KR20190012246A - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention provides a new compound for an organic electronic element which is capable of improving light emitting efficiency, stability, and life of the element; an organic electronic element including the same; and an electronic device thereof. According to the present invention, the organic electronic element is formed by stacking a first electrode, one or more organic material layers, and a second electrode in such order.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound for an organic electronic device, an organic electronic device including the compound,

The present invention relates to a novel compound for an organic electric device, an organic electric device including the same, and an electronic device therefor.

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 high luminous efficiency, low driving voltage, color purity, and service life of the device, and an organic electronic device using the novel compound and an electronic device thereof.

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) R ₁ and R ₂ are hydrogen ; Deuterium ; Tritium ; A halogen group ; A nitro group; A nitrile group; Amide group; A silane group; A condensed ring group of a C ₆ to C ₆₀ aromatic ring and a C ₄ to C ₆₀ aliphatic ring;

Of hydrogen, deuterium, halogen group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₁ ~ C ₆₀ aryl amine group, C ₁ ~ C ₆₀ of An alkylthio group, an alkylthiophene group, a C ₆ to C ₆₀ arylthiophene group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl A C ₆ to C ₆₀ aryl group substituted with deuterium, a C ₈ to C ₆₀ arylalkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and an aryl group, a substituted or unsubstituted substituted or unsubstituted by at least one group selected from the group consisting of a heterocyclic ring of the ring _{C 2 ~ C 60 C 6 ~} C 60;

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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ arylalkyl groups, _{~ C 20, C 8 ~ C} 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, optionally substituted from the group consisting of nitrile group, and an acetylene with one or more substituents selected or unsubstituted C ₁ ~ C ₅₀ An alkyl group ;

Hydrogen, deuterium, halogen, CN, NO _2, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₆ ~ C ₆₀ aryl amine group, C ₁ A C ₆ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, a 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 substituted or unsubstituted from the group consisting of a heterocycle of the C ₂ ~ C ₆₀ ring A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with one or more selected groups and contains at least one hetero atom selected from O, N, and S ; And

An amine group substituted or unsubstituted with at least one group selected from the group consisting of a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₆ to C ₆₀ aryl group, and a C ₈ to C ₆₀ aryl alkenyl group ; ≪ / RTI >

(2) Ar ₁ to Ar ₈ may be the same or different

A halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkylthiophene A C ₂ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ arylthio group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, Substituted with at least one substituent selected from the group consisting of a C ₆ to C ₂₀ aryl group substituted with a halogen atom, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group Or an unsubstituted C ₆ to C ₆₀ aryl group ;

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 ₆ 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 substituted or unsubstituted C ₆ -C ₂₀ aryl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with at least one substituent and contains at least one heteroatom selected from O, N and S;

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, A substituted or unsubstituted C ₁ to C ₃₀ substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₆ to C ₂₀ aryl group, and a substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group An 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, a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₆₀ with one or more substituents selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₆ ~ C ₃₀ substituted by deuterium An aryloxy group ;

A cycloalkyl group of a halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of, C ₆ ~ C of a ₆₀ aryl group, C ₂ ~ C ₆₀ with one or more substituents selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group; And

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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ 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 ; ≪ / RTI >

(3) R ₁ , R ₂ , Ar ₁ to Ar ₈ may combine with or react with neighboring groups to form a saturated or unsaturated ring. Here, the unsaturated ring includes an alicyclic group and an aromatic ring, as well as a heterocyclic ring. Each of Ar ₁ to Ar _{8 may} be bonded to or reacted with a neighboring group to form a saturated or unsaturated aliphatic ring, an aromatic ring, a heterocyclic ring, a spiro compound, or the like.

At this time, 'adjacent period' includes not only the substituent attached to the mother nucleus but also the mother nucleus itself. Thus, each of R ₁ , R ₂ , and Ar ₁ to Ar ₈ may be bonded to or react with neighboring substituents, functional groups, or carbon contained in the parent moiety or carbon of the parent moiety to form a saturated or unsaturated ring have. The ring formed may be an aromatic, alicyclic, heterocyclic, spiro compound, or the like.

(4) a and b are integers of 1 to 4, and when a and b are two or more, plural R ₁ and R ₂ may be the same or different.

In the present specification, the term "aryl group" means a single ring or a heterocyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction.

The term "heterocyclic group" refers to an aromatic or alicyclic monocyclic or heterocyclic ring containing a heteroatom in place of the ring forming carbon, and the adjacent substituent is a hetero Aromatic or alicyclic ring.

In order to solve the above problems of the prior art and to achieve the object of the present invention of improving the luminous efficiency, the driving voltage, the color purity, the stability and the lifetime of the device, the present invention provides a compound .

In the formula (2) to (4), Ar ₁ to Ar ₈ are the same as Ar ₁ ~ Ar ₈ of formula (1), R ₁ to R ₆ are the same as R ₁ and R _2, a to f will And is an integer of 1 to 4.

More specifically, the above Chemical Formulas 1 to 4 may be one of the following compounds.

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

The compounds represented by the above formulas (1) to (4) may be one of the compounds shown in the above formulas (1-1) to (4-17), but are not limited thereto. Here, the substituents of the compounds represented by formulas (1) to (4) are exemplified as typical compounds since it is practically difficult to exemplify all compounds in a wide range of relation. However, 4 may also form part of this specification.

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 synthetic methods for compounds of formulas (1) and (2)

General synthetic methods for compounds of formulas 3 and 4

General synthesis method of Sub material

Hereinafter, a method for synthesizing intermediates A to D used in the synthesis of Formulas 1 to 4 will be described in an exemplary manner.

Example of synthesis of intermediate A

Synthesis of 3,5-dibromo-N, N-diphenylaniline

250mL 1,3,5-tribromobenzene (18.6 g, 59.1 mmol), diphenylamine (10 g, 59.1 mmol), Pd 2 (dba) 3 (1.6 g, 1.77 mmol), P (t-Bu) To a round bottom flask was added ₃ (3.6 g, 17.73 mmol), NaOtBu (14.2 g, 147.8 mmol) and Toluene (150 mL) were added in this order, followed by reaction at room temperature for 30 minutes. 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 to obtain 13.1 g (54.9%) of product.

The sum of N- (3,5-dibromophenyl) -N- (naphthalen-1-yl) naphthalen- castle

(37.2 g, 118.2 mmol), dinaphthalen-1-ylamine (20 g, 118.2 mmol), Pd ₂ (dba) ₃ (7.2 g, 3.54 mmol), P -Bu) ₃ (7.2 g, 35.46 mmol), NaOtBu (28.4 g, 295.6 mmol) and Toluene (300 mL) were added in this order and the reaction was allowed to proceed at room temperature for 30 minutes. 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 silicagel column to obtain 26.2 g (54.9%) of product.

Synthesis of 3,5-dibromo-N, N-di-p-tolylaniline

A 250mL round bottom flask was added di- p -tolylamine (15 g, 76.03 mmol), 1,3,5-tribromobenzene (23.9 g, 76.03 mmol), Pd 2 (dba) 3 (2.09 g, 2.28 mmol), P (t -Bu) ₃ (4.6 g, 22.8 mmol), NaOtBu (18.3 g, 190.1 mmol) and Toluene (200 mL) were added in this order and the reaction was allowed to proceed at room temperature for 30 minutes. 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 silica gel column chromatography to obtain 13.5 g (41.1%) of product.

Synthesis of intermediate B

Synthesis of 5,5'-dibromo-N3, N3, N3 ', N3'-tetraphenylbiphenyl-3,3'-diamine (B-1)

Ether (150 mL) and 3,5-dibromo-N, N-diphenylaniline (13.1 g, 32.5 mmol) were added to a 250 mL round-bottomed flask and the mixture was cooled to -78 ° C and n-BuLi 2.5M in hexane (14.3 mL, mmol) is slowly added dropwise. The mixture was stirred at -78 ° C for about 1 hour, and CuCl ₂ (4.8 g, 35.75 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was silicagel column to obtain 14 g (66.6%) of product.

5,5'-dibromo-N3, N3, N3'-tri (naphthalen-1-yl) -N3'- (naphthalen-2-yl) - [1,1'-biphenyl] -3,3'-diamine B-2)

Naphthalen-2-yl) naphthalen-2-amine (26.2 g, 52.1 mmol) was added to a 500 mL round bottom flask, and ether (350 mL) , And then n-BuLi 2.5M in hexane (22.9 mL, 57.31 mmol) was slowly added dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (7.7 g, 57.31 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silica gel column chromatography to obtain 26.8 g (60.7%) of the product.

Synthesis of 5,5'-dibromo-N3, N3, N3 ', N3'-tetra (naphthalen-2-yl) biphenyl-3,3'-diamine (B-3)

Naphthalen-2-yl) naphthalen-2-amine (26.2 g, 52.1 mmol) was added to a 500 mL round bottom flask, and ether (300 mL) , And then n-BuLi 2.5M in hexane (22.9 mL, 57.31 mmol) was slowly added dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (7.7 g, 57.31 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 25.8 g (58.5%) of product.

Synthesis of 5,5'-dibromo-N3, N3, N3 ', N3'-tetrap-tolylbiphenyl-3,3'-diamine (B-4)

Ether (150 mL) and 3,5-dibromo-N, N-di-p-tolylaniline (13.5 g, 31.3 mmol) were placed in a 250 mL round-bottomed flask, cooled to -78 ° C and n-BuLi 2.5M in hexane (13.8 mL, 34.4 mmol) is slowly added dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (4.6 g, 34.4 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was silicagel column to obtain 12.8 g (58.2%) of product.

Synthesis of intermediate C

Synthesis of 2,4-dibromo-9-phenyl-9H-carbazole

(5.0 g, 15.38 mmol), iodobenzene (3.14 g, 15.38 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol), P (t-Bu ) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 to obtain 5.2 g (84.3%) of the product.

Synthesis of 2,4-dibromo-9- (naphthalen-1-yl) -9H-carbazole

Iodonaphthalene (3.91 g, 15.38 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol) and P (t) were added to a 100 mL round bottom flask. -Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 to obtain 5.4 g (77.7%) of product.

Synthesis of 2,4-dibromo-9- (naphthalen-2-yl) -9H-carbazole

(5.0 g, 15.38 mmol), 2-iodonaphthalene (3.91 g, 15.38 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol) and P -Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 to obtain 5.2 g (77.3%) of product.

Synthesis of 2,4-dibromo-9- (p-tolyl) -9H-carbazole

4-methylbenzene (3.35 g, 15.38 mmol) and Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol) were added to a 100 mL round bottom flask, , P (t-Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 silica gel column chromatography to obtain 4.9 g (76.7%) of product.

Synthesis of 9 - ([1,1'-biphenyl] -4-yl) -2,4-dibromo-9H-carbazole

To a 100 mL round bottom flask was added 2,4-dibromo-9H-carbazole (5.0 g, 15.38 mmol), 4-iodobiphenyl (4.31 g, 15.38 mmol), Pd ₂ (dba) ₃ (0.42 g, -Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 to obtain 5.1 g (69.5%) of product.

Synthesis of 2,4-dibromo-9- (4-phenylnaphthalen-1-yl) -9H-carbazole

(5.0 g, 15.38 mmol), 1-iodo-4-phenylnaphthalene (5.1 g, 15.38 mmol) and Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol) in a 100 mL round- , P (t-Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 silica gel column chromatography to obtain 5.4 g (67.6%) of product.

Synthesis of 2,4-dibromo-9-5D-phenyl-9H-carbazole

Dibromo-9H-carbazole (5.0 g, 15.38 mmol), iodobenzene-D5 (3.22 g, 15.38 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.46 mmol), P -Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) were added in this order and the reaction was carried out at 80 ° C for 2 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 silicagel column to obtain 4.2 g (67.2%) of product.

Synthesis of 9 - ([1,1'-5D-biphenyl] -4-yl) -2,4-dibromo-9H-carbazole

2,4-dibromo-9H-carbazole (5.0 g, 15.38 mmol), 4'-iodo-2,3,4,5,6-d5-biphenyl (4.39 g, 15.38 mmol), Pd _{2 (dba) 3 (0.42 g,} 0.46 mmol), P (t-Bu) 3 (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol), Toluene (50 mL) after the insert in order at 80 ˚C The reaction proceeds for 2 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 silicagel column to obtain 3.7 g (70.5%) of product.

Synthesis of 2,4-dibromo-9- (5D-4-phenylnaphthalen-1-yl) -9H-carbazole

100mL round bottom flask, 2,4-dibromo-9H-carbazole ( 5.0 g, 15.38 mmol), 1-iodo-4-phenyl-d5-naphthalene (5.16 g, 15.38 mmol), Pd 2 (dba) 3 (0.42 g , 0.46 mmol), P (t-Bu) ₃ (0.94 g, 4.62 mmol), NaOtBu (3.7 g, 38.45 mmol) and Toluene (50 mL) . 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 to obtain 5.3 g (64.7%) of product.

Synthesis of Intermediate D

Synthesis of 2,2'-dibromo-9,9'-diphenyl-9H, 9'H-4,4'-bicarbazole (D-1)

Ether (150 mL) and 2,4-dibromo-9-phenyl-9H-carbazole (12 g, 29.9 mmol) were placed in a 250 mL round-bottomed flask, cooled to -78 ° C and n-BuLi 2.5M in hexane mL, 32.9 mmol) was slowly added dropwise. The mixture was stirred at -78 ° C for 1 hour, and CuCl ₂ (4.4 g, 32.9 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 13.2 g (68.7%) of product.

Synthesis of 2,2'-dibromo-9,9'-di (naphthalen-1-yl) -9H, 9'H-4,4'-bicarbazole (D-2)

Ether (150 mL) and 2,4-dibromo-9- (naphthalen-1-yl) -9H-carbazole (18 g, 39.9 mmol) were added to a 250 mL round bottom flask, M In hexane (17.6 mL, 43.9 mmol) was slowly added dropwise at -78 ° C, and CuCl ₂ (5.9 g, 43.9 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours After the reaction was completed, the reaction mixture was extracted with ethyl acetate and brine, dried over MgSO ₄ , and the obtained organic layer was subjected to silica gel column chromatography to obtain 18.9 g (63.8%) of product.

Synthesis of 2,2'-dibromo-9,9'-di (naphthalen-2-yl) -9H, 9'H-4,4'-bicarbazole (D-3)

Ether (150 mL) and 2,4-dibromo-9- (naphthalen-2-yl) -9H-carbazole (18 g, 39.9 mmol) were added to a 250 mL round bottom flask, M In hexane (17.6 mL, 43.9 mmol) was slowly added dropwise at -78 ° C, and CuCl ₂ (5.9 g, 43.9 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours After completion of the reaction, the reaction mixture was extracted with ethyl acetate and brine, and the organic layer was dried over MgSO ₄ , and the obtained organic layer was subjected to silicagel column to obtain 18.4 g (62.1%) of product.

Synthesis of 2,2'-dibromo-9,9'-di-p-tolyl-9H, 9'H-4,4'-bicarbazole (D-4)

Ether (150 mL) and 2,4-dibromo-9- (p-tolyl) -9H-carbazole (12 g, 29.9 mmol) were placed in a 250 mL round bottom flask, cooled to -78 ° C, in hexane (13.16 mL, 32.9 mmol) is slowly added dropwise. The mixture was stirred at -78 ° C for 1 hour, and CuCl ₂ (4.4 g, 32.9 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 12.9 g (64.3%) of product.

Synthesis of 9,9'-di (biphenyl-4-yl) -2,2'-dibromo-9H, 9'H-4,4'-bicarbazole (D-5)

To a 250 mL round bottom flask was added ether (150 mL), 9,9'-di (biphenyl-4-yl) -2,2'-dibromo-9H, 9'H-4,4'- bicarbazole (15 g, 31.43 mmol ), Cool to -78 ° C, and add n-BuLi 2.5M in hexane (13.8 mL, 34.58 mmol) dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (4.65 g, 34.58 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 15.7 g (62.9%) of product.

Synthesis of 2,2'-dibromo-9,9'-bis (4-phenylnaphthalen-1-yl) -9H, 9'H-4,4'-bicarbazole (D-6)

Ether (150 mL) and 2,4-dibromo-9- (4-phenylnaphthalen-1-yl) -9H-carbazole (15 g, 28.5 mmol) were added to a 250 mL round bottom flask, -BuLi 2.5 M in hexane (12.5 mL, 31.3 mmol) is slowly added dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (4.2 g, 31.3 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 15.2 g (59.6%) of product.

Synthesis of 2,2'-dibromo-9,9'-D5-diphenyl-9H, 9'H-4,4'-bicarbazole (D-7)

Ether (150 mL) and 2,4-dibromo-9-D5-phenyl-9H-carbazole (15 g, 36.93 mmol) were added to a 250 mL round bottom flask. The reaction mixture was cooled to -78 ° C and n-BuLi 2.5M in hexane (16.24 mL, 40.6 mmol) is slowly added dropwise. The mixture was stirred at -78 ° C for 1 hour, and CuCl ₂ (5.5 g, 40.6 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silica gel column chromatography to obtain 14.9 g (61.7%) of the product

Synthesis of 9,9'-di (D5-biphenyl-4-yl) -2,2'-dibromo-9H, 9'H-4,4'-bicarbazole (D-8)

Ether (150 mL) and 2,4-dibromo-9- (4-D5-phenylnaphthalen-1-yl) -9H-carbazole (15 g, 28.2 mmol) were added to a 250 mL round bottom flask, Then add n-BuLi 2.5M in hexane (12.4 mL, 31 mmol) slowly dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (4.2 g, 31 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silicagel column to obtain 15.4 g (60.4%) of the product.

Synthesis of 2,2'-dibromo-9,9'-bis (4-D5-phenylnaphthalen-1-yl) -9H, 9'H-4,4'-bicarbazole

Ether (150 mL) and 2,4-dibromo-9-D5-phenyl-9H-carbazole (15 g, 31.1 mmol) were added to a 250 mL round-bottomed flask. The mixture was cooled to -78 ° C and n-BuLi 2.5M in hexane (13.7 mL, 34.2 mmol) was slowly added dropwise. The mixture was stirred at -78 캜 for about 1 hour, and CuCl ₂ (4.6 g, 34.2 mmol) was added thereto, followed by stirring for 5 hours and stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture is extracted with ethyl acetate and brine, and the organic layer is dried with MgSO ₄ . The obtained organic layer was subjected to silica gel column chromatography to obtain 14.7 g (58.7%) of product.

The results of mass spectrometry for B-1 to B-4 among the intermediates obtained through the above synthesis are shown in Table 1 below, and D-1 to D-9 are shown in Table 2 below.

Example of final compound synthesis:

Intermediate (1 equivalent), sub material (2.5 _{eq), Pd (PPh 3) 4} (0.06 equiv.), NaOH (6 equiv.), THF (4 mL / 1mmol ), water (2 / mmol) in a round bottom flask, the The mixture is heated to 80 ° C and refluxed. When the reaction is complete, dilute with distilled water at room temperature, extract using ethyl acetate and brine, and dry the organic layer with MgSO ₄ . The resulting organic layer was concentrated, and the resulting product was purified by silicagel column and recrystallization. The product was identified by FD-MS as shown in the table below.

The results of the mass spectrometry of the final compounds obtained through the above synthesis are shown in Table 3 below.

Meanwhile, the respective substituents of the compounds represented by the formulas (1) to (4) are broadly related to each other. However, the compounds represented by the formulas (1) to (4), which are not exemplarily shown in the synthesis examples, And may form part of the specification.

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

An organic electroluminescent device was fabricated according to a conventional method using various compounds obtained through synthesis as a hole transport layer, respectively. First, a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the organic substrate as a hole injection layer to form a 10 nm thick film. Subsequently, the inventive compound and the comparative example were vacuum-deposited to a thickness of 20 nm as a hole transport layer. Vacuum deposition was carried out for comparative experiments. Thereafter, BD-052X (Idemitsu) was used as a luminescent dopant and 9,10-di- (naphthalene-2-anthracene) = AND] was used as a host material. The doping concentration was fixed at 4% Respectively. Subsequently, tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm as an electron injecting layer. Thereafter, LiF as a halogenated alkyl metal was deposited to a thickness of 0.2 nm, Al was subsequently deposited to a thickness of 150 nm, and the Al / LiF was used as a cathode to manufacture an organic electroluminescent device. Electroluminescence (EL) characteristics were measured by PR-650 of a photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices thus prepared and the comparative organic electroluminescent devices. As a result of measurement, the luminance was measured at a luminance of 300 cd / The T90 lifetime was measured using a life-time instrument manufactured by McAfee.

For comparison, an organic electroluminescent device having the same structure as that of the test example was manufactured using the compounds of? -NPD (Comparative Example-1), Comparative Example-2 and Comparative Example-3 which are widely known instead of the compound of the present invention as a hole transport layer Respectively.

The characteristics (driving voltage, current density, luminance, efficiency, lifetime, etc.) of the above-described compounds and organic electroluminescent devices prepared from the hole transporting layer materials of Comparative Examples 1 to 3 are shown in Table 4 below .

As can be seen from Table 4, in the present invention, most of the driving voltage was lowered by more than 1.5 V compared with the comparative example, and not only the driving voltage was lowered but also a remarkable long life Respectively.

That is, the organic electroluminescent device using the material for the organic electroluminescent device of the present invention can be used as a light emitting host and a hole transporting material, thereby remarkably improving the low driving voltage, color purity, high luminous efficiency and lifetime.

It is apparent 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 (9)

A first electrode;
One or more organic layers including a compound represented by the following formula (1); And
And a second electrode are stacked in this order.

In Formula 1,
(1) R ₁ and R ₂ are hydrogen ; Deuterium ; Tritium ; A halogen group ; A nitro group; A nitrile group; Amide group; A silane group; A condensed ring group of a C ₆ to C ₆₀ aromatic ring and a C ₄ to C ₆₀ aliphatic ring;
Of hydrogen, deuterium, halogen group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₁ ~ C ₆₀ aryl amine group, C ₁ ~ C ₆₀ of An alkylthio group, an alkylthiophene group, a C ₆ to C ₆₀ arylthiophene group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl A C ₆ to C ₆₀ aryl group substituted with deuterium, a C ₈ to C ₆₀ arylalkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and an aryl group, a substituted or unsubstituted substituted or unsubstituted by at least one group selected from the group consisting of a heterocyclic ring of the ring _{C 2 ~ C 60 C 6 ~} C 60;
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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ arylalkyl groups, _{~ C 20, C 8 ~ C} 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, optionally substituted from the group consisting of nitrile group, and an acetylene with one or more substituents selected or unsubstituted C ₁ ~ C ₅₀ An alkyl group ;
Hydrogen, deuterium, halogen, CN, NO _2, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₁ ~ C ₆₀ aryl amine group, C ₁ A C ₆ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, a 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 substituted or unsubstituted from the group consisting of a heterocycle of the C ₂ ~ C ₆₀ ring A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with one or more selected groups and contains at least one hetero atom selected from O, N and S as a hetero atom ; And
An amine group substituted or unsubstituted with at least one group selected from the group consisting of a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₆ to C ₆₀ aryl group, and a C ₈ to C ₆₀ aryl alkenyl group ; ≪ / RTI >
(2) Ar ₁ to Ar ₈ may be the same or different
A halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkylthiophene A C ₂ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ arylthio group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, Substituted with at least one substituent selected from the group consisting of a C ₆ to C ₂₀ aryl group substituted with a halogen atom, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group Or an unsubstituted C ₆ to C ₆₀ aryl group ;
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 substituted or unsubstituted C ₆ -C ₂₀ aryl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with at least one substituent and contains at least one heteroatom selected from O, N and S;
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, A substituted or unsubstituted C ₁ to C ₃₀ substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₆ to C ₂₀ aryl group, and a substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group An 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, a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group yirwojin group heterocyclic C ₆ ~ C ₃₀ substituted by deuterium An aryloxy group ;
A cycloalkyl group of a halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of, C ₆ ~ C of a ₆₀ aryl group, C ₂ ~ C ₆₀ with one or more substituents selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group; And
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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ 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 ; , ≪ / RTI >
(3) a and b are integers of 1 to 4, and when a and b are two or more, plural R ₁ and R ₂ may be the same or different. The method according to claim 1,
Wherein the formula (1) is one of the following compounds.

The method according to claim 1,
Characterized in that said compound is formed into said organic material layer by a soluble process. The method according to claim 1,
Wherein the organic material layer is at least one of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, and an electron transporting layer. 5. The method of claim 4,
Wherein the compound is used as a host material of the light emitting layer. The method of claim 3,
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). An electronic device comprising the organic electroluminescent device of claim 6. A compound represented by the following formula (1).

In Formula 1,
(1) R ₁ and R ₂ are hydrogen ; Deuterium ; Tritium ; A halogen group ; A nitro group; A nitrile group; Amide group; A silane group; A condensed ring group of a C ₆ to C ₆₀ aromatic ring and a C ₄ to C ₆₀ aliphatic ring;
Of hydrogen, deuterium, halogen group, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₁ ~ C ₆₀ aryl amine group, C ₁ ~ C ₆₀ of An alkylthio group, an alkylthiophene group, a C ₆ to C ₆₀ arylthiophene group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl A C ₆ to C ₆₀ aryl group substituted with deuterium, a C ₈ to C ₆₀ arylalkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and an aryl group, a substituted or unsubstituted substituted or unsubstituted by at least one group selected from the group consisting of a heterocyclic ring _{C 2 ~ C 60 C 6 ~} C 60;
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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ arylalkyl groups, _{~ C 20, C 8 ~ C} 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, optionally substituted from the group consisting of nitrile group, and an acetylene with one or more substituents selected or unsubstituted C ₁ ~ C ₅₀ An alkyl group ;
Hydrogen, deuterium, halogen, CN, NO _2, C ₁ ~ C ₆₀ alkyl group, C ₁ ~ C ₆₀ alkoxy group, C ₁ ~ C ₆₀ alkyl amine group, C ₁ ~ C ₆₀ aryl amine group, C ₁ A C ₆ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, a 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 substituted or unsubstituted from the group consisting of a heterocycle of the C ₂ ~ C ₆₀ ring A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with one or more selected groups and contains at least one hetero atom selected from O, N and S as a hetero atom ; And
An amine group substituted or unsubstituted with at least one group selected from the group consisting of a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₆ to C ₆₀ aryl group, and a C ₈ to C ₆₀ aryl alkenyl group ; ≪ / RTI >
(2) Ar ₁ to Ar ₈ may be the same or different
A halogen atom, a halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkylthiophene A C ₂ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ arylthio group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, Substituted with at least one substituent selected from the group consisting of a C ₆ to C ₂₀ aryl group substituted with a halogen atom, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group Or an unsubstituted C ₆ to C ₆₀ aryl group ;
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 substituted or unsubstituted C ₆ -C ₂₀ aryl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, A C ₂ to C ₆₀ heterocyclic group which is substituted or unsubstituted with at least one substituent and contains at least one heteroatom selected from O, N and S;
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, A substituted or unsubstituted C ₁ to C ₃₀ substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₆ to C ₂₀ aryl group, and a substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group An 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, a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group yirwojin group heterocyclic C ₆ ~ C ₃₀ substituted by deuterium An aryloxy group ;
A cycloalkyl group of a halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of, C ₆ ~ C of a ₆₀ aryl group, C ₂ ~ C ₆₀ with one or more substituents selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group; And
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 ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with deuterium, C ₇ alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ 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 ; , ≪ / RTI >
(3) a and b are integers of 1 to 4, and when a and b are two or more, plural R ₁ and R ₂ may be the same or different. 9. The method of claim 8,
Wherein said formula (1) is one of the following compounds.

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