KR101548694B1 - New pyrimidine derivative and organic light-emitting devices including the same - Google Patents

Abstract

The present invention relates to a novel pyrimidine derivative and an organic light emitting device including the same in a light emitting layer. The organic light emitting device according to the present invention not only excels in luminescence characteristics but also enhances a driving voltage, Has the advantage of being improved.

Description

TECHNICAL FIELD The present invention relates to a novel pyrimidine derivative and an organic light emitting device including the pyrimidine derivative and organic light-

The present invention relates to a novel pyrimidine derivative and an organic light emitting device including the pyrimidine derivative. More particularly, the present invention relates to a novel pyrimidine derivative as a light emitting compound and an organic light emitting device including the pyrimidine derivative in the light emitting layer.

An organic light emitting device is a device that injects electric charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole. It is possible to form a device on a flexible transparent substrate such as a plastic substrate and to operate at a lower voltage (10 V or less) than a plasma display panel or an inorganic EL display, It is relatively small and has an advantage of excellent color.

The structure of a general organic electroluminescent device includes a substrate, a cathode, a hole injecting layer for receiving holes from the anode, a hole transporting layer for transporting holes, a light emitting layer for emitting light by combining holes and electrons, An electron transport layer, and a cathode. In some cases, a light emitting layer may be formed by doping a small amount of a fluorescent or phosphorescent dye to an electron transporting layer or a hole transporting layer without a separate light emitting layer. In the case of using a polymer, a hole transporting layer, a light emitting layer, and an electron transporting layer Can be performed simultaneously. The organic thin film layers between the two electrodes are formed by a vacuum deposition method, a spin coating method, an ink jet printing method, a roll coating method, or the like, and a separate electron injection layer may be inserted to efficiently inject electrons from the cathode.

In addition, since the interface between the electrode and the organic material is stabilized, or the organic material has a large difference in the transport speed of holes and electrons, it is possible to effectively transfer holes and electrons to the light emitting layer by using a suitable hole transporting layer and an electron transporting layer. The organic light emitting device is fabricated into a multilayer thin film structure in order to balance the densities of holes and electrons and to increase the luminous efficiency.

On the other hand, the most important factor for determining the luminous efficiency in an organic light emitting device is a light emitting material. As a light emitting material, a fluorescent material is most widely used, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically, and various studies have been made.

However, most of the materials developed in the past have advantages in terms of light emission characteristics, but they have disadvantages such as low glass transition temperature and poor thermal stability, which causes materials to change when subjected to a high temperature deposition process under vacuum.

Therefore, research on the development of excellent luminescent materials as in Korean Patent Laid-Open Publication No. 2012-0117501 is continuing, but development of luminescent materials having high luminescent efficiency and high lifetime characteristics is required.

Korean Patent Laid-Open Publication No. 2012-0117501

The present invention provides novel pyrimidine derivatives.

The present invention also provides an organic light emitting device comprising a novel pyrimidine derivative as a light emitting layer.

The present invention provides an organic light emitting device including a novel pyrimidine derivative having high light emitting efficiency and high lifetime characteristics in a light emitting layer.

The novel pyrimidine derivative contained in the light emitting layer of the organic light emitting device of the present invention is represented by the following general formula (1).

[Chemical Formula 1]

[In the above formula (1)

R ₁ to R ₆ are independently of each other hydrogen, (C 1 -C 30) alkyl, (C 3 -C 30) cycloalkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

R ₇ and R ₉ are independently from each other hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; R ₈ and R ₉ are (C3-C30) -C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the carbon atom of the formed alicyclic ring and the monocyclic or polycyclic aromatic ring is selected from nitrogen, oxygen and sulfur Which may be substituted with one or more heteroatoms;

L is (C6-C30) arylene or (C3-C30) heteroarylene;

n is an integer from 0 to 3;

The alkyl, cycloalkyl, aryl and heteroaryl of R ₁ to R ₆ or the alkyl, aryl, heteroaryl, alkylene and alkenylene of R ₇ to R ₉ are independently selected from the group consisting of (C 1 -C 30) alkyl, halo (C 1 -C 30) (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl (C3-C30) aryl (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, mono- or di (C6-C30) arylsilyl, nitro, and hydroxy.

The organic light emitting device comprising the novel pyrimidine derivative represented by Formula 1 of the present invention in the light emitting layer is a compound in which pyrimidine and phenyl group are connected by one or more arylene or heteroarylene, The density is high and the luminous efficiency is high.

In the light emitting device of the present invention,

R ₁ to R ₆ are, independently of each other, (C ₁ -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

R ₇ and R ₉ are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; R ₈ and R ₉ are ) Alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the carbon atom of the formed alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with at least one group selected from nitrogen, oxygen and sulfur Lt; / RTI > may be substituted with a heteroatom;

L is (C6-C30) arylene;

n is an integer from 1 to 3;

The alkyl, aryl and heteroaryl of R ₁ to R ₆ or the alkyl, aryl, heteroaryl, alkylene and alkenylene of R ₇ to R ₉ are independently selected from the group consisting of (C 1 -C 30) alkyl, halo (C 1 -C 30) (C3-C30) heteroaryl substituted with (C1-C30) alkyl, cyano, (C1-C30) alkoxy, ≪ / RTI >

Preferably, Formula 1 according to an embodiment of the light emitting device of the present invention may be represented by Formula 2 below.

(2)

[In the formula (2)

R ₁ to R ₆ are, independently of each other, (C ₁ -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

R < ₇ > is (C6-C30) aryl;

L is (C6-C30) arylene;

n is an integer of 1 to 2;

Aryl in the above R ₁ to R ₆ alkyl, aryl and heteroaryl, or R ₇ a is (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C1-C30) alkoxy, (C6-C30 (C3-C30) heteroaryl, (C3-C30) heteroaryl, (C3-C30) heteroaryl, nitro, and hydroxy.

The organic light emitting device comprising the light emitting layer of Formula 2 according to an embodiment of the present invention has a high luminous efficiency due to a ring fused with pyrimidine naphthalene, that is, benzo [ h ] quinazoline.

In Formula (2) according to an embodiment of the present invention, R ₁ to R ₆ are independently (C ₁ -C 30) alkyl or may be selected from the following structures.

(C6-C30) aryl, (C3-C30) heteroaryl or (C1-C30) alkyl (C6-C30) heteroaryl, wherein R ', R "and R' C30) aryl.]

Preferably, in Formula 2 of the organic light emitting device having Formula 2 of the present invention, one of R ₁ to R ₆ may have the formula.

 Preferably, Formula 1 according to an embodiment of the present invention may be represented by Formula 3 in terms of luminous efficiency.

(3)

[Formula 3]

R < ₇ > is (C6-C30) aryl;

L is (C6-C30) arylene;

n is an integer of 1 to 2;

R ₁₁ or R ₁₂ independently from each other are hydrogen, (C 1 -C 30) alkyl or (C 6 -C 30) aryl;

and o is an integer of 1 to 4.]

More specifically, the pyrimidine derivative represented by Formula 1 according to an embodiment of the present invention may be selected from the following compounds, but is not limited thereto.

An organic light emitting device according to an embodiment of the present invention includes a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode. The organic compound layer may include the light-emitting compound and the light-emitting layer containing the pyrimidine derivative represented by Formula 1 of the present invention .

The present invention also provides a pyrimidine derivative represented by the above formula (1).

[Chemical Formula 1]

[In the above formula (1)

R ₁ to R ₆ are independently of each other hydrogen, (C 1 -C 30) alkyl, (C 3 -C 30) cycloalkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

R ₇ and R ₉ are independently from each other hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; R ₈ and R ₉ are (C3-C30) -C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the carbon atom of the formed alicyclic ring and the monocyclic or polycyclic aromatic ring is selected from nitrogen, oxygen and sulfur Which may be substituted with one or more heteroatoms;

L is (C6-C30) arylene or (C3-C30) heteroarylene;

n is an integer from 0 to 3;

The alkyl, cycloalkyl, aryl and heteroaryl of R ₁ to R ₆ or the alkyl, aryl, heteroaryl, alkylene and alkenylene of R ₇ to R ₉ are independently selected from the group consisting of (C 1 -C 30) alkyl, halo (C 1 -C 30) (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl (C3-C30) aryl (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, mono- or di (C6-C30) arylsilyl, nitro, and hydroxy.

The formula (1) according to an embodiment of the present invention may be represented by the following formula (2).

(2)

[In the formula (2)

R ₁ to R ₆ are, independently of each other, (C ₁ -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

R < ₇ > is (C6-C30) aryl;

L is (C6-C30) arylene;

n is an integer of 1 to 2;

Aryl in the above R ₁ to R ₆ alkyl, aryl and heteroaryl, or R ₇ a is (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C1-C30) alkoxy, (C6-C30 (C3-C30) heteroaryl, (C3-C30) heteroaryl, (C3-C30) heteroaryl, nitro, and hydroxy.

The pyrimidine derivatives of the present invention are illustrated by the following reaction schemes, but the present invention is not limited thereto and may be prepared through known organic reactions.

[Reaction Scheme]

[In the above reaction formula

R ₁ to R ₉ , L and n are the same as defined in the above formula 1.]

The organic light-emitting device including the pyrimidine derivative of the present invention in the light-emitting layer has high luminance, high luminous efficiency, and excellent lifetime characteristics of the device.

FIG. 1 is a graph showing the efficiency (cd / A) vs. luminance (cd / m 2) of the organic light emitting device manufactured in Examples 5 to 8 and Comparative Example 1.

Hereinafter, the present invention will be better understood by reference to the following examples, and the following examples are for illustrative purposes only and are not intended to limit the scope of protection of the present invention.

[ Example  1] Preparation of compound 1

compound  1-a Manufacturing

30 g (205 mmol) of 1-tetralone and 39.8 g (215 mmol) of 4-bromobenzaldehyde were placed in a 500 mL-3-necked round bottom flask and dissolved in 200 mL of methanol. Then, 10.2 g ) Was slowly added and stirred at room temperature for 12 hours. The precipitated solid was separated by filtration under reduced pressure and washed with methanol to obtain 37.4 g (yield: 58%) of a pale yellow solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 2.97 (t, 2H), 3.10 (t, 2H), 7.28 (s, 1H), 7.33 (d, 2H), 7.41 (t, 1H), 7.52 (t , 7.56 (d, 2H), 7.79 (s, IH), 8.15 (d, IH)

compound  1-b Manufacturing

5 g (15.9 mmol) of compound 1-a, 2.7 g (17.5 mmol) of benzamidine hydrochloride and 0.95 g (23.9 mmol) of sodium hydroxide were placed in a 250 mL three-neck round bottom flask and dissolved in 50 mL of ethanol. Lt; / RTI > After cooling, the precipitated solid was filtered off under reduced pressure, and the residue was separated by silica gel column (hexane: methylene chloride = 1: 1) to obtain 4.02 g of a white solid compound (yield: 60%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 2.93 (t, 2H), 3.08 (t, 2H), 7.28 (s, 1H), 7.45-7.54 (m, 5H), 7.62-7.70 (m, 4H) , 8.60-8.66 (m, 3H)

compound  1-c Manufacturing

5 g (12.1 mmol) of the compound 1-b and 2.8 g (12.3 mmol) of 2,3-dichloro-5,6-dicyanobenzoquinone were placed in a 250 mL-3-necked round bottom flask, mL and then refluxed at 120 ° C for 12 hours. After cooling, the reaction mixture was extracted with water and methylene chloride, and recrystallized from methanol to obtain 4.32 g (yield: 86%) of a white solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.52-7.58 (m, 3H), 7.74-7.80 (m, 7H), 7.89-7.93 (m, 2H), 8.81 (d, 2H), 9.54 (m, 1H)

compound  1-d Manufacturing

To a 250 mL three-neck round bottom flask was added 15 g (36.5 mmol) of compound 1-c, 3.2 g (38.3 mmol) of 2-methyl-3-butyn- 0.48 g (1.8 mmol) of triphenylphosphine, 0.35 g (1.8 mmol) of copper iodide, and 75 ml of triethylamine were added to the solution, and the mixture was refluxed for 4 hours and stirred. After filtration under reduced pressure, the residue was washed with water to obtain 14.2 g (yield: 94%) of a solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.32-7.36 (m, 3H), 7.42 (t, 2H), 7.58 (d, 4H), 7.64-7.69 (m, 4H), 7.84 (m, 1H) , 7.87 (d, 1 H), 1.62 (s, 6 H), 1.29 (s, 1 H)

compound  1-e Manufacturing

14 g (33.8 mmol) of the compound 1-d, 0.5 g (10.1 mmol) of potassium hydroxide and 70 mL of toluene are placed in a 250 mL-3-necked round bottom flask and refluxed and stirred for 3 hours. After completion of the reaction, water is added, and the mixture is extracted with methylene chloride. After removing moisture with magnesium sulfate, the mixture was concentrated under reduced pressure, and the resulting solid was washed with hexane. 9.5 g (yield: 79%) of yellow solid compound was obtained.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.32-7.36 (m, 3H), 7.41 (t, 2H), 7.59 (s, 4H), 7.64-7.69 (m, 4H), 7.84 (m, 1H) , 7.89 (d, 1 H), 3.13 (s, 1 H)

compound  1-f Manufacturing

200 mL of tetrahydrofuran (THF), 20 g (54.2 mmol) of iodophenylcarbazole, 23 g (65 mmol) of the compound 1-e and 21.9 g (216.7 mmol) of triethylamine were added to a 500 mL- 0.76 g (1.1 mmol) of dichlorobistriphenylphosphine palladium (II) and 0.21 g (1.1 mmol) of copper iodide were added thereto, and the mixture was refluxed for 12 hours and stirred. After completion of the reaction, the mixture was filtered under reduced pressure, and the resulting solid was recrystallized from hexane to obtain 10.1 g (yield: 40%) of a white solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.15-7.18 (t, 1H), 7.24-7.30 (m, 2H), 7.38-7.41 (t, 1H), 7.45-7.50 (m, 7H), 7.62- 2H), 7.95-7.97 (m, 1H), 8.09 (d, 2H)

compound  1-g Manufacturing

10 g (48 mmol) of 1,3-diphenyl-2-propanone and 10 g (48 mmol) of benzyl were dissolved in 150 ml of methanol, and 4 g (72 mmol) of potassium hydroxide was added to a 250 ml- Slowly. After refluxing for 5 hours and filtration under reduced pressure, 10.2 g (yield: 55%) of a black solid compound was obtained.

^{1 H NMR (DMSO) δ [} ppm]: 7.34 (t, 1H), 7.43 (m, 7H), 7.58 (d, 1H), 7.83 (d, 1H)

compound One  Manufacturing

Add 10 g (26 mmol) of the compound 1-g and 15.5 g (26 mmol) of the compound 1-f to a 500 mL-3-necked round bottom flask and dissolve in 200 ml of diphenyl ether. After refluxing for 4 hours, 140 ml of hexane is added. The resulting brown solid was filtered off under reduced pressure, and the residue was separated by silica gel column (Hexane: EA = 3: 1) to obtain 7.3 g (yield: 70%) of a white solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 6.81 (t, 1H), 6.92 (t, 1H), 7.04 (t, 2H), 7.12 (d, 1H), 7.22 (d, 1H), 7.28-7.41 (m, 4H), 7.62-7.67 (m, 9H), 7.76 (d, 2H), 7.86 (d, 2H), 7.92 ), 8.16 (d, IH), 8.22 (d, 2H), 8.45

MALDI-TOF MS: m / z 399.28, cal. 399.94

[Example 2] Preparation of Compound 2

compound  2-a Manufacturing

35 g (239 mmol) of 3-bromobenzaldehyde and 46.6 g (252 mmol) of 1-tetralone were added to a 1000 mL-3-necked round bottom flask and dissolved in 200 mL of ethanol. Then, 11.9 g (299 mmol) And the mixture was stirred at room temperature for 12 hours. The precipitated solid was separated by filtration under reduced pressure and washed with methanol to obtain 64.2 g (yield: 85%) of a pale yellow solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 2.98 (t, 2H), 3.12 (t, 2H), 7.27-7.41 (m, 4H), 7.49-7.54 (m, 2H), 7.59 (s, 1H) , 7.79 (s, 1 H), 8.14 (d, 1 H)

compound  2-b Manufacturing

60 g (190 mmol) of compound 2-a, 33 g (210 mmol) of benzamidine hydrochloride and 11.4 g (290 mmol) of sodium hydroxide were added to a 1000 mL-3-necked round bottom flask and dissolved in 600 mL of ethanol. Lt; / RTI > After cooling, the precipitated solid was filtered off under reduced pressure and then separated by silica gel column (hexane: methylene chloride = 1: 1) to obtain 54.4 g of a pale yellow solid compound (yield: 68%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 2.87 (t, 2H), 3.02 (t, 2H), 7.24 (s, 1H), 7.34-7.61 (m, 8H), 7.87 (s, 1H), 8.56 -8.63 (m, 3 H)

compound  2-c Manufacturing

62.7 g (151 mmol) of the compound 2-b and 34 g (151 mmol) of 2,3-dichloro-5,6-dicyanobenzoquinone were placed in a 1000 mL three-necked round bottom flask, and 600 mL And then refluxed at 120 ° C for 12 hours. After cooling, the reaction mixture was extracted with water and methylene chloride, and then separated by a silica gel column (hexane: methylene chloride = 1: 1) to obtain 22.42 g of a pale yellow solid compound (yield: 36%).

¹ H NMR (CDCl ₃ )? [Ppm]: 7.47-7.59 (m, 4H), 7.72-8.07 (m, 8H), 8.82 (d, 2H), 9.54

compound  2-d Manufacturing

To a 250 mL three-neck round bottom flask was added 20 g (48.6 mmol) of compound 2-c, 4.3 g (51.1 mmol) of 2-methyl-3-butyn- (0.5 mmol), triphenylphosphine (0.6 g, 2.4 mmol), copper iodide (0.4 g, 2.4 mmol) and triethylamine (100 ml) were added and the mixture was refluxed for 4 hours and stirred. After filtration under reduced pressure, the filtrate was washed with water to obtain 18.1 g of a solid compound (yield: 90%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.32-7.43 (m, 6H), 7.53-7.55 (d, 1H), 7.64-7.72 (m, 5H), 7.85 (m, 1H), 7.94 (d, 1H), 1.54 (s, 6H), 1.39 (s, 1 H)

compound  2-e Manufacturing

18 g (43.4 mmol) of the compound 2-d, 0.7 g (13 mmol) of potassium hydroxide and 90 mL of toluene are placed in a 250 mL three-necked round bottom flask and refluxed and stirred for 3 hours. After completion of the reaction, water is added, and the mixture is extracted with methylene chloride. After removing moisture with magnesium sulfate, the mixture was concentrated under reduced pressure, and the resulting solid was washed with hexane. 12.7 g (yield: 82%) of a pale yellow solid compound was obtained.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.32-7.43 (m, 6H), 7.52 (d, 1H), 7.58 (d, 1H), 7.65-7.69 (m, 4H), 7.84 (m, 2H) , 7.87 (d, 1 H), 3.11 (s, 1 H)

compound  2-f Manufacturing

(THF), 12.6 g (34.1 mmol) of iodophenylcarbazole, 14.6 g (41 mmol) of the compound 2-e and 13.8 g (136.5 mmol) of triethylamine were added to a 500 mL three- 0.48 g (0.7 mmol) of dichlorobistriphenylphosphine palladium (II) and 0.1 g (0.7 mmol) of copper iodide were added thereto, and the mixture was refluxed for 12 hours and stirred. After completion of the reaction, the mixture was filtered under reduced pressure, and the resulting solid was recrystallized from hexane to obtain 7.1 g (yield: 35%) of a white solid compound.

¹ H NMR (CDCl ₃ )? [Ppm]: 7.06-7.09 (t, 1H), 7.21-7.28 (m, 2H), 7.42-7.65 (m, 15H), 7.76 4H), 7.97-8.01 (m, 2H), 8.06 (d, 1H), 8.37 (s, 2H)

compound 2  Manufacturing

Add 7 g (18.2 mmol) of the compound 1-g and 10.8 g (18.2 mmol) of the compound 2-f into a 250 mL three-necked round bottom flask and dissolve in 150 mL of diphenyl ether. After refluxing for 4 hours, 200 ml of hexane is added. The resulting brown solid was filtered off under reduced pressure, and then separated by silica gel column (Hexane: EA = 3: 1) to obtain 5.1 g of a white solid compound (yield: 70%).

¹ H NMR (CDCl ₃ )? [Ppm]: 6.81 (t, IH), 6.88 (t, IH), 7.17 (d, IH), 7.29 (d, IH), 7.37-7.45 2H), 8.49 (d, 1H), 8.16 (m, 2H), 8.49 (m, 2H) , 1H)

MALDI-TOF MS: m / z 399.28, cal. 399.75

[Example 3] Preparation of Compound 3

compound  3-a Manufacturing

10 g (24.3 mmol) of the compound 1-c is placed in a 500 mL three-necked round bottom flask, 6.48 g (25.5 mmol) of bis (pinacolato) diboron are added, and 200 mL of 1,4-dioxane is added. Dichloropalladium (II) and 0.36 g (0.49 mmol) of a chloromethane complex were added, and 4.8 g (48.6 mmol) of potassium acetate was added thereto, followed by heating and stirring with refluxing . After about 12 hours of reaction, the reaction is cooled to room temperature. Extraction is carried out with a saturated aqueous solution of sodium chloride and ethyl acetate. Dried with magnesium sulfate, treated with activated charcoal, filtered through celite, and concentrated under reduced pressure. The solid obtained after concentration was suspended in hexane, followed by filtration and washing with hexane to obtain 9.8 g (Yield: 87.9%) of yellow solid compound.

¹ H NMR (CDCl ₃ )? [Ppm]: 1.40 (s, 12H), 7.12 (s, 1H), 7.55 (m, 7H), 7.68

compound  3-b Manufacturing

17.7 g (38.7 mmol) of 1,4-dibromo-2,3,5,6-tetraphenylbenzene (19 g, 35.2 mmol) was added to a 1000 mL three-necked round bottom flask and 400 mL Lt; / RTI > 0.4 g (0.3 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, 200 ml of a 1M potassium carbonate aqueous solution was added, and the mixture was heated to reflux. After about 18 hours of reaction, the reaction is cooled to room temperature. The mixture is extracted with saturated aqueous sodium chloride solution and dichloromethane, dried over magnesium sulfate and concentrated under reduced pressure. The solid was separated by silica gel column (Hexane: EA = 10: 1), concentrated and washed with hexane to obtain 12.5 g of a yellow solid compound (yield: 45%).

¹ H NMR (CDCl ₃ )? [Ppm]: 7.33-7.48 (m, 17H), 7.61-7.65 (t, 8H), 7.70 (d, 2H), 7.76-7.82 m, 2H)

compound  3-c Manufacturing

30 g (81.3 mmol) of iodophenylcarbazole was added to a 1000 mL three-necked round bottom flask, 22.7 g (89 mmol) of bis (pinacolato) diboron were added, and 450 mL of 1,4-dioxane was added . 1.3 g (1.6 mmol) of 1,1'-bis [(diphenylphosphino) ferrocene] dichloropalladium (II) and chloromethane complex were added, and potassium nitrate (15.9 g, 162.5 mmol) was added and the mixture was heated and stirred under reflux . After about 12 hours of reaction, the reaction is cooled to room temperature. Extraction is carried out with a saturated aqueous solution of sodium chloride and ethyl acetate. After drying with magnesium sulfate, the mixture is concentrated under reduced pressure. The concentrate was separated by silica gel column (Hexane: EA = 10: 1) and the obtained solid was recrystallized from methanol to obtain 19.5 g of a white solid compound (yield: 65%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 1.40 (s, 12H), 7.25-7.33 (m, 2H), 7.51-7.58 (m, 7H), 7.94-7.98 (m, 2H), 8.55 (t, 1H)

compound  3 Manufacturing

Add 12 g (15.2 mmol) of the compound 3-b and 6.2 g (16.7 mmol) of the compound 3-c into a 1000 mL three-necked round bottom flask, and add 240 mL of tetrahydrofuran (THF). 0.2 g (0.2 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, 120 ml of a 1M potassium carbonate aqueous solution was added, and the mixture was heated to reflux. After about 18 hours of reaction, the reaction is cooled to room temperature. After cooling, the precipitated solid is filtered under reduced pressure, dissolved in toluene, filtered through celite, and concentrated under reduced pressure. The solid obtained after concentration was recrystallized from methanol to obtain 8.7 g (yield: 60%) of a white solid compound.

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 6.78 (t, 1H), 6.91 (t, 1H), 7.05 (t, 2H), 7.21 (t, 2H), 7.32-7.56 (m, 24H), 7.66 1H), 8.52 (d, IH), 8.62 (d, IH)

MALDI-TOF MS: m / z 954.16, cal. 954.43

[Example 4] Preparation of Compound 14

compound  14-a Manufacturing

160 mL of tetrahydrofuran (THF), 16 g (60.8 mmol) of 2-bromodiforborniophene, 26 g (73 mmol) of 2-e and 24.6 g (243.2 mmol) of triethylamine were added to a 500 mL- 0.8 g (1.2 mmol) of dichlorobistriphenylphosphine palladium (II) and 0.2 g (1.2 mmol) of copper iodide were added to the solution, and the mixture was refluxed for 12 hours and stirred. After completion of the reaction, the mixture was filtered under reduced pressure, and the obtained solid was recrystallized from hexane to obtain 14.7 g of a white solid compound (yield: 45%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 7.26-7.32 (m, 2H), 7.43-7.56 (m, 7H), 7.61 (d, 1H), 7.72 (d, 1H), 7.76-7.85 (m, 1H), 8.15 (s, 1 H), 8.05 (d, IH), 7.92-7.94

compound 14  Manufacturing

Add 14 g (36.4 mmol) of the compound 1-g and 19.6 g (36.4 mmol) of the compound 14-a to a 500 mL-3-necked round bottom flask and dissolve in 250 mL of diphenyl ether. After refluxing for 4 hours, 200 ml of hexane is added. The formed brown solid was filtered off under reduced pressure, and the residue was separated by silica gel column (Hexane: EA = 3: 1) to obtain 21.1 g of a white solid compound (yield: 65%).

_{^{1 H NMR (CDCl 3) δ}} [ppm]: 6.84 (t, 1H), 6.94-6.98 (m, 3H), 7.24-7.27 (m, 2H), 7.37-7.72 (m, 29H), 7.87-7.88 ( 1H), 8.91 (d, IH), 8.14 (s, IH)

MALDI-TOF MS: m / z 895.12, cal. 895.75

[Example 5] Fabrication of organic light emitting device using Compound 1 according to the present invention

A transparent anode of indium tin oxide (ITO) having a film thickness of 750 ANGSTROM was formed on a glass substrate having a size of 25 mm x 75 mm x 1.1 mm. The glass substrate was placed in a vacuum deposition apparatus and reduced in pressure to about 10 ^-7 torr. The following compound HIL was vapor-deposited to a thickness of 400 ANGSTROM to form a hole injection layer. Subsequently, the following compound HTL was vapor-deposited to a thickness of 300 ANGSTROM to form a hole transport layer. Compound 1 according to the present invention was deposited as a host material to a thickness of 300 Å at a weight ratio of 7% by using Ir (ppy) 3 as a dopant, and the following compound Alq ₃ [tris (8-hydroxyquinoline ) Aluminum (III)] was deposited to a thickness of 300 ANGSTROM to form a light emitting layer. The following compound BCP of the present invention was deposited on the light emitting layer to form an electron transport layer having a film thickness of 300 ANGSTROM. Liq (lithium quinolate) was then deposited thereon to form an electron injection layer. Metal aluminum was deposited on the Liq film to form a metal cathode, thereby fabricating an organic light emitting device.

A voltage of 0 to 15 V was applied to the thus fabricated organic light emitting device, and a luminescence test was performed. Table 1 shows electroluminescence characteristics and basic physical property measurement results.

[Example 6] Fabrication of organic light emitting device using compound 2 according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 5 except that Compound 2 was used instead of Compound 1 as a light emitting material in Example 5. The electroluminescence characteristics and the basic physical property measurement results are shown in Table 1 below .

[Example 7] Fabrication of organic light emitting device using Compound 3 according to the present invention

An organic light emitting device was fabricated under the same conditions as those of Example 5 except that Compound 3 was used instead of Compound 1 as a light emitting material in Example 5. The electroluminescence characteristics and basic physical property measurement results are shown in Table 1 below .

[Example 8] Fabrication of organic light emitting device using compound 4 according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 5, except that Compound 4 was used instead of Compound 1 as a light emitting material in Example 5, and the electroluminescence characteristics and basic physical property measurement results are shown in Table 1 below .

[Comparative Example 1] Fabrication of organic light emitting device using compound CBP

An organic light emitting device was fabricated under the same conditions as in Example 5 except that the compound CBP was used in place of the compound 1 as the light emitting material in Example 5. The electroluminescence characteristics and the basic physical property measurement results are shown in Table 1 below .

No. Voltage (V) Current density
(mA / cm ² ) efficiency
(cd / A) The color coordinates (x, y) Luminance
(cd / m 2) Example 1 7.00 5.39 18.96 0.30, 0.61 1022 Example 2 7.40 2.93 36.67 0.29, 0.62 1078 Example 3 13.50 3.38 30.93 0.31, 0.61 1046 Example 4 7.10 2.71 39.43 0.28, 0.62 1072 Comparative Example 1 7.40 5.25 20.11 0.29, 0.62 1033

 As shown in Table 1, it was confirmed that the organic light emitting device including the pyrimidine derivative of the present invention as a light emitting layer exhibited superior characteristics to the conventional materials. In other words, it can be seen that not only has excellent luminance and high efficiency, but also high lifetime characteristics.

Claims (9)

An organic light emitting device comprising a pyrimidine derivative represented by the following formula (2) as a light emitting layer.
(2)

[In the formula (2)
R ₁ to R _3, R ₅ and R ₆ independently of one another are (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;
R < ₇ > is (C6-C30) aryl;
L is (C6-C30) arylene;
n is an integer of 1 to 2;
Wherein R ₁ to R _3, the aryl of R ₅ and R _6, aryl and heteroaryl, and R ₇ of the (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C1-C30) (C3-C30) heteroaryl, (C3-C30) heteroaryl, (C3-C30) heteroaryl, nitro and hydroxy Can be.] delete delete The method according to claim 1,
Wherein R ₁ to R _3, R ₅ and R ₆ are each independently (C 1 -C 30) alkyl or is selected from the following structures.

(C6-C30) aryl, (C3-C30) heteroaryl or (C1-C30) alkyl (C6-C30) heteroaryl, wherein R ', R "and R' C30) aryl.] The method according to claim 1,
(2) is represented by the following formula (3).
(3)

[Formula 3]
R < ₇ > is (C6-C30) aryl;
L is (C6-C30) arylene;
n is an integer of 1 to 2;
R ₁₁ or R ₁₂ independently from each other are hydrogen, (C 1 -C 30) alkyl or (C 6 -C 30) aryl;
and o is an integer of 1 to 4.] The method according to claim 1,
Wherein the organic compound is selected from the following compounds.

The method according to claim 1,
The organic light emitting device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer comprises a light emitting layer containing the pyrimidine derivative. A pyrimidine derivative represented by the following formula (2).
(2)

[In the formula (2)
R ₁ to R _3, R ₅ and R ₆ independently of one another are (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;
R < ₇ > is (C6-C30) aryl;
L is (C6-C30) arylene;
n is an integer of 1 to 2;
Wherein R ₁ to R _3, the aryl of R ₅ and R _6, aryl and heteroaryl, and R ₇ of the (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C1-C30) (C3-C30) aryl, (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C1-C30) alkyl, nitro and hydroxy Can be.] delete

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