KR101806464B1 - Pyrimidine derivative substitued with pyridyl group, and organic electroluminescent device including the same - Google Patents

Pyrimidine derivative substitued with pyridyl group, and organic electroluminescent device including the same Download PDF

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KR101806464B1
KR101806464B1 KR1020150162427A KR20150162427A KR101806464B1 KR 101806464 B1 KR101806464 B1 KR 101806464B1 KR 1020150162427 A KR1020150162427 A KR 1020150162427A KR 20150162427 A KR20150162427 A KR 20150162427A KR 101806464 B1 KR101806464 B1 KR 101806464B1
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유용재
고병수
구자룡
김규식
한갑종
오유진
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Abstract

There is provided a pyrimidine derivative to which a pyridyl group represented by the following general formula (1) is bonded.
[Chemical Formula 1]

Figure 112017057311098-pat00068

Wherein Ar 1 and Ar 2 are each independently phenyl, biphenyl or naphthyl,
X 1 and X 2 are each independently CH or N, provided that one of X 1 and X 2 is N.

Description

[0001] The present invention relates to a pyrimidine derivative to which a pyridyl group is bonded, and an organic electroluminescent device including the organic electroluminescent device including the pyrimidine derivative substituted pyridyl group,

The present invention relates to a pyrimidine derivative, specifically, a pyrimidine derivative to which a specific pyridyl group is bonded, and an organic electroluminescent device including the pyrimidine derivative. More particularly, the present invention relates to an organic electroluminescent device having high luminous efficiency and a specific pyridyl group- Pyrimidine derivatives.

From the CRT (Cathode Ray Tube), which was the main market of the early display industry, to the LCD (Liquid Crystal Display) which is the most used now, the display industry has developed remarkably over the past few decades.

Nevertheless, the demand for a flat display device having a small space occupation has been increased due to the recent enlargement of display devices. However, LCD has a disadvantage that a separate light source is required because the viewing angle is limited and the device is not self-luminous. For this reason, OLEDs (Organic Light Emitting Diodes) have attracted attention as displays using self-emission phenomenon.

In 1963, OLED was first attempted to study the carrier injection type electroluminescence (EL) using a single crystal of anthracene aromatic hydrocarbons by Pope et al. 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.

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 light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer, electrons are injected into the organic layer, excitons are formed when injected holes and electrons meet, When it falls to a state, it becomes a light. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can 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 luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a 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, light of a desired wavelength can be obtained depending on the kind of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device, 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, the development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently achieved, and therefore, the development of new materials has been continuously required.

Korean Patent Publication No. 10-2014-0009263 Korean Patent Publication No. 10-1317495

The present inventors have found that when a pyrimidine derivative compound to which a specific pyridyl group is bonded is used as an element for forming an organic material layer of an organic electronic device, it is possible to exhibit effects such as an increase in the efficiency of the device, a decrease in the driving voltage and an increase in stability . Accordingly, it is an object of the present invention to provide a specific pyridyl derivative-bonded pyrimidine derivative compound and an organic electronic device using the same.

According to one aspect of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

Figure 112015112931366-pat00001

Wherein Ar 1 and Ar 2 are each independently C 6 -C 30 aryl or C 5 -C 30 heteroaryl;

X 1 and X 2 are each independently CH or N, provided that one of X 1 and X 2 is N;

A has one of the structures represented by the following formula (2).

(2)

Figure 112015112931366-pat00002

Wherein X 3 to X 4 each independently represent CH, CR 1 or N;

R 1 to R 2 are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, diphenylphosphine group, diphenylphosphoroxide group, C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 30 alkylsilyl, C 1 -C 20 alkoxy, C 6 -C 20 aryloxy, C 1 -C 20 alkylthio, C 6 -C 30 aryl, C 6 -C 30 aralkyl, C 1 -C 10 C 2 -C 8 heterocycloalkyl, C 5 -C 30 heteroaryl, C 5 -C 30 heteroaralkyl, C 6 -C 20 arylthio]

According to another aspect of the present invention, the specific pyridyl group is bonded An organic electroluminescent device comprising a pyrimidine derivative is provided.

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

According to another aspect of the present invention, the pyridyl derivative to which the specific pyridyl group is bound comprises 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, Emitting layer is contained in at least one selected from the group consisting of a light-emitting layer and a light-emitting layer.

The pyridyl derivative to which the specific pyridyl group is bonded according to the present invention may be used as an organic material layer of an organic electronic device including an organic light emitting device by introducing various aryl groups, heteroaryl groups and the like into the pyridyl group. The organic electronic device including the organic light emitting device using the compound represented by the formula (1) according to the present invention as the material of the organic material layer exhibits excellent characteristics in terms of efficiency, driving voltage and lifetime.

1 is a schematic diagram of a pyrimidine derivative according to an embodiment of the present invention.

As used herein, the term "aryl " means a polyunsaturated aromatic hydrocarbon substituent which may be a single ring or multiple rings (one to three rings) fused or covalently bonded together 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, pyreneyl, perylenyle, It is not limited.

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, indolizine, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like can be prepared by reacting the above- But are 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.

A pyridyl group according to an embodiment of the present invention is bonded The pyrimidine derivative may be represented by the following formula (1).

[Chemical Formula 1]

Figure 112015112931366-pat00003

Wherein Ar 1 and Ar 2 are each independently C 6 -C 30 aryl or C 5 -C 30 heteroaryl,

Ar 1 and Ar 2 are suitably phenyl, biphenyl or naphthyl;

X 1 and X 2 are each independently CH or N, provided that one of X 1 and X 2 is N;

A has one of the structures represented by the following formula (2).

(2)

Figure 112015112931366-pat00004

Wherein X 3 and X 4 are each independently CH, CR 1 or N;

R 1 to R 2 are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, diphenylphosphine group, diphenylphosphoroxide group, C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 30 alkylsilyl, C 1 -C 20 alkoxy, C 6 -C 20 aryloxy, C 1 -C 20 alkylthio, C 6 -C 30 aryl, C 6 -C 30 aralkyl, C 1 -C 10 C 2 -C 8 heterocycloalkyl, C 5 -C 30 heteroaryl, C 5 -C 30 heteroaralkyl, C 6 -C 20 arylthio,

More specifically, R 1 to R 2 have any one of structures represented by the following formula (3)

(3)

Figure 112015112931366-pat00005

Specific examples of the compound represented by the formula (1) of the present invention include those represented by the following formula (4). However, the compound represented by the formula (1) of the present invention is not limited to the compounds of the following formula (4).

[Chemical Formula 4]

Figure 112015112931366-pat00006

Figure 112015112931366-pat00007

Figure 112015112931366-pat00008

Figure 112015112931366-pat00009

Figure 112015112931366-pat00010

Figure 112015112931366-pat00011
Figure 112015112931366-pat00012

Figure 112015112931366-pat00013
Figure 112015112931366-pat00014

Figure 112015112931366-pat00015

Figure 112015112931366-pat00016

Figure 112015112931366-pat00017

Figure 112015112931366-pat00018

Figure 112015112931366-pat00019

Figure 112015112931366-pat00020

Figure 112015112931366-pat00021

The specific pyridyl group represented by the general formula (1) The pyrimidine derivative can be synthesized using a known organic synthesis method. When the specific pyridyl group is bonded Pyrimidine The method of synthesizing the derivatives can be easily recognized by those skilled in the art with reference to the following production examples.

Further, according to the present invention, the specific pyridyl group represented by the general formula (1) Pyrimidine There is provided an organic electroluminescent device comprising a derivative thereof.

The specific pyridyl group-bonded pyrimidine derivative of Formula 1 is useful as an electron transport layer material and can be used as a material for various other 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 may have a structure in which a specific pyridyl group represented by the general formula (1) And at least one pyrimidine derivative.

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, when the particular pyridyl group is attached The pyrimidine 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 pyrimidine 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 pyrimidine derivative to which the specific pyridyl group is bonded may be included in the organic film as a single substance or a combination of different substances. Alternatively, the pyrimidine 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.

The organic layer may be prepared by a variety of polymer materials, not by vapor deposition, but by a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

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 intended to illustrate the present invention and the scope of the present invention is not limited thereto.

[Example]

Intermediate Synthesis Example 1: Synthesis of Intermediate (3)

Figure 112015112931366-pat00022

(Synthesis of Intermediate (1)

40.0 g (168.8 mmol) of 2,5-dibromopyridine is placed in 2 L of anhydrous ethyl ether and is maintained at -78 ° C. Slowly add 70.9 mL (177.2 mmol) of n-butyllithium (2.5 M, n-butyllithium) and keep for 1 hour. To the reaction mixture slowly add 14.3 mL (185.6 mmol) of anhydrous dimethylformamide. The reaction mixture is maintained at -78 < 0 > C for 1 hour and then slowly raised to room temperature. 100 mL of a 1.0 M aqueous hydrochloric acid solution (1.0 M aq. HCl) was added to the reaction mixture, stirred for 15 minutes, and the organic layer was separated. The resulting aqueous layer is extracted again with anhydrous ethyl ether. After the obtained organic layer were combined, washed with water and dried over MgSO 4. The organic layer was concentrated under reduced pressure to obtain 22.1 g (yield: 70%) of a solid compound (intermediate (1)).

(Synthesis of Intermediate (2)

22.1 g (118.8 mmol) of Intermediate (1) and 23.3 g (118.8 mmol) of 4-acetyl biphenyl are added to 500 ml of ethanol. After the mixture is stirred at room temperature, an aqueous solution of 8.8 g (220 mmol) of sodium hydroxide dissolved in 40 ml of water is slowly added dropwise to the reaction solution. After stirring for 7 hours at room temperature, the reaction solution is allowed to stand overnight. The precipitate was collected via filtration, dispersed in water, washed with ethanol and vacuum dried to obtain 38.7 g (yield: 90%) of solid compound (intermediate (2)).

(Synthesis of Intermediate (3)

38.7 g (106 mmol) of the synthesized intermediate (2) and 17 g (109 mmol) of benzamidine hydrochloride are added to 500 ml of ethanol. After the mixture is stirred at room temperature, 8.72 g (218 mmol) of sodium hydroxide are slowly added to the reaction solution in small amounts, respectively. Thereafter, the reaction solution is heated to a reflux temperature, stirred for 8 hours, and then allowed to stand overnight. The precipitate was collected by filtration, washed with water, followed by methanol, and vacuum dried to obtain 18.5 g (yield: 37%) of a solid compound (Intermediate (3)).

Intermediate Synthesis Example 2: Synthesis of Intermediate (6)

Figure 112015112931366-pat00023

(Synthesis of Intermediate (4)

88.6 ml (0.222 mol) of n-butyllithium (2.5 M in hexane) and 350 ml of THF were placed in a 2 L round-bottomed flask, stirred under nitrogen atmosphere at -75 ° C and then 2,6-dibromopyridine 6-dibromopyridine (50.0 g, 0.211 mol) was dissolved in 245 mL of THF and slowly added dropwise at -75 ° C for 1 hour. After 1 hour, stir for another 30 minutes and add 24.5 ml (0.317 mol) of dimethylformamide. Then, the mixture was stirred at a reaction temperature of -40 ° C for 1-1.5 hours and then stirred for 1 hour while slowly raising the temperature to 0 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and 220 mL of MeOH was added thereto. Then, the mixture was separated into DCM and water, and the organic phase was dried over anhydrous MgSO 4. The organic layer was concentrated and purified by silica gel column chromatography to obtain a white solid compound ) (17.7 g, yield: 45%).

(Synthesis of intermediate 5)

10.0 g (0.054 mol) of the intermediate (4), 10.5 g (0.054 mol) of 4-acetylbiphenyl and 300 mL of EtOH were added to a 1-liter L flask and stirred for 30 minutes. Then, 4.0 g ) In 20 mL of H 2 O is slowly added dropwise. After the dropwise addition, the mixture was stirred for 7 hours or more. After the reaction was completed, the precipitate was filtered, and the solid was dispersed in 200 mL of water, followed by further filtration, washing with 200 mL of EtOH and drying to obtain 16.6 g (yield: 85%) of white solid compound (Intermediate (5)).

(Synthesis of Intermediate (6)

15.0 g (0.041 mol) of Intermediate (5), 6.6 g (0.042 mol) of benzamidine hydrochloride, and 300 mL of EtOH were added to a 1-liter L flask, and after 30 minutes, 3.3 g mol) slowly. The mixture is refluxed at 80-100 ° C for 8 hours or more under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature and the precipitate was filtered. The resulting solid was dispersed in 200 mL of water, filtered, washed with 200 mL of EtOH and dried to obtain 4.8 g (yield: 25%) of white solid compound .

Various pyrimidine derivative compounds were synthesized as follows using the synthesized intermediate compounds.

Example 1: Synthesis of Compound 4-1 (WS15-30-144)

The synthesis route of the compound 4-1 (WS15-30-144) is shown below.

Figure 112015112931366-pat00024

2 1000 mL of intermediate (3) the composite to the flask 5 g (10.7 mmol), Int.1 3.9 g (11.7 mmol), Pd (PPh 3) 4 0.62 g (0.54 mmol), and Cs 2 CO 3 10.4 g (31.9 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was stirred under reflux for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 1.5 g (yield: 23%) of Compound 4-1 (WS15-30-144).

Example 2: Synthesis of compound 4-3 (WS15-30-125)

The synthesis route of the compound 4-3 (WS15-30-125) is shown below.

Figure 112015112931366-pat00025

2 the intermediate said composite to obtain 1000 mL flask (3) 3.0 g (6.4 mmol ), naphthalene-Boro Nick Acid (2-naphthylboronic acid) 1.2 g (6.9 mmol), Pd (PPh 3) 4 0.37 g (0.32 mmol), And 6.25 g (19.1 mmol) of Cs 2 CO 3 were placed in a mixed solution of 200 mL of toluene, 100 mL of ethanol and 100 mL of distilled water, and the mixture was refluxed and stirred for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 3.0 g (yield: 45%) of 4-3 (WS15-30-125).

Example 3: Synthesis of compound 4-4 (WS15-30-137)

The synthesis route of the compound 4-4 (WS15-30-137) is shown below.

Figure 112015112931366-pat00026

2 1000 mL of the synthetic intermediate (3) 7 g (15.1 mmol ), Int.2 5.05 g (16.6 mmol), Pd (PPh 3) 4 0.87 g (0.75 mmol), and Cs 2 CO 3 in a flask 14.7 g (45.1 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 2.7 g (yield: 32%) of compound 4-4 (WS15-30-137).

Example 4: Synthesis of compound 4-7 (WS15-30-183)

The synthesis route of the compound 4-7 (WS15-30-183) is shown below.

Figure 112015112931366-pat00027

2 1000 mL of intermediate (3) the composite in a flask 8 g (17.2 mmol), Int.3 8.15 g (18.9 mmol), Pd (PPh 3) 4 0.99 g (0.85 mmol), and Cs 2 CO 3 16.8 g (51.5 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed with stirring for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 1.9 g (yield: 16%) of compound 4-7 (WS15-30-183).

Example 5: Synthesis of compound 4-8 (WS15-30-200)

The synthesis route of the compound 4-8 (WS15-30-200) is shown below.

Figure 112015112931366-pat00028

2 1000 mL of intermediate (3) the composite in a flask 8 g (17.2 mmol), Int.4 8.63g (18.9mmol), Pd (PPh 3) 4 0.99 g (0.85 mmol), and Cs 2 CO 3 16.8 g (51.5 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed with stirring for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 1.3 g (yield: 10%) of Compound 4-8 (WS15-30-200).

Example 6: Synthesis of Compound 4-11 (WS15-30-131)

The synthesis route of the compound 4-11 (WS15-30-131) is shown below.

Figure 112015112931366-pat00029

The second intermediate in the synthesis obtain 1000 mL flask (3) 5 g (10.7 mmol ), Int.5 4.6 g (11.7 mmol), Pd (PPh 3) 4 0.62 g (0.54 mmol), and Cs 2 CO 3 10.4 g (31.9 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed with stirring for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 2.3 g (yield: 33%) of the compound 4-11 (WS15-30-131).

Example 7: Synthesis of Compound 4-12 (WS15-30-194)

The synthesis route of the compound 4-12 (WS15-30-194) is shown below.

Figure 112015112931366-pat00030

2, the above synthetic intermediate to obtain 1000 mL flask (3) 7 g (15.1 mmol ), Int.6 7.56 g (16.6mmol), Pd (PPh 3) 4 0.87 g (0.75 mmol), and Cs 2 CO 3 14.7 g (45.1 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 2 g (yield: 18%) of Compound 4-12 (WS15-30-194).

Example 8: Synthesis of compound 4-15 (WS15-30-248)

The synthesis route of the compound 4-15 (WS15-30-248) is shown below.

Figure 112015112931366-pat00031

2 1000 mL of intermediate (3) 7 g (15.1 mmol ) synthesized in the flask, Int.28 4.95 g (16.6mmol), Pd (PPh 3) 4 0.87 g (0.75 mmol), and Cs 2 CO 3 14.7 g (45.1 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 3.1 g (yield: 32.2%) of Compound 4-15 (WS15-30-248).

Example 9: Synthesis of compound 4-16 (WS15-30-229)

The synthesis route of the compound 4-16 (WS15-30-229) is shown below.

Figure 112015112931366-pat00032

1 500 mL to intermediate (3) 5.0 g (0.011 mol ), Int.7 flask, 3.5 g (0.011 mol), Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto, followed by extraction with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.3 g (yield: 21%) of a white solid compound 4-16 (WS15-30-229) ≪ / RTI >

Example 10: Synthesis of Compound 4-17 (WS15-30-210)

The synthesis route of the compound 4-17 (WS15-30-210) is shown below.

Figure 112015112931366-pat00033

Intermediate 1 (3) 5.0 g (0.011 mol ) to obtain 500 mL flask, Int.8 3.8 g (0.011 mol) , Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.7 g (yield: 25%) of Compound 4-17 (WS15-30-210) ≪ / RTI >

Example 11: Synthesis of compound 4-18 (WS15-30-225)

The synthesis route of the compound 4-18 (WS15-30-225) is shown below.

Figure 112015112931366-pat00034

2 1000 mL flask in the above synthesis intermediates (3) 7.0 g (15.1 mmol ), Int.9 3.28g (16.6mmol), Pd (PPh 3) 4 0.87 g (0.75 mmol), and Cs 2 CO 3 14.7 g (45.1 mmol) were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed and stirred for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 1.0 g (yield: 12%) of Compound 4-18 (WS15-30-225).

Example 12: Synthesis of Compound 4-19 (WS15-30-218)

The synthesis route of the compound 4-19 (WS15-30-218) is shown below.

Figure 112015112931366-pat00035

5.0 g (10.7 mmol) of the synthesized intermediate (3), 2.5 g (11.7 mmol) of dibenzo [b, d] furan-4-ylboronic acid, (PPh 3 ) 4 and 10.4 g (31.9 mmol) of Cs 2 CO 3 were added to a mixed solution of 300 mL of toluene, 150 mL of ethanol and 150 mL of distilled water, and the mixture was refluxed for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 1.8 g (yield: 30%) of Compound 4-19 (WS15-30-218).

Example 13: Synthesis of compound 4-20 (WS15-30-213)

The synthesis route of Compound 4-20 (WS15-30-213) is shown below.

Figure 112015112931366-pat00036

1 intermediate (3) in 500 mL flask 5.0 g (0.011 mol), 4- dibenzo-thiophenyl boronic acid (4-dibenzothiophenyl boronic acid) 2.5 g (0.011 mol), Pd (PPh 3) 4 0.4 g (0.333 mmol ) and 200 mL of toluene. While stirring, 100 mL of ethanol and K 2 CO 3 2.2 g (0.017 mol) / H 2 O 100 mL were added and stirred for 6 hours under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.5 g of a white solid compound 4-20 (WS15-30-213) : 40%).

Example 14: Synthesis of compound 4-21 (WS15-30-211)

The synthesis route of the compound 4-21 (WS15-30-211) is shown below.

Figure 112015112931366-pat00037

To a 500 mL flask was added 2.7 g (0.011 mol) of intermediate (3) and 5.0 g (0.011 mol) of 4- (naphthalen-2-yl) phenylboronic acid ) under Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g (0.017 mol) / H 2 O was added to 100 mL, and heated to reflux And the mixture was stirred for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.4 g of a white solid compound 4-21 (WS15-30-211) 23%).

Example 15: Synthesis of compound 4-22 (WS15-30-228)

The synthesis route of the compound 4-22 (WS15-30-228) is shown below.

Figure 112015112931366-pat00038

Intermediate 1 (3) 5.0 g (0.011 mol ) to obtain 500 mL flask, Int.10 5.1 g (0.011 mol) , Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, water was added and extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.5 g (yield: 32%) of Compound 4-22 (WS15-30-228) ≪ / RTI >

Example 16: Synthesis of compound 4-25 (WS15-30-235)

The synthesis route of the compound 4-25 (WS15-30-235) is shown below.

Figure 112015112931366-pat00039

Intermediate 1 (3) 5.0 g (0.011 mol ), Int.11 4.5 g (0.011 mol), Pd (PPh 3) to obtain 500 mL flask 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, water was added and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.6 g (yield: 36%) of a white solid compound 4-25 (WS15-30-235) ≪ / RTI >

Example 17: Synthesis of Compound 4-29 (WS15-35-001)

The synthesis route of the compound 4-29 (WS15-35-001) is shown below.

Figure 112015112931366-pat00040

1 500 mL to intermediate (3) 5.0 g (0.011 mol ), Int.13 flask, 6.7 g (0.017 mol), Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.6 g (yield: 35.4%) of Compound 4-29 (WS15-35-001) ≪ / RTI >

Example 18: Synthesis of compound 4-30 (WS15-35-002)

The synthesis route of Compound 4-30 (WS15-35-002) is shown below.

Figure 112015112931366-pat00041

Intermediate 1 (3) 5.0 g (0.011 mol ) to obtain 500 mL flask, Int.14 6.5 g (0.017 mol) , Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.21 g of a white solid compound 4-29 (WS15-35-002) (yield: 16.7% ≪ / RTI >

Example 19: Synthesis of compound 4-32 (WS15-30-262)

The synthesis route of the compound 4-32 (WS15-30-262) is shown below.

Figure 112015112931366-pat00042

Intermediate 1 to obtain 500 mL flask (3) 5.0 g (0.011 mol ), Int.24 5.8 g (0.017 mol), Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 4.3 g (yield: 65.0%) of 4-32 (WS15-30-262) ≪ / RTI >

Example 20: Synthesis of compound 4-33 (WS15-30-271)

The synthesis route of the compound 4-33 (WS15-30-271) is shown below.

Figure 112015112931366-pat00043

Intermediate 1 (3) 5.0 g (0.011 mol ) to obtain 500 mL flask, Int.25 6.1 g (0.017 mol) , Pd (PPh 3) 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.9 g (yield: 57.5%) of 4-33 (WS15-30-271) ≪ / RTI >

Example 21: Synthesis of compound 4-35 (WS15-35-003)

The synthesis route of compound 4-35 (WS15-35-003) is shown below.

Figure 112015112931366-pat00044

5.0 g (0.011 mol) of Intermediate (3), 5.8 g (0.017 mol) of Int.26, 0.4 g (0.333 mmol) of Pd (PPh 3 ) 4 and 200 mL of toluene were placed in a 500 mL flask with one mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.38 g (yield: 51.2%) of 4-35 (WS15-35-003) ≪ / RTI >

Example 22: Synthesis of compound 4-36 (WS15-35-004)

The synthesis route of compound 4-36 (WS15-35-004) is shown below.

Figure 112015112931366-pat00045

Intermediate 1 (3) 5.0 g (0.011 mol ), Int.27 6.1 g (0.017 mol), Pd (PPh 3) to obtain 500 mL flask 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 4.1 g of a white solid compound 4-36 (WS15-35-004) (yield: 60.5% ≪ / RTI >

Example 23: Synthesis of compound 4-41 (WS15-30-258)

The synthesis route of Compound 4-41 (WS15-30-258) is shown below.

Figure 112015112931366-pat00046

Intermediate 1 (3) 5.0 g (0.011 mol ), Int.15 4.2 g (0.011 mol), Pd (PPh 3) to obtain 500 mL flask 4 0.4 g (0.333 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto and the mixture was extracted with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.3 g of 4-41 (WS15-30-258) : 47%).

Example 24: Synthesis of compound 4-42 (WS15-30-270)

The synthesis route of the compound 4-41 (WS15-30-270) is shown below.

Figure 112015112931366-pat00047

5.0 g (0.011 mol) of Intermediate (3), 4.4 g (0.011 mol) of Int.16, 0.4 g (0.333 mmol) of Pd (PPh 3 ) 4 and 200 mL of toluene were placed in a 500 mL flask with one mL, K 2 CO 3 2.2 g was added to (0.017 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.5 g of 4-42 (WS15-30-270) : 49%).

Example 25: Synthesis of compound 4-46 (WS15-35-005)

The synthesis route of Compound 4-46 (WS15-35-005) is shown below.

Figure 112015112931366-pat00048

Intermediate 1 to obtain 250 mL flask (3) 3.2 g (7.01 mmol ), Int.17 3.3 g (7.72 mmol), Pd (PPh 3) 4 0.41 g (0.35 mmol), Toluene 38 mL, EtOH 19 mL and 2M K 2 CO 3 (14.0 mmol), and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled at room temperature overnight, and the resulting solid was filtered with EtOH. The solid was dissolved in chloroform and purified by silica gel column chromatography (EA: HEX). EA and filtered to obtain 1.20 g (yield: 24.9%) of compound 4-46 (WS15-35-005) as a yellow solid.

Example 26: Synthesis of compound 4-48 (WS15-35-006)

The synthesis route of Compound 4-46 (WS15-35-006) is shown below.

Figure 112015112931366-pat00049

Intermediate 1 to obtain 250 mL flask (3) 3.2 g (7.01 mmol ), Int.18 3.6 g (7.72 mmol), Pd (PPh 3) 4 0.41 g (0.35 mmol), Toluene 38 mL, EtOH 19 mL and 2M K 2 CO 3 (14.0 mmol), and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled at room temperature overnight, and the resulting solid was filtered with EtOH. The solid was dissolved in chloroform and purified by silica gel column chromatography (EA: HEX). EA and filtered to obtain 1.51 g (yield: 29.3%) of compound 4-48 (WS15-35-006) as a yellow solid.

Example 27: Synthesis of compound 4-52 (WS15-35-007)

The synthesis route of Compound 4-52 (WS15-35-007) is shown below.

Figure 112015112931366-pat00050

3.5 g (7.72 mmol) of Int 19 and 0.41 g (0.35 mmol) of Pd (PPh 3 ) 4 , 38 mL of Toluene, 19 mL of EtOH and 2 M K 2 CO 3 (14.0 mmol), and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled at room temperature overnight, and the resulting solid was filtered with EtOH. The solid was dissolved in chloroform and purified by silica gel column chromatography (EA: HEX). EA and filtered to obtain 2.1 g (yield: 41.9%) of compound 4-52 (WS15-35-007) as a yellow solid.

Example 28: Synthesis of compound 4-53 (WS15-35-008)

The synthesis route of Compound 4-53 (WS15-35-008) is shown below.

Figure 112015112931366-pat00051

Intermediate 1 to obtain 250 mL flask (3) 3.2 g (7.01 mmol ), Int.20 3.3 g (7.72 mmol), Pd (PPh 3) 4 0.41 g (0.35 mmol), Toluene 38 mL, EtOH 19 mL and 2M K 2 CO 3 (14.0 mmol), and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled at room temperature overnight, and the resulting solid was filtered with EtOH. The solid was dissolved in chloroform and purified by silica gel column chromatography (EA: HEX). EA and filtered to obtain 1.7 g (Yield: 35.2%) of compound 4-53 (WS15-35-008) as a yellow solid.

Example 29: Synthesis of compound 4-54 (WS15-35-009)

The synthesis route of Compound 4-54 (WS15-35-009) is shown below.

Figure 112015112931366-pat00052

Intermediate 1 to obtain 250 mL flask (3) 3.2 g (7.01 mmol ), Int.21 2.9 g (7.72 mmol), Pd (PPh 3) 4 0.41 g (0.35 mmol), Toluene 38 mL, EtOH 19 mL and 2M K 2 CO 3 (14.0 mmol), and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled at room temperature overnight, and the resulting solid was filtered with EtOH. The solid was dissolved in chloroform and purified by silica gel column chromatography (EA: HEX). EA and filtered to obtain 5.0 g (yield: 72.3%) of compound 4-54 (WS15-35-009) as a yellow solid.

Example 30: Synthesis of compound 4-68 (WS15-30-266)

The synthesis route of Compound 4-68 (WS15-30-266) is shown below.

Figure 112015112931366-pat00053

5.0 g (0.011 mol) of Intermediate (3), 3.5 g (0.011 mol) of Int.22, 0.4 g (0.323 mmol) of Pd (PPh 3 ) 4 and 200 mL of toluene were placed in a 500 mL flask with one mL, and K 2 CO 3 2.2 (0.016 mol) / H 2 O (100 mL), and the mixture was stirred under reflux for 7 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.0 g of a white solid compound 4-68 (WS15-30-266) : 48%).

Example 31: Synthesis of compound 4-70 (WS15-35-010)

The synthesis route of Compound 4-70 (WS15-35-010) is shown below.

Figure 112015112931366-pat00054

Intermediate 1 (3) 5.0 g (0.011 mol ) to obtain 500 mL flask, Int.23 3.5 g (0.011 mol) , Pd (PPh 3) 4 0.4 g (0.323 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, and K 2 CO 3 2.2 (0.016 mol) / H 2 O (100 mL), and the mixture was stirred under reflux for 7 hours. After the reaction was completed, the reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.6 g of a white solid compound 4-68 (WS15-35-010) : 56.7%).

Example 32: Synthesis of compound 4-71 (WS15-30-124)

The synthesis route of compound 4-71 (WS15-30-124) is shown below.

Figure 112015112931366-pat00055

Intermediate 1 (6) 3.7 g (7.968 mmol ) to obtain 500 mL flask, Int.1 2.6 g (7.968 mmol) , Pd (PPh 3) 4 0.3 g (0.239 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, under K 2 CO 3 1.7 g (11.952 mmol) / H 2 O was added to 100 mL, heated to reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.7 g of a white solid compound 4-71 (WS15-30-124) : 79%).

Example 33: Synthesis of compound 4-73 (WS15-30-127)

The synthesis route of the compound 4-73 (WS15-30-127) is shown below.

Figure 112015112931366-pat00056

Intermediate 1 (6) 6.5 g (0.014 mol ) to obtain 500 mL flask, 2-naphthalenesulfonic acid (2-naphthalene boronic acid) 2.4 g (0.014 mol), Pd (PPh 3) 4 0.5 g (0.420 mmol), toluene while stirring, such as 200 mL was stirred for 5 hours under ethanol 100 mL, K 2 CO 3 2.9 g (0.021 mol) / H 2 O was added to 100 mL, and heated to reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.0 g (yield: 42%) of a white solid compound 4-73 (WS15-30-127) ≪ / RTI >

Example 34: Synthesis of compound 4-74 (WS15-30-129)

The synthesis route of Compound 4-74 (WS15-30-129) is shown below.

Figure 112015112931366-pat00057

(0.013 mol) of Intermediate (6), 3.9 g (0.013 mol) of Int.2, 0.4 g (0.388 mmol) of Pd (PPh 3 ) 4 and 200 mL of toluene were placed in a 500 mL flask with one mL, K 2 CO 3 2.7 g was added to (0.019 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After the reaction was completed, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.7 g (yield: 37%) of 4-74 (WS15-30-129) ≪ / RTI >

Example 35: Synthesis of compound 4-75 (WS15-30-146)

The synthesis route of Compound 4-75 (WS15-30-146) is shown below.

Figure 112015112931366-pat00058

(0.072 mol) of intermediate (6), 5.2 g (0.026 mol) of diphenylphosphine oxide, NiCl 2 (dppp) , 0.9 g (1.723 mmol) of Cs 2 CO 3, 11.2 g (0.034 mol) of Cs 2 CO 3 and 300 mL of DMF, and refluxed under nitrogen at 100-120 ° C for 24 hours. After the reaction was completed, the solvent was distilled off, water was added and the mixture was extracted with DCM. The organic phase was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.6 g of a white solid compound 4-75 (WS15-30-146) 16%).

Example 36: Synthesis of compound 4-76 (WS15-30-133)

The synthesis route of the compound 4-76 (WS15-30-133) is shown below.

Figure 112015112931366-pat00059

1 in 500 mL intermediate (6) 5.5 g (0.012 mol ), Int.12 flask, 4.8 g (0.012 mol), Pd (PPh 3) 4 0.4 g (0.355 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.5 g was added to (0.018 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.8 g (yield: 23%) of a white solid compound 4-76 (WS15-30-133) ≪ / RTI >

Example 37: Synthesis of compound 4-77 (WS15-30-154)

The synthesis route of Compound 4-77 (WS15-30-154) is shown below.

Figure 112015112931366-pat00060

In 1 500 mL flask, intermediate (6) 5.0 g (0.011 mol ), Int.3 4.6 g (0.011 mol), Pd (PPh 3) 4 0.4 g (0.323 mmol), while stirring, such as toluene (200 mL) ethanol (100 mL) and K 2 CO 3 2.2 g (0.016 mol) / H 2 O (100 mL), and the mixture was stirred under reflux for 6 hours. After completion of the reaction, water was added and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.5 g (yield: 34%) of Compound 3-77 (WS15-30-154) ≪ / RTI >

Example 38: Synthesis of compound 4-78 (WS15-30-182)

The synthesis route of Compound 4-78 (WS15-30-182) is shown below.

Figure 112015112931366-pat00061

Intermediate 1 (6) 7.0 g (0.015 mol ) to obtain 500 mL flask, Int.4 6.9 g (0.015 mol) , Pd (PPh 3) 4 0.5 g (0.452 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 3.1 g (0.023 mol) / H 2 O was added to 100 mL, and stirred for 5 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 2.1 g (yield: 20%) of 4-78 (WS15-30-182) ≪ / RTI >

Example 39: Synthesis of compound 4-81 (WS15-30-126)

The synthesis route of the compound 4-81 (WS15-30-126) is shown below.

Figure 112015112931366-pat00062

1 in 500 mL intermediate (6) 6.0 g (0.013 mol ) flask, Int.5 5.1 g (0.013 mol) , Pd (PPh 3) 4 0.4 g (0.388 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 2.7 g was added to (0.019 mol) / H 2 O 100 mL , and the mixture was stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 3.7 g (yield: 44%) of 4-81 (WS15-30-126) ≪ / RTI >

Example 40: Synthesis of compound 4-82 (WS15-30-190)

The synthesis route of the compound 4-82 (WS15-30-190) is shown below.

Figure 112015112931366-pat00063

Intermediate 1 (6) 7.0 g (0.015 mol ) to obtain 500 mL flask, Int.6 6.9 g (0.015 mol) , Pd (PPh 3) 4 0.5 g (0.452 mmol), while stirring, such as toluene 200 mL ethanol 100 mL, K 2 CO 3 3.1 g (0.023 mol) / H 2 O was added to 100 mL, and stirred for 6 hours under reflux. After completion of the reaction, water was added thereto and the mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO 4 and purified by silica gel column chromatography to obtain 1.7 g (yield: 16%) of a white solid compound 4-82 (WS15-30-190) ≪ / RTI >

≪ 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. The results are shown in Tables 1 and 2 below.

UV / VIS  And PL  Result -1 division compound UV (nm) * 1 PL (nm, room temperature) * 2 Example 1 4-1
(WS15-30-144) 340 408 Example 2 4-3
(WS15-30-125) 240, 275, 338 403 Example 3 4-4
(WS15-30-137) 256, 332 421.5 Example 4 4-7
(WS15-30-183) 259, 376, 395 475.5 Example 5 4-8
(WS15-30-200) 275, 303, 344, 402 481.5 Example 6 4-11
(WS15-30-131) 270, 344 432 Example 7 4-12
(WS15-30-194) 259, 325, 377, 396 481.5 Example 8 4-15
(WS15-30-248) 250, 311, 401 492 Example 9 4-16
(WS15-30-229) 295, 334, 368 470 Example 10 4-17
(WS15-30-210) 259, 345 410.5 Example 11 4-18
(WS15-30-225) 256, 298, 332 383 Example 12 4-19
(WS15-30-218) 255, 291, 337 387 Example 13 4-20
(WS15-30-213) 244, 279, 338 434 Example 14 4-21
(WS15-30-211) 271, 343 432.5 Example 15 4-22
(WS15-30-228) 258, 281, 323, 375, 395 473.5 Example 16 4-25
(WS15-30-235) 267, 294, 336 429.5 Example 17 4-29
(WS15-35-001) 273, 332 422 Example 18 4-30
(WS15-35-002) 234, 269, 318 414 Example 19 4-32
(WS15-30-262) 269, 386, 405 465.5 Example 20 4-33
(WS15-30-271) 230, 265, 318 413

UV / VIS  And PL  Result -2 division compound UV (nm) * 1 PL (nm, room temperature) * 2 Example 21 4-35
(WS15-35-003) 244, 338 434 Example 22 4-36
(WS15-35-004) 250, 401 492 Example 23 4-41
(WS15-30-258) 285, 314, 378 460 Example 24 4-42
(WS15-30-270) 266 426.5 Example 25 4-46
(WS15-35-005) 256 416.5 Example 26 4-48
(WS15-35-006) 251, 375, 385 429.5 Example 27 4-52
(WS15-35-007) 276, 380, 410 424.5, 463.5 Example 28 4-53
(WS15-35-008) 259, 377, 396 481.5 Example 29 4-54
(WS15-35-009) 250, 411 482 Example 30 4-68
(WS15-30-266) 286, 411 434.5, 443.5 Example 31 4-70
(WS15-35-010) 273, 332 422 Example 32 4-71
(WS15-30-124) 274, 321 388.5, 420.5 Example 33 4-73
(WS15-30-127) 255 384.5 Example 34 4-74
(WS15-30-129) 256 416.5 Example 35 4-75
(WS15-30-146) 274, 330 389.5 Example 36 4-76
(WS15-30-133) 268 386.5 Example 37 4-77
(WS15-30-154) 261, 332, 375, 395 439.5 Example 38 4-78
(WS15-30-182) 286, 390, 411 434.5, 453.5 Example 39 4-81
(WS15-30-126) 269, 323 391 Example 40 4-82
(WS15-30-190) 261, 331, 375, 396 444.5 * 1: 1.0 x 10 -5 M in Methylene Chloride
* 2: 5.0 x 10 -6 M in Methylene Chloride

Device fabrication test example

2-TNATA is a hole injecting layer, NPB is a hole transporting layer, αβ-ADN is a host of a light emitting layer, Pyene-CN is a blue fluorescent dopant, Liq is an electron injecting layer, Al was used as the cathode. The structures of these compounds are shown below.

Figure 112015112931366-pat00064

Comparative Example: ITO / 2-TNATA (60 nm) / NPB (20 nm) / αβ-ADN: 10% Pyrene-CN (30 nm) / Alq 3 (30 nm) / Liq (2 nm) / Al (100 nm)

The 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: Pyrene-CN 10% (30 nm) / electron transport layer nm) / Al (100 nm) in this order. 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. The organic materials were deposited at a vacuum of 9 × 10 -7 Torr. Simultaneously, Pyrene-CN was deposited at 0.02 Å / sec on the basis of Liq and 0.18 Å / sec for αβ-ADN. sec. < / RTI > The electron transport layer material used in the experiment was Alq 3 . 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.

Figure 112015112931366-pat00065

≪ Test Examples 1 to 33 >

In the above comparative test example, devices were prepared in the same manner as in the Comparative Test Example except that each compound shown in Table 3 was used instead of Alq 3 .

Table 3 shows the electroluminescent characteristics of the organic luminescent devices prepared in the Comparative Test Examples and Test Examples 1 to 33.

division compound Driving voltage
[V] efficiency
[cd / A] life span
(%) Comparative Example Alq 3 6.60 5.10 91.78 Test Example 1 WS15-30-144 4.28 6.20 98.09 Test Example 2 WS15-30-125 3.81 7.71 78.13 Test Example 3 WS15-30-137 3.89 7.99 98.25 Test Example 4 WS15-30-183 3.97 7.86 96.34 Test Example 5 WS15-30-200 4.89 4.26 98.61 Test Example 6 WS15-30-131 4.56 5.28 98.32 Test Example 7 WS15-30-194 4.07 7.65 97.46 Test Example 8 WS15-30-248 3.97 7.62 97.50 Test Example 9 WS15-30-229 4.99 3.32 98.96 Test Example 10 WS15-30-210 4.24 6.71 98.75 Test Example 11 WS15-30-225 3.74 8.15 97.92 Test Example 12 WS15-30-218 3.87 8.28 98.25 Test Example 13 WS15-30-213 4.03 7.23 98.64 Test Example 14 WS15-30-211 4.09 7.19 98.72 Test Example 15 WS15-30-228 3.95 8.05 97.45 Test Example 16 WS15-30-235 4.02 7.51 98.00 Test Example 17 WS15-35-001 3.97 7.81 96.31 Test Example 18 WS15-35-002 3.83 6.81 95.12 Test Example 19 WS15-30-262 4.01 6.66 96.21 Experimental Example 20 WS15-30-271 4.26 6.39 98.46 Experimental Example 21 WS15-30-258 4.02 7.82 96.72 Experimental Example 22 WS15-30-270 3.93 7.79 95.14 Experimental Example 23 WS15-35-009 4.03 7.39 96.78 Experimental Example 24 WS15-30-266 4.12 6.83 96.34 Experimental Example 25 WS15-30-124 4.24 6.16 99.42 Experimental Example 26 WS15-30-127 4.87 8.28 95.89 Experimental Example 27 WS15-30-129 4.79 8.33 96.24 Experimental Example 28 WS15-30-146 4.66 6.25 97.73 Experimental Example 29 WS15-30-133 4.62 7.50 99.80 Experimental Example 30 WS15-30-154 4.30 8.48 96.72 Experimental Example 31 WS15-30-182 3.58 5.64 99.11 Experimental Example 32 WS15-30-126 4.65 7.64 97.45 Experimental Example 33 WS15-30-190 4.14 7.74 97.30

From the results shown in Table 3, specific pyridyl group-bonded pyrimidine derivative compounds according to the present invention can be used as a material for an organic material layer of organic electronic devices including organic light emitting devices, and organic electronic devices including organic light emitting devices using the same , Driving voltage, stability, and the like. Particularly, specific pyrimidine derivatives according to the present invention exhibited high efficiency characteristics because of their excellent balance of electron and electron transporting ability.

Claims (9)

A pyrimidine derivative to which a pyridyl group represented by the following formula (1) is bonded.
[Chemical Formula 1]
Figure 112017057311098-pat00066

Wherein Ar 1 and Ar 2 are each independently phenyl, biphenyl or naphthyl,
X 1 and X 2 are each independently CH or N, provided that one of X 1 and X 2 is N. delete delete The method according to claim 1,
Wherein the pyrimidine derivative represented by Formula 1 is a pyrimidine derivative bonded to a pyridyl group selected from the group consisting of Formula 4 below.
[Chemical Formula 4]
Figure 112017057311098-pat00067
 An organic electroluminescent device comprising a pyrimidine derivative having a pyridyl group bonded thereto according to any one of claims 1 to 4 6. The method of claim 5,
Wherein the pyridyl group-bonded pyrimidine derivative is used as an electron transport layer material. A first electrode, a second electrode, and at least one organic film disposed between the electrodes,
The organic film may be formed by a process wherein the pyridyl group of the first or fourth paragraph is bonded An organic electroluminescent device comprising a pyrimidine derivative. 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,
When the pyridyl group is bonded Wherein the pyrimidine derivative is contained in any one layer 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, and a light emitting layer constituting the organic film An electroluminescent device.
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KR102064993B1 (en) 2017-05-31 2020-01-10 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
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US20210217963A1 (en) 2018-10-12 2021-07-15 Lg Chem, Ltd. Organic light-emitting device
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004002297A (en) 2002-04-11 2004-01-08 Idemitsu Kosan Co Ltd New nitrogen-containing heterocyclic derivative and organic electroluminescent element using the same
US20140103306A1 (en) 2012-10-12 2014-04-17 Samsung Display Co., Ltd. Organic light-emitting diode, method of manufacturing the same, and method of forming material layer

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004002297A (en) 2002-04-11 2004-01-08 Idemitsu Kosan Co Ltd New nitrogen-containing heterocyclic derivative and organic electroluminescent element using the same
US20140103306A1 (en) 2012-10-12 2014-04-17 Samsung Display Co., Ltd. Organic light-emitting diode, method of manufacturing the same, and method of forming material layer

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