WO2016137148A1 - Novel compound for organic electronic element, organic electronic element using same, and electronic device thereof - Google Patents

Abstract

The present invention provides: a novel compound capable of improving the light emission efficiency, safety, and lifespan of an element; an organic electronic element using the same; and an electronic device thereof.

Description

Novel Compounds for Organic Electrical Devices, Organic Electrical Devices and Electronic Devices Using the Same

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

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

The material used as the organic material layer in the organic electric element 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 and the like according to a function.

The biggest problem for organic electroluminescent devices is life and efficiency. As the display becomes larger, such efficiency and life problems must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase the life.

However, simply improving the organic material layer does not maximize the efficiency. This is because a long life and high efficiency can be achieved at the same time when an optimal combination of energy level, T1 value, and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

In addition, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary according to each light emitting layer (R, G, B). It is time to develop the floor.

In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.

However, the material used in the hole transport layer has a low TMO value because it has to have a low HOMO value, which causes the exciton generated in the light emitting layer to pass to the hole transport layer, resulting in charge unbalance in the light emitting layer. This causes light emission at the hole transport layer interface.

When emitting light at the hole transport layer interface, the color purity and efficiency of the organic electric element is reduced and the life is shortened. Therefore, the development of a light emitting auxiliary layer having a high T1 value and a HOMO level between the hole transport layer HOMO energy level and the light emitting layer HOMO energy level is urgently required.

On the other hand, while delaying the penetration of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. 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 the property of lowering the uniformity of the surface of the thin film when the device is driven, which has been reported to have a great influence on the device life. In addition, the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.

That is, in order to fully exhibit the excellent characteristics of the organic electric device, the materials 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 material, Supported by the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials continues to be required, and in particular, the development of materials for the light emitting auxiliary layer and the hole transport layer is urgently required.

Embodiments of the present invention to solve the problems of the above-described background, the discovery of a compound having a novel structure, and also when the compound is applied to an organic electric device greatly improve the luminous efficiency, stability and life of the device It turns out that you can.

Accordingly, an object of the present invention is to provide a novel compound, an organic electric device, and an electronic device using the same.

The present invention provides a compound represented by the following formula.

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

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 life of the device can be greatly improved.

1 is an exemplary view of an organic electroluminescent device according to the present invention.

100: organic electric element 110: substrate

120: first electrode (anode) 130: hole injection layer

140: hole transport layer 141: buffer layer

150 light emitting layer 151 light emitting auxiliary layer

160: electron transport layer 170: electron injection layer

180: second electrode (cathode)

Hereinafter, with reference to the embodiment of the present invention will be described in detail. In describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only to distinguish the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows:

The term "halo" or "halogen" as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

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 stated, and include straight or branched chain groups. It is not limited to this.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.

As used herein, the term "aryloxyl group" or "aryloxy group" means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto. In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

The prefix "aryl" or "ar" means 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 carbon number described herein.

Also, when prefixes are named consecutively, it means that the substituents are listed in the order described 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. Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

As used herein, the term “heterocyclic group” includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise stated.

"Heterocyclic groups" may also include rings comprising SO ₂ in place of the carbon forming the ring. For example, a "heterocyclic group" includes the following compounds.

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

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

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Unless otherwise stated, the term "carbonyl" used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is 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, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Group, germanium group, and C ₂ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

In addition, unless otherwise specified, the formulas used in the present invention apply in the same manner as the substituent definitions by the exponential definition of the following formula.

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

Hereinafter, a compound according to an aspect of the present invention and an organic electric element including the same will be described.

According to a specific example of this invention, the compound represented by following General formula (1) is provided.

Formula (1)

{In the above formula (1),

1) R ^1-13 is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); (wherein L 'is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; and a hetero ring group of C ₂ ~ C ₆₀ ; wherein R _a and R _b are independently of each other C ₆ ~ C ₆₀ Aryl group; fluorenyl group; C ₃ ~ C ₆₀ alicyclic ring and C ₆ ~ C ₆₀ Aromatic ring fused ring group; and O, N, S, Si and P containing at least one heteroatom Heterocyclic group of ₂ ~ C ₆₀ ; selected from the group consisting of

2) A represents an aryl group of C ₁₀ ,

3) L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P;

4) Ar ¹ , Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And -L'-N (R _a ) (R _b ); or Ar ^1,2 may combine with each other to form a ring,

5) n is an integer of 0-5.

Wherein the aryl group, heteroaryl group, fluorenyl group, arylene group, heterocyclic group and fused ring group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L _{'-N (R a) (R} b); C 1 ~ Import alkylthio of C _20; C ₁ ~ alkoxy group of C _20; C ₁ ~ alkyl group of C _20; C ₂ ~ C ₂₀ alkenyl group a; ₂ C ~ alkynyl of C _20; an aryl group of C ₆ - C ₂₀ substituted with heavy hydrogen;; C ₆ ~ C ₂₀ aryl group, a fluorenyl group; C ₂ - heterocyclic group of C _20; C of ₃ ~ C ₂₀ cycloalkyl An alkyl group; may be further substituted with one or more substituents selected from the group consisting of an arylalkyl group of C ₇ to C _{20 and} an arylalkenyl group of C ₈ to C ₂₀ , and these substituents may combine with each other to form a ring, wherein 'Ring' means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms, or a combination thereof Refers to a luer binary fused ring, a saturated or unsaturated ring.)}

In another specific example of the present invention, the compound of Formula (1) is represented by the following formula (2) to formula (4).

     Chemical Formula (2) Chemical Formula (3) Chemical Formula (4)

In Formulas (2) to (4), R ^{1 to 13} , L, Ar ^{1 , 2} and n are the same as R ^{1 to 13} , L, Ar ^{1, 2} and n defined in Formula (1).

The present invention also provides a compound characterized by the above formula (1) is represented by the following formula (5).

        Formula (5)

In the above formula (5),

1) R ^{1 ~ 13} , A, L, Ar ² , n is the same as R ^{1 ~ 13} , A, L, Ar ² , n defined in the formula (1),

2) R ', R "is hydrogen; C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₃ ~ fused ring group of a C ₆₀ aliphatic chain and C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ alkyl group; an alkenyl group of C ₂ ~ C _20; selected from the group consisting of, or combined with each other by the compound as a spy Can be formed,

3) o is an integer from 0 to 3,

4) R ^14-18 is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); selected from the group consisting of or adjacent to R ¹⁸ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ are bonded to each other aromatic Or heterocycle.

In another aspect, the present invention provides a compound characterized by the above formula (1) represented by the following formula (6).

           Formula (6)

In the above formula (6),

1) R ^{1 ~ 13} , A, L, Ar ² , n, m is the same as R ^{1 ~ 13} , A, L, Ar ² , n, m defined in the formula (1),

2) o is the same as o defined in the formula (5),

3) X is O or S,

4) R ^{18 ~ 22} is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); selected from the group consisting of or adjacent to R ¹⁸ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ²¹ and R ²² are bonded to each other and aromatic Or heterocycle.

As a more specific example, the present invention includes a compound represented by the following formula.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode formed on a substrate 110. An organic material layer including a compound represented by Chemical Formula 1 is provided between 180. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 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 layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.

Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions. Therefore, the selection of cores and the combination of sub-substituents bound thereto are also very significant. Importantly, long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

As described above, in order to solve the light emission problem in the hole transport layer in the organic electroluminescent device, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.

Therefore, in the present invention, by using the compound represented by the formula (1) as a hole transport layer material and / or light emitting auxiliary layer material, the energy level (level) and T1 value between each organic material layer, intrinsic properties (mobility, interfacial properties, etc.) ), Etc., can improve the life and efficiency of the organic electric device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.

Accordingly, the present invention includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer contains a compound included in Chemical Formula (1).

The present invention may further include an optical efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device.

In the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, the organic layer is a hole transport material containing the compound It provides an organic electric element, characterized in that.

As another specific example, the present invention provides an organic electric device, characterized in that the same or different compounds of the compound represented by the formula (1) are mixed and used in the organic material layer.

In another aspect, the present invention is a display device comprising the above-mentioned organic electric element; And a controller for driving the display device.

In another aspect, the organic electronic device provides an electronic device, characterized in that at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting device. In this case, the electronic device may be a current or future wired or 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 controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the synthesis examples of the compound represented by Chemical Formula 1 of the present invention and the production examples of the organic electric device of the present invention will be described in detail with reference to Examples, but are not limited to the following Examples of the present invention.

[ Synthesis Example  One]

Compound represented by the formula (1) according to the present invention (final product 1) is prepared by reacting Sub 1 with Sub 2, as shown in Scheme 1.

<Scheme 1>

Sub 1 Synthesis  example

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

If L is not a single bond

Sub 1- 1 Synthesis  example

1) Synthesis of Sub 1-1-1

Sub 1-1 (1) -1 (46.6.0 g, 200 mmol) and Sub 1-1 (2) -1 (52.9 g, 200 mmol) were dissolved in THF, and the temperature of the reaction was lowered to -78 ° C. n-BuLi (2.5 M inhexane) was slowly added dropwise and the reaction was stirred at room temperature for 4 hours. After the reaction was completed, the reaction product was placed in H ₂ O, quenched, the water in the reaction product was removed, filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated using column chromatography. Sub 1-1 (3) -1 67.9 g was obtained. (Yield: 81%) Subsequently, HCl and Acetic acid were added to Sub 1-1 (3) -1 (67.9 g, 162 mmol) g and stirred at 80 ° C. for 1 hour. When the reaction was terminated, after filtration under reduced pressure, the product produced by concentrating the organic solvent was separated using column chromatography to give 57.2g of Sub 1-1-1. (Yield 88%)

2) Synthesis of Sub 1-1-2

59.8g of Sub 1-1-2 was obtained by the same method as Sub 1-1-1. (Yield 92%)

3) Synthesis of Sub 1-1-3

59.8g of Sub 1-1-3 was obtained by the same method as Sub 1-1-1. (Yield 90%)

[Reference: Synthesis of Sub1-1 (2)]

Sub 1- 2 synthetic  example

1) Synthesis of Sub 1-2-1

Sub 1-1-1 (56.13 g, 140 mmol) in 980 mL of DMF, followed by Bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol After 24 hours of stirring), the obtained compound was separated through a silicagel column and recrystallization to obtain 48.3 g (70%) of borate compound Sub 1-2-1.

2) Synthesis of Sub 1-2-2

49.6g (72%) of the borate compound Sub 1-2-2 was obtained by the same experimental method as the Sub 1-2-1.

3) Synthesis of Sub 1-2-3

47.6 g (69%) of the borate compound Sub 1-2-3 was obtained through the same experimental method as the Sub 1-2-1.

Sub 1 synthesis example

1) Synthesis of Sub 1 (1)

Sub 1-2-1 (39.4g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8g, 84 mmol), Pd (PPh ₃ ) ₄ (2.8g, 2.4mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water were added, followed by stirring under reflux. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to give 28.8g (69%) of the product.

2) Synthesis of Sub 1 (2)

Sub 1-2-2 (39.4 g, 80 mmol), THF 360 mL, 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (33.5 g, 84 mmol), Pd (PPh ₃ ) ₄ ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water were added, and then 32.6 g (64%) of the product was obtained by the same experimental method as in Sub 1 (1).

3) Synthesis of Sub 1 (3)

Sub 1-2-3 (39.4 g, 80 mmol), THF 360 mL, 2-bromo-8-iododibenzo [b, d] thiophene (32.7g, 84 mmol), Pd (PPh ₃ ) ₄ (2.8g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water were added, and then 33.1 g (66%) of the product was obtained by the same experimental method as in Sub 1 (1).

An example of Sub 1 is as follows, but is not limited thereto.

compound	FD-MS	compound	FD-MS
Sub 1 (1)	m / z = 520.08 (C 35 H 21 Br = 521.45)	Sub 1 (2)	m / z = 636.15 (C 44 H 29 Br = 637.61)
Sub 1 (3)	m / z = 626.07 (C 41 H 23 BrS = 627.59)	Sub 1 (4)	m / z = 596.11 (C 41 H 25 Br = 597.54)
Sub 1 (5)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (6)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (7)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (8)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (9)	m / z = 520.08 (C 35 H 21 Br = 521.45)	Sub 1 (10)	m / z = 636.15 (C 44 H 29 Br = 637.61)
Sub 1 (11)	m / z = 626.07 (C 41 H 23 BrS = 627.59)	Sub 1 (12)	m / z = 596.11 (C 41 H 25 Br = 597.54)
Sub 1 (13)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (14)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (15)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (16)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (17)	m / z = 520.08 (C 35 H 21 Br = 521.45)	Sub 1 (18)	m / z = 636.15 (C 44 H 29 Br = 637.61)
Sub 1 (19)	m / z = 626.07 (C 41 H 23 BrS = 627.59)	Sub 1 (20)	m / z = 596.11 (C 41 H 25 Br = 597.54)
Sub 1 (21)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (22)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (23)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (24)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (25)	m / z = 476.13 (C 35 H 21 Cl = 476.99)	Sub 1 (26)	m / z = 477.13 (C 34 H 20 ClN = 477.98)
Sub 1 (27)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (28)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (29)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (30)	m / z = 400.10 (C 29 H 17 Cl = 400.90)
Sub 1 (31)	m / z = 400.10 (C 29 H 17 Cl = 400.90)	Sub 1 (32)	m / z = 400.10 (C 29 H 17 Cl = 400.90)

Sub 2 Synthesis Example

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

<Scheme 3>

Synthesis Example of Sub 2-28

4-bromo-1,1'-biphenyl (5.6 g, 24 mmol) was dissolved in toluene, followed by [1,1'-biphenyl] -4-amine (3.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g). , 0.6 mmol), P (t-Bu) ₃ (0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, and the mixture was refluxed at 100 ° C. for 24 hours. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain 6.2g (yield: 80%) of the final compound.

An example of Sub 2 is as follows, but is not limited thereto.

compound	FD-MS	compound	FD-MS
Sub 2-1	m / z = 169.09 (C 12 H 11 N = 169.22)	Sub 2-2	m / z = 219.10 (C 16 H 13 N = 219.28)
Sub 2-3	m / z = 219.10 (C 16 H 13 N = 219.28)	Sub 2-4	m / z = 245.12 (C 18 H 15 N = 245.32)
Sub 2-5	m / z = 170.08 (C 11 H 10 N 2 = 170.21)	Sub 2-6	m / z = 199.10 (C 10 H 13 NO = 199.25)
Sub 2-7	m / z = 225.15 (C 16 H 19 N = 225.33)	Sub 2-8	m / z = 285.15 (C 21 H 19 N = 285.38)
Sub 2-9	m / z = 409.18 (C 31 H 23 N = 409.52)	Sub 2-10	m / z = 407.17 (C 31 H 21 N = 407.51)
Sub 2-11	m / z = 269.12 (C 20 H 15 N = 269.34)	Sub 2-12	m / z = 269.12 (C 20 H 15 N = 269.34)
Sub 2-13	m / z = 295.14 (C 22 H 17 N = 295.38)	Sub 2-14	m / z = 220.10 (C 15 H 12 N 2 = 220.27)
Sub 2-15	m / z = 249.12 (C 17 H 12 NO = 249.31)	Sub 2-16	m / z = 275.17 (C 20 H 21 N = 275.39)
Sub 2-17	m / z = 335.17 (C 25 H 21 N = 335.44)	Sub 2-18	m / z = 459.20 (C 35 H 25 N = 459.58)
Sub 2-19	m / z = 457.18 (C 35 H 23 N = 457.56)	Sub 2-20	m / z = 269.12 (C 20 H 15 N = 269.34)
Sub 2-21	m / z = 295.14 (C 22 H 17 N = 295.38)	Sub 2-22	m / z = 220.10 (C 15 H 2 N 2 = 220.27)
Sub 2-23	m / z = 249.12 (C 17 H 15 NO = 249.31)	Sub 2-24	m / z = 275.17 (C 20 H 21 N = 275.39)
Sub 2-25	m / z = 335.17 (C 25 H 21 N = 335.44)	Sub 2-26	m / z = 459.20 (C 35 H 25 N = 459.58)
Sub 2-27	m / z = 457.18 (C 35 H 23 N = 457.56)	Sub 2-28	m / z = 321.15 (C 24 H 19 N = 321.41)
Sub 2-29	m / z = 246.12 (C 17 H 14 N 2 = 246.31)	Sub 2-30	m / z = 275.13 (C 19 H 17 NO = 275.34)
Sub 2-31	m / z = 301.18 (C 22 H 23 N = 301.42)	Sub 2-32	m / z = 361.18 (C 27 H 23 N = 361.48)
Sub 2-33	m / z = 485.21 (C 37 H 27 N = 485.62)	Sub 2-34	m / z = 483.20 (C 37 H 25 N = 483.60)
Sub 2-35	m / z = 171.08 (C 10 H 09 N 3 = 171.20)	Sub 2-36	m / z = 200.09 (C 12 H 12 N 2 O = 200.24)
Sub 2-37	m / z = 226.15 (C 15 H 18 N 2 = 226.32)	Sub 2-38	m / z = 286.15 (C 20 H 18 N 2 = 286.37)
Sub 2-39	m / z = 410.18 (C 30 H 22 N 2 = 410.51)	Sub 2-40	m / z = 408.16 (C 30 H 20 N 2 = 408.49)
Sub 2-41	m / z = 229.11 (C 14 H 15 NO 2 = 229.27)	Sub 2-42	m / z = 255.16 (C 17 H 21 NO = 255.35)
Sub 2-43	m / z = 315.16 (C 22 H 21 NO = 315.41)	Sub 2-44	m / z = 439.19 (C 32 H 25 NO = 439.55)
Sub 2-45	m / z = 437.18 (C 32 H 23 NO = 437.53)	Sub 2-46	m / z = 281.21 (C 20 H 27 N = 281.44)
Sub 2-47	m / z = 341.21 (C 25 H 27 N = 341.49)	Sub 2-48	m / z = 465.25 (C 35 H 31 N = 465.63)
Sub 2-49	m / z = 463.23 (C 35 H 29 N = 463.61)	Sub 2-50	m / z = 401.21 (C 30 H 27 N = 401.54)
Sub 2-51	m / z = 525.25 (C 40 H 31 N = 525.68)	Sub 2-52	m / z = 523.23 (C 40 H 29 N = 523.66)
Sub 2-53	m / z = 351.11 (C 24 H 17 NS = 351.46)	Sub 2-54	m / z = 401.12 (C 28 H 19 NS = 401.52)
Sub 2-55	m / z = 357.11 (C 26 H 17 NS = 375.48)	Sub 2-56	m / z = 427.14 (C 30 H 21 NS = 427.56)
Sub 2-57	m / z = 335.13 (C 24 H 17 NO = 335.40)	Sub 2-58	m / z = 335.13 (C 24 H 17 NO = 335.40)
Sub 2-59	m / z = 349.11 (C 24 H 15 NO 2 = 349.38)	Sub 2-60	m / z = 381.06 (C 24 H 15 NS 2 = 381.51)
Sub 2-61	m / z = 365.09 (C 24 H 15 NOS = 365.45)	Sub 2-62	m / z = 533.13 (C 36 H 23 NS 2 = 533.70)
Sub 2-63	m / z = 501.17 (C 36 H 23 NO 2 = 501.57)	Sub 2-64	m / z = 517.15 (C 36 H 23 NOS = 349.38)

Final Products Synthesis Example

Synthesis Example of 1-12

Sub 1 (6) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-32 (6.7 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, and the mixture was stirred under reflux for 24 hours at 100 ° C. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain 11.7 g (yield: 70%) of the final compound.

Synthesis Example of 1-13

Sub 1 (33) (14.3 g, 24 mmol) was dissolved in toluene, then Sub 2-5 (3.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and 9.9g (yield: 60%) was obtained by the same experimental method as in 1-12. .

Synthesis Example of 1-15

Sub 1 (34) (15.1 g, ₂₄ mmol) was dissolved in toluene, then Sub 2-3 (4.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, respectively, and 11.2g (yield: 61%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 1-22

Sub 1 (6) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-32 (7.2 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, respectively, and then 11.8 g (yield: 68%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 1-30

Sub 1 (1) (12.5g, 24mmol) was dissolved in toluene, then Sub 2-12 (5.4g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, respectively, and then 12.1g (yield: 71%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 1-32

Sub 35 (28) (15.3 g, 24 mmol) was dissolved in toluene, then Sub 2-28 (6.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 12.4g (yield: 59%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 2-4

Sub 1 (15) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-4 (4.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 10.4g (yield: 71%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 2-8

Sub 1 (16) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-10 (8.2 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol), and toluene (300 mL) were added, and the final compound was obtained in the same manner as in 1-12, yielding 12.4: 67.

Synthesis Example of 2-15

Sub 1 (36) (15.1 g, ₂₄ mmol) was dissolved in toluene, then Sub 2-3 (4.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 11.4g (yield: 62%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 2-16

Sub 1 (37) (15.3 g, 24 mmol) was dissolved in toluene, then Sub 2-65 (4.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, respectively, and 11.7g (yield: 61%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 2-30

Sub 1 (38) (12.5g, 24mmol) was dissolved in toluene, then Sub 2-12 (5.4g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, respectively, and 11.9g (yield: 70%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 2-37

Sub 1 (16) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-67 (7.3 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 11.4g (yield: 65%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-5

Sub 1 (23) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-66 (4.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 10.4g (yield: 71%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-12

Sub 1 (22) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-58 (6.7 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, respectively, and then 10.9g (yield: 65%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-14

Sub 1 (39) (12.5g, 24mmol) was dissolved in toluene, then Sub 2-2 (4.4g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 10.8g (yield: 68%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-29

Sub 1 (40) (14.3 g, 24 mmol) was dissolved in toluene, then Sub 2-14 (4.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, respectively, and then 11.0 g (yield: 62%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-31

Sub 1 (41) (15.11 g, ₂₄ mmol) was dissolved in toluene, then Sub 2-67 (5.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (300 mL) were added, and then 12.9g (yield: 64%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-32

Sub 1 (42) (15.3 g, 24 mmol) was dissolved in toluene, then Sub 2-28 (6.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol), toluene (300 mL) were added, and 14.3g (yield: 68%) of the final compound was obtained by the same experimental method as in 1-12. .

Synthesis Example of 3-40

Sub 1 (23) (9.6 g, 24 mmol) was dissolved in toluene, then Sub 2-68 (7.3 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ ( 0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol), and toluene (300 mL) were added, respectively, and then 11.8 g (yield: 70%) of the final compound was obtained by the same experimental method as in 1-12. .

compound	FD-MS	compound	FD-MS
1-1	m / z = 533.21 (C 41 H 27 N = 533.66)	1-2	m / z = 583.23 (C 45 H 29 N = 583.72)
1-3	m / z = 583.23 (C 45 H 29 N = 583.72)	1-4	m / z = 609.25 (C 47 H 31 N = 609.76)
1-5	m / z = 609.25 (C 47 H 31 N = 609.76)	1-6	m / z = 649.28 (C 50 H 35 N = 649.82)
1-7	m / z = 773.31 (C 60 H 39 N = 773.96)	1-8	m / z = 771.29 (C 60 H 37 N = 771.94)
1-9	m / z = 821.31 (C 64 H 39 N = 822.00)	1-10	m / z = 639.20 (C 47 H 29 NS = 639.80)
1-11	m / z = 698.27 (C 53 H 34 N = 698.85)	1-12	m / z = 699.26 (C 53 H 33 NO = 699.84)
1-13	m / z = 686.27 (C 52 H 34 N 2 = 686.84)	1-14	m / z = 659.26 (C 51 H 33 N = 659.81)
1-15	m / z = 765.25 (C 57 H 35 NS = 765.96)	1-16	m / z = 801.34 (C 62 H 43 N = 802.01)
1-17	m / z = 609.25 (C 47 H 31 N = 609.76)	1-18	m / z = 659.26 (C 51 H 33 N = 659.81)
1-19	m / z = 659.26 (C 51 H 33 N = 659.81)	1-20	m / z = 685.28 (C 53 H 35 N = 685.85)
1-21	m / z = 685.28 (C 53 H 35 N = 685.85)	1-22	m / z = 725.31 (C 56 H 39 N = 725.92)
1-23	m / z = 849.34 (C 66 H 43 N = 850.05)	1-24	m / z = 847.32 (C 66 H 41 N = 848.04)
1-25	m / z = 897.34 (C 70 H 43 N = 898.10)	1-26	m / z = 715.23 (C 53 H 33 NS = 715.90)
1-27	m / z = 774.30 (C 59 H 38 N 2 = 774.95)	1-28	m / z = 775.29 (C 59 H 37 NO = 775.93)
1-29	m / z = 736.29 (C 56 H 36 N 2 = 736.90)	1-30	m / z = 709.28 (C 55 H 35 N = 709.87)
1-31	m / z = 841.28 (C 63 H 39 NS = 842.06)	1-32	m / z = 877.37 (C 68 H 47 N = 878.11)
1-33	m / z = 761.31 (C 59 H 39 N = 761.95)	1-34	m / z = 761.31 (C 59 H 39 N = 761.95)
1-35	m / z = 762.30 (C 58 H 38 N 2 = 762.94)	1-36	m / z = 761.31 (C 59 H 39 N = 761.95)
1-37	m / z = 730.34 (C 56 H 34 D 5 N = 730.95)	1-39	m / z = 739.32 (C 57 H 41 N = 739.94)
1-39	m / z = 690.31 (C 53 H 30 D 5 N = 690.88)	1-40	m / z = 699.29 (C 54 H 37 N = 699.88)
2-1	m / z = 533.21 (C 41 H 27 N = 533.66)	2-2	m / z = 583.23 (C 45 H 29 N = 583.72)
2-3	m / z = 583.23 (C 45 H 29 N = 583.72)	2-4	m / z = 609.25 (C 47 H 31 N = 609.76)
2-5	m / z = 609.25 (C 47 H 31 N = 609.76)	2-6	m / z = 649.28 (C 50 H 35 N = 649.82)
2-7	m / z = 773.31 (C 60 H 39 N = 773.96)	2-8	m / z = 771.29 (C 60 H 37 N = 771.94)
2-9	m / z = 821.31 (C 64 H 39 N = 822.00)	2-10	m / z = 639.20 (C 47 H 29 NS = 639.80)
2-11	m / z = 698.27 (C 53 H 34 N = 698.85)	2-12	m / z = 699.26 (C 53 H 33 NO = 699.84)
2-13	m / z = 686.27 (C 52 H 34 N 2 = 686.84)	2-14	m / z = 659.26 (C 51 H 33 N = 659.81)
2-15	m / z = 765.25 (C 57 H 35 NS = 765.96)	2-16	m / z = 801.34 (C 62 H 43 N = 802.01)
2-17	m / z = 609.25 (C 47 H 31 N = 609.76)	2-18	m / z = 659.26 (C 51 H 33 N = 659.81)
2-19	m / z = 659.26 (C 51 H 33 N = 659.81)	2-20	m / z = 685.28 (C 53 H 35 N = 685.85)
2-21	m / z = 685.28 (C 53 H 35 N = 685.85)	2-22	m / z = 725.31 (C 56 H 39 N = 725.92)
2-23	m / z = 849.34 (C 66 H 43 N = 850.05)	2-24	m / z = 847.32 (C 66 H 41 N = 848.04)
2-25	m / z = 897.34 (C 70 H 43 N = 898.10)	2-26	m / z = 715.23 (C 53 H 33 NS = 715.90)
2-27	m / z = 774.30 (C 59 H 38 N 2 = 774.95)	2-28	m / z = 775.29 (C 59 H 37 NO = 775.93)
2-29	m / z = 736.29 (C 56 H 36 N 2 = 736.90)	2-30	m / z = 709.28 (C 55 H 35 N = 709.87)
2-31	m / z = 841.28 (C 63 H 39 NS = 842.06)	2-32	m / z = 877.37 (C 68 H 47 N = 878.11)
2-33	m / z = 761.31 (C 59 H 39 N = 761.95)	2-34	m / z = 761.31 (C 59 H 39 N = 761.95)
2-35	m / z = 762.30 (C 58 H 38 N 2 = 762.94)	2-36	m / z = 761.31 (C 59 H 39 N = 761.95)
2-37	m / z = 730.34 (C 56 H 34 D 5 N = 730.95)	2-39	m / z = 739.32 (C 57 H 41 N = 739.94)
2-39	m / z = 690.31 (C 53 H 30 D 5 N = 690.88)	2-40	m / z = 699.29 (C 54 H 37 N = 699.88)
3-1	m / z = 533.21 (C 41 H 27 N = 533.66)	3-2	m / z = 583.23 (C 45 H 29 N = 583.72)
3-3	m / z = 583.23 (C 45 H 29 N = 583.72)	3-4	m / z = 609.25 (C 47 H 31 N = 609.76)
3-5	m / z = 609.25 (C 47 H 31 N = 609.76)	3-6	m / z = 649.28 (C 50 H 35 N = 649.82)
3-7	m / z = 773.31 (C 60 H 39 N = 773.96)	3-8	m / z = 771.29 (C 60 H 37 N = 771.94)
3-9	m / z = 821.31 (C 64 H 39 N = 822.00)	3-10	m / z = 639.20 (C 47 H 29 NS = 639.80)
3-11	m / z = 698.27 (C 53 H 34 N = 698.85)	3-12	m / z = 699.26 (C 53 H 33 NO = 699.84)
3-13	m / z = 686.27 (C 52 H 34 N 2 = 686.84)	3-14	m / z = 659.26 (C 51 H 33 N = 659.81)
3-15	m / z = 765.25 (C 57 H 35 NS = 765.96)	3-16	m / z = 801.34 (C 62 H 43 N = 802.01)
3-17	m / z = 609.25 (C 47 H 31 N = 609.76)	3-18	m / z = 659.26 (C 51 H 33 N = 659.81)
3-19	m / z = 659.26 (C 51 H 33 N = 659.81)	3-20	m / z = 685.28 (C 53 H 35 N = 685.85)
3-21	m / z = 685.28 (C 53 H 35 N = 685.85)	3-22	m / z = 725.31 (C 56 H 39 N = 725.92)
3-23	m / z = 849.34 (C 66 H 43 N = 850.05)	3-24	m / z = 847.32 (C 66 H 41 N = 848.04)
3-25	m / z = 897.34 (C 70 H 43 N = 898.10)	3-26	m / z = 715.23 (C 53 H 33 NS = 715.90)
3-29	m / z = 774.30 (C 59 H 38 N 2 = 774.95)	3-30	m / z = 775.29 (C 59 H 37 NO = 775.93)
3-31	m / z = 736.29 (C 56 H 36 N 2 = 736.90)	3-32	m / z = 709.28 (C 55 H 35 N = 709.87)
3-33	m / z = 841.28 (C 63 H 39 NS = 842.06)	3-34	m / z = 877.37 (C 68 H 47 N = 878.11)
3-35	m / z = 761.31 (C 59 H 39 N = 761.95)	3-36	m / z = 761.31 (C 59 H 39 N = 761.95)
3-37	m / z = 762.30 (C 58 H 38 N 2 = 762.94)	3-39	m / z = 761.31 (C 59 H 39 N = 761.95)
3-39	m / z = 730.34 (C 56 H 34 D 5 N = 730.95)	3-40	m / z = 739.32 (C 57 H 41 N = 739.94)

Manufacturing Evaluation of Organic Electrical Device

Example 1) blue  Fabrication and Test of Organic Light-Emitting Device Hole transport layer )

First, on the ITO layer (anode) formed on the glass substrate, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm. Subsequently, the compound 1-1 of the present invention was vacuum-deposited to a thickness of 60 nm using a hole transport compound on the film to form a hole transport layer. A light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer by doping 9,10-di (naphthalen-2-yl) anthracene as a light emitting layer host on the hole transport layer and BD-052X (Idemitsukosan) as a dopant at 96: 4 weight. As a hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a 40 nm thick film. Subsequently, 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 to prepare an organic light emitting device.

The electroluminescent (EL) characteristics were measured by the PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent light emitting diodes prepared in Example and Comparative Example. The T95 life was measured using a life measurement instrument manufactured by McScience. The following table shows the results of device fabrication and evaluation.

Comparative Compound A Comparative Compound B Comparative Compound C Comparative Compound D

	compound	Voltage	Current density	Brightness (cd / m2)	Efficiency	LifetimeT (95)	CIE (x, y)
Comparative Example (1)	Compound (A)	5.8	13.5	500.0	3.7	61.8	(0.15, 0.13)
Comparative Example (2)	Compound (B)	5.3	10.6	500.0	4.7	92.7	(0.14, 0.14)
Comparative Example (3)	Compound (C)	5.2	11.6	500.0	4.3	94.1	(0.15, 0.14)
Comparative Example (3)	Compound (C)	4.8	10.5	500.0	4.8	94.3	(0.15, 0.14)
Example (1)	Compound (1-1)	4.9	9.8	500.0	5.1	109.0	(0.14, 0.14)
Example (2)	Compound (1-2)	4.9	9.7	500.0	5.2	103.4	(0.15, 0.13)
Example (3)	Compound (1-3)	4.8	9.9	500.0	5.0	101.0	(0.15, 0.16)
Example (4)	Compound (1-4)	4.9	9.6	500.0	5.2	109.6	(0.15, 0.14)
Example (5)	Compound (1-34)	4.9	9.5	500.0	5.3	108.2	(0.15, 0.13)
Example (6)	Compound (1-35)	5.0	9.4	500.0	5.3	116.7	(0.14, 0.14)
Example (7)	Compound (1-40)	4.9	9.8	500.0	5.1	119.1	(0.15, 0.14)
Example (1)	Compound (1-1)	4.8	9.9	500.0	5.0	114.7	(0.15, 0.13)
Example (2)	Compound (1-2)	4.9	9.5	500.0	5.3	114.4	(0.15, 0.14)
Example (3)	Compound (1-3)	4.9	9.8	500.0	5.1	108.7	(0.15, 0.13)
Example (4)	Compound (1-4)	4.9	9.9	500.0	5.0	115.2	(0.14, 0.14)
Example (5)	Compound (1-5)	5.0	9.7	500.0	5.2	108.9	(0.14, 0.14)
Example (6)	Compound (1-6)	4.9	9.5	500.0	5.3	103.6	(0.14, 0.14)
Example (7)	Compound (1-7)	4.8	9.6	500.0	5.2	108.0	(0.15, 0.13)
Example (8)	Compound (1-8)	4.8	9.6	500.0	5.2	113.1	(0.15, 0.14)
Example (9)	Compound (1-9)	4.9	9.9	500.0	5.1	104.6	(0.15, 0.14)
Example (10)	Compound (1-10)	4.9	9.4	500.0	5.3	105.0	(0.15, 0.13)
Example (11)	Compound (1-11)	4.9	9.5	500.0	5.2	119.6	(0.14, 0.14)
Example (12)	Compound (1-12)	5.0	9.9	500.0	5.1	112.6	(0.15, 0.14)
Example (13)	Compound (1-13)	5.0	9.6	500.0	5.2	109.6	(0.15, 0.14)
Example (14)	Compound (1-14)	5.0	9.6	500.0	5.2	107.2	(0.14, 0.14)
Example (15)	Compound (1-15)	5.0	9.8	500.0	5.1	101.9	(0.15, 0.13)
Example (16)	Compound (1-16)	4.8	9.6	500.0	5.2	109.1	(0.15, 0.16)
Example (17)	Compound (1-17)	5.0	9.9	500.0	5.1	105.2	(0.15, 0.14)
Example (18)	Compound (1-18)	5.0	9.8	500.0	5.1	104.1	(0.15, 0.13)
Example (19)	Compound (1-19)	5.0	9.8	500.0	5.1	111.8	(0.14, 0.14)
Example (20)	Compound (1-20)	4.9	9.7	500.0	5.2	104.2	(0.15, 0.14)
Example (21)	Compound (1-21)	4.9	9.8	500.0	5.1	107.8	(0.15, 0.13)
Example (22)	Compound (1-22)	4.9	9.5	500.0	5.3	106.6	(0.14, 0.14)
Example (23)	Compound (1-23)	5.0	9.9	500.0	5.0	102.5	(0.14, 0.14)
Example (24)	Compound (1-24)	4.9	9.6	500.0	5.2	105.9	(0.15, 0.13)
Example (25)	Compound (1-25)	4.9	9.5	500.0	5.3	119.8	(0.15, 0.14)
Example (26)	Compound (1-26)	4.8	9.7	500.0	5.2	118.6	(0.14, 0.14)
Example (27)	Compound (1-27)	5.0	10.0	500.0	5.0	105.9	(0.15, 0.14)
Example (28)	Compound (1-28)	4.9	10.0	500.0	5.0	113.4	(0.15, 0.14)
Example (29)	Compound (1-29)	5.0	9.4	500.0	5.3	116.9	(0.15, 0.13)
Example (30)	Compound (1-30)	4.8	9.5	500.0	5.3	107.4	(0.14, 0.14)
Example (31)	Compound (1-31)	4.8	9.8	500.0	5.1	103.4	(0.14, 0.14)
Example (32)	Compound (1-32)	4.8	9.7	500.0	5.1	112.4	(0.14, 0.14)
Example (33)	Compound (1-33)	4.9	9.9	500.0	5.1	111.8	(0.15, 0.13)
Example (34)	Compound (1-34)	5.0	10.0	500.0	5.0	109.7	(0.15, 0.14)
Example (35)	Compound (1-35)	4.9	9.5	500.0	5.2	108.9	(0.15, 0.14)
Example (36)	Compound (1-36)	5.0	9.8	500.0	5.1	105.9	(0.15, 0.13)
Example (37)	Compound (1-37)	4.8	9.7	500.0	5.2	104.8	(0.15, 0.14)
Example (38)	Compound (1-38)	4.9	9.4	500.0	5.3	104.7	(0.15, 0.13)
Example (39)	Compound (1-39)	4.8	9.7	500.0	5.1	113.5	(0.14, 0.14)
Example (40)	Compound (1-40)	4.8	9.5	500.0	5.2	106.9	(0.14, 0.14)
Example (41)	Compound (2-1)	4.8	9.4	500.0	5.3	113.2	(0.15, 0.14)
Example (42)	Compound (2-2)	4.9	9.6	500.0	5.2	119.5	(0.15, 0.14)
Example (43)	Compound (2-3)	5.0	9.8	500.0	5.1	103.4	(0.14, 0.14)
Example (44)	Compound (2-4)	4.9	9.8	500.0	5.1	105.1	(0.15, 0.14)
Example (45)	Compound (2-5)	4.9	9.4	500.0	5.3	102.9	(0.14, 0.14)
Example (46)	Compound (2-6)	4.9	9.9	500.0	5.0	111.7	(0.15, 0.15)
Example (47)	Compound (2-7)	4.8	9.5	500.0	5.3	101.7	(0.15, 0.13)
Example (48)	Compound (2-8)	4.9	9.6	500.0	5.2	104.9	(0.15, 0.14)
Example (49)	Compound (2-9)	4.8	9.9	500.0	5.0	100.2	(0.15, 0.16)
Example (50)	Compound (2-10)	4.9	9.6	500.0	5.2	108.6	(0.15, 0.14)
Example (51)	Compound (2-11)	5.0	9.8	500.0	5.1	110.2	(0.14, 0.14)
Example (52)	Compound (2-12)	4.8	9.8	500.0	5.1	100.0	(0.14, 0.14)
Example (53)	Compound (2-13)	5.0	9.7	500.0	5.2	104.1	(0.15, 0.13)
Example (54)	Compound (2-14)	5.0	10.0	500.0	5.0	102.3	(0.15, 0.15)
Example (55)	Compound (2-15)	4.8	9.9	500.0	5.1	106.4	(0.15, 0.16)
Example (56)	Compound (2-16)	5.0	9.8	500.0	5.1	105.0	(0.15, 0.14)
Example (57)	Compound (2-17)	4.8	9.6	500.0	5.2	105.1	(0.15, 0.14)
Example (58)	Compound (2-18)	5.0	9.8	500.0	5.1	100.8	(0.15, 0.15)
Example (59)	Compound (2-19)	4.9	9.6	500.0	5.2	112.5	(0.15, 0.14)
Example (60)	Compound (2-20)	5.0	10.0	500.0	5.0	110.4	(0.15, 0.14)
Example (61)	Compound (2-21)	4.9	10.0	500.0	5.0	102.8	(0.14, 0.14)
Example (62)	Compound (2-22)	4.9	9.9	500.0	5.1	102.7	(0.15, 0.14)
Example (63)	Compound (2-23)	4.9	9.6	500.0	5.2	116.7	(0.15, 0.13)
Example (64)	Compound (2-24)	4.9	9.6	500.0	5.2	113.2	(0.15, 0.14)
Example (65)	Compound (2-25)	4.9	9.7	500.0	5.2	111.8	(0.15, 0.14)
Example (66)	Compound (2-26)	4.9	9.6	500.0	5.2	106.9	(0.15, 0.14)
Example (67)	Compound (2-27)	4.9	9.8	500.0	5.1	116.8	(0.15, 0.13)
Example (68)	Compound (2-28)	5.0	9.7	500.0	5.2	101.6	(0.15, 0.13)
Example (69)	Compound (2-29)	4.9	9.5	500.0	5.3	110.3	(0.15, 0.14)
Example (70)	Compound (2-30)	5.0	9.8	500.0	5.1	106.0	(0.15, 0.15)
Example (71)	Compound (2-31)	4.9	9.7	500.0	5.2	110.5	(0.15, 0.15)
Example (72)	Compound (2-32)	4.9	9.6	500.0	5.2	105.8	(0.15, 0.14)
Example (73)	Compound (2-33)	4.9	9.5	500.0	5.3	103.1	(0.15, 0.14)
Example (74)	Compound (2-34)	4.9	9.7	500.0	5.1	117.4	(0.15, 0.16)
Example (75)	Compound (2-35)	4.9	9.9	500.0	5.0	105.6	(0.14, 0.14)
Example (76)	Compound (2-36)	4.9	9.6	500.0	5.2	103.6	(0.15, 0.13)
Example (77)	Compound (2-37)	4.9	9.5	500.0	5.3	109.8	(0.15, 0.14)
Example (78)	Compound (2-38)	4.9	9.9	500.0	5.1	101.7	(0.15, 0.13)
Example (79)	Compound (2-39)	5.0	9.5	500.0	5.3	115.6	(0.14, 0.14)
Example (80)	Compound (2-40)	5.0	9.9	500.0	5.1	118.6	(0.14, 0.14)
Example (81)	Compound (3-1)	4.9	9.5	500.0	5.2	109.9	(0.15, 0.13)
Example (82)	Compound (3-2)	4.9	9.7	500.0	5.2	108.5	(0.15, 0.14)
Example (83)	Compound (3-3)	4.8	10.0	500.0	5.0	111.7	(0.15, 0.14)
Example (84)	Compound (3-4)	4.9	9.8	500.0	5.1	108.9	(0.15, 0.15)
Example (85)	Compound (3-5)	4.8	9.6	500.0	5.2	112.0	(0.15, 0.13)
Example (86)	Compound (3-6)	5.0	9.9	500.0	5.1	103.4	(0.15, 0.14)
Example (87)	Compound (3-7)	4.8	9.6	500.0	5.2	100.1	(0.15, 0.13)
Example (88)	Compound (3-8)	4.9	9.8	500.0	5.1	107.5	(0.15, 0.14)
Example (89)	Compound (3-9)	5.0	10.0	500.0	5.0	118.7	(0.15, 0.14)
Example (90)	Compound (3-10)	5.0	9.8	500.0	5.1	118.9	(0.15, 0.14)
Example (91)	Compound (3-11)	5.0	9.9	500.0	5.0	100.2	(0.15, 0.14)
Example (92)	Compound (3-12)	4.9	9.8	500.0	5.1	110.5	(0.14, 0.14)
Example (93)	Compound (3-13)	4.9	9.6	500.0	5.2	115.2	(0.14, 0.14)
Example (94)	Compound (3-14)	4.9	9.7	500.0	5.2	103.7	(0.15, 0.14)
Example (95)	Compound (3-15)	4.8	9.6	500.0	5.2	111.6	(0.15, 0.13)
Example (96)	Compound (3-16)	4.9	9.6	500.0	5.2	112.8	(0.15, 0.15)
Example (97)	Compound (3-17)	4.9	9.5	500.0	5.3	102.8	(0.15, 0.13)
Example (98)	Compound (3-18)	4.9	9.6	500.0	5.2	106.2	(0.15, 0.14)
Example (99)	Compound (3-19)	4.9	10.0	500.0	5.0	110.2	(0.15, 0.14)
Example (100)	Compound (3-20)	4.8	9.7	500.0	5.1	111.2	(0.14, 0.14)
Example (101)	Compound (3-21)	4.8	9.8	500.0	5.1	116.9	(0.15, 0.13)
Example (102)	Compound (3-22)	4.8	9.5	500.0	5.3	117.3	(0.15, 0.14)
Example (103)	Compound (3-23)	4.9	9.5	500.0	5.2	114.8	(0.15, 0.14)
Example (104)	Compound (3-24)	4.8	9.8	500.0	5.1	112.6	(0.14, 0.14)
Example 105	Compound (3-25)	4.9	9.8	500.0	5.1	110.6	(0.15, 0.16)
Example 106	Compound (3-26)	4.8	9.9	500.0	5.1	108.2	(0.15, 0.13)
Example 107	Compound (3-27)	4.9	10.0	500.0	5.0	100.5	(0.15, 0.14)
Example 108	Compound (3-28)	4.9	9.8	500.0	5.1	104.7	(0.15, 0.14)
Example 109	Compound (3-29)	4.9	9.7	500.0	5.1	105.1	(0.15, 0.14)
Example (110)	Compound (3-30)	5.0	9.9	500.0	5.0	112.6	(0.15, 0.16)
Example (111)	Compound (3-31)	5.0	9.4	500.0	5.3	102.8	(0.14, 0.14)
Example (112)	Compound (3-32)	4.9	9.5	500.0	5.3	118.7	(0.15, 0.14)
Example (113)	Compound (3-33)	4.8	9.9	500.0	5.1	109.6	(0.14, 0.14)
Example 114	Compound (3-34)	5.0	9.9	500.0	5.0	105.1	(0.15, 0.15)
Example 115	Compound (3-35)	4.9	9.6	500.0	5.2	114.8	(0.15, 0.13)
Example 116	Compound (3-36)	4.9	10.0	500.0	5.0	111.6	(0.15, 0.14)
Example 117	Compound (3-37)	4.8	9.7	500.0	5.1	100.3	(0.15, 0.14)
Example 118	Compound (3-38)	4.8	9.8	500.0	5.1	116.3	(0.15, 0.13)
Example (119)	Compound (3-39)	4.9	9.8	500.0	5.1	111.6	(0.14, 0.14)
Example 120	Compound (3-40)	4.8	9.5	500.0	5.3	113.2	(0.14, 0.14)

As can be seen from the results of Table 4, it was confirmed that the driving voltage and life were remarkably improved when the organic electroluminescent device material of the present invention was used as the hole transport layer.

In other words, Comparative Examples 2 to 4, which use Comparative Compounds B to D where spirofluorene is substituted for tertiary amines as the hole transport layer, are excellent in terms of driving voltage, efficiency, and lifetime, as compared to Comparative Example 1, which uses NPB as the hole transport layer. The results were shown, and Examples 1 to 120 using the compound of the present invention substituted with a spirofluorene fused to a tertiary amine than Comparative Examples 2 to 4 showed an improved effect on driving voltage, efficiency, and lifetime. .

As a result of evaluating the hole injection and mobility ability of the compound, the compound of the present invention, in which the fused spiro fluorene is substituted, has much better hole injection capability and faster mobility than the comparable compounds B to D in which spirofluorene is substituted. I could see that. Therefore, as hole injection and mobility are improved, deterioration at the interface between ITO and HTL is reduced, and the life of the device is improved. As more holes are moved to the light emitting layer, the charge balance in the light emitting layer of holes and electrons is increased, thereby increasing the hole transport layer interface. In addition, it is determined that luminescence is well performed in the light emitting layer, thereby maximizing driving voltage, efficiency, and lifespan. This suggests that the physical properties of the compound and the results of the device are significantly changed as the spirofluorene is fused.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe 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 the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

Claims (12)

1. Compound represented by the following formula (1)

   Formula (1)

   

   {In the above formula (1),

   1) R ^1-13 is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); (wherein L 'is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; and a hetero ring group of C ₂ ~ C ₆₀ ; wherein R _a and R _b are independently of each other C ₆ ~ C ₆₀ Aryl group; fluorenyl group; C ₃ ~ C ₆₀ alicyclic ring and C ₆ ~ C ₆₀ Aromatic ring fused ring group; and O, N, S, Si and P containing at least one heteroatom Heterocyclic group of ₂ ~ C ₆₀ ; selected from the group consisting of

   2) A represents an aryl group of C ₁₀ ,

   3) L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P;

   4) Ar ¹ , Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And -L'-N (R _a ) (R _b ); or Ar ^1,2 may combine with each other to form a ring,

   5) n is an integer of 0-5.

   Wherein the aryl group, heteroaryl group, fluorenyl group, arylene group, heterocyclic group and fused ring group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L _{'-N (R a) (R} b); C 1 ~ Import alkylthio of C _20; C ₁ ~ alkoxy group of C _20; C ₁ ~ alkyl group of C _20; C ₂ ~ C ₂₀ alkenyl group a; ₂ C ~ alkynyl of C _20; an aryl group of C ₆ - C ₂₀ substituted with heavy hydrogen;; C ₆ ~ C ₂₀ aryl group, a fluorenyl group; C ₂ - heterocyclic group of C _20; C of ₃ ~ C ₂₀ cycloalkyl An alkyl group; may be further substituted with one or more substituents selected from the group consisting of an arylalkyl group of C ₇ to C _{20 and} an arylalkenyl group of C ₈ to C ₂₀ , and these substituents may combine with each other to form a ring, wherein 'Ring' means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms, or a combination thereof Refers to a luer binary fused ring, a saturated or unsaturated ring.)}
2. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (4).

        Chemical Formula (2) Chemical Formula (3) Chemical Formula (4)

   

   In the formulas (2) to (4), R ^{1 to 13} , L, Ar ^{1 , 2} , n are the same as R ^{1 to 13} , L, Ar ^{1 , 2} , n defined in the formula (1) of claim 1. .
3. The method of claim 1,

   The compound of formula (1) is represented by the following formula (5).

           Formula (5)

   

   In the above formula (5),

   1) R ^{1 ~ 13} , A, L, Ar ² , n is the same as R ^{1 ~ 13} , A, L, Ar ² , n defined in the formula (1) of claim 1,

   2) R ', R "is hydrogen; C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₃ ~ fused ring group of a C ₆₀ aliphatic chain and C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ alkyl group; an alkenyl group of C ₂ ~ C _20; selected from the group consisting of, or combined with each other by the compound as a spy Can be formed,

   3) o is an integer from 0 to 3,

   4) R ^14-18 is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); selected from the group consisting of or adjacent to R ¹⁸ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ are bonded to each other aromatic Or heterocycle.
4. The method of claim 1,

   A compound characterized by the above formula (1) is represented by the following formula (6).

              Formula (6)

   

   In the above formula (6),

   1) R ^{1 ~ 13} , A, L, Ar ² , n, m is the same as R ^{1 ~ 13} , A, L, Ar ² , n, m defined in the formula (1) of claim 1,

   2) o is the same as o defined in the formula (5) of claim 3,

   3) X is O or S,

   4) R ^{18 ~ 22} is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); selected from the group consisting of or adjacent to R ¹⁸ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ²¹ and R ²² are bonded to each other and aromatic Or heterocycle.
5. A compound according to claim 1, which is selected from the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
6. A first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode.

   The organic material layer comprises an organic electric device, characterized in that it contains a compound according to any one of claims 1 to 5.
7. The method of claim 6,

   An organic electric device further comprising a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer.
8. The method of claim 6,

   The organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process
9. The method of claim 6,

   The organic material layer is an organic electrical device comprising the compound as a hole transport material
10. The method of claim 6,

    An organic electric device, characterized in that the same or different compounds of the compound according to any one of claims 1 to 5 are mixed and used in the organic material layer.
11. Claim 6 display device comprising the organic electroluminescent element; And a controller for driving the display device.
12. The method of claim 11,

    The organic electronic device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting device.

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