaction Scheme 5>

Sub C synthesis example

Sub C of Scheme 5 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.

<Reaction Scheme 6>

Synthesis example of Sub C-42

(One) Synthesis of Sub 42-2

Sub 42-1 (50 g, 194.12 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (77.65mL, 194.12 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (60.51g, 582.38 mmol) was added dropwise over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. The product 31.96 g (yield: 74%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 42-4

Sub 42-2 (31 g, 139.33 mmol) and Sub 42-3 (58.12 g, 139.33 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (4.02 g, 3.48 mmol), Potassium carbonate (57.76 g, 418.01 mmol) ), water (150 ml), and THF (tetrahydrofuran) (300 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 48.78 g (yield: 68%) of the product.

(3) Synthesis of Sub C-42

Sub 42-4 (48 g, 93.22 mmol), Sub 42-5 (14.34 g, 93.22 mmol), Pd ₂ (dba) ₃ (4.26g, 4.66 mmol), t-BuONa (26.87 g, 279.68 mmol) obtained in the above synthesis mmol), P(t-Bu)3 (3.77 g, 9.32 mmol, Toluene (1000 ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ . And after concentration, the resulting compound was recrystallized with a silicagel column to give a product 37.64g (yield: 69%).

Synthesis example of Sub C-51

(One) Synthesis of Sub 51-2

Sub 51-1 (50 g, 126.04 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (50.41 mL, 126.04 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (39.29 g, 378.14 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. A silicagel column and recrystallization gave 28.71 g (yield: 63%) of the product.

(2) Synthesis of Sub 51-4

Sub 51-2 (28 g, 77.43 mmol) and Sub 51-3 (24.44 g, 77.43 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.23 g, 1.76 mmol), Potassium carbonate (32.10 g, 232.30 mmol) ), water (150 ml), and THF (tetrahydrofuran) (300 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 25.67 g (yield: 60%) of the product.

(3) Synthesis of Sub C-51

Sub 51-4 (25 g, 45.24 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (1.03 g, 1.13 mmol), t-BuONa (13.04 g, 135.74 mmol), P(t-Bu)3 (0.91) g, 2.26 mmol, Toluene (600 ml) was added and stirred at 110 °C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallization. Thus, the product 17.98 g (yield: 77%) was obtained.

4. Preparation method according to Scheme 7

<Reaction Scheme 7>

Sub D synthesis example

Sub D of Scheme 7 may be synthesized by the reaction route of Scheme 8 below, but is not limited thereto.

<Reaction Scheme 8>

Synthesis example of Sub D-68

(One) Synthesis of Sub 68-2

Sub 68-1 (50 g, 115.54 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (46.21 mL, 115.54 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (36.01 g, 346.62 mmol) was added dropwise over 30 minutes, followed by stirring at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. A silicagel column and recrystallization gave the product 26.64 g (yield: 58%).

(2) Synthesis of Sub 68-4

Sub 68-2 (26 g, 65.38 mmol) and Sub 68-3 (27.24 g, 65.38 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (1.88 g, 1.63 mmol), Potassium carbonate (27.10 g, 196.14 mmol) ), water (130 ml), and THF (tetrahydrofuran) (260 mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 28.85 g (yield: 64%) of the product.

(3) Synthesis of Sub D-68

Sub 68-4 (28 g, 40.60 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.01 mmol) obtained in the above synthesis, t-BuONa (11.70 g, 121.80 mmol), P(t-Bu)3 (0.82) g, 2.03 mmol, Toluene (600 ml) was added and stirred at 110 °C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallization. Thus, the product 14.54 g (yield: 55%) was obtained.

Synthesis example of Sub D-78

(One) Synthesis of Sub 78-2

Sub 78-1 (50 g, 201.99 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (80.79 mL, 201.99 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (62.96 g, 605.98 mmol) was added dropwise over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. The product was obtained 22.74 g (yield: 53%) by silicagel column and recrystallization.

(2) Synthesis of Sub 78-4

Sub 78-2 (22 g, 103.55 mmol) and Sub 78-3 (48.02 g, 103.55 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.99 g, 2.58 mmol), Potassium carbonate (42.93 g, 310.66 mmol) ), water (110ml), and THF (tetrahydrofuran) (220mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 39.40 g (yield: 69%) of the product.

(3) Synthesis of Sub D-78

Sub 78-4 (39 g, 70.71 mmol), Pd ₂ (dba) ₃ (1.61 g, 1.76 mmol) obtained in the above synthesis, t-BuONa (20.38 g, 212.14 mmol), P(t-Bu)3 (1.43 g, 3.53 mmol, Toluene (780 ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallization. Thus, the product 17.83 g (yield: 52%) was obtained.

5. Preparation method according to Scheme 9

<Reaction Scheme 9>

Sub E synthesis example

Sub E of Scheme 9 may be synthesized by the reaction route of Scheme 10 below, but is not limited thereto.

<Reaction Scheme 10>

Synthesis example of Sub E-81

(One) Synthesis of Sub 81-2

Sub 81-1 (50 g, 140.19 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (56.07 mL, 140.19 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (43.70 g, 420.58 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. Product 33.36 g (yield: 74%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 81-4

Sub 81-2 (33 g, 102.61 mmol) and Sub 81-3 (31.60 g, 102.61 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.96 g, 2.56 mmol), Potassium carbonate (42.54 g, 307.86 mmol) ), water (150ml), THF (tetrahydrofuran) (300mL) was added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 30.56 g (yield: 59%) of the product.

(3) Synthesis of Sub E-81

Sub 81-4 (30 g, 59.42 mmol), Sub 81-5 (5.53 g, 59.42 mmol), Pd ₂ (dba) ₃ (2.70 g, 2.97 mmol), t-BuONa (17.13 g, 178.27 mmol) obtained in the above synthesis mmol), P(t-Bu)3 (2.40 g, 5.94 mmol), Toluene (600 ml) was added and stirred at 110 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 21.84 g (yield: 70%) of the product.

Synthesis example of Sub E-91

(One) Synthesis of Sub 91-2

Sub 91-1 (50 g, 201.99 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (80.79 mL, 201.99 mmol) was slowly added dropwise over 1 hour. At -78℃ for 1 hour after dropwise addition

After stirring, Trimethyl borate (62.96 g, 605.98 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. The product 27.46 g (yield: 64%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 91-4

Sub 91-2 (27 g, 127.08 mmol) and Sub 78-3 (36.80 g, 127.08 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (3.67 g, 3.17 mmol), Potassium carbonate (52.69g, 381.26 mmol) ), water (140ml), and THF (tetrahydrofuran) (280mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 32.60 g (yield: 68%) of the product.

(3) Synthesis of Sub E-91

Sub 91-4 (32 g, 84.81 mmol), Pd ₂ (dba) ₃ (1.94 g, 2.12 mmol) obtained in the above synthesis, t-BuONa (24.45 g, 254.43 mmol), P(t-Bu)3 (1.71) g, 4.24 mmol, Toluene (640ml) was added and stirred at 110 °C. Upon completion of the reaction, the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. Product 16.47 g (yield: 57%) was obtained.

6. Preparation method according to Scheme 11

<Reaction Scheme 11>

Sub F synthesis example

Sub F of Scheme 11 may be synthesized by the reaction route of Scheme 12 below, but is not limited thereto.

<Reaction Scheme 12>

Synthesis example of Sub F-107

(One) Synthesis of Sub 107-2

Sub 107-1 (50 g, 201.99 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (80.79 mL, 201.99 mmol) was slowly added dropwise over 1 hour. At -78℃ for 1 hour after dropwise addition

After stirring, Trimethyl borate (62.96 g, 605.98 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. The product 27.46 g (yield: 64%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 107-4

Sub 107-2 (27 g, 127.08 mmol) and Sub 107-3 (36.80 g, 127.08 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (3.67 g, 3.17 mmol), Potassium carbonate (52.69g, 381.26 mmol) ), water (140ml), and THF (tetrahydrofuran) (280mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 35.00 g (yield: 73%) of the product.

(3) Synthesis of Sub F-107

Sub 107-4 (35 g, 92.76 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.12 g, 2.31 mmol), t-BuONa (26.74 g, 278.29 mmol), P(t-Bu)3 (1.87) g, 4.63 mmol, Toluene (700ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. Product 19.28 g (yield: 61%) was obtained.

Synthesis example of Sub F-118

(One) Synthesis of Sub 118-2

Sub 118-1 (50 g, 194.12mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (77.65 mL, 194.12 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (60.51 g, 582.38 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. Product 33.25 g (yield: 77%) was obtained by silicagel column and recrystallization.

(2) Synthesis of Sub 118-4

Sub 118-2 (33 g, 148.32 mmol) and Sub 118-3 (52.76 g, 148.32 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (4.28, 3.70 mmol), Potassium carbonate (61.49 g, 444.98 mmol) , Water (150ml), THF (tetrahydrofuran) (300mL) was added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 43.04 g (yield: 64%) of the product.

(3) Synthesis of Sub F-118

Sub 118-4 (43 g, 94.82 mmol), Pd ₂ (dba) ₃ (2.17 g, 2.37 mmol) obtained in the above synthesis, t-BuONa (27.33 g, 284.48 mmol), P(t-Bu)3 (1.91) g, 4.74 mmol, Toluene (800ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. Product 22.75 g (yield: 62%) was obtained.

7. Preparation method according to Scheme 13

<Reaction Scheme 13>

Sub G synthesis example

Sub G in Scheme 13 may be synthesized by the reaction route of Scheme 14 below, but is not limited thereto.

<Reaction Scheme 14>

Synthesis example of Sub G-123

(One) Synthesis of Sub 123-2

Sub 81-1 (50 g, 201.99 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (80.79 mL, 201.99 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (62.96 g, 605.98 mmol) was added dropwise over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. A silicagel column and recrystallization gave 21.45 g of the product (yield: 50%).

(2) Synthesis of Sub 123-4

Sub 123-2 (21 g, 98.84 mmol) and Sub 123-3 (28.85 g, 98.84 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.85 g, 2.47 mmol), Potassium carbonate (40.98 g, 296.54 mmol) ), water (100ml), and THF (tetrahydrofuran) (200mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 27.77 g (yield: 74%) of the product.

(3) Synthesis of Sub G-123

Sub 123-4 (27 g, 96.53 mmol), Sub 123-5 (23.96 g, 96.53 mmol), Pd ₂ (dba) ₃ (3.25 g, 3.55 mmol), t-BuONa (20.50 g, 213.33) obtained in the above synthesis mmol), P(t-Bu)3 (2.87 g, 7.11 mmol), Toluene (600 ml) was added and stirred at 110 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 28.02 g (yield: 71%) of the product.

Synthesis example of Sub G-132

(One) Synthesis of Sub 132-2

Sub 132-1 (50 g, 216.01 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (86.40 mL, 216.01 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (67.33 g, 648.03 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. By silicagel column and recrystallization, the product 29.27 g (yield: 69%) was obtained.

(2) Synthesis of Sub 132-4

Sub 132-2 (29 g, 147.66 mmol) and Sub 132-3 (61.82 g, 147.66 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (4.26, 3.69 mmol), Potassium carbonate (61.22 g, 442.99 mmol) , Water (150ml), THF (tetrahydrofuran) (300mL) was added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 48.51 g (yield: 67%) of the product.

(3) Synthesis of Sub G-132

Sub 132-4 (48 g, 97.88 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.24 g, 2.44 mmol), t-BuONa (28.22 g, 293.66 mmol), P(t-Bu)3 (1.98) g, 4.89 mmol, Toluene (1000ml) was added and stirred at 110 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. The product was obtained 23.10 g (yield: 52%).

8. Preparation method according to Scheme 15

<Reaction Scheme 15>

Sub H synthesis example

Sub H of Scheme 15 may be synthesized by the reaction route of Scheme 16 below, but is not limited thereto.

<Reaction Scheme 16>

Synthesis example of Sub H-148

(One) Synthesis of Sub 148-2

Sub 148-1 (50 g, 140.19 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (56.07 mL, 140.19 mmol) was slowly added dropwise over 1 hour. After the dropwise addition, the mixture was stirred at -78°C for 1 hour, then Trimethyl borate (43.70 g, 420.58 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. By silicagel column and recrystallization, the product 30.65 g (yield: 68%) was obtained.

(2) Synthesis of Sub 148-4

Sub 148-2 (30 g, 93.29 mmol) and Sub 148-3 (27.01 g, 93.29 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (2.69 g, 2.33 mmol), Potassium carbonate (38.67 g, 279.87 mmol) ), water (150ml), THF (tetrahydrofuran) (300mL) was added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 34.03 g (yield: 75%) of the product.

(3) Synthesis of Sub H-148

Sub 148-4 (34 g, 69.89 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (1.60 g, 1.74 mmol), t-BuONa (20.15 g, 209.69 mmol), P(t-Bu)3 (1.41) g, 3.49 mmol, Toluene (680ml) was added and stirred at 110 °C. When the reaction was completed, the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. Product 19.81 g (yield: 63%) was obtained.

Synthesis example of Sub H-158

(One) Synthesis of Sub 158-2

Sub 148-1 (50 g, 155.53 mmol) was added to the reactor, dissolved in THF (tetrahydrofuran) (500 ml), and cooled to -78°C.

n-BuLi (86.40 mL, 155.53 mmol) was slowly added dropwise over 1 hour. At -78℃ for 1 hour after dropwise addition

After stirring, Trimethyl borate (67.33 g, 648.03 mmol) was added dropwise for 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. By silicagel column and recrystallization, the product 25.87 g (yield: 61%) was obtained.

(2) Synthesis of Sub 158-4

Sub 158-2 (25 g, 127.29 mmol) and Sub 148-3 (61.20 g, 127.29 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (3.67 g, 3.18 mmol), Potassium carbonate (52.77 g, 381.89 mmol) ), water (125ml), and THF (tetrahydrofuran) (250mL) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 45.01 g (yield: 64%) of the product.

(3) Synthesis of Sub H-158

Sub 148-4 (44 g, 79.63 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (1.82 g, 1.99 mmol), t-BuONa (22.95 g, 238.91 mmol), P(t-Bu)3 (1.61 g, 3.98 mmol, Toluene (680ml) was added and stirred at 110 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column. Product 20.51 g (yield: 53%) was obtained.

Meanwhile, the compounds belonging to Sub A to H may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS values of the compounds belonging to Sub A to H.

compound FD-MS compound FD-MS Sub A-1 m/z=533.17 (C ₃₆ H ₂₄ ClN ₃ =534.06) Sub A-2 m/z=459.10 (C ₃₀ H ₁₈ ClNO ₂ =459.93) Sub A-3 m/z=449.06 (C ₂₈ H ₁₆ ClNOS=449.95) Sub A-4 m/z=505.04 (C ₃₀ H ₁₆ ClNOS ₂ =506.03) Sub A-5 m/z=714.19 (C ₄₉ H ₃₁ ClN ₂ S=715.31) Sub A-6 m/z=383.07 (C ₂₄ H ₁₄ ClNO ₂ =383.83) Sub A-7 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub A-8 m/z=399.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub A-9 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub A-10 m/z=383.07 (C ₂₄ H ₁₄ ClNO ₂ =383.83) Sub A-11 m/z=529.08 (C ₃₀ H ₁₆ ClN ₅ OS=530.00) Sub A-12 m/z=355.96 (C ₁₈ H ₉ ClS ₃ =356.90) Sub A-13 m/z=324.00 (C ₁₈ H ₉ ClO ₂ S=324.78) Sub A-14 m/z=399.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub A-15 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub A-16 m/z=459.14 (C ₃₁ H ₂₂ ClNO=459.97) Sub A-17 m/z=350.05 (C ₂₁ H ₁₅ ClOS=350.86) Sub A-18 m/z=485.15 (C ₃₃ H ₂₄ ClNO=486.01) Sub A-19 m/z=574.18 (C ₃₉ H ₂₇ ClN ₂ O=575.11) Sub A-20 m/z=350.05 (C ₂₁ H ₁₅ ClOS=350.86) Sub B-21 m/z=475.08 (C ₃₀ H ₁₈ ClNOS=475.99) Sub B-22 m/z=515.11 (C ₃₃ H ₂₂ ClNOS=516.06) Sub B-23 m/z=580.15 (C ₃₆ H ₂₅ ClN ₄ S=581.13) Sub B-24 m/z=564.11 (C ₃₆ H ₂₁ ClN ₂ OS=565.09) Sub B-25 m/z=449.06 (C ₂₈ H ₁₆ ClNOS=449.95) Sub B-26 m/z=475.08 (C ₃₀ H ₁₈ ClNOS=475.99) Sub B-27 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub B-28 m/z=360.13 (C ₂₄ H ₂₁ ClO=360.88) Sub B-29 m/z=510.12 (C ₃₂ H ₁₉ ClN ₄ O=510.98) Sub B-30 m/z=584.17 (C ₄₀ H ₂₅ ClN ₂ O=585.10) Sub B-31 m/z=425.10 (C ₂₇ H ₂₀ ClNS=425.97) Sub B-32 m/z=554.10 (C ₃₃ H ₁₉ ClN ₄ OS=555.05) Sub B-33 m/z=555.05 (C ₃₄ H ₁₈ ClNOS ₂ =556.09) Sub B-34 m/z=475.09 (C ₂₉ H ₁₈ ClN ₃ S=475.99) Sub B-35 m/z=532.05 (C ₃₁ H ₁₇ ClN ₂ OS ₂ =533.06) Sub B-36 m/z=350.05 (C ₂₁ H ₁₅ ClOS=350.86) Sub B-37 m/z=485.15 (C ₃₃ H ₂₄ ClNO=486.01) Sub B-38 m/z=484.17 (C ₃₃ H ₂₅ ClN ₂ =485.03) Sub B-39 m/z=366.03 (C ₂₁ H ₁₅ ClS ₂ =366.92) Sub B-40 m/z=458.11 (C ₃₁ H ₁₉ ClO ₂ =458.94) Sub C-41 m/z=521.01 (C ₃₀ H ₁₆ ClNS ₃ =522.10) Sub C-42 m/z=584.20 (C ₄₁ H ₂₉ ClN ₂ =585.15) Sub C-43 m/z=604.11 (C ₃₇ H ₂₁ ClN ₄ OS=605.11) Sub C-44 m/z=574.18 (C ₃₉ H ₂₇ ClN ₂ O=575.11) Sub C-45 m/z=609.20 (C ₄₂ H ₂₈ ClN ₃ =610.16) Sub C-46 m/z=511.11 (C ₃₂ H ₁₈ ClN ₃ O ₂ =511.97) Sub C-47 m/z=308.02 (C ₁₈ H ₉ ClO ₃ =308.72) Sub C-48 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub C-49 m/z=324.00 (C ₁₈ H ₉ ClO ₂ S=324.78) Sub C-50 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub C-51 m/z=515.11 (C ₃₃ H ₂₂ ClNOS=516.06) Sub C-52 m/z=474.10 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub C-53 m/z=681.14 (C ₄₂ H ₂₄ ClN ₅ OS=682.20) Sub C-54 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub C-55 m/z=565.10 (C ₃₅ H ₂₀ ClN ₃ OS=566.08) Sub C-56 m/z=500.14 (C ₃₄ H ₂₅ ClS=501.08) Sub C-57 m/z=551.24 (C ₃₉ H ₃₄ ClN=552.16) Sub C-58 m/z=350.05 (C ₂₁ H ₁₅ ClOS=530.86) Sub C-59 m/z=663.18 (C ₄₆ H ₃₀ ClNS=664.26) Sub C-60 m/z=600.33 (C ₄₁ H ₄₅ ClN ₂ =601.28) Sub D-61 m/z=415.03 (C ₂₄ H ₁₄ ClNS ₂ =415.95) Sub D-62 m/z=485.09 (C ₃₀ H ₁₆ ClN ₃ O ₂ =485.93) Sub D-63 m/z=565.07 (C ₃₆ H ₂₀ ClNS ₂ =566.13) Sub D-64 m/z=660.17 (C ₄₄ H ₂₅ ClN ₄ O=661.16) Sub D-65 m/z=582.15 (C ₄₀ H ₂₃ ClN ₂ O=583.09) Sub D-66 m/z=481.04 (C ₂₈ H ₁₆ ClNOS ₂ =482.01) Sub D-67 m/z=624.08 (C ₃₆ H ₂₁ ClN ₄ OS ₂ =625.16) Sub D-68 m/z=650.15 (C ₄₂ H ₂₃ ClN ₄ O ₂ =651.12) Sub D-69 m/z=401.04 (C ₂₂ H ₁₂ ClN ₃ OS=401.87) Sub D-70 m/z=670.13 (C ₄₀ H ₂₃ ClN ₆ OS=671.18) Sub D-71 m/z=554.11 (C ₃₂ H ₁₉ ClN ₆ S=555.06) Sub D-72 m/z=531.06 (C ₃₁ H ₁₈ ClN ₃ S ₂ =532.08) Sub D-73 m/z=474.08 (C ₃₁ H ₁₉ ClOS=475.00) Sub D-74 m/z=590.16 (C ₃₉ H ₂₇ ClN ₂ S=591.17) Sub D-75 m/z=832.21 (C ₅₆ H ₃₇ ClN ₂ SSi=833.52) Sub D-76 m/z=534.19 (C ₃₇ H ₂₇ ClN ₂ =535.09) Sub D-77 m/z=489.13 (C ₃₂ H ₂₄ ClNS=490.06) Sub D-78 m/z=484.06 (C ₂₆ H ₁₇ ClN ₄ S ₂ =485.02) Sub D-79 m/z=698.21 (C ₄₉ H ₃₁ ClN ₂ O=699.25) Sub D-80 m/z=490.06 (C ₃₁ H ₁₉ ClS ₂ =491.06) Sub E-81 m/z=524.11 (C ₃₄ H ₂₁ ClN ₂ S=525.07) Sub E-82 m/z=613.17 (C ₃₉ H ₂₄ ClN ₅ O=614.11) Sub E-83 m/z=580.08 (C ₃₆ H ₂₁ ClN ₂ S ₂ =581.15) Sub E-84 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub E-85 m/z=491.06 (C ₃₀ H ₁₈ ClNS ₂ =492.05) Sub E-86 m/z=360.13 (C ₂₄ H ₂₁ ClO=360.88) Sub E-87 m/z=450.06 (C ₂₇ H ₁₅ ClN ₂ OS=450.94) Sub E-88 m/z=534.15 (C ₃₆ H ₂₃ ClN ₂ O=535.04) Sub E-89 m/z=449.06 (C ₂₈ H ₁₆ ClNOS=436.93) Sub E-90 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub E-91 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub E-92 m/z=474.10 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub E-93 m/z=324.00 (C ₁₈ H ₉ ClO ₂ S=324.78) Sub E-94 m/z=554.10 (C ₃₃ H ₁₉ ClN ₄ OS=555.05) Sub E-95 m/z=475.08 (C ₃₀ H ₁₈ ClNOS=475.99) Sub E-96 m/z=425.10 (C ₂₇ H ₂₀ ClNS=425.97) Sub E-97 m/z=623.17 (C ₄₃ H ₂₆ ClNO ₂ =624.14) Sub E-98 m/z=490.06 (C ₃₁ H ₁₉ ClS ₂ =491.06) Sub E-99 m/z=350.05 (C ₂₁ H ₁₅ ClOS=350.86) Sub E-100 m/z=484.17 (C ₃₃ H ₂₅ ClN ₂ =485.03) Sub F-101 m/z=415.03 (C ₂₄ H ₁₄ ClNS ₂ =415.95) Sub F-102 m/z=459.10 (C ₃₀ H ₁₈ ClNO ₂ =459.93) Sub F-103 m/z=567.09 (C ₃₆ H ₂₂ ClNS ₂ =568.15) Sub F-104 m/z=463.08 (C ₂₆ H ₁₄ ClN ₅ O ₂ =463.88) Sub F-105 m/z=632.20 (C ₄₅ H ₂₉ ClN ₂ =633.19) Sub F-106 m/z=308.02 (C ₁₈ H ₉ ClO ₃ =308.72) Sub F-107 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub F-108 m/z=499.13 (C ₃₃ H ₂₂ ClNO ₂ =499.99) Sub F-109 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub F-110 m/z=500.09 (C ₃₁ H ₁₇ ClN ₂ O ₃ =500.94) Sub F-111 m/z=474.10 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub F-112 m/z=324.00 (C ₁₈ H ₉ ClO ₂ S=324.78) Sub F-113 m/z=355.96 (C ₁₈ H ₉ ClS ₃ =356.90) Sub F-114 m/z=449.06 (C ₂₈ H ₁₆ ClNOS=449.95) Sub F-115 m/z=505.04 (C ₃₀ H ₁₆ ClNOS ₂ =506.03) Sub F-116 m/z=575.15 (C ₃₉ H ₂₆ ClNS=576.15) Sub F-117 m/z=366.03 (C ₂₁ H ₁₅ ClS ₂ =366.92) Sub F-118 m/z=386.18 (C ₂₇ H ₂₇ Cl=386.96) Sub F-119 m/z=484.17 (C ₃₃ H ₂₅ ClN ₂ =485.03) Sub F-120 m/z=484.16 (C ₃₄ H ₂₅ ClO=485.02) Sub G-121 m/z=473.08 (C ₃₀ H ₁₆ ClNO ₃ =473.91) Sub G-122 m/z=543.06 (C ₃₂ H ₁₈ ClN ₃ S ₂ =544.09) Sub G-123 m/z=554.10 (C ₃₃ H ₁₉ ClN ₄ OS=555.05) Sub G-124 m/z=538.12 (C ₃₃ H ₁₉ ClN ₄ O ₂ =538.99) Sub G-125 m/z=485.19 (C ₃₄ H ₂₈ ClN=486.06) Sub G-126 m/z=486.15 (C ₃₂ H ₂₃ ClN ₂ O=487.00) Sub G-127 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =430.84) Sub G-128 m/z=308.02 (C ₁₈ H ₉ ClO ₃ =308.72) Sub G-129 m/z=485.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub G-130 m/z=534.15 (C ₃₆ H ₂₃ ClN ₂ O=535.04) Sub G-131 m/z=355.96 (C ₁₈ H ₉ ClS ₃ =356.90) Sub G-132 m/z=453.05 (C ₂₄ H ₁₂ ClN ₅ OS=453.90) Sub G-133 m/z=474.10 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub G-134 m/z=376.11 (C ₂₄ H ₂₁ ClS=376.94) Sub G-135 m/z=415.03 (C ₂₄ H ₁₄ ClNS ₂ =415.95) Sub G-136 m/z=350.05 (C ₂₁ H ₁₅ ClOS=350.86) Sub G-137 m/z=590.16 (C ₃₉ H ₂₇ ClN ₂ S=591.17) Sub G-138 m/z=425.10 (C ₂₇ H ₂₀ ClNS=425.97) Sub G-139 m/z=484.16 (C ₃₄ H ₂₅ ClO=485.02) Sub G-140 m/z=708.23 (C ₅₁ H ₃₃ ClN ₂ =709.29) Sub H-141 m/z=533.17 (C ₃₆ H ₂₄ ClN ₃ =534.06) Sub H-142 m/z=429.04 (C ₂₅ H ₁₆ ClNS ₂ =429.98) Sub H-143 m/z=489.06 (C ₃₀ H ₁₆ ClNO ₂ S=489.97) Sub H-144 m/z=572.06 (C ₃₁ H ₁₇ ClN ₆ S ₂ =573.09) Sub H-145 m/z=534.15 (C ₃₆ H ₂₃ ClN ₂ O=535.04) Sub H-146 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub H-147 m/z=324.00 (C ₁₈ H ₉ ClO ₂ S=324.78) Sub H-148 m/z=449.06 (C ₂₈ H ₁₆ ClNOS=449.95) Sub H-149 m/z=475.08 (C ₃₀ H ₁₈ ClNOS=475.99) Sub H-150 m/z=499.13 (C ₃₃ H ₂₂ ClNO ₂ =499.99) Sub H-151 m/z=399.05 (C ₂₄ H ₁₄ ClNOS=399.89) Sub H-152 m/z=533.04 (C ₃₀ H ₁₆ ClN ₃ OS ₂ =534.05) Sub H-153 m/z=655.15 (C ₄₂ H ₂₆ ClN ₃ OS=656.20) Sub H-154 m/z=339.98 (C ₁₈ H ₉ ClOS ₂ =340.84) Sub H-155 m/z=436.99 (C ₂₁ H ₁₂ ClN ₃ S ₃ =437.98) Sub H-156 m/z=425.10 (C ₂₇ H ₂₀ ClNS=425.97) Sub H-157 m/z=366.03 (C ₂₁ H ₁₅ ClS ₂ =366.92) Sub H-158 m/z=485.15 (C ₃₃ H ₂₄ ClNO=486.01) Sub H-159 m/z=484.17 (C ₃₃ H ₂₅ ClN ₂ =485.03) Sub H-160 m/z=509.08 (C ₂₉ H ₂₀ ClN ₃ S ₂ =510.07) Sub H-161 m/z=588.21 (C ₄₀ H ₂₁ D ₅ ClN ₃ =589.15) Sub H-162 m/z=589.09 (C ₃₈ H ₂₀ ClNO ₂ S=590.09) Sub H-163 m/z=424.03 (C ₂₆ H ₁₃ ClO ₂ S=424.90) Sub H-164 m/z=479.10 (C ₃₀ H ₁₄ D ₄ ClNOS=480.01) Sub H-165 m/z=403.07 (C ₂₄ H ₁₀ D ₄ ClNOS=403.92) Sub H-166 m/z=705.16 (C ₄₆ H ₂₈ ClN ₃ OS=706.26) Sub H-167 m/z=525.13 (C ₃₅ H ₂₄ ClNS=526.09) Sub H-168 m/z=534.19 (C ₃₇ H ₂₇ ClN ₂ =535.09)

[Example of final product synthesis]

Sub A to H prepared by Reaction Schemes 1, 3, 5, 7, 9, 11, 13 and 15 can prepare Products 1 to 32 by the reaction route of Scheme 17 and Scheme 18 below, but Products 1 to 32 The manufacturing method of is not limited thereto.

<Scheme 17>

Referring to Scheme 17, it will be possible to understand the method (V) according to the final product to be prepared in Scheme 1.

A specific method of preparing the compound is as follows.

Synthesis example of P-2

(One) Synthesis of Sub A-2-2

Sub A-2 (30 g, 65.22 mmol), THF (tetrahydrofuran) (300 ml), Sub A-2-2 (10.88 g, 65.22 mmol), Pd(PPh ₃ ) ₄ (1.88 g, 1.63 mmol), K ₂ CO ₃ (27.04 g, 195.68 mmol), water (150 ml) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 25.31 g (yield: 71%) of the product.

(2) Synthesis of Sub A-2-3

Sub A-2-2 (25 g, 45.73 mmol) and Triphenylphosphine (35.99 g, 137.21 mmol mol) were added to o- Dichloro-benzene (250 ml) and refluxed for 24 hours. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 12.23 g (yield: 52%) of the product.

(3) Synthesis of P-2

Sub A-2-3 (12 g, 23.31 mmol), Iodobenzene (5.23 g, 25.65 mmol), Pd ₂ (dba) ₃ (0.53 g, 0.58 mmol), NaO t -Bu (6.72 g, 69.95 mmol), P (t-Bu) ₃ (0.47 g, 1.08 mmol) and Toluene (120 mL) were added and stirred at 100°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 9.09 g (yield: 66%) of the product.

Synthesis example of P-14

(1) Synthesis of Sub A-14-2

Sub A-14 (18 g, 52.81 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (180 ml), then Sub A-14-1 (9.50 g, 52.81 mmol), Pd(PPh ₃ ) ₄ (1.52 g, 1.32 mmol), K ₂ CO ₃ (21.89 g, 158.43 mmol), water (90 ml) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 18.37 g (yield: 79%) of the product.

(2) Synthesis of P-14

Sub A-14-2 (18 g, 40.85 mmol) obtained in the above synthesis was put into a reactor and dissolved in THF (tetrahydrofuran) (180 ml), and then methylmagnesium bromide 1.0M in THF (tetrahydrofuran) (122.57 ml, 122.57 mmol) was added. After slowly adding dropwise, the mixture was stirred at room temperature. When the reaction was completed, extraction was performed with diethyl ether and water, and the organic layer was dried over MgSO ₄ and concentrated to obtain an intermediate product. This intermediate product was dissolved in acetic acid solution (60 ml), HCl (3 ml) was added, and the mixture was refluxed. When the reaction was completed, water was added thereto, and the resulting solid was filtered under reduced pressure and then washed with water and methanol to obtain 8.11 g (yield: 47%) of the product as a white powder.

Synthesis example of P-42

(1) Synthesis of Sub C-42-2

Sub C-42 (37 g, 63.23 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (370 ml), and then Sub C-42-1 (8.72 g, 63.23 mmol), Pd(PPh ₃ ) ₄ (1.82) g, 1.58 mmol), K ₂ CO ₃ (26.21 g, 189.69 mmol), water (185 ml) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 28.45 g (yield: 70%) of the product.

(2) Synthesis of P-42

Sub C-42-2 (28 g, 43.55 mmol) obtained in the above synthesis was added to a reactor, and Pd(OAc) ₂ (0.48 g, 2.17 mmol), 3-nitropyridine (0.27 g, 2.17 mmol) were added together and C ₆ After dissolving with F ₆ (112 ml) and DMI (56 ml), tert- butyl peroxybenzoate (16.92g, 87.11 mmol) was added and stirred at 90°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 12.00 g (yield: 43%) of the product.

Synthesis example of P-123

(1) Synthesis of Sub G-123-2

Sub G-123 (28 g, 50.44 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (280 ml), and then Sub G-123-1 (8.47 g, 50.44 mmol), Pd(PPh ₃ ) ₄ (1.47 g) , 1.26 mmol), K ₂ CO ₃ (20.91 g, 151.33 mmol), water (140 ml) were added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 22.05 g (yield: 68%) of the product.

(2) Synthesis of Sub G-123-3

Sub G-123-2 (22 g, 34.22 mmol) and AcOH (110 ml) were added, and H ₂ O ₂ (2.94 mL, 34.22 mmol) was added, followed by reaction at an internal temperature of 30 °C for 24 hours. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 18.26 g (yield: 81%) of the product.

(3) Synthesis of P-123

Sub G-123-3 (18 g, 27.32 mmol) obtained in the above synthesis was added to an excess of Trifluoromethanesulfonic acid, stirred at room temperature for 24 hours, and then water and Pyridine (8:1) were slowly added and stirred. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 7.52 g (yield: 44%) of the product.

<Reaction Scheme 18>

Synthesis example of P-30

(One) Synthesis of Sub B-30-2

Sub B-30 (21 g, 35.89 mmol), THF (tetrahydrofuran) (210 ml), Sub B-30-1 (5.99 g, 35.89 mmol), Pd(PPh ₃ ) ₄ (1.03 g, 0.89 mmol), K ₂ CO ₃ (14.88 g, 107.67 mmol) and water (105 ml) were added, and 16.63 g (yield: 69%) of the product was obtained using the above P-2 synthesis method.

(2) Synthesis of Sub B-30-3

Sub B-30-2 (16 g, 23.81 mmol) and Triphenylphosphine (18.74 g, 71.45 mmol mol) were added to o- Dichloro-benzene (160 ml), and the product 9.44 g (yield) was added using the P-2 synthesis method. : 62%) was obtained.

(3) Synthesis of P-30

Sub B-30-3 (9 g, 14.06 mmol), Iodobenzene (3.44 g, 16.88 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.35 mmol), NaO t -Bu (4.05 g, 42.20 mmol), P (t-Bu) ₃ (0.28 g, 0.70 mmol) and Toluene (90 mL) were added, and 8.86 g (yield: 88%) of the product was obtained using the above P-2 synthesis method.

Synthesis example of P-107

(1) Synthesis of Sub F-107-2

Sub F-107 (19 g, 55.74 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (190 ml), and then Sub F-107-1 (9.34 g, 55.74 mmol), Pd(PPh ₃ ) ₄ (1.61 g) , 1.39 mmol), K ₂ CO ₃ (23.11 g, 167.23 mmol), and water (95 ml) were added, and 19.83 g (yield: 85%) of the product was obtained using the above synthesis method of P-123.

(2) Synthesis of Sub F-107-3

Sub F-107-2 (19 g, 44.33 mmol) and AcOH (95 ml) were added, H ₂ O ₂ (3.81 mL, 44.33 mmol) was added, and the product 12.61 g (12.61 g) was added using the P-123 synthesis method above. Yield: 64%).

(3) Synthesis of P-107

Sub F-107-3 (12 g, 26.99 mmol) obtained in the above synthesis was added to an excess of Trifluoromethanesulfonic acid, stirred at room temperature for 24 hours, and then water and Pyridine (8:1) were slowly added to the P-123 synthesis method. Product 7.23 g (yield: 65%) was obtained.

Synthesis example of P-148

(1) Synthesis of Sub H-148-2

Sub H-148 (19 g, 42.22 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (190 ml), and then Sub H-148-1 (5.82 g, 42.22 mmol), Pd(PPh ₃ ) ₄ (1.21 g, 1.05 mmol), K ₂ CO ₃ (17.50 g, 126.68 mmol), and water (95 ml) were added, and 15.86 g (yield: 74%) of the product was obtained using the P-42 synthesis method.

(2) Synthesis of P-148

Sub H-148-2 (15 g, 29.55 mmol) obtained in the above synthesis was added to a reactor, and Pd(OAc) ₂ (0.33 g, 1.47 mmol), 3-nitropyridine (0.18 g, 1.47 mmol) were added together and C ₆ After dissolving with F ₆ (60 ml) and DMI (30 ml), tert- butyl peroxybenzoate (11.47 g, 59.10 mmol) was added, and 10.15 g (yield: 68%) of the product was obtained using the P-42 synthesis method. .

Synthesis example of P-158

(1) Synthesis of Sub H-158-2

Sub H-158 (20 g, 41.15 mmol) was added to the reactor and dissolved in THF (tetrahydrofuran) (200 ml), then Sub H-158-1 (7.40 g, 41.15 mmol), Pd(PPh ₃ ) ₄ (1.18) g, 1.02 mmol), K ₂ CO ₃ (17.06 g, 123.45 mmol), and water (100 ml) were added, and 11.81 g (yield: 49%) of the product was obtained using the P-14 synthesis method.

(2) Synthesis of P-158

Sub H-158-2 (11 g, 18.78 mmol) obtained in the above synthesis was put into a reactor and dissolved in THF (tetrahydrofuran) (110 ml), and then methylmagnesium bromide 1.0M in THF (tetrahydrofuran) (56.34 ml, 56.34 mmol) was added. After slowly adding dropwise, the mixture was stirred at room temperature. When the reaction was completed, the mixture was extracted with diethyl ether and water, and the organic layer was dried over MgSO ₄ and concentrated to obtain an intermediate product. This intermediate product was dissolved in acetic acid solution (50 ml), HCl (2.5 ml) was added, and the mixture was refluxed. When the reaction was completed, water was added thereto, and the resulting solid was filtered under reduced pressure and washed with water and methanol after stirring to obtain 7.78 g (yield: 73%) of a product as a white powder.

Meanwhile, the FD-MS values of the compounds P-1 to P-173 of the present invention prepared according to the synthesis example as described above are shown in Table 2 below.

compound FD-MS compound FD-MS P-1 m/z=740.29 (C ₅₄ H ₃₆ N ₄ =740.91) P-2 m/z=590.20 (C ₄₂ H ₂₆ N ₂ O ₂ =590.68) P-3 m/z=521.09 (C ₃₄ H ₁₉ NOS ₂ =521.65) P-4 m/z=561.09 (C ₃₆ H ₁₉ NO ₂ OS ₂ =561.67) P-5 m/z=770.24 (C ₅₅ H ₃₄ N ₂ OS=770.95) P-6 m/z=669.22 (C ₄₅ H ₂₇ N ₅ O ₂ =669.74) P-7 m/z=658.18 (C ₄₄ H ₂₆ N ₄ OS=658.78) P-8 m/z=587.14 (C ₃₉ H ₂₅ NOS ₂ =587.76) P-9 m/z=620.16 (C ₄₂ H ₂₄ N ₂ O ₂ S=620.73) P-10 m/z=516.16 (C ₃₄ H ₂₀ N ₄ O ₂ =516.56) P-11 m/z=585.13 (C ₃₆ H ₁₉ N ₅ O ₂ S=585.64) P-12 m/z=412.01 (C ₂₄ H ₁₂ OS ₃ =412.54) P-13 m/z=620.16 (C ₄₂ H ₂₄ N ₂ O ₂ S=620.73 P-14 m/z=422.08 (C ₂₇ H ₁₈ OS ₂ =422.56) P-15 m/z=546.11 (C ₃₇ H ₂₂ OS ₂ =546.70) P-16 m/z=666.27 (C ₄₉ H ₃₄ N ₂ O=666.82) P-17 m/z=406.10 (C ₂₇ H ₁₈ O ₂ S=406.50) P-18 m/z=567.26 (C ₄₂ H ₃₃ NO=567.73) P-19 m/z=646.21 (C ₄₅ H ₃₀ N ₂ OS=646.81) P-20 m/z=406.10 (C ₂₇ H ₁₈ O ₂ S=406.50) P-21 m/z=606.18 (C ₄₂ H ₂₆ N ₂ OS=606.74) P-22 m/z=571.16 (C ₃₉ H ₂₅ NO ₂ S=571.69) P-23 m/z=711.25 (C ₄₈ H ₃₃ N ₅ S=711.89) P-24 m/z=636.13 (C ₄₂ H ₂₄ N ₂ OS ₂ =636.79) P-25 m/z=580.16 (C ₄₀ H ₂₄ N ₂ OS=580.71) P-26 m/z=531.13 (C ₃₆ H ₂₁ NO ₂ S=531.63) P-27 m/z=471.08 (C ₃₀ H ₁₇ NOS ₂ =471.59) P-28 m/z=442.23 (C ₃₃ H ₃₀ O=442.60) P-29 m/z=582.15 (C ₃₈ H ₂₂ N ₄ OS=582.68) P-30 m/z=715.26 (C ₅₂ H ₃₃ N ₃ O=715.86 P-31 m/z=507.20 (C ₃₆ H ₂₉ NS=507.70) P-32 m/z=685.19 (C ₄₅ H ₂₇ N ₅ OS=685.81) P-33 m/z=611.10 (C ₄₀ H ₂₁ NO ₂ S ₂ =611.73) P-34 m/z=531.14 (C ₃₅ H ₂₁ N ₃ OS=531.63) P-35 m/z=588.10 (C ₃₇ H ₂₀ N ₂ O ₂ S ₂ =588.70) P-36 m/z=406.10 (C ₂₇ H ₁₈ O ₂ S=406.50) P-37 m/z=557.18 (C ₃₉ H ₂₇ NOS=557.71) P-38 m/z=615.27 (C ₄₅ H ₃₃ N ₃ =615.78) P-39 m/z=438.06 (C ₂₇ H ₁₈ S ₃ =438.62) P-40 m/z=514.16 (C ₃₇ H ₂₂ O ₃ =514.58) P-41 m/z=652.11 (C ₄₂ H ₂₄ N ₂ S ₃ =652.85) P-42 m/z=640.25 (C ₄₇ H ₃₂ N ₂ O=640.79) P-43 m/z=660.16 (C ₄₃ H ₂₄ N ₄ O ₂ S=660.75) P-44 m/z=646.21 (C ₄₅ H ₃₀ N ₂ OS=646.81) P-45 m/z=740.29 (C ₅₄ H ₃₆ N ₄ =740.91) P-46 m/z=583.14 (C ₃₈ H ₂₁ N ₃ O ₂ S=583.67) P-47 m/z=569.15 (C ₃₆ H ₁₉ N ₅ O ₃ =569.58) P-48 m/z=626.12 (C ₃₉ H ₂₂ N ₄ OS ₂ =626.75) P-49 m/z=396.03 (C ₂₄ H ₁₂ O ₂ S ₂ =396.48) P-50 m/z=606.18 (C ₄₂ H ₂₆ N ₂ OS=606.74) P-51 m/z=571.16 (C ₃₉ H ₂₅ NO ₂ S=571.69) P-52 m/z=605.19 (C ₄₂ H ₂₇ N ₃ S=605.76) P-53 m/z=737.19 (C ₄₈ H ₂₇ N ₅ O ₂ S=737.84) P-54 m/z=646.21 (C ₄₅ H ₃₀ N ₂ OS=646.81) P-55 m/z=647.20 (C ₄₄ H ₂₉ N ₃ OS=647.80) P-56 m/z=572.16 (C ₄₀ H ₂₈ S ₂ =572.78 P-57 m/z=798.40 (C ₆₀ H ₅₀ N ₂ =799.07) P-58 m/z=557.18 (C ₃₉ H ₂₇ NOS=557.71) P-59 m/z=719.23 (C ₅₂ H ₃₃ NOS=719.90) P-60 m/z=789.50 (C ₅₇ H ₆₃ N ₃ =790.15) P-61 m/z=546.12 (C ₃₆ H ₂₂ N ₂ S ₂ =546.71) P-62 m/z=541.14 (C ₃₆ H ₁₉ N ₃ O ₃ =541.57) P-63 m/z=696.17 (C ₄₈ H ₂₈ N ₂ S ₂ =696.89) P-64 m/z=732.20 (C ₅₀ H ₂₈ N ₄ OS=732.86) P-65 m/z=638.20 (C ₄₆ H ₂₆ N ₂ O ₂ =638.73) P-66 m/z=612.13 (C ₄₀ H ₂₄ N ₂ OS ₂ =612.77) P-67 m/z=706.19 (C ₄₅ H ₃₀ N ₄ OS ₂ =706.88) P-68 m/z=732.25 (C ₅₁ H ₃₂ N ₄ O ₂ =732.84) P-69 m/z=608.17 (C ₄₀ H ₂₄ N ₄ OS=608.72) P-70 m/z=742.16 (C ₄₆ H ₂₆ N ₆ OS ₂ =742.88) P-71 m/z=610.16 (C ₃₈ H ₂₂ N ₆ OS=610.70) P-72 m/z=662.16 (C ₄₃ H ₂₆ N ₄ S ₂ =662.83) P-73 m/z=530.13 (C ₃₇ H ₂₂ O ₂ S=530.64) P-74 m/z=672.26 (C ₄₈ H ₃₆ N ₂ S=672.89) P-75 m/z=888.26 (C ₆₂ H ₄₀ N ₂ OSSi=889.16) P-76 m/z=741.31 (C ₅₅ H ₃₉ N ₃ =741.94) P-77 m/z=543.20 (C ₃₉ H ₂₉ NS=543.73) P-78 m/z=556.09 (C ₃₂ H ₂₀ N ₄ S ₂ =556.72) P-79 m/z=754.26 (C ₅₅ H ₃₄ N ₂ O ₂ =754.89) P-80 m/z=703.15 (C ₄₇ H ₂₉ NS ₃ =703.94) P-81 m/z=705.22 (C ₅₀ H ₃₁ N ₃ S=705.88) P-82 m/z=685.19 (C ₄₅ H ₂₇ N ₅ OS=685.81) P-83 m/z=652.11 (C ₄₂ H ₂₄ N ₂ S ₃ =652.85) P-84 m/z=608.17 (C ₄₀ H ₂₄ N ₄ OS=608.72) P-85 m/z=563.08 (C ₃₆ H ₂₁ NS ₃ =563..75) P-86 m/z=646.27 (C ₄₅ H ₃₄ N ₄ O=646.79) P-87 m/z=506.11 (C ₃₃ H ₁₈ N ₂ O ₂ S=506.58) P-88 m/z=769.26 (C ₅₂ H ₃₁ N ₇ O=769.87) P-89 m/z=531.17 (C ₃₇ H ₂₅ NOS=531.67) P-90 m/z=528.04 (C ₃₁ H ₁₆ N ₂ OS ₃ =528.66) P-91 m/z=512.07 (C ₃₁ H ₁₆ N ₂ O ₂ S ₂ =512.60) P-92 m/z=721.23 (C ₄₉ H ₃₁ N ₅ S=721.88) P-93 m/z=380.05 (C ₂₄ H ₁₂ O ₃ S=380.42) P-94 m/z=610.15 (C ₃₉ H ₂₂ N ₄ O ₂ S=610.69) P-95 m/z=684.20 (C ₄₆ H ₂₈ N ₄ OS=684.82) P-96 m/z=662.19 (C ₄₅ H ₃₀ N ₂ S ₂ =662.87) P-97 m/z=679.21 (C ₄₉ H ₂₉ NO ₃ =679.78) P-98 m/z=562.09 (C ₃₇ H ₂₂ S ₃ =562.76) P-99 m/z=531.17 (C ₃₇ H ₂₅ NOS=531.67) P-100 m/z=617.26 (C ₄₃ H ₃₁ N ₅ =617.75) P-101 m/z=622.15 (C ₄₂ H ₂₆ N ₂ S ₂ =622.80) P-102 m/z=590.20 (C ₄₂ H ₂₆ N ₂ O ₂ =590.68) P-103 m/z=698.19 (C ₄₈ H ₃₀ N ₂ S ₂ =698.90) P-104 m/z=519.13 (C ₃₂ H ₁₇ N ₅ O ₃ =519.52) P-105 m/z=851.33 (C ₆₄ H ₄₁ N ₃ =852.05) P-106 m/z=364.07 (C ₂₄ H ₁₂ O ₄ =364.36) P-107 m/z=412.01 (C ₂₄ H ₁₂ OS ₃ =412.54) P-108 m/z=630.23 (C ₄₅ H ₃₀ N ₂ O ₂ =630.75) P-109 m/z=528.04 (C ₃₁ H ₁₆ N ₂ OS ₃ =528.66) P-110 m/z=556.14 (C ₃₇ H ₂₀ N ₂ O ₄ =556.58) P-111 m/z=711.18 (C ₄₈ H ₂₉ N ₃ S ₂ =711.90) P-112 m/z=505.11 (C ₃₄ H ₁₉ NO ₂ S=505.59) P-113 m/z=680.12 (C ₄₂ H ₂₄ N ₄ S ₃ =680.86) P-114 m/z=505.11 (C ₃₄ H ₁₉ NO ₂ S=505.59) P-115 m/z=577.06 (C ₃₆ H ₁₉ NOS ₃ =577.73) P-116 m/z=647.17 (C ₄₅ H ₂₉ NS ₂ =647.85) P-117 m/z=662.12 (C ₄₀ H ₂₆ N ₂ O ₂ S ₃ =662.84) P-118 m/z=468.28 (C ₃₆ H ₃₆ =468.68) P-119 m/z=615.27 (C ₄₅ H ₃₃ N ₃ =615.78) P-120 m/z=615.26 (C ₄₆ H ₃₃ NO=615.78) P-121 m/z=529.13 (C ₃₆ H ₁₉ NO ₄ =529.55) P-122 m/z=615.09 (C ₃₈ H ₂₁ N ₃ S ₃ =615.79) P-123 m/z=626.12 (C ₃₉ H ₂₂ N ₄ OS ₂ =626.75) P-124 m/z=594.17 (C ₃₉ H ₂₂ N ₄ O ₃ =594.63) P-125 m/z=541.24 (C ₄₀ H ₃₁ NO=541.69) P-126 m/z=717.28 (C ₅₂ H ₃₅ N ₃ O=717.87) P-127 m/z=412.01 (C ₂₄ H ₁₂ OS ₃ =412.54) P-128 m/z=364.07 (C ₂₄ H ₁₂ O ₄ =364.36) P-129 m/z=589.22 (C ₄₂ H ₂₇ N ₃ O=589.70) P-130 m/z=667.24 (C ₄₆ H ₂₉ N ₅ O=667.77) P-131 m/z=720.12 (C ₄₃ H ₂₄ N ₆ S ₃ =720.89) P-132 m/z=509.09 (C ₃₀ H ₁₅ N ₅ O ₂ S=509.54) P-133 m/z=605.19 (C ₄₂ H ₂₄ N ₃ S=605.76) P-134 m/z=458.21 (C ₃₃ H ₃₀ S=458.66) P-135 m/z=621.16 (C ₄₃ H ₂₇ NS ₂ =621.82) P-136 m/z=422.08 (C ₂₇ H ₁₈ OS=422.56) P-137 m/z=646.21 (C ₄₅ H ₃₀ N ₂ OS=646.81) P-138 m/z=632.23 (C ₄₅ H ₃₂ N ₂ S=632.83) P-139 m/z=540.21 (C ₄₀ H ₂₈ O ₂ =540.66) P-140 m/z=780.26 (C ₅₇ H ₃₆ N ₂ S=780.99) P-141 m/z=664.26 (C ₄₈ H ₃₂ N ₄ =664.81) P-142 m/z=574.15 (C ₃₈ H ₂₆ N ₂ S ₂ =574.76) P-143 m/z=545.11 (C ₃₆ H ₁₉ NO ₃ S=545.61) P-144 m/z=644.09 (C ₃₇ H ₂₀ N ₆ S ₃ =644.79) P-145 m/z=606.18 (C ₄₂ H ₂₆ N ₂ OS=606.74) P-146 m/z=589.22 (C ₄₂ H ₂₇ N ₃ O=589.70) P-147 m/z=396.03 (C ₂₄ H ₁₂ O ₂ S ₂ =396.48) P-148 m/z=505.11 (C ₃₄ H ₁₉ NO ₂ S=505.59) P-149 m/z=606.18 (C ₄₂ H ₂₆ N ₂ OS=606.74) P-150 m/z=571.16 (C ₃₉ H ₂₅ NO ₂ S=571.69) P-151 m/z=530.15 (C ₃₆ H ₂₂ N ₂ OS=530.65) P-152 m/z=605.07 (C ₃₆ H ₁₉ N ₃ OS ₃ =605.75) P-153 m/z=727.18 (C ₄₈ H ₂₉ N ₃ OS ₂ =727.90) P-154 m/z=571.08 (C ₃₃ H ₂₁ N ₃ OS ₃ =571.73) P-155 m/z=509.01 (C ₂₇ H ₁₅ N ₃ S ₄ =509.68 P-156 m/z=556.20 (C ₃₉ H ₂₈ N ₂ S=556.73) P-157 m/z=668.07 (C ₃₄ H ₂₀ N ₈ S ₄ =668.83) P-158 m/z=567.26 (C ₄₂ H ₃₃ NO=567.73) P-159 m/z=615.27 (C ₄₅ H ₃₃ N ₃ =615.78) P-160 m/z=581.11 (C ₃₅ H ₂₃ N ₃ S ₃ =581.77) P-161 m/z=719.31 (C ₅₂ H ₂₉ D ₅ N ₄ =719.90) P-162 m/z=645.14 (C ₄₄ H ₂₃ NO ₃ S=645.73) P-163 m/z=546.07 (C ₃₆ H ₁₈ O ₂ S ₂ =546.66) P-164 m/z=614.23 (C ₄₂ H ₁₈ D ₈ N ₂ OS=614.79) P-165 m/z=539.20 (C ₃₆ H ₁₃ D ₉ N ₂ OS=539.70) P-166 m/z=781.22 (C ₅₂ H ₂₇ D ₄ N ₃ OS ₂ =781.98) P-167 m/z=706.24 (C ₅₁ H ₃₄ N ₂ S=706.91) P-168 m/z=669.31 (C ₄₉ H ₃₁ D ₄ N ₃ =669.86)

Manufacturing evaluation of organic electric devices

Example) Fabrication and test of red organic light emitting device

First, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl as a hole injection layer on the ITO layer (anode) formed on the glass substrate. )-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[ N- (1-naphthyl) -N -phenylamino]biphenyl (hereinafter abbreviated as -NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. The above invention compound represented by formula (1) was used as a host on the hole transport layer, and as a dopant, (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(²)acetylacetonate] was 95:5 by weight. By doping, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and the electron transport layer As a result, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, as an electron injection layer, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic electroluminescent device.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices of the Examples and Comparative Examples thus prepared. The T95 life was measured through a life measurement equipment manufactured by McScience. Table 3 below shows the results of device fabrication and evaluation.

[Comparative Examples 1, 2, 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds A, B, and C were used as hosts.

Comparative compound A Comparative compound B Comparative compound C

compound Driving
Voltage electric current
(mA/cm2) Luminance
(cd/m2) efficiency
(cd/A) T(95) CIE x y Comparative Example (1) Comparative compound (A) 7.0 21.2 2500.0 11.8 80.7 0.62 0.34 Comparative Example (2) Comparative compound (B) 7.2 21.7 2500.0 11.5 88.2 0.63 0.35 Comparative Example (3) Comparative compound (C) 7.3 21.9 2500.0 11.4 80.1 0.63 0.31 Example (1) P-1 6.2 11.2 2500.0 22.2 109.0 0.65 0.31 Example (2) P-6 6.1 12.9 2500.0 19.3 114.4 0.61 0.34 Example (3) P-11 5.8 13.7 2500.0 18.2 105.6 0.64 0.31 Example (4) P-16 6.4 11.9 2500.0 20.9 108.3 0.64 0.33 Example (5) P-17 6.3 12.1 2500.0 20.7 107.8 0.63 0.33 Example (6) P-23 6.2 11.3 2500.0 22.0 109.0 0.62 0.33 Example (7) P-26 6.1 13.1 2500.0 19.0 114.1 0.63 0.33 Example (8) P-32 5.8 13.2 2500.0 18.9 105.8 0.63 0.32 Example (9) P-33 5.8 13.4 2500.0 18.6 106.5 0.61 0.35 Example (10) P-40 6.3 12.0 2500.0 20.8 108.8 0.64 0.35 Example (11) P-42 6.2 11.2 2500.0 22.4 109.2 0.62 0.32 Example (12) P-47 6.0 12.7 2500.0 19.6 114.3 0.61 0.35 Example (13) P-50 6.1 12.6 2500.0 19.8 112.9 0.62 0.33 Example (14) P-55 5.8 13.3 2500.0 18.8 105.3 0.63 0.34 Example (15) P-57 6.4 12.3 2500.0 20.4 107.9 0.64 0.34 Example (16) P-64 6.2 11.3 2500.0 22.2 109.7 0.61 0.32 Example (17) P-72 5.8 13.6 2500.0 18.4 106.9 0.62 0.33 Example (18) P-91 5.8 13.4 2500.0 18.7 106.1 0.61 0.34 Example (19) P-103 6.3 11.0 2500.0 22.6 109.2 0.63 0.32 Example (20) P-122 6.3 11.2 2500.0 22.3 109.3 0.61 0.32 Example (21) P-133 5.8 13.4 2500.0 18.7 106.0 0.63 0.33 Example (22) P-143 6.3 11.2 2500.0 22.4 109.8 0.62 0.35 Example (23) P-169 6.3 11.2 2500.0 22.4 109.1 0.63 0.32

As can be seen from the results of Table 3, when a red organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, organic electricity It can be seen that not only can the driving voltage of the light emitting device be lowered, but also the luminous efficiency and lifespan can be remarkably improved.

In order to examine the effects of the compounds of the present invention, a compound having relatively high structural similarity was set as a comparative group. Therefore, the compounds of the present invention resulted in remarkably excellent device results that were not predicted by those skilled in the art.

In the above, the present invention has been exemplarily described, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the claims below, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

100, 200, 300: organic electric device
110, 110, 310: first electrode
120, 220, 320: hole injection layer
321: first hole injection layer
130, 230: hole transport layer
331: first hole transport layer
332: second hole transport layer
243: buffer layer
253: light emission auxiliary layer
140, 240: light emitting layer
341: first light-emitting layer
342: second light-emitting layer
150, 250: electron transport layer
351: first electron transport layer
352: second electron transport layer
160, 260, 360: electron injection layer
170, 270, 370: second electrode
180, 280, 380: capping layer
390: first charge generation layer
391: second charge generation layer
ST1: 1st stack
ST2: 2nd stack
CGL: charge generation layer

Claims (11)

A compound represented by the following formula (1):
Formula (1)

In the above formula (1),
1) T is CR'R'', NR''', O or S,
2) X ¹ and X ² are each independently selected from the group consisting of CR'R'', NR''', O and S,
3) Y ¹ and Y ² are each independently selected from the group consisting of CR'R'', NR''', O and S,
4) Z ¹ and Z ² are each independently selected from the group consisting of CR'R'', NR''', O and S,
5) a to f are, each independently, 0 or 1, a+b, c+d and e+f are 1,
6) R'and R'' are each independently hydrogen; C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom, can be bonded to each other to form a spy compound,
7) R'" is each independently hydrogen; C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom,
8) R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ¹ to R ⁴ may be bonded to each other to form a ring,
9) R ⁵ to R ⁸ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ⁵ to R ⁸ may be bonded to each other to form a ring,
10) R ⁹ to R ¹² are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, neighboring R ⁹ to R ¹² may be bonded to each other to form a ring,
11) L'is each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ of the heterocyclic group; is selected from the group consisting of,
12) R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,
13) In the above, R', R'', R''', R ¹ to R ¹² , L', R _a and R _b , the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group , Alkenyl group, alkynyl group, alkoxyl group, aryloxy group, alkylene group, arylene group, and fluorenylene group are deuterium, respectively; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; An alkoxyl group of C ₁ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and the additionally substituted substituents may be bonded to each other to form a ring. And each of the additionally substituted substituents is deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; An alkoxyl group of C ₁ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And one or more substituents selected from the group consisting of C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring.
The method of claim 1,
R'and R'' are each independently hydrogen; It is selected from the group consisting of a C ₁ ~ C ₂₀ alkyl group and a C ₆ ~ C ₂₀ aryl group,
R''' is each independently hydrogen; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₅ aryl group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₂₀ containing at least one heteroatom,
R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Or an alkenyl group of C ₂ to C ₂₀ , and adjacent R ¹ to R ^{4 may} be bonded to each other to form a ring,
R ⁵ to R ⁸ are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Or an alkenyl group of C ₂ to C ₂₀ , and adjacent R ⁵ to R ^{8 may} be bonded to each other to form a ring,
R ⁹ to R ¹² are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Or a C ₂ ~ C ₂₀ alkenyl group, a compound capable of forming a ring by bonding of adjacent R ⁹ to R ^{12 with} each other.
The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (2) to (5):
Formula (2) Formula (3)

Formula (4) Formula (5)

In the above formulas (2) to (5), T, X ¹ , Y ¹ , Y ² , Z ¹ , Z ² and R ¹ to R ¹² are the same as defined in the formula (1) of claim ¹ .
The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (6) to (9):
Formula (6) Formula (7)

Formula (8) Formula (9)

In the above formulas (6) to (9), T, X ² , Y ¹ , Y ² , Z ¹ , Z ² and R ¹ to R ¹² are the same as defined in the formula (1) of claim ¹ .
The compound according to claim 1, wherein the compound represented by formula (1) is represented as follows:

.
A first electrode;
A second electrode; And
Including; an organic material layer positioned between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound of claim 1.
The method of claim 6,
The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, a transfer auxiliary layer, an electron transport layer and an electron injection layer,
At least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injection layer included in the organic material layer comprises the compound of claim 1.
The method of claim 6,
The organic material layer includes a light emitting layer,
An organic electric device in which the emission layer comprises the compound of claim 1.
The method of claim 6,
The organic material layer includes a first stack, a charge generation layer disposed on the first stack, and a second stack disposed on the charge generation layer,
The first stack includes a first emission layer, and the second stack includes a second emission layer.
A first electrode;
A second electrode;
An organic material layer positioned between the first electrode and the second electrode; And
A capping layer disposed on one or more of one surface of the first electrode opposite to the organic material layer and one surface of the second electrode opposite to the organic material layer; and
At least one of the organic material layer and the capping layer is an organic electric device comprising the compound of claim 1.
The method of claim 10,
The organic material layer includes a first stack, a charge generation layer disposed on the first stack, and a second stack disposed on the charge generation layer,
The first stack includes a first emission layer, and the second stack includes a second emission layer.

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