KR101670904B1 - Imidazole derivative and organic electroluminescent device including the same - Google Patents

Abstract

[상기 화학식 1에서 각 치환기들의 정의는 발명의 상세한 설명에서 정의한 바와 같다.]There is provided an imidazole derivative represented by the following formula (1).
[Chemical Formula 1]

[Wherein the definition of each substituent in Formula 1 is as defined in the description of the invention]

Description

The present invention relates to an imidazole derivative and an organic electroluminescent device including the same,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an imidazole derivative and an organic electroluminescent device including the same. More particularly, the present invention relates to an organic electroluminescent device having high luminous efficiency and a novel imidazole derivative for the same.

An organic electroluminescent device refers to a self-emitting organic material that emits light when a current flows through a fluorescent organic compound, and is also referred to as an organic light emitting diode (OLED).

OLEDs can be made much thinner because they do not require a separate light source and can be formed on a flexible transparent substrate such as a plastic as well as on a plasma display panel or an inorganic electroluminescence It can be driven at a voltage as low as 10V or less, completely expresses natural colors with very low power consumption, emits light in all directions, has wide viewing angle, and the response speed of pixels is also very fast, Can be displayed. In addition, it has a merit that manufacturing process is simple compared with other displays and its production cost is low, and thus it is attracting attention as the most promising next generation flat panel display.

This OLED was first attempted in 1963 by Pope et al. To study the carrier injection type electroluminescence (EL) using an anthracene aromatic hydrocarbon single crystal. From these studies, it was found that charge injection, recombination, exciton generation, And the basic mechanism of electroluminescence and electroluminescence characteristics.

In addition, after Tang and Van Slyke in 1987 reported the characteristics of high efficiency using a multilayer thin film structure of organic electroluminescent devices [Tang, C. W., Van Slyke, S. A. Appl. Phys. Lett. 51, 913 (1987)], OLEDs have a high potential for use in LCD backlighting and illumination as well as excellent characteristics as a next generation display, and many studies have been conducted under the spotlight [Kido, J., Kimura, M., and Nagai, K., Science 267,1332 (1995)]. Especially, in order to increase the luminous efficiency, various approaches such as structural change and material development have been performed [Sun, S., Forrest, S. R., Appl. Phys. Lett. 91, 263503 (2007) / Ken-Tsung Wong, Org. Lett., 7, 2005, 5361-5364].

The basic structure of an OLED display generally includes an anode, a hole injection layer (HIL), a hole transporting layer (HTL), an emission layer (EML), an electron transporting layer (ETL) ), And a cathode (cathode), and the electron-emitting organic multi-layer film has a sandwich structure formed between both electrodes. When a voltage is applied between both electrodes in this structure, holes are injected into the anode and electrons from the cathode are injected into the organic layer. When excited holes and electrons meet, an excition is formed. And emits light of a color corresponding to the energy band gap of the light emitting layer in the course of conversion into light energy. At this time. The color of the light varies depending on the organic material constituting the light emitting layer. In the case of using only the light emitting material, there is a problem that the color purity and the light emitting efficiency are less than the intermolecular interaction. Therefore, the host / dopant ) Structure.

As for the blue color of the three primary colors of the luminescent material, 4,4'-bis (2,2-diphenylvinyl) -1,1'-biphenyl (DPVBi) and TBSA series materials have been developed. Particularly, in the case of idemitsu- Distyryl compounds are known to exhibit good performance.

However, the blue light emitting material can not secure a sufficient lifetime due to problems such as color purity and efficiency, long-term thermal stability, and the materials used in practical commercial products are extremely limited, so development of materials is continuously required.

Korea Patent Publication No. 2014-0009095

The object of the present invention is to provide a novel imidazole derivative excellent in luminous efficiency and durability as compared with conventional materials, and that the imidazole derivative is contained in an organic film to provide a high luminous efficiency and a long lifetime And to provide an organic electroluminescent device.

According to one aspect of the present invention, an imidazole derivative represented by the following formula (1) is provided.

[Chemical Formula 1]

[In Formula 1 A is aryl substituted or unsubstituted C ₆ ~ C _30, substituted or non-substituted or heteroaryl-substituted C ₅ ~ C _30, or a substituted or unsubstituted alkyl of the unsubstituted C ₁ ~ C _30, A substituted or unsubstituted C ₃ to C ₃₀ cycloalkyl, a substituted or unsubstituted C ₁ to C ₁₀ alkoxy,

p is 1 or 2,

L is a single bond,

q is 0 or 1.]

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the imidazole derivative.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic film disposed between the electrodes, wherein the organic film comprises the imidazole derivative .

According to still another aspect of the present invention, the imidazole derivative is selected from the group consisting of an electron blocking layer, an electron transporting layer, an electron injecting layer, a functional layer having both an electron transporting function and an electron injecting function, The organic electroluminescent device is characterized in that it is contained in any one layer.

The imidazole derivative according to an embodiment of the present invention may be included in the organic layer of the organic electroluminescent device to lower the driving voltage of the device, improve the luminous efficiency, and prolong the lifetime.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a graph showing EL peaks of the organic electroluminescent devices manufactured in the comparative test examples and Test Examples 1 and 2. Fig.

As used herein, the term "aryl " means a polyunsaturated aromatic hydrocarbon substituent, which may be a single ring or a multiple ring (1 to 3 rings) fused or covalently bonded unless otherwise specified.

The term "heteroaryl" means an aryl group (or a ring) comprising one to four heteroatoms selected from N, O and S (in each case on a separate ring in the case of multiple rings) Optionally oxidized, and the nitrogen atom (s) are quaternized, as the case may be. Heteroaryl groups can be attached to the remainder of the molecule through carbon or heteroatoms.

The aryl includes a single or fused ring system, suitably containing from 4 to 7, preferably 5 or 6, ring atoms in each ring. Also included are structures in which one or more aryls are attached through a chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, But are not limited thereto.

The heteroaryl includes 5- to 6-membered monocyclic heteroaryl and polycyclic heteroaryl fused with one or more benzene rings, and may be partially saturated. Also included are structures in which one or more heteroaryls are attached via a chemical bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt.

Specific examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl such as pyridyl, pyridyl, pyrazinyl, pyridazinyl and the like, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl , Benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like, but are not limited thereto. But is not limited thereto.

"Substituted" in the expression " substituted or unsubstituted ", as used herein, means that at least one hydrogen atom in the hydrocarbon is each independently replaced with the same or different substituents. Useful substituents include, but are not limited to:

Such substituents include, but are not limited to, -F; -Cl; -Br; -CN; -NO ₂ ; -OH; A C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted by -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C ₁ -C ₂₀ alkoxy group unsubstituted or substituted by -F, -Cl, -Br, -CN, -NO ₂ or -OH; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO _2, or substituted by -OH or unsubstituted C ₆ ~ C ₃₀ aryl group; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 or -OH-substituted or unsubstituted C ₆ ~ C ₃₀ heteroaryl group, a; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted by -OH or unsubstituted C ₅ ~ C ₂₀ cycloalkyl group; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted or unsubstituted by -OH unsubstituted C ₅ ~ C ₃₀ heterocycloalkyl group; And a group represented by -N (G ₁ ) (G ₂ ). Wherein G ₁ and G ₂ are each independently selected from the group consisting of hydrogen; A C ₁ -C ₁₀ alkyl group; Or a C ₆ -C ₃₀ aryl group substituted or unsubstituted with a C ₁ -C ₁₀ alkyl group.

Hereinafter, the present invention will be described in detail.

An imidazole derivative according to an embodiment of the present invention may be represented by the following formula (1).

[Chemical Formula 1]

Wherein A is substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, substituted or unsubstituted C ₁ -C ₃₀ alkyl, or substituted Or unsubstituted C ₃ -C ₃₀ cycloalkyl, substituted or unsubstituted C ₁ -C ₁₀ alkoxy,

p is 1 or 2,

L is a single bond,

q is 0 or 1;

The compound represented by Formula 1 may be selected from among the structures represented by Formula 2 below.

(2)

In formula (1) or (2), A may be selected from among the structures listed in formula (3).

(3)

Specific examples of the compound represented by the formula (1) of the present invention include a compound represented by the following formula (4). However, the compounds represented by Formula 1 of the present invention are not limited to these compounds.

[Chemical Formula 4]

The imidazole derivative represented by the above formula (1) can be synthesized using a known organic synthesis method. The method for synthesizing the imidazole derivative can be easily recognized by those skilled in the art with reference to the following examples.

Also, according to the present invention, there is provided an organic electroluminescent device comprising an imidazole derivative represented by the above formula (1).

The imidazole derivative of Formula 1 is useful as a light emitting layer material, and can be used as a material for various layers of organic electroluminescent devices.

The organic electroluminescent device according to the present invention includes a first electrode, a second electrode, and at least one organic film disposed between the electrodes. The organic film contains at least one imidazole derivative represented by the above formula (1).

The organic layer includes a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, And at least one layer selected from the group consisting of functional layers having at the same time.

For example, the imidazole derivative may be contained in at least one selected from the group consisting of a light emitting layer, an organic layer disposed between the anode and the light emitting layer, and an organic layer disposed between the light emitting layer and the cathode. Preferably, the imidazole derivative may be contained in at least one layer selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, and a functional layer having both a hole injecting function and a hole transporting function. The imidazole derivative may be included in the organic film as a single substance or a combination of different substances. Alternatively, the imidazole derivative may be used in combination with a conventionally known compound such as a light emitting layer, a hole transporting layer, and a hole injecting layer.

The organic electroluminescent device according to the present invention can be applied to an organic electroluminescent device including a positive electrode / a light emitting layer / a cathode, a positive electrode / a hole injecting layer / a light emitting layer / a negative electrode, an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / / Light emitting layer / electron transporting layer / electron injecting layer / cathode structure. Alternatively, the organic electroluminescent device may include a functional layer / a light emitting layer / an electron transporting layer / a cathode having both an anode / hole injecting function and a hole transporting function, a functional layer / a light emitting layer / an electron transporting layer / Electron injecting layer / cathode structure, but the present invention is not limited thereto.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

The organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. For example, an anode is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and an organic film including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer is formed thereon And then depositing a material which can be used as a cathode thereon. In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic film, and a cathode material on a substrate.

Meanwhile, the organic layer may be prepared by a wet process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer by using various polymer materials instead of a vapor deposition method.

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

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Example]

Intermediate synthesis example  1: Synthesis of intermediate (1)

In a 500 ml two-necked flask, 5.0 g (0.024 mol) of 9,10-phenanthrenequinone, 5.8 g (0.026 mol) of 4-iodoaniline, ammonium acetate, 7.4 g (0.096 mol) of acetic acid and 350 mL of acetic acid were added thereto, followed by stirring. 2.5 ml (0.026 mol) of 3-pyridine carboxaldehyde was added thereto and stirred for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 8.9 g of a white solid compound (intermediate (1)) (yield: 74%).

Intermediate synthesis example  2: Synthesis of intermediate (2)

In a 500 ml two-necked flask, 5.0 g (0.024 mol) of 9,10-phenanthrenequinone, 5.8 g (0.026 mol) of 4-iodoaniline, ammonium acetate, 7.4 g (0.096 mol) of acetic acid and 350 mL of acetic acid were added thereto, followed by stirring. 2.5 ml (0.026 mol) of 4-pyridine carboxaldehyde was added thereto and stirred for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 8.4 g (yield: 70%) of a white solid compound (intermediate (2)).

Intermediate synthesis example  3: Synthesis of intermediate (3)

5.0 g (0.024 mol) of 9,10-phenanthrenequinone, 7.4 g (0.096 mol) of ammonium acetate and 350 mL of acetic acid were placed in a 500 ml two-necked flask 2.5 ml (0.026 mol) of 3-pyridine carboxaldehyde and 3.1 ml (0.026 mol) of 3-iodoaniline were added thereto while stirring, and the mixture was stirred for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 7.2 g (yield: 60%) of a white solid compound (intermediate (3)).

Intermediate synthesis example  4: Synthesis of intermediate (4)

5.0 g (0.024 mol) of 9,10-phenanthrenequinone, 7.4 g (0.096 mol) of ammonium acetate and 350 mL of acetic acid were placed in a 500 ml two-necked flask 2.5 ml (0.026 mol) of 4-pyridine carboxaldehyde and 3.1 ml (0.026 mol) of 3-iodoaniline were added to the mixture while stirring, and the mixture was stirred for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 7.2 g (yield: 60%) of a white solid compound (intermediate (4)).

Intermediate synthesis example  5: Synthesis of intermediate (5)

5.0 g (0.024 mol) of benzyl, 7.4 g (0.096 mol) of ammonium acetate and 350 mL of acetic acid were added to a 500 ml two-necked flask and stirred with 4-pyridinecarboxaldehyde (4 (0.026 mol) of 3-iodoaniline and 3.1 ml (0.026 mol) of 3-iodoaniline were added to the mixture, followed by stirring for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 8.3 g (yield: 70%) of a white solid compound (Intermediate (5)).

Intermediate synthesis example  6: Synthesis of intermediate (6)

In a 500 ml two-necked flask, 5.0 g (0.024 mol) of benzyl, 5.7 g (0.026 mol) of 4-iodoaniline, 7.4 g (0.096 mol) of ammonium acetate, acid, and 2.5 ml (0.026 mol) of 3-pyridine carboxaldehyde were added thereto under stirring. The mixture was stirred under reflux for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 8.3 g (yield: 70%) of a white solid compound (intermediate (6)).

Example 1: Synthesis of compound (4-1)

The synthesis route of the compound (4-1) is shown below.

(1) (0.5 g, 1.005 mmol), benzothiophene d-carboline 0.3 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Then, the mixture was stirred at 120-130 for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.4 g (yield: 60%) of a white solid compound (4-1).

Example 2: Synthesis of compound (4-2)

The synthesis route of the compound (4-2) is shown below.

(1) (0.5 g, 1.005 mmol), benzo d-carboline 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10-phenanthrene Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.4 g (yield: 60%) of a white solid compound (4-2).

Example 3: Synthesis of compound (4-3)

The synthesis route of the compound (4-3) is shown below.

(1) (0.5 g, 1.005 mmol), imidazole d-carboline (0.4 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and dimethylformamide (DMF) , And the mixture was stirred at 120 to 130 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-3) (yield: 45%).

Example 4: Synthesis of compound (4-4)

The synthesis route of the compound (4-4) is shown below.

(1) (0.5 g, 1.005 mmol), b-carboline 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), and 1,10-phenanthroline Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 27 mg (yield: 5%) of a white solid compound (4-4).

Example 5: Synthesis of compound (4-5)

The synthesis route of the compound (4-5) is shown below.

(1) (0.5 g, 1.005 mmol), benzofuro d-carboline (0.3 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and dimethylformamide (DMF) , And the mixture was stirred at 120 to 130 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-5) (yield: 40%).

Example 6: Synthesis of compound (4-6)

The synthesis route of the compound (4-6) is shown below.

(1) (0.5 g, 1.005 mmol), a-carboline 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol) and 1,10-phenanthroline Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-6) (yield: 45%).

Example 7: Synthesis of compound (4-7)

The synthesis route of the compound (4-7) is shown below.

(1) (0.5 g, 1.005 mmol), 11-benzo d-carboline (0.2 g, 1.105 mmol) and CuI (24 mg, 0.126 mmol) A mixture of 45 mg (0.251 mmol) of 10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) After mixing, the mixture was stirred at 120 to 130 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-7) (yield: 30%).

Example 8: Synthesis of compound (4-8)

The synthesis route of the compound (4-8) is shown below.

(1) (0.5 g, 1.005 mmol), diphenylamino d-carboline (0.4 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Then, the mixture was stirred at 120 to 130 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-8) (yield: 45%).

Example 9: Synthesis of compound (4-9)

The synthesis route of the compound (4-9) is shown below.

(1) (0.5 g, 1.005 mmol), 7-t-butyl d-carboline (0.2 g, 1.105 mmol) and CuI (24 mg, 0.126 mmol ), 1,10-phenanthroline 45 mg (0.251 mmol), cesium carbonate (Cs ₂ CO ₃ ) 0.7 g (2.010 mmol) and dimethylformamide (DMF) 40 mL), and then stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-9) (yield: 40%).

Example 10: Synthesis of compound (4-10)

The synthesis route of the compound (4-10) is shown below.

(1) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of d-carboline, 24 mg (0.126 mmol) of CuI and 1,10-phenanthroline Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-10) (yield: 40%).

Example  11: Synthesis of compound (4-11)

The synthesis route of the compound (4-11) is shown below.

In 1 100 mL flask, intermediate (1) (0.5 g, 1.005 mmol), imidazole borate (imidazole borate) (0.4 g, 1.105 mmol), Pd (PPh 3) 4 35 mg (0.030 mmol), toluene (40 mL (20 mL) and K ₂ CO ₃ 0.2 g (1.508 mmol) / H ₂ O (20 mL) were added to the solution, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and purified by silica gel column chromatography to obtain 0.3 g (yield: 50%) of a white solid compound (4-11) ≪ / RTI >

Example 12: Synthesis of compound (4-12)

The synthesis route of the compound (4-12) is shown below.

Intermediate 1 to obtain 100 mL flask (1) (0.5 g, 1.005 mmol), triphenyl borate-4-amine (triphenylamine 4-borate) (0.4 g, 1.105 mmol), Pd (PPh 3) 4 35 mg (0.030 mmol (20 mL) and K ₂ CO ₃ (0.25 g, 1.508 mmol) / H ₂ O (20 mL) were added to the solution, and the mixture was stirred under reflux for 6 Lt; / RTI > After the reaction was completed, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and purified by silica gel column chromatography to obtain 0.3 g (yield: 50%) of a white solid compound (4-12) ≪ / RTI >

Example 13: Synthesis of compound (4-13)

The synthesis route of the compound (4-13) is shown below.

(1) (0.5 g, 1.005 mmol), carbazole 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10-phenanthroline phenanthroline (45 mg, 0.251 mmol), cesium carbonate (Cs ₂ CO ₃ ) (0.7 g, 2.010 mmol) and dimethylformamide (DMF) Lt; / RTI > After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-13) (yield: 60%).

Example 14: Synthesis of compound (4-14)

The synthesis route of the compound (4-14) is shown below.

(1) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of 4- (phenylamino) benzonitrile, 24 mg (0.126 mmol) of CuI, , 45 mg (0.251 mmol) of 10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-14) (yield: 35%).

Example 15: Synthesis of compound (4-15)

The synthesis route of the compound (4-15) is shown below.

(1) (0.5 g, 1.005 mmol), diphenylamine 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10-phenanthroline was mixed with 45 mg (0.251 mmol) of phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Stir for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.1 g (yield: 20%) of a white solid compound (4-15).

Example 16: Synthesis of compound (4-16)

The synthesis route of the compound (4-16) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), benzo d-carboline 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol) Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.4 g (yield: 60%) of a white solid compound (4-16).

Example 17: Synthesis of compound (4-17)

The synthesis route of the compound (4-17) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), benzothiophene d-carboline 0.3 g (1.105 mmol), CuI 24 mg (0.126 mmol) Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Then, the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 30%) of a white solid compound (4-17).

Example 18: Synthesis of compound (4-18)

The synthesis route of the compound (4-18) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), benzofuro d-carboline 0.3 g (1.105 mmol), CuI 24 mg (0.126 mmol) Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and dimethylformamide (DMF) , And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-18) (yield: 35%).

Example 19: Synthesis of compound (4-19)

The synthesis route of the compound (4-19) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of d-carboline, 24 mg (0.126 mmol) CuI, Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 40%) of a white solid compound (1-19).

Example  20: Synthesis of compound (4-20)

The synthesis route of the compound (4-20) is shown below.

(0.5 g, 1.005 mmol), diphenylamino d-carboline (0.4 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Then, the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-20) (yield: 45%).

Example 21: Synthesis of compound (4-21)

The synthesis route of the compound (4-21) is shown below.

(0.5 g, 1.005 mmol), 11-benzo d-carboline (0.2 g, 1.105 mmol), CuI (24 mg, 0.126 mmol) A mixture of 45 mg (0.251 mmol) of 10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) After mixing, the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-21) (yield: 30%).

Example 22: Synthesis of compound (4-22)

The synthesis route of the compound (4-22) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), a-carboline 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10-phenanthroline Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 40%) of a white solid compound (4-22).

Example 23: Synthesis of compound (4-23)

The synthesis route of the compound (4-23) is shown below.

(0.5 g, 1.005 mmol), imidazole d-carboline (0.4 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and dimethylformamide (DMF) , And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.4 g (yield: 50%) of a white solid compound (4-23).

Example 24: Synthesis of compound (4-24)

The synthesis route of the compound (4-24) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of b-carboline, 24 mg (0.126 mmol) CuI, Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 38 mg (yield: 7%) of a white solid compound (4-24).

Example 25: Synthesis of compound (4-25)

The synthesis route of the compound (4-25) is shown below.

(0.5 g, 1.005 mmol), 7-t-butyl d-carboline (0.2 g, 1.105 mmol) and CuI (24 mg, 0.126 mmol) ), 1,10-phenanthroline 45 mg (0.251 mmol), cesium carbonate (Cs ₂ CO ₃ ) 0.7 g (2.010 mmol) and dimethylformamide (DMF) 40 mL), and then stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-25) (yield: 50%).

Example 26: Synthesis of compound (4-26)

The synthesis route of the compound (4-26) is shown below.

A 1-necked 100 mL flask was charged with intermediate (2) (0.5 g, 1.005 mmol), carbazole 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10- phenanthroline (45 mg, 0.251 mmol), cesium carbonate (Cs ₂ CO ₃ ) (0.7 g, 2.010 mmol) and dimethylformamide (DMF) Lt; / RTI > After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 40%) of a white solid compound (4-26).

Example 27: Synthesis of compound (4-27)

The synthesis route of the compound (4-27) is shown below.

(0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of 4- (phenylamino) benzonitrile, 24 mg (0.126 mmol) of CuI, , 45 mg (0.251 mmol) of 10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 40%) of a white solid compound (4-27).

Example 28: Synthesis of compound (4-28)

The synthesis route of the compound (4-28) is shown below.

(0.5 g, 1.005 mmol), diphenylamine (0.2 g, 1.105 mmol), CuI (24 mg, 0.126 mmol), 1,10-phenanthroline was mixed with 45 mg (0.251 mmol) of phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Stir for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g (yield: 40%) of a white solid compound (4-28).

Example 29: Synthesis of compound (4-29)

The synthesis route of the compound (4-29) is shown below.

Intermediate 1 to obtain 100 mL flask (2) (0.5 g, 1.005 mmol), triphenyl borate-4-amine (triphenylamine 4-borate) (0.4 g, 1.105 mmol), Pd (PPh 3) 4 35 mg (0.030 mmol (20 mL) and K ₂ CO ₃ (0.25 g, 1.508 mmol) / H ₂ O (20 mL) were added to the solution, and the mixture was stirred under reflux for 6 Lt; / RTI > After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and purified by silica gel column chromatography to obtain 0.3 g (yield: 50%) of a white solid compound (4-29) ≪ / RTI >

Example  30: Synthesis of compound (4-30)

The synthesis route of the compound (4-30) is shown below.

In 1 100 mL flask, intermediate (2) (0.5 g, 1.005 mmol), imidazole borate (imidazole borate) (0.4 g, 1.105 mmol), Pd (PPh 3) 4 35 mg (0.030 mmol), toluene (toluene) (20 mL) and K ₂ CO ₃ (0.20 g, 1.508 mmol) / H ₂ O (20 mL) were added to the solution, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic phase was dried over anhydrous MgSO ₄ and purified by silica gel column chromatography to obtain 0.3 g (yield: 50%) of a white solid (4-30) ≪ / RTI >

Example 31: Synthesis of compound (4-31)

The synthesis route of the compound (4-31) is shown below.

A 1-necked 100 mL flask was charged with intermediate (3) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of d-carboline, 24 mg (0.126 mmol) CuI, Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-31) (yield: 40%).

Example 32: Synthesis of compound (4-32)

The synthesis route of the compound (4-32) is shown below.

A 1-necked 100 mL flask was charged with intermediate (3) (0.5 g, 1.005 mmol), carbazole 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10- phenanthroline (45 mg, 0.251 mmol), cesium carbonate (Cs ₂ CO ₃ ) (0.7 g, 2.010 mmol) and dimethylformamide (DMF) Lt; / RTI > After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-32) (yield: 35%).

Example 33: Synthesis of compound (4-33)

The synthesis route of the compound (4-33) is shown below.

A 1-necked 100 mL flask was charged with intermediate (4) (0.5 g, 1.005 mmol), 0.2 g (1.105 mmol) of d-carboline, 24 mg (0.126 mmol) CuI, Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) And the mixture was stirred at 130 DEG C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-33) (yield: 40%).

Example 34: Synthesis of compound (4-34)

The synthesis route of the compound (4-34) is shown below.

A 1-necked 100 mL flask was charged with Intermediate 4 (0.5 g, 1.005 mmol), carbazole 0.2 g (1.105 mmol), CuI 24 mg (0.126 mmol), 1,10-phenanthroline phenanthroline), 0.7 g (2.010 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) (40 mL) Lt; / RTI > After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.2 g of a white solid (4-34) (yield: 40%).

Example 35: Synthesis of compound (4-35)

The synthesis route of the compound (4-35) is shown below.

(0.5 g, 1.002 mmol), diphenylamino d-carboline (0.4 g, 1.102 mmol), CuI (24 mg, 0.125 mmol), 1,10- Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.004 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) Then, the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.4 g of a white solid (4-35) (yield: 60%).

Example 36: Synthesis of compound (4-36)

The synthesis route of the compound (4-36) is shown below.

A 1-necked 100 mL flask was charged with intermediate (6) (0.5 g, 1.002 mmol), benzofuro d-carboline (0.3 g, 1.102 mmol), CuI (24 mg, 0.125 mmol) Was mixed with 45 mg (0.251 mmol) of 1,10-phenanthroline, 0.7 g (2.004 mmol) of cesium carbonate (Cs ₂ CO ₃ ) and 40 mL of dimethylformamide (DMF) , And the mixture was stirred at 120 to 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 0.3 g of a white solid (4-36) (yield: 45%).

≪ Test Example 1 >

The UV / VIS spectra of the compounds of the present invention were measured using a Jasco V-630 instrument and PL (photoluminescence) spectra were measured using a Jasco FP-8500 instrument.

UV / VIS and PL results of compounds Classification (compound) UV / VIS (nm) * 1 PL (nm, room temperature) * 2 Example 1 (Compound 4-1) 252, 261, 283, 310, 345, 361 386.5 Example 2 (Compound 4-2) 259, 326 374.5, 392 Example 3 (Compound 4-3) 261, 327 380, 397 Example 4 (Compound 4-4) 270 370.5, 388.5 Example 5 (Compound 4-5) 244, 260, 292, 300, 344, 359 386.5 Example 6 (Compound 4-6) 261, 292, 360 370.5, 388.5 Example 7 (Compound 4-7) 258, 309, 360 393 Example 8 (Compound 4-8) 261, 345, 361 431 Example 9 (Compound 4-9) 260, 304, 359 370.5, 388 Example 10 (Compound 4-10) 261, 300, 359 370.5, 388.5 Example 11 (Compound 4-11) 261, 314 371.5, 389.5 Example 12 (Compound 4-12) 261, 290, 344 431.5 Example 13 (Compound 4-13) 244, 252, 260, 291, 305, 359 370.5, 388.5 Example 14 (Compound 4-14) 262, 329 417.5 Example 15 (Compound 4-15) 261, 307, 360 371.5, 391, 411.5 Example 16 (Compound 4-16) 259, 328, 362 400.5 Example 17 (Compound 4-17) 251, 261, 282, 302, 310, 346, 362 399.5 Example 18 (Compound 4-18) 244, 262, 293, 300, 308, 332, 345, 360 400.5 Example 19 (Compound 4-19) 261, 300, 331, 343, 361 402.5 Example 20 (Compound 4-20) 242, 261, 332, 347, 363 432 Example 21 (Compound 4-21) 253, 307, 343, 361 403.5 Example 22 (Compound 4-22) 245, 261, 295, 331, 362 403 Example 23 (Compound 4-23) 252, 260, 305, 330 400 Example 24 (Compound 4-24) 247, 287, 346, 361 403.5 Example 25 (Compound 4-25) 253, 260, 303, 330, 361 402.5 Example 26 (Compound 4-26) 243, 260, 284, 291, 324, 362 402.5 Example 27 (Compound 4-27) 262, 333 409.5 Example 28 (Compound 4-28) 262, 305, 363 456 Example 29 (Compound 4-29) 261, 294, 346 436 Example 30 (Compound 4-30) 261, 315, 360 402.5 Example 31 (Compound 4-31) 261, 292, 298, 325, 358 371, 388 Example 32 (Compound 4-32) 243, 260, 290, 359 370.5, 388 Example 33 (Compound 4-33) 261, 295, 331, 342, 361 402.5 Example 34 (Compound 4-34) 242, 260, 283, 291, 326, 361 402 Example 35 (Compound 4-35) 233, 262, 371 431.5 Example 36 (Compound 4-36) 242, 272, 300, 346, 360 386 * 1: 1.0 x 10 ^-5 M in methylene chloride
* 2: 5.0 x 10 ^-6 M in methylene chloride

The compounds of the present invention were analyzed by LC-MS using a Waters Acquity UPLC H-Class / SQD2 system instrument and the results are shown in Table 2 below.

LC / MS results of the compounds Classification (compound) MS Calcd. LC-MS Found [M + 1] < + > Example 1 (Compound 4-1) 643.76 644.39 Example 2 (Compound 4-2) 587.67 588.44 Example 3 (Compound 4-3) 729.83 730.54 Example 4 (Compound 4-4) 537.61 538.41 Example 5 (Compound 4-5) 627.69 628.42 Example 6 (Compound 4-6) 537.61 538.21 Example 7 (Compound 4-7) 587.67 588.24 Example 8 (Compound 4-8) 704.82 705.53 Example 9 (Compound 4-9) 593.72 594.43 Example 10 (Compound 4-10) 537.61 538.14 Example 11 (Compound 4-11) 639.75 640.27 Example 12 (Compound 4-12) 614.74 615.45 Example 13 (Compound 4-13) 536.62 537.41 Example 14 (Compound 4-14) 563.65 564.35 Example 15 (Compound 4-15) 538.64 539.14 Example 16 (Compound 4-16) 587.67 588.17 Example 17 (Compound 4-17) 643.76 644.46 Example 18 (Compound 4-18) 627.69 628.42 Example 19 (Compound 4-19) 537.61 538.41 Example 20 (Compound 4-20) 704.82 705.53 Example 21 (Compound 4-21) 587.67 588.24 Example 22 (Compound 4-22) 537.61 538.21 Example 23 (Compound 4-23) 729.83 730.54 Example 24 (Compound 4-24) 537.61 538.41 Example 25 (Compound 4-25) 593.72 594.43 Example 26 (Compound 4-26) 536.62 537.41 Example 27 (Compound 4-27) 563.65 564.42 Example 28 (Compound 4-28) 538.64 539.40 Example 29 (Compound 4-29) 614.74 615.32 Example 30 (Compound 4-30) 639.75 640.27 Example 31 (Compound 4-31) 537.61 538.27 Example 32 (Compound 4-32) 536.62 537.34 Example 33 (Compound 4-33) 537.61 538.34 Example 34 (Compound 4-34) 536.62 537.34 Example 35 (Compound 4-35) 706.83 707.79 Example 36 (Compound 4-36) 629.71 630.69

Device fabrication Test Example

2-TNATA is a hole injection layer, NPB is a hole transport layer, -ADN is a host of a light emitting layer, Bphen is an electron transport layer, Liq is an electron injection layer, and Al is a cathode. Respectively. The structures of these compounds are shown below.

Comparative test example  : ITO  / 2- TNATA  / NPB  / αβ- ADN , 9,9- diethyl -2,7-bis ((E) -4-tritylstyryl) -9H-fluorene / Bphen  / Liq  / Al

A blue fluorescent organic light-emitting device was prepared in the same manner as in Example 1 except that ITO (180 nm) / 2-TNATA (60 nm) / NPB (20 nm) / αβ-ADN: 9,9-diethyl- -9H-fluorene was deposited in the order of 10% (30 nm) / Bphen (40 nm) / Liq (2 nm) / Al (100 nm). Before deposition of the organic material, the ITO electrode was subjected to oxygen plasma treatment at 125 W for 2 minutes at 2 × 10 ^-2 Torr. Organic matters were deposited at a vacuum of 9 × 10 ^-7 Torr. The blue fluorescent dopant was co-deposited with 0.02 Å / sec on Liq and 0.18 Å / sec on αβ-ADN. / sec. < / RTI > The blue fluorescent dopant used in the experiment was 9,9-diethyl-2,7-bis ((E) -4-tritylstyryl) -9H-fluorene and the concentration of the dopant was fixed at 10%. After fabricating the device, it was sealed in a glove box filled with nitrogen gas to prevent air and moisture contact of the device. Barium oxide (Barium Oxide), which is a hygroscopic agent capable of removing moisture and so on, was put into a glass plate after 3M's adhesive tape was formed.

Test Example  One : ITO  / 2- TNATA  / NPB  / αβ- ADN , Example  3 (Compound 4-3) / Bphen   / Liq  / Al

A device was prepared in the same manner as in the comparative test except that the compound prepared in Example 3 was used as a light emitting layer instead of the blue fluorescent dopant used in the above Comparative Test Example.

Test Example  2 : ITO  / 2- TNATA  / NPB  / αβ- ADN , Example  18 (Compound 4-18) / Bphen / Liq  / Al

A device was fabricated in the same manner as in the comparative test except that the compound prepared in Example 18 was used as a light emitting layer in place of the blue fluorescent dopant used in the above Comparative Test Example.

Table 3 shows the electroluminescence characteristics of the organic luminescent devices prepared in the Comparative Test Examples and Test Examples 1 and 2.

division The color coordinates (x, y) EL peak (nm) The luminous efficiency (cd / A)
@ 20 mA / cm 2 External quantum efficiency (%)
@ 20 mA / cm 2 Comparative test example (0.17, 0.19) 456 1.89 1.20 Test Example 1 (0.16, 0.19) 476 3.23 2.31 Test Example 2 (0.16, 0.22) 481 2.85 1.79

As can be seen from Table 3 and FIG. 2, the device fabricated using the compounds of the present invention as a light emitting layer emits light in the blue wavelength region, and the devices of Test Examples 1 and 2 have higher luminous efficiency and And the external quantum efficiency characteristics are all improved. The improvement of the luminous efficiency and the external quantum efficiency characteristic can provide an organic electroluminescent device with improved driving voltage and luminous efficiency.

Claims (9)

An imidazole derivative represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
p is 1 or 2, L is a single bond, q is 0 or 1,
A is, when q is 0,

or

ego,
and when q is 1, it is selected from the following formula (3).
(3)

delete delete The method according to claim 1,
The imidazole derivative according to claim 1, wherein the compound represented by the formula (1) is selected from the following formula (4).
[Chemical Formula 4]

An organic electroluminescent device comprising the imidazole derivative of claim 1 or 4. 6. The method of claim 5,
Wherein the imidazole derivative is used as a material of the light emitting layer. A first electrode, a second electrode, and at least one organic film disposed between the electrodes,
Wherein the organic film comprises the imidazole derivative of claim 1 or claim 4. 8. The method of claim 7,
The organic layer includes a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, And at least one functional layer having at least one functional group at the same time. 8. The method of claim 7,
The imidazole derivative is contained in any one selected from the group consisting of an electron blocking layer, an electron transport layer, an electron injection layer, a functional layer having both an electron transport function and an electron injection function, and a light emitting layer constituting the organic film The organic electroluminescent device comprising:

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