KR20220089970A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric device including an anode, a cathode, and an organic material layer between the anode and the cathode, and an electronic device including the organic electric element, wherein the organic material layer is represented by Chemical Formulas (1) and (2) of the present invention By including each of the displayed compounds, it is possible to lower the driving voltage of the organic electric device and improve luminous efficiency and lifespan.

Description

An organic electric device comprising a compound for an organic electric device, and an electronic device thereof

The present invention relates to an organic electric device using a compound for an organic electric device and an electronic device thereof.

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 material 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.

Lifespan and efficiency are the most problematic for organic light emitting diodes, and as displays become larger, these problems of efficiency and lifespan must be resolved. 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. This is because, 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, a long lifespan and high efficiency can be achieved at the same time.

In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer. It is time for layer development.

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, most materials used for the hole transport layer have a low T1 value because they have to have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. This results in light emission at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it is urgently required to develop a light emitting auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.

On the other hand, while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of the organic electric device, stable characteristics against Joule heating generated during device driving, that is, high glass transition There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a characteristic of lowering the uniformity of the thin film surface when driving the device, which is reported to have a significant effect on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance.

That is, 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, a light emitting auxiliary layer material, etc. is stable and efficient. Supported by materials should be preceded, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently developed. Accordingly, the development of new materials continues to be demanded.

An object of the present invention is to provide an organic electric device including a compound capable of lowering the driving voltage of the device and improving the luminous efficiency, color purity, stability and lifespan of the device, and an electronic device thereof.

In one aspect, the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer and the light emitting layer is phosphorescent An organic electric device comprising a compound represented by the following Chemical Formulas (1) and (2) as a light emitting layer is provided.

Formula (1) Formula (2)

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 Alkoxyl group, C ₁ ~ C 20 Alkylamine group, C ₁ ~ C ₂₀ Alkylthiophene group, C ₆ ~ C _{20 Arylthiophene} group, C ₂ ~ C ₂₀ Alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkenyl group, silane group, boron 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 manner 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, wherein 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, the 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 when the light efficiency improving layer 180 is formed Light efficiency of the organic electric device may be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the light efficiency improving layer 180 is formed by forming the second electrode 170 . ) can reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.

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 .

Referring to FIG. 2 , the organic electric device 200 according to another embodiment of the present invention includes 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 light efficiency improving layer 180 is formed on the second electrode. can be

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, in the organic electric device according to an embodiment of the present invention, a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode 170 and the light efficiency improving 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 light emitting layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second light emitting layer 440 , and a second electron transport layer 450 . . As described above, the first stack and the second stack may be organic material layers having the same stacked structure or may be 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 generation layer (CGL) is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the current efficiency generated in each light emitting layer, and 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 compounds represented by Chemical Formulas (1) and (2) of the present invention are the hole injection layers 120, 320, 420, the hole transport layers 130, 330, 430, the buffer layer 210, and the light emission auxiliary layer 220. , the electron transport layer (150, 350, 450), the electron injection layer 160, the light emitting layer (140, 340, 440) or can be used as a material of the light efficiency improvement layer 180, preferably, the formula (1) of the present invention And the compound represented by Formula (2) may be used as a host of the light emitting layer (140, 340, 440).

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 is an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer and the light emitting layer includes a compound represented by the following Chemical Formulas (1) and (2) as a phosphorescent light emitting layer.

Formula (1) Formula (2)

In the above formulas (1) and (2), each symbol may be defined as follows.

1) X is O or S;

2) X ¹ , X ² and X ³ are each independently C(R ₁ ) or N, provided that at least one of X ¹ , X ² and X ³ is N,

3) R ¹ , R ² , R ³ , R ⁴ and R ₁ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl 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 ); to form a ring.

When R ¹ , R ² , R ³ , R ⁴ and R ₁ are an aryl group, preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₂₅ aryl group, such as phenylene, bi phenyl, naphthalene, terphenyl, and the like.

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

When R ¹ , R ² , R ³ , R ⁴ and R ₁ are 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 It may be a fused ring group of a C ₃ ~ C ₂₄ aliphatic ring and a C ₆ ~ C ₂₄ aromatic ring.

When R ¹ , R ² , R ³ , R ⁴ and R ₁ are an alkyl group, it may be preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

When R ¹ , R ² , R ³ , R ⁴ and R ₁ are an alkoxyl group, it may be preferably a C ₁ to C ₂₄ alkoxyl group.

When R ¹ , R ² , R ³ , R ⁴ and R ₁ are an aryloxy group, it may be an aryloxy group of preferably C ₆ to C ₂₄ .

4) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; and O, N, S, Si, and P, a C ₂ ~ C ₆₀ heterocyclic group comprising at least one heteroatom; selected from the group consisting of, wherein R ^a and R ^b are each independently C ₆ ~C an aryl group of ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; is selected from the group consisting of.

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

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

When L' is 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, pyrimido Indole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine , phenothiazine, phenylphenothiazine, and the like.

When R ^a and R ^b are an aryl group, preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₂₅ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc. may be .

When R ^a and R ^b are aliphatic cyclic groups, they may be preferably C ₃ to C ₃₀ aliphatic groups, more preferably C ₃ to C ₂₄ aliphatic groups.

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, benzofu lopyrimidine, phenothiazine, phenylphenothiazine, and the like.

5) a, b, c and d are each independently an integer of 0 to 4,

6) i and j are each independently an integer of 0 to 2, with the proviso that i+j is an integer of 1 or more,

7) 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; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring 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 , phenylene, biphenyl, naphthalene, terphenyl, and the like.

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. Exemplarily pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When L ¹ , L ² , L ³ , L ⁴ and L ⁵ are 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 It may be a fused ring group of a C ₃ ~ C ₂₄ aliphatic ring and a C ₆ ~ C ₂₄ aromatic ring.

8) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ 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; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are aryl groups, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₅ aryl group , such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ It may be a heterocyclic group, illustratively pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoqui nasol, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are fused ring groups, 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 a C ₆ ~ C ₂₄ aromatic ring fused ring group.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, more preferably C ₁ to C ₂₄ . It may be an alkyl group.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are alkoxyl groups, they may be preferably C ₁ to C ₂₄ alkoxyl groups.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are aryloxy groups, they may be preferably C ₆ -C ₂₄ aryloxy groups.

9) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkoxyl group and 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 Alkoxy 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; and a C ₈ ~ C ₂₀ arylalkenyl group; 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 of an aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or a C ₂ ~ C ₆₀ heterocyclic ring or a fused ring consisting of a combination thereof, and includes a saturated or unsaturated ring.

In addition, the present invention provides an organic electric device in which the compound represented by the formula (1) is represented by any one of the following formulas (3) to (9).

Chemical formula (3) Chemical formula (4) Chemical formula (5)

Formula (6) Formula (7)

Formula (8) Formula (9)

{In the above formulas (3) to (9),

1) X, R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are defined in Formula (1) above. Same as bar,

2) a', b', c' and d' are independently integers from 0 to 3, and b" and d" are independently integers from 0 to 2.}

In addition, the present invention provides an organic electric device in which the compound represented by the formula (1) is represented by the following formula (10) or formula (11).

Formula (10) Formula (11)

{In Formulas (10) and (11), R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , i and j are the same as defined in Formula (1) above.}

In addition, the present invention provides an organic electric device in which the compound represented by the above formula (1) is represented by the following formula (12) or (13).

Formula (12) Formula (13)

{In the above formula (12) or formula (13),

1) X, R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , i and j are the formula (1) ) as defined in

2) Ring A is a C ₁₀ ~ C ₂₀ aryl group; Or C ₁₀ ~ C ₂₀ A heterocyclic group; and

3) a" and c" are each independently an integer from 0 to 10.}

In addition, the present invention provides an organic electric device wherein at least one of Ar ¹ , Ar ² , Ar ³ and Ar ⁴ is represented by the following Chemical Formula (B-1).

Formula (B-1)

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

1) Ring D and ring E are each independently a C ₆ ~ C ₂₀ aryl group; Or C ₄ ~ C ₂₀ A heterocyclic group; and

2) V ¹ and V ² are each independently a single bond, NR ^c , CR ^d R ^e , O or S,

3) R ^c , R ^d and R ^e are each independently a C ₆ ~ C ₆₀ aryl 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; and a C ₆ ~ C ₃₀ aryloxy group; selected from the group consisting of, or R ^d and R ^e may be bonded to each other to form a ring.

When R ^c , R ^d and R ^e are an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₅ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl etc.

When R ^c , R ^d and ^Re are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, illustratively pyrazine, cy Offene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine , benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R ^c , R ^d and ^Re are 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 a C ₃ ~ C ₂₄ It may be a fused ring group of an aliphatic ring and a C ₆ ~ C ₂₄ aromatic ring.

When R ^c , R ^d and ^Re are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When R ^c , R ^d and R ^e are an alkoxyl group, it may be preferably a C ₁ to C ₂₄ alkoxyl group.

When R ^c , R ^d and R ^e are an aryloxy group, it may be preferably a C ₁ to C ₂₄ aryloxy group.

은 결합되는 위치를 나타낸다.4)

indicates a binding position.

Specifically, the compound represented by Formula (1) may be any one of the following compounds.

In addition, the present invention provides an organic electric device in which at least one of Ar ⁵ , Ar ⁶ and Ar ⁷ is represented by any one of the following Chemical Formulas (2-1) to (2-6).

Formula (2-1) Formula (2-2) Formula (2-3)

Formula (2-4) Formula (2-5) Formula (2-6)

{In the above formulas (2-1) to (2-6),

1) X ¹² and X ¹³ are each independently NL ⁶ -Ar ⁸ , O, S, C(R ₂ ) or CR'R",

2) The R ₂ , R′, R″, R ⁵ and R ⁶ are the same or different, and are each independently hydrogen; deuterium; halogen; C ₁ ~ C ₂₀ Alkyl group or C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; cyano group; nitro group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₂₀ aryloxy 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; Fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ Hetero It ^may be selected from _the ^{group consisting} of a _cyclic ^group ; or R' and R" may combine with each other to form a spy ring,

3) L ⁶ is the same as the definition of L ¹ in Formula (1),

4) Ar ⁸ is the same as the definition of Ar ¹ in Formula (1),

5) e and f are each independently an integer from 0 to 4, and f' is an integer from 0 to 6.}

In addition, the present invention provides an organic electric device in which the compound represented by the formula (2) is represented by any one of the following formulas (2-7) to (2-9).

Formula (2-7) Formula (2-8)

Formula (2-9)

{In the above formulas (2-7) to (2-9),

1) X ³ , L ³ , L ⁴ , L ⁵ , Ar ⁶ and Ar ⁷ are the same as defined in Formula (2) above,

2) R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same as defined for R ⁵ in Formula (2-1),

3) e, f, g, h, k and l are each independently an integer from 0 to 4.}

In addition, the present invention provides an organic electric device in which the compound represented by the formula (2) is represented by any one of the following formulas (2-10) to (2-12).

Formula (2-10) Formula (2-11)

Formula (2-12)

{In the above formulas (2-10) to (2-12),

1) X ³ , L ³ , L ⁴ , L ⁵ , Ar ⁶ and Ar ⁷ are the same as defined in Formula (2) above,

2) X ¹² , X ¹⁴ and X ¹⁵ are the same as defined for X ¹² in Formula (2-1),

3) R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same as defined for R ⁵ in Formula (2-1),

4) e, h and k are independently integers from 0 to 4, and f", g' and l' are independently integers from 0 to 3.}

In addition, the present invention provides an organic electric device in which the L ¹ , L ² , L ³ , L ⁴ or L ⁵ is represented by any one of the following Chemical Formulas (b-1) to (b-13).

Formula (b-1) Formula (b-2) Formula (b-3) Formula (b-4) Formula (b-5)

Formula (b-6) Formula (b-7) Formula (b-8) Formula (b-9)

Formula (b-10) Formula (b-11) Formula (b-12) Formula (b-13)

In Formulas (b-1) to (b-13), each symbol may be defined as follows.

1) Z is O, S, NL ⁷ -Ar ⁹ or CR ^f R ^g ,

2) L ⁷ is the same as the definition of L ¹ in Formula (1),

3) Ar ⁹ is the same as the definition of Ar ¹ in Formula (1),

4) R ¹¹ , R ¹² and R ¹³ are the same as defined for R ¹ in Formula (1),

5) R ^f and R ^g are the same as the definition of R ^c in Formula (B-1) above,

6) m, o and p are each independently an integer from 0 to 4, n is an integer from 0 to 6, q and r are independently from each other an integer from 0 to 3, s is an integer from 0 to 2, t is 0 or 1,

7) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently of each other CR ^h or N, provided that at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,

8) wherein R ^h is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl 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; And C ₆ ~ C ₃₀ Aryloxy group; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring.

When R ^h is an aryl group, it may be preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₅ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

When R ^h is 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, pyrimido Indole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine , phenothiazine, phenylphenothiazine, and the like.

When R ^h is 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 a C ₃ ~ C ₂₄ aliphatic ring and C ₆ ~ It may be a fused ring group of an aromatic ring of C ₂₄ .

When R ^h is an alkyl group, it may be preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

When R ^h is an alkoxyl group, it may be preferably a C ₁ to C ₂₄ alkoxyl group.

When R ^h is an aryloxy group, it may be preferably a C ₆ -C ₂₄ aryloxy group.

Specifically, the compound represented by Formula (2) may be any one of the following compounds.

The present invention may further include a light efficiency improving layer formed on at least one surface opposite to the organic material layer among one surface of the first electrode and the second electrode.

In addition, the organic material layer may include two or more stacks including a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode, and the organic material layer may further include a charge generating layer formed between the two or more stacks.

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 One]

The compound (Final product 1) represented by Formula (1) according to the present invention may be prepared by reacting as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

{In Scheme 1, Hal is Cl, Br, or I, G ₁ is Ar ¹ or Ar ³ , and G ₂ is Ar ² or Ar ⁴ }

I. Sub 1 Synthesis Example

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

<Scheme 2>

{In Scheme 2, Hal is Cl, Br, or I.}

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

of Sub 1-1 Synthesis example

(1) Synthesis of Sub 1-1A

After dissolving 4-chloro-9H-xanthen-9-one (20 g, 86.71 mmol) and 2-bromo-1,1'-biphenyl (21.22 g, 91.05 mmol) in THF (600 ml), the temperature of the reactant was adjusted. The temperature was lowered to -78 °C, n-BuLi (2.5 M in hexane) (6.11 g, 95.38 mmol) was slowly added thereto, and the reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reactant was quenched by putting it in H ₂ O, then water in the reactant was removed, filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated using column chromatography to obtain 29.7 g of the product. (Yield: 89%)

(2) Synthesis of Sub 1-1

Sub 1-1A (20 g, 51.97 mmol), (HCl 4 ml), and acetic acid (208 ml) were added and stirred at 80° C. for 1 hour. When the reaction was completed, the organic solvent was concentrated after filtration under reduced pressure, and the resulting product was separated using column chromatography to obtain 17.54 g of the product. (Yield: 92%)

of Sub 1-6 Synthesis example

(1) Synthesis of Sub 1-6A

4-chloro-9H-xanthen-9-one (20 g, 101.93 mmol) and 2-bromo-1,1'-biphenyl (28.64 g, 107.03 mmol), THF (680 ml), n-BuLi (2.5 M in hexane) (7.18 g, 112.12 mmol) was used for the synthesis of Sub1-1A to obtain 33.3 g of the product. (Yield: 85%)

(2) Synthesis of Sub 1-6

Sub 1-6A (20 g, 51.97 mmol), HCl (4 ml), and acetic acid (208 ml) were obtained by using the synthesis method of Sub1-1 above to obtain 16.78 g of the product. (Yield: 88%)

of Sub 1-46 Synthesis example

(1) Synthesis of Sub 1-46A

3-chloro-9H-thioxanthen-9-one (20 g, 81.07 mmol) with 2-bromo-1,1'-biphenyl (19.84 g, 85.12 mmol), THF (600 ml), n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol) was used for the synthesis of Sub1-1A to obtain 25.7 g of the product. (Yield: 79%)

(2) Synthesis of Sub 1-46

15.47 g of Sub 1-46A (20.8 g, 51.97 mmol), HCl (4 ml), and acetic acid (200 ml) were obtained by using the synthesis method of Sub1-1 above. (Yield: 81%)

Sub 1-55's Synthesis example

(1) Synthesis of Sub 1-55A

2-chloro-9H-thioxanthen-9-one (20 g, 81.07 mmol) with 4-bromo-2-iodo-1,1'-biphenyl (30.56 g, 85.12 mmol), THF (600 ml), n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol) was obtained by using the synthesis method of Sub1-1A above to obtain 33.06 g of the product. (Yield: 85%)

(2) Synthesis of Sub 1-55

Sub 1-55A (20 g, 41.68 mmol), HCl (3.5 ml), and acetic acid (167 ml) were obtained by using the synthesis method of Sub1-1 above to obtain 16.75 g of the product. (Yield: 87%)

Meanwhile, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.

Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to the Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-2 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-3 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-4 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-5 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-6 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-7 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-8 m/z=366.08 (C ₂₅ H ₁₅ ClO=366.84) Sub 1-9 m/z=384.07 (C ₂₅ H ₁₄ ClFO=384.83) Sub 1-10 m/z=391.08 (C ₂₆ H ₁₄ ClNO=391.85) Sub 1-11 m/z=406.11 (C ₂₈ H ₁₉ ClO=406.91) Sub 1-12 m/z=396.09 (C ₂₆ H ₁₇ ClO ₂ =396.87) Sub 1-13 m/z=370.11 (C ₂₅ H ₁₁ D ₄ ClO=370.87) Sub 1-14 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-15 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-16 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-17 m/z=443.11 (C ₃₀ H ₁₈ ClNO=443.93) Sub 1-18 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-19 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-20 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-21 m/z=492.13 (C ₃₅ H ₂₁ ClO=493) Sub 1-22 m/z=548.1 (C ₃₇ H ₂₁ ClOS=549.08) Sub 1-23 m/z=532.12 (C ₃₇ H ₂₁ ClO ₂ =533.02) Sub 1-24 m/z=498.18 (C ₃₅ H ₂₇ ClO=499.05) Sub 1-25 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-26 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-27 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-28 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-29 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-30 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-31 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-32 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-33 m/z=443.99 (C ₂₅ H ₁₄ BrClO=445.74) Sub 1-34 m/z=520.02 (C ₃₁ H ₁₈ BrClO=521.84) Sub 1-35 m/z=570.04 (C ₃₅ H ₂₀ BrClO=571.9) Sub 1-36 m/z=570.04 (C ₃₅ H ₂₀ BrClO=571.9) Sub 1-37 m/z=416.1 (C ₂₉ H ₁₇ ClO=416.9) Sub 1-38 m/z=416.1 (C ₂₉ H ₁₇ ClO=416.9) Sub 1-39 m/z=510.06 (C ₃₃ H ₁₉ BrO=511.42) Sub 1-40 m/z=510.06 (C ₃₃ H ₁₉ BrO=511.42) Sub 1-41 m/z=472.07 (C ₃₁ H ₁₇ ClOS=472.99) Sub 1-42 m/z=575.09 (C ₃₇ H ₂₂ BrNO=576.49) Sub 1-43 m/z=531.14 (C ₃₇ H ₂₂ ClNO=532.04) Sub 1-44 m/z=500.04 (C ₃₁ H ₁₇ BrO ₂ =501.38) Sub 1-45 m/z=382.06 (C ₂₅ H ₁₅ ClS=382.91) Sub 1-46 m/z=382.06 (C ₂₅ H ₁₅ ClS=382.91) Sub 1-47 m/z=382.06 (C ₂₅ H ₁₅ ClS=382.91) Sub 1-48 m/z=382.06 (C ₂₅ H ₁₅ ClS=382.91) Sub 1-49 m/z=426.01 (C ₂₅ H ₁₅ BrS=427.36) Sub 1-50 m/z=426.01 (C ₂₅ H ₁₅ BrS=427.36) Sub 1-51 m/z=426.01 (C ₂₅ H ₁₅ BrS=427.36) Sub 1-52 m/z=426.01 (C ₂₅ H ₁₅ BrS=427.36) Sub 1-53 m/z=444 (C ₂₅ H ₁₄ BrFS=445.35) Sub 1-54 m/z=459.97 (C ₂₅ H ₁₄ BrClS=461.8) Sub 1-55 m/z=459.97 (C ₂₅ H ₁₄ BrClS=461.8) Sub 1-56 m/z=459.97 (C ₂₅ H ₁₄ BrClS=461.8) Sub 1-57 m/z=534.12 (C ₃₇ H ₂₃ ClS=535.1) Sub 1-58 m/z=508.11 (C ₃₅ H ₂₁ ClS=509.06) Sub 1-59 m/z=552.05 (C ₃₅ H ₂₁ BrS=553.52) Sub 1-60 m/z=536 (C ₃₁ H ₁₈ BrClS=537.9) Sub 1-61 m/z=536 (C ₃₁ H ₁₈ BrClS=537.9) Sub 1-62 m/z=432.07 (C ₂₉ H ₁₇ ClS=432.97) Sub 1-63 m/z=476.02 (C ₂₉ H ₁₇ BrS=477.42) Sub 1-64 m/z=432.07 (C ₂₉ H ₁₇ ClS=432.97) Sub 1-65 m/z=591.07 (C ₃₇ H ₂₂ BrNS=592.55) Sub 1-66 m/z=472.07 (C ₃₁ H ₁₇ ClOS=472.99)

II. Sub 2 Synthesis Example

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.

<Scheme 3>

{In Scheme 3, G ₁ is Ar ¹ or Ar ³ , and G ₂ is Ar ² or Ar ⁴ }

of Sub 2-1 Synthesis example

Put bromobenzene (37.1 g, 236.2 mmol) in a round-bottom flask and dissolve it with toluene (2200 mL), then aniline (20 g, 214.8 mmol), Pd ₂ (dba) ₃ (9.83 g, 10.7 mmol), P( t -Bu ) ₃ (4.34 g, 21.5 mmol), NaO t -Bu (62 g, 644.3 mmol) were added sequentially and stirred at 100°C. After the reaction was completed, the organic layer was extracted with ether and water, dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized using silicagel column to obtain 28 g of Sub 2-1 (yield: 77%).

Synthesis example of Sub 2-37

3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1550 mL), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), Pd ₂ (dba) ₃ ( 6.76 g, 7.4 mmol), P( t -Bu) ₃ (3 g, 14.8 mmol), and NaO t -Bu (42.6 g, 443.2 mmol) were prepared using the above Sub 2-1 synthesis method for Sub 2-37 37.9 g ( Yield: 73%) was obtained.

The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto.

Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub 2 above.

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=194.08 (C ₁₃ H ₁₀ N ₂ =194.24) Sub 2-3 m/z=174.12 (C ₁₂ H ₆ D ₅ N=174.26) Sub 2-4 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-5 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-6 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-7 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-8 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-9 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-10 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub 2-11 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub 2-12 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-13 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 2-14 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 2-15 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-16 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-17 m/z=319.14 (C ₂₄ H ₁₇ N=319.41) Sub 2-18 m/z=167.07 (C ₁₂ H ₉ N=167.21) Sub 2-19 m/z=170.08 (C ₁₁ H ₁₀ N ₂ =170.22) Sub 2-20 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 2-21 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 2-22 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 2-23 m/z=361.18 (C ₂₇ H ₂₃ N=361.49) Sub 2-24 m/z=409.18 (C ₃₁ H ₂₃ N=409.53) Sub 2-25 m/z=409.18 (C ₃₁ H ₂₃ N=409.53) Sub 2-26 m/z=347.17 (C ₂₆ H ₂₁ N=347.46) Sub 2-27 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 2-28 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 2-29 m/z=335.17 (C ₂₅ H ₂₁ N=335.45) Sub 2-30 m/z=397.18 (C ₃₀ H ₂₃ N=397.52) Sub 2-31 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub 2-32 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub 2-33 m/z=410.18 (C ₃₀ H ₂₂ N ₂ =410.52) Sub 2-34 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-35 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-36 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-37 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 2-38 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub 2-39 m/z=381.06 (C ₂₄ H ₁₅ NS ₂ =381.51) Sub 2-40 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-41 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-42 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-43 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-44 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-45 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-46 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-47 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-48 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-49 m/z=349.11 (C ₂₄ H ₁₅ NO ₂ =349.39) Sub 2-50 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-51 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-52 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-53 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-54 m/z=375.16 (C ₂₇ H ₂₁ NO=375.47) Sub 2-55 m/z=307.05 (C ₁₈ H ₁₃ NS ₂ =307.43) Sub 2-56 m/z=307.05 (C ₁₈ H ₁₃ NS ₂ =307.43) Sub 2-57 m/z=275.09 (C ₁₈ H ₁₃ NO ₂ =275.31) Sub 2-58 m/z=325.11 (C ₂₂ H ₁₅ NO ₂ =325.37) Sub 2-59 m/z=341.09 (C ₂₂ H ₁₅ NOS=341.43) Sub 2-60 m/z=350.14 (C ₂₄ H ₁₈ N ₂ O=350.42) Sub 2-61 m/z=367.14 (C ₂₅ H ₂₁ NS=367.51) Sub 2-62 m/z=301.15 (C ₂₁ H ₁₉ NO=301.39) Sub 2-63 m/z=301.15 (C ₂₁ H ₁₉ NO=301.39) Sub 2-64 m/z=376.19 (C ₂₇ H ₂₄ N ₂ =376.5) Sub 2-65 m/z=426.21 (C ₃₁ H ₂₆ N ₂ =426.56) Sub 2-66 m/z=441.16 (C ₃₁ H ₂₃ NS=441.59) Sub 2-67 m/z=425.18 (C ₃₁ H ₂₃ NO=425.53) Sub 2-68 m/z=500.23 (C ₃₇ H ₂₈ N ₂ =500.65) Sub 2-69 m/z=423.16 (C ₃₁ H ₂₁ NO=423.52) Sub 2-70 m/z=423.16 (C ₃₁ H ₂₁ NO=423.52) Sub 2-71 m/z=515.17 (C ₃₇ H ₂₅ NS=515.67) Sub 2-72 m/z=299.09 (C ₂₀ H ₁₃ NO ₂ =299.33) Sub 2-73 m/z=341.12 (C ₂₃ H ₁₉ NS=341.47) Sub 2-74 m/z=315.07 (C ₂₀ H ₁₃ NOS=315.39) Sub 2-75 m/z=315.07 (C ₂₀ H ₁₃ NOS=315.39) Sub 2-76 m/z=374.14 (C ₂₆ H ₁₈ N ₂ O=374.44)

III. Final product 1 synthesis example

1-1 of Synthesis example

Sub 1-1 (10 g, 27.26 mmol) was placed in a round-bottom flask and dissolved with Toluene (300 mL), Sub 2-1 (5.07 g, 29.99 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36) mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), and NaO t -Bu (7.86 g, 81.78 mmol) were added and stirred at 100°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 11.7 g (yield: 86%) of the product.

1-15 of Synthesis example

Sub 1-3 (10 g, 27.26 mmol), Toluene (500 mL), Sub 2-27 (12.22 g, 29.99 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), NaO t -Bu (7.86 g, 81.78 mmol) was obtained by using the above 1-1 synthesis method to obtain 15.89 g (yield: 79%) of the product.

1-27 of Synthesis example

Sub 1-3 (10 g, 27.26 mmol), Toluene (500 mL), Sub 2-56 (9.22 g, 29.99 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), NaO t -Bu (7.86 g, 81.78 mmol) was obtained by using the above 1-1 synthesis method to obtain 14.6 g (yield: 84%) of the product.

1-42's Synthesis example

Sub 1-50 (10 g, 23.40 mmol), Toluene (500 mL), Sub 2-14 (5.64 g, 25.74 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), NaO t -Bu (7.86 g, 81.78 mmol) was obtained by using the above 1-1 synthesis method to obtain 10.85 g (yield: 82%) of the product.

1-74 of Synthesis example

Sub 1-59 (10 g, 18.07 mmol), Toluene (500 mL), Sub 2-1 (3.36 g, 19.87 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), NaO t -Bu (7.86 g, 81.78 mmol) was obtained by using the above 1-1 synthesis method to obtain 9.9 g (yield: 85%) of the product.

1-103's Synthesis example

Sub 1-56 (10 g, 21.65 mmol), Toluene (500 mL), Sub 2-1 (4.03 g, 23.82 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), P( t -Bu) ₃ (0.55 g, 2.73 mmol), NaO t -Bu (7.86 g, 81.78 mmol) was obtained by using the above 1-1 synthesis method to obtain 12.63 g (yield: 90%) of the product.

compound FD-MS compound FD-MS 1-1 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) 1-2 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) 1-3 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) 1-4 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) 1-5 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-6 m/z=589.2 (C ₄₃ H ₂₇ NO ₂ =589.69) 1-7 m/z=549.21 (C ₄₁ H ₂₇ NO=549.67) 1-8 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) 1-9 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-10 m/z=605.18 (C ₄₃ H ₂₇ NOS=605.76) 1-11 m/z=615.26 (C ₄₆ H ₃₃ NO=615.78) 1-12 m/z=565.19 (C ₄₁ H ₂₇ NS=565.73) 1-13 m/z=695.19 (C ₄₉ H ₂₉ NO ₂ S=695.84) 1-14 m/z=755.26 (C ₅₆ H ₃₇ NS=755.98) 1-15 m/z=737.27 (C ₅₆ H ₃₅ NO=737.9) 1-16 m/z=671.17 (C ₄₇ H ₂₉ NS ₂ =671.88) 1-17 m/z=639.22 (C ₄₇ H ₂₉ NO ₂ =639.75) 1-18 m/z=681.25 (C ₅₀ H ₃₅ NS=681.9) 1-19 m/z=589.2 (C ₄₃ H ₂₇ NO ₂ =589.69) 1-20 m/z=664.25 (C ₄₉ H ₃₂ N ₂ O=664.81) 1-21 m/z=639.22 (C ₄₇ H ₂₉ NO ₂ =639.75) 1-22 m/z=605.18 (C ₄₃ H ₂₇ NOS=605.76) 1-23 m/z=605.2 (C ₄₃ H ₂₇ NO ₃ =605.69) 1-24 m/z=743.26 (C ₅₅ H ₃₇ NS=743.97) 1-25 m/z=661.2 (C ₄₅ H ₂₇ NOS ₂ =661.8) 1-26 m/z=687.21 (C ₄₈ H ₃₃ NS ₂ =687.92) 1-27 m/z=637.15 (C ₄₃ H ₂₇ NOS ₂ =637.82) 1-28 m/z=629.2 (C ₄₅ H ₂₇ NO ₃ =629.72) 1-29 m/z=704.25 (C ₅₁ H ₃₂ N ₂ O ₂ =704.83) 1-30 m/z=647.23 (C ₄₆ H ₃₃ NOS=647.84) 1-31 m/z=591.2 (C ₄₃ H ₂₉ NS=591.77) 1-32 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-33 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-34 m/z=641.22 (C ₄₇ H ₃₁ NS=641.83) 1-35 m/z=665.24 (C ₄₉ H ₃₁ NO ₂ =665.79) 1-36 m/z=682.24 (C ₄₉ H ₃₁ FN ₂ O=682.8) 1-37 m/z=641.22 (C ₄₇ H ₃₁ NS=641.83) 1-38 m/z=681.21 (C ₄₉ H ₃₁ NOS=681.85) 1-39 m/z=665.24 (C ₄₉ H ₃₁ NO ₂ =665.79) 1-40 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) 1-41 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) 1-42 m/z=565.19 (C ₄₁ H ₂₇ NS=565.73) 1-43 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-44 m/z=605.18 (C ₄₃ H ₂₇ NOS=605.76) 1-45 m/z=631.23 (C ₄₆ H ₃₃ NS=631.84) 1-46 m/z=667.23 (C ₄₉ H ₃₃ NS=667.87) 1-47 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-48 m/z=695.19 (C ₄₉ H ₂₉ NO ₂ S=695.84) 1-49 m/z=639.22 (C ₄₇ H ₂₉ NO ₂ =639.75) 1-50 m/z=641.22 (C ₄₇ H ₃₁ NS=641.83) 1-51 m/z=649.24 (C ₄₉ H ₃₁ NO=649.79) 1-52 m/z=639.2 (C ₄₇ H ₂₉ NS=639.82) 1-53 m/z=705.27 (C ₅₂ H ₃₅ NO ₂ =705.86) 1-54 m/z=707.26 (C ₅₂ H ₃₇ NS=707.94) 1-55 m/z=739.29 (C ₅₆ H ₃₇ NO=739.92) 1-56 m/z=737.27 (C ₅₆ H ₃₅ NO=737.9) 1-57 m/z=740.28 (C ₅₅ H ₃₆ N ₂ O=740.91) 1-58 m/z=681.21 (C ₄₉ H ₃₁ NOS=681.85) 1-59 m/z=631.25 (C ₄₆ H ₃₃ NO ₂ =631.78) 1-60 m/z=753.27 (C ₅₆ H ₃₅ NO ₂ =753.9) 1-61 m/z=845.28 (C ₆₂ H ₃₉ NOS=846.06) 1-62 m/z=753.27 (C ₅₆ H ₃₅ NO ₂ =753.9) 1-63 m/z=605.2 (C ₄₃ H ₂₇ NO ₃ =605.69) 1-64 m/z=706.3 (C ₅₂ H ₃₈ N ₂ O=706.89) 1-65 m/z=771.26 (C ₅₆ H ₃₇ NOS=771.98) 1-66 m/z=755.28 (C ₅₆ H ₃₇ NO ₂ =755.92) 1-67 m/z=655.21 (C ₄₇ H ₂₉ NO ₃ =655.75) 1-68 m/z=772.29 (C ₅₆ H ₄₀ N ₂ S=773.01) 1-69 m/z=697.24 (C ₅₀ H ₃₅ NOS=697.9) 1-70 m/z=687.17 (C ₄₇ H ₂₉ NOS ₂ =687.88) 1-71 m/z=680.25 (C ₄₉ H ₃₂ N ₂ O ₂ =680.81) 1-72 m/z=645.18 (C ₄₅ H ₂₇ NO ₂ S=645.78) 1-73 m/z=830.33 (C ₆₂ H ₄₂ N ₂ O=831.03) 1-74 m/z=641.22 (C ₄₇ H ₃₁ NS=641.83) 1-75 m/z=665.24 (C ₄₉ H ₃₁ NO ₂ =665.79) 1-76 m/z=681.21 (C ₄₉ H ₃₁ NOS=681.85) 1-77 m/z=665.24 (C ₄₉ H ₃₁ NO ₂ =665.79) 1-78 m/z=625.24 (C ₄₇ H ₃₁ NO=625.77) 1-79 m/z=504.22 (C ₃₇ H ₂₀ D ₅ NO=504.64) 1-80 m/z=631.29 (C ₄₇ H ₃₇ NO=631.82) 1-81 m/z=720.19 (C ₅₀ H ₂₈ N ₂ O ₂ S=720.85) 1-82 m/z=539.22 (C ₄₀ H ₂₉ NO=539.68) 1-83 m/z=529.2 (C ₃₈ H ₂₇ NO ₂ =529.64) 1-84 m/z=787.2 (C ₅₅ H ₃₃ NOS ₂ =788) 1-85 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-86 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) 1-87 m/z=576.22 (C ₄₂ H ₂₈ N ₂ O=576.7) 1-88 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-89 m/z=503.22 (C ₃₇ H ₂₁ D ₄ NO=503.64) 1-90 m/z=742.3 (C ₅₅ H ₃₈ N ₂ O=742.92) 1-91 m/z=772.25 (C ₅₅ H ₃₆ N ₂ OS=772.97) 1-92 m/z=716.28 (C ₅₃ H ₃₆ N ₂ O=716.88) 1-93 m/z=707.2 (C ₅₀ H ₃₃ N ₃ S=707.9) 1-94 m/z=772.25 (C ₅₅ H ₃₆ N ₂ OS=772.97) 1-95 m/z=858.36 (C ₆₄ H ₄₆ N ₂ O=859.09) 1-96 m/z=862.27 (C ₆₁ H ₃₈ N ₂ O ₂ S=863.05) 1-97 m/z=847.3 (C ₆₁ H ₄₁ N ₃ S=848.08) 1-98 m/z=772.25 (C ₅₅ H ₃₆ N ₂ OS=772.97) 1-99 m/z=844.35 (C ₆₃ H ₄₄ N ₂ O=845.06) 1-100 m/z=1042.29 (C ₇₃ H ₄₂ N ₂ O ₄ S=1043.21) 1-101 m/z=920.32 (C ₆₈ H ₄₄ N ₂ S=921.17) 1-102 m/z=820.2 (C ₅₅ H ₃₆ N ₂ S ₃ =821.09) 1-103 m/z=682.24 (C ₄₉ H ₃₄ N ₂ S=682.89) 1-104 m/z=848.29 (C ₆₁ H ₄₀ N ₂ OS=849.06) 1-105 m/z=766.3 (C ₅₇ H ₃₈ N ₂ O=766.94) 1-106 m/z=682.24 (C ₄₉ H ₃₄ N ₂ S=682.89) 1-107 m/z=834.31 (C ₆₁ H ₄₂ N ₂ S=835.08) 1-108 m/z=497.18 (C ₃₇ H ₂₃ NO=497.6) 1-109 m/z=667.23 (C ₄₉ H ₃₃ NS=667.87) 1-110 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) 1-111 m/z=727.29 (C ₅₅ H ₃₇ NO=727.91) 1-112 m/z=609.19 (C ₄₃ H ₂₈ FNS=609.76) 1-113 m/z=758.28 (C ₅₅ H ₃₈ N ₂ S=758.98) 1-114 m/z=742.3 (C ₅₅ H ₃₈ N ₂ O=742.92) 1-115 m/z=666.27 (C ₄₉ H ₃₄ N ₂ O=666.82) 1-116 m/z=792.31 (C ₅₉ H ₄₀ N ₂ O=792.98) 1-117 m/z=792.31 (C ₅₉ H ₄₀ N ₂ O=792.98) 1-118 m/z=808.29 (C ₅₉ H ₄₀ N ₂ S=809.04) 1-119 m/z=682.24 (C ₄₉ H ₃₄ N ₂ S=682.89) 1-120 m/z=864.26 (C ₆₁ H ₄₀ N ₂ S ₂ =865.13) 1-121 m/z=742.3 (C ₅₅ H ₃₈ N ₂ O=742.92) 1-122 m/z=858.36 (C ₆₄ H ₄₆ N ₂ O=859.09) 1-123 m/z=742.3 (C ₅₅ H ₃₈ N ₂ O=742.92) 1-124 m/z=756.28 (C ₅₅ H ₃₆ N ₂ O ₂ =756.91) 1-125 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) 1-126 m/z=516.17 (C ₃₆ H ₂₄ N ₂ S=516.66) 1-127 m/z=515.17 (C ₃₇ H ₂₅ NS=515.67) 1-128 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) 1-129 m/z=549.21 (C ₄₁ H ₂₇ NO=549.67) 1-130 m/z=549.21 (C ₄₁ H ₂₇ NO=549.67) 1-131 m/z=565.19 (C ₄₁ H ₂₇ NS=565.73) 1-132 m/z=641.22 (C ₄₇ H ₃₁ NS=641.83) 1-133 m/z=681.25 (C ₅₀ H ₃₅ NS=681.9) 1-134 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-135 m/z=625.24 (C ₄₇ H ₃₁ NO=625.77) 1-136 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-137 m/z=615.2 (C ₄₅ H ₂₉ NS=615.79) 1-138 m/z=565.19 (C ₄₁ H ₂₇ NS=565.73) 1-139 m/z=639.22 (C ₄₇ H ₂₉ NO ₂ =639.75) 1-140 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-141 m/z=605.18 (C ₄₃ H ₂₇ NOS=605.76) 1-142 m/z=621.16 (C ₄₃ H ₂₇ NS ₂ =621.82) 1-143 m/z=695.19 (C ₄₉ H ₂₉ NO ₂ S=695.84) 1-144 m/z=664.25 (C ₄₉ H ₃₂ N ₂ O=664.81) 1-145 m/z=664.25 (C ₄₉ H ₃₂ N ₂ O=664.81) 1-146 m/z=615.26 (C ₄₆ H ₃₃ NO=615.78) 1-147 m/z=796.29 (C ₅₈ H ₄₀ N ₂ S=797.03) 1-148 m/z=589.2 (C ₄₃ H ₂₇ NO ₂ =589.69) 1-149 m/z=766.3 (C ₅₇ H ₃₈ N ₂ O=766.94) 1-150 m/z=664.25 (C ₄₉ H ₃₂ N ₂ O=664.81) 1-151 m/z=772.25 (C ₅₅ H ₃₆ N ₂ OS=772.97) 1-152 m/z=831.32 (C ₆₁ H ₄₁ N ₃ O=832.02)

[ Synthesis example 2]

The compound (final product 2) represented by Formula (2) according to the present invention is synthesized as shown in Scheme 4 below, but is not limited thereto.

<Scheme 4>

{In Scheme 4, G ¹ is L ⁵ or L ⁶ , G ² is Ar ⁵ or Ar ⁶ , X ¹ to X ³ , L ⁴ to L ⁶ , Ar ⁴ to Ar ⁶ In Formula (1) As defined, Hal ³ and Hal ⁴ independently of each other are I, Br or Cl.}

I. Sub 3 Synthesis Example

of Sub 3-1 Synthesis example

4 in 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (CAS Registry Number: 10202-45-6) (20 g, 66.19 mmol) -Biphenylboronic acid (CAS Registry Number: 5122-94-1) (13.1 g, 66.19 mmol) was dissolved in THF (370 ml), Pd(PPh ₃ ) ₄ (3.8 g, 3.31 mmol), K ₂ CO ₃ ( 27.4 g, 198.57 mmol) and water (165 ml) were added and stirred under reflux. When the reaction is complete, the organic layer is concentrated after extraction with ether and water. The concentrated organic layer was dried over MgSO ₄ and concentrated once more. The final concentrate was passed through a silica gel column and recrystallized to obtain 20.8 g of a product. (yield 75%)

Sub 3-8's Synthesis example

(3-(pyridin-2-yl)phenyl)boronic acid (14.3 g, 72.43) in 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (20 g, 72.43 mmol) mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water were added, and 20.3 g of the product was synthesized in the same manner as in the Sub 3-1 synthesis method. (Yield 71%)

Sub 3-19's Synthesis example

2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (15 g, 49.64 mmol) in (9,9-dimethyl-9H-fluoren-3 -yl)boronic acid (11.8 g, 49.64 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water were added, and the same method as in Sub 3-1 synthesis method above. 15.7 g of the product was synthesized by this method. (yield 69%)

Sub 3-35's Synthesis example

2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol) in dibenzo[b,d]furan-2-ylboronic acid (28.1 g, 132.71 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water were added, and 30.8 g of the product was synthesized in the same manner as in the Sub 3-1 synthesis method. (Yield 65%)

The compound belonging to Sub 3 may be the following compounds, but is not limited thereto, and Table 4 below shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 3 .

compound FD-MS compound FD-MS Sub 3-1 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 3-2 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 3-3 m/z=393.1 (C ₂₅ H ₁₆ ClN ₃ =393.87) Sub 3-4 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 3-5 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 3-6 m/z=421.11 (C ₂₅ H ₁₆ ClN ₅ =421.89) Sub 3-7 m/z=575.16 (C ₃₅ H ₂₂ ClN ₇ =576.06) Sub 3-8 m/z=394.1 (C ₂₄ H ₁₅ ClN ₄ =394.86) Sub 3-9 m/z=421.11 (C ₂₅ H ₁₆ ClN ₅ =421.89) Sub 3-10 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 3-11 m/z=503.21 (C ₃₃ H ₃₀ ClN ₃ =504.07) Sub 3-12 m/z=525.11 (C ₃₃ H ₂₀ ClN ₃ S=526.05) Sub 3-13 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub 3-14 m/z=568.17 (C ₄₀ H ₂₅ ClN ₂ =569.1) Sub 3-15 m/z=569.17 (C ₃₉ H ₂₄ ClN ₃ =570.09) Sub 3-16 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 3-17 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub 3-18 m/z=583.18 (C ₄₀ H ₂₆ ClN ₃ =584.12) Sub 3-19 m/z=461.17 (C ₃₀ H ₂₄ ClN ₃ =461.99) Sub 3-20 m/z=418.12 (C ₂₈ H ₁₉ ClN ₂ =418.92) Sub 3-21 m/z=420.11 (C ₂₆ H ₁₇ ClN ₄ =420.9) Sub 3-22 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub 3-23 m/z=459.15 (C ₃₀ H ₂₂ ClN ₃ =459.98) Sub 3-24 m/z=507.15 (C ₃₄ H ₂₂ ClN ₃ =508.02) Sub 3-25 m/z=519.15 (C ₃₅ H ₂₂ ClN ₃ =520.03) Sub 3-26 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 3-27 m/z=266.06 (C ₁₆ H ₁₁ ClN ₂ =266.73) Sub 3-28 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub 3-29 m/z=355.09 (C ₂₂ H ₁₄ ClN ₃ =355.83) Sub 3-30 m/z=470.13 (C ₃₀ H ₁₉ ClN ₄ =470.96) Sub 3-31 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 3-32 m/z=545.17 (C ₃₇ H ₂₄ ClN ₃ =546.07) Sub 3-33 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 3-34 m/z=269.05 (C ₁₃ H ₈ ClN ₅ =269.69) Sub 3-35 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub 3-36 m/z=420.11 (C ₂₆ H ₁₇ ClN ₄ =420.9) Sub 3-37 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub 3-38 m/z=368.08 (C ₂₂ H ₁₃ ClN ₄ =368.82) Sub 3-39 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 3-40 m/z=395.09 (C ₂₃ H ₁₄ ClN ₅ =395.85) Sub 3-41 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub 3-42 m/z=369.08 (C ₂₁ H ₁₂ ClN ₅ =369.81) Sub 3-43 m/z=469.11 (C ₂₉ H ₁₆ ClN ₅ =469.93) Sub 3-44 m/z=581.17 (C ₄₀ H ₂₄ ClN ₃ =582.1) Sub 3-45 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 3-46 m/z=449.08 (C ₂₇ H ₁₆ ClN ₃ S=449.96) Sub 3-47 m/z=495.15 (C ₃₃ H ₂₂ ClN ₃ =496.01) Sub 3-48 m/z=449.08 (C ₂₇ H ₁₆ ClN ₃ S=449.96)

II. Sub 4 Synthesis Example

Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.

<Scheme 5>

{In Scheme 5, Hal ⁵ is I, Br, or Cl.}

of Sub 4-2 Synthesis example

bis(pinacolato)diboron (7.1 g, 27.89 mmol) in 4-bromo-1,1'-biphenyl (5 g, 21.45 mmol), PdCl ₂ (dppf). (0.78 g, 1.07 mmol), KOAc (6.3 g, 64.35 mmol) and DMF (270 ml) were added, and the mixture was stirred and refluxed at 120°C. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 3.4 g (80%) of Sub 4-2.

Sub 4-37 Synthesis example

Add 2-bromodibenzo[b,d]furan (10 g, 40.47 mmol) bis(pinacolato)diboron (13.3 g, 52.61 mmol), PdCl ₂ (dppf) _, (0.05 equiv), KOAc (3 equiv), anhydrous DMF and 7 g of the product was synthesized in the same manner as in the Sub 4-2 synthesis method. (yield 82%)

The compound belonging to Sub 4 may be the following compounds, but is not limited thereto, and Table 5 below shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 4 above.

compound FD-MS compound FD-MS Sub 4-1 m/z=122.05 (C ₆ H ₇ BO ₂ =121.93) Sub 4-2 m/z=198.09 (C ₁₂ H ₁₁ BO ₂ =198.03) Sub 4-3 m/z=172.07 (C ₁₀ H ₉ BO ₂ =171.99) Sub 4-4 m/z=172.07 (C ₁₀ H ₉ BO ₂ =171.99) Sub 4-5 m/z=274.12 (C ₁₈ H ₁₅ BO ₂ =274.13) Sub 4-6 m/z=198.09 (C ₁₂ H ₁₁ BO ₂ =198.03) Sub 4-7 m/z=248.1 (C ₁₆ H ₁₃ BO ₂ =248.09) Sub 4-8 m/z=222.09 (C ₁₄ H ₁₁ BO ₂ =222.05) Sub 4-9 m/z=246.09 (C ₁₆ H ₁₁ BO ₂ =246.07) Sub 4-10 m/z=399.14 (C ₂₇ H ₁₈ BNO ₂ =399.26) Sub 4-11 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 4-12 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 4-13 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 4-14 m/z=199.08 (C ₁₁ H ₁₀ BNO ₂ =199.02) Sub 4-15 m/z=199.08 (C ₁₁ H ₁₀ BNO ₂ =199.02) Sub 4-16 m/z=240.13 (C ₁₅ H ₁₇ BO ₂ =240.11) Sub 4-17 m/z=248.1 (C ₁₆ H ₁₃ BO ₂ =248.09) Sub 4-18 m/z=222.09 (C ₁₄ H ₁₁ BO ₂ =222.05) Sub 4-19 m/z=224.08 (C ₁₂ H ₉ BN ₂ O ₂ =224.03) Sub 4-20 m/z=224.08 (C ₁₂ H ₉ BN ₂ O ₂ =224.03) Sub 4-21 m/z=350.15 (C ₂₄ H ₁₉ BO ₂ =350.22) Sub 4-22 m/z=374.15 (C ₂₆ H ₁₉ BO ₂ =374.25) Sub 4-23 m/z=272.1 (C ₁₈ H ₁₃ BO ₂ =272.11) Sub 4-24 m/z=174.06 (C ₈ H ₇ BN ₂ O ₂ =173.97) Sub 4-25 m/z=174.06 (C ₈ H ₇ BN ₂ O ₂ =173.97) Sub 4-26 m/z=223.08 (C ₁₃ H ₁₀ BNO ₂ =223.04) Sub 4-27 m/z=238.12 (C ₁₅ H ₁₅ BO ₂ =238.09) Sub 4-28 m/z=238.12 (C ₁₅ H ₁₅ BO ₂ =238.09) Sub 4-29 m/z=362.15 (C ₂₅ H ₁₉ BO ₂ =362.24) Sub 4-30 m/z=360.13 (C ₂₅ H ₁₇ BO ₂ =360.22) Sub 4-31 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 4-32 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 4-33 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 4-34 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 4-35 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 4-36 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 4-37 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 4-38 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 4-39 m/z=306.06 (C ₁₆ H ₁₁ BN ₂ O ₂ S=306.15) Sub 4-40 m/z=290.09 (C ₁₆ H ₁₁ BN ₂ O ₃ =290.09) Sub 4-41 m/z=443.14 (C ₂₇ H ₁₈ BN ₃ O ₃ =443.27) Sub 4-42 m/z=288.1 (C ₁₈ H ₁₃ BO ₃ =288.11) Sub 4-43 m/z=304.07 (C ₁₈ H ₁₃ BO ₂ S=304.17) Sub 4-44 m/z=304.07 (C ₁₈ H ₁₃ BO ₂ S=304.17) Sub 4-45 m/z=578.24 (C ₄₂ H ₃₁ BO ₂ =578.52) Sub 4-46 m/z=424.16 (C ₃₀ H ₂₁ BO ₂ =424.31) Sub 4-47 m/z=378.11 (C ₂₄ H ₁₅ BO ₄ =378.19) Sub 4-48 m/z=256.07 (C ₁₂ H ₁₀ B ₂ O ₅ =255.83)

III. Final Product 2 Synthesis Example

Sub 3 (1 equivalent) and Sub 4 (1~2 equivalent) were put in a round flask and dissolved in THF, followed by Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv) and water were added and stirred and refluxed. After the reaction was completed, the organic layer was extracted with ether and water, dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized using silicagel column to obtain Final product 2.

2-9's Synthesis example

Dissolve Sub 4-36 (2.8 g, 13.1 mmol) in THF (70 ml) in Sub 3-1 (5 g, 11.91 mmol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol), K ₂ CO ₃ (5 g, 35.73 mmol) and water (30 ml) were added and stirred under reflux. When the reaction is complete, the organic layer is concentrated after extraction with ether and water. The concentrated organic layer was dried over MgSO ₄ and concentrated once more. The final concentrate was passed through a silica gel column and recrystallized to obtain 5.4 g of a product. (Yield 71%)

2-29's Synthesis example

Sub 3-39 (4 g, 14.94 mmol) to Sub 4-47 (6.2 g, 16.43 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water was added and 8.1 g of the product was synthesized in the same manner as in the above 2-9 synthesis method. (Yield 84%)

2-62's Synthesis example

Sub 3-33 (4 g, 10.7 mmol) to Sub 4-32 (2.7 g, 11.8 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water was added and 4.4 g of the product was synthesized in the same manner as in the above 2-9 synthesis method. (yield 80%)

2-115 Synthesis example

Sub 3-41 (10 g, 37.35 mmol) to Sub 4-48 (4.7 g, 18.5 mmol), Pd(PPh ₃ ) ₄ (0.1 equiv), K ₂ CO ₃ (6 equiv), anhydrous THF and a small amount of water was added and 9.1 g of the product was synthesized in the same manner as in the above 2-9 synthesis method. (yield 78%)

Meanwhile, FD-MS values of compounds 2-1 to 2-333 of the present invention prepared according to the above synthesis examples are shown in Table 6 below.

compound FD-MS compound FD-MS 2-1 m/z=399.14 (C ₂₇ H ₁₇ N ₃ O=399.45) 2-2 m/z=415.11 (C ₂₇ H ₁₇ N ₃ S=415.51) 2-3 m/z=474.18 (C ₃₃ H ₂₂ N ₄ =474.57) 2-4 m/z=449.15 (C ₃₁ H ₁₉ N ₃ O=449.51) 2-5 m/z=449.15 (C ₃₁ H ₁₉ N ₃ O=449.51) 2-6 m/z=515.15 (C ₃₅ H ₂₁ N ₃ S=515.63) 2-7 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 2-8 m/z=499.17 (C ₃₅ H ₂₁ N ₃ O=499.57) 2-9 m/z=551.2 (C ₃₉ H ₂₅ N ₃ O=551.65) 2-10 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 2-11 m/z=702.28 (C ₅₁ H ₃₄ N ₄ =702.86) 2-12 m/z=657.22 (C ₄₆ H ₃₁ N ₃ S=657.84) 2-13 m/z=551.2 (C ₃₉ H ₂₅ N ₃ O=551.65) 2-14 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 2-15 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 2-16 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 2-17 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 2-18 m/z=591.18 (C ₄₁ H ₂₅ N ₃ S=591.73) 2-19 m/z=627.24 (C ₄₄ H ₂₉ N ₅ =627.75) 2-20 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 2-21 m/z=551.2 (C ₃₉ H ₂₅ N ₃ O=551.65) 2-22 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 2-23 m/z=702.28 (C ₅₁ H ₃₄ N ₄ =702.86) 2-24 m/z=474.18 (C ₃₃ H ₂₂ N ₄ =474.57) 2-25 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.94) 2-26 m/z=731.24 (C ₅₂ H ₃₃ N ₃ S=731.92) 2-27 m/z=601.23 (C ₄₂ H ₂₇ N ₅ =601.71) 2-28 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 2-29 m/z=641.21 (C ₄₅ H ₂₇ N ₃ O ₂ =641.73) 2-30 m/z=746.21 (C ₅₁ H ₃₀ N ₄ OS=746.89) 2-31 m/z=716.26 (C ₅₁ H ₃₂ N ₄ O=716.84) 2-32 m/z=681.19 (C ₄₇ H ₂₇ N ₃ OS=681.81) 2-33 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 2-34 m/z=491.15 (C ₃₃ H ₂₁ N ₃ S=491.61) 2-35 m/z=550.22 (C ₃₉ H ₂₆ N ₄ =550.67) 2-36 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 2-37 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 2-38 m/z=491.15 (C ₃₃ H ₂₁ N ₃ S=491.61) 2-39 m/z=704.27 (C ₄₉ H ₃₂ N ₆ =704.84) 2-40 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 2-41 m/z=551.2 (C ₃₉ H ₂₅ N ₃ O=551.65) 2-42 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 2-43 m/z=626.25 (C ₄₅ H ₃₀ N ₄ =626.76) 2-44 m/z=676.26 (C ₄₉ H ₃₂ N ₄ =676.82) 2-45 m/z=551.2 (C ₃₉ H ₂₅ N ₃ O=551.65) 2-46 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 2-47 m/z=614.25 (C ₄₄ H ₃₀ N ₄ =614.75) 2-48 m/z=575.17 (C ₃₉ H ₂₁ N ₅ O=575.63) 2-49 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 2-50 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 2-51 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 2-52 m/z=625.22 (C ₄₅ H ₂₇ N ₃ O=625.73) 2-53 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 2-54 m/z=591.18 (C ₄₁ H ₂₅ N ₃ S=591.73) 2-55 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 2-56 m/z=693.22 (C ₄₉ H ₃₁ N ₃ S=693.87) 2-57 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.6) 2-58 m/z=641.21 (C ₄₅ H ₂₇ N ₃ O ₂ =641.73) 2-59 m/z=571.12 (C ₃₇ H ₂₁ N ₃ S ₂ =571.72) 2-60 m/z=564.2 (C ₃₉ H ₂₄ N ₄ O=564.65) 2-61 m/z=581.16 (C ₃₉ H ₂₃ N ₃ OS=581.69) 2-62 m/z=521.1 (C ₃₃ H ₁₉ N ₃ S ₂ =521.66) 2-63 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 2-64 m/z=640.23 (C ₄₅ H ₂₈ N ₄ O=640.75) 2-65 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 2-66 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.6) 2-67 m/z=580.17 (C ₃₉ H ₂₄ N ₄ S=580.71) 2-68 m/z=564.2 (C ₃₉ H ₂₄ N ₄ O=564.65) 2-69 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 2-70 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.6) 2-71 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.6) 2-72 m/z=639.24 (C ₄₅ H ₂₉ N ₅ =639.76) 2-73 m/z=607.21 (C ₄₂ H ₂₉ N ₃ S=607.78) 2-74 m/z=715.26 (C ₅₂ H ₃₃ N ₃ O=715.86) 2-75 m/z=640.23 (C ₄₅ H ₂₈ N ₄ O=640.75) 2-76 m/z=707.2 (C ₄₉ H ₂₉ N ₃ OS=707.85) 2-77 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.71) 2-78 m/z=617.28 (C ₄₅ H ₃₅ N ₃ =617.8) 2-79 m/z=653.25 (C ₄₇ H ₃₁ N ₃ O=653.79) 2-80 m/z=733.22 (C ₅₁ H ₃₁ N ₃ OS=733.89) 2-81 m/z=615.19 (C ₄₃ H ₂₅ N ₃ O ₂ =615.69) 2-82 m/z=681.19 (C ₄₇ H ₂₇ N ₃ OS=681.81) 2-83 m/z=716.29 (C ₅₂ H ₃₆ N ₄ =716.89) 2-84 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 2-85 m/z=641.25 (C ₄₆ H ₃₁ N ₃ O=641.77) 2-86 m/z=693.22 (C ₄₉ H ₃₁ N ₃ S=693.87) 2-87 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 2-88 m/z=631.17 (C ₄₃ H ₂₅ N ₃ OS=631.75) 2-89 m/z=595.14 (C ₃₉ H ₂₁ N ₃ O ₂ S=595.68) 2-90 m/z=659.24 (C ₄₅ H ₂₁ D ₅ N ₄ O ₂ =659.76) 2-91 m/z=637.16 (C ₄₂ H ₂₇ N ₃ S ₂ =637.82) 2-92 m/z=729.25 (C ₅₁ H ₃₁ N ₅ O=729.84) 2-93 m/z=578.17 (C ₃₉ H ₂₂ N ₄ O ₂ =578.63) 2-94 m/z=746.21 (C ₅₁ H ₃₀ N ₄ OS=746.89) 2-95 m/z=681.24 (C ₄₈ H ₃₁ N ₃ O ₂ =681.8) 2-96 m/z=762.19 (C ₅₁ H ₃₀ N ₄ S ₂ =762.95) 2-97 m/z=436.17 (C ₃₀ H ₂₀ N ₄ =436.52) 2-98 m/z=437.16 (C ₂₉ H ₁₉ N ₅ =437.51) 2-99 m/z=513.2 (C ₃₅ H ₂₃ N ₅ =513.6) 2-100 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.7) 2-101 m/z=486.18 (C ₃₄ H ₂₂ N ₄ =486.58) 2-102 m/z=527.17 (C ₃₅ H ₂₁ N ₅ O=527.59) 2-103 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.7) 2-104 m/z=502.18 (C ₃₄ H ₂₂ N ₄ O=502.58) 2-105 m/z=511.2 (C ₃₇ H ₂₅ N ₃ =511.63) 2-106 m/z=563.21 (C ₃₉ H ₂₅ N ₅ =563.66) 2-107 m/z=511.2 (C ₃₇ H ₂₅ N ₃ =511.63) 2-108 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.7) 2-109 m/z=513.2 (C ₃₅ H ₂₃ N ₅ =513.6) 2-110 m/z=462.16 (C ₃₀ H ₁₈ N ₆ =462.52) 2-111 m/z=612.21 (C ₄₂ H ₂₄ N ₆ =612.7) 2-112 m/z=499.2 (C ₃₆ H ₂₅ N ₃ =499.62) 2-113 m/z=569.17 (C ₃₇ H ₂₃ N ₅ S=569.69) 2-114 m/z=629.22 (C ₄₃ H ₂₇ N ₅ O=629.72) 2-115 m/z=629.22 (C ₄₃ H ₂₇ N ₅ O=629.72) 2-116 m/z=563.21 (C ₃₉ H ₂₅ N ₅ =563.66) 2-117 m/z=565.2 (C ₃₇ H ₂₃ N ₇ =565.64) 2-118 m/z=630.22 (C ₄₂ H ₂₆ N ₆ O=630.71) 2-119 m/z=511.2 (C ₃₇ H ₂₅ N ₃ =511.6) 2-120 m/z=561.2 (C ₄₁ H ₂₇ N ₃ =561.7) 2-121 m/z=561.2 (C ₄₁ H ₂₇ N ₃ =561.7) 2-122 m/z=535.2 (C ₃₉ H ₂₅ N ₃ =535.7) 2-123 m/z=611.2 (C ₄₅ H ₂₉ N ₃ =611.7) 2-124 m/z=611.2 (C ₄₅ H ₂₉ N ₃ =611.7) 2-125 m/z=611.2 (C ₄₅ H ₂₉ N ₃ =611.7) 2-126 m/z=561.2 (C ₄₁ H ₂₇ N ₃ =561.7) 2-127 m/z=611.2 (C ₄₅ H ₂₉ N ₃ =611.7) 2-128 m/z=585.2 (C ₄₃ H ₂₇ N ₃ =585.7) 2-129 m/z=561.2 (C ₄₁ H ₂₇ N ₃ =561.7) 2-130 m/z=637.3 (C ₄₇ H ₃₁ N ₃ =637.8) 2-131 m/z=585.2 (C ₄₃ H ₂₇ N ₃ =585.7) 2-132 m/z=661.3 (C ₄₉ H ₃₁ N ₃ =661.8) 2-133 m/z=475.2 (C ₃₃ H ₂₁ O=475.6)

Manufacturing evaluation of organic electric devices

[ Example One] red organic light emitting device (Phosphor Host)

An organic electroluminescent device was manufactured according to a conventional method by using the compound obtained through synthesis as a light emitting host material of the light emitting layer. First, on an ITO layer (anode) formed on a glass substrate, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1 After vacuum deposition of a ,4-diamine (abbreviated as 2-TNATA) film to form a 60 nm-thick hole injection layer, 4,4-bis[N-(1-naphthyl) as a hole transport compound on the hole injection layer -N-phenylamino]biphenyl (abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. As a host on the hole transport layer, a host material was used in a ratio (5:5) of Compound 1-5 and Compound 2-4 represented by Formulas (1) to (2), and (piq)2Ir ( acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was doped at a weight ratio of 95:5 to deposit an emission layer with a thickness of 30 nm. Subsequently, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, and an electron transport layer Tris(8-quinolinol)aluminum (abbreviated as Alq3) was deposited with a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

[ Example 2] to [ Example 32]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 7 were used instead of compounds 1-5 and 2-4 of the present invention as the host material of the light emitting layer.

[ comparative example 1] and [ comparative example 8]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compounds 2-4 to Compound 2-126 of the present invention were used as a single material as a host material for the emission layer.

[ comparative example 9]

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound 2-133 of the present invention and Comparative Compound A were used instead of Compound 1-5 and Compound 2-4 of the present invention as the host material of the light emitting layer. did

[Compound 2-133] [Comparative Compound A]

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 32 and Comparative Examples 1 to 9 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch. and T95 lifespan was measured using the life measuring equipment of McScience at 2500cd/m ² standard luminance. The measurement results are shown in Table 7 below.

first compound second compound drive voltage electric current
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T
(95) CIE x y Comparative Example (1) 2-4 - 5.1 13.2 2500.0 18.9 87.4 0.61 0.33 Comparative Example (2) 2-9 - 5.1 13.4 2500.0 18.6 85.7 0.61 0.32 Comparative Example (3) 2-24 - 5.3 12.6 2500.0 19.8 90.5 0.62 0.33 Comparative Example (4) 2-62 - 5.0 13.8 2500.0 18.1 84.8 0.61 0.30 Comparative Example (5) 2-89 - 5.0 14.0 2500.0 17.8 81.2 0.60 0.31 Comparative Example (6) 2-98 - 4.9 14.1 2500.0 17.7 80.4 0.63 0.35 Comparative Example (7) 2-124 - 5.2 13.0 2500.0 19.3 88.1 0.64 0.30 Comparative Example (8) 2-126 - 5.2 12.3 2500.0 20.4 88.4 0.60 0.34 Comparative Example (9) 2-133 Comparative compound A 5.2 13.7 2500.0 18.2 90.8 0.64 0.34 Example (1) 2-4 1-5 4.9 8.5 2500.0 29.4 122.0 0.62 0.30 Example (2) 1-17 4.9 8.4 2500.0 29.7 120.8 0.60 0.33 Example (3) 1-39 4.8 8.6 2500.0 29.2 120.2 0.62 0.30 Example (4) 1-53 4.8 8.4 2500.0 29.8 119.0 0.64 0.35 Example (5) 2-9 1-11 4.9 8.4 2500.0 29.7 118.7 0.62 0.32 Example (6) 1-46 4.9 8.5 2500.0 29.3 121.6 0.63 0.31 Example (7) 1-96 4.8 8.7 2500.0 28.7 117.5 0.62 0.33 Example (8) 1-136 5.0 8.7 2500.0 28.8 120.4 0.64 0.33 Example (9) 2-24 1-5 5.1 8.4 2500.0 29.6 124.8 0.65 0.34 Example (10) 1-17 5.0 8.4 2500.0 29.9 123.6 0.62 0.30 Example (11) 1-39 5.0 8.5 2500.0 29.5 123.0 0.64 0.30 Example (12) 1-53 5.0 8.3 2500.0 30.1 121.8 0.63 0.32 Example (13) 2-62 1-5 4.9 8.7 2500.0 28.9 120.1 0.60 0.34 Example (14) 1-17 4.8 8.6 2500.0 29.2 118.9 0.61 0.30 Example (15) 1-39 4.8 8.7 2500.0 28.7 118.3 0.65 0.34 Example (16) 1-53 4.8 8.5 2500.0 29.3 117.1 0.62 0.32 Example (17) 2-89 1-11 4.8 8.6 2500.0 29.2 116.8 0.62 0.35 Example (18) 1-46 4.8 8.7 2500.0 28.8 119.7 0.61 0.30 Example (19) 1-96 4.7 8.9 2500.0 28.2 115.6 0.63 0.30 Example (20) 1-136 4.8 8.8 2500.0 28.3 118.5 0.65 0.33 Example (21) 2-98 1-11 4.8 8.6 2500.0 29.0 115.8 0.62 0.32 Example (22) 1-46 4.7 8.8 2500.0 28.5 118.8 0.60 0.32 Example (23) 1-96 4.7 8.9 2500.0 27.9 114.6 0.63 0.31 Example (24) 1-136 4.8 8.9 2500.0 28.1 117.6 0.63 0.32 Example (25) 2-124 1-11 5.0 8.2 2500.0 30.4 120.5 0.61 0.35 Example (26) 1-46 5.0 8.3 2500.0 30.0 123.5 0.61 0.35 Example (27) 1-96 4.9 8.5 2500.0 29.4 119.4 0.60 0.33 Example (28) 1-136 5.0 8.5 2500.0 29.6 122.3 0.64 0.31 Example (29) 2-126 1-5 5.1 8.3 2500.0 30.1 123.9 0.61 0.30 Example (30) 1-17 5.0 8.2 2500.0 30.4 122.7 0.64 0.32 Example (31) 1-39 5.0 8.3 2500.0 30.0 122.1 0.62 0.35 Example (32) 1-53 5.0 8.2 2500.0 30.5 120.9 0.60 0.33

As can be seen from the results in Table 7, when a mixture of compounds (1) to (2) of the present invention is used as a light emitting layer material, the driving voltage is lowered and the efficiency and efficiency are lower than when a single material of compound (2) is used. It can be seen that the lifespan is significantly improved. In addition, the device characteristics were improved in the case of the combination of Example 9 of the present invention, compared to Comparative Example 9 using Comparative Compound A having different core elements of Compound (1) and Compound 2-133 of the present invention.

The difference from Comparative Examples 1 to 8 is that a single material and a mixture material are used. When the mixture of the present invention is used, the band gap (HOMO-LUMO) is narrower than when a single material is used. This effect is that as the compound of compound (1) having hole properties and compound (2) having electronic properties are mixed, the HOMO level of compound (1) affects the HOMO level of the entire mixture, and the HOMO level of this energy level The change will greatly affect the overall device.

The narrow band gap improves the hole and electron injection characteristics into the dopant, and helps to improve overall efficiency and lifespan.

In the case of N, which is the element used in Comparative Example 9, the chemical stability is lower than that of O and S of the present invention, and the driving voltage, efficiency, and lifespan are adversely affected due to the deterioration of the plate shape due to the secondary substituent.

The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications within the scope without departing from the essential characteristics of the present invention. 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 interpreted 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: 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 generating layer
361: second charge generating 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 : 1st stack ST2 : 2nd stack

Claims (16)

In an organic electric device comprising a lower first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the organic material layer includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer, and the formula (1) And an organic electric device comprising a compound represented by the formula (2)
Formula (1) Formula (2)

{In the above formulas (1) and (2),
1) X is O or S;
2) X ¹ , X ² and X ³ are each independently C(R ₁ ) or N, provided that at least one of X ¹ , X ² and X ³ is N,
3) R ¹ , R ² , R ³ , R ⁴ and R ₁ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl 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 ); to form a ring,
4) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si, and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; is selected from the group consisting of, wherein R ^a and R ^b are each independently C ₆ ~ C an aryl group of ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; is selected from the group consisting of,
5) a, b, c and d are each independently an integer of 0 to 4,
6) i and j are each independently an integer of 0 to 2, with the proviso that i+j is an integer of 1 or more,
7) 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; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring is selected from the group consisting of,
8) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ 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; selected from the group consisting of, or adjacent groups may combine with each other to form a ring,
9) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkoxyl group and 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 Alkoxy 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; and a C ₈ ~ C ₂₀ arylalkenyl group; 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' is C ₃ ~ C ₆₀ of an aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or a C ₂ ~ C ₆₀ heterocyclic ring or a fused ring consisting of a combination thereof, including saturated or unsaturated rings.}
The organic electric device according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (9).
Chemical formula (3) Chemical formula (4) Chemical formula (5)

Formula (6) Formula (7)

Formula (8) Formula (9)

{In the above formulas (3) to (9),
1) X, R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are the same as defined in claim 1 above and
2) a', b', c' and d' are independently integers from 0 to 3, and b" and d" are independently integers from 0 to 2.}
The organic electric device according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula (10) or formula (11)
Formula (10) Formula (11)

{In Formulas (10) and (11), R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , i and j are the same as defined in claim 1 above.}
The organic electric device according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula (12) or (13)
Formula (12) Formula (13)

{In the above formula (12) or formula (13),
1) X, R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , L ² , Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , i and j in claim 1 above same as defined,
2) Ring A is a C ₁₀ ~ C ₂₀ aryl group; Or C ₁₀ ~ C ₂₀ A heterocyclic group; and
3) a" and c" are each independently an integer from 0 to 10.}
The organic electric device according to claim 1, wherein at least one of Ar ¹ , Ar ² , Ar ³ and Ar ⁴ is represented by the following formula (B-1).
Formula (B-1)

{In the formula B-1,
1) Ring D and ring E are each independently a C ₆ ~ C ₂₀ aryl group; Or C ₄ ~ C ₂₀ A heterocyclic group; and
2) V ¹ and V ² are each independently a single bond, NR ^c , CR ^d R ^e , O or S,
3) R ^c , R ^d and R ^e are each independently a C ₆ ~ C ₆₀ aryl 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; and a C ₆ ~ C ₃₀ aryloxy group; selected from the group consisting of, or R ^d and R ^e may be bonded to each other to form a ring,
4)

indicates the position where it is bound.}
According to claim 1, wherein the compound represented by the formula (1) is an organic electric device, characterized in that any one of the following compounds

The organic electric device according to claim 1, wherein at least one of Ar ⁵ , Ar ⁶ and Ar ⁷ is represented by any one of the following Chemical Formulas (2-1) to (2-6).
Formula (2-1) Formula (2-2) Formula (2-3)

Formula (2-4) Formula (2-5) Formula (2-6)

{In the above formulas (2-1) to (2-6),
1) X ¹² and X ¹³ are each independently NL ⁶ -Ar ⁸ , O, S, C(R ₂ ) or CR'R",
2) The R ₂ , R′, R″, R ⁵ and R ⁶ are the same or different from each other, and each independently hydrogen; deuterium; halogen; C ₁ ~ C ₂₀ Alkyl group or C ₆ ~ C ₂₀ Aryl group substituted or unsubstituted silane group; cyano group; nitro group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₂₀ aryloxy 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; Fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ Hetero It ^may be selected from _the ^{group consisting} of a _cyclic ^group ; or R' and R" may combine with each other to form a spy ring,
3) L ⁶ is the same as the definition of L ¹ in claim 1,
4) Ar ⁸ is the same as the definition of Ar ¹ in claim 1,
5) e and f are each independently an integer from 0 to 4, and f' is an integer from 0 to 6.}
The organic electric device according to claim 1, wherein the compound represented by the formula (2) is represented by any one of the following formulas (2-7) to (2-9).
Formula (2-7) Formula (2-8)

Formula (2-9)

{In the above formulas (2-7) to (2-9),
1) X ³ , L ³ , L ⁴ , L ⁵ , Ar ⁶ and Ar ⁷ are the same as defined in claim 1 above,
2) R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same as defined for R ⁵ in claim 7,
3) e, f, g, h, k and l are each independently an integer from 0 to 4.}
The organic electric device according to claim 1, wherein the compound represented by the formula (2) is represented by any one of the following formulas (2-10) to (2-12):
Formula (2-10) Formula (2-11)

Formula (2-12)

{In the above formulas (2-10) to (2-12),
1) X ³ , L ³ , L ⁴ , L ⁵ , Ar ⁶ and Ar ⁷ are the same as defined in claim 1 above,
2) X ¹² , X ¹⁴ and X ¹⁵ are the same as the definition of X ¹² in claim 7,
3) R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same as defined for R ⁵ in claim 7,
4) e, h and k are independently integers from 0 to 4, and f", g' and l' are independently integers from 0 to 3.}
The organic electric device according to claim 1, wherein L ¹ , L ² , L ³ , L ⁴ or L ⁵ is represented by any one of the following Chemical Formulas (b-1) to (b-13).
Formula (b-1) Formula (b-2) Formula (b-3) Formula (b-4) Formula (b-5)

Formula (b-6) Formula (b-7) Formula (b-8) Formula (b-9)

Formula (b-10) Formula (b-11) Formula (b-12) Formula (b-13)

{In the above formulas (b-1) to (b-13),
1) Z is O, S, NL ⁷ -Ar ⁹ or CR ^f R ^g ,
2) L ⁷ is the same as the definition of L ¹ in claim 1,
3) Ar ⁹ is the same as the definition of Ar ¹ in claim 1,
4) R ¹¹ , R ¹² and R ¹³ are the same as defined for R ¹ in claim 1,
5) R ^f and R ^g are the same as the definition of R ^c in claim 5 above,
6) m, o and p are each independently an integer from 0 to 4, n is an integer from 0 to 6, q and r are independently from each other an integer from 0 to 3, s is an integer from 0 to 2, t is 0 or 1,
7) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently of each other CR ^h or N, provided that at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,
8) wherein R ^h is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl 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; and a C ₆ ~ C ₃₀ aryloxy group; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring.}
According to claim 1, wherein the compound represented by the formula (2) is an organic electric device, characterized in that any one of the following compounds

The organic electric device according to claim 1, further comprising a light efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer among one surface of the first electrode and the second electrode.
The organic electric device according to claim 1, wherein the organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.
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 15, 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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