KR20140127705A - Pyridine-Pyrimidine derivatives and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to pyridine-pyrimidine derivatives represented by the following chemical formula 1 and an organic light emitting diode having excellent efficiency by comprising the same pyridine-pyrimidine derivatives in one or more organic layers. The pyridine-pyrimidine derivatives and the organic light emitting diode comprising the same according to the present invention are excellent in luminous efficiency and heat stability and applicable to all luminous layers ranging between red and blue phosphorescence, thereby being able to be used in various organic light emitting diodes for a flat panel display of a wall-mountable TV, lights, or a backlight of a display. [Chemical formula 1] In the chemical formula 1, R1 is anyone selected from the group comprised of phenyl, dibenzo[b,d]furanyl, and dibenzo [b,d]thienyl, and R2 is anyone selected from the group comprised of tert-butyl, trimethylsilanyl, phenyl, and mesityl.

Description

Pyridine-Pyrimidine Derivatives and Organic Electroluminescent Devices Including the Same -

The present invention relates to novel pyridine-pyrimidine derivatives having excellent light-emitting efficiency and thermal stability, and organic electroluminescent devices exhibiting excellent efficiency characteristics by incorporating them into one or more organic layers.

The organic electroluminescent device is a self-luminous type light emitting device, which has a simpler structure than other light emitting devices, has a simple manufacturing process, has a high response speed and low driving voltage, The applicability as a light source such as a billboard is increasing. Organic electroluminescence phenomenon has been limited in practical terms since it was announced by Curnee in 1969 (US Pat. No. 3,172,862). However, the organic electroluminescent device which overcome the existing problems by the researchers of Eastman Kodak Company in 1987 Has developed rapidly since then.

Generally, an organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and at least one organic layer between the two electrodes.

In this case, the organic electroluminescent device may include, as an organic layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron transport layer (ETL) And may further include an electron injection layer (EIL), and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the light emitting property of the light emitting layer. The organic electroluminescent device including all of these organic layers has a stacked structure in the order of anode / hole injecting layer / hole transporting layer / electron blocking layer / light emitting layer / hole blocking layer / electron transporting layer / electron injecting layer / cathode.

When an electric field is applied to the organic electroluminescent device having such a structure, the holes injected from the anode and the electrons injected from the cathode are recombined to form an electron-hole pair exciton, Light is emitted as it is transmitted. The lifetime of the stacked organic electroluminescent device is related to the electrochemical stability and the thin film stability of the material.

For example, when a light emitting material having poor heat stability is used, crystallization of the material occurs at a high temperature or at a driving temperature, and the lifetime of the device is shortened. An anthracene derivative has been used for a typical organic electroluminescence device as a light emitting layer, a hole transporting layer, an electron transporting layer, and the like. As a typical example, 9,10-di (naphthalen-2-yl) anthracene is used as a host material for a light emitting layer. However, it is easily crystallized as the temperature of the device rises, shortening the lifetime of the device. In order to overcome such shortcomings, various types of materials have been developed. However, until now, characteristics such as required luminous efficiency, driving stability, and life span are not sufficiently satisfied.

Accordingly, the present inventors have found that pyridine-pyrimidine derivatives can solve the above problems while studying a novel compound having excellent luminescence efficiency and thermal stability, thereby completing the present invention.

An object of the present invention is to provide a pyridine-pyrimidine derivative which is excellent in luminous efficiency and thermal stability and can be applied to all the light emitting layers up to red and blue phosphorescence, and an organic light emitting device including the pyridine-pyrimidine derivative in the organic layer.

In order to accomplish the above object, the present invention provides a compound represented by the following Formula 1:

[Chemical Formula 1]

Wherein R ₁ is selected from the group consisting of phenyl, dibenzo [b, d] furanyl and dibenzo [b, d] thienyl Which is selected,

R ₂ is any one selected from the group consisting of tert-butyl, trimethylsilanyl, phenyl, and mesityl.

The compound of formula (1) is a structure in which an asymmetric carbazole group, dibenzofuranyl group or dibenzothienyl group is bonded or substituted with respect to the structure of 2- (phenylsulfonyl) pyridine.

Preferably, the compound is any one of compounds represented by the following general formula (1a) or (1b).

[Formula 1a]

[Chemical Formula 1b]

Also preferably, the R ₂ is substituted at the position 6 or 7 of the carbazole.

[Chemical Formula 1]

On the other hand, the amorphous thin film is formed into a crystalline form due to the temperature (usually less than 100 캜) which is raised at the time of driving the device, and the lifetime is drastically decreased. The thin film stability means the uniformity of the film and the interface stability with the other layer materials, and affects the driving stability (stable current density, etc.).

Heat resistance in OLED materials is related to melting point and glass transition temperature. This heat resistance is directly related to molecular firmness and molecular weight. That is, the higher the molecular weight, the better the heat resistance. Also, when a substituent capable of free rotation at a similar molecular weight or a molecule containing a linear aliphatic hydrocarbon substituent is introduced, the heat resistance tends to decrease.

Representative examples of the compound of formula (1) are as follows.

(1),

(2),

(3),

(4),

(5),

(6),

(7),

(8),

(9),

(10),

(11),

(12),

(One),

(2),

(3),

(4),

(5),

(6),

(7),

(8),

(9),

(10),

(11),

(12),

(13),

(14),

(15),

(13),

(14),

(15),

(16),

(17),

(18),

(19),

(20),

(21),

(22),

(23),

(16),

(17),

(18),

(19),

(20),

(21),

(22),

(23),

(24),

(25),

(26),

(27),

(28),

(29),

(30),

(31),

(24),

(25),

(26),

(27),

(28),

(29),

(30),

(31),

(32),

(33),

(32),

(33),

(34),

(35),

(36),

(37),

(38),

(39),

(40),

(41).

(42),

(43),

(44),

(45),

(46),

(47),

(48),

(49), 및

(50).

(34),

(35),

(36),

(37),

(38),

(39),

(40),

(41).

(42),

(43),

(44),

(45),

(46),

(47),

(48),

(49), and

(50).

Also, as an example of the present invention, there is provided a process for producing a compound represented by the above formula (1) In the following Reaction Scheme 1, the definitions of R ₁ and R ₂ are as described above.

[Reaction Scheme 1]

Step 1 is a step of reacting a compound represented by formula (1-1) with a carbazole compound to prepare a compound represented by formula (1-2). In the above step, a solution prepared by mixing a compound of the formula 1-1, tetrakis (triphenylphosphine) palladium (0), 3- (9H-carbazol-9-yl) phenylboronic acid and tetrahydrofuran in a mixture of potassium carbonate And water.

Step 2 is a step of reacting a compound represented by formula (1-2) with a compound represented by formula (1-6) to prepare a compound represented by formula (1). In the above step, it is preferable to add potassium carbonate and water to a solution of the compound of the formula 1-2, tetrakis (triphenylphosphine) palladium (0), 1-6 compound and tetrapyridofuran to react.

Also, as an example of the present invention, there is provided a process for producing an intermediate compound represented by the above Chemical Formula 1-6 as shown in Reaction Scheme 2 below. In the following Reaction Scheme 2, R ₁ And The definition of R < ₂ > is as described above.

[Reaction Scheme 2]

Step 1 is a step of reacting a compound represented by Formula 1-3 with a carbazole compound to prepare a compound represented by Formula 1-4. In the above step, it is preferable to add potassium carbonate and carbazole to the mixed solution of the compound of Formula 1-3, palladium (0) diacetate, tri-tert-butylphosphine and o-xylene to perform the reaction.

Step 2 is a step of reacting a compound represented by Formula 1-4 with en-bromosuccinimide and dimethylformamide to prepare a compound represented by Formula 1-5.

Step 3 is a step of reacting a compound represented by the formula (1-5) with n-butyl lithium and triethyl borate to prepare a compound represented by the formula (1-6). In this step, tetrahydrofuran is preferably used as a solvent.

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. At this time, the organic layer essentially includes a light emitting layer and may include a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, or a laminate thereof in addition to the light emitting layer.

The organic electroluminescent device according to the present invention is characterized in that at least one layer of the organic thin film layer is represented by the above formula (1), wherein the organic thin film layer comprises a single layer or a plurality of organic thin film layers sandwiching a cathode and an anode, An organic electroluminescent device comprising an organic electroluminescent device comprising a compound.

The organic electroluminescent device of the present invention comprises a positive electrode, a negative electrode, and a single layer or multilayer organic layer containing at least one luminescent layer between the two electrodes, wherein at least one layer of the organic layer comprises a novel compound of the formula . For example, a multilayer organic electroluminescent device is laminated from the bottom in a multilayer structure of a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode.

The substrate, the anode, and the cathode of the organic electroluminescent device according to the present invention are made of a material used in a conventional organic electroluminescent device, and each of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, , Materials conventionally used, or mixtures thereof.

In particular, in the case of the light emitting layer, the compound of the formula (1) of the present invention can be used or can be used together with other known light emitting dopant materials or host materials used as a light emitting host material or a dopant material. When the compound of the formula (1) is used as a single luminescent material or a host material, it may be added in an amount of 100 to 80% by weight relative to the light emitting layer, and when it is used as a dopant material, it may be added in an amount of 0.01 to 20% have. Specific examples of the light emitting material, the host material or the dopant material which can be used in the light emitting layer together with the compound of the formula (1) include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, klysene, fluorene, perylene, But are not limited to, phthalocyanine, phthaloyl perylene, phthalo perylene, perinone, phthalo perinone, naphthalo perlinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, Anthraquinone metal complexes, cyclopentadiene, quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline metal complexes, imines, diphenylethylene, vinyl anthracene, diaminocarbazole, pyran, thiopyran, polymethine, Quinacridone, rubrene, fluorescent dyes, and mixtures thereof, but are not limited thereto. When a dopant material is selected, it is preferable to select a dopant having a bandgap equal to or less than the bandgap of the host material while having high efficiency of fluorescence or phosphorescence.

Each of the layers constituting the organic electroluminescent device may be formed by any of a conventional film forming method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film forming method such as spin coating, immersion coating, . The film thickness is not particularly limited, but if the film thickness is too thick, a high applied voltage is required to obtain a constant light output, which leads to poor efficiency. If the film thickness is too thin, pinholes or the like may be generated, Sufficient light emission luminance can not be obtained. A typical film thickness is preferably in the range of 5 nm to 10 mu m, more preferably in the range of 50 nm to 400 nm.

The pyridine-pyrimidine derivative according to the present invention and the organic electroluminescence device including the same can be applied to all the light emitting layers ranging from red to blue phosphors with excellent luminous efficiency and thermal stability. A backlight of a display, and the like.

Hereinafter, the present invention will be described in more detail with reference to Examples. These embodiments are only for describing the present invention more specifically, and the scope of the present invention is not limited by these examples.

Example  One

The compound of Example 1 was prepared by the following reaction scheme.

1) Synthesis of intermediate 1-2

(7 g), tetrakis (triphenylphosphine) palladium (0) (1.0 g) and 3- (9H-carbazol-9-yl) phenylboronic acid 10.6 g) and tetrahydrofuran (140 ml) were added, and the mixture was stirred in an argon atmosphere at room temperature for 1 hour. Potassium carbonate (12.8 g) and water (70 ml) were added to the mixed solution, and the mixture was refluxed for 12 hours while heating to about 70 캜. After completion of the reaction, the mixture was cooled to room temperature, and the reaction solution was separated by layer separation, and the organic layer was washed twice with water. The obtained organic layer was dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent. The material formed by concentration was subjected to column separation using dichloromethane and hexane to obtain 5.3 g of intermediate 1-2.

2) Example  1 < / RTI >

(7 g), tetrakis (triphenylphosphine) palladium (0) (1.0 g) and (9-phenyl-9H-carbazol-3-yl) boronic acid 5.6 g) and tetrahydrofuran (140 ml) were added, and the mixture was stirred in an argon atmosphere at room temperature for 1 hour. Potassium carbonate (6.7 g) and water (40 ml) were added to the mixture, and the mixture was refluxed for 12 hours while being heated to about 70 캜. After completion of the reaction, the mixture was cooled to room temperature, and the reaction solution was separated by layer separation, and the organic layer was washed twice with water. The obtained organic layer was dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent. 5.1 g of the compound of Example 2 was obtained through column separation using dichloromethane and hexane.

(1H, m), 7.63-7.50 (11H, m), 7.33-7.25 (4H, m) (8H, m) 200 MHz ¹ H-NMR chemical shift (隆), CDCl ₃ )

Example  2

The compound of Example 2 was prepared by the following reaction scheme.

1) Synthesis of intermediate 1-2

The compound of Intermediate 1-2 was synthesized by the same method as described above.

2) Synthesis of intermediate 2-6

Intermediate 2-6 was prepared by the following synthesis method.

2-a) Synthesis of intermediate 1-4

1-3 compound (5 g), palladium (0) diacetate (0.04 g), tri-tert-butylphosphine (0.23 g) and o-xylene (100 ml) were placed in a 250 ml three- And the mixture was stirred for 1 hour in an atmosphere. Potassium carbonate (7.9 g) and carbazole (3.8 g) were added to the mixed solution, followed by stirring at 120 ° C for 8 hours. Water was added, and the mixture was extracted with ethyl acetate, and the water was removed. The resulting material was subjected to column separation using dichloromethane and hexane to obtain 5.6 g of an intermediate 1-4 compound.

2-b) Synthesis of intermediate 1-5

To a 250 ml three-necked round bottom flask, 1-4 compounds (6 g), enbromosuccinimide (3.0 g) and dimethylformamide (60 ml) were added and reacted at 40 ° C for 3 hours. 20 ml of water was added, , The solid material was filtered off with a filter paper and then subjected to column separation using dichloromethane and hexane to obtain 5.2 g of an intermediate compound 1-5.

2-b) Synthesis of intermediate 2-6

1-5 compound (10 g) was dissolved in purified tetrahydrofuran (120 ml) into a 250 ml three-neck round bottom flask and stirred for 30 minutes at -78 ° C and argon atmosphere. N-butyl lithium (14 ml) of 2 molar concentration was slowly added dropwise to the mixed solution in the same atmosphere, followed by stirring for 1 hour. To this reaction solution, triisopropyl borate (5.9 ml) was slowly added dropwise at the same temperature, stirred for 2 hours, and then stirred at room temperature for 12 hours. After completion of the reaction, water was added thereto, and the mixture was stirred for 15 minutes. To the solution was added 2N hydrochloric acid to pH 5, followed by stirring for 4 hours. The solid material was filtered off with a filter paper using hexane to obtain 5 g of an intermediate 2-6 compound.

3) Example  2 < / RTI >

1-2 (7 g), tetrakis (triphenylphosphine) palladium (0) (0.56 g), 1-6 (7.6 g) and tetrahydrofuran (120 ml) were placed in a 250 ml three- And the mixture was stirred for 1 hour in an atmosphere. Potassium carbonate (6.7 g) and water (25 ml) were added to the mixture, and the mixture was refluxed for 12 hours while heating to about 70 캜. After completion of the reaction, the mixture was cooled to room temperature, and the reaction solution was separated by layer separation, and the organic layer was washed twice with water. The obtained organic layer was dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent. 5.1 g of the compound of Example 2 was obtained through column separation using dichloromethane and hexane.

(9H, m), 7.38-7.89 (9H, m), 7.80 (1H, s) 7.25 (6H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  3 to Example  50

The compounds of Examples 3 to 50 were obtained by carrying out the same processes as in Example 1 except for changing the method described in Example 1 and the compound of Intermediate 1-5. NMR data of each example is shown below.

Example  3

(2H, m), 8.20-8.12 (4H, m), 8.03 (2H, 1H, d), 7.94-7.89 (3H , m), 7.73-7.25 (15H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  4

(3H, m), 8.36-8.28 (3H, m), 8.20 (2H, s), 8.12-7.94 (3H, m), 7.63 7.45 (11H, m), 7.33-7.25 (3H, m), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  5

(9H, m), 7.38-7.89 (9H, m), 7.80 (1H, s) 7.25 (5H, m), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  6

(1H, s), 7.66-7.25 (1H, m), 1.35 (1H, 9H, s) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  7

(1H, s), 9.32 (1H, s), 9.00 (2H, s), 8.69-8.55 (3H, m), 8.30-7.94 (4H, m) 0.25 (9H , s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  8

(6H, m) 0.25 (1H, m), 9.22 (1H, s), 9.00 (2H, s), 8.69-8.55 (3H, m), 8.30-7.77 9H, s) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  9

9.22 (1H, s), 9.00 (2H, s), 8.69-8.55 (3H, m), 8.30-7.89 (9H, m), 7.77-7.25 (15H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ) , CDCl 3)

Example  10

(1H, s), 7.69-7.25 (18H, m) (200 MHz, ¹ H), 9.22 (1H, s), 9.00 (2H, s), 8.69-8.55 (3H, m), 8.30-7.87 H-NMR chemical shift (δ) , CDCl 3)

Example  11

M), 8.30-8.28 (2H, m), 8.20 (2H, s), 8.12-7.63 (11H, m), 7.54-8. 7.25 (14H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  12

M) (200 MHz ¹ H-NMR chemical shift (隆 (CDCl 3), 隆 (CDCl 3) ), CDCl ₃₎

Example  13

(1H, s), 7.69-7.45 (10H, m), 7.33-7.87 (1H, 7.25 (3H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  14

M), 8.30-8.28 (2H, m), 8.20 (2H, s), 8.12-7.63 (11H, m), 7.54-8. 7.50 (4H, m), 7.38-7.25 (5H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3 )

Example  15

M), 8.20 (2H, s), 8.12-7.63 (2H, m), 8.30 11H, m), 7.54-7.50 (4H , m), 7.38-7.25 (5H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (隆), CDCl ₃ )

Example  16

M), 8.20 (2H, s), 8.12 (2H, s), 8.69-8.55 (3H, m), 8.45 d), 8.03-7.94 (5H, m ), 7.63-7.47 (9H, m), 7.33-7.25 (4H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  17

M), 7.63 (1H, d), 9.22 (1H, s), 9.00 (2H, s), 8.69-8.55 (3H, m), 8.45 7.49 (9H, m), 7.33-7.25 (4H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  18

(2H, d), 7.63-7.45 (9H, m), 7.33-7. 9 (2H, s) 7.25 (5H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  19

(9H, m), 7.33 (2H, s), 9.22 (1H, s), 9.00 (2H, s), 8.69-8.28 7.25 (3H, m), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  20

(9H, m), 7.33-7.28 (2H, m), 9.22 (1H, s), 9.00 7.25 (3H, m), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  21

(1H, d), 7.63 (1H, s), 9.22 (1H, s), 9.00 (2H, s), 8.60-8.49 (3H, m), 8.35-8.30 7.45 (9H, m), 7.33-7.25 (3H, m), 7.03 (1H, d), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  22

M), 8.20 (2H, s), 8.12 (1H, s), 8.30-8.55 (3H, m), 8.45 m), 0.25 (9H, s) (200MHz, ¹ H-NMR, CDCl 3) d), 8.03-7.94 (5H, m), 7.77 (1H, s), 7.61-7.47 shift (隆), CDCl ₃ )

Example  23

M), 8.30 (2H, s), 8.05-7.94 (2H, s), 9.22 (1H, s), 9.00 6H, m), 7.77 (1H , s), 7.61-7.47 (8H, m), 7.33-7.25 (4H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3 )

Example  24

M), 7.94 (1H, s), 9.22 (1H, s), 9.00 (2H, s), 8.61-8.52 (4H, m), 8.30 d), 7.63-7.45 (10H, m ), 7.33-7.22 (4H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  25

(2H, m), 8.20 (2H, m), 9.22 (1H, s), 9.00 s), 8.12 (1H, d ), 8.03-7.87 (6H, m), 7.77 (1H, s), 7.69-7.63 (2H, m), 7.54-7.25 (14H, m) (200MHz 1 H-NMR chemical shift (隆), CDCl ₃ )

Example  26

(2H, m), 8.20 (2H, m), 9.22 (1H, s), 9.00 s), 8.12-7.87 (7H, m ), 7.77 (1H, s), 7.69-7.63 (2H, m), 7.54-7.25 (14H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3 )

Example  27

M), 7.94 (2H, d), 8.21-8.20 (3H, m), 8.13-8.10 (3H, 1H, d), 7.63-7.25 (18H , m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  28

(2H, m), 8.20 (2H, s), 8.12-7.87 (2H, (2H, m), 7.77 (1H, s), 7.69-7.63 (2H, d), 7.54-7.47 (6H, m), 7.33-7.29 s), 2.34 (3H, s) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  29

(2H, m), 8.20 (2H, s), 8.12-7.87 (2H, (2H, m), 7.77 (1H, s), 7.69-7.63 (2H, d), 7.54-7.49 (6H, m), 7.33-7.29 s), 2.34 (3H, s) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  30

(1H, d), 7.63-7.45 (2H, s), 9.22 (1H, s), 9.00 3H, s) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ ), 7.33-7.29 (3H, m)

Example  31

M), 7.80-7.89 (3H, m), 7.80 (1H, s), 7.66-8.55 (3H, m) 7.50 (7H, m), 7.38-7.25 (7H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  32

(2H, m), 7.30-7.15 (4H, m), 7.92-7.15 200 MHz ¹ H-NMR chemical shift (隆), CDCl ₃ )

Example  33

(1H, m), 7.63-7.94 (5H, m), 7.63-7.30 (2H, m) 7.47 (7H, m), 7.33-7.25 (5H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  34

(3H, m), 8.35-8.30 (3H, m), 8.21-8.12 (5H, m), 7.94-7.80 (3H, m) 7.66-7.50 (7H, m), 7.38-7.25 (5H, m), 7.03 (1H, d), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  35

(3H, m), 8.35-8.30 (3H, m), 8.21-8.12 (5H, m), 7.94-7.89 7.73 (1H, s), 7.66-7.25 (11H, m), 7.03 (1H, d), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  36

M), 8.35-8.30 (3H, m), 8.21-8.12 (5H, m), 7.98-7.94 (4H, m), 9.22 (1H, s), 9.00 7.63 (1H, d), 7.54-7.47 (6H, m), 7.33-7.25 (3H, m), 7.03 (1H, d), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl ₃₎

Example  37

(2H, s), 9.22 (1H, s), 9.00 (2H, s), 8.61-8.52 (4H, m), 8.30 2H, d), 7.80 (1H , s), 7.66-7.62 (4H, m), 7.54-7.50 (4H, m), 7.38-7.22 (6H, m), 0.25 (9H, s) (200MHz 1 H- NMR chemical shift (δ), CDCl 3)

Example  38

(2H, s), 9.22 (1H, s), 9.00 (2H, s), 8.61-8.52 (4H, m), 8.30 3H, d), 7.73 (1H , s), 7.66-7.62 (3H, m), 7.54-7.22 (10H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3 )

Example  39

(2H, s), 9.22 (1H, s), 9.00 (2H, s), 8.60-8.45 (5H, m), 8.30 4H, m), 7.63-7.62 (2H , m), 7.54-7.47 (6H, m), 7.33-7.22 (4H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl ₃₎

Example  40

M), 8.14-8.10 (3H, m), 8.94 (2H, d) 7.89 (2H, d), 7.80 (1H, s), 7.66-7.25 (18H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  41

M), 8.14-8.10 (3H, m), 8.94 (2H, d) 7.89 (3H, m), 7.73 (1H, s), 7.66-7.25 (17H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  42

(3H, m), 7.94 (1H, m), 9.22 (1H, s), 9.00 (2H, s), 8.60-8.45 7.89 (4H, m), 7.63-7.62 (2H, m), 7.66-7.25 (14H, m) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  43

(2H, d), 8.80 (2H, d), 8.21-8.10 (6H, m), 7.94-7.89 1H, s), 7.66-7.50 (8H , m), 7.38-7.25 (5H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (隆), CDCl ₃ )

Example  44

M), 7.73 (2H, d), 8.21-8.10 (6H, m), 7.94-7.89 (3H, 1H, s), 7.63-7.25 (12H , m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  45

(2H, s), 8.60-8.45 (4H, m), 8.30 (2H, d), 8.21-8.10 (6H, m), 7.98-7.94 7.47 (8H, m), 7.33-7.25 (3H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3 )

Example  46

(2H, d), 8.20-7.94 (10H, m), 7.63 (1H, s), 9.60 d), 7.54-7.49 (6H, m), 7.33-7.25 (5H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  47

M), 8.21-8.20 (3H, m), 8.12-7.94 (6H, m), 8.35-8.30 (3H, m) 7.63 (1H, d), 7.54-7.49 (6H, m), 7.33-7.25 (3H, m), 7.03 (1H, d), 1.35 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl ₃₎

Example  48

(2H, s), 8.13-7.94 (7H, m), 7.63-7.62 (2H, 2H, m), 7.54-7.49 (6H , m), 7.33-7.22 (4H, m), 0.25 (9H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Example  49

M), 8.16-7.94 (7H, m), 7.63-8.45 (2H, m), 9.22 (1H, s), 9.00 7.62 (2H, m), 7.54-7.25 (14H, m) (200 MHz ¹ H-NMR chemical shift (?), CDCl ₃ )

Example  50

(8H, m), 7.33-7.94 (8H, m), 9.22 (1H, s), 9.00 7.25 (3H, m), 6.97 (2H, s), 3.01 (6H, s), 2.34 (3H, s) (200MHz 1 H-NMR chemical shift (δ), CDCl 3)

Experimental Example

Experimental Example  One: Example  Preparation of organic electroluminescent device using

An ITO transparent electrode with a thickness of 100 nm was cut to a size of 40 mm × 40 mm × 0.7 m. The substrate was ultrasonically cleaned in distilled water for 10 minutes and washed twice in distilled water for 10 minutes.

After the distilled water was washed, solvents such as isopropyl alcohol, acetone and methanol were sequentially ultrasonically washed and dried. After the wet refining, the substrate was dry-cleaned using oxygen / argon plasma, and then a glass substrate having a transparent electrode line was mounted on a substrate holder of a vacuum evaporation apparatus. On the surface of the ITO side on which the transparent electrode line was formed, DNTPD of a compound (N ¹ , N ^{1 '} - (biphenyl-4,4'-diyl) bis (N ¹ -phenyl-N ⁴ , N ⁴ -dim-tolylbenzene- Lt; RTI ID = 0.0 > vacuum / vacuum < / RTI >

(A)

(N ⁴ , N ^{4 '} -di (naphthalen-1-yl) -N ⁴ , N ^4' -diphenylbiphenyl-4,4 '-diamine was formed by vacuum deposition at 20 nm.

[Chemical Formula B]

(4- (4aH-carbazol-9 (4bH, 8aH, 9aH) -yl) phenyl, which is capable of preventing electrons from easily flowing into the hole transport layer on the layer of the compound of Formula (B) (9H-carbazol-9-yl) benzenamine) was vacuum-deposited to a thickness of 10 nm.

≪ RTI ID = 0.0 &

A compound represented by the following formula (D) as a blue dopant was mixed and vapor-deposited at a concentration of 5% together with the compound of Example 1 as a light emitting host on the layer of the compound of the formula (C) to form a light emitting layer of 30 nm in thickness.

[Chemical Formula D]

A compound of the following formula (E) serving as an electron injecting and transporting layer was vacuum deposited on the light emitting layer to a thickness of 30 nm.

(E)

Lithium fluoride (LiF) with a thickness of 0.7 nm and aluminum with a thickness of 120 nm were sequentially deposited on the electron injection and transport layer to form a cathode. The resulting organic light emitting device was measured at a voltage of 6 V to form a current density of 0.62 mA / cm 2. At this time, a luminance of 164 cd / m 2 corresponding to x = 0.145 and y = 0.340 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 26.4 cd / A.

Experimental Example  2

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the compound of Example 1 of the present invention, which is a luminescent host material, was used as a luminescent host material.

The organic electroluminescent device manufactured as described above was measured at a voltage of 6 V and a current density of 0.03 mA / cm 2 was formed. At this time, x = 0.151 and y = 0.327 on the basis of the CIE color coordinates of 1931, A spectrum close to pure blue was observed and the efficiency was 30.9 cd / A.

Experimental Example  3: Comparative Example

An organic electroluminescence device was prepared in the same manner as in Experimental Example 1, except that the compound represented by the following formula (E) was used as a luminescent host material instead of the host material of Example 1 of the present invention.

[Chemical Formula F]

The organic electroluminescent device manufactured as described above was measured at a voltage of 6 V and a current density of 0.13 mA / cm 2 was formed. The current density was 23 cd / m 2 corresponding to x = 0.147 and y = 0.332 on the basis of 1931 CIE color coordinates. A spectrum close to pure blue was observed and the efficiency was 18.1 cd / A.

Claims (6)

A compound represented by the following formula (1):
[Chemical Formula 1]

Wherein R ₁ is any one selected from the group consisting of phenyl, dibenzo [b, d] furanyl and dibenzo [b, d] thienyl,
R ₂ is any one selected from the group consisting of tert-butyl, trimethylsilanyl, phenyl, and mesityl.
The method according to claim 1,
Wherein the compound is any one of compounds represented by the following general formula (1a) or (1b):
[Formula 1a]

[Chemical Formula 1b]

.
The compound of claim 1, wherein R ₂ is substituted at position 6 or 7 of the carbazole.
The compound according to claim 1, wherein the compound is

(One),

(2),

(3),

(4),

(5),

(6),

(7),

(8),

(9),

(10),

(11),

(12),

(13),

(14),

(15),

(16),

(17),

(18),

(19),

(20),

(21),

(22),

(23),

(24),

(25),

(26),

(27),

(28),

(29),

(30),

(31),

(32),

(33),

(34),

(35),

(36),

(37),

(38),

(39),

(40),

(41).

(42),

(43),

(44),

(45),

(46),

(47),

(48),

(49), and

(50). ≪ / RTI >
An organic electroluminescent device comprising a compound according to any one of claims 1 to 4.
Wherein at least one layer of the organic thin film layer is an organic electroluminescent element containing the organic electroluminescent element of claim 5, wherein the organic electroluminescent element comprises a single layer or a plurality of organic thin film layers sandwiched between a cathode and an anode, Light emitting element.