KR101774900B1 - Preparing method of aromatic triazine derivatives for organic electroluminescent device - Google Patents

Abstract

상기 [화학식 1] 에서, 치환기 R₁은 ‘퀴놀린’ 또는 ‘3-(나프탈렌-8-일)피리딘’이고, R₂는 ‘9,10-디(나프탈렌-2-일)안트라센’ 또는 ‘9,10-디페닐안트라센’ 이다.The present invention relates to a novel process for producing an aromatic triazine derivative for an organic electroluminescent device, and more particularly, to a process for producing an aromatic triazine derivative for an organic electroluminescent device which can be used as a hole injecting material, a hole transporting material and an electron injecting material of an organic electroluminescent device, The present invention relates to a process for producing an aromatic triazine derivative represented by the following formula (1), which is useful for use as a material.
[Chemical Formula 1]

The Formula 1 in the substituent R ₁ is the "quinoline" or "3- (naphthalen-8-yl) pyridine", R ₂ is, 9,10-di (naphthalene-2-yl) anthracene, "or" 9 , 10-diphenylanthracene ".

Description

TECHNICAL FIELD The present invention relates to an aromatic triazine derivative for organic electroluminescent devices,

The present invention relates to a process for producing an aromatic triazine derivative for an organic electroluminescent device, and more specifically, it can be used as a hole injecting material, a hole transporting material and an electron injecting material of an organic electroluminescent device, To a process for preparing an aromatic triazine derivative useful in the following.

BACKGROUND ART An organic electroluminescent device is a self-luminescent device that emits light when a current flows through a fluorescent organic compound. The organic electroluminescent device is also called an organic light emitting diode (OLED) or organic electroluminescence (EL) the device can be formed on a flexible plastic substrate and has excellent display performance such as a wide viewing angle, a high-speed response, and a high contrast, and has been attracting attention as a device for a flat display.

The structure of the organic electroluminescent device generally has a structure in which a first electrode (anode), a hole injecting layer, a hole transporting layer, a light emitting layer, an electron injecting layer, an electron transporting layer, and a second electrode are sequentially stacked on a transparent substrate . Therefore, when electrons and holes are injected into the light emitting layer through the electron injection layer and the hole injection layer, the electrons and the holes are combined with each other to generate excitons, and the excitons are excited ) To the ground state and emits light.

If the interface state between the layers is unstable, the organic electroluminescent device may have a bad influence on the light emitting performance due to heat or an electric field generated inside the device. In addition, There may arise a problem that the driving voltage of the device is increased due to the energy barrier existing between each interface.

Therefore, in order to improve the performance of the organic electroluminescent device, it is important to stabilize the interfacial state between the respective layers, and to minimize the factors that become energy barriers in the process of injecting holes into the light emitting layer. Since each layer constituting the organic electroluminescent device is mainly applied by a vapor deposition method, it is necessary to use a material having high heat resistance so as to withstand high temperature deposition. In particular, when a material having a low glass transition temperature is used as the hole transport layer, The uniformity of the surface of the thin film becomes poor, thereby shortening the lifetime of the device.

Efforts have been made to develop new organic compounds having physical properties capable of improving the performance of organic electroluminescent devices because of their excellent injection and migration ability of electrons and holes according to the technical requirements.

For example, Japanese Patent No. 4,476,594 (Jun. 2010) discloses that the transport layer is made of N, N, N ', N'-tetraphenyl-4,4'- diaminophenyl, N, N'- (3-methylphenyl) -4,4'-diaminobiphenyl, and Korean Patent No. 10-0806812 (Feb. 18, 2008) discloses an organic EL device comprising only an organic compound such as An organic EL device having a laminated structure including a light emitting layer and an electron transporting layer, wherein the electron transporting layer comprises a mixture of a first layer adjacent to the light emitting layer and a second layer adjacent to the cathode, Is introduced. Korean Patent No. 10-0672301 (Jan. 16, 2007) discloses a novel organic luminescent material having an electron transporting property and a hole transporting property under an organic luminescent electric field, which is used as an electron transporting layer, a hole transporting layer and a luminescent layer, Emitting device.

However, the device disclosed in the above-mentioned Japanese Patent No. 4,476,594 has a problem in that the electric resistance is not satisfactory even though it is conductive. The device manufactured in the multi-layer structure as in the Korean Patent No. 10-0806812, Structure and surface treatment conditions, it is difficult to manufacture a consistent device. The Korean Patent No. 10-0672301 discloses that the desired content of the amorphous compound due to heat instability in the deposition process for manufacturing the device It is difficult to maintain.

Japanese Patent No. 4,476,594 (June 6, 2010) Korean Patent No. 10-0806812 (Feb. 18, 2008) Korean Patent No. 10-0672301 (January 16, 2007)

As described above, in order to improve the efficiency of the organic electroluminescent device, a variety of compounds having various functions have been mixed and used. However, due to the interaction between the luminescent material and each organic compound, the luminous efficiency and lifetime of the device are limited Therefore, the development of new organic compounds that can be used as host materials, light-emitting doping materials, charge injecting and transporting materials, and the like, has continued to be demanded.

Accordingly, it is an object of the present invention to provide an organic compound used for an organic electroluminescent device which improves the mobility (cm ² / Vs) of holes or electrons in a given electric field (V / cm) And a method for producing a novel aromatic triazine derivative capable of enhancing the luminous efficiency of the organic electroluminescent device and prolonging the lifetime by stabilizing the interface between the layers and thereby minimizing the energy barrier generated in the process of injecting holes and holes to provide a

Another object of the present invention is to provide an intermediate useful for preparing the aromatic triazine derivative.

The aromatic triazine derivative for organic electroluminescent device according to the present invention is characterized by being represented by the following formula (1).

[Chemical Formula 1]

The Formula 1 in the substituent R ₁ is the "quinoline" or "3- (naphthalen-8-yl) pyridine", R ₂ is, 9,10-di (naphthalene-2-yl) anthracene, "or" 9 , 10-diphenylanthracene ".

The production intermediate of an aromatic triazine derivative for an organic electroluminescent device according to the present invention is characterized by being represented by the following formula (2).

(2)

In the above formula (2), the substituents X ₁ and X ₂ each represent any one of fluorine, chlorine, bromine and iodine.

The aromatic triamine derivative of the formula (1) according to the present invention contains pyridine having a hole-blocking function and triazine having an electron-transporting function, And can be usefully used as a transportation material.

In particular, since the aromatic triazine derivative has LUMO (lowest unoccupied molecular orbital) similar to that of a cathode, injection of electrons from the cathode is facilitated, driving voltage is reduced, quantum efficiency and power efficiency are improved, Thereby improving the performance and lifetime of the device.

The compound of formula (2) is very useful as an intermediate for preparation of aromatic triamine derivatives of formula (1).

1 is a graph showing a change in current density (mA / cm 2) along an applied voltage (X axis) with respect to an electroluminescent device using a conventional electron transport layer material,
2 is a graph showing a change in current density (mA / cm 2) along an applied voltage (X axis) with respect to an electroluminescent device using an aromatic triazine derivative of the present invention as an electron transport layer,
3 is a graph showing a change in emission luminance (nit, cd / cm, Y axis) according to current density (mA / cm; X axis) of an electroluminescent device using a conventional electron transporting layer material,
4 is a graph showing changes in emission luminance (nit, cd / cm, Y axis) according to current density (mA / cm; X axis) of an electroluminescent device using an aromatic triazine derivative of the present invention as an electron transport layer .

Specific examples of the aromatic triazine derivatives of the formula (1) according to the present invention are as shown in the following formulas (1-1) to (1-6).

3- (2- (4- (9,10- Di (naphthalene-3-yl) anthracene -3 days) Phenyl ) -2H- Benzo [d] [1,2,3] triazole -6-yl) quinoline

[Formula 1-1]

4- (2- (4- (9,10- Di (naphthalene-3-yl) anthracene -3 days) Phenyl ) - (2H- Benzo [d] [1,2,3] triazol-6-yl) isoquinoline

[Formula 1-2]

2- (4- (9,10- Di (naphthalene-3-yl) anthracene Yl) -5- (1-pyridin-3-yl) naphthalen-4-yl) Benzo [d] [1,2,3] triazole

[Formula 1-3]

3- (2- (4- (9,10- Diphenylanthracene -3 days) Phenyl ) -2H- Benzo [d] [1,2,3] triazole -6-yl) quinoline

[Formula 1-4]

4- (2- (4- (9,10- Diphenylanthracene -3 days) Phenyl ) -2H- Benzo [d] [1,2,3] triazole -6-yl) isoquinoline

[Formula 1-5]

2- (4- (9,10- Diphenylanthracene Yl) -5- (1- (pyridin-3-yl) naphthalen-4-yl) Benzo [d] [1,2,3] triazole

[Chemical Formula 1-6]

On the other hand, the compound of the formula (2) is an intermediate compound which is very useful for preparing the aromatic triazine derivative of the formula (1) as a novel substance. Hereinafter, preparation examples of the compound of formula (2) and preparation examples of other intermediates derived therefrom will be described.

Manufacturing example  A) Intermediate 2- (4- Bromophenol ) -5- Chloro Benzo [d] < RTI ID = 0.0 > [1,2,3] Triazole ( PM -1)

                                                         (PM-1)

500 ml of ethanol was placed in a 250 ml three-necked flask, and 150 g (670 mmol) of 4-bromophenylhydrazine hydrochloride and 70 g (854 mmol) of sodium triacetate were added thereto and stirred for 10 minutes. Then, 50 g ) And the mixture was refluxed with stirring for 20 hours.

After completion of the reaction, the reaction mixture was cooled to 5 캜, and the resulting slurry was filtered, washed with 2 L of water and 1.2 L of ethanol, and vacuum dried at 60 캜 to give 2- (4-bromophenol) (purity 99.2%, yield 73%) of [d] [1,2,3] triazole (PM-1).

[HPLC analysis conditions]

(1) Column: inersil ODS-SP, 4.6 ID x 250 mm (GL Science inc)

(2) Solvent: methanol: water = 85: 15

(3) Flow rate: 1.0 ml / min

(4) Detector (UV): 254 nm

Manufacturing example  B) Intermediate 5- Chloro -2- (9,10- Diphenylanthracene -3 days) Phenyl -2H- Benzo [d] [1,2,3] triazole ( PM -2)

(PM-2)

To a 250 ml three-necked flask were added 34 ml of purified water, 8.06 g (58 mmol) of potassium carbonate, 6 g (19.4 mmol) of the PM-1 compound, 8.73 g (18.4 mmol) of (9,10- diphenylanthracene- And the mixture is refluxed at 80 ° C for 30 minutes and cooled to 50 ° C. 0.76 g (0.58 mmol) of tetrakis (triphenylphosphine) palladium (0) [Pd (pph3) 4] was added and the mixture was heated to 80 ° C and refluxed for 2 hours.

The reaction solvent was concentrated in vacuo and 600 ml of toluene was added again to dissolve completely. The crystals were precipitated by gradually lowering the temperature, then cooled to 5 캜 and filtered to obtain 5-chloro-2- (9,10-diphenylanthracene- (Yield: 60%, purity: 99.3%) was obtained in the same manner as in Example 1,

^{1 H} NMR (400 MHz, CDCl ₃ ):? 8.0 (s, 1H), 7.9-7.8 (m, 4H), 7.7-7.6

7.5 to 7.4 (m, 10H), 7.3 to 7.2 (m, 10H)

Manufacturing example  C) Intermediate 2- (1- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborane Yl) naphthalen-4-yl) pyridine ( PM -3)

(PM-3)

C-1) Preparation of 4- (pyridin-3-yl) -1-aminonaphthalene

(40 mmol) of 3-pyridine boronic acid, 9.03 g (40 mmmol) of 1-amino-4-bromonaphthalene, and 16.86 g (122 mmol) of potassium carbonate were added to a 250 ml three-necked flask containing 36 ml of purified water and 54 ml of 1,4- And the mixture is heated to 80 DEG C using a water bath, refluxed for 30 minutes, and cooled to 50 DEG C. [

1.4 g (1.2 mmol) of tetrakis (triphenylphosphine) palladium (0) [Pd (pph3) 4] were added and stirred for 5 hours while refluxing. After confirming that the reaction was completed by thin layer chromatography, Concentrated to obtain 7.07 g (yield 78.5%, purity 93.2%) of 4- (pyridin-3-yl) -1-aminonaphthalene.

C-2) 3- (1- Iodo  Naphthalen-4-yl) pyridine

4.0 g (18 mmol) of 4- (pyridin-3-yl) -1-aminonaphthalene was added to a three-necked flask capable of blocking light, and 13 g of water was stirred together with 6.53 g of sulfuric acid at room temperature for 1 hour. g (22 mmol) were added thereto and stirred for 2 hours. The mixture was stirred at room temperature for 5 hours, extracted with toluene, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3.41 g (yield: 50%) of 3- (1-iodonaphthalen-4-yl) .

C-3) 2- (1- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborane Yl) naphthalen-4-yl) pyridine

4 g (18.4 mmol) of the above 3- (1-iodonaphthalen-4-yl) pyridine was placed in a 250 ml three-necked flask together with 13 g of water and 6.66 g of sulfuric acid. The mixture was stirred at room temperature for about 1 hour and then sodium nitrite (NaNO ₂ ) And 0.15 g (0.6 mmol) of Pin2B2 (bis (pinacolato) diboron) were added to the reaction mixture and reacted at 5 ° C for 5 hours. The reaction solution was extracted with toluene, dried and concentrated to give 2- (1- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) PM-3) (yield: 88%).

Manufacturing example  D) Intermediate 5- Chloro -2- (4- (9,10- Di (naphthalene-3-yl) anthracene Yl) Neal ) -2H-benzo [d] [1, 2,3] Triazole ( PM -4)

    (PM-4)

Purified water to 250ml reactor 34ml, K ₂ CO ₃ 6,0 g of the above PM-1 compound and 11.07 g of 9,10-di (naphthalene-3-yl) anthracen-2-yl-2-boronic acid and 60 ml of 1,4- After refluxing and stirring, the mixture was cooled to 50 캜, 0.67 g of Pd (pph ₃ ) ₄ was added, and the mixture was refluxed and stirred for 2 hours.

After the reaction mixture was concentrated and 500ml toluene added and dissolved in 80 ℃ SiO ₂ And the mixture is stirred, filtered and concentrated. To the concentrated residue, 600 ml of toluene was added and dissolved, followed by cooling. The solid thus precipitated was filtered and dried in vacuo at 60 ° C to give 5-chloro-2- (4- (9,10- ) Phenyl) -2H-benzo [d] [1,2,3] triazole (PM-4) (yield: 67%, purity: 99.6%).

^{1 H} NMR (400 MHz, CDCl ₃ ):? 8.0 (s, 1H), 7.9-7.8 (m, 4H), 7.7-7.6

7.5 to 7.4 (m, 10H), 7.3 to 7.2 (m, 10H)

[HPLC analysis conditions]

(1) Column lnertsil ODS-SP, 4.6 I.D X 250 mm (GL Sciences inc)

(2) Mobile phase Me-OH / THF = 95/5

(3) Flow rate 1.0 ml / min

(4) Column temp 40 ° C

(5) Detector (UV) 254 nm

Next, as a preferred embodiment of the present invention, the production method of the above-mentioned [1-1] to [1-6] will be explained.

Example  1) 3- (2- (4- (9,10- Di (naphthalene-3-yl) anthracene -3 days) Phenyl ) -2H- Ben article[ d] [1,2,3] triazole -6-yl) quinoline [Preparation of 1-1]

3.3 g of the PM-4 compound, 2.12 g of potassium phosphate, 1.03 g of quinoline-3-yl-3-boronic acid, 8.25 g of purified water and 82.5 ml of 1,4-dioxane were fed into a 250 ml reactor, Followed by reflux stirring. After completion of the reaction, the mixture was cooled to 50 ° C, 0.89 g of tricyclohexylphosphine 3 and 0.14 g of Pd ₂ (dba) ₃ were added and stirred, and then stirred at reflux overnight and cooled to room temperature.

The reaction solution was concentrated, 100 ml of toluene and 100 ml of SiO ₂ 20 g are added and stirred, and then the mixture is filtered, and the mixture is washed with 300 ml of toluene and 800 ml of acetic acid. The filtrate is concentrated and silica gel column is followed by recrystallization in a methanol solvent and vacuum drying at 40 ° C.

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ9.0 (s, 1H), 8.3 (m, 2H), 8.0 ~ 7.8 (m, 5H),

7.7-7.5 (m, 12H), 7.4-7.2 (m, 14H)

Example  2) 4- (2- (4- (9,10- Di (naphthalene-3-yl) anthracene -3 days) Phenyl ) - (2H- Ben article[ d] [1,2,3] triazole -6-yl) isoquinoline [Chemical Formula 1-2]

3.3 g of the PM-4 compound, 2.12 g of potassium phosphate, 1.03 g of isoquinolin-4-yl-4-boronic acid, 8.25 g of purified water and 82.5 ml of 1,4-dioxane were introduced into a 250 ml reactor, Lt; / RTI > When the reaction is completed, the mixture is cooled to 50 ° C, 0.89 g of tricyclohexylphosphine 3 and 0.14 g of Pd ₂ (dba) ₃ are added and stirred.

After stirring at reflux overnight, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 150 ml of SiO ₂ 20 g is added and stirred, and after filtration, it is washed with 300 ml of toluene and 800 ml of acetic acid. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography, recrystallization in a methanol solvent, and vacuum drying at 40 ° C.

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ 9.1 (s, 1H), 8.7 (s, 1H), 8.2 (s, 1H), 8.0 ~ 7.8 (m, 5H),

7.7-7.5 (m, 12H), 7.4-7.2 (m, 14H)

Example  3) 2- (4- (9,10- Di (naphthalene-3-yl) anthracene Yl) -5- (1-pyridin-3-yl) naphthalen-4-yl) Benzo [d] [1,2,3] triazole Preparation of [Formula 1-3]

Wherein a 250ml reactor PM-4 compound 3.3g, K ₃ PO ₄ 2.15 g of the above PM-3 compound, 8.25 g of purified water and 82.5 ml of 1.4-dioxane, and the reaction solution is refluxed for 30 minutes. When the reaction is completed, the mixture is cooled to 50 ° C, 0.89 g of tricyclohexylphosphine 3 and 0.14 g of Pd ₂ (dba) ₃ are added, and the mixture is stirred at reflux at night and cooled to room temperature. The reaction solution was concentrated, 100 ml of toluene and 100 ml of SiO ₂ 20 g is added and stirred. After filtration, the filtrate is washed with 300 ml of toluene and 800 ml of acetic acid, and the filtrate is concentrated and purified by silica gel column.

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ 8.8 (m, 1H), 8.5 (m, 1H), 8.2 (s, 1H), 8.0 ~ 7.9 (m, 5H),

7.7-7.5 (m, 14H), 7.4-7.2 (m, 16H)

Example  4) 3- (2- (4- (9,10- Diphenylanthracene -3 days) Phenyl ) -2H- Benzo [d] [1,2,3] tri Azol-6-yl) quinoline [Chemical Formula 1-4]

2.8 g of the PM-2 compound, 2.12 g of potassium phosphate, 1.03 g of quinolin-3-yl-3-boronic acid, 7 g of purified water and 70 g of 1.4-dioxane are introduced into a 250 ml reactor and stirred under reflux for 30 minutes. After cooling to 50 ° C, 0.89 g of tricyclohexylphosphine and 0.14 g of Pd ₂ (dba) ₃ were added, followed by reflux stirring at night. After cooling to room temperature, the mixture is concentrated, and 100 ml of toluene is added to dissolve it. Then, 20 g of SiO ₂ is added and stirred. Filter at room temperature, concentrate and column with silica gel.

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ 9.0 (s, 1H), 8.2 (m, 2H), 8.0 ~ 7.8 (m, 3H),

7.7-7.5 (m, 6H), 7.4-7.2 (m, 18H)

Example  5) 4- (2- (4- (9,10- Diphenylanthracene -3 days) Phenyl ) -2H- Benzo [d] [1,2,3] tri Azol-6-yl) isoquinoline [Formula 1-5]

Wherein a 250ml reactor PM-2 compound 2.8g, K ₃ PO ₄ 1.03 g of isoquinolin-4-yl-4-boronic acid, 7 g of purified water and 70 ml of 1,4-dioxane were added and stirred at reflux for 30 minutes. After cooling to 50 ° C, 0.89 g of tricyclohexylphosphine and 0.14 g of Pd ₂ (dba) ₃ were added and stirred, and then stirred at reflux overnight. After cooling at room temperature and concentration, 100 ml of toluene was added to dissolve and SiO ₂ 20 g is added and stirred. Filtered, concentrated to give a silica gel column, and vacuum dried (yield: 0.46 g, yield: 14.2%, purity: 91.0%)

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ 9.1 (s, 1H), 8.7 (s, 1H), 8.2 (m, 1H), 8.0 ~ 7.7 (m, 3H),

7.6-7.4 (m, 6H), 7.3-7.1 (m, 18H)

Example  6) 2- (4- (9,10- Diphenylanthracene Yl) -5- (1- (pyridin-3-yl) naphthalen-4-yl) Benzo [d] [1,2,3] triazole Preparation of [Formula 1-6]

2.8 g of the PM-2 compound, 2.12 g of the potassium phosphate, 2.0 g of the PM-3 compound, 7 g of purified water and 70 ml of 1,4-dioxane were charged into a 250 ml reactor and stirred under reflux for 30 minutes. The mixture was cooled to 50 ° C, and 0.89 g of trichlorohexylphosphine and 0.14 g of Pd ₂ (dba) ₃ were added thereto, followed by stirring under reflux for 16 hours. After cooling to room temperature and concentration, 100 ml of toluene is added to dissolve. SiO ₂ And the mixture is stirred, filtered and concentrated, and then subjected to silica gel column and vacuum drying.

_{^{1 H NMR (400MHZ, CDCl 3}} ): δ 8.9 (s, 1H), 8.5 (m, 1H), 8.2 (s, 1H), 8.1 ~ 7.8 (m, 3H),

7.7 ~ 7.5 (m, 8H), 7.4 ~ 7.0 (m, 20H)

[Device manufacturing example]

An anode is formed on a transparent substrate according to a conventional method and a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) EIL) and a cathode were successively laminated to prepare an organic electroluminescent device, and nine kinds of test devices (Devices A to I) were manufactured under the conditions shown in Tables 1 to 3 below. In this case, the thickness of each layer was 150 nm for the anode, 25 nm for the hole injecting layer, 35 nm for the hole transporting layer, 25 nm for the light emitting layer, 35 nm for the electron transporting layer, 0.5 nm for the electron injecting layer and 150 nm for the cathode. In a resistance heating thermal deposition method.

Among the above-mentioned test elements, the elements A to C used Alq3 and Balq, which are conventional electron transporting layer materials, as they are as the material of the electron transport layer (ETL) A material in which the compound of the formulas 1-1 to 1-6 and the Alq3 compound are mixed at a weight ratio of 1: 1 is used.

division Element A Device B Device C Emitting color Green light Green light Green light Negative pole Al Al Al Electron injection layer LiF LiF LiF Electron transport layer Alq3 Balq Balq: Alq3 = 7: 3 Light emitting layer Alq3 + Co6 (1%) Alq3 + Co6 (1%) Alq3 + C545T (1%) Hole transport layer NPB NPB NPB Hole injection layer CuPc CuPc CuPc Positive pole ITO ITO ITO

division Device D Device E Device F Emitting color Green light Green light Green light Negative pole Al Al Al Electron injection layer LiF LiF LiF Electron transport layer Alq3: P1 = 1: 1 Alq3: P2 = 1: 1 Alq3: P3 = 1: 1 Light emitting layer Alq3 + C545T (1%) Alq3 + C545T (2%) Alq3 + C545T (3%) Hole transport layer NPB NPB NPB Hole injection layer CuPc CuPc CuPc Positive pole ITO ITO ITO

division Element G Device H Device I Emitting color Green light Green light Green light Negative pole Al Al Al Electron injection layer LiF LiF LiF Electron transport layer Alq3: P4 = 1: 1 Alq3: P5 = 1: 1 Alq3: P6 = 1: 1 Light emitting layer Alq3 + C545T (4%) Alq3 + C545T (5%) Alq3 + C545T (6%) Hole transport layer NPB NPB NPB Hole injection layer CuPc CuPc CuPc Positive pole ITO ITO ITO

Meanings of abbreviations used in Tables 1 to 3 are as shown in Table 4 below.

Weak meaning CuPc  copper phthalocyanine NPB  4,4'-bis [(1-naphthyl) -N-phenylamino] biphenyl Alq3  tris- (8-hydroxyquinolinato) -aluminium Balq  aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate C545T 2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H, 11H-10- (2-benzothiazolyl)
quinolizino [9,9a, 1 H] coumarin CBP  2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Ir (ppy) 3  tris [2-phenylpyridinato-C 2, N] iridium (III) ITO  인ium 티온 산화물

[Evaluation of device characteristics]

Current, luminance, luminous efficiency (lm / W, cd / A,%) of the test elements A to I were measured using an IVL (Current-Voltage-Luminance) At this time, the current density was measured at 50 mA / cm < 2 >, and the specifications of the IVL measuring instrument are as follows.

<Specifications of IVL Meter>

1) Model name: SMU (Keithley-2400): Keithley

2) Power output: 22W

3) Current Capability: Min ± 10 pA, Max ± 1.05 A

4) Voltage Capability: Min ± 10μV, Max ± 21 ± 210V

5) Ohms Range: 0.2Ω ~ 200MΩ

6) Basic Accuracy: I (0.035%), V (0.015%), Ω (0.06%)

1 and 2 are graphs showing changes in current density (mA / cm 2) along the applied voltage (V) (X axis) with respect to the devices A to I. 1, the device B using Balq as the material of the electron transport layer (ETL) is about 1 volt away from the device A using Alq3 and the device C using the mixture material of Balq + Alq3 is about It can be seen that the voltage of about 2 volts drops.

In the case of the devices D to I in which the aromatic triazine compound according to the present invention is used together, as shown in FIG. 2, the voltage performance is improved as a whole compared to the devices A to C, 6 showed the best performance.

3 and 4 are graphs showing changes in the light emission luminance (nit, cd / cm2; Y axis) according to the current density (mA / cm; X axis) of the devices A to I. 3, it can be seen that the device C has a higher voltage efficiency but a higher luminous efficiency than the other devices. It is presumed that the efficiency of the device is increased by mixing Balq having a hole blocking property.

In the case of using the aromatic triazine compound according to the present invention together, as shown in FIG. 4, the same results are obtained as compared with the devices A to C, Luminescent efficiency was observed.

Claims (5)

delete delete delete 1) Reaction of 2- (4-bromophenol) -5-chloro-2H- benzo [d] [1,2,3] triazole with (9,10- diphenylanthracene- Dichloro-2- (9,10-diphenylanthracen-3-yl) phenyl) -2H-benzo [d] [1,2,3] triazole;
2) Synthesis of 2- (1- (4, 4-dioxolan-2-yl) (9,10-diphenylanthracene-3-yl) thiophene-2-yl) -5- (1- (pyridin-3-yl) naphthalen-4-yl) -2H-benzo [d] [1,2,3] triazole;
Wherein the aromatic triazine derivative for organic electroluminescent device is a compound represented by formula
5. The method of claim 4,
In the above step 2), 1,4-dioxane is used as a reaction solvent, and trichlorohexylphosphine and Pd ₂ (dba) ₃ are used as catalysts to prepare an aromatic triazine derivative for organic electroluminescence device Way.

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