KR101507423B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention New The present invention relates to a compound, an organic electric device using the same, and an electronic device, and can improve the luminous efficiency, color purity and lifetime of the device and lower the driving voltage.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

TECHNICAL FIELD [0001] The present invention relates to a compound, an organic electric device including the same, and an electronic device thereof.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of 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 material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

On the other hand, the diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, is delayed, and stable characteristics such as joule heating generated during driving the device, It is necessary to develop a hole injection layer material having a temperature. It is also reported that the low glass transition temperature of the hole transporting layer material significantly affects the lifetime of the device depending on the characteristics of the uniformity of the thin film surface collapsing during device operation. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a long time, that is, a material having high heat resistance characteristics, is required.

In order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material is supported by a stable and efficient material However, stable and efficient development of an organic material layer for an organic electric device has not yet been sufficiently developed, and therefore development of a new material is continuously required.

It is an object of the present invention to provide a compound capable of improving a high luminous efficiency, a low driving voltage, a high heat resistance, a color purity and a lifetime of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following general formula (1).

In another aspect, the present invention provides an organic electronic device using the compound represented by Formula 1 and an electronic device thereof.

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference numerals even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

The term " halo "or" halogen "as used herein, on the other hand, includes fluorine, chlorine, bromine and iodine unless otherwise specified.

The term "alkyl" or "alkyl group ", as used herein, unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited thereto.

The term "alkenyl" or "alkynyl ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms,

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxy group" as used in the present invention has, unless otherwise stated, 1 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto.

In the present invention, an aryl group or an arylene group means an aromatic group having a single ring or a heterocyclic ring, and the neighboring substituent includes an aromatic ring formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 3 to 60 carbon atoms each containing at least one heteroatom, But includes a single ring as well as a heterocyclic ring and may be formed by bonding adjacent groups.

The term " heterocycloalkyl ", "heterocyclic group ", as used herein, unless otherwise indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, , And neighboring groups may be combined with each other. Furthermore, the "heterocyclic group" may mean an alicyclic group and / or an aromatic group including a hetero atom.

As used herein, the term "heteroatom " refers to N, O, S, P and Si, unless otherwise indicated.

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

Unless otherwise indicated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or hetero ring having 6 to 60 carbon atoms.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention alkoxy group, C ₁ ~ C ₂₀ alkyl amine group of _20, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron of Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group, and is not limited to these substituents.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Having an organic compound layer containing a compound represented by the general formula (1). In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

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

The compound according to the present invention applied to the organic material layer may be used as a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, .

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (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 a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

In addition, the organic material layer can be formed using a variety of polymer materials by a solution process other than a vapor deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, The organic material layer according to the present invention can be formed by various methods, and therefore the scope of the present invention is not limited by the method of forming the organic material layer.

The organic electroluminescent device according to the present invention may be of a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. 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 compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following formula (1).

           ≪ Formula 1 >

In Formula 1,

(1) Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, tritium, halogen, amino, nitrile, nitro, C ₁ to C ₂₀ alkyl, C ₁ to C ₂₀ alkoxy, C ₁ ~ C ₂₀ alkyl amine group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C _A C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkenyl group, a silane A C ₆ to C ₆₀ aryl group substituted or unsubstituted with a substituent selected from the group consisting of a halogen atom, a halogen atom, a boron group, a germanium group and a C ₂ to C ₆₀ heterocyclic group ; A halogen atom, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, a C ₆ to C ₂₀ alkenyl group, ₆₀ arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl, arylalkenyl a C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ of the group, C ₂ ~ A substituted or unsubstituted C ₂ to C ₆ alkyl group which is substituted or unsubstituted with a substituent selected from the group consisting of a C ₆₀ heterocyclic group, a nitrile group and an acetylene group, and contains at least one heteroatom selected from O, N, S, P and Si A heterocyclic group having 1 to ₆₀ carbon atoms ; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ A substituent selected from the group consisting of a cycloalkyl group, a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, and a C ₂ to C ₆₀ heterocyclic group aryloxy substituted or unsubstituted C ₆ ~ C _30; C ₁ ~ alkenyl group of the C ₂₀ alkyl group, C ₂ ~ C ₂₀ of, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₆₀ aryl group, a C ₆ ~ C ₆₀ substituted with deuterium, C ₇ alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₆₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ ; And hydrogen, deuterium, tritium, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C aryl group of ₆ ~ C _60, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, C ₇ ~ of the silane group substituted with a substituent selected from an aryl alkyl group and an aryl group consisting of C ₈ ~ C ₂₀ alkenyl group of C _20; Lt;

(2) R ₁ To R & lt ; _{12 &} gt ; are each independently of the other hydrogen ; Deuterium ; Tritium ; Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₅ ~ C ₆₀ of the arylamine group, C ₁ ~ for C ₆₀ alkylthiophene group, C ₆ ~ C ₆₀ aryl thiophene group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, an arylalkenyl group of C ₈ ~ C _60, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium And a substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group, which is substituted or unsubstituted with a substituent selected from the group consisting of A C ₆ to C ₆₀ aryl group ; C ₁ ~ alkenyl group of the C ₂₀ alkyl group, C ₂ ~ C ₂₀ of, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₆₀ aryl group, a C ₆ ~ C ₆₀ substituted with deuterium, C ₇ alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₆₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ ; Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a substituted C with deuterium in Substituted or unsubstituted with a substituent selected from the group consisting of a C ₆ to C ₆₀ aryl group, a C ₇ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₂ to C ₆₀ heterocyclic group, a nitrile group and an acetylene group, unsubstituted C ₂ ~ C ₄₀ alkenyl group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ A substituent selected from the group consisting of a cycloalkyl group, a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, and a C ₂ to C ₆₀ heterocyclic group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, tritium, a halogen group, nitrile group, nitro group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₆ ~ aryl of C ₆₀ an amine group, C ₁ ~ C import of ₆₀ alkylthio, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C of ₃ ~ C ₆₀ cycloalkyl group, C ₆ ~ aryl group, a heavy hydrogen of the C ₆₀ of the substituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a group heterocyclic substituted or unsubstituted C ₂ ~ C ₆₀ ring to A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with a substituent selected from the group consisting of O, N, S, P and Si and contains at least one hetero atom ; A condensed ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₆ to C ₆₀ aryl group, a C ₈ to C ₆₀ arylalkenyl group And a heterocyclic group having ₂ to ₆₀ carbon atoms, which is substituted or unsubstituted with a substituent selected from the group consisting of An amine group ; A nitro group ; A nitrile group ; Amide group; And a silane group ; , ≪ / RTI >

(3) R ₆ and R ₇ , R ₉ and R ₁₀ , R ₁₀ and R ₁₁ , and R ₁₁ and R ₁₂ each may combine with adjacent groups to form a saturated or unsaturated ring.

Specifically, the compound represented by the formula (1) may be one of the following formulas (2) to (6).

More specifically, the compound represented by Formula 1 may be one of the following compounds P1-1 to P6-46.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

The final products according to the present invention are prepared by reacting with one of Sub C and Sub 1 to Sub 5 as shown in Scheme 1 below.

<Reaction Scheme 1>

Sub  C synthetic method

Sub C can be prepared by the following reaction formula.

Sub  C Synthetic example  (One)

<Reaction Scheme 2>

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 equivalent) was added to the corresponding amount of toluene followed by addition of C-1-1 (1 equivalent) equivalents), NaO t -Bu (after 3 eq.) were added to an amount corresponding to, the reflux in 100 ℃ stirring for 8 hours, extracted with water MC and the organic layer was dried with MgSO ₄ and concentrated to produce organic silicagel column And recrystallized to obtain the product.

Sub  C Synthetic example  (2)

<Reaction Scheme 3>

In Scheme 3, the intermediate and final compound C-2 were prepared by the following method.

(1) Synthesis of intermediate C-2-3

To the round flask was added the corresponding amount of C-2-1 (1 equivalent), C-2-2 (1 equivalent), PdCl ₂ (PPh ₃ ) ₂ (0.03 eq.), CuI (0.03 eq.), K ₂ CO ₃ ) Were mixed in DMF, and the mixture was refluxed for 4 hours at 100 ° C., extracted with MC and water. The organic layer was dried with MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain a product.

(2) Synthesis of intermediate C-2-4

Add the mixture of C-2-3 (1 equivalent) and KOt-Bu (2 equivalents) and NMP (N-Methylpyrrolidone) to a round flask and stir at room temperature for 5 hours. After extraction with MC and water, the organic layer was dried with MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

(3) Synthesis of Final Compound C-2

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) In toluene followed by the addition of C-2-4 (1 eq.) And C- 2-5 ) And NaO t -Bu (3 equivalents), respectively. The mixture was refluxed at 100 ° C for 8 hours, extracted with MC and water. The organic layer was dried over MgSO ₄ and concentrated. The product is recrystallized.

Sub  C Synthetic example  (3)

<Reaction Scheme 4>

In Scheme 4, the intermediate and final compound C-3 can be prepared by the following synthesis method.

(1) Synthesis of intermediate C-3-3

Round flask to C-3-1 (1 eq.), C-3-2 (1 eq.) Quantity and Pd (OAc) ₂ which is the (0.05 eq.), D ^t BPF (0.1 eq), K ₂ CO ₃ (2.5 eq. ) Was mixed with NMP (N-Methylpyrrolidone), and the mixture was refluxed at 120 ° C for 12 hours. The mixture was refluxed for 12 hours. The mixture was extracted with MC and water. The organic layer was dried with MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized .

(2) Synthesis of Final Compound C-3

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) In toluene followed by the addition of C-3-3 (1 eq.) And C- ) And NaO t- Bu (3 equivalents), respectively, and the mixture was refluxed at 100 ° C for 8 hours. After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Sub  C Synthetic example  (4)

<Reaction Scheme 5>

In the above Reaction Scheme 5, the intermediate and the final compound C-4 were synthesized by the following method.

(1) Synthesis of intermediate C-4-3

C-4-1 (1 eq.) Is mixed with THF in a round flask, followed by stirring while cooling to -40 ° C. Add the appropriate amount of C-4-2 (3 equivalents) slowly and stir at -40 ° C for 3 hours. After the reaction is completed, the reaction mixture is warmed to room temperature, and the organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain a product.

(2) Synthesis of Final Compound C-4

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) Were added to the round flask after mixing with C- 4-3 (1 eq.) And C- 4-4 And NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of the Sub C compound synthesized using the above Synthesis Example are shown below, but the present invention is not limited thereto, and their FD-MS is shown in Table 1 below.

compound FD-MS compound FD-MS Sub C-1 _{m / z = 271.00 (C 14} H 10 BrN = 272.14) Sub C-2 m / z = 423.06 (C ₂₆ H ₁₈ BrN = 424.33) Sub C-3 _{m / z = 321.02 (C 18} H 12 BrN = 322.20) Sub C-4 m / z = 347.03 (C ₂₀ H ₁₄ BrN = 348.24) Sub1 C-5 _{m / z = 424.06 (C 25} H 17 BrN 2 = 425.32) Sub C-6 _{m / z = 349.02 (C 18} H 12 BrN 3 = 350.21) Sub C-7 m / z = 376.99 (C ₂₀ H ₁₂ BrNS 378.28 =) Sub C-8 _{m / z = 403.04 (C 22} H 18 BrNSi = 404.37) Sub C-9 _{m / z = 301.01 (C 15} H 12 BrNO = 302.17) Sub C-10 _{m / z = 386.04 (C 22} H 15 Br 2 = 387.27) Sub C-11 _{m / z = 288.99 (C 14} H 9 BrFN = 290.13) Sub C-12 _{m / z = 321.02 (C 18} H 12 BrN = 322.20) Sub C-13 _{m / z = 473.08 (C 30} H 20 BrN = 474.39) Sub C-14 _{m / z = 371.03 (C 22} H 14 BrN = 372.26) Sub C-15 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub C-16 m / z = 474.07 (C ₂₉ H ₁₉ BrN ₂ = 475.38) Sub C-17 _{m / z = 399.04 (C 22} H 14 BrN 3 = 400.27) Sub C-18 m / z = 427.00 (C ₂₄ H ₁₄ BrNS = 428.34) Sub C-19 m / z = 453.05 (C ₂₆ H ₂₀ BrNSi = 454.43) Sub C-20 _{m / z = 351.03 (C 19} H 14 BrNO = 352.22) Sub C-21 m / z = 436.06 (C ₂₆ H ₁₇ BrN ₂ = 437.33) Sub C-22 _{m / z = 339.01 (C 18} H 11 BrFN = 340.19)

One of the reactants in Scheme 1, S1, was prepared as follows.

S 1 synthesis method

Reaction Scheme S 1 can be synthesized by the reaction path of Scheme 6 below.

<Reaction Scheme 6>

In Scheme 6, intermediate S-1-2 and final compound S1 were synthesized by the following method.

(1) Synthesis of intermediate S-1-2

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) Were added to the round flask following the addition of S-1-1 (1 eq.) And aryl halide compound NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(2) Synthesis of S 1

S-1-2 (1 eq.) And bis (pinacolato) diboron (1.3 eq.) Were mixed in DMF and then PdCl ₂ (DPPF) (0.03 eq.) And AcOK The mixture was stirred at reflux for 3 hours. The organic layer extracted with MC and water was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

S2, one of the reactants in Scheme 1, was prepared by the following method.

S 2 synthesis method

Scheme S 2 can be synthesized by the reaction path of the following reaction formula (7).

<Reaction Scheme 7>

(1) Synthesis of intermediate S-2-1

The Round flask boronic acid compound (1 equivalent), nitro compound (1 eq) that after mixing volume and THF was added Pd (PPh _{3) 4} (0.05 equiv.), NaOH aqueous solution, and reflux was stirred for 12 hours at 70 ℃ to the After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(2) Synthesis of intermediate S-2-2

After mixing dichlorobenzene and S-2-1 (1 equivalent) and S-2-1 (1 equivalent) in a round flask, dichlorobenzene was removed by stirring at 130 ° C for 24 hours under reduced pressure, and then extracted with MC and water. Dried over MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(3) Synthesis of intermediate S-2-3

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the corresponding amount of S-2-2 (1 eq.) And iodo NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(4) Synthesis of final compound S 2

S-2-3 (1 eq.) And bis (pinacolato) diborn (1.3 eq.) In DMF were added to the round flask followed by PdCl ₂ (DPPF) (0.03 eq.) And AcOK After refluxing for 3 hrs. At room temperature, the organic layer extracted with MC and water was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

One of the reactants in Scheme 1, S3, was prepared as follows.

S 3 synthesis method

Scheme 3 can be synthesized by the reaction pathway of Scheme 8 below.

<Reaction Scheme 8>

In the above Reaction Scheme 8, the intermediate and the final compound S3 were synthesized by the following method.

(1) Synthesis of intermediate S-3-1

The Round flask boronic acid compound (1 equivalent), nitro compound (1 eq) that after mixing volume and THF was added Pd (PPh _{3) 4} (0.05 equiv.), NaOH aqueous solution, and reflux was stirred for 12 hours at 70 ℃ to the After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(2) Synthesis of intermediate S-3-2

The mixture was mixed with dichlorobenzene in an amount corresponding to S-3-1 (1 equivalent) and TPP (3 equivalents) in a round flask and then refluxed with stirring at 140 to 160 ° C for 24 hours. After removing dichlorobenzene by reduced pressure, The organic layer is dried over MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(3) Synthesis of intermediate S-3-3

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the appropriate amount of S-3-2 (1 eq.) And Iodo NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(4) Synthesis of Final Compound S 3

S-3-3 (1 eq.) And bis (pinacolato) diboron (1.3 eq.) Were mixed in DMF and then PdCl ₂ (DPPF) (0.03 eq.) And AcOK After refluxing for 3 hrs. At room temperature, the organic layer extracted with MC and water was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

One of the reactants in Scheme 1, S4, was prepared as follows.

S 4 synthesis method

Scheme 4 can be synthesized by the reaction path of Scheme 9 below.

<Reaction Scheme 9>

In the above Reaction Scheme 9, the intermediate and the final compound S4 were prepared in the following manner.

(1) Synthesis of intermediate S-4-1

The Round flask boronic acid compound (1 equivalent), nitro compound (1 eq) that after mixing volume and THF was added Pd (PPh _{3) 4} (0.05 equiv.), NaOH aqueous solution, and reflux was stirred for 12 hours at 70 ℃ to the After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(2) Synthesis of intermediate S-4-2

After mixing dichlorobenzene with S-4-1 (1 equivalent) and S-4-1 (1 equivalent) in a round flask, the mixture was refluxed at 130 ° C for 24 hours under reduced pressure and dichlorobenzene was removed. MC and water were extracted with MgSO ₄ , dried and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(3) Synthesis of intermediate S-4-3

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the corresponding amount of S-4-2 (1 eq.) And Iodo NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(4) Final compound S 4 of  synthesis

S-3-3 (1 eq.) And bis (pinacolato) diboron (1.3 eq.) Were mixed in DMF and then PdCl ₂ (DPPF) (0.03 eq.) And AcOK After refluxing for 3 hrs. At room temperature, the organic layer extracted with MC and water was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

One of the reactants in Scheme 1, S5, was prepared as follows.

S 5 synthetic method

Scheme 5 can be synthesized by the reaction path of Scheme 10 below.

<Reaction formula 10>

In Scheme 10, the intermediate and the final compound S5 were prepared as follows.

(1) Synthesis of intermediate S-5-1

Nitro compound (1 eq.), Triphenylphosphine (2.5 eq.) And o-Dichlorobenzene were placed and then refluxed to 180 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized.

(2) Synthesis of intermediate S-5-2

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) And NaO (0.1 eq.) Were added to the round flask following the addition of S-5-1 (1 eq.) And Iodo t- Bu (3 eq.), respectively, and the mixture was refluxed at 100 ° C for 8 hours. The organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(3) Synthesis of intermediate S-5-3

After mixing with an amount of S-5-2 (1 equivalent) and NBS (1 equivalent) in a round flask, the reaction mixture was refluxed for 24 hours at room temperature and then reduced in pressure to remove dichlorobenzene. The organic layer extracted with MC and water was washed with MgSO ₄ , dried and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product.

(4) Final compound S 5 of  synthesis

PdCl ₂ (DPPF) (0.03 eq.) And AcOK (3 eq.) Were added to the round flask, followed by addition of S-5-3 (1 eq.) And bis (pinacolato diboron After refluxing for 3 hrs. At room temperature, the organic layer extracted with MC and water was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain the product.

이다.
On the other hand, the compounds synthesized by the synthesis method of S 1 to S 5 are as follows, but the present invention is not limited thereto. B (pin) in the following formula

to be.

_

_

FD-MS of the compounds ST 1-1 to ST 5-13 are shown in Table 2 below.

compound FD-MS compound FD-MS ST1-1 m / z = 369.19 (C ₂₄ H ₂₄ BNO ₂ = 369.26) ST 1-2 _{m / z = 419.21 (C 28} H 26 BNO 2 = 419.32) ST1-3 _{m / z = 419.21 (C 28} H 26 BNO 2 = 419.32) ST 1-4 _{m / z = 445.22 (C 30} H 28 BNO 2 = 445.36) ST1-5 m / z = 495.24 (C ₃₄ H ₃₀ BNO ₂ = 495.42) ST1-6 m / z = 521.25 (C ₃₆ H ₃₂ BNO ₂ = 521.46) ST1-7 _{m / z = 522.25 (C 35} H 31 BN 2 O 2 = 522.44) ST1-8 m / z = 523.24 (C ₃₄ H ₃₀ BN ₃ O ₂ = 523.43) ST1-9 _{m / z = 485.25 (C 33} H 32 BNO 2 = 485.42) ST1-10 m / z = 609.28 (C ₄₃ H ₃₆ BNO ₂ = 609.56) ST1-11 m / z = 607.27 (C ₄₃ H ₃₄ BNO ₂ = 607.55) ST1-12 m / z = 598.28 (C ₄₁ H ₃₅ BN ₂ O ₂ = 598.54) ST1-13 _{m / z = 447.21 (C 28} H 26 BN 3 O 2 = 447.34) ST1-14 _{m / z = 463.21 (C 30} H 27 BFNO 2 = 463.35) ST1-15 m / z = 475.23 (C ₃₁ H ₃₀ BNO ₃ = 475.39) ST1-16 m / z = 598.28 (C ₄₁ H ₃₅ BN ₂ O ₂ = 598.54) ST1-17 m / z = 662.31 (C ₄₆ H ₃₉ BN ₂ O ₂ = 662.63) ST2-1 _{m / z = 419.21 (C 28} H 26 BNO 2 = 419.32) ST2-2 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST2-3 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST2-4 m / z = 495.24 (C ₃₄ H ₃₀ BNO ₂ = 495.42) ST2-5 m / z = 545.25 (C ₃₈ H ₃₂ BNO ₂ = 545.48) ST2-6 m / z = 571.27 (C ₄₀ H ₃₄ BNO ₂ = 571.51) ST2-7 m / z = 572.26 (C ₃₉ H ₃₃ BN ₂ O ₂ = 572.50) ST2-8 m / z = 573.26 (C ₃₈ H ₃₂ BN ₃ O ₂ = 573.49) ST2-9 m / z = 535.27 (C ₃₇ H ₃₄ BNO ₂ = 535.48) ST2-10 m / z = 659.30 (C ₄₇ H ₃₈ BNO ₂ = 659.62) ST2-11 m / z = 657.28 (C ₄₇ H ₃₆ BNO ₂ = 657.61) ST2-12 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST2-13 m / z = 497.23 (C ₃₂ H ₂₈ BN ₃ O ₂ = 497.39) ST2-14 m / z = 513.23 (C ₃₄ H ₂₉ BFNO ₂ = 513.41) ST2-15 _{m / z = 525.25 (C 35} H 32 BNO 3 = 525.44) ST2-16 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST2-17 m / z = 712.33 (C ₅₀ H ₄₁ BN ₂ O ₂ = 712.68) ST3-1 _{m / z = 419.21 (C 28} H 26 BNO 2 = 419.32) ST3-2 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST3-3 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST3-4 m / z = 495.24 (C ₃₄ H ₃₀ BNO ₂ = 495.42) ST3-5 m / z = 545.25 (C ₃₈ H ₃₂ BNO ₂ = 545.48) ST3-6 m / z = 571.27 (C ₄₀ H ₃₄ BNO ₂ = 571.51) ST3-7 m / z = 572.26 (C ₃₉ H ₃₃ BN ₂ O ₂ = 572.50) ST3-8 m / z = 573.26 (C ₃₈ H ₃₂ BN ₃ O ₂ = 573.49) ST3-9 m / z = 535.27 (C ₃₇ H ₃₄ BNO ₂ = 535.48) ST3-10 m / z = 659.30 (C ₄₇ H ₃₈ BNO ₂ = 659.62) ST3-11 m / z = 657.28 (C ₄₇ H ₃₆ BNO ₂ = 657.61) ST3-12 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST3-13 m / z = 497.23 (C ₃₂ H ₂₈ BN ₃ O ₂ = 497.39) ST3-14 m / z = 513.23 (C ₃₄ H ₂₉ BFNO ₂ = 513.41) ST3-15 _{m / z = 525.25 (C 35} H 32 BNO 3 = 525.44) ST3-16 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST3-17 m / z = 712.33 (C ₅₀ H ₄₁ BN ₂ O ₂ = 712.68) ST4-1 _{m / z = 419.21 (C 28} H 26 BNO 2 = 419.32) ST4-2 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST4-3 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST4-4 m / z = 495.24 (C ₃₄ H ₃₀ BNO ₂ = 495.42) ST4-5 m / z = 545.25 (C ₃₈ H ₃₂ BNO ₂ = 545.48) ST4-6 m / z = 571.27 (C ₄₀ H ₃₄ BNO ₂ = 571.51) ST4-7 m / z = 572.26 (C ₃₉ H ₃₃ BN ₂ O ₂ = 572.50) ST4-8 m / z = 573.26 (C ₃₈ H ₃₂ BN ₃ O ₂ = 573.49) ST4-9 m / z = 535.27 (C ₃₇ H ₃₄ BNO ₂ = 535.48) ST4-10 m / z = 659.30 (C ₄₇ H ₃₈ BNO ₂ = 659.62) ST4-11 m / z = 657.28 (C ₄₇ H ₃₆ BNO ₂ = 657.61) ST4-12 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST4-13 m / z = 497.23 (C ₃₂ H ₂₈ BN ₃ O ₂ = 497.39) ST4-14 m / z = 513.23 (C ₃₄ H ₂₉ BFNO ₂ = 513.41) ST4-15 _{m / z = 525.25 (C 35} H 32 BNO 3 = 525.44) ST4-16 m / z = 648.29 (C ₄₅ H ₃₇ BN ₂ O ₂ = 648.60) ST4-17 m / z = 712.33 (C ₅₀ H ₄₁ BN ₂ O ₂ = 712.68) ST5-1 m / z = 469.22 (C ₃₂ H ₂₈ BNO ₂ = 469.38) ST5-2 m / z = 519.24 (C ₃₆ H ₃₀ BNO ₂ = 519.44) ST5-3 m / z = 519.24 (C ₃₆ H ₃₀ BNO ₂ = 519.44) ST5-4 m / z = 545.25 (C ₃₈ H ₃₂ BNO ₂ = 545.48) ST5-5 m / z = 698.31 (C ₄₉ H ₃₃ BN ₂ O ₂ = 698.66) ST5-6 m / z = 622.28 (C ₄₃ H ₃₅ BN ₂ O ₂ = 622.56) ST5-7 m / z = 623.27 (C ₄₂ H ₃₄ BN ₃ O ₂ = 623.55) ST5-8 m / z = 547.24 (C ₃₆ H ₃₀ BN ₃ O ₂ = 547.45) ST5-9 m / z = 585.28 (C ₄₁ H ₃₆ BNO ₂ = 585.54) ST5-10 m / z = 709.32 (C ₅₁ H ₄₀ BNO ₂ = 709.68) ST5-11 m / z = 707.30 (C ₅₁ H ₃₈ BNO ₂ = 707.66) ST5-12 m / z = 621.28 (C ₄₄ H ₃₆ BNO ₂ = 621.57) ST5-13 m / z = 595.27 (C ₄₂ H ₃₄ BNO ₂ = 595.54)

A method for synthesizing the final compound according to Scheme 1 is as follows.

The final compound P1  To P6  Synthetic example

S1 ~ S5 compound (1 equivalent), Sub C compound (1 eq.) Pd (PPh ₃₎ After mixing volume and THF for the ₄ (0.05 eq.), 12 hours at the addition of NaOH aqueous solution, 70 ℃ the Round flask After stirring and refluxing, the organic layer extracted with MC and water is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain the product. FD-MS of the obtained final compounds P1-1 to P6-46 are shown in Table 3 below.

compound FD-MS compound FD-MS P1-1 m / z = 434.18 (C ₃₂ H ₂₂ N ₂ = 434.53) P1-2 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P1-3 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P1-4 m / z = 510.21 (C ₃₈ H ₂₆ N ₂ = 510.63) P1-5 m / z = 663.27 (C ₄₉ H ₃₃ N ₃ = 663.81) P1-6 m / z = 587.24 (C ₄₃ H ₂₉ N ₃ = 587.71) P1-7 m / z = 588.23 (C ₄₂ H ₂₈ N ₄ = 588.70) P1-8 _{m / z = 512.20 (C 36} H 24 N 4 = 512.60) P1-9 m / z = 550.24 (C ₄₁ H ₃₀ N ₂ = 550.69) P1-10 m / z = 674.27 (C ₅₁ H ₃₄ N ₂ = 674.83) P1-11 m / z = 672.26 (C ₅₁ H ₃₂ N ₂ = 672.81) P1-12 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.72) P1-13 m / z = 663.27 (C ₄₉ H ₃₃ N ₃ = 663.81) P1-14 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.89) P1-15 m / z = 528.20 (C ₃₈ H ₂₅ FN ₂ = 528.62) P1-16 m / z = 540.22 (C ₃₉ H ₂₈ N ₂ O = 540.65) P1-17 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P1-18 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P1-19 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P1-20 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P1-21 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P1-22 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P1-23 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P1-24 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P1-25 m / z = 600.26 (C ₄₅ H ₃₂ N ₂ = 600.75) P1-26 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) P1-27 m / z = 722.27 (C ₅₅ H ₃₄ N ₂ = 722.87) P1-28 m / z = 855.36 (C ₆₄ H ₄₅ N ₃ = 856.06) P1-29 m / z = 510.21 (C ₃₈ H ₂₆ N ₂ = 510.63) P1-30 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P1-31 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P1-32 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.72) P1-33 m / z = 739.30 (C ₅₅ H ₃₇ N ₃ = 739.90) P1-34 m / z = 663.27 (C ₄₉ H ₃₃ N ₃ = 663.81) P1-35 m / z = 664.26 (C ₄₈ H ₃₂ N ₄ = 664.79) P1-36 m / z = 588.23 (C ₄₂ H ₂₈ N ₄ = 588.70) P1-37 m / z = 626.27 (C ₄₇ H ₃₄ N ₂ = 626.79) P1-38 m / z = 750.30 (C ₅₇ H ₃₈ N ₂ = 750.93) P1-39 m / z = 748.29 (C ₅₇ H ₃₆ N ₂ = 748.91) P1-40 m / z = 587.24 (C ₄₃ H ₂₉ N ₃ = 587.71) P1-41 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P1-42 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.73) P1-43 m / z = 642.25 (C ₄₆ H ₃₄ N ₂ Si = 642.86) P1-44 m / z = 616.25 (C ₄₅ H ₃₂ N ₂ O = 616.75) P1-45 m / z = 549.22 (C ₄₀ H ₂₇ N ₃ = 549.66) P1-46 m / z = 578.22 (C ₄₂ H ₂₇ FN ₂ = 578.68) P2-1 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P2-2 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P2-3 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P2-4 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P2-5 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P2-6 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P2-7 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P2-8 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P2-9 m / z = 600.26 (C ₄₅ H ₃₂ N ₂ = 600.75) P2-10 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) P2-11 m / z = 722.27 (C ₅₅ H ₃₄ N ₂ = 722.87) P2-12 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P2-13 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P2-14 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) P2-15 m / z = 578.22 (C ₄₂ H ₂₇ FN ₂ = 578.68) P2-16 m / z = 590.24 (C ₄₃ H ₃₀ N ₂ O = 590.71) P2-17 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P2-18 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P2-19 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P2-20 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P2-21 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P2-22 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P2-23 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P2-24 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P2-25 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) P2-26 m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) P2-27 m / z = 772.29 (C ₅₉ H ₃₆ N ₂ = 772.93) P2-28 m / z = 905.38 (C ₆₈ H ₄₇ N ₃ = 906.12) P2-29 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P2-30 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P2-31 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P2-32 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P2-33 m / z = 789.31 (C ₅₉ H ₃₉ N ₃ = 789.96) P2-34 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P2-35 m / z = 714.28 (C ₅₂ H ₃₄ N ₄ = 714.85) P2-36 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P2-37 m / z = 676.29 (C ₅₁ H ₃₆ N ₂ = 676.84) P2-38 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) P2-39 m / z = 798.30 (C ₆₁ H ₃₈ N ₂ = 798.97) P2-40 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P2-41 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P2-42 m / z = 640.20 (C ₄₆ H ₂₈ N ₂ S = 640.79) P2-43 _{m / z = 692.26 (C 50} H 36 N 2 Si = 692.92) P2-44 m / z = 666.27 (C ₄₉ H ₃₄ N ₂ O = 666.81) P2-45 m / z = 599.24 (C ₄₄ H ₂₉ N ₃ = 599.72) P2-46 m / z = 628.23 (C ₄₆ H ₂₉ FN ₂ = 628.73) P3-1 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P3-2 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P3-3 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P3-4 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P3-5 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P3-6 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P3-7 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P3-8 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P3-9 m / z = 600.26 (C ₄₅ H ₃₂ N ₂ = 600.75) P3-10 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) P3-11 m / z = 722.27 (C ₅₅ H ₃₄ N ₂ = 722.87) P3-12 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P3-13 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P3-14 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) P3-15 m / z = 578.22 (C ₄₂ H ₂₇ N ₂ = 578.68) P3-16 m / z = 590.24 (C ₄₃ H ₃₀ N ₂ O = 590.71) P3-17 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P3-18 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P3-19 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P3-20 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P3-21 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P3-22 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P3-23 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P3-24 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P3-25 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) P3-26 m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) P3-27 m / z = 772.29 (C ₅₉ H ₃₆ N ₂ = 772.93) P3-28 m / z = 855.36 (C ₆₄ H ₄₅ N ₃ = 856.06) P3-29 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P3-30 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P3-31 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P3-32 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P3-33 m / z = 789.31 (C ₅₉ H ₃₉ N ₃ = 789.96) P3-34 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P3-35 m / z = 714.28 (C ₅₂ H ₃₄ N ₄ = 714.85) P3-36 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P3-37 m / z = 676.29 (C ₅₁ H ₃₆ N ₂ = 676.84) P3-38 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) P3-39 m / z = 798.30 (C ₆₁ H ₃₈ N ₂ = 798.97) P3-40 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P3-41 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P3-42 m / z = 640.20 (C ₄₆ H ₂₈ N ₂ S = 640.79) P3-43 _{m / z = 692.26 (C 50} H 36 N 2 Si = 692.92) P3-44 m / z = 666.27 (C ₄₉ H ₃₄ N ₂ O = 666.81) P3-45 m / z = 599.24 (C ₄₄ H ₂₉ N ₃ = 599.72) P3-46 m / z = 628.23 (C ₄₆ H ₂₉ FN ₂ = 628.73) P4-1 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P4-2 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P4-3 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P4-4 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P4-5 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P4-6 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P4-7 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P4-8 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P4-9 m / z = 600.26 (C ₄₆ H ₃₂ N ₂ = 600.75) P4-10 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) P4-11 m / z = 722.27 (C ₅₅ H ₃₄ N ₂ = 722.87) P4-12 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P4-13 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P4-14 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) P4-15 m / z = 578.22 (C ₄₂ H ₂₇ FN ₂ = 578.68) P4-16 m / z = 590.24 (C ₄₃ H ₃₀ N ₂ O = 590.71) P4-17 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P4-18 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P4-19 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P4-20 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P4-21 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P4-22 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P4-23 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P4-24 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P4-25 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) P4-26 m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) P4-27 m / z = 772.29 (C ₅₉ H ₃₆ N ₂ = 772.93) P4-28 m / z = 905.38 (C ₆₈ H ₄₇ N ₃ = 906.12) P4-29 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P4-30 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P4-31 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P4-32 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P4-33 m / z = 789.31 (C ₅₉ H ₃₉ N ₃ = 789.96) P4-34 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P4-35 m / z = 714.28 (C ₅₂ H ₃₄ N ₄ = 714.85) P4-36 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P4-37 m / z = 676.29 (C ₅₁ H ₃₆ N ₂ = 676.84) P4-38 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) P4-39 m / z = 798.30 (C ₆₁ H ₃₈ N ₂ = 798.97) P4-40 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P4-41 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P4-42 m / z = 640.20 (C ₄₆ H ₂₈ N ₂ S = 640.79) P4-43 _{m / z = 692.26 (C 50} H 36 N 2 Si = 692.92) P4-44 m / z = 666.27 (C ₄₉ H ₃₄ N ₂ O = 666.81) P4-45 m / z = 599.24 (C ₄₄ H ₂₉ N ₃ = 599.72) P4-46 m / z = 628.23 (C ₄₆ H ₂₉ FN ₂ = 628.73) P5-1 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P5-2 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P5-3 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P5-4 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P5-5 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P5-6 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P5-7 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P5-8 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P5-9 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) P5-10 m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) P5-11 m / z = 772.29 (C ₅₉ H ₃₆ N ₂ = 772.93) P5-12 m / z = 686.27 (C ₅₂ H ₃₄ N ₂ = 686.84) P5-13 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P5-14 m / z = 634.24 (C ₄₈ H ₃₀ N ₂ = 634.77) P5-15 m / z = 634.24 (C ₄₈ H ₃₀ N ₂ = 634.77) P5-16 m / z = 660.26 (C ₅₀ H ₃₂ N ₂ = 660.80) P5-17 m / z = 813.31 (C ₆₁ H ₃₉ N ₃ = 813.98) P5-18 m / z = 737.28 (C ₅₅ H ₃₅ N ₃ = 737.89) P5-19 m / z = 738.28 (C ₅₄ H ₃₄ N ₄ = 738.87) P5-20 m / z = 662.25 (C ₄₈ H ₃₀ N ₄ = 662.78) P5-21 m / z = 700.29 (C ₅₃ H ₃₆ N ₂ = 700.87) P5-22 m / z = 824.32 (C ₆₃ H ₄₀ N ₂ = 825.01) P5-23 m / z = 822.30 (C ₆₃ H ₃₈ N ₂ = 822.99) P5-24 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) P5-25 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P5-26 m / z = 660.26 (C ₅₀ H ₃₂ N ₂ = 660.80) P5-27 m / z = 660.26 (C ₅₀ H ₃₂ N ₂ = 660.80) P5-28 m / z = 686.27 (C ₅₂ H ₃₄ N ₂ = 686.84) P5-29 m / z = 839.33 (C ₆₃ H ₄₁ N ₃ = 840.02) P5-30 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P5-31 m / z = 764.29 (C ₅₆ H ₃₆ N ₄ = 764.91) P5-32 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P5-33 m / z = 726.30 (C ₅₅ H ₃₈ N ₂ = 726.90) P5-34 m / z = 850.33 (C ₆₅ H ₄₂ N ₂ = 851.04) P5-35 m / z = 848.32 (C ₆₅ H ₄₀ N ₂ = 849.03) P5-36 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P5-37 m / z = 662.25 (C ₄₈ H ₃₀ N ₄ = 662.78) P5-38 _{m / z = 690.21 (C 50} H 30 N 2 S = 690.85) P5-39 m / z = 742.28 (C ₅₄ H ₃₈ N ₂ Si = 742.98) P5-40 m / z = 716.28 (C ₅₃ H ₃₆ N ₂ O = 716.87) P5-41 m / z = 649.25 (C ₄₈ H ₃₁ N ₃ = 649.78) P5-42 m / z = 678.25 (C ₅₀ H ₃₁ FN ₂ = 678.79) P6-1 _{m / z = 484.19 (C 36} H 24 N 2 = 484.59) P6-2 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P6-3 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P6-4 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P6-5 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P6-6 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P6-7 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P6-8 m / z = 562.22 (C ₄₀ H ₂₆ N ₄ = 562.66) P6-9 m / z = 600.26 (C ₄₅ H ₃₂ N ₂ = 600.75) P6-10 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) P6-11 m / z = 722.27 (C ₅₅ H ₃₄ N ₂ = 722.87) P6-12 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P6-13 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P6-14 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) P6-15 m / z = 578.22 (C ₄₂ H ₂₇ FN ₂ = 578.68) P6-16 m / z = 590.24 (C ₄₃ H ₃₀ N ₂ O = 590.71) P6-17 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.65) P6-18 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P6-19 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.71) P6-20 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P6-21 m / z = 763.30 (C ₅₇ H ₃₇ N ₃ = 763.92) P6-22 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.83) P6-23 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.82) P6-24 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P6-25 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) P6-26 m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) P6-27 m / z = 772.29 (C ₅₉ H ₃₆ N ₂ = 772.93) P6-28 m / z = 905.38 (C ₆₈ H ₄₇ N ₃ = 906.12) P6-29 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.69) P6-30 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P6-31 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.74) P6-32 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) P6-33 m / z = 789.31 (C ₅₉ H ₃₉ N ₃ = 789.96) P6-34 m / z = 713.28 (C ₅₃ H ₃₅ N ₃ = 713.87) P6-35 m / z = 714.28 (C ₅₂ H ₃₄ N ₄ = 714.85) P6-36 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.76) P6-37 m / z = 676.29 (C ₅₁ H ₃₆ N ₂ = 676.84) P6-38 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) P6-39 m / z = 798.30 (C ₆₁ H ₃₈ N ₂ = 798.97) P6-40 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.77) P6-41 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.72) P6-42 m / z = 640.20 (C ₄₆ H ₂₈ N ₂ S = 640.79) P6-43 _{m / z = 692.26 (C 50} H 36 N 2 Si = 692.92) P6-44 m / z = 666.27 (C ₄₉ H ₃₄ N ₂ O = 666.81) P6-45 m / z = 599.24 (C ₄₄ H ₂₉ N ₃ = 599.72) P6-46 m / z = 628.23 (C ₄₆ H ₂₉ FN ₂ = 628.73)

In the meantime, although the exemplary synthesis example of the present invention represented by the general formula (1) has been described above, all of them are based on Suzuki cross-coupling reaction, Miyaura boration reaction and Buchwald- Hartwig cross coupling reaction. (Substituents such as Ar _{1 ,} Ar ₂ , and R ₁ to R ₁₂ ) as defined in the above-described formula ( ₁ ) are not bonded to each other. For example, the step of producing S-2-1 in Scheme 7 and the step of producing S-3-1 in Scheme 8 are based on the Suzuki cross-coupilng reaction, and the step C-1 in Scheme 2, the step C-2 in Scheme 3 , The step of producing C3 in Scheme 4, the step of producing C4 in Scheme 5, the step of producing S-1-2 in Scheme 6, the step of producing S-2-3 in Scheme 7, the step of producing S-3-3 in Scheme 8, S-4-3 production step in Scheme 10 and S-5-2 production step in Scheme 10 are all based on the Buchwald-Hartwig cross coupling reaction, and the step S 1 in the reaction formula 6, the step S 2 in the reaction formula 7, S 3 production step in Scheme 9, S 4 production step in Scheme 9, and S 5 production step in Scheme 10 are all based on the Miyaura boration reaction. Therefore, it will be understood by those skilled in the art that the reaction will proceed by the same mechanism for other substituent-bonded compounds other than the exemplified substituents.

Evaluation of manufacturing of organic electric device

First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the organic substrate to form a hole injection layer with a thickness of 60 nm. Then, the compound according to the present invention was vacuum-deposited to a thickness of 20 nm on the hole injection layer to form a hole transport layer . Next, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a light emitting layer host material and Ir (ppy) ₃ [tris (2-phenylpyridine) 1 to a thickness of 30 nm to deposit a light emitting layer. Subsequently, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm as a transport layer, LiF as an alkali metal metal to be an electron injecting layer was deposited to a thickness of 0.2 nm, 150 nm thick, and Al was used as a cathode to fabricate an organic electroluminescent device.

[Comparative Example 1]

An organic electroluminescent device was prepared in the same manner as in Example 8, except that the following Comparative Compound 1 was used instead of the compound of the present invention in forming the hole transport layer.

[Comparative Example 2]

An organic electroluminescent device was prepared in the same manner as in Example 8, except that the following Comparative Compound 2 was used instead of the compound of the present invention in forming the hole transport layer.

[Comparative Example 3]

An organic electroluminescent device was fabricated in the same manner as in Example 8, except that the following Comparative Compound 3 was used instead of the compound of the present invention in forming the hole transport layer.

Electrically-electroluminescent (EL) EL devices were fabricated by photolithography PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices of Example 8 and Comparative Example 1, Comparative Example 2 and Comparative Example 3, The T90 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 300 cd / m 2. The results of measuring the driving voltage, current density, luminance, luminescence efficiency and lifetime of the organic electroluminescent device manufactured according to the compound of Example 8, Comparative Example 1, Comparative Example 2 and Comparative Example 3 are shown in Table 4 It was the same.

compound Driving voltage Current (mA / cm 2) Brightness (cd / m2) Efficiency (cd / A) T (90) Comparative Example (1) Comparative Example (1) 6.2 9.1 300.0 3.3 65.6 Comparative Example (2) Comparative Example (2) 6.0 9.9 300.0 3.0 62.5 Comparative Example (3) Comparative Example (3) 5.8 6.8 300.0 4.4 62.4 Example (1) Compound (1-1) 5.4 5.5 300.0 5.4 139.9 Example (2) The compound (1-2) 5.4 5.3 300.0 5.7 98.8 Example (3) The compound (1-3) 5.7 5.4 300.0 5.5 109.3 Example (4) The compound (1-4) 5.5 6.7 300.0 4.5 108.8 Example (5) Compound (1-5) 5.4 5.5 300.0 5.4 135.3 Example (6) The compound (1-6) 4.7 5.5 300.0 5.5 130.4 Example (7) Compound (1-7) 5.0 5.4 300.0 5.6 133.8 Example (8) Compound (1-8) 5.3 7.0 300.0 4.3 135.2 Example (9) Compound (1-9) 5.2 6.1 300.0 5.0 103.3 Example (10) The compound (1-10) 5.1 5.8 300.0 5.2 111.0 Example (11) The compound (1-11) 4.8 6.7 300.0 4.5 135.0 Example (12) The compound (1-12) 5.0 6.9 300.0 4.3 137.7 Example (13) The compound (1-13) 5.1 6.6 300.0 4.5 142.9 Example (14) The compound (1-14) 4.9 5.9 300.0 5.1 92.5 Example (15) The compound (1-15) 4.8 5.9 300.0 5.1 143.9 Example (16) The compound (1-16) 4.6 6.9 300.0 4.3 110.9 Example (17) The compound (1-17) 5.5 5.4 300.0 5.6 109.0 Example (18) Compound (1-18) 5.0 5.2 300.0 5.7 115.4 Example (19) The compound (1-19) 4.9 6.2 300.0 4.8 126.1 Example (20) Compound (1-20) 5.3 5.6 300.0 5.4 105.1 Example (21) Compound (1-21) 4.7 6.3 300.0 4.8 125.3 Example (22) The compound (1-22) 5.3 6.1 300.0 4.9 103.5 Example (23) Compound (1-23) 5.3 6.0 300.0 5.0 123.5 Example (24) Compound (1-24) 5.2 5.5 300.0 5.5 112.4 Example (25) The compound (1-25) 5.3 5.5 300.0 5.5 129.3 Example (26) Compound (1-26) 4.9 6.8 300.0 4.4 129.8 Example (27) Compound (1-27) 5.0 5.3 300.0 5.7 133.9 Example (28) Compound (1-28) 5.1 6.6 300.0 4.6 135.4 Example (29) Compound (1-29) 4.7 7.1 300.0 4.2 143.7 Example (30) Compound (1-30) 5.4 6.6 300.0 4.6 145.9 Example (31) Compound (1-31) 5.2 6.4 300.0 4.7 109.2 Example (32) Compound (1-32) 5.1 6.1 300.0 4.9 109.3 Example (33) Compound (1-33) 5.4 5.4 300.0 5.5 134.4 Example (34) Compound (1-34) 5.1 7.1 300.0 4.2 115.8 Example (35) Compound (1-35) 4.8 7.0 300.0 4.3 122.0 Example (36) Compound (1-36) 4.9 6.3 300.0 4.8 131.5 Example (37) Compound (1-37) 5.4 5.3 300.0 5.7 135.7 Example (38) Compound (1-38) 4.8 5.3 300.0 5.7 104.2 Example (39) Compound (1-39) 5.0 5.5 300.0 5.4 124.0 Example (40) Compound (1-40) 5.0 5.7 300.0 5.3 118.7 Example (41) Compound (1-41) 5.0 6.8 300.0 4.4 117.0 Example (42) Compound (1-42) 5.1 5.4 300.0 5.6 92.6 Example (43) Compound (1-43) 5.0 6.0 300.0 5.0 147.8 Example (44) Compound (1-44) 5.2 6.1 300.0 5.0 118.6 Example (45) Compound (1-45) 4.7 5.6 300.0 5.4 100.1 Example (46) Compound (1-46) 5.1 5.4 300.0 5.5 117.4 Example (47) Compound (2-1) 5.5 5.8 300.0 5.1 105.1 Example (48) Compound (2-2) 5.5 5.7 300.0 5.2 100.5 Example (49) Compound (2-3) 5.2 5.7 300.0 5.3 99.9 Example (50) Compound (2-4) 4.6 6.4 300.0 4.7 99.6 Example (51) Compound (2-5) 5.2 5.6 300.0 5.4 93.3 Example (52) Compound (2-6) 5.3 5.9 300.0 5.1 144.6 Example (53) Compound (2-7) 5.3 5.6 300.0 5.3 144.5 Example (54) Compound (2-8) 5.4 6.3 300.0 4.8 131.7 Example (55) Compound (2-9) 5.2 5.5 300.0 5.4 144.7 Example (56) Compound (2-10) 5.3 7.1 300.0 4.2 118.7 Example (57) Compound (2-11) 5.0 5.2 300.0 5.7 146.1 Example (58) The compound (2-12) 4.8 6.3 300.0 4.8 118.8 Example (59) The compound (2-13) 5.3 7.0 300.0 4.3 104.3 Example (60) The compound (2-14) 5.4 5.3 300.0 5.7 121.5 Example (61) Compound (2-15) 5.2 6.4 300.0 4.7 146.3 Example (62) The compound (2-16) 5.3 6.3 300.0 4.8 101.6 Example (63) Compound (2-17) 4.8 6.0 300.0 5.0 100.4 Example (64) Compound (2-18) 5.1 6.2 300.0 4.8 109.1 Example (65) Compound (2-19) 5.4 5.3 300.0 5.7 132.2 Example (66) Compound (2-20) 4.9 5.7 300.0 5.3 102.9 Example (67) Compound (2-21) 5.1 5.3 300.0 5.7 127.7 Example (68) Compound (2-22) 5.4 6.9 300.0 4.4 141.5 Example (69) The compound (2-23) 4.7 5.4 300.0 5.5 114.9 Example (70) Compound (2-24) 4.7 5.9 300.0 5.1 140.2 Example (71) Compound (2-25) 4.8 7.0 300.0 4.3 107.3 Example (72) Compound (2-26) 4.7 5.6 300.0 5.3 146.7 Example (73) Compound (2-27) 5.0 6.3 300.0 4.8 108.5 Example (74) Compound (2-28) 4.8 6.0 300.0 5.0 138.9 Example (75) Compound (2-29) 4.8 5.5 300.0 5.4 134.4 Example (76) Compound (2-30) 4.9 5.4 300.0 5.6 134.3 Example (77) Compound (2-31) 4.8 6.5 300.0 4.6 108.0 Example (78) Compound (2-32) 4.6 6.0 300.0 5.0 129.2 Example (79) Compound (2-33) 4.6 5.2 300.0 5.7 104.3 Example (80) Compound (2-34) 5.2 5.5 300.0 5.4 113.8 Example (81) Compound (2-35) 4.8 6.0 300.0 5.0 134.3 Example (82) Compound (2-36) 5.4 7.0 300.0 4.3 141.4 Example (83) Compound (2-37) 4.7 6.1 300.0 5.0 93.2 Example (84) Compound (2-38) 5.1 6.6 300.0 4.6 140.8 Example (85) Compound (2-39) 5.5 6.6 300.0 4.6 122.7 Example (86) Compound (2-40) 5.4 5.5 300.0 5.5 148.6 Example (87) Compound (2-41) 4.7 7.0 300.0 4.3 131.8 Example (88) Compound (2-42) 5.0 6.6 300.0 4.5 108.9 Example (89) Compound (2-43) 5.1 6.6 300.0 4.5 90.1 Example (90) Compound (2-44) 5.4 6.8 300.0 4.4 97.5 Example (91) Compound (2-45) 5.1 6.7 300.0 4.5 114.4 Example (92) Compound (2-46) 5.4 6.6 300.0 4.5 133.4 Example (93) Compound (3-1) 5.5 6.3 300.0 4.8 138.9 Example (94) The compound (3-2) 4.9 6.2 300.0 4.8 121.0 Example (95) Compound (3-3) 5.3 6.7 300.0 4.5 110.9 Example (96) Compound (3-4) 5.2 5.6 300.0 5.4 102.4 Example (97) Compound (3-5) 5.1 5.5 300.0 5.5 133.5 Example (98) Compound (3-6) 5.1 5.2 300.0 5.7 103.1 Example (99) Compound (3-7) 4.7 5.8 300.0 5.1 143.5 Example (100) Compound (3-8) 4.7 5.7 300.0 5.2 110.6 Example (101) Compound (3-9) 5.1 5.8 300.0 5.1 140.6 Example (102) Compound (3-10) 5.1 6.0 300.0 5.0 117.3 Example (103) The compound (3-11) 5.1 5.3 300.0 5.7 119.5 Example (104) The compound (3-12) 5.0 5.9 300.0 5.1 128.6 Example (105) The compound (3-13) 5.1 5.5 300.0 5.5 106.2 Example (106) The compound (3-14) 4.9 5.6 300.0 5.4 130.6 Example (107) The compound (3-15) 4.7 7.0 300.0 4.3 132.0 Example (108) The compound (3-16) 4.7 5.9 300.0 5.1 143.5 Example (109) Compound (3-17) 5.4 5.9 300.0 5.1 92.8 Example (110) Compound (3-18) 5.4 5.5 300.0 5.4 121.9 Example (111) Compound (3-19) 4.8 6.2 300.0 4.9 145.6 Example (112) Compound (3-20) 5.0 5.8 300.0 5.2 99.5 Example (113) Compound (3-21) 4.8 5.7 300.0 5.3 111.9 Example (114) Compound (3-22) 5.2 6.4 300.0 4.7 101.0 Example (115) Compound (3-23) 5.5 5.6 300.0 5.4 111.7 Example (116) Compound (3-24) 5.2 5.9 300.0 5.0 111.5 Example (117) Compound (3-25) 5.3 5.8 300.0 5.2 110.2 Example (118) Compound (3-26) 4.9 5.4 300.0 5.5 146.7 Example (119) Compound (3-27) 4.5 5.1 300.0 5.9 148.5 Example (120) Compound (3-28) 4.6 5.2 300.0 5.7 126.7 Example (121) Compound (3-29) 4.6 5.6 300.0 5.4 147.2 Example (122) Compound (3-30) 4.7 6.0 300.0 5.0 134.3 Example (123) Compound (3-31) 5.0 6.2 300.0 4.9 139.4 Example (124) Compound (3-32) 5.2 6.1 300.0 4.9 115.5 Example (125) Compound (3-33) 5.3 6.2 300.0 4.9 110.5 Example (126) Compound (3-34) 4.8 5.5 300.0 5.4 133.1 Example (127) Compound (3-35) 5.1 5.7 300.0 5.3 127.7 Example (128) Compound (3-36) 5.1 5.4 300.0 5.5 101.8 Example (129) Compound (3-37) 5.3 7.0 300.0 4.3 133.9 Example (130) Compound (3-38) 4.7 6.0 300.0 5.0 121.3 Example (131) Compound (3-39) 5.1 5.7 300.0 5.2 92.4 Example (132) Compound (3-40) 4.7 6.5 300.0 4.6 148.9 Example (133) Compound (3-41) 5.1 6.8 300.0 4.4 90.6 Example (134) Compound (3-42) 4.8 6.0 300.0 5.0 102.2 Example (135) Compound (3-43) 5.5 6.4 300.0 4.7 120.1 Example (136) Compound (3-44) 5.3 6.9 300.0 4.3 149.5 Example (137) Compound (3-45) 4.6 5.7 300.0 5.2 115.7 Example (138) Compound (3-46) 5.1 6.3 300.0 4.8 96.9 Example (139) Compound (4-1) 5.5 5.6 300.0 5.4 119.9 Example (140) Compound (4-2) 4.7 6.3 300.0 4.7 104.1 Example (141) Compound (4-3) 5.2 6.6 300.0 4.5 106.2 Example (142) The compound (4-4) 4.9 6.6 300.0 4.6 138.5 Example (143) Compound (4-5) 4.7 6.2 300.0 4.8 95.9 Example (144) Compound (4-6) 5.1 6.3 300.0 4.8 140.1 Example (145) The compound (4-7) 5.2 5.3 300.0 5.6 110.4 Example (146) Compound (4-8) 5.1 5.4 300.0 5.6 144.1 Example (147) Compound (4-9) 4.8 5.8 300.0 5.2 125.3 Example (148) Compound (4-10) 5.0 5.7 300.0 5.2 140.7 Example (149) The compound (4-11) 5.2 6.8 300.0 4.4 120.7 Example (150) The compound (4-12) 5.3 5.6 300.0 5.4 146.1 Example (151) The compound (4-13) 4.7 5.4 300.0 5.6 145.5 Example (152) The compound (4-14) 4.8 6.1 300.0 4.9 144.9 Example (153) Compound (4-15) 4.7 5.5 300.0 5.5 132.1 Example (154) The compound (4-16) 5.0 5.5 300.0 5.5 115.6 Example (155) Compound (4-17) 5.5 6.2 300.0 4.8 128.3 Example (156) Compound (4-18) 5.2 6.1 300.0 4.9 144.2 Example (157) Compound (4-19) 5.0 5.6 300.0 5.3 142.5 Example (158) Compound (4-20) 4.6 6.3 300.0 4.8 119.0 Example (159) Compound (4-21) 4.8 5.4 300.0 5.6 117.1 Example (160) Compound (4-22) 4.7 6.3 300.0 4.8 139.8 Example (161) Compound (4-23) 4.7 5.7 300.0 5.3 104.0 Example (162) Compound (4-24) 4.8 6.9 300.0 4.3 130.3 Example (163) Compound (4-25) 4.8 6.8 300.0 4.4 128.1 Example (164) Compound (4-26) 4.9 5.5 300.0 5.5 110.6 Example (165) Compound (4-27) 4.8 7.0 300.0 4.3 137.6 Example (166) Compound (4-28) 4.8 6.0 300.0 5.0 144.3 Example (167) Compound (4-29) 5.4 5.9 300.0 5.1 124.5 Example (168) Compound (4-30) 5.5 5.3 300.0 5.7 129.2 Example (169) Compound (4-31) 5.4 7.0 300.0 4.3 141.3 Example (170) Compound (4-32) 5.0 5.5 300.0 5.4 108.2 Example (171) Compound (4-33) 4.8 5.6 300.0 5.3 90.8 Example (172) Compound (4-34) 5.4 6.6 300.0 4.5 109.3 Example (173) Compound (4-35) 5.5 6.4 300.0 4.7 128.8 Example (174) Compound (4-36) 4.7 5.8 300.0 5.2 145.5 Example (175) Compound (4-37) 5.0 6.1 300.0 4.9 141.1 Example (176) Compound (4-38) 5.0 7.0 300.0 4.3 117.1 Example (177) Compound (4-39) 5.4 6.1 300.0 4.9 108.0 Example (178) The compound (4-40) 4.7 6.8 300.0 4.4 147.6 Example (179) Compound (4-41) 4.7 6.6 300.0 4.6 106.8 Example (180) Compound (4-42) 4.8 6.5 300.0 4.6 95.0 Example (181) Compound (4-43) 5.4 7.1 300.0 4.2 95.6 Example (182) Compound (4-44) 4.7 5.6 300.0 5.3 118.4 Example (183) Compound (4-45) 4.7 5.7 300.0 5.3 131.4 Example (184) Compound (4-46) 5.0 5.6 300.0 5.3 106.1 Example (185) Compound (5-1) 5.5 6.1 300.0 4.9 92.5 Example (186) Compound (5-2) 4.6 6.2 300.0 4.9 130.0 Example (187) Compound (5-3) 4.9 6.9 300.0 4.3 127.2 Example (188) Compound (5-4) 5.3 6.0 300.0 5.0 102.9 Example (189) Compound (5-5) 5.0 5.3 300.0 5.7 99.5 Example (190) Compound (5-6) 4.9 6.9 300.0 4.3 102.0 Example (191) The compound (5-7) 5.2 5.6 300.0 5.4 105.1 Example (192) Compound (5-8) 4.9 5.6 300.0 5.3 114.6 Example (193) Compound (5-9) 5.3 5.3 300.0 5.7 140.1 Example (194) The compound (5-10) 4.9 5.3 300.0 5.6 98.6 Example (195) Compound (5-11) 5.2 5.3 300.0 5.7 100.9 Example (196) The compound (5-12) 4.9 6.6 300.0 4.6 132.5 Example (197) The compound (5-13) 5.3 5.6 300.0 5.3 116.1 Example (198) The compound (5-14) 5.2 5.3 300.0 5.6 94.4 Example (199) The compound (5-15) 5.1 6.9 300.0 4.3 112.8 Example (200) The compound (5-16) 5.4 5.4 300.0 5.5 130.1 Example (201) Compound (5-17) 4.7 5.4 300.0 5.6 134.7 Example (202) Compounds (5-18) 5.4 5.3 300.0 5.6 127.3 Example (203) The compound (5-19) 4.7 5.6 300.0 5.4 92.1 Example (204) The compound (5-20) 5.5 6.5 300.0 4.6 114.7 Example (205) Compound (5-21) 4.9 5.5 300.0 5.4 99.5 Example (206) Compound (5-22) 5.0 5.6 300.0 5.4 123.2 Example (207) Compound (5-23) 5.3 7.0 300.0 4.3 143.5 Example (208) Compounds (5-24) 4.7 6.1 300.0 4.9 128.7 Example (209) Compound (5-25) 4.9 6.7 300.0 4.5 90.7 Example (210) The compound (5-26) 4.7 5.4 300.0 5.6 140.9 Example (211) Compound (5-27) 4.6 6.9 300.0 4.3 135.7 Example (212) Compound (5-28) 5.1 7.1 300.0 4.2 106.1 Example (213) Compound (5-29) 5.4 6.0 300.0 5.0 115.8 Example (214) Compound (5-30) 5.2 6.6 300.0 4.5 114.9 Example (215) Compound (5-31) 5.1 6.5 300.0 4.6 98.6 Example (216) Compound (5-32) 5.1 6.5 300.0 4.6 106.7 Example (217) Compound (5-33) 5.0 5.6 300.0 5.3 142.7 Example (218) Compound (5-34) 5.4 7.0 300.0 4.3 131.5 Example (219) Compound (5-35) 5.3 7.0 300.0 4.3 144.2 Example (220) Compound (5-36) 5.1 5.8 300.0 5.1 130.7 Example (221) Compound (5-37) 5.2 5.5 300.0 5.4 118.2 Example (222) Compound (5-38) 5.3 5.5 300.0 5.4 137.2 Example (223) Compound (5-39) 5.4 6.6 300.0 4.5 121.3 Example (224) Compound (5-40) 5.3 6.5 300.0 4.6 143.2 Example (225) Compound (5-41) 5.0 5.7 300.0 5.3 126.7 Example (226) Compound (5-42) 5.3 6.1 300.0 4.9 93.3 Example (227) Compound (6-1) 5.4 6.2 300.0 4.8 91.4 Example (228) Compound (6-2) 5.3 5.6 300.0 5.3 121.9 Example (229) Compound (6-3) 5.2 6.8 300.0 4.4 131.7 Example (230) Compound (6-4) 4.7 5.4 300.0 5.6 104.9 Example (231) Compound (6-5) 5.3 6.2 300.0 4.9 130.4 Example (232) Compound (6-6) 4.7 6.3 300.0 4.8 98.4 Example (233) Compound (6-7) 5.1 5.9 300.0 5.1 126.1 Example (234) Compound (6-8) 4.7 6.0 300.0 5.0 112.7 Example (235) Compound (6-9) 5.3 5.4 300.0 5.5 145.5 Example (236) The compound (6-10) 5.4 6.6 300.0 4.5 148.4 Example (237) Compound (6-11) 5.4 6.3 300.0 4.8 133.0 Example (238) The compound (6-12) 5.3 6.2 300.0 4.8 137.4 Example (239) Compounds (6-13) 5.3 5.6 300.0 5.3 104.7 Example (240) The compound (6-14) 4.9 6.1 300.0 4.9 128.8 Example (241) The compound (6-15) 4.9 7.1 300.0 4.2 99.4 Example (242) Compounds (6-16) 4.9 5.4 300.0 5.5 118.5 Example (243) Compound (6-17) 4.8 6.9 300.0 4.4 106.1 Example (244) The compound (6-18) 4.8 5.9 300.0 5.1 101.8 Example (245) Compound (6-19) 4.7 6.9 300.0 4.4 119.9 Example (246) Compound (6-20) 4.6 6.0 300.0 5.0 122.4 Example (247) Compound (6-21) 5.5 6.0 300.0 5.0 149.4 Example (248) Compound (6-22) 5.1 5.9 300.0 5.1 134.0 Example (249) Compound (6-23) 4.8 6.3 300.0 4.7 148.4 Example (250) Compound (6-24) 5.2 5.7 300.0 5.3 95.2 Example (251) Compound (6-25) 5.2 6.2 300.0 4.9 95.9 Example (252) Compound (6-26) 4.7 5.9 300.0 5.1 122.5 Example (253) Compound (6-27) 4.6 6.1 300.0 4.9 129.4 Example (254) Compound (6-28) 4.8 6.2 300.0 4.8 129.4 Example (255) Compound (6-29) 5.0 5.3 300.0 5.7 101.3 Example (256) Compound (6-30) 5.2 5.6 300.0 5.4 131.5 Example (257) Compound (6-31) 4.7 5.6 300.0 5.4 121.9 Example (258) Compound (6-32) 4.7 6.1 300.0 4.9 92.1 Example (259) Compound (6-33) 4.6 6.5 300.0 4.6 143.6 Example (260) Compound (6-34) 4.9 6.5 300.0 4.6 117.8 Example (261) Compound (6-35) 5.1 5.5 300.0 5.5 138.9 Example (262) Compound (6-36) 5.2 5.6 300.0 5.4 90.3 Example (263) Compound (6-37) 5.2 6.6 300.0 4.6 115.7 Example (264) Compound (6-38) 5.1 5.9 300.0 5.1 129.8 Example (265) Compound (6-39) 5.0 5.9 300.0 5.1 114.6 Example (266) Compound (6-40) 5.4 5.7 300.0 5.2 138.4 Example (267) Compound (6-41) 5.2 5.8 300.0 5.2 102.3 Example (268) Compound (6-42) 5.3 6.4 300.0 4.7 111.7 Example (269) Compound (6-43) 5.0 5.3 300.0 5.7 104.4 Example (270) Compound (6-44) 4.6 5.4 300.0 5.6 148.4 Example (271) Compound (6-45) 5.2 6.3 300.0 4.7 141.1 Example (272) Compound (6-46) 5.1 6.2 300.0 4.9 126.3

From the results of Table 4, the driving voltage of the organic electroluminescent device fabricated according to Example 8 of the present invention using the compound of the present invention as a hole transporting layer, compared with the organic electroluminescent devices manufactured by Comparative Examples 1, 2, And the luminous efficiency and the life span are remarkably improved.

First, copper phthalocyanine (hereinafter abbreviated as CuPc) was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 40 nm. Then, the compound 3 -27 was vacuum deposited to a thickness of 20 nm to form a hole transport layer. Next, the compound of the present invention was vacuum-deposited on the hole transporting layer to a thickness of 20 nm to form a light emitting auxiliary layer. Then, about the CBP [4,4'-N, N'- dicarbazole-biphenyl] as the phosphorescent host material to the light-emitting auxiliary top layer, a phosphorescent dopant material to the tris (2-phenylpyridine) iridium (hereinafter referred to as Ir (ppy) ₃ ) Was doped to a thickness of 30 nm at a weight ratio of 95: 5 to deposit a light emitting layer. (1, 1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum deposited (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was formed to a thickness of 40 nm as an electron transporting layer, LiF, which is an alkali metal metal to be an electron injecting layer, was deposited to a thickness of 0.2 nm, Subsequently, Al was deposited to a thickness of 150 nm, and Al was used as a cathode to produce an organic electroluminescent device. The reason for using the compound 3-27 of the present invention as the hole transport layer material is that the driving voltage of the organic electronic device to which the compound 3-27 is applied is low and the lifetime is high while the light emitting efficiency is high to be.

[Comparative Example 4]

An organic electroluminescent device was fabricated in the same manner as in Example 9 except that the light emitting auxiliary layer was omitted. That is, an organic electroluminescent device was fabricated in the same manner as in Example 9, except that no light-emission-assisting layer was formed.

[Comparative Example 5]

An organic electroluminescent device was fabricated in the same manner as in Example 9, except that the compound of the present invention was used instead of the compound of the present invention to form a light-emitting auxiliary layer.

A forward bias DC voltage was applied to the organic electroluminescent devices of Example 9, Comparative Example 4 and Comparative Example 5 of the present invention, and electroluminescence (EL) characteristics were measured with photoresearch PR-650 And the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 300 cd / m 2. The results of measurement of the driving voltage, current density, luminance, luminescence efficiency and lifetime of the organic electroluminescent device manufactured according to Example 9, Comparative Example 4 and Comparative Example 5 were as shown in Table 5 below.

compound Driving voltage electric current
(mA / cm 2) Luminance
(cd / m &lt; 2 & efficiency
(cd / A) T (95) Comparative Example (4) Not used 4.8 5.1 300.0 5.1 103.4 Comparative Example (5) Comparative Example (3) 4.7 6.1 300.0 4.9 72.4 Example (273) Compound (1-1) 4.6 5.9 300.0 5.1 115.9 Example (274) The compound (1-2) 4.4 5.7 300.0 5.2 117.0 Example (275) The compound (1-3) 4.5 5.3 300.0 5.7 143.0 Example (276) The compound (1-4) 4.6 5.9 300.0 5.1 119.3 Example (277) Compound (1-5) 4.6 5.9 300.0 5.1 120.8 Example (278) The compound (1-6) 4.5 5.2 300.0 5.7 123.2 Example (279) Compound (1-7) 4.3 5.4 300.0 5.5 145.6 Example (280) Compound (1-8) 4.5 5.7 300.0 5.2 143.9 Example (281) Compound (1-9) 4.5 5.6 300.0 5.4 143.2 Example (282) The compound (1-10) 4.5 5.3 300.0 5.7 138.2 Example (283) The compound (1-11) 4.3 5.4 300.0 5.5 140.1 Example (284) The compound (1-12) 4.5 5.5 300.0 5.4 135.4 Example (285) The compound (1-13) 4.3 5.6 300.0 5.4 117.5 Example (286) The compound (1-14) 4.4 5.4 300.0 5.5 147.7 Example (287) The compound (1-15) 4.4 5.6 300.0 5.4 145.9 Example (288) The compound (1-16) 4.6 5.5 300.0 5.4 131.3 Example (289) The compound (1-17) 4.3 5.6 300.0 5.3 130.6 Example (290) Compound (1-18) 4.5 5.8 300.0 5.2 134.3 Example (291) The compound (1-19) 4.5 5.3 300.0 5.7 116.7 Example (292) Compound (1-20) 4.6 5.9 300.0 5.1 140.9 Example (293) Compound (1-21) 4.5 5.3 300.0 5.7 115.9 Example (294) The compound (1-22) 4.6 5.8 300.0 5.2 126.4 Example (295) Compound (1-23) 4.2 5.5 300.0 5.4 133.8 Example (296) Compound (1-24) 4.6 5.2 300.0 5.7 135.5 Example (297) The compound (1-25) 4.3 5.8 300.0 5.2 146.4 Example (298) Compound (1-26) 4.6 5.5 300.0 5.4 116.4 Example (299) Compound (1-27) 4.5 5.5 300.0 5.5 119.7 Example (300) Compound (1-28) 4.7 5.7 300.0 5.2 142.6 Example (301) Compound (1-29) 4.6 5.6 300.0 5.3 130.7 Example (302) Compound (1-30) 4.4 5.4 300.0 5.6 133.5 Example (303) Compound (1-31) 4.4 5.8 300.0 5.2 124.5 Example (304) Compound (1-32) 4.7 5.7 300.0 5.2 132.0 Example (305) Compound (1-33) 4.3 5.3 300.0 5.6 117.3 Example (306) Compound (1-34) 4.3 5.6 300.0 5.4 139.8 Example (307) Compound (1-35) 4.3 5.4 300.0 5.5 142.8 Example (308) Compound (1-36) 4.5 5.7 300.0 5.2 148.8 Example (309) Compound (1-37) 4.4 5.9 300.0 5.1 132.3 Example (310) Compound (1-38) 4.4 5.5 300.0 5.4 129.4 Example (311) Compound (1-39) 4.5 5.5 300.0 5.5 141.4 Example (312) Compound (1-40) 4.3 5.9 300.0 5.1 137.4 Example (313) Compound (1-41) 4.7 5.9 300.0 5.1 135.5 Example (314) Compound (1-42) 4.7 5.3 300.0 5.7 143.9 Example (315) Compound (1-43) 4.2 5.7 300.0 5.3 139.9 Example (316) Compound (1-44) 4.4 5.8 300.0 5.2 145.1 Example (317) Compound (1-45) 4.5 5.3 300.0 5.7 117.8 Example (318) Compound (1-46) 4.2 5.8 300.0 5.1 132.7 Example (319) Compound (2-1) 4.3 5.4 300.0 5.6 127.4 Example (320) Compound (2-2) 4.3 5.7 300.0 5.2 142.8 Example (321) Compound (2-3) 4.3 5.2 300.0 5.7 116.7 Example (322) Compound (2-4) 4.4 5.5 300.0 5.4 116.0 Example (323) Compound (2-5) 4.4 6.0 300.0 5.0 126.3 Example (324) Compound (2-6) 4.5 5.3 300.0 5.6 126.6 Example (325) Compound (2-7) 4.3 5.7 300.0 5.3 118.0 Example (326) Compound (2-8) 4.3 6.0 300.0 5.0 136.3 Example (327) Compound (2-9) 4.5 5.4 300.0 5.6 118.5 Example (328) Compound (2-10) 4.4 5.9 300.0 5.1 148.3 Example (329) Compound (2-11) 4.5 5.2 300.0 5.7 130.2 Example (330) The compound (2-12) 4.4 5.5 300.0 5.5 149.6 Example (331) The compound (2-13) 4.3 5.6 300.0 5.3 140.8 Example (332) The compound (2-14) 4.3 5.3 300.0 5.7 117.0 Example (333) Compound (2-15) 4.5 5.3 300.0 5.7 124.8 Example (334) The compound (2-16) 4.5 5.3 300.0 5.6 120.9 Example (335) Compound (2-17) 4.5 5.8 300.0 5.1 119.9 Example (336) Compound (2-18) 4.3 5.7 300.0 5.2 139.3 Example (337) Compound (2-19) 4.4 6.0 300.0 5.0 145.9 Example (338) Compound (2-20) 4.5 5.9 300.0 5.0 144.9 Example (339) Compound (2-21) 4.3 5.4 300.0 5.5 146.8 Example (340) Compound (2-22) 4.5 5.4 300.0 5.6 137.9 Example (341) The compound (2-23) 4.2 5.7 300.0 5.3 146.0 Example (342) Compound (2-24) 4.3 5.8 300.0 5.1 134.9 Example (343) Compound (2-25) 4.7 5.6 300.0 5.4 119.7 Example (344) Compound (2-26) 4.2 5.5 300.0 5.4 120.7 Example (345) Compound (2-27) 4.5 5.6 300.0 5.4 146.2 Example (346) Compound (2-28) 4.5 5.7 300.0 5.2 132.6 Example (347) Compound (2-29) 4.3 5.6 300.0 5.4 133.8 Example (348) Compound (2-30) 4.3 6.0 300.0 5.0 133.4 Example (349) Compound (2-31) 4.6 5.3 300.0 5.7 139.3 Example (350) Compound (2-32) 4.3 5.3 300.0 5.6 141.2 Example (351) Compound (2-33) 4.7 5.8 300.0 5.2 122.2 Example (352) Compound (2-34) 4.7 5.5 300.0 5.4 117.5 Example (353) Compound (2-35) 4.2 5.3 300.0 5.7 145.4 Example (354) Compound (2-36) 4.4 5.8 300.0 5.2 148.2 Example (355) Compound (2-37) 4.5 5.6 300.0 5.4 139.7 Example (356) Compound (2-38) 4.7 5.6 300.0 5.3 139.6 Example (357) Compound (2-39) 4.4 5.9 300.0 5.1 117.1 Example (358) Compound (2-40) 4.5 5.4 300.0 5.5 147.1 Example (359) Compound (2-41) 4.6 5.6 300.0 5.3 121.5 Example (360) Compound (2-42) 4.6 5.4 300.0 5.6 149.5 Example (361) Compound (2-43) 4.3 5.8 300.0 5.2 117.4 Example (362) Compound (2-44) 4.4 5.6 300.0 5.3 133.2 Example (363) Compound (2-45) 4.7 5.8 300.0 5.2 120.7 Example (364) Compound (2-46) 4.4 5.5 300.0 5.4 139.5 Example (365) Compound (3-1) 4.5 5.4 300.0 5.6 123.9 Example (366) The compound (3-2) 4.5 5.8 300.0 5.2 141.4 Example (367) Compound (3-3) 4.4 5.7 300.0 5.2 116.3 Example (368) Compound (3-4) 4.6 5.5 300.0 5.5 147.6 Example (369) Compound (3-5) 4.3 5.4 300.0 5.6 132.0 Example (370) Compound (3-6) 4.5 5.6 300.0 5.3 147.8 Example (371) Compound (3-7) 4.2 6.0 300.0 5.0 136.5 Example (372) Compound (3-8) 4.7 5.4 300.0 5.6 129.9 Example (373) Compound (3-9) 4.7 6.0 300.0 5.0 131.6 Example (374) Compound (3-10) 4.6 5.4 300.0 5.5 130.9 Example (375) The compound (3-11) 4.5 6.0 300.0 5.0 122.4 Example (376) The compound (3-12) 4.3 5.4 300.0 5.5 129.9 Example (377) The compound (3-13) 4.4 5.5 300.0 5.5 127.9 Example (378) The compound (3-14) 4.6 5.8 300.0 5.2 124.2 Example (379) The compound (3-15) 4.5 5.2 300.0 5.7 124.0 Example (380) The compound (3-16) 4.5 5.7 300.0 5.3 119.1 Example (381) Compound (3-17) 4.4 5.5 300.0 5.5 131.6 Example (382) Compound (3-18) 4.4 5.4 300.0 5.6 131.0 Example (383) Compound (3-19) 4.6 5.5 300.0 5.4 140.4 Example (384) Compound (3-20) 4.7 5.7 300.0 5.2 137.8 Example (385) Compound (3-21) 4.3 5.8 300.0 5.2 134.9 Example (386) Compound (3-22) 4.6 5.8 300.0 5.2 135.6 Example (387) Compound (3-23) 4.7 5.8 300.0 5.2 123.7 Example (388) Compound (3-24) 4.5 5.6 300.0 5.3 130.6 Example (389) Compound (3-25) 4.6 5.6 300.0 5.3 131.3 Example (390) Compound (3-26) 4.6 5.4 300.0 5.6 132.3 Example (391) Compound (3-27) 4.3 5.6 300.0 5.4 149.6 Example (392) Compound (3-28) 4.6 5.9 300.0 5.0 121.3 Example (393) Compound (3-29) 4.4 5.4 300.0 5.5 115.9 Example (394) Compound (3-30) 4.2 5.3 300.0 5.7 139.3 Example (395) Compound (3-31) 4.3 5.4 300.0 5.5 130.4 Example (396) Compound (3-32) 4.5 5.9 300.0 5.1 119.7 Example (397) Compound (3-33) 4.6 5.4 300.0 5.6 120.2 Example (398) Compound (3-34) 4.6 5.4 300.0 5.6 138.5 Example (399) Compound (3-35) 4.3 5.6 300.0 5.4 118.2 Example (400) Compound (3-36) 4.6 5.9 300.0 5.0 144.8 Example (401) Compound (3-37) 4.4 5.8 300.0 5.2 129.4 Example (402) Compound (3-38) 4.5 5.4 300.0 5.5 126.5 Example (403) Compound (3-39) 4.5 5.9 300.0 5.1 147.6 Example (404) Compound (3-40) 4.6 5.4 300.0 5.5 117.6 Example (405) Compound (3-41) 4.3 5.5 300.0 5.5 130.1 Example (406) Compound (3-42) 4.5 6.0 300.0 5.0 147.4 Example (407) Compound (3-43) 4.4 5.8 300.0 5.2 118.0 Example (408) Compound (3-44) 4.2 5.9 300.0 5.1 145.0 Example (409) Compound (3-45) 4.5 5.7 300.0 5.2 149.2 Example (410) Compound (3-46) 4.2 5.4 300.0 5.6 144.7 Example (411) Compound (4-1) 4.5 5.9 300.0 5.1 149.0 Example (412) Compound (4-2) 4.4 5.9 300.0 5.1 120.7 Example (413) Compound (4-3) 4.5 5.7 300.0 5.3 146.1 Example (414) The compound (4-4) 4.2 5.6 300.0 5.4 125.0 Example (415) Compound (4-5) 4.3 5.9 300.0 5.1 143.4 Example (416) Compound (4-6) 4.2 5.8 300.0 5.2 118.9 Example (417) The compound (4-7) 4.2 5.7 300.0 5.3 147.9 Example (418) Compound (4-8) 4.7 5.5 300.0 5.5 125.7 Example (419) Compound (4-9) 4.4 5.8 300.0 5.2 121.1 Example (420) Compound (4-10) 4.5 5.5 300.0 5.4 129.9 Example (421) The compound (4-11) 4.2 5.8 300.0 5.2 146.6 Example (422) The compound (4-12) 4.6 5.7 300.0 5.3 125.8 Example (423) The compound (4-13) 4.5 5.3 300.0 5.6 129.4 Example (424) The compound (4-14) 4.4 5.4 300.0 5.6 145.3 Example (425) Compound (4-15) 4.6 5.8 300.0 5.2 142.5 Example (426) The compound (4-16) 4.4 5.3 300.0 5.7 137.5 Example (427) Compound (4-17) 4.3 5.6 300.0 5.4 142.3 Example (428) Compound (4-18) 4.5 5.3 300.0 5.6 139.0 Example (429) Compound (4-19) 4.2 5.9 300.0 5.1 123.6 Example (430) Compound (4-20) 4.5 6.0 300.0 5.0 125.4 Example (431) Compound (4-21) 4.4 5.8 300.0 5.2 129.0 Example (432) Compound (4-22) 4.3 5.6 300.0 5.3 149.7 Example (433) Compound (4-23) 4.5 5.4 300.0 5.5 130.3 Example (434) Compound (4-24) 4.4 5.7 300.0 5.3 142.4 Example (435) Compound (4-25) 4.4 5.2 300.0 5.7 146.3 Example (436) Compound (4-26) 4.3 5.4 300.0 5.5 134.2 Example (437) Compound (4-27) 4.4 5.5 300.0 5.5 129.2 Example (438) Compound (4-28) 4.7 5.8 300.0 5.2 139.0 Example (439) Compound (4-29) 4.5 5.7 300.0 5.2 138.5 Example (440) Compound (4-30) 4.3 5.7 300.0 5.3 135.2 Example (441) Compound (4-31) 4.4 5.4 300.0 5.5 144.5 Example (442) Compound (4-32) 4.6 5.6 300.0 5.3 146.0 Example (443) Compound (4-33) 4.5 5.5 300.0 5.5 119.0 Example (444) Compound (4-34) 4.6 5.8 300.0 5.2 128.4 Example (445) Compound (4-35) 4.6 5.6 300.0 5.3 136.2 Example (446) Compound (4-36) 4.6 5.3 300.0 5.6 145.1 Example (447) Compound (4-37) 4.3 5.9 300.0 5.1 125.4 Example (448) Compound (4-38) 4.4 5.7 300.0 5.3 141.7 Example (449) Compound (4-39) 4.2 5.6 300.0 5.3 129.7 Example (450) The compound (4-40) 4.3 5.3 300.0 5.7 124.9 Example (451) Compound (4-41) 4.6 5.6 300.0 5.3 117.0 Example (452) Compound (4-42) 4.7 5.8 300.0 5.2 131.4 Example (453) Compound (4-43) 4.2 5.4 300.0 5.6 137.6 Example (454) Compound (4-44) 4.3 5.4 300.0 5.5 133.3 Example (455) Compound (4-45) 4.3 5.9 300.0 5.1 147.9 Example (456) Compound (4-46) 4.4 5.7 300.0 5.3 121.7 Example (457) Compound (5-1) 4.7 5.4 300.0 5.6 128.4 Example (458) Compound (5-2) 4.4 5.3 300.0 5.7 125.1 Example (459) Compound (5-3) 4.5 5.8 300.0 5.2 116.4 Example (460) Compound (5-4) 4.4 5.8 300.0 5.2 126.5 Example (461) Compound (5-5) 4.6 5.5 300.0 5.4 137.3 Example (462) Compound (5-6) 4.5 5.7 300.0 5.2 129.5 Example (463) The compound (5-7) 4.2 5.5 300.0 5.4 145.5 Example (464) Compound (5-8) 4.6 5.6 300.0 5.4 121.8 Example (465) Compound (5-9) 4.5 5.2 300.0 5.7 128.0 Example (466) The compound (5-10) 4.2 5.3 300.0 5.7 122.2 Example (467) Compound (5-11) 4.7 5.6 300.0 5.4 142.3 Example (468) The compound (5-12) 4.4 5.4 300.0 5.6 127.5 Example (469) The compound (5-13) 4.6 5.6 300.0 5.4 149.5 Example (470) The compound (5-14) 4.2 5.4 300.0 5.5 116.3 Example (471) The compound (5-15) 4.3 5.4 300.0 5.6 136.1 Example (472) The compound (5-16) 4.3 5.5 300.0 5.5 135.6 Example (473) Compound (5-17) 4.4 5.7 300.0 5.2 148.8 Example (474) Compounds (5-18) 4.4 5.3 300.0 5.7 147.9 Example (475) The compound (5-19) 4.5 5.8 300.0 5.2 139.2 Example (476) The compound (5-20) 4.4 5.6 300.0 5.4 144.1 Example (477) Compound (5-21) 4.7 5.5 300.0 5.4 116.1 Example (478) Compound (5-22) 4.5 5.7 300.0 5.3 140.1 Example (479) Compound (5-23) 4.2 5.7 300.0 5.3 137.3 Example (480) Compounds (5-24) 4.4 5.8 300.0 5.2 132.4 Example (481) Compound (5-25) 4.3 5.5 300.0 5.5 126.1 Example (482) The compound (5-26) 4.2 5.2 300.0 5.7 116.4 Example (483) Compound (5-27) 4.4 5.9 300.0 5.1 129.1 Example (484) Compound (5-28) 4.4 5.6 300.0 5.3 118.3 Example (485) Compound (5-29) 4.5 5.7 300.0 5.2 133.2 Example (486) Compound (5-30) 4.7 5.7 300.0 5.3 118.8 Example (487) Compound (5-31) 4.2 5.3 300.0 5.7 149.4 Example (488) Compound (5-32) 4.4 5.6 300.0 5.3 127.0 Example (489) Compound (5-33) 4.4 5.3 300.0 5.7 140.2 Example (490) Compound (5-34) 4.7 5.7 300.0 5.2 128.9 Example (491) Compound (5-35) 4.4 5.6 300.0 5.4 144.9 Example (492) Compound (5-36) 4.5 5.6 300.0 5.3 144.2 Example (493) Compound (5-37) 4.4 5.6 300.0 5.4 137.8 Example (494) Compound (5-38) 4.6 5.8 300.0 5.2 145.5 Example (495) Compound (5-39) 4.6 5.6 300.0 5.4 141.7 Example (496) Compound (5-40) 4.6 5.3 300.0 5.7 145.3 Example (497) Compound (5-41) 4.4 5.8 300.0 5.2 127.2 Example (498) Compound (5-42) 4.5 5.7 300.0 5.2 119.1 Example (499) Compound (6-1) 4.4 5.5 300.0 5.4 131.3 Example (500) Compound (6-2) 4.3 5.5 300.0 5.5 136.4 Example (501) Compound (6-3) 4.6 5.4 300.0 5.6 135.3 Example (502) Compound (6-4) 4.3 6.0 300.0 5.0 119.9 Example (503) Compound (6-5) 4.5 5.7 300.0 5.2 140.3 Example (504) Compound (6-6) 4.3 5.8 300.0 5.1 128.1 Example (505) Compound (6-7) 4.4 5.3 300.0 5.7 147.9 Example (506) Compound (6-8) 4.7 5.5 300.0 5.4 139.4 Example (507) Compound (6-9) 4.6 5.3 300.0 5.6 115.1 Example (508) The compound (6-10) 4.5 6.0 300.0 5.0 135.1 Example (509) Compound (6-11) 4.7 5.9 300.0 5.1 145.4 Example (510) The compound (6-12) 4.6 5.6 300.0 5.4 130.8 Example (511) Compounds (6-13) 4.5 5.4 300.0 5.5 142.3 Example (512) The compound (6-14) 4.5 5.5 300.0 5.4 141.0 Example (513) The compound (6-15) 4.6 5.6 300.0 5.4 149.3 Example (514) Compounds (6-16) 4.3 5.3 300.0 5.7 144.2 Example (515) Compound (6-17) 4.6 5.6 300.0 5.4 137.7 Example (516) The compound (6-18) 4.7 5.3 300.0 5.7 147.3 Example (517) Compound (6-19) 4.5 5.4 300.0 5.6 134.6 Example (518) Compound (6-20) 4.4 5.9 300.0 5.1 137.8 Example (519) Compound (6-21) 4.4 6.0 300.0 5.0 126.7 Example (520) Compound (6-22) 4.5 5.7 300.0 5.3 116.3 Example (521) Compound (6-23) 4.5 5.7 300.0 5.3 134.9 Example (522) Compound (6-24) 4.4 5.8 300.0 5.1 121.3 Example (523) Compound (6-25) 4.3 5.3 300.0 5.6 145.2 Example (524) Compound (6-26) 4.7 5.9 300.0 5.1 117.8 Example (525) Compound (6-27) 4.7 5.7 300.0 5.2 119.5 Example (526) Compound (6-28) 4.6 5.9 300.0 5.1 120.5 Example (527) Compound (6-29) 4.3 5.5 300.0 5.5 124.5 Example (528) Compound (6-30) 4.5 6.0 300.0 5.0 127.5 Example (529) Compound (6-31) 4.3 5.7 300.0 5.2 143.1 Example (530) Compound (6-32) 4.4 5.5 300.0 5.4 141.1 Example (531) Compound (6-33) 4.5 5.3 300.0 5.7 140.0 Example (532) Compound (6-34) 4.7 5.8 300.0 5.2 150.0 Example (533) Compound (6-35) 4.6 5.6 300.0 5.4 148.9 Example (534) Compound (6-36) 4.6 5.3 300.0 5.7 132.2 Example (535) Compound (6-37) 4.6 5.8 300.0 5.2 120.7 Example (536) Compound (6-38) 4.4 5.5 300.0 5.4 120.3 Example (537) Compound (6-39) 4.4 5.5 300.0 5.4 116.1 Example (538) Compound (6-40) 4.7 5.7 300.0 5.2 131.6 Example (539) Compound (6-41) 4.2 5.8 300.0 5.2 126.6 Example (540) Compound (6-42) 4.3 5.7 300.0 5.3 119.4 Example (541) Compound (6-43) 4.6 5.8 300.0 5.1 146.2 Example (542) Compound (6-44) 4.7 5.8 300.0 5.1 116.9 Example (543) Compound (6-45) 4.6 5.3 300.0 5.7 132.4 Example (544) Compound (6-46) 4.4 5.8 300.0 5.2 120.8

As can be seen from the results of Table 5, when the compound according to the present invention was used as the luminescent auxiliary layer, Comparative Example 4 and Comparative Compound 3 in which the luminescent auxiliary layer was not used at all, The driving voltage of the organic electroluminescent device can be lowered and the efficiency and lifetime can be remarkably improved.

The compound according to the present invention can be applied not only to organic electroluminescent devices (OLEDs) but also to display devices, organic solar cells, organic photoconductors (OPC), organic transistors (organic TFT), monochromatic or white illumination devices Can also be used.

Meanwhile, the same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a hole injecting layer, a light emitting layer, an electron injecting layer and an electron transporting layer.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, many variations and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

Claims (8)

A compound represented by the following formula (1).
&Lt; Formula 1 >

In Formula 1,
(1) Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, tritium, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₆₀ arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ aryl group and C ₂ ~ C with a substituent selected from the ₆₀ group consisting of a heterocyclic group of the substituted or unsubstituted C ₆ ~ C ₆₀ substituted by deuterium aryl group ; Hydrogen, deuterium, tritium, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₆₀ aryl amine group, a C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group and C ₂ ~ of A substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with a substituent selected from the group consisting of C ₆₀ heterocyclic groups and contains at least one hetero atom selected from the group consisting of O, N, S, P and Si; Hydrogen, deuterium, tritium, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group and C ₂ ~ C ₆₀ heterocyclic group selected from the group consisting of A C ₆ ~ C ₃₀ aryloxy group substituted or unsubstituted with a substituent group; C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, and a hetero group, ring C ₂ ~ C ₆₀ of a substituent is substituted or unsubstituted in A C ₁ to C ₅₀ alkyl group; And a silane group substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₆₀ aryl group and a C ₆ to C ₆₀ aryl group substituted with deuterium,
(2) R ₁ to R ₁₂ are each independently of the other hydrogen; heavy hydrogen; Tritium; Substituted with hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₅ ~ C ₆₀ aryl amine group, a C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the an aryl group of C ₆ ~ C ₆₀ aryl group and a substituted or non-substituted substituted or unsubstituted with substituents selected from the group consisting of a heterocycle of the C ₂ ~ C ₆₀ unsubstituted C ₆ ~ C _60; C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, and a hetero group, ring C ₂ ~ C ₆₀ of a substituent is substituted or unsubstituted in A C ₁ to C ₅₀ alkyl group; Wherein R is selected from the group consisting of hydrogen, deuterium, tritium, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₂₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, and a C ₂ to C ₆₀ heterocyclic group A C ₂ to C ₄₀ alkenyl group substituted or unsubstituted with a substituent group; Hydrogen, deuterium, tritium, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group and C ₂ ~ C ₆₀ heterocyclic group selected from the group consisting of A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group; Hydrogen, deuterium, tritium, C ₁ ~ C ₆₀ alkyl group, C ₆ ~ C ₆₀ aryl amine group, a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₆₀ substituted with a heavy hydrogen of the aryl group and a substituted or unsubstituted a heterocyclic group of C ₂ ~ C hwandoen with a substituent selected from the ₆₀ group consisting of heterocyclic ring being unsubstituted or substituted with O, N, S, P, and C ₂ ~ containing at least one hetero atom of the Si C _60; A condensed ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An amine group substituted or unsubstituted with a substituent selected from the group consisting of a C ₁ to C ₆₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heterocyclic group; A nitro group; A nitrile group; Amide group; And a silane group; , &Lt; / RTI &gt;
(3) R ₄ and R ₅ , R ₆ and R ₇ , R ₉ and R ₁₀ , R ₁₀ and R ₁₁ , and R ₁₁ and R ₁₂ each may be bonded to adjacent groups to form a saturated or unsaturated ring, At least one group of R ₄ and R ₅ , R ₆ and R ₇ , R ₉ and R ₁₀ , R ₁₀ and R ₁₁ , and at least one of R ₁₁ and R ₁₂ necessarily forms the ring. The method according to claim 1,
Is a compound represented by any one of the following formulas (2) to (6).

Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

An organic electroluminescent device comprising a first electrode sequentially laminated, at least one organic layer containing a compound of any one of claims 1 to 3, and a second electrode. 5. The method of claim 4,
Wherein said compound is formed into said organic material layer by a solution process. 5. The method of claim 4,
Wherein the organic material layer includes at least one of a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, a hole injecting layer, an electron injecting layer, and an electron transporting layer. A display device including the organic electroluminescent device of claim 4; And
A controller for driving the display device; &Lt; / RTI &gt; 8. The method of claim 7,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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