KR100828169B1 - Organic Electroluminescent Compounds with Hgh Efficiency and Display Device using The Same - Google Patents

Abstract

The present invention relates to an organic light emitting compound containing a fluorenyl group and to an organic light emitting device including the same, and in detail, an organic light emitting compound represented by the following Chemical Formula 1.

[Formula 1]

The organic light emitting compound according to the present invention exhibits superior EL characteristics than conventional host materials.

Luminescent, Floren, Organic Luminescent, Antryl

Description

Organic Electroluminescent Compounds with Hgh Efficiency and Display Device using The Same}

The present invention relates to a novel organic light emitting compound, a method for producing the same, and an organic electroluminescent device employing the same as a light emitting material.

One of the flat panel displays, the organic light-emitting diode (OLED) is self-luminous, so it has better viewing angle, contrast ratio, etc. than LCD, and can simplify the process and light weight because it does not require backlight. In addition, it is advantageous in terms of power consumption, and intensive R & D is being done. In particular, since the performance of the OLED panel is highly dependent on the characteristics of the organic light emitting compound used, research on the light emitting material is being actively conducted.

The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task. Especially, considering the level of EL characteristics required for medium and large OLED panels, it is urgent to develop materials that are superior to existing light emitting materials. In this respect, the development of host materials is one of the most important factors to be solved.

To this end, the desirable properties of the host material, which acts as a solid solvent and energy carrier, should be of high purity and have a suitable molecular weight to enable vacuum deposition. In addition, high glass transition temperature and pyrolysis temperature should ensure thermal stability, high electrochemical stability is required for long life, easy to form amorphous thin film, good adhesion with other adjacent materials, Should not.

Many host materials have been published in the past, such as diphenylvinyl-biphenyl (DPVBi) and Kodak's Dnaphthyl-Anthracene (DNA) from Kodak, but many improvements have been made in terms of efficiency, lifetime and color purity. There is room for it.

Di-pyrenylprolene (DPF) and bis-phenylintricene-spirofluorene (BPA-SP) with various structures have been developed to develop high-efficiency and long-life host materials. It was not a satisfactory level.

In the case of DPF published by Canon in Saitoh, A. et. Al. Digest of tech.papers-SID 2004, 35, 686; U.S. Patent No. US 2005236977 using a dopant of diprorenylprolene (DFF) The external quantum efficiency of 3.9% and the relatively good EL characteristics of (0.15, 0.14) were shown under the optimal doping conditions, but the commercialization level was also insufficient. In addition, in the case of BPA-SP (Shen, W.-J. et.al. Chemistry of Materials, 2004, 16, 930; U.S. Patent No. US 2002122900), the luminous efficiency of 2.67 cd / A and (0.15, 0.11) are relatively high. Although it showed good color coordinates, it was also insufficient for commercialization.

An object of the present invention is to provide an organic light emitting compound having better luminous efficiency than a conventional host material, having an excellent color coordinate, and an organic light emitting device containing the organic light emitting compound.

The present invention relates to an organic light emitting compound represented by Chemical Formula 1 and an organic light emitting diode (OLED) employing the same as a light emitting material.

[Formula 1]

In Formula 1, A and B are independently a chemical bond or arylene of C ₆ -C ₃₀ ; Ar ₁ and Ar ₂ are each independently an aryl group of C ₆ -C ₃₀ ; Ar ₃ to Ar ₉ are each independently hydrogen, C ₁ -C ₂₀ straight or branched alkyl or alkoxy group, C ₆ -C ₃₀ aryl or heteroaryl group, halogen group; R ₁ and R ₂ are each independently hydrogen, a straight or branched chain alkyl group of C ₁ -C ₂₀ , or an aryl group of C ₆ -C ₃₀ , or R ₁ and R ₂ are each other an alkylene or fused ring alkylene Combine to form a spiro ring; Ar ₁₀ is hydrogen, a C ₁ -C ₂₀ straight or branched alkyl group, C ₆ -C ₃₀ aryl group or halogen; The arylene group, aryl group, heteroaryl group, alkyl group, alkoxy group may be further substituted with C ₁ -C ₂₀ linear or branched alkyl, diarylamino group, halogen group.

In the organic light emitting compound according to the present invention, Ar ₁₀ is specifically phenyl, naphthyl, anthryl or florenyl, wherein Ar ₁₀ is C ₁ -C ₂₀ straight or branched chain alkyl, phenyl, naphthyl, florenyl One or more selected from a diarylamino group and a halogen group may be further substituted.

In addition, the organic light emitting compound according to the present invention includes a compound of formula (2) wherein Ar ₁₀ contains an anthryl group.

[Formula 2]

Ar ₁ to Ar ₉ in Formula 2 are the same as defined in claim ₁ ; Ar ₁₁ and Ar ₁₂ are each independently an aryl group of C ₆ -C ₃₀ ; Ar ₁₃ to Ar ₁₉ are each independently hydrogen, C ₁ -C ₂₀ straight or branched chain alkyl or alkoxy group, C ₆ -C ₃₀ aryl or heteroaryl group, halogen group; The aryl group, heteroaryl group, and alkyl group may be further substituted with C ₁ -C ₂₀ linear or branched alkyl, aryl group, diarylamino group, halogen group.

In Formula 1 and Formula 2 R ₁ and R ₂ are specifically independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl each other, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl , Decyl, dodecyl, hexadecyl, cyclopentyl, cyclohexyl, phenyl, tolyl, biphenyl, benzyl, naphthyl, anthryl and florenyl, and Ar ₁ , Ar ₂ , Ar ₁₁ and Ar ₁₂ are independent of each other Phenyl, tolyl, biphenyl, benzyl, naphthyl, anthryl and florenyl.

The organic light emitting compound according to the present invention includes the following formulas (3) and (4).

[Formula 3]

[Formula 4]

In Formulas 3 and 4, A and B may be each independently a chemical bond or 1,4-phenylene, 1,3-phenylene, 1,4-naphthylene, 1,5-naphthylene or 2,6-naph Styrene; Ar ₁ , Ar ₂ , Ar ₁₁ and Ar ₁₂ independently of one another are phenyl, 4-tolyl, 3-tolyl, 2-tolyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, (3,5-di Phenyl) phenyl, 9,9-dimethyl-floren-2-yl, 9,9-diphenyl-floren-2-yl, (9,9- (4-methylphenyl) -floren-2-yl, 1 -Naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 3-anthryl, 2-spiroprene.

The organic light emitting compound according to the present invention may be exemplified by the following formula, but the illustrated compound does not limit the scope of the present invention.

[Production Example 1]

Preparation of 101 Compound

Tetrahydrofuran (3.5 L, 0.3 M) was added to bromobenzene (388 g, 2.47 mol), stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C. Then, n-butyllithium (1.6 M in n- Hexane) (1.7 L, 2.68 mol) is slowly added dropwise. After 1 hour, 2-chloroanthraquinone (250 g, 1.03 mol) is added, and the temperature is slowly raised to room temperature, followed by stirring for 24 hours. 1 L of 10% HCl solution was added, stirred for 2 hours, and filtered under reduced pressure. The organic layer was separated and evaporated to give 1 compound (226 g, 55%) as a brown transparent oil.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.17-7.20 (m, 14H), 7.31 (d, 2H), 7.35 (s, 1H)

MS / FAB: 398.61 (found), 398.88 (calculated)

1 compound (226 g, 0.56 mol) potassium iodide (376 g, 2.27 mol), sodium phosphate monohydrate (480 g, 0.45 mol) and acetic acid (1.9 L, 0.3 M) were added and stirred under reflux. After 18 hours, the mixture was cooled to room temperature and filtered under reduced pressure. A small amount of potassium carbonate, dichloromethane and distilled water were added to the solid obtained after filtration under reduced pressure to make neutral, and after stirring for 2 hours, the organic layer was separated and evaporated to give 2 compound (97.2 g, 47%) as a dark yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.23 (t, 2H), 7.31-7.32 (m, 6H), 7.34 (d, 1H), 7.49 (d, 4H), 7.65 (d, 2H), 7.68 (d, 1H), 7.70 (s, 1H)

MS / FAB: 364.95 (found), 364.86 (calculated)

2 compounds (97.2 g, 0.27 mol) and tetrahydrofuran (0.89 L, 0.3 M) were added and stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C, followed by n-butyllithium (1.6M in n-hexane ) (0.216 L, 0.35 mol) is slowly added dropwise. After 1 hour, triisopropylborate (80.2 g, 0.43 mol) is added, and then slowly heated to room temperature and stirred for 24 hours. 0.5 L of 10% HCl solution was added, stirred for 2 hours, and filtered under reduced pressure. The organic layer was separated and evaporated, and recrystallized with hexane and methanol to obtain 3 compound (36.9 g, 37%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.21 (t, 2H), 7.28 (d, 1H), 7.30-7.32 (m, 6H), 7.48 (d, 4H), 7.65 (d, 2H), 7.70 (d, 1H), 7.72 (s, 1H)

MS / FAB: 374.58 (found), 374.23 (calculated)

Add 2-bromoflorene (20 g, 82 mmol), iodomethane (35 g, 0.25 mol), potassium hydroxide (13.8 g, 0.25 mol), dimethyl sulfoxide (0.16 L, 0.5 M) and stir at room temperature . After 24 hours, 0.2 L of 10% hydrochloric acid was added, stirred for 10 minutes, and filtered under reduced pressure. The resulting solid was recrystallized using hexane and methanol to give 4 compound (14.75 g, 54%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.25 (t, 1H), 7.30 (t, 1H), 7.52-53 (d, 2H), 7.71-73 ( d, 2H), 7.81 (s, 1H)

MS / FAB: 272.09 (found), 273.16 (calculated)

3 compound (10 g, 26.72 mmol), 4 compound (8.76 g, 32.06 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.38 g, 0.54 mmol), sodium carbonate (5.67 g, 53.44 mmol), Toluene (0.1 L, 0.3 M) and distilled water (9 mL, 3 M) were added and stirred under reflux. After 22 hours, the temperature was lowered to room temperature, and 0.1 L of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was subjected to silica gel column chromatography (dichloromethane: n-n-Hexane = 1: 10) to obtain 101 compound (8.52 g, 61%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.66 (s, 6H), 7.20 (t, 2H), 7.30-7.47 (m, 12H), 7.51-7.58 (m, 3H), 7.68- 7.71 (m, 3H), 7.75 (s, 1H), 7.84-7.85 (s, 2H), 7.92 (s, 1H)

MS / FAB: 522.80 (found), 522.67 (calculated)

[Production Example 2]

Preparation of 102 Compound

2,7-dibromoflorene (146 g, 0.45 mol), iodomethane (192 g, 1.351 mol), potassium hydroxide (76 g, 1.351 mol), dimethylsulfoxide (1.125 L, 0.4 M), distilled water ( 1.125 L, 0.4 M) is added and stirred at room temperature. After 24 hours, 2 L of 10% hydrochloric acid was added, stirred for 10 minutes, and filtered under reduced pressure. The obtained oil was purified by silica gel column chromatography (dichloromethane: n-Hexane = 1: 10) to give 5 compound (93 g, 59%) as a pink solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.54 (d, 2H), 7.70-7.73 (d, 4H)

MS / FAB: 351.67 (found), 352.06 (calculated)

3 compound (23 g, 61.46 mmol), 5 compound (21.64 g, 61.46 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.216 g, 0.307 mmol), sodium carbonate (7.82 g, 73.75 mmol), Toluene (0.2 L, 0.3 M) and distilled water (20 mL, 3 M) were added and stirred under reflux. After 26 hours, the temperature was lowered to room temperature and 0.2 L of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was subjected to silica gel column chromatography (Ethylacetate: n-Hexane = 1:15) to give 6 compound (9.6 g, 26%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.66 (s, 6H), 7.20 (t, 2H), 7.30-7.41 (m, 10H), 7.52-7.54 (d, 2H), 7.62- 7.64 (m, 3H), 7.71-7.76 (m, 4H), 7.87 (s, 1H), 7.91 (d, 1H)

MS / FAB: 601.26 (found), 601.57 (calculated)

6 compound (9.6 g, 15.96 mmol), phenylboronic acid (2.34 g, 19.15 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.224 g, 0.32 mmol), sodium carbonate (3.38 g, 31.92 mmol) Toluene (53 mL, 0.3 M) and distilled water (5.3 mL, 3 M) were added and stirred under reflux. After 18 hours, the temperature was lowered to room temperature and 0.05 L of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was subjected to silica gel column chromatography (Ethylacetate: n-n-Hexane = 1: 5) to obtain 102 compound (3.92 g, 41%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.21 (t, 3H), 7.31-7.43 (m, 14H), 7.54-7.68 (m, 5H), 7.73- 7.76 (d, 3 H), 7.89-7.91 (d, 3 H)

MS / FAB: 598.12 (found), 598.77 (calculated)

[Production Example 3]

108 Preparation of Compound

Diethyl ether (0.05 L, 2 M) is added to magnesium (4.9 g, 0.2 mol), and bromobenzene (31.4 g, 0.2 mol) diluted in diethyl ether (0.15 L, 0.67 M) is slowly added dropwise. Reflux for 3 hours with stirring. Dissolve 2-bromofluorenone (25.9 g, 0.1 mol) in diethyl ether (0.04 L, 2.5 M) and add it dropwise to the mixture which is stirred under reflux using a syringe. The reaction is terminated after 12 hours. The resulting precipitate was filtered under reduced pressure to give 7 compound (15 g, 18%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.18 (d, 2H), 7.20-7.26 (m, 4H), 7.36 (t, 1H), 7.54 (d, 2H), 7.71-7.73 ( d, 2H), 7.83 (d, 1H)

MS / FAB: 337.01 (found), 337.20 (calculated)

7 Compound (15 g, 36 mmol) is dissolved in benzene (0.145 L, 0.25 M) and heated. Methanesulfonic acid (6.6 mL, 72 mmol) is slowly added dropwise while heating. After 30 minutes the reaction is complete. Recrystallization with methanol and petroleum diethyl ether gave 8 compounds (9.58 g, 67%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.05-7.08 (m, 6H), 7.13-7.15 (m, 4H), 7.27 (t, 1H), 7.36 (t, 1H), 7.54 ( d, 2H), 7.71-7.73 (d, 2H), 7.83 (d, 1H)

MS / FAB: 396.89 (found), 397.30 (calculated)

3 compound (6.94 g, 18.55 mmol) and 8 compound (9.58 g, 24.11 mmol) prepared in Preparation Example 1, trans-dichlorobistriphenylphosphinepalladium (II) (0.39 g, 0.56 mmol), sodium carbonate (4.92 g, 46.38 mmol), toluene (62 mL, 0.3 M), distilled water (6.2 mL, 3 M) were added and stirred under reflux. After 45 hours, the temperature was lowered to room temperature, and 0.06 L of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was recrystallized using diethyl ether, hexane and methanol, and silica gel column chromatography (dichloromethane: n-n-Hexane = 1: 3) yielded 108 compound (4.56 g, 38%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.05-7.08 (m, 6H), 7.17-7.28 (m, 7H), 7.34-7.46 (m, 11H), 7.54-7.60 (m, 3H ), 7.68-7.74 (m, 4H), 7.86-7.90 (m, 3H)

MS / FAB: 646.77 (found), 646.81 (calculated)

[Production Example 4]

109 Preparation of the Compound

Diethyl ether (10 mL, 2 M) was added to magnesium (1.86 g, 25.6 mmol), and 2-bromobiphenyl (5 g, 21.6 mmol) diluted in diethyl ether (20 mL, 1 M) was slowly added dropwise. . Reflux for 3 hours. Dissolve 2-bromofluorenone (5.2 g, 20 mmol) in diethyl ether (40 mL, 0.5 M) and add it dropwise to the refluxed mixture using a syringe. The reaction is terminated after 12 hours. The resulting solid is filtered off and dissolved in 40 mL of acetic acid solution to reflux. To this is slowly added dropwise concentrated hydrochloric acid. After 4 hours the reaction is complete. The resulting solid was washed with water and methanol with filtration under reduced pressure, and recrystallized with dichloromethane and hexane to obtain 10 compound (6.85 g, 66%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.15-7.20 (m, 4H), 7.26 (t, 2H), 7.36-7.38 (m, 4H), 7.54 (d, 2H), 7.72- 7.73 (d, 2 H), 7.86 (d, 1 H)

MS / FAB: 394.76 (found), 395.29 (calculated)

3 compound (4.99 g, 13.33 mmol) prepared in Preparation Example 1, 10 compound (6.85 g, 17.3 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.28 g, 0.40 mmol), sodium carbonate (3.53 g, 33.33 mmol), toluene (40 mL, 0.33 M) and distilled water (4 mL, 3.3 M) were added and stirred under reflux. After 61 hours, the temperature was lowered to room temperature and 0.05 L of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was recrystallized using diethyl ether, hexane and methanol, and silica gel column chromatography (dichloromethane: n-Hexane = 1: 5) afforded 109 compound (1.8 g, 21%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.18-7.22 (m, 6H), 7.34-7.46 (m, 14H), 7.54-7.56 (d, 2H), 7.61-7.65 (m, 4H ), 7.73-7.76 (d, 2H), 7.85 (d, 2H), 7.90-7.91 (d, 2H)

MS / FAB: 644.39 (found), 644.79 (calculated)

Production Example 5

Preparation of Compound 112

4 compound (16 g, 58 mmol), phenylboronic acid (10.6 g, 87 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (4.11 g, 5.8 mmol), sodium carbonate (31.04 g, 290 mmol) Toluene (300 mL) and distilled water (30 mL) were added and stirred under reflux. After 12 hours, the mixture was extracted with water and dichloromethane and distilled under reduced pressure. Silica gel column chromatography (Ethylacetate: n-Hexane = 1:10) gave 13 compound (7.5 g, 48%) as a white solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.23-7.26 (t, 2H), 7.34-7.38 (t, 3H), 7.50-7.55 (m, 3H), 7.62 (d, 1H), 7.78 (s, 1H), 7.87 (d, 1H), 7.92 (d, 1H)

MS / FAB: 270.64 (found), 270.36 (calculated)

13 Compound (3.4 g, 12 mmol) is dissolved in dichloromethane (0.05 L, 0.24 M) and bromine (1.42 mL, 27 mmol) is diluted dropwise in dichloromethane (50 mL) slowly at 0 ° C. After 2 hours, the temperature was raised to 25 ° C. and stirred for 24 hours. Neutralize with aqueous potassium hydroxide solution and extract with 200 mL of dichloromethane. Distillation under reduced pressure and filtration under reduced pressure with washing with hexane gave 14 compounds (4.78 g, 93%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.66 (s, 6H), 7.38 (d, 2H), 7.48 (d, 2H), 7.57 (d, 1H), 7.61 (d, 1H) , 7.70-7.72 (d, 2H), 7.76 (s, 1H), 7.90 (d, 1H)

MS / FAB: 428.36 (found), 428.15 (calculated)

3 compound (3.48 g, 9.3 mmol), 14 compound (1.66 g, 3.88 mmol) prepared in Preparation Example 1, trans-dichlorobistriphenylphosphinepalladium (II) (0.218 g, 0.31 mmol), sodium carbonate (0.99 g, 9.3 mmol), toluene (20 mL), distilled water (2 mL) were added, and the mixture was stirred under reflux. After 36 hours, the temperature was lowered to room temperature, and 20 mL of distilled water was added to terminate the reaction. Extract with dichloromethane and distillation under reduced pressure. The obtained solid was subjected to silica gel column chromatography (dichloromethane: n-Hexane = 1: 4) to give 112 compound (1.8 g, 50%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.67 (s, 6H), 7.25-7.47 (m, 24H), 7.56-7.66 (m, 12H), 7.76-7.92 (m, 8H)

MS / FAB: 927.01 (found), 927.17 (calculated)

[Manufacture example 6]

Preparation of Compound 113

5 compound (30 g, 85.2 mmol) with phenylboronic acid (22.8 g, 187.44 mmol), tetrakistriphenylphosphinepalladium (0) (4.9 g, 4.26 mmol), sodium carbonate (72 g, 682 mmol), toluene (500 mL) and distilled water (30 mL) were added followed by stirring under reflux. After 12 hours, the mixture was extracted with 200 mL of ethyl acetate and 100 mL of water, and then dried under reduced pressure. Recrystallization with dichloromethane and methanol and silica gel column chromatography (dichloromethane: n-Hexane = 1: 10) to give a 15 compound (14 g, 47%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.20 (t, 2H), 7.34 (t, 4H), 7.50 (d, 4H), 7.62 (d, 2H) , 7.79 (s, 2H), 7.91 (d, 2H)

MS / FAB: 346.97 (found), 346.46 (calculated)

15 Compound (3.2 g, 9.24 mmol) is dissolved in dichloromethane (70 mL) and bromine (0.973 mL, 18.5 mmol) is diluted slowly in dichloromethane (70 mL) at 0 ° C. After 2 hours, the temperature was raised to 25 ° C. and stirred for 24 hours. Neutralize with aqueous potassium hydroxide solution and extract with 260 mL of dichloromethane. Distilled water was added, recrystallized and filtered under reduced pressure while washing with hexane to give 16 compounds (3.91 g, 83%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.67 (s, 6H), 7.36 (d, 4H), 7.48 (d, 4H), 7.61 (d, 2H), 7.76 (s, 2H) , 7.89 (d, 2 H)

MS / FAB: 504.37 (found), 504.25 (calculated)

3 compound (7.24 g, 19.34 mmol) prepared in Preparation Example 1, 16 compound (3.9 g, 7.7 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.43 g, 0.62 mmol), sodium carbonate (2.46 g, 23.2 mmol), toluene (65 mL), distilled water (6.5 mL) were added and stirred under reflux. After 38 hours, the temperature was lowered to room temperature, and 60 mL of distilled water was added to terminate the reaction. Extract with dichloromethane 250 mL and distillation under reduced pressure. Recrystallization using methanol and acetone, and the obtained solid was silica gel column chromatography (dichloromethane: n-Hexane = 1: 4) to give a 113 compound (3.03 g, 39%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.63 (s, 6H), 7.18-7.48 (m, 24H), 7.56-7.59 (m, 12H), 7.69-7.75 (m, 8H), 7.88-7.90 (d, 4H)

MS / FAB: 1003.65 (found), 1003.27 (calculated)

[Manufacture example 7]

Preparation of Compound 201

Tetrahydrofuran (5 L) was added to 2-bromonaphthalene (819 g, 3.96 mol), stirred at room temperature for 10 minutes to completely dissolve, the temperature was lowered to -72 ° C, and n-butyllithium (1.6M in n-hexane ) (2.68 L, 4.285 mol) is slowly added dropwise. After 1 hour, 2-chloroanthraquinone (400 g, 1.648 mol) was added, and then the temperature was slowly raised to room temperature and stirred for 26 hours. Saturated ammonium chloride solution was added, stirred for 1 hour, and filtered under reduced pressure. The organic layer was separated and evaporated to afford 17 compound (551 g, 67%) as a brown solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.17-7.20 (m, 16H), 7.31 (d, 3H), 7.35 (s, 2H)

MS / FAB: 498.13 (found), 498.99 (calculated)

17 compound (551 g, 1.104 mol), potassium iodide (733 g, 4.42 mol), sodium phosphate monohydrate (937 g, 8.8 mol), acetic acid (3.35 L, 0.33 M) were added and stirred under reflux. After 21 hours, the mixture was cooled to room temperature and filtered under reduced pressure. A small amount of potassium carbonate and distilled water were added to the solid obtained after filtration under reduced pressure to make neutral, and after stirring for 2 hours, the organic layer was separated and evaporated to obtain compound 18 (318 g, 62%) as a light green solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.23 (t, 2H), 7.31-7.34 (m, 8H), 7.37 (d, 1H), 7.49 (d, 4H), 7.65 (d, 3H), 7.68 (d, 2H), 7.73 (s, 1H)

MS / FAB: 465.15 (found), 464.98 (calculated)

18 compound (318 g, 0.68 mol) and tetrahydrofuran (2.3 L) were added thereto, stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C. Then n-butyllithium (1.6M in n-hexane) (0.56 L, 0.89 mol) is slowly added dropwise. After 1 hour, triisopropylborate (206 g, 1.09 mol) is added, and the temperature is slowly raised to room temperature and stirred for 24 hours. 2 L of 10% HCl solution was added, stirred for 2 hours, and filtered under reduced pressure. The organic layer was separated and evaporated, and recrystallized with hexane and methanol to obtain compound 19 (188 g, 58%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.21 (t, 2H), 7.27 (d, 1H), 7.30-7.34 (m, 8H), 7.47 (d, 4H), 7.66 (d, 3H), 7.72 (d, 2H), 7.74 (s, 1H)

MS / FAB: 474.11 (found), 474.35 (calculated)

19 compound (11 g, 23.19 mmol), 4 compound (7.6 g, 27.83 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.326 g, 0.464 mmol), sodium carbonate (5.41 g, 51.02 mmol), Toluene (100 mL) and distilled water (10 mL) were added and stirred under reflux. After 30 hours, the temperature was lowered to room temperature, and 100 mL of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was recrystallized using hexane and methanol to obtain 201 compound (8.52 g, 61%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.66 (s, 6H), 7.20 (t, 2H), 7.30-7.47 (m, 14H), 7.51-7.57 (m, 4H), 7.68- 7.71 (m, 3H), 7.77 (s, 2H), 7.84-7.88 (s, 2H), 7.93 (s, 1H)

MS / FAB: 622.62 (found), 622.79 (calculated)

[Manufacture example 8]

Preparation of Compound 301

Tetrahydrofuran (410 mL) was added to 2-bromobiphenyl (48 g, 0.206 mol), stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C. Then, n-butyllithium (1.6M in n-hexane ) (0.14 L, 0.22 mol) is slowly added dropwise. After 1 hour, 2-chloroanthraquinone (20 g, 82 mmol) was added, and then the temperature was slowly raised to room temperature, followed by stirring for 12 hours. 0.5 L of 10% HCl solution was added, stirred for 1 hour, and filtered under reduced pressure. An organic layer was obtained using 240 mL of dichloromethane, and evaporated under reduced pressure, followed by recrystallization using hexane to obtain compound 21 (32.7 g, 72%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.14-7.26 (m, 12H), 7.31-7.40 (m. 9H), 7.46-7.48 (d, 4H)

MS / FAB: 550.62 (found), 551.07 (calculated)

21 compound (32.7 g, 0.06 mol), potassium iodide (39.4 g, 0.24 mol), sodium phosphate monohydrate (50.3 g, 0.48 mol) and acetic acid (0.2 L) were added and stirred under reflux. After 21 hours, the mixture was cooled to room temperature and filtered under reduced pressure. A small amount of potassium carbonate and distilled water were added to the obtained solid after filtration under reduced pressure to make neutral, and after stirring for 2 hours, the organic layer was separated and evaporated to obtain compound 22 (9.13 g, 54%) as a white solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.21-7.26 (m, 6H), 7.33-7.35 (m. 7H), 7.50-7.53 (m, 8H), 7.62 (d, 1H), 7.66-7.68 (t, 3H)

MS / FAB: 517.60 (found), 517.05 (calculated)

22 compound (9.13 g, 17.66 mmol) and tetrahydrofuran (60 mL) were added and stirred at room temperature for 10 minutes to completely dissolve. The temperature was lowered to -72 ° C, and n-butyllithium (1.6M in n-hexane) (14.6 mL, 22.95 mmol) was added slowly dropwise. After 1 hour, triisopropylborate (5.32 g, 28.26 mmol) is added, and then slowly heated to room temperature and stirred for 22 hours. 0.1 L of 10% HCl solution was added, stirred for 1 hour, and filtered under reduced pressure. 150 mL of ethyl acetate was used to obtain an organic layer, and the residue was evaporated under reduced pressure, and then recrystallized with hexane and methanol to obtain compound 23 (3.81 g, 41%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.21-7.25 (m, 6H), 7.33-7.35 (m. 7H), 7.50-7.55 (m, 8H), 7.61 (d, 1H), 7.65-7.69 (t, 3H)

MS / FAB: 525.89 (found), 526.43 (calculated)

23 compound (3.81 g, 7.24 mmol), 4 compound (2.37 g, 8.68 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.26 g, 0.36 mmol), sodium carbonate (1.54 g, 14.48 mmol), Toluene (40 mL) and distilled water (3.6 mL) were added and stirred under reflux. After 46 hours, the temperature was lowered to room temperature, and 40 mL of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was recrystallized using hexane and methanol, and silica gel column chromatography (dichloromethane: n-Hexane = 1: 1) gave 301 compound (1.61 g, 33%) as a white solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.65 (s, 6H), 7.19 (t, 2H), 7.32-7.46 (m, 16H), 7.53-7.57 (m, 6H), 7.67- 7.71 (m, 3H), 7.79 (s, 2H), 7.85-7.88 (s, 2H), 7.92 (s, 1H)

MS / FAB: 674.24 (found), 674.86 (calculated)

[Manufacture example 9]

Preparation of Compound 302

Tetrahydrofuran (620 mL) was added to 1,2-dibromobenzene (70 g, 0.3 mol), stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C. Then, n-butyllithium (1.6 M in n-hexane) (200 mL, 0.321 mol) is added slowly dropwise. After 1 hour, 2-chloroanthraquinone (30 g, 0.12 mol) was added, and then the temperature was slowly raised to room temperature and stirred for 21 hours. 500 mL of 10% HCl solution was added, stirred for 1 hour, and filtered under reduced pressure. An organic layer was obtained using 300 mL of dichloromethane, and evaporated under reduced pressure, and then recrystallized from hexane and methanol to obtain compound No. 24 (44.04 g, 64%).

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.10 (t, 4H), 7.14 (t, 2H), 7.20 (t, 3H), 7.26 (d, 2H), 7.37 (m, 4H)

MS / FAB: 556.33 (found), 556.67 (calculated)

24 compound (44 g, 79.04 mmol), potassium iodide (26.24 g, 158 mmol), sodium phosphate monohydrate (41.9 g, 395 mmol) and acetic acid (0.26 L, 0.3 M) were added and stirred under reflux. After 24 hours, the mixture was cooled to room temperature and filtered under reduced pressure. A small amount of potassium carbonate and distilled water were added to the obtained solid after filtration under reduced pressure to make neutral. After stirring for 2 hours, the organic layer was separated, evaporated, and recrystallized with hexane and methanol to give 25 compounds (20.2 g, 49%) as an apricot solid. Got.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.11 (t, 4H), 7.16 (t, 2H), 7.21 (t, 3H), 7.27 (d, 2H), 7.39 (m, 4H)

MS / FAB: 522.02 (found), 522.65 (calculated)

25 compound (20 g, 38.27 mmol), 4-biphenylboronic acid (21.4 g, 91.84 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.1.34 g, 1.91 mmol), sodium carbonate (12.17 g, 114.8 mmol), toluene (190 mL), distilled water (20 mL) were added, and the mixture was stirred under reflux. After 51 hours, the temperature was lowered to room temperature, and 200 mL of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was recrystallized using hexane and methanol, and silica gel column chromatography (dichloromethane: n-Hexane = 1: 10) afforded compound 26 (13.31 g, 52%) as a yellow solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.22-7.26 (m, 8H), 7.33-7.38 (m. 11H), 7.49-7.54 (m, 10H), 7.62 (d, 1H), 7.66-7.68 (t, 3H)

MS / FAB: 668.75 (found), 669.25 (calculated)

26 compound (13 g, 19.42 mmol) and tetrahydrofuran (100 mL) were added, stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C, and then n-butyllithium (1.6 M in n-hexane) (17 mL, 27.2 mmol) was added slowly dropwise. After 1 hour, triisopropylborate (6.58 g, 34.96 mmol) is added, and then slowly raised to room temperature and stirred for 19 hours. 100 mL of 10% HCl solution was added thereto, stirred for 2 hours, and filtered under reduced pressure. The resulting solid was recrystallized from hexane and methanol to obtain compound 27 (4.74 g, 36%) as a white solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.21-7.26 (m, 8H), 7.32-7.38 (m. 11H), 7.49-7.53 (m, 10H), 7.60 (d, 1H), 7.67-7.70 (t, 3H)

MS / FAB: 678.27 (found), 678.62 (calculated)

5 compound (2.93 g, 8.31 mmol), 27 compound (4.7 g, 6.93 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.34 g, 0.49 mmol), sodium carbonate (1.47 g, 13.86 mmol), Toluene (40 mL) and distilled water (3.5 mL) were added and stirred under reflux. After 25 hours, the temperature was lowered to room temperature, and 50 mL of distilled water was added to terminate the reaction. The solid produced at this time is filtered under reduced pressure. The obtained solid was subjected to silica gel column chromatography (Ethylacetate: n-Hexane = 1: 8) to obtain 28 compound (4.58 g, 73%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.68 (s, 6H), 7.22-7.26 (m, 3H), 7.33-7.41 (m, 19H), 7.50-7.56 (m, 8H), 7.66-7.71 (m, 4H), 7.81 (s, 2H), 7.83-7.85 (s, 2H), 7.90 (s, 1H)

MS / FAB: 904.67 (found), 905.95 (calculated)

28 compound (4.58 g, 5.06 mmol), phenylboronic acid (0.74 g, 6.07 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (0.18 g, 0.25 mmol), sodium carbonate (1.3 g, 12.14 mmol) Toluene (40 mL) and distilled water (3.5 mL) were added and stirred under reflux. After 30 hours, the temperature was lowered to room temperature, and 50 mL of distilled water was added to terminate the reaction. The organic layer was extracted with dichloromethane 300 mL and distilled under reduced pressure. The obtained solid was subjected to silica gel column chromatography (Ethylacetate: n-Hexane = 1: 8), and recrystallized with methanol to obtain 302 compound (2.47 g, 54%) as a white solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.67 (s, 6H), 7.22-7.25 (m, 4H), 7.32-7.40 (m, 21H), 7.49-7.56 (m, 10H), 7.65-7.70 (m, 4H), 7.79 (s, 2H), 7.82-7.84 (s, 2H), 7.89 (s, 1H)

MS / FAB: 903.79 (found), 903.15 (calculated)

[Production Example 10]

Preparation of Compound 401

To 2,6-diaminoanthraquinone (100 g, 0.42 mol) is added cupperbromide (328 g, 1.47 mol) and acetonitrile (1.5 L) and stirred. t-butyl nitrite (173 g, 1.68 mol) is slowly added dropwise. After 1 hour, the mixture is stirred at reflux. After 30 hours, the temperature was lowered to room temperature, and 2 L of 10% HCl solution was added thereto, stirred for 1 hour, and filtered under reduced pressure. Recrystallization from hexane and methanol afforded compound 49 (117 g, 76%) as a light brown solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.68 (d, 2H), 7.73 (d, 2H), 7.96 (s, 2H)

MS / FAB: 365.84 (found), 366.00 (calculated)

Add bromobenzene (51.47 g, 0.328 mol) and tetrahydrofuran (910 mL), stir at room temperature for 10 minutes to dissolve completely, lower the temperature to -72 ° C, and n-butyllithium (1.6 M in n-hexane) ( 221 mL, 0.36 mol) is added slowly dropwise. After 1 hour, compound 49 (50 g, 0.14 mol) was added, and the mixture was slowly heated to room temperature and stirred for 22 hours. 1 L of 10% HCl solution was added, stirred for 2 hours, and filtered under reduced pressure. The organic layer was separated and evaporated to give compound 50 (23.54 g, 33%) as a pink solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.18-7.20 (m, 12H), 7.35 (d, 2H), 7.47 (s, 2H)

MS / FAB: 521.95 (found), 522.22 (calculated)

50 compound (20 g, 38 mmol), potassium iodide (25.43 g, 0.15 mol), sodium phosphate monohydrate (24.36 g, 0.23 mol), acetic acid (128 mL) were added and stirred under reflux. After 15 hours, the mixture was cooled to room temperature and filtered under reduced pressure. A small amount of potassium carbonate and distilled water were added to the solid obtained after the filtration under reduced pressure, and the mixture was neutralized. After stirring for 2 hours, the organic layer was separated and evaporated to obtain a dark brown solid. 10) to give 51 compound (7.85 g, 42%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.18-7.21 (m, 12H), 7.36 (d, 2H), 7.48 (s, 2H)

MS / FAB: 487.99 (found), 488.21 (calculated)

51 compound (7.85 g, 16.08 mmol) and tetrahydrofuran (160 mL) were added and stirred at room temperature for 10 minutes to completely dissolve and the temperature was lowered to -72 ° C, followed by n-butyllithium (1.6 M in n-hexane) (16 mL, 20.9 mmol) was added slowly dropwise. After 1 hour, triisopropylborate (6.05 g, 32.16 mmol) is added, and then slowly heated to room temperature and stirred for 20 hours. 100 mL of 10% HCl solution was added thereto, stirred for 5 hours, and filtered under reduced pressure. An organic layer was obtained using 360 mL of dichloromethane, and evaporated under reduced pressure, and then recrystallized with hexane and diethyl ether to give 52 compound (5.24 g, 78%) as an apricot solid.

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 7.16-7.19 (m, 12H), 7.35 (d, 2H), 7.45 (s, 2H)

MS / FAB: 419.18 (found), 418.05 (calculated)

52 compound (7.0 g, 14.34 mmol), 4 compound (9.4 g, 34.4 mmol), trans-dichlorobistriphenylphosphinepalladium (II) (1.0 g, 1.43 mmol), sodium carbonate (6.08 g, 57.36 mmol), Toluene (150 mL) and distilled water (15 mL) were added and stirred under reflux. After 40 hours, the temperature was lowered to room temperature, and 100 mL of distilled water was added to terminate the reaction. The organic layer was obtained using 360 mL of ethyl acetate, and evaporated under reduced pressure, followed by silica gel column chromatography (dichloromethane: n-Hexane = 1: 2), and recrystallization with hexane and methanol to give 401 compound (2.46 g, 24%). )

¹ H NMR (200 MHz, CDCl ₃ ): δ (ppm) = 1.66 (s, 12H), 7.23 (t, 2H), 7.29-7.33 (m, 8H), 7.49-7.59 (m, 10H), 7.74- 7.78 (d, 4H), 7.85-7.89 (d, 6H)

MS / FAB: 714.13 (found), 714.93 (calculated)

Example 1 Fabrication of OLED Device Using Compound According to the Present Invention

An OLED device having a structure using the light emitting material of the present invention was produced.

First, the transparent electrode ITO thin film (15 Ω / □) obtained from the glass for OLED was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol and used.

    Next, an ITO substrate was placed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) having the structure -TNATA), evacuated until the vacuum in the chamber reached 10-6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

Subsequently, the following structure N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition apparatus, and NPB was applied by applying a current to the cell. A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.

After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. The compound according to the present invention (e.g. Compound 301) was placed in one cell of the vacuum deposition equipment, and the dopant light emitting material having the following structure was put in another cell, and the deposition rate was 100: 1 on the hole transport layer. A 35 nm thick light emitting layer was deposited.

Subsequently, tris (8-hydroxyquinoline)-aluminum (III) (Alq) having a structure of 20 nm thick was deposited as an electron transport layer, and then a compound lithium quinolate (Liq) having a structure of 1 to 2 nm thick was formed as an electron injection layer. After deposition, the Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to produce an OLED.

Each material used in the OLED device was vacuum sublimated and purified under 10-6 torr, respectively, to be used as an OLED light emitting material.

Comparative Example 1 An OLED device was manufactured using a conventional light emitting material.

After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, dinaphthylanthracene (DNA), which is a blue light emitting material, was placed in one cell of the vacuum deposition apparatus, and perylene having the following structure, which was another blue light emitting material, in another cell. After each of them, a light emitting layer having a thickness of 35 nm was deposited on the hole transport layer at a deposition rate of 100: 1.

Subsequently, the electron transport layer and the electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

Example 2 Luminescence Characteristics of the Fabricated OLED Device

The luminous efficiency of the organic light emitting compound according to the present invention prepared in Example 1 and Comparative Example 1 and the conventional light emitting compound containing OLED is measured at 500 cd / m 2 and 2,000 cd / m 2, respectively, and are shown in Table 1 below. . Particularly, in the case of the blue light emitting material, the light emission characteristics in the low luminance region and the luminance applied to the panel are very important, and thus the luminance data is about 2,000 cd / m 2 to reflect this.

TABLE 1

As shown in Table 1, based on the "luminescence efficiency / Y" value showing a tendency similar to the quantum efficiency, a comparative example of the OLED device containing DNA: perylene which is a well-known conventional light emitting material according to the present invention and Comparing OLED devices using organic light emitting compounds as light emitting materials, OLED devices using organic light emitting compounds according to the present invention as light emitting materials showed higher "luminescence efficiency / Y" values.

Therefore, the organic light emitting compound of the present invention can be used as a high efficiency blue light emitting material, and has a great advantage in terms of brightness and power consumption of the conventional full color OLED.

The organic light emitting compound according to the present invention has an advantage of producing an OLED device having a good luminous efficiency and excellent life characteristics of the material and a very good driving life of the device.

Claims (8)

An organic light emitting compound represented by Formula 1 below. [Formula 1]

A and B in the formula are independently of each other a chemical bond or C ₆ -C ₃₀ arylene; Ar ₁ and Ar ₂ are each independently an aryl group of C ₆ -C ₃₀ ; Ar ₃ to Ar ₉ are each independently hydrogen, C ₁ -C ₂₀ straight or branched alkyl or alkoxy group, C ₆ -C ₃₀ aryl or heteroaryl group, halogen group; R ₁ and R ₂ are each independently hydrogen, a straight or branched chain alkyl group of C ₁ -C ₂₀ , or an aryl group of C ₆ -C ₃₀ , or R ₁ and R ₂ are each other an alkylene or fused ring alkylene Combine to form a spiro ring; Ar ₁₀ is hydrogen, a C ₁ -C ₂₀ straight or branched alkyl group, C ₆ -C ₃₀ aryl group or halogen; The arylene group, aryl group, heteroaryl group, alkyl group, alkoxy group may be further substituted with C ₁ -C ₂₀ linear or branched alkyl, aryl group, diarylamino group, halogen group. The method of claim 1, Ar ₁₀ is phenyl, naphthyl, anthryl or florenyl unsubstituted or substituted with one or more selected from C ₁ -C ₂₀ straight or branched chain alkyl, phenyl, naphthyl, florenyl, diarylamino group, halogen group Phosphorus organic light emitting compound. The method of claim 1, An organic light emitting compound represented by Formula 2 below. [Formula 2]

A, B, R ₁ , R ₂ and Ar ₁ to Ar ₉ in Formula 2 are the same as defined in claim ₁ ; Ar ₁₁ and Ar ₁₂ are each independently an aryl group of C ₆ -C ₃₀ ; Ar ₁₃ to Ar ₁₉ are each independently hydrogen, C ₁ -C ₂₀ straight or branched chain alkyl or alkoxy group, C ₆ -C ₃₀ aryl or heteroaryl group, halogen group; The aryl group, heteroaryl group, and alkyl group may be further substituted with C ₁ -C ₂₀ linear or branched alkyl, diarylamino group, halogen group. The method of claim 1, R ₁ and R ₂ are each independently hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, An organic light emitting compound, characterized in that it is selected from phenyl, tolyl, biphenyl, benzyl, naphthyl, anthryl and florenyl. The method of claim 3, wherein Wherein Ar ₁ , Ar ₂ , Ar ₁₁ and Ar ₁₂ are independently selected from phenyl, tolyl, biphenyl, benzyl, naphthyl, anthryl and florenyl. The method of claim 1, An organic light emitting compound selected from Chemical Formulas 3 and 4 below. [Formula 3]

[Formula 4]

In Formulas 3 and 4, R ₁ , R ₂ and Ar ₁₀ are the same as defined in claim 1; A and B are independently of one another a chemical bond or 1,4-phenylene, 1,3-phenylene, 1,4-naphthylene, 1,5-naphthylene or 2,6-naphthylene; Ar ₁ , Ar ₂ , Ar ₁₁ and Ar ₁₂ independently of one another are phenyl, 4-tolyl, 3-tolyl, 2-tolyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, (3,5-di Phenyl) phenyl, 9,9-dimethyl-floren-2-yl, 9,9-diphenyl-floren-2-yl, (9,9- (4-methylphenyl) -floren-2-yl, 1 -Naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 3-anthryl, 2-spiroprene. The method of claim 6, An organic light emitting compound, characterized in that selected from the following formula.

An organic light emitting device comprising the organic light emitting compound according to any one of claims 1 to 7.