KR100857025B1 - Blue Electroluminescent Compounds with High Efficiency and Display Device using The Same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by Formula 1 and a display device including the same.

[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 substituted or substituted with one or more selected from hydrogen, C ₁ -C ₂₀ linear or branched alkyl or alkoxy groups, C ₆ -C ₃₀ aryl or heteroaryl groups, halogen groups Phenyl, naphthyl, anthryl or fluorenyl, except that Ar ₁ and Ar ₂ are simultaneously hydrogen

Luminescent, Triphenylene, Organic Luminescent, Antryl

Description

Blue electroluminescent compounds with high efficiency and display device using the same

The present invention relates to a novel organic light emitting compound and a display element employing the same as a light emitting material.

In order to realize a full color OLED display, three kinds of RGB light emitting materials are used, and development of high efficiency long life RGB light emitting materials is an important task to improve the characteristics of the entire organic EL. 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, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials. In this respect, the development of host materials is one of the most important factors to be solved. At this time, the desirable properties of the host material serving as a solvent and energy transporter in the solid state should be high in purity and have an appropriate 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.

Conventional host materials include diphenylvinyl-biphenyl (DPVBi) of Idemitsu-high acid and Dinaphthyl-anthracene (DNA) of Kodak, but there is much room for improvement in terms of efficiency, lifetime and color purity.

In order to develop high-efficiency and long-lasting host materials, disspiro-prolene-anthracene (TBSA), ter-spirofluorene (TSF), and bitriphenylene (BTP) with various skeletons have been developed. It was not a satisfactory level.

In the case of TBSA published by Gyeongsang National University and Samsung SDI (Kwon, SK et.al. Advanced Materials, 2001, 13, 1690; JP 2002121547), luminous efficiency of 3 cd / A at 7.7 V and (0.15, 0.11) Although it showed relatively good color coordinates, it is known to be insufficient in commercialization level. TSF (Wu, C.-C., et. Al. Advanced Materials, 2004, 16, 61; U.S. Patent No. US 2005040392) published by Taiwan National Taiwan showed a relatively good external quantum efficiency of 5.3%, but also at the commercialization level. Insufficient In addition, BTP published by Tsinghua National University of Taiwan (Cheng, C.-H, et.al. Advanced Materials, 2002, 14, 1409; U.S. Patent US 2004076852) and the luminous efficiency of 2.76 cd / A (0.16, 0.14) showed relatively good color coordinates, but it was not enough for commercialization.

SUMMARY OF THE INVENTION 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 a display element containing the organic light emitting compound.

The present invention relates to an organic light emitting compound represented by Formula 1 and a display device including the same.

[Formula 1]

A and B in the formula are independently of each other a chemical bond or C ₆ -C ₃₀ arylene; R ₁ to R ₇ are independently of each other hydrogen, a C ₁ -C ₂₀ linear or branched alkyl group, or C ₆ -C ₃₀ aryl group, or R ₁ to R ₇ are adjacent to each other R ₁ to R ₇ and alkyl Can be combined with the rene to form a fused ring; Ar ₁ and Ar ₂ are independently of each other hydrogen, phenyl, naphthyl, anthryl or fluorenyl, wherein the phenyl, naphthyl, anthryl or fluorenyl is a C ₁ -C ₂₀ straight or branched alkyl group or At least one selected from an alkoxy group, a C ₆ -C ₃₀ aryl or heteroaryl group, a halogen group may be substituted, except that Ar ₁ and Ar ₂ are hydrogen at the same time;

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, halogen group.

A and B are each independently a chemical bond or the following compounds. In the chemical formula of the present invention, a state in which elements are not present in A and B and simply connected to Ar ₁ and Ar ₂ is referred to as a 'chemical bond'.

In addition, Ar ₁ and Ar ₂ are each independently an anthryl compound having the following structure.

Ar ₁₁ 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, alkyl group, alkoxy group may be further substituted with C ₁ -C ₂₀ linear or branched alkyl, aryl, halogen group.

R ₁ to R ₇ of the compound of Formula 1 are independently of each other hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl , Hexadecyl, cyclopentyl, cyclohexyl, phenyl, tolyl, biphenyl, benzyl, naphthyl, anthryl and fluorenyl.

The compound of formula 1 according to the present invention includes a compound of formula 2 to formula 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, A and B are the same as defined in claim 1, Ar ₁ , Ar ₁₁ and Ar ₁₂ are independently of each other phenyl, 4-tolyl, 3-tolyl, 2-tolyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, (3,5-diphenyl) phenyl, 9,9-dimethyl-fluoren-2-yl, 9,9-diphenyl-fluoren-2-yl, (9, 9- (4-methylphenyl) -fluorene) -2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 3-anthryl, 2-spirofluorenyl .

The organic light emitting compound of Formula 2 to Formula 5 may be specifically exemplified as a compound having the following structure.

Preparation Example 1 Preparation of Compound 116 (TPN-1)

Preparation of Compound 112

7.1 g (45.0 mmol) of 1-bromobenzene was dissolved in 100 mL of tetrahydrofuran under a stream of nitrogen, followed by 27.0 mL (n-BuLi, 2.5 M in n-Hexane) of 27.0 mL (67.5 mmol). ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was complete, the reaction mixture was slowly dissolved at 25 ° C. under a reaction mixture of 4.3 g (15.0 mmol) of Compound 111 , 2-Bromoanthraquinone, in 50 mL of tetrahydrofuran under a stream of nitrogen. It was added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 50 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 100 mL of ethyl acetate, dried over anhydrous magnesium sulfate, the organic layer was removed under reduced pressure, and then recrystallized from 100 mL of dichloromethane to give compound 112. 5.7 g (12.9 mmol) were obtained.

Preparation of Compound 113

Compound 112 5.7 g (12.9 mmol), 8.5 g (51.4 mmol) of potassium iodine, 8.2 g (77.2 mmol) of sodium hydrophosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, 50 mL of glacial acetic acid solution was added thereto, and the mixture was stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C., 400 mL of distilled water was added, and the resulting solid was filtered and washed with excess water. Compound 113 was washed with 100 mL of sodium hydroxide aqueous solution and recrystallized with 300 mL of n-hexane. 4.2 g (10.3 mmol) were obtained.

Preparation of Compound 115

5.0 g (16.2 mmol) of compound 114 phosphorous 1-bromotriphenylene was dissolved in 100 mL of tetrahydrofuran under a stream of nitrogen, followed by n-butyllithium (n-BuLi, 2.5 M in n-Hexane). 9.7 mL (24.3 mmol) was slowly added dropwise at -78 ° C, followed by stirring for 1 hour. After 1 hour 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane (2-Isopropoxy -4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 9.0 g (48.6 mmol) was added at -78 ° C and stirred at 25 ° C for 2 hours. Washed with 100 mL of water, and then extracted with ethyl acetate, dry 100 mL and dried over anhydrous magnesium sulfate under reduced pressure and the organic layer dried by filtration the solid obtained was recrystallized with methanol to 50 mL Compound 115 4.7 g (10.0 mmol) was obtained.

Preparation of Compound 116

Compound 113 Into a reaction vessel of 4.2 g (30.0 mmol) and 4.7 g (10.0 mmol) of the compound 115 phosphorus ester compound, 1.2 g (1.0 mmol) of tetrakispalladiumtriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added, followed by toluene 80 It was dissolved in mL. 0.5 g (1.0 mmol) of aliquat 336 was added thereto, and 24 mL of 2 M calcium carbonate solution was added thereto, followed by stirring at reflux at 130 ° C. for 4 hours. At this time, 200 mL of methanol was poured into the precipitate formed to form a solid. The resulting mixture was dissolved in 300 mL of chloroform, filtered, and the organic layer was dried under reduced pressure. Final compound 116 (TPN-1) by recrystallization with 30 mL of tetrahydrofuran. 2.2 g (38% overall yield) were obtained.

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.22-7.32 (m, 8H), 7.48-7.54 (m. 5H), 7.67-7.89 (t, 8H), 8.10-8.12 (m, 3H), 8.34 ( d, 1H), 8.93-8.99 (m, 3H)

MS / FAB: 556.22 (found), 556.69 (calculated)

Preparation Example 2 Preparation of Compound 121 (NTPN)

Preparation of Compound 112

8.3 g (53.1 mmol) of 1-bromobenzene was dissolved in 100 mL of tetrahydrofuran under a stream of nitrogen, followed by 29.5 mL (73.7 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane). ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was complete, the reaction mixture was stirred at 25 ° C. in a reaction mixture obtained by dissolving 5.0 g (17.4 mmol) of Compound 111 , 2-Bromoanthraquinone, in 100 mL of tetrahydrofuran under a nitrogen stream at −78 ° C. Slowly added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 500 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 500 mL of ethyl acetate, dried over anhydrous magnesium sulfate, and the organic layer was dried under reduced pressure. The obtained compound was recrystallized from 300 mL of dichloromethane to give 6.7 g (15 mmol) of the compound 112 .

Preparation of Compound 113

112 g (15 mmol) of Compound 112, 9.7 g (60 mmol) of potassium iodo and 9.5 g (90 mmol) of sodium hydropotassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, 50 mL of glacial acetic acid was added thereto, and the mixture was stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C. and 100 mL of distilled water was added to form a solid, which was filtered and washed with excess water. It was washed with 200 mL of sodium hydroxide aqueous solution and recrystallized with 200 mL of hexane to obtain 5.0 g (12.2 mmol) of Compound 113 .

Preparation of Compound 118

10.6 g (34.5 mmol) of 1-bromotriphenylene, a compound 117 , was dissolved in 280 mL of tetrahydrofuran under a nitrogen stream, followed by n-butyllithium (n-BuLi, 2.5 M in n-Hexane). 17.9 mL (44.9 mmol) was slowly added dropwise at -78 ° C, and stirred for 1 hour. After 1 hour, trimethyl borate 7.2 g (69 mmol) was added under low temperature, and stirred while slowly raising the temperature to 25 ° C. After stirring for 16 hours, 30 mL of 10 M hydrochloric acid is slowly added. After stirring for 1 hour, 200 mL of ethyl acetate was extracted, washed with 200 mL of water, dried over anhydrous magnesium sulfate, and the organic layer was dried under reduced pressure. The obtained solid was recrystallized with 100 mL of hexane, and the solid obtained by filtration was dried under reduced pressure to obtain 9.0 g (33.0 mmol) of Compound 118 .

Preparation of Compound 119

Compound 118 9.2 g (33.9 mmol), 8.8 g (30.8 mmol) of 1,4-dibromonaphthalene, and 2.1 g (3.1 mmol) of trans-dichlorobistriphenylphosphinepalladium (II) (Pd (PPh ₃ ) ₂ Cl ₂ ) After dissolving in 300 mL of toluene, 150 mL of 2 M sodium carbonate was added thereto, followed by heating at 100 ° C. for 3 hours. Extracted with 300 mL of dichloromethane, washed with 300 mL of sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, filtered and dried the organic layer under reduced pressure. The obtained solid was recrystallized with 100 mL of tetrahydrofuran to give 7.7 g (17.7 mmol) of the desired compound 119 .

Preparation of Compound 120

Compound 119 7.7 g (17.7 mmol) was dissolved in 200 mL of tetrahydrofuran under a stream of nitrogen, and 10.6 mL (26.6 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane) was slowly added dropwise at -78 ° C. Stirred for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 6.6 g (35.4 mmol) was added thereto, and the mixture was stirred while raising the temperature to 25 ° C. Extracted with 300 mL of ethyl acetate, washed with 300 mL of water, dried over anhydrous magnesium sulfate and dried under reduced pressure. The obtained solid was recrystallized from 150 mL of methanol and the solid obtained by filtration was dried to give 7.6 g (15.9 mmol) of Compound 120 .

Preparation of Compound 121

Compound 113 5.0 g (12.2 mmol) and 7.6 g (15.9 mmol) of Compound 120 ester compound were added to the reaction vessel, and 1.4 g (1.2 mmol) of tetrakispalladiumtriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added, followed by 100 mL. Dissolved in toluene. 0.6 g (1.2 mmol) of aliquat 336 was added thereto, 30 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred at reflux for 130 ° C. for 4 hours. Excess methanol is poured into the precipitate formed to form a solid. The resulting solution is dissolved in 300 mL of chloroform, filtered, and the solvent is removed under reduced pressure. Final compound 121 (NTPN) by recrystallization from 300 mL of tetrahydrofuran 3.5 g (42% overall yield) were obtained.

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.22-7.32 (m, 10H), 7.48-7.67 (m. 12H), 8.10-8.12 (m, 3H), 8.34 (dd, 1H), 8.93-8.99 ( m, 3H)

MS / FAB: 682.27 (found), 682.85 (calculated)

Preparation Example 3 Preparation of Compound 126 (BPTPN)

Preparation of Compound 112

8.2 g (52.2 mole) of 1-bromobenzene was dissolved in 150 mL of tetrahydrofuran under nitrogen atmosphere, and then 31.3 mL (n.-BuLi, 2.5 M in n-Hexane) (78.3 mmol) ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was complete, the reaction mixture was slowly dissolved at -78 ° C in a reaction mixture obtained by dissolving 5 g (17.4 mmol) of Compound 111 , 2-Bromoanthraquinone, in 50 mL of tetrahydrofuran under a stream of nitrogen at 25 ° C. It was added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 500 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 500 mL of ethyl acetate, dried over anhydrous magnesium sulfate, and the organic layer was dried under reduced pressure. The resulting solid was recrystallized from 300 mL of dichloromethane to give 6.6 g (14 mmol) of compound 112 .

Preparation of Compound 113

112 g (14 mmol) of Compound 112, 9.3 g (56 mmol) of potassium iodo and 8.9 g (84 mmol) of sodium hydropotassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, 40 mL of glacial acetic acid was added thereto, and the mixture was stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C. and 100 mL of distilled water was added to form a solid, which was filtered and washed with excess water. Again washed with 200 mL of sodium hydroxide aqueous solution and recrystallized with 200 mL of hexane to give compound 113 5.3 g (12.9 mmol) were obtained.

Preparation of Compound 122

Compound 113 4.9 g (12 mmol) and 2.7 g (13.2 mmol) of 4-bromophenylboronic acid were added 0.9 g (1.2 mmol) of trans-dichlorobistriphenylphosphinepalladium (II) (Pd (PPh ₃ ) ₂ Cl ₂ ). ) And dissolve in 120 mL of toluene. While stirring, 60 mL of 2 M aqueous sodium carbonate solution was added thereto, followed by stirring at reflux at 120 ° C. After 3 hours of reaction, the mixture was extracted with 200 mL of dichloromethane, washed with 200 mL of sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the organic layer was dried under reduced pressure. The obtained solid was recrystallized from 100 mL of tetrahydrofuran to give 5.0 g (10.3 mmol) of the compound 122 .

Preparation of Compound 124

5.8 g (19 mmol) of 1-bromotriphenylene which is Compound 123 and 4.2 g (20.9 mmol) of 4-bromophenylboronic acid were added to trans-dichlorobistriphenylphosphinepalladium (II) (Pd). 1.3 g (1.9 mmol) of (PPh ₃ ) ₂ Cl ₂ ) were added and dissolved in 200 mL of toluene. While stirring, 100 mL of a 2 M aqueous sodium carbonate solution was added thereto, followed by stirring at reflux at 120 ° C. After 3 hours of reaction, the mixture was extracted with 200 mL of dichloromethane, washed with 200 mL of sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, filtered and the organic layer was dried under reduced pressure. The obtained solid compound was recrystallized from 100 mL of tetrahydrofuran to obtain 5.8 g (15 mmol) of the compound 124 .

Preparation of Compound 125

5.8 g (15 mmol) of Compound 124 was dissolved in 150 mL of tetrahydrofuran under a stream of nitrogen, and then 9 mL (22.5 mol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane) was slowly added dropwise at -78 ° C. After stirring for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 5.6 g (30 mmol) was added thereto, and the mixture was stirred while slowly raising the temperature to 25 ° C. Extracted with 300 mL of ethyl acetate, washed with 300 mL of water, dried over anhydrous magnesium sulfate, filtered and the organic layer was dried under reduced pressure. The resulting solid compound was recrystallized from 200 mL of methanol and filtered to dry the obtained compound to give 6.0 g (13.9 mmol) of Compound 125 .

Preparation of Compound 126

Compound 122 5 g (10.3 mmol) and Compound 125 ester compound 5.8 g (13.4 mmol) were added to a reaction vessel, and tetrakispalladiumtriphenylphosphine (Pd (PPh ₃ ) ₄ ) 1.2 g (1.0 mmol) was added thereto, followed by 100 mL. Dissolved in toluene. 0.5 g (1.03 mmol) of aliquat 336 was added thereto, 30 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred at reflux for 120 hours for 6 hours. At this time, 300 mL of excess methanol was poured into the formed precipitate to form a solid, and the resultant was dissolved in 500 mL of chloroform, filtered, and the solvent was dried under reduced pressure. Recrystallized from 200 mL of tetrahydrofuran to give final compound 126 (BPTPN). 2.5 g (34% overall yield) were obtained.

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.22-7.32 (m, 8H), 7.48-7.54 (m. 13H), 7.67-7.73 (m, 3H), 7.82-7.89 (m, 5H), 8.03- 8.05 (m, 1H), 8.10-8.18 (m, 3H), 8.93-8.95 (dd, 2H), 9.15 (dd, 1H)

MS / FAB: 708.28 (found), 708.89 (calculated)

Preparation Example 4 Preparation of Compound 129 (BATPN-1)

Preparation of Compound 112

19.4 g (123.6 mmol) of 1-bromobenzene was dissolved in 250 mL of tetrahydrofuran under a stream of nitrogen, followed by 74.16 mL (185.4 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane). ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was complete, the reaction mixture was slowly dissolved at 25 ° C. under a reaction mixture of 11.8 g (41.2 mmol) of compound 111 , 2-Bromoanthraquinone, dissolved in 200 mL of tetrahydrofuran under a nitrogen atmosphere. It was added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 400 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 400 mL of ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The organic layer was dried under a reduced pressure to obtain a solid compound. The obtained compound was recrystallized from 200 mL of dichloromethane to give 15.5 g (35 mmol) of compound 112 .

Preparation of Compound 113

1112 g (35.0 mmol) of Compound 112, 23.2 g (140.0 mmol) of iodopotassium, and 22.3 g (210.0 mmol) of sodium hydropotassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, dissolved in 90 mL of glacial acetic acid, and stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C. and 200 mmL of distilled water was added to form a solid, which was filtered and washed with excess 300 mL of water. Again washed with 200 mL of sodium hydroxide aqueous solution and recrystallized with 200 mL of hexane to give 13.0 g (31.8 mmol) of Compound 113 .

Preparation of Compound 128

4.6 g (12.0 mmol) of 1,8-dibromotriphenylene, which is a compound 127 , was dissolved in 120 mL of tetrahydrofuran under a nitrogen stream, and then n-butyllithium (n-BuLi, 2.5 M in n-Hexane) 14.4 mL (35.9 mmol) was slowly added dropwise at -78 ° C, and stirred for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 23.4 g (47.9 mmol) was added under a low temperature and stirred while slowly raising the temperature to 25 ℃. The mixture was washed with 300 mL of water, extracted with 300 mL of ethyl acetate, dried over anhydrous magnesium sulfate, and the organic layer was removed under reduced pressure. The obtained compound was recrystallized from 150 mL of methanol and the solid was filtered to give 5.0 g (10.4 mmol) of Compound 128 .

Preparation of Compound 129

1113 g (33.0 mmol) of Compound 113 and 5 g (11 mmol) of Compound 128 ester were placed in a reaction vessel, and 1.2 g (1.1 mmol) of tetrakispalladiumtriphenylphosphinethiriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added. Was added and then dissolved in 100 mL of toluene. 0.5 g (1.1 mmol) of aliquat 336 was added thereto, 30 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux at 130 ° C. for 4 hours. Excess methanol was poured into the precipitate formed to form a solid, which was dissolved in 300 mL of chloroform and filtered to remove the solvent. Final compound 129 (BATPN-1) by recrystallization from 200 mL of tetrahydrofuran 3.3 g (36% overall yield) were obtained.

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.22-7.32 (m, 16H), 7.48-7.54 (m. 10H), 7.67-7.73 (m, 6H), 7.85-7.88 (m, 4H), 8.04- 8.09 (t, 2H), 8.52-8.88 (m, 4H), 8.74 (s, 2H)

MS / FAB: 884.34 (found), 885.10 (calculated)

Preparation Example 5 Preparation of Compound 132 (BATPN-2)

Preparation of Compound 130

27.3 g (132 mmol) of 2-Bromonaphthalene was dissolved in 250 mL of tetrahydrofuran under a stream of nitrogen, followed by 79.2 mL (198 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane). ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was complete, the reaction mixture was slowly stirred at -25 ° C in a reaction mixture obtained by dissolving 12.6 g (44 mmol) of compound 111 , 2-Bromoanthraquinone, in 200 mL of tetrahydrofuran under nitrogen stream. It was added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 200 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction, the mixture was extracted with 200 mL of ethyl acetate, dried over anhydrous magnesium sulfate, the organic layer was dried under reduced pressure, and recrystallized with 200 mL of dichloromethane to obtain Compound 130 (20.0 g, 36.8 mmol).

Preparation of Compound 131

Compound 130 19.2 g (35.3 mmol), 23.4 g (141.2 mmol) of iodopotassium and 22.5 g (211.8 mmol) of sodium hydropotassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, dissolved in 100 mL of glacial acetic acid, and stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C., and distilled water was added. A solid was formed, which was filtered and washed with excess water. Again washed with 300 mL of sodium hydroxide aqueous solution and recrystallized with 200 mL of hexane to give 16.0 g (31.4 mmol) of Compound 131 .

Preparation of Compound 128

4.6 g (12 mmol) of 1,8-dibromotriphenylene, which is a compound 127 , was dissolved in 120 mL of tetrahydrofuran under a nitrogen stream, and then n-butyllithium (n-BuLi, 2.5 M in n-Hexane) 14.4 mL (35.9 mmol) was slowly added dropwise at -78 ° C, and stirred for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 23.4 g (47.9 mmol) was added under a low temperature and stirred while slowly raising to 25 ℃. The mixture was washed with 500 mL of water, extracted with 500 mL of ethyl acetate, dried over anhydrous magnesium sulfate, filtered and the organic layer was removed under reduced pressure. The obtained compound was recrystallized from 300 mL of methanol, and the obtained solid was filtered to obtain 5.0 g (10.4 mmol) of Compound 128 .

Preparation of Compound 132

Compound 131 16 g (30.9 mmol) and 5.0 g (10.3 mmol) of Compound 128 ester compound were placed in a reaction vessel, and 1.2 g (1.0 mmol) of tetrakispalladiumtriphenylphosphinethyriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added thereto. Then dissolved in 100 mL of toluene. 0.5 g (1.0 mmol) of aliquat 336 was added thereto, 30 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux for 5 hours. At this time, 300 mL of excess methanol was poured into the formed precipitate to form a solid, and the resultant was filtered with 500 mL of chloroform, and then the solvent was removed under reduced pressure. Final compound 132 (TPN-3) by recrystallization from 200 mL of tetrahydrofuran. 3.6 g (38.9% overall yield) were obtained.

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.30-7.32 (m, 12H), 7.54-7.70 (m, 24H), 7.85-7.89 (m, 8H), 8.04-8.08 (t, 2H), 8.54- 8.70 (m, 6H)

MS / FAB: 1084.41 (found), 1085.33 (calculated)

Preparation Example 6 Preparation of Compound 135 (TPN-3)

Preparation of Compound 133

21 g (90 mmol) of 4-bromobiphenyl was dissolved in 200 mL of tetrahydrofuran under a stream of nitrogen, followed by 54 mL (135 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane). ) Was slowly added dropwise at -78 ° C and stirred for 2 hours. After stirring was completed, the reaction mixture was slowly added dropwise at -78 ° C to a reaction mixture of 8.7 g (30 mmol) of Compound 111 , 2-Bromoanthraquinone, dissolved in 100 mL of tetrahydrofuran under a nitrogen stream at 25 ° C. It was. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. 300 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 300 mL of ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the organic layer was removed under reduced pressure and recrystallized from 200 mL of dichloromethane to give 14.8 g (24.9 mmol) of Compound 133 . Got.

Preparation of Compound 134

10 g (16.8 mmol) g of Compound 133, 11.16 g (67.2 mmol) of potassium iodide, and 10.7 g (100.8 mmol) of sodium hydropotassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, and 100 mL of glacial acetic acid was added thereto, followed by stirring under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C., and distilled water was added. A solid was formed, which was filtered and washed with excess water. Again washed with 300 mL of sodium hydroxide aqueous solution and recrystallized with 20 mL of hexane to give 8.5 g (15.5 mmol) of the compound 134 .

Preparation of Compound 115

5.0 g (16.2 mmol) of compound 114 phosphorus 1-bromotriphenylene was dissolved in 160 mL of tetrahydrofuran under a nitrogen atmosphere, followed by n-butyllithium (n-BuLi, 2.5 M in n-Hexane). 9.7 mL (21.0 mmol) was slowly added dropwise at -78 ° C, and stirred for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 6.0 g (32.4 mmol) was added under low temperature and stirred while slowly raising the temperature to 25 ℃. Extracted with 300 mL of ethyl acetate, washed with 300 mL of water, dried over anhydrous magnesium sulfate, filtered and dried the organic layer under reduced pressure. Recrystallized with 200 mL of methanol and filtered to dry solid to give 5.0 g (14.1 mmol) of Compound 115 .

Preparation of Compound 135

compound134  5.0 g (8.9 mmol) and compound115  4.7 g (13.4 mmol) of the ester compound were placed in a reaction vessel, and tetrakispalladiumtriphenylphosphinethiriphenylphosphine (Pd (PPh₃)₄) 1.0 g (0.9 mmol) was added and then dissolved in 80 mL of toluene. 0.4 g (0.9 mmol) of aliquat 336 was added thereto, and 24 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux at 130 ° C. for 3 hours. At this time, 200 mL of excess methanol was poured into the precipitate formed to form a solid, which was dissolved in 500 mL of chloroform, filtered, and the solvent was removed under reduced pressure. Final compound recrystallized from 200 mL of tetrahydrofuran1352.0 g (32% overall yield) of (TPN-3) was obtained.

1 H NMR (200 MHz, CDCl ₃ ) δ = 7.20-7.22 (m, 2H), 7.29-7.32 (m. 6H), 7.48-7.54 (m, 13H), 7.55-7.58 (m, 3H), 7.82-7.88 (m, 5H), 8.10-8.12 (m, 3H), 8.34 (dd, 1H), 8.93-8.99 (m, 3H)

MS / FAB: 708.28 (found), 708.89 (calculated)

Preparation Example 7 Preparation of Compound 140 (TPN-4)

Preparation of Compound 137

15.0 g (60.0 mmol) of 2-bromofluorene, which is Compound 136 , and 26.7 g (480.0 mmol) of potassium hydroxide were added to 300 mL of methyl sulfoxide and stirred. 45 mL of distilled water was added thereto, and 33.9 g (120 mmol) of iodomethane (CH ₃ I) was added dropwise. After stirring 20 minutes further, the mixture was stirred at 25 ° C. for 20 hours, and 500 mL of water was added to terminate the reaction. The mixture was extracted with 500 mL of dichloromethane, dried over anhydrous magnesium sulfate, and dried under reduced pressure. The obtained compound was columned (hexane) and dried to give 15.2 g (55.6 mmol) of the compound 137 .

Preparation of Compound 138

14.3 g (52.2 mmol) of Compound 137 was dissolved in 150 mL of tetrahydrofuran under a nitrogen atmosphere, and then 31.3 mL (78.3 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane) was slowly added dropwise at -78 ° C. After stirring for 2 hours. After stirring was complete, the reaction mixture was slowly dissolved at 25 ° C. in a reaction mixture obtained by dissolving 5.0 g (17.4 mmol) of Compound 111 , 2-Bromoanthraquinone, in 50 mL of tetrahydrofuran under a nitrogen stream. Added dropwise. After slowly raising the temperature from -78 ℃ to 25 ℃ and stirred for 12 hours. After completion of the reaction, 200 mL of saturated aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with 200 mL of ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the organic layer was removed under reduced pressure and recrystallized with 200 mL of hexane to give 138 g of compound 138 (14.6 mmol). Got.

Preparation of Compound 139

138 g (14.6 mmol) of compound 138, 9.7 g (58.4 mmol) of potassium iodide, and 9.3 g (87.7 mmol) of sodium high drop potassium phosphate hydrate (NaHPO ₂ H ₂ O) were added thereto, dissolved in 30 mL of glacial acetic acid, and stirred under reflux. After stirring for 18 hours, the temperature was lowered to 25 ° C. and distilled water was added. A solid was formed, which was filtered and washed with excess water. Again washed with 200 mL of sodium hydroxide aqueous solution and recrystallized with 200 mL of dichloromethane and 200 mL of hexane to give 8.5 g (13.3 mmol) of 139 .

Preparation of Compound 115

7.0 g (22.8 mmol) of 1-bromotriphenylene which is Compound 114 was dissolved in 200 mL of tetrahydrofuran under a nitrogen stream, and then n-butyllithium (n-BuLi, 2.5 M in n-Hexane) was added. 13.6 mL (34.1 mmol) was slowly added dropwise at -78 ° C, and stirred for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 8.5 g (45.5 mmol) was added under low temperature and stirred while slowly raising the temperature to 25 ℃. Washed with 300 mL of water, extracted with 300 mL of ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the organic layer was removed under reduced pressure, and the solid obtained by recrystallization with 200 mL of methanol was filtered and compound 115 7.0 g (19.9 mmol) were obtained.

Preparation of Compound 140

Compound 139 8.5 g (13.3 mmol) and 7.0 g (19.9 mmol) of Compound 115 ester compound were placed in a reaction vessel, and 1.5 g (1.3 mmol) of tetrakispalladiumtriphenylphosphinethyriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added thereto. And then dissolved in 150 mL of toluene. 0.3 g (1.3 mmol) of aliquat 336 was added thereto, 45 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux at 130 ° C. for 5 hours. Excess methanol was poured into the precipitate formed to form a solid, which was dissolved in 500 mL of chloroform and filtered, and then the solvent was removed under reduced pressure. Recrystallization with 200 mL of tetrahydrofuran gave 4.1 g (39% overall yield) of final compound 140 (TPN-4).

¹ H NMR (200 MHz, CDCl ₃ ) δ = 1.67 (s, 12H), 7.28-7.36 (m, 6H), 7.84 (m, 19H), 8.10-8.12 (m, 3H), 8.34-8.36 (m, 1H), 8.93-8.99 (m, 3H)

MS / FAB: 788.34 (found), 789.01 (calculated)

Preparation Example 8 Preparation of Compound 144 (BATPN-3)

Preparation of Compound 142

15.0 g (58.3 mmol) of 9-Bromoanthracene, compound 141 , 8.5 g (70.00 mmol) of phenylboronic acid, tetrakispalladiumtriphenylphosphinethiriphenylphosphine (Pd (PPh _{3) 4} ) 6.7 g (5.8 mmol) was dissolved in 300 mL of toluene and 150 mL of ethanol, and then 486 mL of a 2 M aqueous sodium carbonate solution was stirred under reflux for 5 hours at 120 ° C. After stirring, the temperature was lowered to 25 ° C. and 500 mL of distilled water. The reaction was terminated and the reaction mixture was extracted with 500 mL of ethyl acetate, and the obtained organic layer was dried over anhydrous magnesium sulfate and filtered, and the obtained organic layer was concentrated under reduced pressure and recrystallized with 200 mL of tetrahydrofuran to give 12 g (47.2 mmol) of Compound 142 . Got.

Preparation of Compound 143

11.7 g (46.0 mmol) of Compound 142 and 9.0 g (50.6 mmol) of N-Bromosuccinimide were dissolved in 360 mL of dichloromethane under a nitrogen stream, and then stirred at 25 ° C. for 5 hours. Then, 400 mL of distilled water was added to terminate the reaction, and extracted with 400 mL of dichloromethane. The organic layer obtained herein was dried over magnesium sulfate, filtered and concentrated under reduced pressure, and then recrystallized with 200 mL of tetrahydrofuran to give 143 13.0 g (39 mmol) were obtained.

Preparation of Compound 144

Compound 143 10.4 g (31.2 mmol) and 5.0 g (10.4 mmol) of Compound 128 ester were placed in a reaction vessel, and 1.2 g (1.0 mmol) of tetrakispalladiumtriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added, followed by 100 mL. Dissolved in toluene. 0.5 g (1.0 mmol) of aliquat 336 was added thereto, 30 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux at 130 ° C. for 5 hours. Excess methanol was poured into the precipitate formed to form a solid, dissolved in 300 mL of chloroform, filtered, and the solvent was removed under reduced pressure. Recrystallization with 200 mL of tetrahydrofuran gave 3.1 g (40% overall yield) of final compound 144 (BATPN-3).

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.20-7.32 (m, 14H), 7.48 (t. 4H), 7.67 (d, 8H), 7.84 (d, 2H), 8.04 (d, 2H), 8.49 -8.55 (m, 4H), 8.70 (d, 2H)

MS / FAB: 732.28 (found), 732.91 (calculated)

Preparation Example 9 Preparation of Compound 147 (BATPN-4)

Preparation of Compound 142

15 g (58.3 mmol) of 9-Bromoanthracene, compound 141 , 8.5 g (70.0 mmol) of phenylboromic acid, tetrakispalladiumtriphenylphosphinethiriphenylphosphine (Pd (PPh _{3) 4} ) 6.7 g (5.8 mmol) was dissolved in 300 mL of toluene and 150 mL of ethanol, and then 486 mL of 2M aqueous sodium carbonate solution was stirred under reflux for 5 hours at 120 ° C. After stirring, the temperature was lowered to 25 ° C. and 400 mL of distilled water. The reaction was terminated and the reaction mixture was extracted with 400 mL of ethyl acetate, and the organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized with 300 mL of tetrahydrofuran to obtain 12.0 g (47.2 mmol) of Compound 142 .

Preparation of Compound 143

9.0 g (50.6 mmol) of N-Bromosuccinimide was dissolved in 11.7 g (46.0 mmol) of Compound 142 in a 360 mL solution of dichloromethane under a nitrogen stream, followed by stirring at 25 ° C for 5 hours. Then, 300 mL of distilled water was added to terminate the reaction, and extracted with 300 mL of dichloromethane. The organic layer obtained herein was dried over magnesium sulfate, filtered and concentrated under reduced pressure, and then recrystallized with 200 mL of tetrahydrofuran to give Compound 143 13.0 g (39.0 mmol) were obtained.

Preparation of Compound 145

8.1 g (20.8 mmol) of 1,8-dibromotriphenylene which is Compound 127 and 4.6 g (22.9 mmol) of 4-bromophenylboronic acid were trans-dichlorobistriphenylphosphine. 1.5 g (2.1 mmol) of palladium (II) was added thereto, and dissolved in 140 mL of toluene and 70 mL of ethanol. 100 mL of 2 M sodium carbonate solution was added while stirring, followed by stirring while heating to 90 ° C. After 3 hours of reaction, the mixture was extracted with 300 mL of dichloromethane, washed with 300 mL of sodium chloride, and filtered. Recrystallization with 200 mL of tetrahydrofuran gave 5.0 g (10.8 mmol) of compound 145 .

Preparation of Compound 146

4.8 g (10.3 mmol) of Compound 145 were dissolved in 100 mL of tetrahydrofuran under a stream of nitrogen, and then 12.4 mL (31 mmol) of n-butyllithium (n-BuLi, 2.5 M in n-Hexane) was slowly added dropwise at -78 ° C. After stirring for 1 hour. 2-isopropoxy-4,4,5,5, -tetramethyl-1,3,2-dioxaborolane after 1 hour (2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane) 7.7 g (41.3 mmol) was added under a low temperature and stirred while slowly raising the temperature to 25 ℃. Extracted with 300 mL of ethyl acetate, washed with 300 mL of water, dried over anhydrous magnesium sulfate, filtered and the solid obtained by recrystallization with 200 mL of methanol was filtered off to obtain a solid obtained by drying the compound 146 5.0 g (9 mmol).

Preparation of Compound 147

Compound 146 9 g (27 mmol) and 5.0 g (9 mmol) of the compound 143 ester compound were placed in a reaction vessel, and 1.0 g (0.9 mmol) of tetrakispalladiumtriphenylphosphinethyriphenylphosphine (Pd (PPh ₃ ) ₄ ) was added thereto. Then dissolved in 80 mL of toluene. 0.4 g (0.9 mmol) of aliquat 336 was added thereto, 24 mL of 2 M calcium carbonate solution was added thereto, and the mixture was stirred under reflux at 130 ° C. for 5 hours. At this time, 300 mL of excess methanol was poured into the precipitate formed to form a solid. The resulting mixture was dissolved in 500 mL of chloroform, filtered, and the solvent was dried under reduced pressure. Recrystallization with 200 mL of tetrahydrofuran gave 2.3 g (32% overall yield) of final compound 147 (BATPN-4).

¹ H NMR (200 MHz, CDCl ₃ ) δ = 7.22-7.32 (m, 14H), 7.48-7.54 (m. 8H), 7.67 (t, 8H), 7.82-7.88 (m, 2H), 8.04-8.18 ( m, 4H), 8.34 (d, 1H), 8.93-8.99 (m, 2H), 9.15 (s, 1H)

MS / FAB: 809.32 (found), 809 (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 TPN-4) was placed in one cell in a vacuum deposition apparatus, and the dopant light emitting material having the following structure was put in another cell, and then the deposition rate was 100: 1. A light emitting layer having a thickness of 35 nm was deposited on it.

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, an electron transport layer and an 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 the light emitting compound was measured in 500 cd / ㎡ and 2,000 cd / ㎡ 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 (7)

delete delete delete delete An organic light emitting compound, characterized in that selected from the formula (2) to (5). [Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, A and B are each independently a chemical bond or C ₆ -C ₃₀ arylene; Ar ₁ , 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-diphenyl) phenyl , 9,9-dimethyl-fluoren-2-yl, 9,9-diphenyl-fluoren-2-yl, (9,9- (4-methylphenyl) -fluorene) -2-yl, 1-naph Til, 2-naphthyl, 1-anthryl, 2-anthryl, 3-anthryl, 2-spirofluorenyl. The method of claim 5, wherein 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 claim 5.