WO2014204234A1

WO2014204234A1 - Phenylanthracene derivative and organic light emitting device containing same

Info

Publication number: WO2014204234A1
Application number: PCT/KR2014/005421
Authority: WO
Inventors: 김윤희; 권순기; 이윤지
Original assignee: 경상대학교산학협력단
Priority date: 2013-06-19
Filing date: 2014-06-19
Publication date: 2014-12-24
Also published as: KR101751784B1; KR20140147743A

Abstract

The present invention relates to a phenylanthracene derivative and an organic light emitting device containing the same in a light emitting layer. The organic light emitting device containing the phenylanthracene derivative according to the present invention has high thermal stability and remarkable luminous efficiency.

Description

Phenylanthracene derivative and organic light emitting device comprising the same

The present invention relates to a novel phenylanthracene derivative and an organic light emitting device comprising the same in a light emitting layer, and more particularly to an asymmetric, highly twisted phenylanthracene derivative.

As the development of the IT field has progressed rapidly and rapidly, the display field needs to upgrade its ability to express information accordingly, and the display field has grown together. Liquid Crystal Display (LCD), which has been used mainly for display windows of TVs, notebooks, and mobile phones until recently, is not only thick because it is a backlight that emits light from behind, but also is seen from the side because of low color purity, luminous efficiency, and narrow viewing angle. It has many disadvantages such as not being left and afterimage remains due to slow reaction speed. As a solution to this, many companies have actively researched organic light-emitting diodes (OLEDs). OLED is a self-luminous type that does not require backlight, and the response speed is faster than LCD in almost all aspects such as fast and low DC driving voltage, wide viewing angle, light weight, and flexible display possibility. It has been attracting attention and recently it is recognized as a core technology of display with the application of technology. However, there are still problems in efficiency and color purity, so it is urgent to develop a blue organic light emitting material for easier practical use of OLED.

The structure of an organic EL device is generally an anode, a hole injection layer (HIL), a hole transfer layer (HTL), an emission layer (EML), an electron transfer layer (ETL) ), An electron injection layer (EIL), and a cathode, which are formed by thermal evaporation under high vacuum (10 ^-6 to 10 ^-7 Torr). . The light emitting mechanism first injects holes in the anode and electrons in the cathode, and they meet in the light emitting layer to form unstable excitons. This unstable excitons stabilize and release energy, which is released as light energy. As the OLED is driven by this principle, the light emitting material is also important, but it is also essential that electrons and holes must meet in the light emitting layer, and thus the role of injecting and transferring electrons and holes is also important.

The color of light emitted from the OLED is determined by the difference in energy level between HOMO and LUMO of the light emitting material. When the energy difference increases, the light of short wavelength is emitted, and when the energy difference decreases, the light of long wavelength is emitted. The energy spacing between HOMO-LUMO can be controlled by varying the conjugation length of the molecule using the Linear Combination of Atomic Orbital (LCAO) method. As a result, the longer the conjugation, the smaller the band gap, and the corresponding wavelength becomes longer. OLEDs need three primary colors of light: red, green, and blue to display all the colors of nature. However, the development of high-efficiency blue light emission has become a problem for the practical use of OLED, which has a problem in that the blue light emitting material deteriorates the performance of the entire device due to the low color purity and lifetime compared to other materials.

On the other hand, the Republic of Korea Patent Publication No. 2008-0051625 "Anthracene derivatives and organic electroluminescent device comprising the same", but described with respect to the organic electroluminescent device comprising an anthracene derivative, the structure is different from the present invention The effect is not sufficient in terms of color purity and luminous efficiency.

The present invention relates to a phenylanthracene derivative, and more particularly, has a high thermal stability, optical properties and chemical stability by substituting a functional group capable of giving a high degree of distortion in the molecule of the anthracene derivative in the anthracene skeleton, and having an intramolecular or intermolecular interaction. It provides a phenylanthracene derivative that can have a high luminous efficiency with a minimum of action.

The present invention also provides an anthracene derivative having high color purity and high luminous efficiency including the phenylanthracene derivative and an organic light emitting device including the same as a light emitting material (a blue light emitting material and a blue fluorescent host).

In one aspect of the present invention for achieving the above object, the present invention provides a phenylanthracene derivative represented by the following formula (1).

[Formula 1]

[In Formula 1,

R ₁ to R ₄ are independently of each other hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkoxy or C ₆ -C ₃₀ aryl;

X is

or

R ₁₁ and R ₁₂ are each independently hydrogen, C ₁ -C ₃₀ alkyl or C ₁ -C ₃₀ alkoxy;

Y is C ₆ -C ₃₀ aryl or C ₃ -C ₃₀ heteroaryl;

p is an integer from 1 to 7;

q is an integer of 1 to 9, and each of R ₁₁ and when p and q are 2 or more; R ₁₂ may be the same or different from each other;

Aryl or heteroaryl of Y may be further substituted with C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkoxy, C ₃ -C ₃₀ heteroaryl or C ₆ -C ₃₀ aryl.]

Preferably, in Formula 1, Y may be selected from the following structures.

[Wherein R ₂₁ to R ₂₅ are each independently hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkoxy or C ₆ -C ₃₀ aryl;

o and p are integers from 1 to 4;

r is an integer of 1 to 6, and when o, p and q are two or more, R ₂₁ to R ₂₅ may be the same or different from each other.]

More preferably Y is

Wherein R ₂₁ is independently of each other hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkoxy or C ₆ -C ₃₀ aryl;

o is an integer from 1 to 4).

Preferably, the phenylanthracene derivative of Chemical Formula 1 may be represented by the following Chemical Formula 2 in terms of improving thermal stability and efficiency of the organic light emitting device including the same.

[Formula 2]

[In Formula 2,

R ₁₁ or R ₂₁ are independently of each other hydrogen, C ₁ -C ₃₀ alkyl or C ₁ -C ₃₀ alkoxy;

r is an integer from 1 to 4,

p is an integer of 1 to 7, and each of R ₁₁ or R ₂₁ may be different or the same when r and p are 2 or more.]

Preferably, the phenylanthracene derivative according to an embodiment of the present invention in order to increase the thermal stability and efficiency of the organic light-emitting device including the same in Formula 1 R ₁ or R ₄ is hydrogen, R ₂ to R ₃ is hydrogen or C ₁ -C ₃₀ alkyl, more preferably C ₁ -C ₁₂ alkyl.

The phenyl anthracene derivative represented by Formula 1 of the present invention may be selected from the following compounds, but is not limited thereto.

In another aspect, the present invention provides an organic light emitting device including a light emitting layer between an anode, a cathode, and a positive electrode, and includes a phenylanthracene derivative according to the present invention in a light emitting layer.

The present invention also relates to an organic light emitting device using the phenylanthracene derivative according to the present invention as a light emitting material having an electron transport ability.

The phenylanthracene derivative according to the present invention may be prepared according to Scheme 1, for example, but may be prepared by a synthetic method that can be recognized by those skilled in the art.

Scheme 1

[In Scheme 1,

X, R ₁ to R ₄ , and Y are the same as defined in Formula 1 above;

Ha is halogen.]

In another aspect, the present invention provides an organic light emitting device comprising a light emitting layer between the anode, the cathode and the positive electrode, the organic light emitting device comprising a phenylanthracene derivative according to the present invention in the light emitting layer. The phenylanthracene derivative according to the present invention is a light emitting material having an electron transport ability, and the organic light emitting device including the same has a high quantum efficiency, a low driving voltage, and a high luminous efficiency.

The phenylanthracene derivative according to the present invention has a highly twisted structure due to the high rotational disturbance of the substituents of anthracene skeleton and anthracene, and thus exhibits a high glass transition temperature and the interaction between the anthracene molecules is suppressed to the maximum, resulting in a high color purity emission spectrum. You can appear.

Therefore, the OLED including the phenylanthracene derivative according to the present invention has a problem of deterioration due to driving heat generated during driving of the device and a decrease in emission characteristics and color purity due to low purity and pi-stacking of the material for forming an organic film. It is possible to solve the problem, improve the luminous efficiency, and improve the stability of the device, it is possible to provide a high-efficiency high color electroluminescent device for the reason that the intermolecular interference due to strong distortion is reduced.

The phenylanthracene derivative according to the present invention has an asymmetric structure, and the substituents of the anthracene skeleton and the anthracene, in particular pyridinylphenyl and naphthalenyl or pyridinylphenyl and pyrenyl, have a high rotational disorder and thus show a highly twisted structure. It exhibits a high glass transition temperature, and the anthracene intermolecular interaction is suppressed as much as possible, resulting in a high color purity emission spectrum.

Therefore, the OLED having an organic film such as a light emitting layer formed by using the asymmetric phenylanthracene derivative according to the present invention has a problem due to heat generated during driving, low purity of the organic film forming material, degradation of luminescence properties and color purity due to π-stacking As a result, the luminous efficiency is improved, the stability of the device is improved, and the intermolecular interference due to the high distortion is reduced, so that a light emitting device having high efficiency and high color purity can be formed.

In addition, the asymmetric phenylanthracene derivative according to the present invention can be used as a host material of a conventionally known blue fluorescent material, so that the OLED of the present invention can realize excellent blue color purity.

1 is a thermogravimetric analysis (TGA) graph of Compound 1 prepared in Example 1,

2 is a differential calorimetry (DSC) graph of Compound 1 prepared in Example 1,

FIG. 3 is a graph showing liquid UV absorption and PL spectrum of compound 1 prepared in Example 1 and PL spectrum in solid state,

FIG. 4 is a cyclic voltammetry curve graph of Compound 1 prepared in Example 1. FIG.

FIG. 5 is a diagram illustrating a measurement result of Density Functional Theory (DFT) of Compound 1 prepared in Example 1. FIG.

6 is a view showing a DFT measurement result of Compound 2 prepared in Example 2. FIG.

7 is a diagram showing a DFT measurement result of Compound 3 prepared in Example 3. FIG.

Hereinafter, the phenylanthracene derivative according to the present invention, the preparation method thereof, and the luminescence properties of the device will be described with reference to the representative compounds of the present invention for a detailed understanding of the present invention, but only for the purpose of illustrating the embodiments of the present invention. It does not limit the scope of the invention.

Hereinafter, physical properties were measured by the following method.

1. Evaluation of Thermal Properties of Phenylanthracene Derivatives

The thermal properties were measured by thermogravimetric analysis (TGA) and differential calorimetry (DSC) by heating from 40 ° C. to 700 ° C. at 10 ° C. per minute under a nitrogen atmosphere.

2. Measurement of Absorption and Luminescence of Phenylanthracene Derivatives

A phenylanthracene derivative was prepared at a concentration of 10 ^-5 M to measure UV-VIS and PL spectra.

3. Electrochemical Characterization of Phenylanthracene Derivatives

Phenylanthracene derivatives were prepared at a concentration of 10 ^-5 M and measured by cyclic voltammetry.

4. Electron density measurement of phenylanthracene derivatives

The Spartna'08 program with B3LYP theory was used to measure HOMO and LUMO values based on 6-31G ^** .

[실시예 1] 화합물 1의 제조Example 1 Preparation of Compound 1

화합물 A의 제조Preparation of Compound A

To a 500 mL three necked flask was added 2-bromonaphthalene (20.0 g, 96.6 mmol) and tetrahydrofuran (THF; tetrahydrofuran) (100 mL). After cooling to −78 ° C., n-Butyllithium (2.5 M in hexanes, 42.4 mL, 106.2 mmol) was slowly added to the reactor for 30 minutes by using a syringe. After 1 hour, triethylborate ( 18 mL, 106.2 mmol) was added thereto, followed by further stirring for 12 hours. To terminate the reaction, 100 mL of 2 M hydrochloric acid solution was added, and after 1 hour, 200 mL of methylene chloride and 150 mL of distilled water were added and extracted. The extracted organic layer was evaporated after removing moisture with magnesium sulfate. After washing with excess n-hexane, the resultant was filtered with a glass filter to obtain a white Compound A (2.85 g, 77,4%). The structure of the obtained Compound A was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.38 (s, 1H), 8.17 (s, 2H), 7.83-7.94 (m, 4H), 7.47-7.55 (m, 2H)

화합물 B의 제조Preparation of Compound B

In a 500 mL three-neck flask, Compound A (30.10 g, 175.01 mmol), 9-bromoanthracene (30.0 g, 116.67 mmol), Pd (PPh ₃ ) ₄ (1.02 g, 0.01 mmol) and potassium carbonate solution (2 M, 100 mL) was added, and tetrahydrofuran (THF; tetrahydrofuran) (250 mL) was added to dissolve and reacted at a temperature of 85 ° C. for 24 hours. After completion of the reaction, the mixture was extracted with chloroform (300mL × 2), and then the water of the organic layer was removed, and then the organic solvent was removed. Compound B (yield: 67%) was obtained by column chromatography using hexane. The structure of the obtained compound B was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ³ ): δ 8.54 (s, 1H), 7.98-8.09 (m, 4H), 7.89-7.95 (m, 2H), 7.69-7.72 (m, 2H), 7.57-7.61 ( m, 3H), 7.44-7.50 (m, 2H), 7.30-7.34 (m, 2H)

화합물 C의 제조Preparation of Compound C

In a 500 mL three neck flask, Compound B (9 g, 29.51 mmol) was dissolved in dimethylamide (50 mL), and dimethylamide (200 mL) solution containing N-bromosuccinimide (5.7 g, 32.46 mmol) was dissolved. The addition was slow and the reactor was stirred for 2 hours after all additions. After distilled water was added and the reaction product was filtered through a glass filter, the obtained compound was washed with 2 L of distilled water and dried to obtain Compound C. The structure of Compound C was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.67-8.65 (d, 2H), 7.99-8.07 (m, 2H), 7.84-7.89 (m, 2H), 7.64-7.66 (d, 2H), 7.56- 7.60 (m, 4H), 7.50-7.52 (m, 1H), 7.32-7.35 (m, 2H)

화합물 D의 제조Preparation of Compound D

Compound C (20 g, 52.18 mmol) was added to tetrahydrofuran (THF; tetrahydrofuran) (200 mL) and dissolved in a 500 mL three neck flask. After cooling to −78 ° C., n-butyllithium (2.5 M in hexanes, 23.0 mL, 57.40 mmol) was slowly added using a syringe for 20 minutes. After stirring for 1 hour, triethyl borate (9.7 mL, 57.40 mmol) was added, followed by further stirring for 12 hours. In order to terminate the reaction, 180 mL of 2 M hydrochloric acid solution was added, and after 1 hour, 200 mL of methylene chloride and 150 mL of distilled water were added to extract only the organic layer, and the organic layer was evaporated after removing water with magnesium sulfate. The material thus obtained was washed with an excess of n-hexane, filtered with a glass filter, washed with toluene heated to 50 ° C., filtered, and dried to obtain a white Compound D. The obtained compound D had a structure of 1H-NMR. Confirmed.

¹ H NMR (300 MHz, CDCl ₃ ): δ 5.25 (s, 2H), 7.35 (t, 2H), 7.51-7.47 (m, 3H), 7.67 (t, 2H), 7.70 (d, 2H), 7.89 (m, 2H), 8.06-8.00 (m, 2H), 8.19 (d, 2H)

화합물 E의 제조Preparation of Compound E

Compound D (1 g, 2.87 mmol), 2,5-dibromo-1,4-dimethylbenzene (1.12 g, 4.31 mmol), Pd (PPh ₃ ) ₄ (0.09 g, 0.03 mmol) in a 100 mL three neck flask And aqueous sodium hydroxide solution (2 M, 4.3 mL) were added followed by mixing with tetrahydrofuran (20 mL) and toluene (10 mL). And it is made to react at temperature 85 degreeC for 12 hours. After completion of the reaction was extracted with chloroform (300mL × 2), and the solvent was removed after removing the moisture of the extracted organic layer. Then, ether was charged to the sample, stirred, and purified first, followed by column chromatography with hexane: chloroform = 5: 1 to obtain Compound G. The structure of Compound G was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.03-8.12 (m, 3H), 7.93-7.98 (m, 2H) 7.74-7.76 (m, 2H), 7.68 (s, 1H), 7.58-7.64 (m , 5H), 7.30-7.40 (m, 4H), 7.22 (d, 1H), 2.48 (s, 1H), 1.58 (s, 1H);

화합물 1의 제조Preparation of Compound 1

Compound G (3.2 g, 6.57 mmol), 4-pyridineboronic acid (1.6 g, 13.13 mmol), Pd (PPh ₃ ) ₄ (0.08 g, 0.06 mmol), sodium hydroxide solution (2 M, 25 ml) was added, followed by dissolution by addition of tetrahydrofuran (100 mL) and the reaction was carried out at 90 ° C. for 36 hours. After completion of the reaction, the mixture was extracted with chloroform (300mL × 2), and then the moisture of the organic layer was removed and the solvent was removed. Compound 1 was obtained by column chromatography, and the obtained compound 1 was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.85 (d, 2H), 7.98-8.11 (m, 4H), 7.75-7.78 (d, 2H), 7.63-7.69 (m, 51H), 7.49-7.51 ( d, 2H), 7.34-7.44 (m, 5H), 7.29 (s, 1H), 2.40 (s, 3H), 1.98 (s, 3H); HRMS (EI) m / z calcd for C 37 H 27 N (M ⁺ ): 485.2143; found 465.2144

Physical properties of the prepared compound 1 was measured by the method described above to obtain the graph of FIGS. 1 to 4.

As shown in FIG. 1, 5% weight loss of the compound 1, which is a phenylanthracene derivative, was measured at about 320 ° C., which shows that the phenylanthracene derivative synthesized in the present invention has excellent thermal stability. .

In FIG. 2, it can be seen that the material has crystallinity by confirming that a peak appears at about 289 ° C. in the first heating section.

In addition, as shown in FIG. 3, the UV spectrum of the liquid state of Compound 1 prepared in Example 1 was measured to be absorbed at about 260 nm, and the PL spectrum was measured to emit light at about 430 nm.

Electrochemical properties were measured by cyclic voltammetry and the results are shown in FIG. 4. 4, the HOMO was 5.59 eV, the LUMO was 2.59 eV, and the band gap was measured at 3.0.

In addition, as shown in FIG. 5, Compound 1 prepared in Example 1 of the present invention has a pyridinylphenyl group instead of a pyridinyl group in the anthracene skeleton, so that the pyridinyl group may be formed between the pyridinyl and the anthracene skeleton in spite of being an electron withdrawing group. The phenyl group present blocks the electron attraction effect of the pyridinyl group, concentrating the electron density on the anthracene skeleton, resulting in high color purity and luminous efficiency.

That is, Compound 1 of the present invention has a pyridinylphenyl group substituted on one side of the anthracene skeleton and a naphthalenyl group on one side, so that it has a highly twisted structure and concentrates on the electron density anthracene skeleton, and thus has very high color purity and luminous efficiency. .

Example 2 Preparation of Compound 2

화합물 A의 제조Preparation of Compound A

To a 500 mL three necked flask was added 2-bromonaphthalene (20.0 g, 96.6 mmol) and tetrahydrofuran (THF; tetrahydrofuran) (100 mL). After cooling to −78 ° C., n-Butyllithium (2.5 M in hexanes, 42.4 mL, 106.2 mmol) was slowly added to the reactor for 30 minutes by using a syringe. After 1 hour, triethylborate ( 18 mL, 106.2 mmol) was added thereto, followed by further stirring for 12 hours. In order to terminate the reaction, 100 mL of 2 M hydrochloric acid solution was added, and after 1 hour, 200 mL of methylene chloride and 150 mL of distilled water were added and extracted. The extracted organic layer was evaporated after removing moisture with magnesium sulfate. After washing with excess n-hexane, the resultant was filtered with a glass filter to obtain a white Compound A (2.85 g, 77,4%). The structure of the obtained Compound A was confirmed by ¹ H-NMR.

화합물 B의 제조Preparation of Compound B

In a 500 mL three-neck flask, Compound A (30.10 g, 175.01 mmol), 9-bromoanthracene (30.0 g, 116.67 mmol), Pd (PPh ₃ ) ₄ (1.02 g, 0.01 mmol) and potassium carbonate solution (2 M, 100 mL) was added, and tetrahydrofuran (THF; tetrahydrofuran) (250 mL) was added to dissolve and reacted at a temperature of 85 ° C. for 24 hours. After completion of the reaction, the mixture was extracted with chloroform (300mL × 2), and then the moisture of the organic layer was removed, and then the organic solvent was removed. Compound B (yield: 67%) was obtained by column chromatography using hexane. The structure of the obtained compound B was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.54 (s, 1H), 7.98-8.09 (m, 4H), 7.89-7.95 (m, 2H), 7.69-7.72 (m, 2H), 7.57-7.61 ( m, 3H), 7.44-7.50 (m, 2H), 7.30-7.34 (m, 2H)

화합물 C의 제조Preparation of Compound C

화합물 D의 제조Preparation of Compound D

화합물 E의 제조Preparation of Compound E

Compound D (1 g, 2.87 mmol), 2,5-dibromo-1,4-dimethylbenzene (1.12 g, 4.31 mmol), Pd (PPh ₃ ) ₄ (0.09 g, 0.03 mmol) in a 100 mL three neck flask And aqueous sodium hydroxide solution (2 M, 4.3 mL) were added followed by mixing with tetrahydrofuran (20 mL) and toluene (10 mL). And it is made to react at the temperature of 85 degreeC for 12 hours. After completion of the reaction was extracted with chloroform (300mL × 2), and the solvent was removed after removing the moisture of the extracted organic layer. Then, ether was charged to the sample, stirred, and purified first, followed by column chromatography with hexane: chloroform = 5: 1 to obtain Compound G. The structure of Compound G was confirmed by ¹ H-NMR.

화합물 2의 제조Preparation of Compound 2

Compound G (3.2 g, 6.57 mmol), 2-pyridine boronic acid (1.6 g, 13.13 mmol), Pd (PPh ₃ ) ₄ (0.08 g, 0.06 mmol), sodium hydroxide solution (2 M, 25 ml) was added, followed by dissolution by addition of tetrahydrofuran (100 mL) and the reaction was carried out at 90 ° C. for 36 hours. After completion of the reaction, the mixture was extracted with chloroform (300mL × 2), and then the moisture of the organic layer was removed and the solvent was removed. Compound 2 was obtained by column chromatography, and the obtained compound 1 was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.83 (d, 2H), 7.98-8.11 (m, 4H), 7.75-7.78 (d, 2H), 7.63-7.69 (m, 51H), 7.49-7.51 ( d, 2H), 7.34-7.44 (m, 5H), 7.29 (s, 1H), 2.40 (s, 3H), 1.98 (s, 3H); HRMS (EI) m / z calcd for C 37 H 27 N (M ⁺ ): 485.2143; found 465.2144

Example 3 Preparation of Compound 3

화합물 A의 제조Preparation of Compound A

화합물 B의 제조Preparation of Compound B

화합물 C의 제조Preparation of Compound C

화합물 D의 제조Preparation of Compound D

화합물 E의 제조Preparation of Compound E

Compound D (1 g, 2.87 mmol), 2,5-dibromo-1,4-dimethylbenzene (1.12 g, 4.31 mmol), Pd (PPh ₃ ) ₄ (0.09 g, 0.03 mmol) in a 100 mL three neck flask And aqueous sodium hydroxide solution (2 M, 4.3 mL) were added followed by mixing with tetrahydrofuran (20 mL) and toluene (10 mL). And it is made to react at temperature 85 degreeC for 12 hours. After completion of the reaction was extracted with chloroform (300mL × 2), and the solvent was removed after removing the water of the extracted organic layer. Then, ether was charged to the sample, and the mixture was stirred and purified first, and then purified by column chromatography with hexane: chloroform = 5: 1 to obtain Compound G. The structure of Compound G was confirmed by ¹ H-NMR.

화합물 3의 제조Preparation of Compound 3

Compound G (3.2 g, 6.57 mmol), 3-pyridineboronic acid (1.6 g, 13.13 mmol), Pd (PPh ₃ ) ₄ (0.08 g, 0.06 mmol), sodium hydroxide solution (2 M, 25 ml) was added, followed by dissolution by addition of tetrahydrofuran (100 mL) and the reaction was carried out at 90 ° C. for 36 hours. After completion of the reaction, the mixture was extracted with chloroform (300mL × 2), and then the moisture of the organic layer was removed and the solvent was removed. Compound 2 was obtained by column chromatography, and the obtained compound 1 was confirmed by ¹ H-NMR.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.86 (d, 2H), 7.98-8.11 (m, 4H), 7.75-7.78 (d, 2H), 7.63-7.69 (m, 51H), 7.49-7.51 ( d, 2H), 7.34-7.44 (m, 5H), 7.29 (s, 1H), 2.40 (s, 3H), 1.98 (s, 3H); HRMS (EI) m / z calcd for C 37 H 27 N (M ⁺ ): 485.2143; found 465.2144

6 shows the DFT of Compound 2 prepared in Example 2, and FIG. 7 shows the DFT of Compound 3 prepared in Example 3. FIG.

As shown in Fig. 6 and 7, the compounds of Examples 2 to 3, like the compound 1 of the present invention, also have a pyridinylphenyl group substituted on one side of the anthracene skeleton and a naphthalenyl group on the other side, thus providing a highly twisted structure. The electron density is concentrated in the anthracene skeleton, but the color purity and luminous efficiency are very high.

Claims

A phenylanthracene derivative represented by the following formula (1).

[Formula 1]

[In Formula 1,

R 1 to R 4 are independently of each other hydrogen, C 1 -C 30 alkyl, C 1 -C 30 alkoxy or C 6 -C 30 aryl;

X is
or
R 11 and R 12 independently of one another are hydrogen, C 1 -C 30 alkyl or C 1 -C 30 alkoxy;

Y is C 6 -C 30 aryl or C 3 -C 30 heteroaryl;

p is an integer from 1 to 7;

q is an integer from 1 to 9 and when p and q are 2 or more, R 11 and R 12 may be different or the same;

Aryl or heteroaryl of Y may be further substituted with C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 3 -C 30 heteroaryl or C 6 -C 30 aryl.]
The method of claim 1,

Y is phenylanthracene derivative selected from the following structures.

[Wherein R 21 to R 25 are each independently hydrogen, C 1 -C 30 alkyl, C 1 -C 30 alkoxy or C 6 -C 30 aryl;

o and p are integers from 1 to 4;

r is an integer of 1 to 6, and when o, p and q are two or more, R 21 to R 25 may be the same or different from each other.]
The method of claim 1,

Formula 1 is a phenylanthracene derivative represented by the following formula (2).

[Formula 2]

[In Formula 2,

R 1 to R 4 are independently of each other hydrogen, C 1 -C 30 alkyl, C 1 -C 30 alkoxy or C 6 -C 30 aryl;

R 11 or R 21 are independently of each other hydrogen, C 1 -C 30 alkyl or C 1 -C 30 alkoxy;

r is an integer from 1 to 4,

p is an integer of 1 to 7, and each of R 11 and R 21 may be different or the same when p and r are 2 or more.]
The method of claim 1,

R 1 or R 4 is hydrogen;

R 2 to R 3 are hydrogen or C 1 -C 30 alkyl.
The method of claim 1,

Formula 1 is a phenylanthracene derivative selected from the following compounds.
An organic light emitting device comprising a light emitting layer between an anode, a cathode and a positive electrode, the organic light emitting device comprising a phenylanthracene derivative according to any one of claims 1 to 5 in a light emitting layer.
The method of claim 6,

An organic light emitting device using the phenylanthracene derivative as a host material.