KR20220000007A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric element including an anode, a cathode and an organic material layer and a capping layer formed between the anode and the cathode, and an electronic device including the organic electric device. Since the capping layer includes the compound represented by chemical formula 1 of the present invention, it is possible to lower the driving voltage of the organic electric device and improve luminous efficiency and lifespan.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof

The present invention relates to an organic electric device including a capping layer and an electronic device including the same.

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

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function. In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. have. In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

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

Lifespan and efficiency are the most problematic for organic light emitting devices, and as displays become larger, these problems of efficiency and lifespan must be solved. Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized by simply improving the organic material layer, and the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) Only when this is achieved can a long lifespan and high efficiency be achieved at the same time. Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. In other words, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. However, the development of a stable and efficient organic material layer material for an organic electric device has not yet been sufficiently made, and among them, the development of a material for the light emitting layer is urgently required.

Recently, not only research on improving device characteristics by changing the performance of each material, but also technology for improving color purity and increasing efficiency by optimized optical thickness between anode and cathode in top devices with resonance structures It is one of the important factors to improve the device performance. Compared to the bottom device structure of the non-resonant structure, the top device structure has a large optical energy loss due to surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflective film, and emitted toward the cathode.

Therefore, one of the important methods for improving the shape and efficiency of EL Spectral is a method of using a light efficiency improving layer for the top cathode. In general, in SPP, Al, Pt, Ag, and Au, these four metals are mainly used for electron emission, and surface plasmon is generated on the surface of the metal electrode. For example, when the cathode is used as Ag, the light emitted by the Ag of the cathode is quenched by SPP (light energy loss due to Ag) and the efficiency is reduced.

On the other hand, when the light efficiency improvement layer is used, SPP occurs at the interface between the MgAg electrode and the high refractive organic material, and among them, TE (transverse electric) polarized light is annihilated in the vertical direction by the evanescent wave on the light efficiency improvement layer surface, In the case of TM (transverse magnetic) polarized light moving along the cathode and the light efficiency improvement layer, the wavelength is amplified by surface plasma resonance, which increases the intensity of the peak and eventually high Efficiency and effective color purity control are possible.

The present invention uses MgAg having an Ag ratio of 80% or more as a cathode and a capping layer material having a loss tangent value of 0.001 or less at a wavelength of 450 nm in order to realize a high-efficiency, long-life device, which is a required characteristic of an organic electric device. characterized.

In one aspect, the present invention provides a positive electrode; cathode; an organic material layer formed between the anode and the cathode; and a capping layer, wherein the organic material layer includes a hole transport region, a light emitting layer and an electron transport region, the electron transport region includes an electron transport layer and an electron injection layer, and the cathode is magnesium (Mg ) and silver (Ag), wherein the ratio of silver (Ag) is 80% or more, and the capping layer includes a compound satisfying the following formula 1 at a wavelength of 450 nm. provides

[Equation 1]

tanδ (Loss tangent) ≤ 0.001

{In the above formula 1,

1) tanδ is ε ² /ε ¹ ,

2) ε ² is the imaginary part of the complex permittivity of the dielectric material representing the dielectric loss, expressed as 2nk,

3) ε ¹ is the real part of the complex permittivity representing the permittivity, denoted by n ² -k ² ,

4) n is the refractive index, and k is the absorption coefficient.}

In addition, the present invention provides an organic electric device, characterized in that the capping layer satisfies Formula 1 and is a compound represented by Formula 1 below.

[Formula 1]

In another aspect, the present invention provides an electronic device including the organic electric device.

By using the compound according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be greatly improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.

Hereinafter, it will be described in detail with reference to embodiments of the present invention. In 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 thereof will be omitted.

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”

As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings:

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond of 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups and cycloalkyl-substituted alkyl groups.

As used herein, the terms "alkenyl group", "alkenyl group" or "alkynyl group" have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise specified, and include a straight or branched chain group, , but not limited thereto.

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, and is limited thereto. it is not

As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the number of carbon atoms described herein.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group and wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a hetero aromatic rings. It may be formed by combining adjacent functional groups.

As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.

In addition, the "heterocyclic group" may include a ring containing _{SO 2 instead of carbon forming the ring.} For example, "heterocyclic group" includes the following compounds.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to It includes the case of forming a compound as a spy together.

The term "spiro compound" used in the present invention has a 'spiro union', and the spiro linkage means a connection formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

Unless otherwise specified, as used herein, the term "aliphatic" refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a combination thereof, It contains saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.

In addition, unless otherwise explicitly stated, in the term "substituted or unsubstituted" used in the present invention, "substitution" 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 alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, but is not limited to these substituents.}

In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same way as the definition of the substituent by the exponent definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3 Each is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .

In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though they are indicated on different drawings. In addition, in 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 thereof will be omitted.

1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). ) and an organic material layer formed between the second electrode 170 .

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

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

Preferably, a capping layer (light efficiency improving layer; 180) may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and the capping layer 80 is formed. In this case, the luminous efficiency of the organic electric device may be improved.

For example, a capping layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the capping layer 180 is formed on the second electrode 170 . It is possible to reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the capping layer 180 may serve as a buffer for the second electrode 170 . .

A buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .

2, the organic electric device 200 according to another embodiment of the present invention is a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a capping layer 180 is formed on the second electrode. can

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , in the organic electric device 300 according to another embodiment of the present invention, there are two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, the organic electric device according to an embodiment of the present invention includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode. 170 and a capping layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 . . As described above, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.

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

When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3, an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.

The compound represented by Chemical Formula 1 of the present invention may be used as a material for the capping layer 180 .

A study on the selection of a core and a combination of sub-substituents bonded thereto, since the band gap, electrical properties, interfacial properties, etc. may vary depending on which position and which substituent is bonded even for the same and similar core In particular, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have. In addition, an auxiliary light emitting layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.

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

In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

Hereinafter, an organic electric device according to an aspect of the present invention will be described.

An organic electric device according to an embodiment of the present invention, an anode; cathode; an organic material layer formed between the anode and the cathode; and a capping layer, wherein the organic material layer includes a hole transport region, a light emitting layer and an electron transport region, the electron transport region includes an electron transport layer and an electron injection layer, and the cathode is magnesium (Mg ) and silver (Ag), wherein the ratio of silver (Ag) is 80% or more, and the capping layer includes a compound satisfying the following formula 1 at a wavelength of 450 nm.

[Equation 1]

tanδ (Loss tangent) ≤ 0.001

{In the above formula 1,

1) tanδ is ε ² /ε ¹ ,

2) ε ² is the imaginary part of the complex permittivity of the dielectric material representing the dielectric loss, expressed as 2nk,

3) ε ¹ is the real part of the complex permittivity representing the permittivity, denoted by n ² -k ² ,

4) n is the refractive index, and k is the absorption coefficient.}

In the prior art, a translucent electrode such as LiF/Al/Ag, Ca/Mg, or LiF/MgAg has been used as a cathode. However, most of them are techniques in which the Mg content is more than 80% and the Ag content is less than 20%, and the prior art that has demonstrated the relevant effect on an anode having an Ag content of 80% or more like the present invention has not yet been reported.

Therefore, the present invention confirmed through experiments that the more the Ag content is 80% or more, the better the conductivity, and the reflectance is similar to that when the Ag content is less than 20%, but the absorbance is lowered and the transmittance is increased, so that it is possible to reduce the loss of light by the cathode. , and furthermore, it was confirmed that the critical angle was increased, and consequently, the efficiency of the device could be significantly improved.

In Equation 1, the loss tangent (tan δ) is an index indicating the loss characteristics of the dielectric and is expressed as the ratio ^{of the imaginary part (ε 2} )/real part (ε ^{1 ) of the complex dielectric constant of the dielectric.} The imaginary part of the permittivity itself means the dielectric loss, and since the degree of loss varies according to the size of the real part of the permittivity, it is expressed in the same proportional expression as the imaginary part/real part.

tan δ does not mean that the δ value is taken as tangent, but is an index derived because the horizontal is real and vertical is imaginary in the multiple permittivity coordinate system. That is, the imaginary part/real part eventually becomes the ratio of vertical/horizontal and is mathematically equivalent to tangent.

Loss Tangent is an index indicating the loss characteristics of the dielectric, so the smaller the value, the better, and it is mainly used as a characteristic index for microstrip substrates or dielectric resonators.

In addition, the present invention provides an organic electric device that necessarily includes ytterbium (Ytterbium, Yb) of the lanthanum group in the electron transport region.

The higher the Ag content, the higher the transmittance and the higher the conductivity, so the efficiency is greatly improved. Therefore, it was confirmed that by using Yb with good conductivity for the electron injection layer, the existing advantages can be utilized and the disadvantages can be sufficiently overcome.

In addition, the present invention provides an organic electric device in which the capping layer compound has a refractive index of 2.1 or more at a wavelength of 450 nm, a refractive index of 1.95 or more at a wavelength of 530 nm, and a refractive index of 1.85 or more at a wavelength of 620 nm.

In addition, the present invention provides an organic electric device in which the capping layer compound has a refractive index difference of 0.08 or more at wavelengths of 430 nm and 460 nm.

In addition, the present invention provides an organic electric device in which the absorption coefficient of the capping layer compound is 0.3 or more at a wavelength of 410 nm.

In addition, the present invention provides an organic electric device in which the absorption coefficient of the capping layer compound is 0.1 or more at a wavelength of 410 nm to 430 nm.

In addition, the present invention provides an organic electric device in which the capping layer compound has an absorbance of 0.2 or more at a wavelength of 400 nm to 410 nm in an absorption spectrum of a ^{concentration of 10 - 5 mol/L.}

In addition, the present invention provides a compound for a capping layer of the organic electric device, which satisfies the following formula (1) and is represented by the following formula (1).

[Equation 1]

tanδ (Loss tangent) ≤ 0.001

{In the above formula 1,

1) tanδ is ε ² /ε ¹ ,

2) ε ² is the imaginary part of the complex permittivity of the dielectric material representing the dielectric loss, expressed as 2nk,

3) ε ¹ is the real part of the complex permittivity representing the permittivity, denoted by n ² -k ² ,

4) n is the refractive index, and k is the absorption coefficient.}

[Formula 1]

In Formula 1, each symbol may be defined as follows.

1) Ar ¹ , Ar ^{2 ,} and Ar ³ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); is selected from the group consisting of

When Ar ¹ , Ar ² and Ar ³ are aryl groups, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. can,

When Ar ¹ , Ar ² and Ar ³ are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene , pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, It may be benzofuropyrimidine, phenothiazine, phenylphenothiazine, triazine, quinoxaline, etc.;

When Ar ¹ , Ar ² and Ar ³ are fused cyclic groups, preferably a fused cyclic group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C _{30 aromatic ring, more preferably a C 3} to C ₂₄ aliphatic group. It may be a fused ring group of a ring and a C ₆ ~ C _{24 aromatic ring,}

When Ar ¹ , Ar ² and Ar ³ are an alkyl group, they are preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

2) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and combinations thereof.

When L' is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₂₄ arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc. there is,

When L' is an aliphatic ring group, it may be preferably a C ₃ ~ C ₃₀ aliphatic ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring group,

When L' is a heterocyclic group, it may be a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole. , 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, It may be phenothiazine, phenylphenothiazine, and the like.

3) wherein R _a is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And -L ⁴ Ar ⁵ ; is selected from the group consisting of,

4) wherein R _b is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and -L ⁵ Ar ⁶ ; is selected from the group consisting of.

When R _a and R _b are aryl groups, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. may be

When R _a and R _b are an aliphatic ring group, it may be preferably a C ₃ ~ C ₃₀ aliphatic ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring group,

When R _a and R _b are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, Pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuro pyrimidine, phenothiazine, phenylphenothiazine, and the like.

5) Ar ⁵ and Ar ⁶ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ Aryloxy group; is selected from the group consisting of.

When Ar ⁵ and Ar ⁶ are an aryl group, preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. may be

When Ar ⁵ and Ar ⁶ are an aliphatic ring group, preferably a C ₃ ~ C ₃₀ aliphatic ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring group,

When Ar ⁵ and Ar ⁶ are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, Pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuro pyrimidine, phenothiazine, phenylphenothiazine, and the like.

When Ar ⁵ and Ar ⁶ are an alkyl group, it is preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

6) L ¹ , L ² , L ³ , L ⁴ and L ⁵ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₂ ~ C ₆₀ A heterocyclic group is selected from the group consisting of.

When L ¹ , L ² , L ³ , L ⁴ and L ⁵ are an arylene group, preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₂₄ arylene group, for example, It may be phenylene, biphenyl, naphthalene, terphenyl, etc.;

When L ¹ , L ² , L ³ , L ⁴ and L ⁵ are a fused cyclic group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably C _It may be a fused ring group of 3 ~ C ₂₄ aliphatic ring and C ₆ ~ C _{24 aromatic ring,}

When L ¹ , L ² , L ³ , L ⁴ and L ⁵ are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, and examples Pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzo thienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ An alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ ~ C ₂₀ Aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; and -L'-N(R _a )(R _b ); 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, where 'ring' means C ₃ ~ C ₆₀ aliphatic ring or C ₆ ~ C ₆₀ aromatic ring or C ₂ ~ C _{60 It} refers to a fused ring consisting of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

In addition, the present invention provides a compound represented by the formula (1) is represented by the following formula (1-1).

[Formula 1-1]

In Formula 1-1, each symbol may be defined as follows.

1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) X is O or S;

3) Z is N or CR ^e ,

4) R ¹ and R ^e are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); and R ¹ are the same as or different from each other.

When R ¹ and R ^e are an aryl group, preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. may be

When R ¹ and R ^e are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, Pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuro It may be pyrimidine, phenothiazine, phenylphenothiazine, triazine, quinoxaline, etc.;

When R ¹ and ^Re are a fused cyclic group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring and C _It may be a fused ring group of an aromatic ring of 6 to C _24,

When R ¹ and R ^e are an alkyl group, it is preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

5) L', R _a and R _b are the same as defined in Formula 1 above,

6) a is i) ^{an integer of 0 to 4 when L 1} is bonded to *, and ii) an integer of 0 to 3 when ^{L 1 is not bonded to *.}}

In addition, the present invention provides a compound in which the compound represented by Formula 1 is represented by the following Formula 1-2 or Formula 1-3.

[Formula 1-2] [Formula 1-3]

{In Formula 1-2 or Formula 1-3,

1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) X, R ¹ and a are the same as defined in Formula 1-1.}

In addition, the present invention provides an organic electric device in which the compound represented by Formula 1 is represented by Formula 1-4 below.

[Formula 1-4]

In Formula 1-4, each symbol may be defined as follows.

1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) Y is NR, CR'R", O or S;

3) wherein R, R' and R" are each independently a C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; and at least one hetero of O, N, S, Si and P _{A C 2} ~ C ₆₀ heterocyclic group containing an atom; or selected from the group consisting of, or R' and R" are bonded to each other to C ₆ ~ C ₆₀ Aromatic hydrocarbon; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; Or C ₃ ~ C ₆₀ of the aliphatic ring and C ₆ ~ C ₆₀ of the aromatic ring fused ring group; to form.

When R, R' and R" are an alkyl group, it is preferably a C ₁ to C ₃₀ alkyl group, more preferably a C ₁ to C ₂₄ alkyl group,

When R, R' and R" are an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. there is,

When R, R' and R" are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, illustratively pyrazine, thiophene, Pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzo puropyrimidine, phenothiazine, phenylphenothiazine, triazine, quinoxaline, and the like.

When R' and R" combine with each other to form an aromatic hydrocarbon, preferably a C ₆ ~ C ₃₀ aromatic hydrocarbon, more preferably a C ₆ ~ C ₂₄ aromatic hydrocarbon may be formed,

When R' and R" combine with each other to form a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group may be formed,

When R' and R" combine with each other to form an aliphatic ring, preferably a C ₃ ~ C ₃₀ aliphatic ring, more preferably a C ₃ ~ C ₂₄ aliphatic ring may be formed,

When R' and R" combine with each other to form a fused ring group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably C ₃ - it can be fused ring date of an aromatic ring of C ₂₄ of aliphatic rings and C ₆ ~ C _24.

4) R ¹ ' and R ² ' are the ^{same as the definition of R 1} in Formula 1-1, and are the same as or different from each other,

5) a' is an integer from 0 to 4, and b' is an integer from 0 to 3.}

In addition, the present invention provides a compound in which the compound represented by Formula 1 is represented by any one of Formulas 2-1 to 2-5.

[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Formula 2-4] [Formula 2-5]

{In Formulas 2-1 to 2-5,

1) Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) X, Z, R ¹ and a are the same as defined in Formula 1-1,

3) X ¹ and X ² are the same as defined for X in Formula 1-1,

4) Y ¹ and Y ² are the same as the definition of Y in Formula 1-4,

5) Z ¹ and Z ² are the same as the definition of Z in Formula 1-1,

6) R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are the same as defined ^{for R 1 in Formula 1-1,}

7) b is i) an integer of 0 to 4 when ^{L 2} is bonded to *, ii) an integer of 0 to 3 when ^{L 2 is not bonded to *,}

8) c is i) an integer of 0 to 4 when ^{L 3} is bonded to *, ii) an integer of 0 to 3 when ^{L 3 is not bonded to *,}

9) d and f are independently integers from 0 to 3, and e and g are independently integers from 0 to 4.}

In addition, the present invention provides a compound in which the compound represented by Formula 1 is represented by Formula 2-6 or Formula 2-7.

[Formula 2-6] [Formula 2-7]

{In Formulas 2-6 to 2-7,

1) Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) Y, R ¹ ', R ² ', a' and b' are the same as defined in Formula 1-4,

3) Y ¹ and Y ² are the same as the definition of Y in Formula 1-4,

4) R ⁴ , R ⁵ , R ⁶ and R ⁷ are the same as defined ^{for R 1 in Formula 1-1,}

5) d and f are each independently an integer from 0 to 3, and e and g are each independently an integer from 0 to 4.}

In addition, the present invention provides a compound in which the compound represented by the formula (1) is represented by the following formula (3).

[Formula 3]

{In Formula 3,

1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) L ⁴ and L ⁵ are the same as the definition ^{of L 1} in Formula 1 above,

3) Ar ⁵ and Ar ⁶ are the same as defined ^{for Ar 1} in Formula 1 above.}

In addition, the present invention provides a compound in which the compound represented by Formula 1 is represented by any one of Formulas 3-1 to 3-4 below.

[Formula 3-1] [Formula 3-2]

[Formula 3-3] [Formula 3-4]

In Formulas 3-1 to 3-4, each symbol may be defined as follows.

1) Ar ² , Ar ³ , L′, L ¹ , L ² and L ³ are the same as defined in Formula 1 above,

2) L ⁴ and L ⁵ are the same as the definition ^{of L 1} in Formula 1 above,

3) Ar ⁵ and Ar ⁶ are the same as the definition ^{of Ar 1} in Formula 1 above,

4) X, Z, R ¹ and a are the same as defined in Formula 1-1,

5) Y, R ¹ ', R ² ', a' and b' are the same as defined in Formula 1-4,

6) X ^a is the same as the definition of X in Formula 1-1,

7) Y ^a is the same as the definition of Y in Formula 1-4,

8) Z ^a is the same as the definition of Z in Formula 1-1,

9) R ¹ ", R ² ", and R ³ " are the same as the definition ^{of R 1 in Formula 1-1,}

10) a is i) an integer of 0 to 4 when ^{L 2} is bonded to *, ii) an integer of 0 to 3 when ^{L 2 is not bonded to *,}

11) a", b" and c" are each independently an integer from 0 to 3.

Specifically, the compound represented by Formula 1 may be any one of the following compounds P-1 to P-175.

In addition, in the organic electric device of the present invention, the organic material layer may include two or more stacks including a hole transport region, a light emitting layer, and an electron transport region sequentially formed on the anode, and the organic material layer is formed between the two or more stacks. It may further include a charge generation layer.

In another aspect, the present invention provides a display device including the organic electric device; and a controller for driving the display device. In this case, the organic electroluminescent device may be at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for single-color or white lighting.

Hereinafter, examples of the synthesis of the compound represented by the formula according to the present invention and the preparation of the organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[ Synthesis example ]

The compound represented by Formula 1 according to the present invention (final product) may be prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto. (Hal ¹ is Br or Cl.)

<Scheme 1>

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto. (Hal ¹ is Br or Cl, Hal ² is I, Br or Cl.)

<Scheme 2>

인 경우, 하기 반응식 2-1의 반응경로에 의해 합성될 수 있으며, 또는 Sub 1의 Ar¹이 -L'-N(R_a)(R_b)인 경우, 하기 반응식 2-2의 반응경로에 의해 합성될 수 있으나, 이에 한정된 것은 아니다. (Hal¹은 Br 또는 Cl이고, Hal²는 I, Br 또는 Cl이며, R^c 및 R^d는 상기 화학식 1의 R¹ 정의와 동일하고, l 및 m은 서로 독립적으로 0 내지 3의 정수이며, L', R_a 및 R_b는 상기에서의 정의와 동일하다.)However, if Ar ¹ of Sub 1 is

In the case of , it can be synthesized by the reaction route of Scheme 2-1, or when Ar ¹ of Sub 1 is -L'-N(R _a )(R _b ), in the reaction route of Reaction Scheme 2-2 may be synthesized by, but is not limited thereto. (Hal ¹ is Br or Cl, Hal ² is I, Br or Cl, R ^c and R ^{d are the same as defined for R 1 in} Formula 1 above, and l and m are each independently an integer of 0 to 3; L', R _a and R _b are the same as defined above.)

<Reaction Scheme 2-1>

<Reaction Scheme 2-2>

1. Sub 1-3 Synthesis example

Sub a-1 (4.6 g, 28.2 mmol) was placed in a round-bottom flask and dissolved in THF (70 mL) and water (23 mL), Sub b-1 (5.9 g, 30.8 mmol), Pd(PPh ₃ ) ₄ (0.98 g, 0.9 mmol), NaOH (51.7 g, 56.4 mmol) were added and stirred at 75°C. When the reaction was complete, the reaction was _{extracted with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 3.8 g (yield: 59%) of the product.

2. Sub 1-83 Synthesis example

Sub a'-83 (13.4 g, 80.1 mmol), Sub b'-83 (21.4 g, 80.1 mmol), NaO t -Bu (23.1 g, 240.4 mmol), P( t -Bu) ₃ ( 50wt% Sol.) (1.6 mL, 4.0 mmol) was dissolved in Toluene (270 mL), and Pd ₂ (dba) ₃ (0.73 g, 0.8 mmol) was added thereto, followed by stirring at 80°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 20.7 g (yield: 73%) of the product.

3. Sub 1-118 Synthesis example

Sub a"-118 (10.8 g, 34.4 mmol) in a round-bottom flask, Sub b"-118 (5.8 g, 34.4 mmol), NaO t -Bu (9.9 g, 103.3 mmol), P( t -Bu) ₃ ( 50wt% Sol.) (0.7 mL, 1.7 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.3 mmol), and Toluene (220 mL) were added, and 8.6 g of the product (Yield: 65%) was obtained.

4. Sub 1-138 Synthesis example

Sub a-138 (8.3 g, 46.6 mmol) was placed in a round-bottom flask and dissolved in THF (125 mL) and water (41 mL), Sub b-1 (9.7 g, 50.8 mmol), Pd(PPh ₃ ) ₄ (1.6 g, 1.4 mmol) and NaOH (85.4 g, 93.3 mmol) were added, and 7.08 g (yield: 62%) of the product was obtained by using the Sub 1-3 synthesis method.

On the other hand, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 below shows Field Desorption-Mass Spectrometry (FD-MS) values of the compound belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=153.00 (C ₇ H ₄ ClNO=153.57) Sub 1-2 m/z=168.98 (C ₇ H ₄ ClNS=169.63) Sub 1-3 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-4 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-5 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-6 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-7 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-8 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-9 m/z=246.00 (C ₁₂ H ₇ ClN ₂ S=246.71) Sub 1-10 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-11 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-12 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-13 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-14 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-15 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-16 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-17 m/z=153.00 (C ₇ H ₄ ClNO=153.57) Sub 1-18 m/z=153.00 (C ₇ H ₄ ClNO=153.57) Sub 1-19 m/z=153.00 (C ₇ H ₄ ClNO=153.57) Sub 1-20 m/z=153.00 (C ₇ H ₄ ClNO=153.57) Sub 1-21 m/z=168.98 (C ₇ H ₄ ClNS=169.63) Sub 1-22 m/z=168.98 (C ₇ H ₄ ClNS=169.63) Sub 1-23 m/z=168.98 (C ₇ H ₄ ClNS=169.63) Sub 1-24 m/z=168.98 (C ₇ H ₄ ClNS=169.63) Sub 1-25 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-26 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-27 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-28 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 1-29 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-30 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-31 m/z=305.06 (C ₁₉ H ₁₂ ClNO=305.76) Sub 1-32 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-33 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-34 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-35 m/z=295.02 (C ₁₇ H ₁₀ ClNS=295.78) Sub 1-36 m/z=321.04 (C ₁₉ H ₁₂ ClNS=321.82) Sub 1-37 m/z=305.06 (C ₁₉ H ₁₂ ClNO=305.76) Sub 1-38 m/z=322.03 (C ₁₈ H ₁₁ ClN ₂ S=322.81) Sub 1-39 m/z=305.06 (C ₁₉ H ₁₂ ClNO=305.76) Sub 1-40 m/z=355.08 (C ₂₃ H ₁₄ ClNO=355.82) Sub 1-41 m/z=230.02 (C ₁₂ H ₇ ClN ₂ O=230.65) Sub 1-42 m/z=245.01 (C ₁₃ H ₈ ClNS=245.72) Sub 1-43 m/z=279.05 (C ₁₇ H ₁₀ ClNO=279.72) Sub 1-44 m/z=305.06 (C ₁₉ H ₁₂ ClNO=305.76) Sub 1-45 m/z=321.04 (C ₁₉ H ₁₂ ClNS=321.82) Sub 1-46 m/z=279.05 (C ₁₇ H ₁₀ ClNO=279.72) Sub 1-47 m/z=345.04 (C ₂₁ H ₁₂ ClNS=345.84) Sub 1-48 m/z=305.06 (C ₁₉ H ₁₂ ClNO=305.76) Sub 1-49 m/z=203.01 (C ₁₁ H ₆ ClNO=203.63) Sub 1-50 m/z=346.05 (C ₂₀ H ₁₁ ClN ₂ O ₂ =346.77) Sub 1-51 m/z=367.03 (C ₂₀ H ₁₄ ClNS ₂ =367.91) Sub 1-52 m/z=350.99 (C ₁₉ H ₁₀ ClNS ₂ =351.87) Sub 1-53 m/z=335.02 (C ₁₉ H ₁₀ ClNOS=335.81) Sub 1-54 m/z=319.04 (C ₁₉ H ₁₀ ClNO ₂ =319.74) Sub 1-55 m/z=361.07 (C ₂₂ H ₁₆ ClNS=361.89) Sub 1-56 m/z=345.09 (C ₂₂ H ₁₆ ClNO=345.83) Sub 1-57 m/z=218.00 (C ₁₂ H ₇ ClS=218.70) Sub 1-58 m/z=218.00 (C ₁₂ H ₇ ClS=218.70) Sub 1-59 m/z=218.00 (C ₁₂ H ₇ ClS=218.70) Sub 1-60 m/z=218.00 (C ₁₂ H ₇ ClS=218.70) Sub 1-61 m/z=202.02 (C ₁₂ H ₇ ClO=202.64) Sub 1-62 m/z=252.03 (C ₁₆ H ₉ ClO=252.70) Sub 1-63 m/z=252.03 (C ₁₆ H ₉ ClO=252.70) Sub 1-64 m/z=277.07 (C ₁₈ H ₁₂ ClN=277.75) Sub 1-65 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-66 m/z=228.07 (C ₁₅ H ₁₃ Cl=228.72) Sub 1-67 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-68 m/z=278.09 (C ₁₉ H ₁₅ Cl=278.78) Sub 1-69 m/z=202.02 (C ₁₂ H ₇ ClO=202.64) Sub 1-70 m/z=228.07 (C ₁₅ H ₁₃ Cl=228.72) Sub 1-71 m/z=202.02 (C ₁₂ H ₇ ClO=202.64) Sub 1-72 m/z=294.03 (C ₁₈ H ₁₁ ClS=294.80) Sub 1-73 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-74 m/z=304.1 (C ₂₁ H ₁₇ Cl=304.82) Sub 1-75 m/z=202.02 (C ₁₂ H ₇ ClO=202.64) Sub 1-76 m/z=252.03 (C ₁₆ H ₉ ClO=252.70) Sub 1-77 m/z=278.05 (C ₁₈ H ₁₁ ClO=278.74) Sub 1-78 m/z=399.08 (C ₂₅ H ₁₈ ClNS=399.94) Sub 1-79 m/z=353.1 (C ₂₄ H ₁₆ ClN=353.85) Sub 1-80 m/z=277.07 (C ₁₈ H ₁₂ ClN=277.75) Sub 1-81 m/z=278.06 (C ₁₇ H ₁₁ ClN ₂ =278.74) Sub 1-82 m/z=453.13 (C ₃₂ H ₂₀ ClN=453.97) Sub 1-83 m/z=353.1 (C ₂₄ H ₁₆ ClN=353.85) Sub 1-84 m/z=277.07 (C ₁₈ H ₁₂ ClN=277.75) Sub 1-85 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-86 m/z=383.05 (C ₂₄ H ₁₄ ClNS=383.89) Sub 1-87 m/z=294.03 (C ₁₈ H ₁₁ ClS=294.80) Sub 1-88 m/z=294.03 (C ₁₈ H ₁₁ ClS=294.80) Sub 1-89 m/z=294.03 (C ₁₈ H ₁₁ ClS=294.80) Sub 1-90 m/z=344.04 (C ₂₂ H ₁₃ ClS=344.86) Sub 1-91 m/z=252.03 (C ₁₆ H ₉ ClO=252.70) Sub 1-92 m/z=394.06 (C ₂₆ H ₁₅ ClS=394.92) Sub 1-93 m/z=344.04 (C ₂₂ H ₁₃ ClS=344.86) Sub 1-94 m/z=350.09 (C ₂₅ H ₁₅ Cl=350.85) Sub 1-95 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-96 m/z=228.07 (C ₁₅ H ₁₃ Cl=228.72) Sub 1-97 m/z=228.07 (C ₁₅ H ₁₃ Cl=228.72) Sub 1-98 m/z=428.13 (C ₃₁ H ₂₁ Cl=428.96) Sub 1-99 m/z=350.09 (C ₂₅ H ₁₅ Cl=350.85) Sub 1-100 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-101 m/z=350.09 (C ₂₅ H ₁₅ Cl=350.85) Sub 1-102 m/z=400.10 (C ₂₉ H ₁₇ Cl=400.91) Sub 1-103 m/z=400.10 (C ₂₉ H ₁₇ Cl=400.91) Sub 1-104 m/z=400.10 (C ₂₉ H ₁₇ Cl=400.91) Sub 1-105 m/z=400.10 (C ₂₉ H ₁₇ Cl=400.91) Sub 1-106 m/z=384.16 (C ₂₇ H ₂₅ Cl=384.95) Sub 1-107 m/z=290.09 (C ₂₀ H ₁₅ Cl=290.79) Sub 1-108 m/z=469.12 (C ₃₂ H ₂₀ ClNO=469.97) Sub 1-109 m/z=278.05 (C ₁₈ H ₁₁ ClO=278.74) Sub 1-110 m/z=252.03 (C ₁₆ H ₉ ClO=252.70) Sub 1-111 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-112 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-113 m/z=302.05 (C ₂₀ H ₁₁ ClO=302.76) Sub 1-114 m/z=268.01 (C ₁₆ H ₉ ClS=268.76) Sub 1-115 m/z=394.06 (C ₂₆ H ₁₅ ClS=394.92) Sub 1-116 m/z=302.05 (C ₂₀ H ₁₁ ClO=302.76) Sub 1-117 m/z=344.04 (C ₂₂ H ₁₃ ClS=344.86) Sub 1-118 m/z=385.07 (C ₂₄ H ₁₆ ClNS=385.91) Sub 1-119 m/z=385.07 (C ₂₄ H ₁₆ ClNS=385.91) Sub 1-120 m/z=472.13 (C ₃₁ H ₂₁ ClN ₂ O=472.97) Sub 1-121 m/z=548.17 (C ₃₇ H ₂₅ ClN ₂ O=549.07) Sub 1-122 m/z=502.09 (C ₃₁ H ₁₉ ClN ₂ OS=503.02) Sub 1-123 m/z=502.09 (C ₃₁ H ₁₉ ClN ₂ OS=503.02) Sub 1-124 m/z=369.09 (C ₂₄ H ₁₆ ClNO=369.85) Sub 1-125 m/z=567.09 (C ₃₆ H ₂₂ ClNS ₂ =568.15) Sub 1-126 m/z=445.12 (C ₃₀ H ₂₀ ClNO=445.95) Sub 1-127 m/z=495.14 (C ₃₄ H ₂₂ ClNO=496.01) Sub 1-128 m/z=472.13 (C ₃₁ H ₂₁ ClN ₂ O=472.97) Sub 1-129 m/z=552.11 (C ₃₅ H ₂₁ ClN ₂ OS=553.08) Sub 1-130 m/z=461.10 (C ₃₀ H ₂₀ ClNS=462.01) Sub 1-131 m/z=559.06 (C ₃₂ H ₁₈ ClN ₃ OS ₂ =560.09) Sub 1-132 m/z=559.06 (C ₃₂ H ₁₈ ClN ₃ OS ₂ =560.09) Sub 1-133 m/z=593.10 (C ₃₆ H ₂₀ ClN ₃ O ₂ S=594.09) Sub 1-134 m/z=437.09 (C ₂₆ H ₁₆ ClN ₃ O ₂ =437.88) Sub 1-135 m/z=554.11 (C ₃₃ H ₁₉ ClN ₄ S ₃ =554.99) Sub 1-136 m/z=242.99 (C ₁₃ H ₆ ClNS=243.71) Sub 1-137 m/z=249.99 (C ₁₂ H ₇ ClO ₂ S=250.70) Sub 1-138 m/z=244.01 (C ₁₄ H ₉ ClS=244.74) Sub 1-139 m/z=228.03 (C ₁₄ H ₉ ClO=228.68) Sub 1-140 m/z=502.09 (C ₃₁ H ₁₉ ClN ₂ OS=503.02)

II. Synthesis of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto. (Hal ³ is Br or Cl.)

<Scheme 3>

1. Sub 2-11 Synthesis example

Sub c-1 (23.65 g, 101.46 mmol) as a starting material, Sub d-1 (10.39 g, 111.60 mmol), Pd ₂ (dba) ₃ (2.79 g, 3.04 mmol), 50% P( t -Bu) ₃ (2.5 mL, 6.09 mmol), NaO t -Bu (29.25 g, 304.38 mmol), Toluene (710 mL) were added and stirred at 80°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 20.66 g (yield: 83%) of the product.

2. Sub 2-23 Synthesis example

Sub c-2 (15.7 g, 54.1 mmol) as a starting material, Sub d-2 (7.8 g, 54.1 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.62 mmol), 50% P( t -Bu) ₃ (1.3 mL, 3.25 mmol), NaO t -Bu (15.6 g, 162.31 mmol), and Toluene (200 mL) were added, and 15.26 g (yield: 80%) of the product was obtained using the Sub 2-11 synthesis method.

3. Sub 2-91 Synthesis example

Sub c-3 (12.5 g, 50.6 mmol) as a starting material, Sub d-3 (10.6 g, 50.6 mmol), Pd ₂ (dba) ₃ (1.4 g, 1.52 mmol), 50% P( t -Bu) ₃ (1.2 mL, 3.04 mmol), NaO t- Bu (14.6 g, 151.8 mmol), and Toluene (200 mL) were added, and 14.85 g (yield: 78%) of the product was obtained using the Sub 2-11 synthesis method.

4. Sub 2-196 Synthesis example

Sub c-4 (14.3 g, 54.3 mmol) as a starting material, Sub d-4 (12.2 g, 54.3 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.63 mmol), 50% P( t -Bu) ₃ (1.3 mL, 3.26 mmol), NaO t- Bu (15.7 g, 163.0 mmol), and Toluene (280 mL) were added, and 14.85 g (yield: 78%) of the product was obtained using the Sub 2-11 synthesis method.

On the other hand, the compound belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 below shows FD-MS values of the compounds belonging to Sub 2 .

compound FD-MS compound FD-MS Sub 2-1 m/z=169.09 (C ₁₂ H ₁₁ N=169.23) Sub 2-2 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-3 m/z=371.17 (C ₂₈ H ₂₁ N=371.48) Sub 2-4 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub 2-5 m/z=371.17 (C ₂₈ H ₂₁ N=371.48) Sub 2-6 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-7 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-8 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 2-9 m/z=371.17 (C ₂₈ H ₂₁ N=371.48) Sub 2-10 m/z=319.14 (C ₂₄ H ₁₇ N=319.41) Sub 2-11 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-12 m/z=371.17 (C ₂₈ H ₂₁ N=371.48) Sub 2-13 m/z=322.15 (C ₂₃ H ₁₈ N ₂ =322.41) Sub 2-14 m/z=373.16 (C ₂₆ H ₁₉ N ₃ =373.46) Sub 2-15 m/z=174.12 (C ₁₂ H ₆ D ₅ N=174.26) Sub 2-16 m/z=325.13 (C ₂₀ H ₁₅ N ₅ =325.38) Sub 2-17 m/z=412.19 (C ₃₀ H ₂₄ N ₂ =412.54) Sub 2-18 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-19 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-20 m/z=210.08 (C ₁₃ H ₁₀ N ₂ O=210.24) Sub 2-21 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) Sub 2-22 m/z=352.10 (C ₂₃ H ₁₆ N ₂ S=352.46) Sub 2-23 m/z=352.10 (C ₂₃ H ₁₆ N ₂ S=352.46) Sub 2-24 m/z=402.12 (C ₂₇ H ₁₈ N ₂ S=402.52) Sub 2-25 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-26 m/z=373.16 (C ₂₆ H ₁₉ N ₃ =373.46) Sub 2-27 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) Sub 2-28 m/z=302.09 (C ₁₉ H ₁₄ N ₂ S=302.40) Sub 2-29 m/z=435.09 (C ₂₆ H ₁₇ N ₃ S ₂ =435.56) Sub 2-30 m/z=419.11 (C ₂₆ H ₁₇ N ₃ OS=419.50) Sub 2-31 m/z=403.13 (C ₂₆ H ₁₇ N ₃ O ₂ =403.44) Sub 2-32 m/z=286.11 (C ₁₉ H ₁₄ N ₂ O=286.33) Sub 2-33 m/z=302.09 (C ₁₉ H ₁₄ N ₂ S=302.40) Sub 2-34 m/z=435.09 (C ₂₆ H ₁₇ N ₃ S ₂ =435.56) Sub 2-35 m/z=485.10 (C ₃₀ H ₁₉ N ₃ S ₂ =485.62) Sub 2-36 m/z=469.12 (C ₃₀ H ₁₉ N ₃ OS=469.56) Sub 2-37 m/z=419.11 (C ₂₆ H ₁₇ N ₃ OS=419.50) Sub 2-38 m/z=403.13 (C ₂₆ H ₁₇ N ₃ O ₂ =403.44) Sub 2-39 m/z=403.13 (C ₂₆ H ₁₇ N ₃ O ₂ =403.44) Sub 2-40 m/z=345.15 (C ₂₆ H ₁₉ N=345.45) Sub 2-41 m/z=210.08 (C ₁₃ H ₁₀ N ₂ O=210.24) Sub 2-42 m/z=286.11 (C ₁₉ H ₁₄ N ₂ O=286.33) Sub 2-43 m/z=276.07 (C ₁₇ H ₁₂ N ₂ S=276.36) Sub 2-44 m/z=260.09 (C ₁₇ H ₁₂ N ₂ O=260.30) Sub 2-45 m/z=378.12 (C ₂₅ H ₁₈ N ₂ S=378.49) Sub 2-46 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) Sub 2-47 m/z=428.13 (C ₂₉ H ₂₀ N ₂ S=428.55) Sub 2-48 m/z=412.16 (C ₂₉ H ₂₀ N ₂ O=412.49) Sub 2-49 m/z=428.13 (C ₂₉ H ₂₀ N ₂ S=428.55) Sub 2-50 m/z=419.11 (C ₂₆ H ₁₇ N ₃ OS=419.50) Sub 2-51 m/z=327.10 (C ₂₀ H ₁₃ N ₃ O ₂ =327.34) Sub 2-52 m/z=343.08 (C ₂₀ H ₁₃ N ₃ OS=343.4) Sub 2-53 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-54 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-55 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 2-56 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 2-57 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 2-58 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub 2-59 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub 2-60 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-61 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-62 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 2-63 m/z=326.09 (C ₂₁ H ₁₄ N ₂ S=326.42) Sub 2-64 m/z=419.11 (C ₂₆ H ₁₇ N ₃ OS=419.50) Sub 2-65 m/z=442.11 (C ₂₉ H ₁₈ N ₂ OS=442.54) Sub 2-66 m/z=458.09 (C ₂₉ H ₁₈ N ₂ S ₂ =458.60) Sub 2-67 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 2-68 m/z=466.15 (C ₃₂ H ₂₂ N ₂ S=466.60) Sub 2-69 m/z=542.18 (C ₃₈ H ₂₆ N ₂ S=542.70) Sub 2-70 m/z=359.06 (C ₂₀ H ₁₃ N ₃ S ₂ =359.47) Sub 2-71 m/z=267.05 (C ₁₄ H ₉ N ₃ OS=267.31) Sub 2-72 m/z=392.13 (C ₂₆ H ₂₀ N ₂ S=392.52) Sub 2-73 m/z=376.16 (C ₂₆ H ₂₀ N ₂ O=376.46) Sub 2-74 m/z=391.14 (C ₂₇ H ₂₁ NS=391.53) Sub 2-75 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-76 m/z=418.15 (C ₂₈ H ₂₂ N ₂ S=418.56) Sub 2-77 m/z=381.06 (C ₂₄ H ₁₅ NS ₂ =381.51) Sub 2-78 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-79 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-80 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-81 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-82 m/z=392.10 (C ₂₅ H ₁₆ N ₂ OS=392.48) Sub 2-83 m/z=381.06 (C ₂₄ H ₁₅ NS ₂ =381.51) Sub 2-84 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-85 m/z=349.11 (C ₂₄ H ₁₅ NO ₂ =349.39) Sub 2-86 m/z=392.10 (C ₂₅ H ₁₆ N ₂ OS=392.48) Sub 2-87 m/z=469.12 (C ₃₀ H ₁₉ N ₃ OS=469.56) Sub 2-88 m/z=517.16 (C ₃₅ H ₂₃ N ₃ S=517.65) Sub 2-89 m/z=451.17 (C ₃₁ H ₂₁ N ₃ O=451.53) Sub 2-90 m/z=403.13 (C ₂₆ H ₁₇ N ₃ O ₂ =403.44) Sub 2-91 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub 2-92 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub 2-93 m/z=366.08 (C ₂₃ H ₁₄ N ₂ OS=366.44) Sub 2-94 m/z=442.11 (C ₂₉ H ₁₈ N ₂ OS=442.54) Sub 2-95 m/z=495.14 (C ₃₂ H ₂₁ N ₃ OS=495.6) Sub 2-96 m/z=484.11 (C ₃₁ H ₂₀ N ₂ S ₂ =484.64) Sub 2-97 m/z=392.10 (C ₂₅ H ₁₆ N ₂ OS=392.48) Sub 2-98 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) Sub 2-99 m/z=431.08 (C ₂₈ H ₁₇ NS ₂ =431.57) Sub 2-100 m/z=442.11 (C ₂₉ H ₁₈ N ₂ OS=442.54) Sub 2-101 m/z=349.11 (C ₂₄ H ₁₅ NO ₂ =349.39) Sub 2-102 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub 2-103 m/z=399.13 (C ₂₈ H ₁₇ NO ₂ =399.45) Sub 2-104 m/z=426.14 (C ₂₉ H ₁₈ N ₂ O ₂ =426.48) Sub 2-105 m/z=381.06 (C ₂₄ H ₁₅ NS ₂ =381.51) Sub 2-106 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) Sub 2-107 m/z=484.11 (C ₃₁ H ₂₀ N ₂ S ₂ =484.64) Sub 2-108 m/z=478.20 (C ₃₄ H ₂₆ N ₂ O=478.60) Sub 2-109 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) Sub 2-110 m/z=572.17 (C ₃₇ H ₂₄ N ₄ OS=572.69) Sub 2-111 m/z=485.10 (C ₃₀ H ₁₉ N ₃ S ₂ =485.62) Sub 2-112 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) Sub 2-113 m/z=418.11 (C ₂₇ H ₁₈ N ₂ OS=418.51) Sub 2-114 m/z=312.13 (C ₂₁ H ₁₆ N ₂ O=312.37) Sub 2-115 m/z=488.19 (C ₃₅ H ₂₄ N ₂ O=488.59) Sub 2-116 m/z=486.21 (C ₃₆ H ₂₆ N ₂ =486.62) Sub 2-117 m/z=450.21 (C ₃₃ H ₂₆ N ₂ =450.59) Sub 2-118 m/z=418.15 (C ₂₈ H ₂₂ N ₂ S=418.56) Sub 2-119 m/z=467.15 (C ₃₁ H ₂₁ N ₃ S=467.59) Sub 2-120 m/z=501.18 (C ₃₅ H ₂₃ N ₃ O=501.59) Sub 2-121 m/z=452.16 (C ₃₀ H ₂₀ N ₄ O=452.52) Sub 2-122 m/z=557.16 (C ₃₇ H ₂₃ N ₃ OS=557.67) Sub 2-123 m/z=573.13 (C ₃₇ H ₂₃ N ₃ S ₂ =573.73) Sub 2-124 m/z=586.24 (C ₄₄ H ₃₀ N ₂ =586.74) Sub 2-125 m/z=363.14 (C ₂₄ H ₁₇ N ₃ O=363.42) Sub 2-126 m/z=574.24 (C ₄₃ H ₃₀ N ₂ =574.73) Sub 2-127 m/z=410.18 (C ₃₀ H ₂₂ N ₂ =410.52) Sub 2-128 m/z=450.21 (C ₃₃ H ₂₆ N ₂ =450.59) Sub 2-129 m/z=524.14 (C ₃₄ H ₂₄ N ₂ S ₂ =524.70) Sub 2-130 m/z=530.15 (C ₃₆ H ₂₂ N ₂ OS=530.65) Sub 2-131 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub 2-132 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub 2-133 m/z=286.11 (C ₁₉ H ₁₄ N ₂ O=286.33) Sub 2-134 m/z=534.12 (C ₃₅ H ₂₂ N ₂ S ₂ =534.70) Sub 2-135 m/z=458.09 (C ₂₉ H ₁₈ N ₂ S ₂ =458.6) Sub 2-136 m/z=457.10 (C ₃₀ H ₁₉ NS ₂ =457.61) Sub 2-137 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) Sub 2-138 m/z=484.11 (C ₃₁ H ₂₀ N ₂ S ₂ =484.64) Sub 2-139 m/z=533.13 (C ₃₆ H ₂₃ NS ₂ =533.71) Sub 2-140 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) Sub 2-141 m/z=502.17 (C ₃₅ H ₂₂ N ₂ O ₂ =502.57) Sub 2-142 m/z=517.15 (C ₃₆ H ₂₃ NOS=517.65) Sub 2-143 m/z=401.12 (C ₂₈ H ₁₉ NS=401.53) Sub 2-144 m/z=451.14 (C ₃₂ H ₂₁ NS=451.59) Sub 2-145 m/z=639.20 (C ₄₇ H ₂₉ NS=639.82) Sub 2-146 m/z=518.15 (C ₃₅ H ₂₂ N ₂ OS=518.63) Sub 2-147 m/z=524.19 (C ₃₈ H ₂₄ N ₂ O=524.62) Sub 2-148 m/z=415.1 (C ₂₈ H ₁₇ NOS=415.51) Sub 2-149 m/z=425.18 (C ₃₁ H ₂₃ NO=425.53) Sub 2-150 m/z=401.21 (C ₃₀ H ₂₇ N=401.55) Sub 2-151 m/z=494.18 (C ₃₄ H ₂₆ N ₂ S=494.66) Sub 2-152 m/z=401.21 (C ₃₀ H ₂₇ N=401.55) Sub 2-153 m/z=485.21 (C ₃₇ H ₂₇ N=485.63) Sub 2-154 m/z=523.23 (C ₄₀ H ₂₉ N=523.68) Sub 2-155 m/z=452.19 (C ₃₂ H ₂₄ N ₂ O=452.56) Sub 2-156 m/z=574.20 (C ₄₂ H ₂₆ N ₂ O=574.68) Sub 2-157 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) Sub 2-158 m/z=642.21 (C ₄₆ H ₃₀ N ₂ S=642.82) Sub 2-159 m/z=647.26 (C ₅₀ H ₃₃ N=647.82) Sub 2-160 m/z=600.22 (C ₄₄ H ₂₈ N ₂ O=600.72) Sub 2-161 m/z=563.17 (C ₄₁ H ₂₅ NS=563.72) Sub 2-162 m/z=498.17 (C ₃₆ H ₂₂ N ₂ O=498.59) Sub 2-163 m/z=697.28 (C ₅₄ H ₃₅ N=697.88) Sub 2-164 m/z=533.21 (C ₄₁ H ₂₇ N=533.67) Sub 2-165 m/z=573.25 (C ₄₄ H ₃₁ N=573.74) Sub 2-166 m/z=548.19 (C ₄₀ H ₂₄ N ₂ O=548.65) Sub 2-167 m/z=376.16 (C ₂₆ H ₂₀ N ₂ O=376.46) Sub 2-168 m/z=515.17 (C ₃₇ H ₂₅ NS=515.67) Sub 2-169 m/z=415.17 (C ₃₀ H ₂₂ FN=415.51) Sub 2-170 m/z=508.16 (C ₃₄ H ₂₄ N ₂ OS=508.64) Sub 2-171 m/z=526.20 (C ₃₈ H ₂₆ N ₂ O=526.64) Sub 2-172 m/z=476.13 (C ₃₃ H ₂₀ N ₂ S=476.60) Sub 2-173 m/z=465.12 (C ₃₂ H ₁₉ NOS=465.57) Sub 2-174 m/z=541.07 (C ₃₂ H ₁₉ N ₃ S ₃ =541.71) Sub 2-175 m/z=569.17 (C ₃₈ H ₂₃ N ₃ O ₃ =569.62) Sub 2-176 m/z=465.12 (C ₃₂ H ₁₉ NOS=465.57) Sub 2-177 m/z=481.10 (C ₃₂ H ₁₉ NS ₂ =481.63) Sub 2-178 m/z=449.14 (C ₃₂ H ₁₉ NO ₂ =449.51) Sub 2-179 m/z=381.06 (C ₂₄ H ₁₅ NS ₂ =381.51) Sub 2-180 m/z=401.12 (C ₂₈ H ₁₉ NS=401.53) Sub 2-181 m/z=415.10 (C ₂₈ H ₁₇ NOS=415.51) Sub 2-182 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-183 m/z=481.10 (C ₃₂ H ₁₉ NS ₂ =481.63) Sub 2-184 m/z=431.08 (C ₂₈ H ₁₇ NS ₂ =431.57) Sub 2-185 m/z=431.08 (C ₂₈ H ₁₇ NS ₂ =431.57) Sub 2-186 m/z=457.10 (C ₃₀ H ₁₉ NS ₂ =457.61) Sub 2-187 m/z=507.11 (C ₃₄ H ₂₁ NS ₂ =507.67) Sub 2-188 m/z=442.11 (C ₂₉ H ₁₈ N ₂ OS=442.54) Sub 2-189 m/z=559.17 (C ₃₇ H ₂₅ N ₃ OS=559.69) Sub 2-190 m/z=392.10 (C ₂₅ H ₁₆ N ₂ OS=392.48) Sub 2-191 m/z=559.17 (C ₃₇ H ₂₅ N ₃ OS=559.69) Sub 2-192 m/z=529.22 (C ₃₇ H ₂₇ N ₃ O=529.64) Sub 2-193 m/z=605.25 (C ₄₃ H ₃₁ N ₃ O=605.74) Sub 2-194 m/z=559.17 (C ₃₇ H ₂₅ N ₃ OS=559.69) Sub 2-195 m/z=559.17 (C ₃₇ H ₂₅ N ₃ OS=559.69) Sub 2-196 m/z=407.08 (C ₂₆ H ₁₇ NS ₂ =407.55) Sub 2-197 m/z=418.11 (C ₂₇ H ₁₈ N ₂ OS=418.51) Sub 2-198 m/z=433.10 (C ₂₈ H ₁₉ NS ₂ =433.59) Sub 2-199 m/z=417.12 (C ₂₈ H ₁₉ NOS=417.53) Sub 2-200 m/z=483.11 (C ₃₂ H ₂₁ NS ₂ =483.65) Sub 2-201 m/z=457.10 (C ₃₀ H ₁₉ NS ₂ =457.61) Sub 2-202 m/z=416.10 (C ₂₇ H ₁₆ N ₂ OS=416.50) Sub 2-203 m/z=424.09 (C ₂₅ H ₁₆ N ₂ O ₃ S=424.47) Sub 2-204 m/z=499.17 (C ₃₅ H ₂₁ N ₃ O=499.57) Sub 2-205 m/z=323.08 (C ₂₂ H ₁₃ NS=323.41)

III. Synthesis of final products

1. P-2 Synthesis example

After dissolving Sub 1-1 (8.8 g, 57.3 mmol) in Toluene (170 mL) in a round-bottom flask, Sub 2-2 (18.4 g, 57.3 mmol), Pd ₂ (dba) ₃ (1.57 g, 1.7 mmol) , P( t -Bu) ₃ (50wt% Sol.) (1.4 mL, 3.4 mmol), NaO t -Bu (16.5 g, 171.9 mmol) were added and stirred at 110°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was purified by silicagel column and sublimation to obtain 19.1 g (yield: 76%) of the product.

2. P-38 Synthesis example

Sub 1-8 (8.0 g, 28.8 mmol) to Sub 2-30 (12.1 g, 28.8 mmol), Pd ₂ (dba) ₃ (0.8 g, 0.86 mmol), NaO t -Bu (8.3 g, 86.4 mmol), P( t -Bu) ₃ (50wt% Sol.) (0.7 mL, 1.7 mmol) and Toluene (160 mL) were used for the above synthesis of P-2 to obtain 13.04 g (yield: 72%) of the product.

3. P-154 Synthesis example

Sub 1-118 (10.2 g, 26.4 mmol) to Sub 2-190 (10.4 g, 26.4 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol), NaO t -Bu (7.6 g, 79.3 mmol), P( t -Bu) ₃ (50wt% Sol.) (0.6 mL, 1.6 mmol) and Toluene (200 mL) were used for the above synthesis of P-2 to obtain 14.7 g (yield: 75%) of the product.

4. P-174 Synthesis example

Sub 1-138 (9.5 g, 38.8 mmol) to Sub 2-202 (162 g, 38.8 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), NaO t -Bu (11.2 g, 116.5 mmol), P( t -Bu) ₃ (50wt% Sol.) (0.9 mL, 2.3 mmol) and Toluene (200 mL) were used for the above synthesis of P-2 to obtain 19.4 g (yield: 80%) of the product.

On the other hand, the FD-MS values of the compounds P-1 to P-175 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=286.11 (C ₁₉ H ₁₄ N ₂ O=286.33) P-2 m/z=438.17 (C ₃₁ H ₂₂ N ₂ O=438.53) P-3 m/z=488.19 (C ₃₅ H ₂₄ N ₂ O=488.59) P-4 m/z=412.16 (C ₂₉ H ₂₀ N ₂ O=412.49) P-5 m/z=488.19 (C ₃₅ H ₂₄ N ₂ O=488.59) P-6 m/z=386.14 (C ₂₇ H ₁₈ N ₂ O=386.45) P-7 m/z=386.14 (C ₂₇ H ₁₈ N ₂ O=386.45) P-8 m/z=486.17 (C ₃₅ H ₂₂ N ₂ O=486.57) P-9 m/z=488.19 (C ₃₅ H ₂₄ N ₂ O=488.59) P-10 m/z=436.16 (C ₃₁ H ₂₀ N ₂ O=436.51) P-11 m/z=454.15 (C ₃₁ H ₂₂ N ₂ S=454.59) P-12 m/z=378.12 (C ₂₅ H ₁₈ N ₂ S=378.49) P-13 m/z=504.17 (C ₃₅ H ₂₄ N ₂ S=504.65) P-14 m/z=455.15 (C ₃₀ H ₂₁ N ₃ S=455.58) P-15 m/z=506.16 (C ₃₃ H ₂₂ N ₄ S=506.63) P-16 m/z=307.12 (C ₁₉ H ₉ D ₅ N ₂ S=307.43) P-17 m/z=458.13 (C ₂₇ H ₁₈ N ₆ S=458.54) P-18 m/z=545.19 (C ₃₇ H ₂₇ N ₃ S=545.70) P-19 m/z=454.15 (C ₃₁ H ₂₂ N ₂ S=454.59) P-20 m/z=438.17 (C ₃₁ H ₂₂ N ₂ O=438.53) P-21 m/z=327.10 (C ₂₀ H ₁₃ N ₃ O ₂ =327.34) P-22 m/z=479.16 (C ₃₂ H ₂₁ N ₃ O ₂ =479.54) P-23 m/z=469.12 (C ₃₀ H ₁₉ N ₃ OS=469.56) P-24 m/z=469.12 (C ₃₀ H ₁₉ N ₃ OS=469.56) P-25 m/z=519.14 (C ₃₄ H ₂₁ N ₃ OS=519.62) P-26 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) P-27 m/z=514.20 (C ₃₇ H ₂₆ N ₂ O=514.63) P-28 m/z=564.22 (C ₄₁ H ₂₈ N ₂ O=564.69) P-29 m/z=554.18 (C ₃₉ H ₂₆ N ₂ S=554.71) P-30 m/z=580.20 (C ₄₁ H ₂₈ N ₂ S=580.75) P-31 m/z=530.18 (C ₃₇ H ₂₆ N ₂ S=530.69) P-32 m/z=455.15 (C ₃₀ H ₂₁ N ₃ S=455.58) P-33 m/z=490.18 (C ₃₃ H ₂₂ N ₄ O=490.57) P-34 m/z=581.19 (C ₄₀ H ₂₇ N ₃ S=581.74) P-35 m/z=555.19 (C ₃₈ H ₂₅ N ₃ O ₂ =555.64) P-36 m/z=511.12 (C ₃₂ H ₂₁ N ₃ S ₂ =511.66) P-37 m/z=644.12 (C ₃₉ H ₂₄ N ₄ S ₃ =644.83) P-38 m/z=628.14 (C ₃₉ H ₂₄ N ₄ OS ₂ =628.77) P-39 m/z=612.16 (C ₃₉ H ₂₄ N ₄ O ₂ S=612.71) P-40 m/z=596.18 (C ₃₉ H ₂₄ N ₄ O ₃ =596.65) P-41 m/z=495.14 (C ₃₂ H ₂₁ N ₃ OS=495.60) P-42 m/z=644.12 (C ₃₉ H ₂₄ N ₄ S ₃ =644.83) P-43 m/z=678.15 (C ₄₃ H ₂₆ N ₄ OS ₂ =678.83) P-44 m/z=612.16 (C ₃₉ H ₂₄ N ₄ O ₂ S=612.71) P-45 m/z=596.18 (C ₃₉ H ₂₄ N ₄ O ₃ =596.65) P-46 m/z=286.11 (C ₁₉ H ₁₄ N ₂ O=286.33) P-47 m/z=438.17 (C ₃₁ H ₂₂ N ₂ O=438.53) P-48 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) P-49 m/z=412.16 (C ₂₉ H ₂₀ N ₂ O=412.49) P-50 m/z=488.19 (C ₃₅ H ₂₄ N ₂ O=488.59) P-51 m/z=478.15 (C ₃₃ H ₂₂ N ₂ S=478.61) P-52 m/z=402.12 (C ₂₇ H ₁₈ N ₂ S=402.52) P-53 m/z=502.15 (C ₃₅ H ₂₂ N ₂ S=502.64) P-54 m/z=504.17 (C ₃₅ H ₂₄ N ₂ S=504.65) P-55 m/z=528.17 (C ₃₇ H ₂₄ N ₂ S=528.67) P-56 m/z=327.10 (C ₂₀ H ₁₃ N ₃ O ₂ =327.34) P-57 m/z=479.16 (C ₃₂ H ₂₁ N ₃ O ₂ =479.54) P-58 m/z=485.10 (C ₃₀ H ₁₉ N ₃ S ₂ =485.62) P-59 m/z=485.10 (C ₃₀ H ₁₉ N ₃ S ₂ =485.62) P-60 m/z=519.14 (C ₃₄ H ₂₁ N ₃ OS=519.62) P-61 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) P-62 m/z=514.20 (C ₃₇ H ₂₆ N ₂ O=514.63) P-63 m/z=564.22 (C ₄₁ H ₂₈ N ₂ O=564.69) P-64 m/z=554.18 (C ₃₉ H ₂₆ N ₂ S=554.71) P-65 m/z=504.17 (C ₃₅ H ₂₄ N ₂ S=504.65) P-66 m/z=438.17 (C ₃₁ H ₂₂ N ₂ O=438.53) P-67 m/z=571.17 (C ₃₈ H ₂₅ N ₃ OS=571.70) P-68 m/z=621.19 (C ₄₂ H ₂₇ N ₃ OS=621.76) P-69 m/z=687.18 (C ₄₆ H ₂₉ N ₃ S ₂ =687.88) P-70 m/z=536.13 (C ₃₃ H ₂₀ N ₄ O ₂ S=536.61) P-71 m/z=392.10 (C ₂₅ H ₁₆ N ₂ OS=392.48) P-72 m/z=408.08 (C ₂₅ H ₁₆ N ₂ S ₂ =408.54) P-73 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) P-74 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) P-75 m/z=468.13 (C ₃₁ H ₂₀ N ₂ OS=468.57) P-76 m/z=451.17 (C ₃₁ H ₂₁ N ₃ O=451.53) P-77 m/z=502.17 (C ₃₅ H ₂₂ N ₂ O ₂ =502.57) P-78 m/z=426.14 (C ₂₉ H ₁₈ N ₂ O ₂ =426.48) P-79 m/z=442.11 (C ₂₉ H ₁₈ N ₂ OS=442.54) P-80 m/z=544.16 (C ₃₇ H ₂₄ N ₂ OS=544.67) P-81 m/z=459.09 (C ₂₈ H ₁₇ N ₃ S ₂ =459.59) P-82 m/z=651.14 (C ₄₂ H ₂₅ N ₃ OS ₂ =651.8) P-83 m/z=494.18 (C ₃₄ H ₂₆ N ₂ S=494.66) P-84 m/z=675.18 (C ₄₅ H ₂₉ N ₃ S ₂ =675.87) P-85 m/z=509.16 (C ₃₃ H ₂₃ N ₃ OS=509.63) P-86 m/z=600.17 (C ₄₀ H ₂₈ N ₂ S ₂ =600.80) P-87 m/z=590.09 (C ₃₇ H ₂₂ N ₂ S ₃ =590.78) P-88 m/z=574.12 (C ₃₇ H ₂₂ N ₂ OS ₂ =574.72) P-89 m/z=590.09 (C ₃₇ H ₂₂ N ₂ S ₃ =590.78) P-90 m/z=558.14 (C ₃₇ H ₂₂ N ₂ O ₂ S=558.66) P-91 m/z=710.21 (C ₄₈ H ₃₀ N ₄ OS=710.86) P-92 m/z=585.15 (C ₃₈ H ₂₃ N ₃ O ₂ S=585.68) P-93 m/z=575.11 (C ₃₆ H ₂₁ N ₃ OS ₂ =575.70) P-94 m/z=677.16 (C ₄₄ H ₂₇ N ₃ OS ₂ =677.84) P-95 m/z=661.18 (C ₄₄ H ₂₇ N ₃ O ₂ S=661.78) P-96 m/z=624.13 (C ₄₁ H ₂₄ N ₂ OS ₂ =624.78) P-97 m/z=542.16 (C ₃₇ H ₂₂ N ₂ O ₃ =542.59) P-98 m/z=592.18 (C ₄₁ H ₂₄ N ₂ O ₃ =592.65) P-99 m/z=590.09 (C ₃₇ H ₂₂ N ₂ S ₃ =590.78) P-100 m/z=693.14 (C ₄₄ H ₂₇ N ₃ S ₃ =693.90) P-101 m/z=671.26 (C ₄₇ H ₃₃ N ₃ O ₂ =671.80) P-102 m/z=544.16 (C ₃₇ H ₂₄ N ₂ OS=544.67) P-103 m/z=754.19 (C ₄₉ H ₃₀ N ₄ OS ₂ =754.93) P-104 m/z=611.17 (C ₄₀ H ₂₅ N ₃ O ₂ S=611.72) P-105 m/z=670.21 (C ₄₇ H ₃₀ N ₂ OS=670.83) P-106 m/z=695.24 (C ₄₉ H ₃₃ N ₃ S=695.88) P-107 m/z=659.24 (C ₄₆ H ₃₃ N ₃ S=659.85) P-108 m/z=694.24 (C ₄₈ H ₃₀ N ₄ O ₂ =694.79) P-109 m/z=766.19 (C ₅₀ H ₃₀ N ₄ OS ₂ =766.94) P-110 m/z=780.29 (C ₅₆ H ₃₆ N ₄ O=780.93) P-111 m/z=783.27 (C ₅₆ H ₃₇ N ₃ S=783.99) P-112 m/z=527.20 (C ₃₇ H ₂₅ N ₃ O=527.63) P-113 m/z=765.23 (C ₅₂ H ₃₅ N ₃ S ₂ =765.99) P-114 m/z=723.20 (C ₄₉ H ₂₉ N ₃ O ₂ S=723.85) P-115 m/z=569.17 (C ₃₈ H ₂₃ N ₃ O ₃ =569.62) P-116 m/z=716.14 (C ₄₇ H ₂₈ N ₂ S ₃ =716.94) P-117 m/z=692.22 (C ₄₈ H ₂₈ N ₄ O ₂ =692.78) P-118 m/z=726.18 (C ₄₉ H ₃₀ N ₂ OS ₂ =726.91) P-119 m/z=760.22 (C ₅₃ H ₃₂ N ₂ O ₂ S=760.91) P-120 m/z=516.13 (C ₃₅ H ₂₀ N ₂ OS=516.62) P-121 m/z=644.19 (C ₄₅ H ₂₈ N ₂ OS=644.79) P-122 m/z=832.25 (C ₆₀ H ₃₆ N ₂ OS=833.02) P-123 m/z=608.16 (C ₄₁ H ₂₄ N ₂ O ₂ S=608.72) P-124 m/z=694.26 (C ₅₀ H ₃₄ N ₂ O ₂ =694.83) P-125 m/z=710.33 (C ₅₂ H ₄₂ N ₂ O=710.92) P-126 m/z=686.28 (C ₄₉ H ₃₈ N ₂ S=686.92) P-127 m/z=694.24 (C ₅₀ H ₃₄ N ₂ S=694.90) P-128 m/z=766.30 (C ₅₇ H ₃₈ N ₂ O=766.94) P-129 m/z=808.25 (C ₅₈ H ₃₆ N ₂ OS=809.00) P-130 m/z=916.35 (C ₆₉ H ₄₄ N ₂ O=917.12) P-131 m/z=680.19 (C ₄₈ H ₂₈ N ₂ OS=680.83) P-132 m/z=906.31 (C ₆₇ H ₄₂ N ₂ S=907.15) P-133 m/z=726.27 (C ₅₄ H ₃₄ N ₂ O=726.88) P-134 m/z=740.28 (C ₅₅ H ₃₆ N ₂ O=740.91) P-135 m/z=784.25 (C ₅₆ H ₃₆ N ₂ OS=784.98) P-136 m/z=608.23 (C ₄₃ H ₂₉ FN ₂ O=608.72) P-137 m/z=717.91 (C ₄₇ H ₃₁ N ₃ OS ₂ =717.91) P-138 m/z=769.27 (C ₅₅ H ₃₅ N ₃ O ₂ =769.90) P-139 m/z=685.16 (C ₄₆ H ₂₇ N ₃ S ₂ =685.86) P-140 m/z=658.17 (C ₄₅ H ₂₆ N ₂ O ₂ S=658.78) P-141 m/z=707.12 (C ₄₄ H ₂₅ N ₃ OS ₃ =707.88) P-142 m/z=735.22 (C ₅₀ H ₂₉ N ₃ O ₄ =735.80) P-143 m/z=674.15 (C ₄₅ H ₂₆ N ₂ OS ₂ =674.84) P-144 m/z=690.13 (C ₄₅ H ₂₆ N ₂ S ₃ =690.90) P-145 m/z=658.17 (C ₄₅ H ₂₆ N ₂ O ₂ S=658.78) P-146 m/z=563.08 (C ₃₆ H ₂₁ NS ₃ =563.75) P-147 m/z=583.14 (C ₄₀ H ₂₅ NS ₂ =583.77) P-148 m/z=663.11 (C ₄₄ H ₂₅ NS ₃ =663.87) P-149 m/z=597.12 (C ₄₀ H ₂₃ NOS ₂ =597.75) P-150 m/z=689.13 (C ₄₆ H ₂₇ NS ₃ =689.91) P-151 m/z=574.12 (C ₃₇ H ₂₂ N ₂ OS ₂ =574.72) P-152 m/z=700.16 (C ₄₇ H ₂₈ N ₂ OS ₂ =700.87) P-153 m/z=635.17 (C ₄₂ H ₂₅ N ₃ O ₂ S=635.74) P-154 m/z=741.19 (C ₄₉ H ₃₁ N ₃ OS ₂ =741.93) P-155 m/z=752.22 (C ₅₀ H ₃₂ N ₄ O ₂ S=752.89) P-156 m/z=722.27 (C ₅₀ H ₃₄ N ₄ O ₂ =722.85) P-157 m/z=798.30 (C ₅₆ H ₃₈ N ₄ O ₂ =798.95) P-158 m/z=752.22 (C ₅₀ H ₃₂ N ₄ O ₂ S=752.89) P-159 m/z=752.22 (C ₅₀ H ₃₂ N ₄ O ₂ S=752.89) P-160 m/z=752.22 (C ₅₀ H ₃₂ N ₄ O ₂ S=752.89) P-161 m/z=700.20 (C ₄₈ H ₃₂ N ₂ S ₂ =700.92) P-162 m/z=684.22 (C ₄₈ H ₃₂ N ₂ OS=684.86) P-163 m/z=745.27 (C ₅₃ H ₃₅ N ₃ O ₂ =745.88) P-164 m/z=841.22 (C ₅₇ H ₃₅ N ₃ OS ₂ =842.05) P-165 m/z=810.27 (C ₅₈ H ₃₈ N ₂ OS=811.02) P-166 m/z=915.18 (C ₅₇ H ₃₃ N ₅ O ₂ S ₃ =916.10) P-167 m/z=915.18 (C ₅₇ H ₃₃ N ₅ O ₂ S ₃ =916.10) P-168 m/z=859.21 (C ₅₅ H ₃₃ N ₅ O ₂ S ₂ =860.02) P-169 m/z=687.23 (C ₄₅ H ₂₉ N ₅ O ₃ =687.76) P-170 m/z=921.27 (C ₅₉ H ₃₅ N ₇ O ₅ =921.97) P-171 m/z=589.10 (C ₃₈ H ₂₃ NS ₃ =589.79) P-172 m/z=676.16 (C ₄₅ H ₂₈ N ₂ OS ₂ =676.85) P-173 m/z=655.13 (C ₄₄ H ₂₇ NS ₃ =665.89) P-174 m/z=624.13 (C ₄₁ H ₂₄ N ₂ OS ₂ =624.78) P-175 m/z=617.14 (C ₃₈ H ₂₃ N ₃ O ₄ S=617.68)

[measurement test example ]

For the compound of the present invention, all thin films are deposited on an si wafer to a thickness of 1000 Å and manufactured, then n (refractive index) and k (absorption coefficient, absorption) using JA Woollam's Focused Beam Spectroscopic Ellipsometer　RC2 XF instrument. coefficient) was measured. After measurement, the final result was analyzed using the Tauc-Lorentz model and the Gaussian model.

division compound n (450 nm) k (450 nm) tanδ Comparative Example 1 SiO ₂ 1.47 0.0023 0.0031293 Comparative Example 2 Comparative compound A 2.413915 0.053885 0.0446676 Test Example 1 P-92 2.234374 0.000261 0.0002336 Test Example 2 P-95 2.302051 0.000118 0.0001025 Test Example 3 P-120 2.005773 0.000075 0.0000748 Test Example 4 P-151 2.153759 0.000005 0.0000046 Test Example 5 P-153 2.324989 0.00008 0.0000688 Test Example 6 P-154 2.119847 0.000053 0.0000500 Test Example 7 P-158 2.285066 0.000802 0.0007019 Test Example 8 P-159 2.166349 0.000033 0.0000305 Test Example 9 P-160 2.040186 0.000044 0.0000431

[Comparative compound A]

[device Example ]

comparative example One) blue Fabrication and testing of organic light emitting devices

N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate After vacuum deposition of a -diamine (hereinafter abbreviated as '2-TNATA') film to form a hole injection layer with a thickness of 60 nm, N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as 'NPB') film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Thereafter, 9,10-di(naphthalen-2-yl)anthracene as a host and BD-052X (Idemitsu kosan) as a dopant were used on the hole transport layer, but the dopant was doped so that the weight ratio was 93:7, and the thickness was 30 nm. of the light emitting layer was formed. Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as 'BAlq') was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as 'Alq3') was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and on the electron injection layer, a 9:1 ratio Mg:Ag was deposited to a thickness of 150 nm to form a cathode, SiO ₂ was formed into a film to a thickness of 60 nm to form a cap pip layer.

[ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compound A was used instead _{of SiO 2} as a material for the cappip layer.

[ comparative example 3 to comparative example 11]

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound of the present invention described in Table 5 was used instead _{of SiO 2} as the cappip layer material.

[ Example 1 to Example 9]

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound of the present invention described in Table 5 was used instead _{of SiO 2} as the capping layer material, and the Mg:Ag ratio was changed to 2:8. .

[ Example 10 to Example 18]

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound of the present invention described in Table 5 was used instead _{of SiO 2} as the capping layer material, and the Mg:Ag ratio was changed to 1:9. .

[ Example 19 to Example 27]

Ytterbium (Yb) is used instead of LiF for the electron injection layer, the compound of the present invention described in Table 5 is used instead _{of SiO 2 as the capping layer material, and the Mg:Ag ratio is 1:9, except that} An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1.

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 27 and Comparative Examples 1 to 11 of the present invention and PR-650 from Photoresearch was measured, and the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at ^{500 cd/m 2 standard luminance, and the measurement results are shown in Table 5 below.}

compound Voltage
(V) Current
Density
(mA/cm ² ) Brightness
(cd/m ² ) Efficiency
(cd/A) Lifetime
T(95) CIE x y Comparative Example (1) SiO ₂ 6.7 25.0 500.0 2.0 55.4 0.16 0.15 Comparative Example (2) Comparative compound A 6.6 11.6 500.0 4.3 56.8 0.15 0.08 Comparative Example (3) P-92 6.5 8.7 500.0 5.8 59.8 0.15 0.07 Comparative Example (4) P-95 6.5 8.6 500.0 5.8 57.1 0.15 0.07 Comparative Example (5) P-120 6.5 9.3 500.0 5.3 59.7 0.15 0.07 Comparative Example (6) P-151 6.6 9.3 500.0 5.4 57.7 0.15 0.07 Comparative Example (7) P-153 6.6 8.6 500.0 5.8 59.1 0.15 0.07 Comparative Example (8) P-154 6.6 9.4 500.0 5.3 59.2 0.15 0.07 Comparative Example (9) P-158 6.5 9.7 500.0 5.2 56.1 0.15 0.07 Comparative Example (10) P-159 6.6 9.9 500.0 5.0 59.5 0.15 0.07 Comparative Example (11) P-160 6.5 9.2 500.0 5.4 59.4 0.15 0.07 Example (1) P-92 6.8 7.4 500.0 6.8 60.1 0.15 0.07 Example (2) P-95 6.7 7.4 500.0 6.7 62.7 0.15 0.07 Example (3) P-120 6.8 7.3 500.0 6.9 62.3 0.15 0.07 Example (4) P-151 6.8 7.4 500.0 6.8 61.2 0.15 0.07 Example (5) P-153 6.7 7.3 500.0 6.8 62.9 0.15 0.07 Example (6) P-154 6.7 7.2 500.0 6.9 60.4 0.15 0.07 Example (7) P-158 6.8 7.2 500.0 7.0 62.7 0.15 0.07 Example (8) P-159 6.8 7.5 500.0 6.7 61.3 0.15 0.07 Example (9) P-160 6.7 7.3 500.0 6.9 61.2 0.15 0.07 Example (10) P-92 6.8 7.1 500.0 7.1 62.6 0.15 0.07 Example (11) P-95 6.9 7.0 500.0 7.1 61.9 0.15 0.07 Example (12) P-120 6.9 7.0 500.0 7.2 60.8 0.15 0.07 Example (13) P-151 6.9 7.1 500.0 7.0 60.6 0.15 0.07 Example (14) P-153 6.8 7.1 500.0 7.1 61.6 0.15 0.07 Example (15) P-154 6.9 7.1 500.0 7.0 62.1 0.15 0.07 Example (16) P-158 6.8 7.0 500.0 7.2 62.7 0.15 0.07 Example (17) P-159 6.9 7.1 500.0 7.0 61.4 0.15 0.07 Example (18) P-160 6.9 7.1 500.0 7.0 62.0 0.15 0.07 Example (19) P-92 6.1 6.4 500.0 7.8 67.0 0.15 0.07 Example (20) P-95 6.2 6.3 500.0 8.0 69.0 0.15 0.07 Example (21) P-120 6.2 6.3 500.0 7.9 67.1 0.15 0.07 Example (22) P-151 6.1 6.5 500.0 7.7 65.7 0.15 0.07 Example (23) P-153 6.2 6.3 500.0 7.9 65.6 0.15 0.07 Example (24) P-154 6.3 6.6 500.0 7.5 69.1 0.15 0.07 Example (25) P-158 6.2 6.3 500.0 7.9 66.7 0.15 0.07 Example (26) P-159 6.0 6.6 500.0 7.6 66.2 0.15 0.07 Example (27) P-160 6.1 6.4 500.0 7.9 66.2 0.15 0.07

As can be seen from the results of Table 5, it can be confirmed that the organic electric device using the compound of the present invention exhibits superior properties than the comparative example device that does not.

Looking in detail, it can be seen that the device using the compound of the present invention that satisfies Formula 1 compared to Comparative Example 1 and Comparative Example 2 using a compound that does not satisfy Formula 1 has slightly improved driving and lifespan, but it is significantly superior in terms of efficiency ( Comparative Examples 3 to 11). This suggests that when a compound satisfying the value of Equation 1 representing the dielectric loss characteristic is used as the capping layer, the properties of the entire device can be improved.

In addition, it can be seen that the device in which the Ag ratio is changed to 80% exhibits significantly superior efficiency than the comparative example device that does not (Examples 1 to 9), and furthermore, the width of the efficiency improvement of the device in which the Ag ratio is 90% It was confirmed that this was much larger (Examples 10 to 18). As described in the detailed description of the invention, when the Ag content is 80% or more, the reflectance is similar to that when the Ag content is less than 20%, but the absorbance is lowered and the transmittance is increased, so that the efficiency is maximized by reducing the loss of light by the cathode. is judged to be

Among them, it was confirmed that the results (Examples 19 to 27) of the device in which the electron injection layer was changed to Yb showed the most excellent device characteristics in terms of driving, efficiency, and lifespan among Examples, which may have increased Ag content. This is because the disadvantage that the driving voltage may be slightly pushed due to the low electron injection characteristics at the time of use was overcome by using Yb with good conductivity.

The above description is merely illustrative of the present invention, and various modifications will be possible without departing from the essential characteristics of the present invention by those skilled in the art to which the present invention pertains. Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: capping layer (light efficiency improvement layer) 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (20)

anode; cathode; an organic material layer formed between the anode and the cathode; In the organic electric device comprising a; and a capping layer,
The organic material layer includes a hole transport region, a light emitting layer and an electron transport region,
The electron transport region includes an electron transport layer and an electron injection layer,
The negative electrode is a mixture of magnesium (Mg) and silver (Ag), wherein the ratio of the silver (Ag) is 80% or more,
The capping layer is an organic electric device comprising a compound satisfying the following formula 1 at a wavelength of 450 nm
[Equation 1]
tanδ (Loss tangent) ≤ 0.001
{In the above formula 1,
1) tanδ is ε ² /ε ¹ ,
2) ε ² is the imaginary part of the complex permittivity of the dielectric material representing the dielectric loss, expressed as 2nk,
3) ε ¹ is the real part of the complex permittivity representing the permittivity, denoted by n ² -k ² ,
4) n is the refractive index, and k is the absorption coefficient.}
The organic electric device according to claim 1, wherein the electron transport region necessarily includes Ytterbium (Yb), which is a lanthanide group.
The organic electric device according to claim 1, wherein the capping layer compound has a refractive index of 2.1 or more at a wavelength of 450 nm, a refractive index of 1.95 or more at a wavelength of 530 nm, and a refractive index of 1.85 or more at a wavelength of 620 nm.
The organic electric device according to claim 1, wherein the capping layer compound has a refractive index difference of 0.08 or more at wavelengths of 430 nm and 460 nm.
The organic electric device according to claim 1, wherein the absorption coefficient of the capping layer compound is 0.3 or more at a wavelength of 410 nm.
The organic electric device according to claim 1, wherein the capping layer compound has an absorption coefficient of 0.1 or more at a wavelength of 410 nm to 430 nm.
The organic electric device according to claim 1, wherein the capping layer compound has an absorbance of 0.2 or more at a wavelength of 400 nm to 410 nm in an absorption spectrum at a ^{concentration of 10 - 5 mol/L.}
The compound for a capping layer of an organic electric device according to claim 1, characterized in that it is represented by the following formula (1) while satisfying the following formula (1)
[Equation 1]
tanδ (Loss tangent) ≤ 0.001
{In the above formula 1,
1) tanδ is ε ² /ε ¹ ,
2) ε ² is the imaginary part of the complex permittivity of the dielectric material representing the dielectric loss, expressed as 2nk,
3) ε ¹ is the real part of the complex permittivity representing the permittivity, denoted by n ² -k ² ,
4) n is the refractive index, and k is the absorption coefficient.}
[Formula 1]

{In Formula 1,
1) Ar ¹ , Ar ^{2 ,} and Ar ³ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); selected from the group consisting of
2) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And selected from the group consisting of combinations thereof,
3) wherein R _a is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and -L ⁴ Ar ⁵ ; selected from the group consisting of;
4) wherein R _b is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and -L ⁵ Ar ⁶ ; selected from the group consisting of;
5) Ar ⁵ and Ar ⁶ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ An aryloxy group; is selected from the group consisting of,
6) L ¹ , L ² , L ³ , L ⁴ and L ⁵ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₂ ~ C ₆₀ A heterocyclic group is selected from the group consisting of;
Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ An alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ ~ C ₂₀ Aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; and -L'-N(R _a )(R _b ); 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, where 'ring' means C ₃ ~ C ₆₀ aliphatic ring or C ₆ ~ C ₆₀ aromatic ring or C ₂ ~ C ₆₀ refers to a fused ring consisting of a heterocyclic ring or a combination thereof, including a saturated or unsaturated ring.}
The compound according to claim 8, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1.
[Formula 1-1]

{In Formula 1-1,
1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) X is O or S;
3) Z is N or CR ^e ,
4) R ¹ and R ^e are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); selected from the group consisting of, R ¹ are the same as or different from each other,
5) L', R _a and R _b are the same as defined in claim 8,
6) a is i) ^{an integer of 0 to 4 when L 1} is bonded to *, and ii) an integer of 0 to 3 when ^{L 1 is not bonded to *.}}
The compound according to claim 8, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-2 or Chemical Formula 1-3.
[Formula 1-2] [Formula 1-3]

{In Formula 1-2 or Formula 1-3,
1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) X, R ¹ and a are the same as defined in claim 9 above.}
The compound according to claim 8, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-4.
[Formula 1-4]

{In Formula 1-4,
1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) Y is NR, CR'R", O or S;
3) The R, R' and R" are each independently a C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; and O, N, S, Si and P at least one hetero _{A C 2} ~ C ₆₀ heterocyclic group containing an atom; or selected from the group consisting of, or R' and R" are bonded to each other to C ₆ ~ C ₆₀ Aromatic hydrocarbon; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; or C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring to form;
4) R ¹ ' and R ² ' are the ^{same as the definition of R 1} in claim 9, and are the same or different from each other,
5) a' is an integer from 0 to 4, and b' is an integer from 0 to 3.}
The compound according to claim 8, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-5.
[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Formula 2-4] [Formula 2-5]

{In Formulas 2-1 to 2-5,
1) Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) X, Z, R ¹ and a are the same as defined in claim 9,
3) X ¹ and X ² are the same as the definition of X in claim 9,
4) Y ¹ and Y ² are the same as the definition of Y in claim 11,
5) Z ¹ and Z ² are the same as the definition of Z in claim 9,
6) R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are the same as defined ^{for R 1 in claim 9,}
7) b is i) an integer of 0 to 4 when ^{L 2} is bonded to *, ii) an integer of 0 to 3 when ^{L 2 is not bonded to *,}
8) c is i) an integer of 0 to 4 when ^{L 3} is bonded to *, ii) an integer of 0 to 3 when ^{L 3 is not bonded to *,}
9) d and f are independently integers from 0 to 3, and e and g are independently integers from 0 to 4.}
The compound according to claim 8, wherein Chemical Formula 1 is represented by the following Chemical Formula 2-6 or Chemical Formula 2-7
[Formula 2-6] [Formula 2-7]

{In Formulas 2-6 to 2-7,
1) Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) Y, R ¹ ', R ² ', a' and b' are the same as defined in claim 11 above,
3) Y ¹ and Y ² are the same as the definition of Y in claim 11,
4) R ⁴ , R ⁵ , R ⁶ and R ⁷ are the same as defined ^{for R 1 in claim 9,}
5) d and f are each independently an integer from 0 to 3, and e and g are each independently an integer from 0 to 4.}
The compound according to claim 8, wherein Chemical Formula 1 is represented by the following Chemical Formula 3
[Formula 3]

{In Formula 3,
1) Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined in claim 8,
2) L ⁴ and L ⁵ are the same as the definition ^{of L 1 in claim 8,}
3) Ar ⁵ and Ar ⁶ are the same as defined ^{for Ar 1 in claim 8.}}
The compound according to claim 8, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 3-1 to 3-4 below.
[Formula 3-1] [Formula 3-2]

[Formula 3-3] [Formula 3-4]

{In Formulas 3-1 to 3-4,
1) Ar ² , Ar ³ , L′, L ¹ , L ² and L ³ are the same as defined in claim 8,
2) L ⁴ and L ⁵ are the same as the definition ^{of L 1 in claim 8,}
3) Ar ⁵ and Ar ⁶ are the same as defined ^{for Ar 1 in claim 8,}
4) X, Z and R ¹ are the same as defined in claim 9 above,
5) Y, R ¹ ', R ² ', a' and b' are the same as defined in claim 11 above,
6) X ^a is the same as the definition of X in claim 9,
7) Y ^a is the same as the definition of Y in claim 11,
8) Z ^a is the same as the definition of Z in claim 9,
9) R ¹ ", R ² " and R ³ " are the same as the definition ^{of R 1 in claim 9,}
10) a is i) an integer of 0 to 4 when ^{L 2} is bonded to *, ii) an integer of 0 to 3 when ^{L 2 is not bonded to *,}
11) a", b" and c" are each independently an integer from 0 to 3.}
The compound according to claim 8, wherein the compound represented by Formula 1 is represented by any one of the following compounds P-1 to P-175.

The organic electric device according to claim 1, wherein the organic material layer includes at least two stacks including a hole transport region, a light emitting layer, and an electron transport region sequentially formed on the anode.
The organic electric device according to claim 1, wherein the organic material layer further comprises a charge generating layer formed between the two or more stacks.
A display device comprising the organic electric device of claim 1; and a control unit configured to drive the display device.
The electronic device according to claim 19, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.

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