KR101896035B1 - Novel compound for organic electronic element, organic electronic element using the same, and terminal thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and lifetime of the device, and an organic electric device using the same and a terminal thereof.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an organic electroluminescent device using the same. BACKGROUND OF THE INVENTION [0002]

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

Mr. Eastman Kodak of the 1980s. W. CW Tang et al. Have made organic electroluminescent devices using organic materials practical by developing a laminated structure device in which various roles are shared among various materials. In order to obtain a high luminance of more than 1000 cd / m ^{2 at} a voltage of 10 V or lower by laminating a phosphor capable of transporting electrons and an organic material capable of transporting holes and injecting both charges into the phosphor layer Respectively.

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. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

Particularly, various studies have been conducted on organic materials inserted into a hole transporting layer or a buffer layer for an excellent lifetime characteristic of an organic electric device. To this end, a high hole transporting property from an anode to an organic layer is given, A hole injection layer material having high uniformity and low crystallinity is required.

It is possible to delay penetration and diffusion of the metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, and to stabilize the joule heating caused by driving the device, Lt; RTI ID = 0.0 > layer < / RTI > 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.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

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 novel compound capable of improving the light emitting efficiency, the low driving voltage, the color purity, and the lifetime of the device, and an organic electric device using the same and a terminal thereof.

The present invention provides a compound having indolocarbazole as a core, which is useful as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, a light emitting material and / or a passivation (keping) Emitting material, a host, a dopant, a hole injecting layer, and a hole transporting layer.

More particularly, the present invention relates to a compound represented by the following formula (1) for solving the above problems of the prior art and achieving the object of the present invention of improving the luminous efficiency, the driving voltage, the color purity, to provide.

In Formula 1,

₁₎ Ar 1 is selected from hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of the alkyl amine group, C ₁ ~ C alkyl thiophene group of _20, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of, C ₆ ~ C ₆₀ A C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group A C ₆ -C ₆₀ aryl group unsubstituted or substituted with one or more substituents; A halogen atom, 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 ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, N, S, at least one substituted or unsubstituted heteroaryl group of C ₅ ~ C ₆₀ having a one; 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ -C ₃₀ aryloxy group; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ 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 to be.

2) L ₁ or L ₂ are the same or different and each is substituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and amino group Or an unsubstituted C ₆ to C ₆₀ arylene group; A heteroaryl group of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₅ ~ C ₆₀ of; And a substituted or unsubstituted divalent aliphatic hydrocarbon.

More specifically, the present invention provides a compound represented by any one of the compounds represented by the general formulas (1) to (6). Wherein Ar ₁ and L ₂ are the same as defined in the above formula (1).

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

The term " halo " or " halogen ", as used herein, unless otherwise indicated, includes fluorine, chlorine, bromine, and iodine.

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.

The term " heteroalkyl ", as used herein, unless otherwise indicated, means alkyl having one or more heteroatoms.

As used herein, the term " heteroaryl group " or " heteroarylene group " means an aryl or arylene group of 3 to 60 carbon atoms having one or more heteroatoms, respectively, It is not.

The term " heterocycloalkyl ", " heterocyclic group ", as used herein, unless otherwise stated, includes one or more heteroatoms and has from 2 to 60 carbon atoms.

As used herein, the term " heteroatom " means N, O, S, P and Si, unless otherwise stated.

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.

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 halogen atom, a germanium group, and a C ₅ to C ₂₀ heterocyclic group.

More specifically, the compounds represented by the above formulas (1) to (6) are represented by the following compounds, but are not limited thereto.

The compounds represented by Formula 1 may be one of the compounds shown in Formula 7, but are not limited thereto. Here, the substituents of the compound represented by the formula (1) are broadly related, and it is practically difficult to exemplify all the compounds. Therefore, representative compounds are exemplarily described, but the compounds represented by the formula (1) You can configure some.

By using the novel compounds according to the present invention, it is possible to remarkably improve the luminous efficiency, the driving voltage, the color purity, and the lifetime of the device.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

The compounds according to the invention having the above formula can be used in a soluble process. In other words, the above-mentioned combination can form an organic layer of an organic electronic device to be described later by a solution process. That is, when the compound is used as an organic material layer, the organic material layer may be formed by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Lt; RTI ID = 0.0 > a < / RTI > fewer layers.

Hereinafter, some embodiments of the present invention will be described in detail with reference to exemplary 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 symbols as possible even if 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."

Example

Hereinafter, the present invention will be described in more detail with reference to Production Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example

Hereinafter, preparation examples or synthesis examples of the compounds belonging to the formula 1 will be described. However, since the number of the compounds belonging to the formula (1) is large, some of the compounds belonging to the formula (1) will be exemplarily explained. Those skilled in the art, that is, those skilled in the art, can prepare the compounds belonging to the present invention which are not illustrated through the following production examples.

General synthesis method

The synthesis of the compound was carried out as follows.

Example  One) Sub  1 Synthetic method example:

Sub  1-2 Synthetic method

Pd ₂ (dba) ₃ (8.24 g, 9 mmol), PPh ₃ (7.87 g, 30 mmol) was added to a mixture of carbazole (50.2 g, 300 mmol) and bromobenzene (56.5 g, NaOt-Bu (86.5 g, 900 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. The organic layer was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 48.66 g (67%) of Sub1-1. Sub 1-1 (48.66 g, 200 mmol) was dissolved in 600 mL of methylene chloride, 0.05 equivalents of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) Stir for a time. After completion of the reaction, 300 mL of 5% HCl is added, and 300 mL of water is added. The remaining NBS is removed, and the mixture is extracted with ether and water. The organic layer is dried over MgSO ₄ and concentrated. Subsequently, the resulting organic material was purified by silicagel column and recrystallized to obtain 47.7 g (74%) of Sub 1-2.

Sub  1-5 Synthetic methods

4-bromo-1-iodo-2-nitrobenzene (227 g, 690 mmol) was added to a ₂ L round bottom flask with the addition of phenylboronic acid (76.61 g, 628 mmol), THF (700 mL) and H ₂ O NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction was allowed to proceed at 80 ° C for 24 hours. When the reaction is completed, the reaction mixture is extracted with methylene chloride, water, and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column (methylene chloride: hexane = 1: 3) to obtain 80.4 g (46%) Sub 1-3. Triethylphosphate is added to the obtained 1-3, and the mixture is refluxed at 160 ° C to 165 ° C for 14 hours. After the reaction is completed, the remaining triethylphosphite is removed by distillation under reduced pressure, diluted with a mixed solvent of MeOH: H ₂ O = 1: 1, and the resulting solid is filtered. The resulting solid is washed with a mixed solvent of MeOH: H ₂ O = 1: 1 and petroleum ether. The solid is dissolved in methylene chloride, dried over MgSO ₄ , concentrated and silicagel column to obtain Sub 1-4. (petroleum ether: methylene chloride = 2: 1)

Pd ₂ (dba) ₃ (8.24 g, 9 mmol) and PPh ₃ (7.87 g, 30 mmol) were added to a mixture of Sub 1-4 (80.4 g, 327 mmol) and bromobenzene (56.5 g, And NaO t- Bu (86.5 g, 900 mmol) were added thereto, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 48.66 g (46%) of Sub 1-5.

Example  One) Sub  2 Synthetic method example:

Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.), Toluene (1 eq.), 10.5 mL / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain product Sub 2.

Examples of Sub 2 include, but are not limited to:

L ₁ and L ₂ are each independently a divalent functional group such as phenylene, biphenylene, naphthylene, pyridinylene, pyrimidinylene, pyrazinylene, piperidineylene, piperazinylene, pyrrolidenylene, And the like, but is not limited thereto.

compound FD-MS compound FD-MS Sub 2-1 _{m / z = 454.19 (C 30} H 23 BN 2 O 2 = 454.33) Sub 2-2 _{m / z = 504.20 (C 34} H 25 BN 2 O 2 = 504.39) Sub 2-3 _{m / z = 504.20 (C 34} H 25 BN 2 O 2 = 504.39) Sub 2-4 _{m / z = 530.22 (C 36} H 27 BN 2 O 2 = 530.42) Sub 2-5 m / z = 586.19 (C ₃₈ H ₂₇ BN ₂ O ₂ S = 586.51) Sub 2-6 m / z = 610.19 (C ₄₀ H ₂₇ BN ₂ O ₂ S = 610.53) Sub 2-7 _{m / z = 534.21 (C 35} H 27 BN 2 O 3 = 534.41) Sub 2-8 _{m / z = 522.19 (C 34} H 24 BFN 2 O 2 = 522.38) Sub 2-9 _{m / z = 530.22 (C 36} H 27 BN 2 O 2 = 530.42) Sub 2-10 _{m / z = 510.25 (C 34} H 31 BN 2 O 2 = 510.43) Sub 2-11 m / z = 554.22 (C ₃₈ H ₂₇ BN ₂ O ₂ = 554.44) Sub 2-12 m / z = 606.25 (C ₄₂ H ₃₁ BN ₂ O ₂ = 606.52) Sub 2-13 m / z = 580.23 (C ₄₀ H ₂₉ BN ₂ O ₂ = 580.48)

Example  3) Example of synthesis of final compound:

Sub 1 compound (1.1 eq.), Pd (PPh ₃ ) ₄ (1 eq.), Or a compound of 3-bromo-9-phenyl-9H- (0.03-0.05 eq.), NaOH (3 eq.), THF (3 mL / 1 mmol) and water (1.5 mL / 1 mmol).

Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature. The mixture was extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain the product.

compound FD-MS compound FD-MS 2-1 m / z = 651.27 (C ₄₈ H ₃₃ N ₃ = 651.80) 2-2 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 2-3 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 2-4 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.89) 2-5 m / z = 733.26 (C ₅₂ H ₃₅ N ₃ S = 733.92) 2-6 m / z = 757.26 (C ₅₄ H ₃₅ N ₃ S = 757.94) 2-7 m / z = 681.28 (C ₄₉ H ₃₅ N ₃ O = 681.82) 2-8 m / z = 669.26 (C ₄₈ H ₃₂ FN ₃ = 669.79) 2-9 m / z = 707.33 (C ₅₂ H ₄₁ N ₃ = 707.90) 2-10 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 2-11 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 2-12 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 2-13 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 2-14 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 2-15 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 2-16 m / z = 751.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 2-17 m / z = 783.27 (C ₅₆ H ₃₇ N ₃ S = 783.98) 2-18 m / z = 807.27 (C ₅₈ H ₃₇ N ₃ S = 808.00) 2-19 m / z = 731.29 (C ₅₃ H ₃₇ N ₃ O = 731.88) 2-20 m / z = 719.27 (C ₅₂ H ₃₄ FN ₃ = 719.84) 2-21 m / z = 757.35 (C ₅₆ H ₄₃ N ₃ = 757.96) 2-22 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 2-23 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 2-24 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 2-25 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 2-26 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 2-27 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 2-28 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 2-29 m / z = 783.27 (C ₅₆ H ₃₇ N ₃ S = 783.98) 2-30 m / z = 807.27 (C ₅₈ H ₃₇ N ₃ S = 808.00) 2-31 m / z = 731.29 (C ₅₃ H ₃₇ N ₃ O = 731.88) 2-32 m / z = 719.27 (C ₅₂ H ₃₇ FN ₃ = 719.84) 2-33 m / z = 757.35 (C ₅₆ H ₄₃ N ₃ = 757.96) 2-34 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 2-35 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 2-36 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 2-37 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.89) 2-38 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 2-39 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 2-40 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 2-41 m / z = 809.29 (C ₅₈ H ₃₉ N ₃ S = 810.02) 2-42 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 2-43 m / z = 757.31 (C ₅₅ H ₃₉ N ₃ O = 757.92) 2-44 m / z = 745.29 (C ₅₄ H ₃₆ FN ₃ = 745.88) 2-45 m / z = 783.36 (C ₅₈ H ₄₅ N ₃ = 784.00) 2-46 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 2-47 m / z = 879.36 (C ₆₆ H ₄₅ N ₃ = 880.02) 2-48 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 3-1 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 3-2 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 3-3 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 3-4 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 3-5 m / z = 783.27 (C ₅₆ H ₃₇ N ₃ S = 783.98) 3-6 m / z = 807.27 (C ₅₈ H ₃₇ N ₃ S = 808.00) 3-7 m / z = 731.29 (C ₅₃ H ₃₇ N ₃ O = 731.88) 3-8 m / z = 719.27 (C ₅₂ H ₃₄ FN ₃ = 719.84) 3-9 m / z = 757.35 (C ₅₆ H ₄₃ N ₃ = 757.96) 3-10 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 3-11 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 3-12 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 3-13 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 3-14 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 3-15 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 3-16 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 3-17 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 3-18 m / z = 857.29 (C ₆₂ H ₃₉ N ₃ S = 858.06) 3-19 m / z = 781.31 (C ₅₇ H ₃₉ N ₃ O = 781.94) 3-20 m / z = 769.29 (C ₅₆ H ₃₆ FN ₃ = 769.90) 3-21 m / z = 807.36 (C ₆₀ H ₄₅ N ₃ = 808.02) 3-22 m / z = 851.33 (C ₆₄ H ₄₁ N ₃ = 852.03) 3-23 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 3-24 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 3-25 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 3-26 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 3-27 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 3-28 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 3-29 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 3-30 m / z = 857.29 (C ₆₂ H ₃₉ N ₃ S = 858.06) 3-31 m / z = 781.31 (C ₅₇ H ₃₉ N ₃ O = 781.94) 3-32 m / z = 769.29 (C ₅₆ H ₃₆ FN ₃ = 769.90) 3-33 m / z = 807.36 (C ₆₀ H ₄₅ N ₃ = 808.02) 3-34 m / z = 851.33 (C ₆₄ H ₄₁ N ₃ = 852.03) 3-35 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 3-36 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 3-37 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 3-38 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 3-39 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 3-40 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 3-41 m / z = 859.30 (C ₆₂ H ₄₁ N ₃ S = 860.07) 3-42 m / z = 883.30 (C ₆₄ H ₄₁ N ₃ S = 884.10) 3-43 m / z = 807.32 (C ₅₉ H ₄₁ N ₃ O = 807.98) 3-44 m / z = 795.30 (C ₅₈ H ₃₈ FN ₃ = 795.94) 3-45 m / z = 833.38 (C ₆₂ H ₄₇ N ₃ = 834.06) 3-46 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 3-47 m / z = 929.38 (C ₇₀ H ₄₇ N ₃ = 930.14) 3-48 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 4-1 m / z = 701.28 (C ₅₂ H ₃₅ N ₃ = 701.85) 4-2 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 4-3 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 4-4 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 4-5 m / z = 783.27 (C ₅₆ H ₃₇ N ₃ S = 783.98) 4-6 m / z = 807.27 (C ₅₈ H ₃₇ N ₃ S = 808.00) 4-7 m / z = 731.29 (C ₅₃ H ₃₇ N ₃ O = 731.88) 4-8 m / z = 719.27 (C ₅₂ H ₃₄ FN ₃ = 719.84) 4-9 m / z = 757.35 (C ₅₆ H ₄₃ N ₃ = 757.96) 4-10 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 4-11 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 4-12 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 4-13 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 4-14 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 4-15 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 4-16 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 4-17 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 4-18 m / z = 857.29 (C ₆₂ H ₃₉ N ₃ S = 858.06) 4-19 m / z = 781.31 (C ₅₇ H ₃₉ N ₃ O = 781.94) 4-20 m / z = 769.29 (C ₅₆ H ₃₆ FN ₃ = 769.90) 4-21 m / z = 807.36 (C ₆₀ H ₄₅ N ₃ = 808.02) 4-22 m / z = 851.33 (C ₆₄ H ₄₁ N ₃ = 852.03) 4-23 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 4-24 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 4-25 m / z = 751.30 (C ₅₆ H ₃₇ N ₃ = 751.91) 4-26 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 4-27 m / z = 801.31 (C ₆₀ H ₃₉ N ₃ = 801.97) 4-28 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 4-29 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 4-30 m / z = 857.29 (C ₆₂ H ₃₉ N ₃ S = 858.06) 4-31 m / z = 781.31 (C ₅₇ H ₃₉ N ₃ O = 781.94) 4-32 m / z = 769.29 (C ₅₆ H ₃₆ FN ₃ = 769.90) 4-33 m / z = 807.36 (C ₆₀ H ₄₅ N ₃ = 808.02) 4-34 m / z = 851.33 (C ₆₄ H ₄₁ N ₃ = 852.03) 4-35 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 4-36 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 4-37 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 4-38 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 4-39 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 4-40 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 4-41 m / z = 859.30 (C ₆₂ H ₄₁ N ₃ S = 860.07) 4-42 m / z = 883.30 (C ₆₄ H ₄₁ N ₃ S = 884.10) 4-43 m / z = 807.32 (C ₅₉ H ₄₁ N ₃ O = 807.98) 4-44 m / z = 795.30 (C ₅₈ H ₃₈ FN ₃ = 795.94) 4-45 m / z = 833.38 (C ₆₂ H ₄₇ N ₃ = 834.06) 4-46 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 4-47 m / z = 929.38 (C ₇₀ H ₄₇ N ₃ = 930.14) 4-48 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 5-1 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.89) 5-2 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 5-3 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 5-4 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 5-5 m / z = 809.29 (C ₅₈ H ₃₉ N ₃ S = 810.02) 5-6 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.04) 5-7 m / z = 757.31 (C ₅₅ H ₃₉ N ₃ O = 757.92) 5-8 m / z = 745.29 (C ₅₄ H ₃₆ FN ₃ = 745.88) 5-9 m / z = 783.36 (C ₅₈ H ₄₅ N ₃ = 784.00) 5-10 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 5-11 m / z = 879.36 (C ₆₆ H ₄₅ N ₃ = 880.08) 5-12 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 5-13 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 5-14 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 5-15 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 5-16 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 5-17 m / z = 859.30 (C ₆₂ H ₄₁ N ₃ S = 860.07) 5-18 m / z = 883.30 (C ₆₄ H ₄₁ N ₃ S = 884.10) 5-19 m / z = 807.32 (C ₅₉ H ₄₁ N ₃ O = 807.98) 5-20 m / z = 795.30 (C ₅₈ H ₃₈ FN ₃ = 795.94) 5-21 m / z = 833.38 (C ₆₂ H ₄₇ N ₃ = 834.06) 5-22 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 5-23 m / z = 929.38 (C ₇₀ H ₄₇ N ₃ = 930.14) 5-24 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 5-25 m / z = 777.31 (C ₅₈ H ₃₉ N ₃ = 777.95) 5-26 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 5-27 m / z = 827.33 (C ₆₂ H ₄₁ N ₃ = 828.01) 5-28 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 5-29 m / z = 859.30 (C ₆₂ H ₄₁ N ₃ S = 860.07) 5-30 m / z = 883.30 (C ₆₄ H ₄₁ N ₃ S = 884.10) 5-31 m / z = 807.32 (C ₅₉ H ₄₁ N ₃ O = 807.98) 5-32 m / z = 795.30 (C ₅₈ H ₃₈ FN ₃ = 795.94) 5-33 m / z = 833.38 (C ₆₂ H ₄₇ N ₃ = 834.06) 5-34 m / z = 877.35 (C ₆₆ H ₄₃ N ₃ = 878.07) 5-35 m / z = 929.38 (C ₇₀ H ₄₇ N ₃ = 930.14) 5-36 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 5-37 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 5-38 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 5-39 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.05) 5-40 m / z = 879.36 (C ₆₆ H ₄₅ N ₃ = 880.08) 5-41 m / z = 885.32 (C ₆₄ H ₄₃ N ₃ S = 886.11) 5-42 m / z = 909.32 (C ₆₆ H ₄₃ N ₃ S = 910.13) 5-43 m / z = 883.34 (C ₆₁ H ₄₃ N ₃ O = 834.01) 5-44 m / z = 821.32 (C ₆₀ H ₄₀ FN ₃ = 821.98) 5-45 m / z = 859.39 (C ₆₄ H ₄₉ N ₃ = 860.09) 5-46 m / z = 903.36 (C ₆₈ H ₄₅ N ₃ = 904.10) 5-47 m / z = 955.39 (C ₇₂ H ₄₉ N ₃ = 956.18) 5-48 m / z = 929.38 (C ₇₀ H ₄₇ N ₃ = 930.14) 6-1 m / z = 653.26 (C ₄₆ H ₃₁ N ₅ = 653.77) 6-2 m / z = 703.27 (C ₅₀ H ₃₃ N ₅ = 703.83) 6-3 _{m / z = 703.27 (C 50} H 33 N 5 = = 703.83) 6-4 m / z = 729.29 (C ₅₂ H ₃₅ N ₅ = 729.87) 6-5 m / z = 735.25 (C ₅₀ H ₃₁ N ₅ S = 735.90) 6-6 m / z = 759.25 (C ₅₂ H ₃₃ N ₅ S = 759.92) 6-7 m / z = 683.27 (C ₄₇ H ₃₃ N ₅ O = 683.80) 6-8 m / z = 671.25 (C ₄₆ H ₃₀ FN ₅ = 671.76) 6-9 m / z = 709.32 (C ₅₀ H ₃₉ N ₅ = 709.88) 6-10 m / z = 753.29 (C ₅₄ H ₃₅ N ₅ = 753.89) 6-11 m / z = 805.32 (C ₅₈ H ₃₉ N ₅ = 805.96) 6-12 m / z = 779.30 (C ₅₆ H ₃₇ N ₅ = 779.93) 6-13 m / z = 703.27 (C ₅₀ H ₃₃ N ₅ = 703.83) 6-14 m / z = 753.29 (C ₅₄ H ₃₅ N ₅ = 753.89) 6-15 m / z = 753.29 (C ₅₄ H ₃₅ N ₅ = 753.89) 6-16 m / z = 779.30 (C ₅₆ H ₃₇ N ₅ = 779.93) 6-17 m / z = 785.26 (C ₅₄ H ₃₅ N ₅ S = 785.95) 6-18 m / z = 809.26 (C ₅₆ H ₃₅ N ₅ S = 809.98) 6-19 m / z = 733.28 (C ₅₁ H ₃₅ N ₅ O = 733.86) 6-20 m / z = 721.26 (C ₅₀ H ₃₂ FN ₅ = 721.82) 6-21 m / z = 759.34 (C ₅₄ H ₄₁ N ₅ = 759.94) 6-22 m / z = 803.30 (C ₅₈ H ₃₇ N ₅ = 803.95) 6-23 m / z = 855.34 (C ₆₂ H ₄₁ N ₅ = 856.02) 6-24 m / z = 829.32 (C ₆₀ H ₃₉ N ₅ = 829.99) 6-25 m / z = 703.27 (C ₅₀ H ₃₃ N ₅ = 703.83) 6-26 m / z = 753.29 (C ₅₄ H ₃₅ N ₅ = 753.89) 6-27 m / z = 753.29 (C ₅₄ H ₃₅ N ₅ = 753.89) 6-28 m / z = 779.30 (C ₅₆ H ₃₇ N ₅ = 779.93) 6-29 m / z = 785.26 (C ₅₄ H ₃₅ N ₅ S = 785.95) 6-30 m / z = 809.26 (C ₅₆ H ₃₅ N ₅ S = 809.98) 6-31 m / z = 733.28 (C ₅₁ H ₃₅ N ₅ O = 733.86) 6-32 m / z = 721.26 (C ₅₀ H ₃₀ FN ₅ = 721.82) 6-33 m / z = 759.34 (C ₅₄ H ₄₁ N ₅ = 759.94) 6-34 m / z = 803.30 (C ₅₈ H ₃₇ N ₅ = 803.95) 6-35 m / z = 855.34 (C ₆₂ H ₄₁ N ₅ = 856.02) 6-36 m / z = 829.32 (C ₆₀ H ₃₉ N ₅ = 829.99) 6-37 m / z = 729.29 (C ₅₂ H ₃₅ N ₅ = 729.87) 6-38 m / z = 779.30 (C ₅₆ H ₃₇ N ₅ = 779.93) 6-39 m / z = 779.30 (C ₅₆ H ₃₇ N ₅ = 779.93) 6-40 m / z = 805.32 (C ₅₂ H ₃₉ N ₅ = 805.96) 6-41 m / z = 811.28 (C ₅₆ H ₃₇ N ₅ S = 811.99) 6-42 m / z = 835.28 (C ₅₈ H ₃₇ N ₅ S = 836.01) 6-43 m / z = 759.30 (C ₅₃ H ₃₇ N ₅ O = 759.89) 6-44 m / z = 747.28 (C ₅₂ H ₃₄ FN ₅ = 747.86) 6-45 m / z = 785.35 (C ₅₆ H ₄₃ N ₅ = 785.97) 6-46 m / z = 829.32 (C ₆₀ H ₃₉ N ₅ = 829.99) 6-47 m / z = 881.35 (C ₆₄ H ₄₃ N ₅ = 882.06) 6-48 m / z = 855.34 (C ₆₂ H ₄₁ N ₅ = 856.02)

In the meantime, although each of the substituents of the compounds represented by the formula (1) is broadly related, examples of synthesis of representative compounds have been exemplarily described, but the compounds represented by the formula (1), which are not exemplarily shown in the synthesis examples, Can be configured.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the above structure, Materials can be prepared.

The compounds according to the present invention can be used in various applications in organic electroluminescent devices depending on the kind and nature of substituent groups.

Since the compounds of the present invention are controllable by the core and the substituent, they can act as various layers other than phosphorescent or fluorescent light emitting host hosts.

The organic electroluminescent device of the present invention can be manufactured by a conventional method and material for producing an organic electroluminescent device, except that the above-described compounds are used to form one or more organic substance layers.

It is obvious that 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 light-emission assisting layer, an electron injecting layer, an electron transporting layer, and a hole injecting layer.

Meanwhile, the compound of the present invention can be used in a soluble process. That is, the organic compound layer of the organic electronic device described later can be formed by a soluble process of the compound. That is, when the compound is used as an organic material layer, the organic material layer may be formed by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Lt; RTI ID = 0.0 > a < / RTI > fewer layers.

Organic electric devices in which the compounds of the present invention can be used include, for example, organic electroluminescent devices (OLED), organic solar cells, organic photoconductor (OPC) drums, organic transistors (organic TFT)

The organic electroluminescent device (OLED) will be described as one example of organic electroluminescent devices to which the compounds of the present invention can be applied, but the present invention is not limited thereto and the above-described compounds may be applied to various organic electroluminescent devices.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode and an organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of the present invention to provide.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

The organic electroluminescent device according to another embodiment of the present invention can be manufactured by the same method as the organic electroluminescent device except that at least one layer of the organic compound layer including the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, Can be made with a structure known in the art using conventional manufacturing methods and materials in the art.

The structure of an organic electroluminescent device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited to these structures. Reference numeral 101 denotes a substrate, 102 denotes an anode, 103 denotes a hole injection layer (HIL), 104 denotes a hole transport layer (HTL), 105 denotes a light emitting layer (EML), 106 denotes an electron injection layer (EIL) ETL), and 108 denotes a cathode.

The organic electroluminescent device has a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for blocking the movement of electrons, a luminescent auxiliary layer for assisting or assisting luminescence and a protective layer It may be located. In the case of the protective layer, it may be formed to protect the organic layer at the uppermost layer or to protect the cathode.

At this time, the compound of the present invention may be included in at least one of organic compound layers including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

Specifically, the compound of the present invention may be used as a substitute for one or more of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, May be used. Of course, it can be used for more than two layers, not only one layer of the organic material layer.

In particular, it can be used as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, a light emitting material and a passivation (keping) material according to the compound of the present invention, It can be used as a dopant, and can be used as a hole injecting and hole transporting layer.

For example, the organic electroluminescent device according to another embodiment of the present invention may be formed by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, Oxide or an alloy thereof to form an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer on the anode, depositing a material usable as a cathode thereon .

In addition to such a method, the organic material may be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, but is not limited thereto and may have a single layer structure.

In addition, the organic material layer may be formed by using a variety of polymer materials, not by vapor deposition, but by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, It can be manufactured in a small number of layers.

The organic electroluminescent device according to another embodiment of the present invention may be used in a soluble process such as a spin coating process or an ink jet process.

The substrate may be a silicon wafer, a quartz or glass plate, a metal plate, a plastic film, or a sheet.

An anode is placed on the substrate. Such an anode injects holes into the hole injection layer located thereon. The anode material may be a material having a large work function so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

A hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are that the hole injection efficiency from the anode is high and the injected holes must be efficiently transported. For this purpose, the ionization potential is small, the transparency to visible light is high, and the stability against holes is excellent.

As the hole injecting material, a hole can be injected from the anode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injecting material may be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

A hole transport layer is disposed on the hole injection layer. The hole transport layer transports holes from the hole injection layer to an organic light emitting layer disposed thereon, and has high hole mobility, stability to holes, and electrons. In addition to these general requirements, heat resistance to a device is required when it is applied for vehicle display, and it may be a material having a glass transition temperature (Tg) of 70 DEG C or more.

Materials satisfying such conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compounds, silicone-based arylamine compounds, and the like.

An organic light emitting layer is disposed on the hole transporting layer. The organic light emitting layer is a layer in which holes and electrons injected from the anode and the cathode respectively recombine to emit light, and the organic light emitting layer is made of a material having high quantum efficiency. The light emitting material may be a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.

Materials or compounds that satisfy these conditions include Alq3 in the case of green, Balq (8-hydroxyquinoline beryllium salt) in the case of blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) biphenyl series, Spiro material, Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenolithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complexes, imidazoles, thiazole and oxazole metal complexes, and perylene and BczVBi (3,3 ' (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine). In the case of red, the green luminescent material was doped with DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl- -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile).

Polymers such as a polyphenylene vinylene (PPV) -based polymer and polyfluorene may be used for the organic light emitting layer when the light emitting layer is formed using processes such as inkjet printing, roll coating and spin coating .

An electron transporting layer is disposed on the organic light emitting layer. Such an electron transporting layer requires a material capable of efficiently injecting electrons with a high electron injection efficiency from a cathode disposed thereon. For this purpose, it is required to be made of a material having high electron affinity, high electron transfer rate and excellent stability against electrons.

Specific examples of the electron transporting material satisfying such conditions include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

An electron injection layer is deposited on the electron transport layer. The electron injection layer may be a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI or Tf-6P, boron compounds, and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ANGSTROM to 300 ANGSTROM.

On the electron injection layer, a cathode is positioned. These cathodes serve to inject electrons. The material used for the cathode may be the material used for the anode and may be a metal having a low work function for efficient electron injection. Particularly suitable metals such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or their alloys may be used. Also, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum, etc., having a thickness of 100 μm or less may be used.

As described above, the compound of the present invention can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are suitable for the fluorescence of all colors such as red, green, It can be used as a host or dopant material of various colors.

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.

Meanwhile, the present invention includes a display device including the above-described organic electronic device and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention may be a mobile communication terminal such as a mobile phone and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Evaluation of manufacturing of organic electric device

compare Experimental Example  One

Organic electroluminescent devices were fabricated according to a conventional method using various compounds obtained through synthesis as a hole transport layer. First, 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter referred to as 2T-NATA ) Was formed by vacuum evaporation to a thickness of 10 nm.

Subsequently, the hole transport layer was formed by vacuum evaporation of the developed material as the electron transport compound to a thickness of 30 nm. After the hole transport layer was formed, when the developed material was measured as a hole transport layer, a light-emitting layer doped with 7% of BD-052X (Idemitus Co., Ltd.) having a thickness of 45 nm (in this case, BD-052X is a blue fluorescent dopant , 9,10-di (naphthalene-2-anthracene (AND)) was used as the luminescent host material.

(2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and then (1,1'- Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm as an electron injecting layer. Thereafter, LiF as an alkali metal halide was vapor-deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm, and this Al / LiF was used as a cathode to produce an organic electroluminescence device.

Comparative Example 1) NPB

compound Voltage Current Density Brightness
(cd / m < 2 & Efficiency Lifetime
T (90) CIE
(x, y) Comparative Example (1) Comparative Example (1) 6.6 7.5 300.0 4.0 57.4 (0.15, 0.15) Example (1) Compound (2-1) 5.2 6.7 300.0 4.5 103.9 (0.15, 0.14) Example (2) Compound (2-2) 4.2 5.2 300.0 5.8 101.2 (0.15, 0.14) Example (3) Compound (2-3) 4.7 5.9 300.0 5.1 95.3 (0.14, 0.14) Example (4) Compound (2-4) 5.5 5.5 300.0 5.4 97.3 (0.15, 0.14) Example (5) Compound (2-5) 5.3 6.1 300.0 4.9 102.6 (0.14, 0.14) Example (6) Compound (2-6) 5.2 6.8 300.0 4.4 115.4 (0.15, 0.15) Example (7) Compound (2-7) 5.2 6.2 300.0 4.9 132.5 (0.15, 0.13) Example (8) Compound (2-8) 6.1 5.2 300.0 5.8 126.0 (0.15, 0.14) Example (9) Compound (2-9) 5.9 5.8 300.0 5.2 120.8 (0.15, 0.16) Example (10) Compound (2-10) 4.3 4.9 300.0 6.2 100.6 (0.15, 0.14) Example (11) Compound (2-11) 5.0 5.2 300.0 5.7 120.8 (0.14, 0.14) Example (12) The compound (2-12) 6.0 6.6 300.0 4.5 130.5 (0.14, 0.14) Example (13) The compound (2-13) 4.1 4.7 300.0 6.4 145.6 (0.15, 0.13) Example (14) The compound (2-14) 4.8 6.1 300.0 4.9 111.4 (0.15, 0.15) Example (15) Compound (2-15) 6.2 5.3 300.0 5.7 116.8 (0.15, 0.16) Example (16) The compound (2-16) 4.1 5.5 300.0 5.4 141.4 (0.15, 0.14) Example (17) Compound (2-17) 5.2 5.0 300.0 6.0 132.4 (0.15, 0.14) Example (18) Compound (2-18) 5.2 6.1 300.0 4.9 104.7 (0.15, 0.15) Example (19) Compound (2-19) 4.5 5.5 300.0 5.4 94.6 (0.15, 0.14) Example (20) Compound (2-20) 5.2 5.8 300.0 5.1 95.9 (0.15, 0.14) Example (21) Compound (2-21) 5.3 6.7 300.0 4.5 129.9 (0.14, 0.14) Example (22) Compound (2-22) 6.0 6.8 300.0 4.4 108.6 (0.15, 0.14) Example (23) The compound (2-23) 6.2 6.6 300.0 4.5 149.0 (0.15, 0.13) Example (24) Compound (2-24) 5.9 5.0 300.0 6.0 96.4 (0.15, 0.14) Example (25) Compound (2-25) 5.5 5.2 300.0 5.8 124.1 (0.15, 0.14) Example (26) Compound (2-26) 5.2 5.4 300.0 5.5 119.1 (0.15, 0.14) Example (27) Compound (2-27) 4.3 4.9 300.0 6.2 146.6 (0.15, 0.13) Example (28) Compound (2-28) 4.3 4.7 300.0 6.4 132.9 (0.15, 0.13) Example (29) Compound (2-29) 5.2 5.2 300.0 5.8 102.6 (0.15, 0.14) Example (30) Compound (2-30) 6.2 5.2 300.0 5.8 148.9 (0.15, 0.15) Example (31) Compound (2-31) 4.1 5.8 300.0 5.2 124.8 (0.15, 0.15) Example (32) Compound (2-32) 5.4 5.5 300.0 5.4 102.4 (0.15, 0.14) Example (33) Compound (2-33) 6.2 5.3 300.0 5.6 142.0 (0.15, 0.14) Example (34) Compound (2-34) 4.0 6.0 300.0 5.0 137.0 (0.15, 0.16) Example (35) Compound (2-35) 5.3 6.1 300.0 5.0 92.0 (0.14, 0.14) Example (36) Compound (2-36) 5.5 5.1 300.0 5.8 131.1 (0.15, 0.13) Example (37) Compound (2-37) 5.4 5.6 300.0 5.4 135.3 (0.15, 0.14) Example (38) Compound (2-38) 4.2 5.8 300.0 5.2 127.0 (0.15, 0.14) Example (39) Compound (2-39) 4.0 4.9 300.0 6.1 108.5 (0.15, 0.13) Example (40) Compound (2-40) 4.0 4.6 300.0 6.5 149.6 (0.15, 0.14) Example (41) Compound (2-41) 4.6 5.0 300.0 6.0 125.4 (0.15, 0.13) Example (42) Compound (2-42) 5.4 4.9 300.0 6.1 127.2 (0.15, 0.14) Example (43) Compound (2-43) 4.2 4.9 300.0 6.1 122.4 (0.15, 0.14) Example (44) Compound (2-44) 5.4 6.1 300.0 5.0 112.7 (0.15, 0.15) Example (45) Compound (2-45) 4.9 4.8 300.0 6.2 104.1 (0.15, 0.13) Example (46) Compound (2-46) 5.2 6.7 300.0 4.4 104.9 (0.15, 0.14) Example (47) Compound (2-47) 6.4 4.8 300.0 6.3 120.0 (0.15, 0.13) Example (48) Compound (2-48) 6.3 5.6 300.0 5.4 134.8 (0.15, 0.14) Example (49) Compound (3-1) 5.5 6.6 300.0 4.5 108.7 (0.15, 0.14) Example (50) The compound (3-2) 4.2 5.5 300.0 5.5 119.4 (0.15, 0.14) Example (51) Compound (3-3) 4.3 5.1 300.0 5.9 110.4 (0.15, 0.14) Example (52) Compound (3-4) 6.3 5.6 300.0 5.4 142.6 (0.14, 0.14) Example (53) Compound (3-5) 5.0 6.7 300.0 4.5 100.1 (0.14, 0.14) Example (54) Compound (3-6) 5.3 6.8 300.0 4.4 145.2 (0.15, 0.14) Example (55) Compound (3-7) 5.1 4.7 300.0 6.3 143.0 (0.15, 0.13) Example (56) Compound (3-8) 4.5 6.9 300.0 4.4 146.7 (0.15, 0.15) Example (57) Compound (3-9) 5.3 6.4 300.0 4.7 103.0 (0.15, 0.13) Example (58) Compound (3-10) 6.0 5.3 300.0 5.7 138.1 (0.15, 0.14) Example (59) The compound (3-11) 4.9 6.8 300.0 4.4 108.8 (0.15, 0.14) Example (60) The compound (3-12) 4.6 6.0 300.0 5.0 132.3 (0.14, 0.14) Example (61) The compound (3-13) 5.4 6.7 300.0 4.4 126.4 (0.15, 0.13) Example (62) The compound (3-14) 5.9 6.8 300.0 4.4 135.4 (0.15, 0.14) Example (63) The compound (3-15) 4.1 6.3 300.0 4.8 100.1 (0.15, 0.14) Example (64) The compound (3-16) 4.8 4.7 300.0 6.4 116.6 (0.14, 0.14) Example (65) Compound (3-17) 4.5 4.9 300.0 6.2 111.7 (0.15, 0.16) Example (66) Compound (3-18) 5.2 5.0 300.0 5.9 109.7 (0.15, 0.13) Example (67) Compound (3-19) 5.7 5.6 300.0 5.3 141.2 (0.15, 0.14) Example (68) Compound (3-20) 6.4 4.8 300.0 6.2 119.1 (0.15, 0.14) Example (69) Compound (3-21) 6.0 5.0 300.0 6.0 101.2 (0.15, 0.14) Example (70) Compound (3-22) 4.4 5.8 300.0 5.1 146.8 (0.15, 0.16) Example (71) Compound (3-23) 4.8 6.0 300.0 5.0 114.9 (0.14, 0.14) Example (72) Compound (3-24) 4.1 6.3 300.0 4.7 95.9 (0.15, 0.14) Example (73) Compound (3-25) 5.6 5.0 300.0 6.0 118.6 (0.14, 0.14) Example (74) Compound (3-26) 6.4 4.8 300.0 6.2 128.3 (0.15, 0.15) Example (75) Compound (3-27) 4.1 4.7 300.0 6.4 116.2 (0.15, 0.13) Example (76) Compound (3-28) 6.4 6.2 300.0 4.8 121.6 (0.15, 0.14) Example (77) Compound (3-29) 5.3 4.9 300.0 6.1 111.8 (0.15, 0.13) Example (78) Compound (3-30) 4.5 5.1 300.0 5.9 140.3 (0.15, 0.14) Example (79) Compound (3-31) 4.1 6.6 300.0 4.5 96.3 (0.14, 0.14) Example (80) Compound (3-32) 4.8 5.5 300.0 5.5 124.5 (0.14, 0.14) Example (81) Compound (3-33) 4.2 6.0 300.0 5.0 106.0 (0.15, 0.15) Example (82) Compound (3-34) 4.8 5.2 300.0 5.8 105.4 (0.15, 0.14) Example (83) Compound (3-35) 6.5 6.2 300.0 4.8 96.3 (0.15, 0.14) Example (84) Compound (3-36) 5.8 5.7 300.0 5.2 127.7 (0.15, 0.13) Example (85) Compound (3-37) 5.2 5.5 300.0 5.5 148.6 (0.14, 0.14) Example (86) Compound (3-38) 4.4 5.8 300.0 5.2 119.5 (0.14, 0.14) Example (87) Compound (3-39) 4.1 4.7 300.0 6.3 134.1 (0.14, 0.14) Example (88) Compound (3-40) 4.4 5.1 300.0 5.9 115.7 (0.15, 0.13) Example (89) Compound (3-41) 5.5 5.1 300.0 5.9 139.9 (0.15, 0.14) Example (90) Compound (3-42) 4.9 6.6 300.0 4.5 99.9 (0.15, 0.14) Example (91) Compound (3-43) 6.4 5.5 300.0 5.5 98.1 (0.15, 0.13) Example (92) Compound (3-44) 5.5 5.0 300.0 6.0 132.9 (0.14, 0.14) Example (93) Compound (3-45) 5.8 5.8 300.0 5.1 91.1 (0.15, 0.14) Example (94) Compound (3-46) 5.1 6.8 300.0 4.4 90.7 (0.15, 0.14) Example (95) Compound (3-47) 6.0 4.7 300.0 6.4 135.4 (0.14, 0.14) Example (96) Compound (3-48) 5.5 6.7 300.0 4.5 132.8 (0.15, 0.13) Example (97) Compound (4-1) 5.9 5.6 300.0 5.3 147.2 (0.15, 0.16) Example (98) Compound (4-2) 4.6 4.8 300.0 6.2 100.5 (0.15, 0.14) Example (99) Compound (4-3) 5.5 4.7 300.0 6.4 125.3 (0.15, 0.13) Example (100) The compound (4-4) 5.1 4.6 300.0 6.5 103.2 (0.14, 0.14) Example (101) Compound (4-5) 5.4 6.9 300.0 4.4 145.8 (0.15, 0.14) Example (102) Compound (4-6) 5.7 5.0 300.0 6.0 106.1 (0.15, 0.13) Example (103) The compound (4-7) 4.0 4.7 300.0 6.4 120.6 (0.14, 0.14) Example (104) Compound (4-8) 4.9 5.1 300.0 5.8 148.4 (0.14, 0.14) Example (105) Compound (4-9) 4.6 6.9 300.0 4.4 145.9 (0.15, 0.13) Example (106) Compound (4-10) 5.8 6.6 300.0 4.5 116.0 (0.15, 0.14) Example (107) The compound (4-11) 4.5 5.2 300.0 5.8 126.4 (0.14, 0.14) Example (108) The compound (4-12) 6.4 5.0 300.0 6.0 104.4 (0.15, 0.13) Example (109) The compound (4-13) 4.9 4.9 300.0 6.2 132.3 (0.14, 0.14) Example (110) The compound (4-14) 5.8 6.0 300.0 5.0 137.4 (0.15, 0.14) Example (111) Compound (4-15) 4.3 5.1 300.0 5.8 102.3 (0.14, 0.14) Example (112) The compound (4-16) 4.9 6.1 300.0 4.9 124.4 (0.15, 0.14) Example (113) Compound (4-17) 4.2 5.7 300.0 5.3 132.5 (0.15, 0.16) Example (114) Compound (4-18) 5.7 6.0 300.0 5.0 112.2 (0.14, 0.14) Example (115) Compound (4-19) 5.4 6.4 300.0 4.7 136.8 (0.14, 0.14) Example (116) Compound (4-20) 4.1 6.4 300.0 4.7 96.0 (0.15, 0.14) Example (117) Compound (4-21) 5.7 5.7 300.0 5.3 106.1 (0.15, 0.14) Example (118) Compound (4-22) 6.1 4.7 300.0 6.4 126.0 (0.14, 0.14) Example (119) Compound (4-23) 6.2 4.7 300.0 6.4 111.3 (0.15, 0.14) Example (120) Compound (4-24) 6.0 6.6 300.0 4.6 101.8 (0.14, 0.14) Example (121) Compound (4-25) 4.9 5.8 300.0 5.2 101.7 (0.15, 0.13) Example (122) Compound (4-26) 6.4 6.8 300.0 4.4 111.1 (0.14, 0.14) Example (123) Compound (4-27) 5.6 6.0 300.0 5.0 94.0 (0.15, 0.14) Example (124) Compound (4-28) 6.2 5.7 300.0 5.3 99.8 (0.14, 0.14) Example (125) Compound (4-29) 4.8 5.7 300.0 5.2 99.4 (0.15, 0.13) Example (126) Compound (4-30) 5.1 5.3 300.0 5.6 99.0 (0.15, 0.14) Example (127) Compound (4-31) 4.9 5.8 300.0 5.2 149.1 (0.15, 0.14) Example (128) Compound (4-32) 5.4 5.6 300.0 5.4 131.8 (0.14, 0.14) Example (129) Compound (4-33) 5.2 5.9 300.0 5.1 144.2 (0.15, 0.14) Example (130) Compound (4-34) 4.3 5.3 300.0 5.7 129.1 (0.15, 0.13) Example (131) Compound (4-35) 4.8 4.9 300.0 6.1 97.2 (0.15, 0.14) Example (132) Compound (4-36) 5.0 6.6 300.0 4.5 147.3 (0.15, 0.16) Example (133) Compound (4-37) 4.3 5.5 300.0 5.4 90.5 (0.15, 0.14) Example (134) Compound (4-38) 4.2 5.9 300.0 5.1 145.8 (0.14, 0.14) Example (135) Compound (4-39) 5.7 5.3 300.0 5.6 118.8 (0.14, 0.14) Example (136) The compound (4-40) 5.8 5.5 300.0 5.5 124.8 (0.15, 0.13) Example (137) Compound (4-41) 5.6 6.9 300.0 4.4 132.1 (0.15, 0.15) Example (138) Compound (4-42) 6.1 5.3 300.0 5.7 116.1 (0.15, 0.16) Example (139) Compound (4-43) 6.1 5.1 300.0 5.9 133.3 (0.15, 0.14) Example (140) Compound (4-44) 5.3 5.7 300.0 5.2 111.7 (0.15, 0.14) Example (141) Compound (4-45) 6.0 5.7 300.0 5.2 105.2 (0.15, 0.14) Example (142) Compound (4-46) 6.4 5.6 300.0 5.3 113.2 (0.15, 0.15) Example (143) Compound (4-47) 4.8 6.3 300.0 4.7 144.5 (0.15, 0.14) Example (144) Compound (4-48) 4.4 4.7 300.0 6.4 130.7 (0.15, 0.14) Example (145) Compound (5-1) 5.5 6.2 300.0 4.9 107.7 (0.14, 0.14) Example (146) Compound (5-2) 4.6 6.0 300.0 5.0 92.6 (0.15, 0.14) Example (147) Compound (5-3) 4.1 6.5 300.0 4.6 126.7 (0.15, 0.13) Example (148) Compound (5-4) 4.6 4.7 300.0 6.4 94.7 (0.15, 0.14) Example (149) Compound (5-5) 4.7 4.7 300.0 6.3 133.8 (0.15, 0.14) Example (150) Compound (5-6) 5.1 6.5 300.0 4.6 138.8 (0.15, 0.14) Example (151) The compound (5-7) 6.4 4.7 300.0 6.3 95.0 (0.15, 0.13) Example (152) Compound (5-8) 5.4 5.8 300.0 5.2 121.1 (0.15, 0.13) Example (153) Compound (5-9) 5.4 4.8 300.0 6.3 131.5 (0.15, 0.14) Example (154) The compound (5-10) 6.3 5.1 300.0 5.9 114.8 (0.15, 0.15) Example (155) Compound (5-11) 4.2 4.8 300.0 6.2 135.4 (0.15, 0.15) Example (156) The compound (5-12) 6.2 5.7 300.0 5.2 145.8 (0.15, 0.14) Example (157) The compound (5-13) 5.0 5.0 300.0 6.0 114.0 (0.15, 0.14) Example (158) The compound (5-14) 6.4 6.2 300.0 4.8 128.6 (0.15, 0.16) Example (159) The compound (5-15) 4.0 5.1 300.0 5.8 96.8 (0.14, 0.14) Example (160) The compound (5-16) 4.0 5.8 300.0 5.2 136.3 (0.15, 0.13) Example (161) Compound (5-17) 6.1 4.7 300.0 6.3 124.0 (0.15, 0.14) Example (162) Compounds (5-18) 4.5 4.7 300.0 6.3 133.3 (0.15, 0.14) Example (163) The compound (5-19) 5.2 4.7 300.0 6.3 119.0 (0.15, 0.13) Example (164) The compound (5-20) 5.3 5.5 300.0 5.5 95.9 (0.15, 0.14) Example (165) Compound (5-21) 5.3 5.9 300.0 5.1 136.7 (0.15, 0.13) Example (166) Compound (5-22) 4.1 6.2 300.0 4.8 119.4 (0.15, 0.14) Example (167) Compound (5-23) 6.1 6.4 300.0 4.7 112.0 (0.15, 0.13) Example (168) Compounds (5-24) 5.0 6.5 300.0 4.6 101.7 (0.15, 0.14) Example (169) Compound (5-25) 5.8 4.9 300.0 6.2 102.2 (0.15, 0.15) Example (170) The compound (5-26) 5.3 6.7 300.0 4.5 137.3 (0.15, 0.15) Example (171) Compound (5-27) 5.4 4.9 300.0 6.1 111.9 (0.15, 0.14) Example (172) Compound (5-28) 4.7 5.5 300.0 5.4 101.2 (0.15, 0.14) Example (173) Compound (5-29) 4.8 5.4 300.0 5.6 140.1 (0.15, 0.16) Example (174) Compound (5-30) 4.7 5.1 300.0 5.9 142.2 (0.14, 0.14) Example (175) Compound (5-31) 5.4 4.9 300.0 6.1 110.0 (0.15, 0.13) Example (176) Compound (5-32) 5.3 6.0 300.0 5.0 100.2 (0.15, 0.14) Example (177) Compound (5-33) 5.0 6.4 300.0 4.7 129.7 (0.15, 0.14) Example (178) Compound (5-34) 5.3 5.6 300.0 5.4 132.5 (0.15, 0.13) Example (179) Compound (5-35) 4.5 5.8 300.0 5.1 137.1 (0.15, 0.14) Example (180) Compound (5-36) 5.5 4.9 300.0 6.1 140.5 (0.15, 0.13) Example (181) Compound (5-37) 6.3 5.4 300.0 5.5 116.5 (0.15, 0.13) Example (182) Compound (5-38) 6.5 6.5 300.0 4.6 131.3 (0.15, 0.14) Example (183) Compound (5-39) 6.1 6.0 300.0 5.0 144.3 (0.15, 0.15) Example (184) Compound (5-40) 4.4 5.7 300.0 5.2 146.6 (0.15, 0.15) Example (185) Compound (5-41) 5.8 6.0 300.0 5.0 107.4 (0.15, 0.14) Example (186) Compound (5-42) 6.2 6.3 300.0 4.8 115.8 (0.15, 0.14) Example (187) Compound (5-43) 6.3 6.4 300.0 4.7 120.9 (0.15, 0.16) Example (188) Compound (5-44) 5.7 5.6 300.0 5.4 140.8 (0.14, 0.14) Example (189) Compound (5-45) 6.3 6.8 300.0 4.4 104.9 (0.15, 0.13) Example (190) Compound (5-46) 6.0 5.3 300.0 5.6 141.2 (0.15, 0.14) Example (191) Compound (5-47) 6.1 5.7 300.0 5.3 96.7 (0.15, 0.14) Example (192) Compound (5-48) 5.4 5.4 300.0 5.6 95.4 (0.15, 0.13) Example (193) Compound (6-1) 4.8 6.3 300.0 4.8 135.4 (0.15, 0.14) Example (194) Compound (6-2) 6.1 5.6 300.0 5.3 124.4 (0.15, 0.13) Example (195) Compound (6-3) 4.7 4.7 300.0 6.4 143.4 (0.14, 0.14) Example (196) Compound (6-4) 4.7 4.9 300.0 6.2 128.2 (0.15, 0.14) Example (197) Compound (6-5) 6.3 5.3 300.0 5.7 116.1 (0.14, 0.14) Example (198) Compound (6-6) 5.0 4.9 300.0 6.1 93.2 (0.15, 0.15) Example (199) Compound (6-7) 5.7 5.8 300.0 5.2 110.3 (0.15, 0.13) Example (200) Compound (6-8) 6.0 4.7 300.0 6.4 105.8 (0.15, 0.14) Example (201) Compound (6-9) 4.3 4.7 300.0 6.4 101.0 (0.15, 0.16) Example (202) The compound (6-10) 5.5 4.7 300.0 6.4 131.7 (0.15, 0.14) Example (203) Compound (6-11) 6.0 6.7 300.0 4.4 127.9 (0.14, 0.14) Example (204) The compound (6-12) 5.2 5.9 300.0 5.1 111.3 (0.14, 0.14) Example (205) Compounds (6-13) 4.5 5.2 300.0 5.8 140.6 (0.15, 0.13) Example (206) The compound (6-14) 4.7 6.9 300.0 4.3 128.5 (0.15, 0.15) Example (207) The compound (6-15) 4.4 6.1 300.0 4.9 134.8 (0.15, 0.16) Example (208) Compounds (6-16) 5.6 6.1 300.0 4.9 100.1 (0.15, 0.14) Example (209) Compound (6-17) 4.9 5.4 300.0 5.6 135.5 (0.15, 0.14) Example (210) The compound (6-18) 6.2 5.8 300.0 5.1 97.9 (0.15, 0.15) Example (211) Compound (6-19) 4.1 6.3 300.0 4.8 110.8 (0.15, 0.14) Example (212) Compound (6-20) 6.3 5.7 300.0 5.2 94.9 (0.15, 0.14) Example (213) Compound (6-21) 6.4 5.6 300.0 5.3 111.8 (0.14, 0.14) Example (214) Compound (6-22) 4.7 5.1 300.0 5.9 133.8 (0.15, 0.14) Example (215) Compound (6-23) 6.2 5.5 300.0 5.5 128.4 (0.15, 0.13) Example (216) Compound (6-24) 4.2 5.1 300.0 5.9 93.8 (0.15, 0.14) Example (217) Compound (6-25) 4.3 6.0 300.0 5.0 104.0 (0.15, 0.14) Example (218) Compound (6-26) 5.1 4.8 300.0 6.2 111.9 (0.15, 0.14) Example (219) Compound (6-27) 4.8 6.2 300.0 4.9 122.7 (0.15, 0.13) Example (220) Compound (6-28) 6.3 5.7 300.0 5.3 90.1 (0.15, 0.13) Example (221) Compound (6-29) 5.0 5.4 300.0 5.5 113.5 (0.15, 0.14) Example (222) Compound (6-30) 6.2 5.3 300.0 5.7 98.9 (0.15, 0.15) Example (223) Compound (6-31) 4.6 5.3 300.0 5.6 120.5 (0.15, 0.15) Example (224) Compound (6-32) 4.7 4.6 300.0 6.5 106.0 (0.15, 0.14) Example (225) Compound (6-33) 4.0 5.3 300.0 5.7 106.7 (0.15, 0.14) Example (226) Compound (6-34) 6.2 5.0 300.0 6.0 106.8 (0.15, 0.16) Example (227) Compound (6-35) 4.9 6.9 300.0 4.4 112.6 (0.14, 0.14) Example (228) Compound (6-36) 5.9 5.1 300.0 5.9 121.2 (0.15, 0.13) Example (229) Compound (6-37) 5.5 6.6 300.0 4.5 112.6 (0.15, 0.14) Example (230) Compound (6-38) 5.4 5.8 300.0 5.2 109.2 (0.15, 0.14) Example (231) Compound (6-39) 5.0 6.0 300.0 5.0 113.8 (0.15, 0.13) Example (232) Compound (6-40) 4.2 6.2 300.0 4.8 128.6 (0.15, 0.14) Example (233) Compound (6-41) 4.7 6.8 300.0 4.4 148.2 (0.15, 0.13) Example (234) Compound (6-42) 6.0 5.8 300.0 5.2 131.0 (0.15, 0.14) Example (235) Compound (6-43) 6.4 6.0 300.0 5.0 125.2 (0.15, 0.14) Example (236) Compound (6-44) 5.1 5.6 300.0 5.3 93.5 (0.15, 0.15) Example (237) Compound (6-45) 6.1 6.6 300.0 4.5 135.0 (0.15, 0.13) Example (238) Compound (6-46) 5.5 6.9 300.0 4.3 102.9 (0.15, 0.14) Example (239) Compound (6-47) 4.7 6.1 300.0 4.9 101.0 (0.15, 0.13) Example (240) Compound (6-48) 6.0 6.5 300.0 4.6 111.9 (0.15, 0.14)

compare Experimental Example  2

An organic electroluminescent device was fabricated by a conventional method using a compound obtained through synthesis as a luminescent host material in a light emitting layer. First, a film of copper phthalocyanine (hereinafter referred to as CuPc) was vacuum deposited on the ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited on the film to a thickness of 30 nm to form a hole transport layer . (2-phenylpyridine) iridium (hereinafter, referred to as I r (ppy)) as a phosphorescent Ir metal complex dopant after depositing a hole transporting layer, depositing the compound developed on the hole transporting layer as a phosphorescent host material, ) ≪ / RTI > ₃ ) was added. At this time, the concentration of I r (ppy) _{3 in} the light emitting layer was 5 wt%. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and electron injection Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm, then Al was deposited to a thickness of 150 nm, and this Al / LiF was used as a cathode. Thus, an organic electroluminescent device was manufactured.

Comparative Example 1) CBP

For comparison, an organic electroluminescent device having the same structure as that of the test example was prepared using a compound represented by the following formula (hereinafter abbreviated as CBP) instead of the compound of the present invention as a luminescent host material.

compound Voltage Current Density Brightness
(cd / m < 2 & Efficiency Lifetime
T (90) CIE
(x, y) Comparative Example (1) Comparative Example (1) 6.4 7.3 300.0 4.1 60.8 (0.33, 0.61) Example (1) Compound (2-10) 6.0 4.8 300.0 6.2 103.5 (0.32, 0.61) Example (2) Compound (2-18) 4.5 5.4 300.0 5.6 99.1 (0.33, 0.60) Example (3) Compound (2-34) 6.0 5.9 300.0 5.1 101.5 (0.30, 0.61) Example (4) Compound (2-40) 4.1 4.5 300.0 6.6 147.7 (0.31, 0.61) Example (5) Compound (2-48) 4.5 5.9 300.0 5.1 142.1 (0.31, 0.60) Example (6) The compound (3-15) 6.3 5.5 300.0 5.4 125.5 (0.33, 0.61) Example (7) Compound (3-24) 6.0 5.2 300.0 5.7 148.3 (0.32, 0.60) Example (8) Compound (3-34) 5.9 5.1 300.0 5.9 130.0 (0.32, 0.61) Example (9) Compound (3-46) 5.1 5.2 300.0 5.7 121.2 (0.33, 0.60) Example (10) Compound (3-47) 4.5 6.1 300.0 4.9 143.5 (0.30, 0.60) Example (11) The compound (4-11) 5.6 6.1 300.0 4.9 115.4 (0.30, 0.61) Example (12) Compound (4-20) 4.2 6.3 300.0 4.8 106.7 (0.32, 0.61) Example (13) Compound (4-34) 4.5 5.3 300.0 5.6 103.1 (0.31, 0.61) Example (14) The compound (4-40) 4.2 5.8 300.0 5.2 133.3 (0.31, 0.60) Example (15) Compound (4-42) 6.4 5.2 300.0 5.8 102.2 (0.31, 0.60) Example (16) Compound (5-4) 4.7 6.1 300.0 4.9 137.6 (0.32, 0.61) Example (17) Compounds (5-18) 5.5 6.6 300.0 4.5 103.8 (0.31, 0.61) Example (18) Compound (5-34) 5.1 4.7 300.0 6.4 96.3 (0.33, 0.60) Example (19) Compound (5-38) 5.5 4.9 300.0 6.1 133.1 (0.31, 0.60) Example (20) Compound (5-41) 6.3 5.2 300.0 5.8 111.5 (0.32, 0.61) Example (21) Compound (6-2) 4.4 5.8 300.0 5.2 115.0 (0.32, 0.61) Example (22) The compound (6-15) 4.8 6.7 300.0 4.5 96.7 (0.33, 0.60) Example (23) Compound (6-23) 4.7 6.8 300.0 4.4 145.0 (0.30, 0.61) Example (24) Compound (6-30) 5.3 6.0 300.0 5.0 134.1 (0.31, 0.61) Example (25) Compound (6-47) 4.2 5.6 300.0 5.4 112.8 (0.31, 0.60)

As can be seen from the results of the above tables, the organic electroluminescence device using the organic electroluminescence device material of the present invention is used as a light emitting host and a hole transporting material, thereby remarkably improving the low driving voltage, color purity, .

It is obvious that 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 light-emission assisting layer, an electron injecting layer, an electron transporting layer, and a hole injecting layer.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. 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 (10)

An organic electronic device comprising a compound represented by the following formula (1):
(1)

In the above formula (1)
₁₎ Ar 1 is selected from hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of the alkyl amine group, C ₁ ~ C alkyl thiophene group of _20, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of, C ₆ ~ C ₆₀ A C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group A C ₆ -C ₆₀ aryl group unsubstituted or substituted with one or more substituents; A halogen atom, 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 ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, N, S, at least one substituted or unsubstituted heteroaryl group of C ₅ ~ C ₆₀ having a one; 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ -C ₃₀ aryloxy group; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ 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 Lt;
2) L ₁ is C ₅ -C ₆₀ substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and amino group; Lt; / RTI >
3) L ₂ is C ₆ -C ₆₀ substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy and amino, An arylene group; A heteroaryl group of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₅ ~ C ₆₀ of; And a substituted or unsubstituted divalent aliphatic hydrocarbon. The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula (6)

Ar _1, L ₂ in Formula 6 is the same as Ar _1, L ₂ in Formula (1). The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is selected from the following compounds:

A first electrode, at least one organic layer containing any one of the compounds described in any one of claims 1 to 3, and a second electrode in the form of a layer stacked in this order. The organic electroluminescent device according to claim 4, wherein the organic compound layer is formed by a soluble process. The organic electroluminescent device according to claim 4, wherein the organic material layer is used as a light emitting layer, a hole injecting layer, or a hole transporting layer. The electronic device according to claim 6, wherein the organic electroluminescent device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), and an organic transistor (organic TFT). A compound represented by the following formula (1):
(1)

In the above formula (1)
₁₎ Ar 1 is selected from hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of the alkyl amine group, C ₁ ~ C alkyl thiophene group of _20, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of, C ₆ ~ C ₆₀ A C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group A C ₆ -C ₆₀ aryl group unsubstituted or substituted with one or more substituents; A halogen atom, 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 ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, N, S, at least one substituted or unsubstituted heteroaryl group of C ₅ ~ C ₆₀ having a one; 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy 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 cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ -C ₃₀ aryloxy group; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ 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 Lt;
2) L ₁ is C ₅ -C ₆₀ substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and amino group; Lt; / RTI >
3) L ₂ is C ₆ -C ₆₀ substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy and amino, An arylene group; A heteroaryl group of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₅ ~ C ₆₀ of; And a substituted or unsubstituted divalent aliphatic hydrocarbon. The compound according to claim 8, which is represented by the following formula (6):

Ar _1, L ₂ in Formula 6 is the same as Ar _1, L ₂ in Formula (1). 9. A compound according to claim 8, characterized in that it is selected from the following compounds:

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