KR102642129B1 - Compound for organic electric element and organic electric device comprising the same - Google Patents

Abstract

Embodiments of the present invention relate to compounds for organic electric devices that can improve high luminous efficiency, low driving voltage, high heat resistance, color purity, or lifespan, and organic electric devices using the same.

Description

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

Embodiments of the present invention relate to compounds for organic electric devices and organic electric devices using the same.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electric devices using the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic electric device, and may be composed 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 organic layers in organic electric devices 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, depending on their function.

In addition, the light-emitting material can be classified into high-molecular type and low-molecular type depending on the molecular weight, and can be classified into fluorescent material derived from the singlet excited state of electrons and phosphorescent material derived from the triplet excited state of electrons depending on the luminescence mechanism. You can. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials necessary to realize better natural colors, depending on the color of the light.

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and problems arise such as a decrease in color purity or a decrease in the efficiency of the device due to the emission attenuation effect, which increases color purity and energy transfer. In order to increase luminous efficiency through , a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap than the host forming the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

Currently, the portable display market is increasing in size toward large-area displays. Since portable displays have batteries that provide limited power, more efficient power consumption is required than that required by existing portable displays. In addition, in addition to efficient power consumption, luminous efficiency and lifespan issues must also be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. It indicates a tendency for lifespan to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined. Therefore, there is a need to develop a light-emitting material that has high thermal stability and can efficiently achieve charge balance within the light-emitting layer.

In other words, in order to fully demonstrate the excellent characteristics of organic electric devices, the materials that make up the organic layer within 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, must be stable and efficient. Support by materials must be a priority, but the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed. Therefore, the development of new materials continues to be required, and in particular, the development of host materials for the light-emitting layer is urgently required.

Embodiments of the present invention can provide a compound that can improve high heat resistance, color purity, and lifespan while lowering the driving voltage of the 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 containing the same, and an electronic device thereof.

Chemical formula (1)

According to embodiments of the present invention, by using the compounds according to the embodiments of the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device are greatly improved. Devices can be provided.

1 to 3 are diagrams schematically showing 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 the exemplary drawings.

In adding reference numerals to components in each drawing, the same components may have the same reference numerals as much as possible even if they are shown in different drawings. Additionally, when describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description may be omitted. When “comprises,” “has,” “consists of,” etc. mentioned in the specification are used, other parts may be added unless “only” is used. When a component is expressed in the singular, it can also include the plural, unless specifically stated otherwise.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, order, or number of the components are not limited by the term.

In the description of the positional relationship of 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 should be understood that two or more components and other components may be further "interposed" and "connected," "combined," or "connected." Here, other components may be included in one or more of two or more components that are “connected,” “coupled,” or “connected” to each other.

Additionally, when a component, such as a layer, membrane, region, plate, etc., is said to be "on" or "on" another component, it means not only that it is "directly above" the other component, but also that there is another component in between. It should be understood that it can also include cases. Conversely, when an element is said to be "right on top" of another part, it should be understood to mean that there is no other part in between.

In the description of temporal flow relationships related to components, operation methods, production methods, etc., for example, temporal precedence relationships such as “after”, “after”, “after”, “before”, etc. Or, when a sequential relationship is described, non-continuous cases may be included unless “immediately” or “directly” is used.

Meanwhile, when numerical values or corresponding information about a component are mentioned, even if there is no separate explicit statement, the numerical value or corresponding information may be caused by various factors (e.g., process factors, internal or external shocks, noise, etc.). It can be interpreted as including a possible margin of error.

As used in this application, the term “halo” or “halogen” includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), etc., unless otherwise specified.

As used in this application, the term "alkyl" or "alkyl group", unless otherwise specified, has 1 to 60 carbons connected by a single bond, and includes a straight chain alkyl group, branched chain alkyl group, cycloalkyl (cycloaliphatic) group, and alkyl-substituted group. It may refer to a radical of a saturated aliphatic functional group, including a cycloalkyl group and a cycloalkyl-substituted alkyl group.

The term “haloalkyl group” or “halogenalkyl group” used in this application may mean an alkyl group in which halogen is substituted, unless otherwise specified.

Unless otherwise specified, the terms “alkenyl” or “alkynyl” used in this application have a double or triple bond, include a straight or branched chain group, and may have 2 to 60 carbon atoms.

The term “cycloalkyl” used in this application may mean alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified.

The term “alkoxy group” or “alkyloxy group” used in this application refers to an alkyl group to which an oxygen radical is bonded, and may have 1 to 60 carbon atoms, unless otherwise specified.

As used in this application, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It can have a number of carbon atoms.

The terms “aryl group” and “arylene group” used in this application each have 6 to 60 carbon atoms unless otherwise specified, but are not limited thereto. In the present application, an aryl group or arylene group may include a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc. For example, aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, anthryl, indenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. That is not the case. 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 term “fluorenyl group” or “fluorenylene group” may refer to a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified. Additionally, 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. This may include a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

The term "spiro compound" used in this application has a 'spiro union', and the spiro union refers to a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It can be said to be a compound.

The term "heterocyclic group" used in this application includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and unless otherwise specified, each carbon number containing one or more heteroatoms. It refers to a ring numbered from 2 to 60, but is not limited thereto. As used in this application, the term "heteroatom" refers to N, O, S, P, or Si, unless otherwise specified, and the heterocyclic group refers to a single ring containing heteroatoms, a ring assembly, a fused multiple ring system, or a ring group. It may mean a compound, etc.

Additionally, the “heterocyclic group” may also include a ring containing SO ₂ instead of carbon forming the ring. For example, “heterocyclic group” may include the following compounds.

The term “ring” used in this application includes single rings and polycyclic rings, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and may include aromatic and non-aromatic rings.

As used in this application, the term "polycyclic" includes ring assemblies, fused multiple ring systems, and spiro compounds, includes aromatics as well as non-aromatics, and includes hydrocarbon rings as well as at least one heterocyclic ring. It may contain a heterocycle containing an atom.

The term "aliphatic ring" used in this application refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes single rings, ring aggregates, fused multiple ring systems, spiro compounds, etc., and has the number of carbon atoms unless otherwise specified. It may mean a ring of 3 to 60. For example, even when benzene, an aromatic ring, and cyclohexane, a non-aromatic ring, are fused, it is an aliphatic ring.

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

As used in this application, the term “fused multiple ring system” refers to a fused ring form that shares at least two atoms. For example, the aryl group may be a naphthalenyl group, phenanthrenyl group, fluorenyl group, etc., but is not limited thereto.

Additionally, when prefixes are named consecutively, it may mean that the substituents are listed in the order they are listed 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 in an alkoxy group, and in the case of an arylcarbonylalkenyl group, it can mean an alkenyl group substituted in an arylcarbonyl group. there is. Here, the arylcarbonyl group may be a carbonyl group substituted with an aryl group.

Also, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in this application, "substituted" means 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 group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, boron means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P. It can be done, and is not limited to these substituents.

In this application, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., exemplified by each symbol and its substituent, may be written as the 'name of the functional group reflecting the valence', but is written as the 'parent compound name'. You may. For example, in the case of 'phenanthrene', a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', the divalent group is 'phenanthrylene (group)', etc., and the name of the group is written by dividing the valence. However, it can also be written as 'phenanthrene', which is the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or the 'group' of the corresponding valence, such as pyrimidinyl (group) in the case of monovalent, pyrimidinylene (group) in the case of divalent, etc. It can also be written as ‘name’. Therefore, in the present application, when the type of substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by detachment of a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

Additionally, unless explicitly stated otherwise, the chemical formula used in this application can be applied identically to the substituent definition by the index definition in the following chemical formula.

Here, when a is 0, it means that the substituent R ¹ is absent, which means that hydrogen is bonded to all carbons forming the benzene ring. In this case, the indication of hydrogen bonded to carbon is omitted and the chemical formula or compound is written. It can be listed. In addition, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is 2 or 3, it can be bonded as follows, respectively, and a is 4 to 6 If it is an integer, it is bonded to the carbon of the benzene ring in a similar way, and if a is an integer of 2 or more, R ¹ may be the same or different.

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

In this application, the organic electric device may refer to the component(s) between the anode and the cathode, or may refer to the organic light emitting diode including the anode, the cathode, and the component(s) located between them.

Additionally, depending on the case, 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, electronic devices include display devices, lighting devices, solar cells, portable or mobile terminals (e.g. smart phones, tablets, PDAs, electronic dictionaries, PMPs, etc.), navigation terminals, game consoles, various TVs, and various computers. It may include a monitor, etc., but is not limited thereto, and may be any type of device as long as it includes the above component(s).

Organic electric device Figures 1 to 3 are illustrative diagrams of organic electric devices according to embodiments of the present invention.

First, referring to FIG. 1, the 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). and the second electrode 170 may include an organic material layer containing a compound according to the present invention, and additionally, a capping layer 180 may or may not be formed.

The first electrode 110 in FIG. 1 may be an anode, and the second electrode 170 may be a cathode. In the case of the 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, a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160 may be sequentially disposed on the first electrode 110.

In addition, referring to Figure 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 ( 243), a light emitting auxiliary layer 253, a light emitting layer 240, an electron transport layer 250, an electron injection layer 260, and a second electrode 270 may be included, and a capping layer 280 may be additionally formed. It may or 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, the organic electric device 300 according to another embodiment of the present invention has a stack (ST1, ST2) of a multi-layer organic material layer between the first electrode 310 and the second electrode 370. More than one set may be placed. For example, the first stack (ST1) is disposed on the first electrode 310, the second stack (ST2) is disposed on the first stack (ST1), and the second stack (ST2) is disposed on the second stack (ST2). Electrodes 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. It may include (380).

The first stack (ST1) is an organic material layer formed on the first electrode 310, which includes a first hole injection layer 321, a first hole transport layer 331, a first light emitting layer 341, and a first electron transport layer 351. ), and the second stack (ST2) may include a second hole transport layer 332, a second light-emitting 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. In this way, 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. By being disposed between the first and second light-emitting layers 341 and 342, the charge generation layer (CGL) can serve to increase the efficiency of current generated in each light-emitting layer and to smoothly distribute charges.

The first light-emitting layer 341 may include a light-emitting material containing a blue fluorescent dopant in a blue host, and the second light-emitting layer 342 may contain a material doped with a greenish yellow dopant and a red dopant in a green host. However, the materials of the first and second light emitting layers 341 and 342 according to the embodiment of the present invention are 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 from 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 one or more of the surfaces of the first electrodes 110, 210, and 310 opposite the organic layer and one side of the second electrodes 170, 270, and 370 opposite the organic layer. , 280, 380) can be formed.

Additionally, when a capping layer is formed, the luminous efficiency of the organic electric device can be improved.

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

On the other hand, when a plurality of light-emitting layers are formed using a multi-layer stack structure as shown in FIG. 3, an organic electro-electric device that emits white light can be manufactured by the mixing effect of the light emitted from each light-emitting layer.

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

On the other hand, even if it is the same core, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of sub-substituents attached to it are important. Research is needed, and in particular, long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

Organic electric devices according to 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, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode (110, 210, 310) is formed thereon, and a hole injection layer (120, 220, 321), a hole transport layer (130, 230, 331, 332), a light emitting layer (140, 240, 341, 342), and an electron transport layer (150, 250, 351) are formed thereon. , 352) and an electron injection layer (160, 260, 360), and then depositing a material that can be used as a cathode (170, 270, 370) thereon.

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

The organic electric device according to an embodiment of the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to achieve high resolution and having excellent fairness, while being manufactured using existing LCD color filter technology. Various structures for white organic electric devices, mainly used as backlight devices, are being proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel with each other in a plane, and a stacking method in which R, G, and B light emitting layers are stacked top and bottom. There is a color conversion material (CCM) method that uses electroluminescence by a blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom, and the present invention. can be applied to these WOLEDs as well.

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

Chemical formula (1)

The substituents and linking groups described in the above formula (1) are explained as follows.

T may 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 the two carbons shown as 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; Aryl group of C ₆ to C ₆₀ ; and C ₂ to C ₆₀ heterocyclic groups containing at least one hetero atom selected from O, N, S, Si, and P, and may be combined with each other to form a spiro 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 -C ₅₀ alkyl group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₁₀ alkyl group, or a methyl group.

When R' or R'' is an aryl group, for example, each independently represents an aryl group of C ₆ to C ₆₀ , an aryl group of C ₆ to C ₄₀ , an aryl group of C ₆ to C ₂₀ , or an aryl group of C ₆ to C _10. It may be an aryl group or phenyl group.

R''' is, each independently, hydrogen; C ₁ ~ C ₅₀ alkyl group; Aryl group of C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

When R''' is an alkyl group, for example, it may be a C ₁ -C ₅₀ alkyl group, a C ₁ -C ₃₀ alkyl group, or a C ₁ -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 to C ₆₀ heterocyclic group, a C ₂ to C ₄₀ heterocyclic group, or a C ₂ to C ₂₀ heterocyclic group.

R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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 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; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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 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; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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 adjacent 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 from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; may be selected from the group consisting of.

R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

In 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 each deuterium; nitro group; Nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; It may be additionally substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group. Therefore, when R', R'', R''', R ¹ to R ¹² , L', R _a and R _b are understood as primary substituents, the additional substituents are understood as secondary substituents. You can.

In addition, the additionally substituted substituents (secondary substituents) may be combined with each other to form a ring, and the additionally substituted substituents are each hydrogen; nitro group; Nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ to C ₂₀ arylalkenyl groups may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring. Therefore, substituents additionally substituted on the secondary substituent may be understood as tertiary substituents.

The compound represented by the formula (1) may be represented by any one of the following formulas (2) to (9).

Formula (2) Formula (3)

Formula (4) Formula (5)

Formula (6) Formula (7)

Formula (8) Formula (9)

In the above formulas ^{( 2 ) to} ( ⁹ ) ^{, T ,}

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

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

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

On the other hand, the organic electric device includes a first electrode, a second electrode, an organic material layer located between the first electrode and the second electrode, one side of the first electrode opposite to the organic material layer, and the second electrode. It may include a capping layer located on one or more of the surfaces opposite to the organic layer, and at least one of the organic 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 multi-layer structure.

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

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

In another example, the compound represented by Formula (1) may be included in at least one light-emitting layer included in the organic material layer.

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

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

In another example, a layer containing the compound alone, in a combination of two or more different compounds, or in a combination of two or more compounds with other compounds may be a light-emitting layer.

Each layer may contain a compound corresponding to the formula (1) alone or a mixture of two or more compounds of the formula (1), a compound of the formula (1), and a compound that does not correspond to the present invention. A mixture of and may be included. Here, the compound that does not fall under the present invention may be a single compound, or may be two or more types of compounds.

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

For example, the organic layer may be a mixture of two compounds with different structures at a molar ratio of 99:1 to 1:99.

Another embodiment of the present invention further includes 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 electrical devices. The capping layer may include a compound represented by Chemical Formula (1) according to the present invention.

The capping layer contains the compound of the present invention alone, the compound of the present invention in a combination of two or more different types, or the compound of the present invention in a combination of two or more types with other compounds. Devices are provided.

Another embodiment of the present application provides an organic electric device characterized in that the compound represented by Chemical Formula (1) is mixed in any of the ratios of 1:9 to 9:1 and used in the light-emitting layer.

Hereinafter, examples of synthesis of the compound represented by formula (1) and examples of manufacturing organic electric devices according to the present invention will be described in detail through examples, but the present invention is not limited to the following examples.

[Synthesis example]

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

(V) The details of the method are explained in detail in the section on Scheme 17, which will be described later.

1. Manufacturing method according to Scheme 1

<Scheme 1>

Sub A synthesis example

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

<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 (86.4 mL, 216.01 mmol) was slowly added dropwise over 1 hour. After dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (73.02g, 648.03 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with MC (methylene chloride), and concentrate. 30.54 g of product (yield: 72%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 2-4

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

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

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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (62.96g, 605.97 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 28.32 g of product (yield: 66%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 14-4

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

(3) Synthesis of Sub A-14

Sub 14-4 (37 g, 98.06 mmol), Pd ₂ (dba) ₃ (2.24 g, 2.45 mmol), t-BuONa (28.27 g, 294.19 mmol), P(t-Bu)3 (1.98 mmol) obtained from the above synthesis. g, 4.90 mmol, Toluene (600 ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was placed on a silicagel column and recrystallized. 18.04g of product (yield: 54%) was obtained.

2. Manufacturing method according to Scheme 3

<Scheme 3>

Sub B synthesis example

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

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (43.70g, 420.58 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 27.04 g of product (yield: 60%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 30-4

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

(3) Synthesis of Sub B-30

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

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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (40.72g, 391.96 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 29.52 g of product (yield: 65%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 37-4

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

(3) Synthesis of Sub B-37

Sub 37-4 (32 g, 57.91 mmol), Pd ₂ (dba) ₃ (2.65 g, 2.89 mmol), t-BuONa (16.69 g, 173.75 mmol), P(t-Bu) 3 (2.34) obtained from the above synthesis. g, 5.79 mmol, Toluene (600 ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was placed on a silicagel column and recrystallized. 13.79 g of product (yield: 49%) was obtained.

3. Manufacturing method according to Scheme 5

<Scheme 5>

Sub C synthesis example

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

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (60.51g, 582.38 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 31.96 g of product (yield: 74%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 42-4

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

(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 (4.26 g, 4.66 mmol), t-BuONa (26.87 g, 279.68) obtained from the above synthesis. mmol), P(t-Bu)3 (3.77 g, 9.32 mmol, Toluene (1000 ml) were added and stirred at 110 °C. When the reaction was completed, the reaction was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ . After concentration, the resulting compound was recrystallized using a silicagel column to obtain 37.64g of product (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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (39.29 g, 378.14 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 28.71 g of product (yield: 63%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 51-4

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

(3) Synthesis of Sub C-51

Sub 51-4 (25 g, 45.24 mmol), Pd ₂ (dba) ₃ (1.03 g, 1.13 mmol), t-BuONa (13.04 g, 135.74 mmol), P(t-Bu)3 (0.91) obtained from the above synthesis. g, 2.26 mmol, Toluene (600 ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column. 17.98 g of product (yield: 77%) was obtained.

4. Manufacturing method according to Scheme 7

<Scheme 7>

Sub D synthesis example

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

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (36.01 g, 346.62 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 26.64 g of product (yield: 58%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 68-4

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

(3) Synthesis of Sub D-68

Sub 68-4 (28 g, 40.60 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.01 mmol), t-BuONa (11.70 g, 121.80 mmol), P(t-Bu) 3 (0.82) obtained from the above synthesis. g, 2.03 mmol, Toluene (600 ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column. 14.54 g of product (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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (62.96 g, 605.98 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 22.74 g of product (yield: 53%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 78-4

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

(3) Synthesis of Sub D-78

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

5. Manufacturing method according to Scheme 9

<Scheme 9>

Sub E synthesis example

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

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (43.70 g, 420.58 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 33.36 g of product (yield: 74%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 81-4

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

(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 from the above synthesis mmol), P(t-Bu)3 (2.40 g, 5.94 mmol), and Toluene (600 ml) were added and stirred at 110 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 21.84 g of product (yield: 70%).

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 over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 27.46 g of product (yield: 64%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 91-4

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

(3) Synthesis of Sub E-91

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

6. Manufacturing method according to Scheme 11

<Scheme 11>

Sub F synthesis example

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

<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 over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 27.46 g of product (yield: 64%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 107-4

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

(3) Synthesis of Sub F-107

Sub 107-4 (35 g, 92.76 mmol), Pd ₂ (dba) ₃ (2.12 g, 2.31 mmol), t-BuONa (26.74 g, 278.29 mmol), P(t-Bu) 3 (1.87) obtained from the above synthesis. g, 4.63 mmol, Toluene (700ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column. 19.28 g of product (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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (60.51 g, 582.38 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 33.25 g of product (yield: 77%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 118-4

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

(3) Synthesis of Sub F-118

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

7. Manufacturing method according to Scheme 13

<Scheme 13>

Sub G synthesis example

Sub G of Scheme 13 can be synthesized through the reaction route of Scheme 14 below, but is not limited thereto.

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (62.96 g, 605.98 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 21.45 g of product (yield: 50%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 123-4

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

(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 from the above synthesis. mmol), P(t-Bu)3 (2.87 g, 7.11 mmol), and Toluene (600 ml) were added and stirred at 110 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 28.02 g of product (yield: 71%).

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 dropwise addition, the mixture was stirred at -78°C for 1 hour, then trimethyl borate (67.33 g, 648.03 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 29.27 g of product (yield: 69%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 132-4

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

(3) Synthesis of Sub G-132

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

8. Manufacturing method according to Scheme 15

<Scheme 15>

Sub H synthesis example

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

<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 dropwise addition and stirring at -78°C for 1 hour, trimethyl borate (43.70 g, 420.58 mmol) was added dropwise over 30 minutes, and the reaction was terminated by stirring at room temperature for 4 hours. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 30.65 g of product (yield: 68%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 148-4

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

(3) Synthesis of Sub H-148

Sub 148-4 (34 g, 69.89 mmol), Pd ₂ (dba) ₃ (1.60 g, 1.74 mmol), t-BuONa (20.15 g, 209.69 mmol), P(t-Bu) 3 (1.41) obtained from the above synthesis. g, 3.49 mmol, Toluene (680ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column. 19.81 g of product (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 over 30 minutes and stirred at room temperature for 4 hours to terminate the reaction. Neutralize with 1N HCl, extract with CH2Cl2 and concentrate. 25.87 g of product (yield: 61%) was obtained through silicagel column and recrystallization.

(2) Synthesis of Sub 158-4

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

(3) Synthesis of Sub H-158

Sub 148-4 (44 g, 79.63 mmol), Pd ₂ (dba) ₃ (1.82 g, 1.99 mmol), t-BuONa (22.95 g, 238.91 mmol), P(t-Bu) 3 (1.61) obtained from the above synthesis. g, 3.98 mmol, Toluene (680ml) was added and stirred at 110 ° C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column. 20.51 g of product (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 according to Schemes 1, 3, 5, 7, 9, 11, 13 and 15 can produce Products 1 to 32 through the reaction routes of Scheme 17 and Scheme 18 below. The manufacturing method is not limited to this.

<Scheme 17>

If you refer to Scheme 17 above, you will be able to understand method (V) according to the final product to be manufactured in Scheme 1.

The manufacturing method of the specific compound is as follows.

Example of synthesis 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) and water (150 ml) were added and stirred at 80 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25.31 g of product (yield: 71%).

(2) Synthesis of Sub A-2-3

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

(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, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.09 g of product (yield: 66%).

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, dissolved in THF (tetrahydrofuran) (180 ml), and 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), and water (90 ml) were added and stirred at 80 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 18.37 g of product (yield: 79%).

(2) Synthesis of P-14

Sub A-14-2 (18 g, 40.85mmol) obtained in the above synthesis was placed in a reactor and dissolved in THF (tetrahydrofuran) (180 ml), then methylmagnesium bromide 1.0M in THF (tetrahydrofuran) (122.57 ml, 122.57 mmol) was added. After slowly adding it dropwise, it was stirred at room temperature. When the reaction was completed, extraction was performed with diethyl ether and water, and the organic layer was dried with 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 refluxed. When the reaction was completed, water was added and stirred, and the resulting solid was filtered under reduced pressure and 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), 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), and water (185 ml) were added and stirred at 80 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 28.45 g of product (yield: 70%).

(2) Synthesis of P-42

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

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), 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), and water (140 ml) were added and stirred at 80 °C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 22.05 g of product (yield: 68%).

(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 and reacted at an internal temperature of 30 °C for 24 days. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 18.26 g of product (yield: 81%).

(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 and stirred at room temperature for 24 hours, then water and Pyridine (8:1) were slowly added and stirred. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 7.52 g of product (yield: 44%).

<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 of product (yield: 69%) was obtained using the 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 was 9.44 g (yield) 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 of product (yield: 88%) was obtained using the 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), 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 of product (yield: 85%) was obtained using the P-123 synthesis method.

(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 12.61 g of product (12.61 g ( Yield: 64%) was obtained.

(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 and stirred at room temperature for 24 hours, then water and Pyridine (8:1) were slowly added using the P-123 synthesis method. 7.23 g of product (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), 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 of product (yield: 74%) 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 the reactor along with Pd(OAc) ₂ (0.33 g, 1.47 mmol) and 3-nitropyridine (0.18 g, 1.47 mmol) and C ₆ After dissolving in F ₆ (60 ml) and DMI (30 ml), tert -butyl peroxybenzoate (11.47 g, 59.10 mmol) was added and 10.15 g of product (yield: 68%) 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, dissolved in THF (tetrahydrofuran) (200 ml), and 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 of product (yield: 49%) 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 placed in 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 it dropwise, it was stirred at room temperature. When the reaction was completed, extraction was performed with diethyl ether and water, and the organic layer was dried with 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 refluxed. When the reaction was completed, water was added and stirred, and the resulting solid was filtered under reduced pressure and washed with water and methanol to obtain 7.78 g of the product as a white powder (yield: 73%).

Meanwhile, the FD-MS values of compounds P-1 to P-173 of the present invention prepared according to the above synthesis examples 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 O S 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 O S 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 O S 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 O S 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 O S 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 N S 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 O S 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 testing 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 60 nm thick film. 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 this film to form a hole transport layer. was formed. The above invention compound represented by Chemical Formula (1) was used as a host on the upper part of the hole transport layer, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(²)acetylacetonate] was used as a dopant in a weight of 95:5. By doping, a 30 nm thick light emitting layer was deposited on the hole transport layer. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinoline oleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole-blocking layer, and the electron transport layer Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a film with a thickness of 40 nm. Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

A forward bias direct current voltage was applied to the organic electroluminescent devices of Examples and Comparative Examples manufactured in this way, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch. As a result of the measurement, the electroluminescence (EL) characteristics were measured at a standard luminance of 2500 cd/m2. The T95 lifespan was measured using a lifespan measuring device 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 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 in 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, the organic electroluminescent device was produced more efficiently than the comparative examples using Comparative Compounds A to C. 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 significantly improved.

In order to examine the effect of the compounds of the present invention, compounds with relatively high structural similarity were set as comparison groups. However, in conclusion, Comparative Compounds A to C are structurally different from the compounds of the present invention, so their chemical and physical properties are significantly different. As a result, the compound of the present invention produced remarkably excellent device results that were completely unexpected by those skilled in the art.

Above, the present invention has been described by way of example, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting 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 in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights 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-emitting 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: first stack
ST2: second stack
CGL: charge generation layer

Claims (11)

Compound represented by the following formula (1):
Chemical 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, and a+b, c+d and e+f are 1,
6) R' and R'' are each independently hydrogen; C ₁ ~ C ₅₀ alkyl group; Aryl group of C ₆ to C ₆₀ ; and C ₂ to C ₆₀ heterocyclic groups containing at least one hetero atom selected from O, N, S, Si, and P, and can be combined with each other to form a spiro compound;
7) R''' is, each independently, hydrogen; C ₁ ~ C ₅₀ alkyl group; Aryl group of C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
8) R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent 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 from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of,
12) R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
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 each deuterium; nitro group; Nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; 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 combined with each other to form a ring. Each of the additionally substituted substituents is deuterium; nitro group; Nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and may be further substituted with one or more substituents selected from the group consisting of C ₈ to C ₂₀ arylalkenyl groups, and these substituents may be combined with each other to form a ring.
According to clause 1,
R' and R'' are each independently hydrogen; 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 a C ₂ to C ₂₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; C ₁ ~ C ₂₀ alkyl group; Or it is 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 it is 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 compound that is an alkenyl group of C ₂ to C ₂₀ and can form a ring by combining adjacent R ⁹ to R ¹² groups.
The compound according to claim 1, wherein the compound represented by the 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 ^,
The compound according to claim 1, wherein the compound represented by the 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 ^,
The compound according to claim 1, wherein the compound represented by formula (1) is represented by:
























.
first electrode;
second electrode; and
It includes; an organic material layer located between the first electrode and the second electrode,
The organic material layer is an organic electric device containing the compound of claim 1.
According to clause 6,
The organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer,
An organic electric device wherein at least one layer of a hole injection layer, a hole transport layer, a light emitting 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 contains the compound of claim 1.
According to clause 6,
The organic layer includes a light-emitting layer,
An organic electric device wherein the light-emitting layer includes the compound of claim 1.
According to clause 6,
The organic material layer includes a first stack, a charge generation layer located on the first stack, and a second stack located on the charge generation layer,
The first stack includes a first light-emitting layer, and the second stack includes a second light-emitting layer.
first electrode;
second electrode;
An organic material layer located between the first electrode and the second electrode; and
A capping layer located on one or more of one side of the first electrode opposite to the organic layer and one side of the second electrode opposite to the organic layer,
An organic electric device wherein at least one of the organic material layer and the capping layer includes the compound of claim 1.
According to clause 10,
The organic material layer includes a first stack, a charge generation layer located on the first stack, and a second stack located on the charge generation layer,
The first stack includes a first light-emitting layer, and the second stack includes a second light-emitting layer.