KR20140108778A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound represented by chemical formula 1. An organic electroluminescent device comprising the organic electroluminescent compound of the present invention is able to be operated under a lower driving voltage compared to a conventional device with a phosphorescent hast material, and has excellent power efficiency, luminous efficiency, and service life.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic light emitting compound and an organic electroluminescent device including the same.

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type are superior in viewing angle and contrast ratio compared to a liquid crystal display, which is a mainstream of a flat panel display device, require no backlight and are lightweight and thin, And has been attracting attention as a next generation display device.

An organic electroluminescent device is a device that injects electric charge into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole.

The organic electroluminescent device can be formed on a transparent substrate that can be made of plastic and can be driven at a voltage as low as 10 V or less as compared with a plasma display panel or an inorganic electroluminescent display and has a relatively low power consumption , And has an advantage of excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material so far, and an organic electroluminescent device using a BALq derivative as a host is known.

However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no significant advantage in terms of power efficiency due to a high voltage and satisfactory level of life of the device can not be achieved, and development of a more stable and high-performance host material is required.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic luminescent compound having a luminescent efficiency higher than that of a conventional material, and at the same time having improved power efficiency and longevity.

The present invention also provides an organic electroluminescent device with high efficiency and long life by employing the organic electroluminescent compound as a light emitting material.

In order to solve the above problems, the present invention provides an organic luminescent compound represented by the following formula (1)

The organic electroluminescent device includes at least one organic electroluminescent compound.

[Chemical Formula 1]

Each substituent in the above formula (1) will be described later.

The organic electroluminescent device may include a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organic electroluminescent compound .

The organic layer may include at least one selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

In addition, the organic light emitting compound may be used as a phosphorescent host, and the organic layer may further include at least one phosphorescent dopant compound.

The organic electroluminescent device may further include one or more organic electroluminescent layers emitting blue, red, or green light to emit white light.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention has a lower driving voltage than the conventional electroluminescent host material and has excellent power efficiency and luminous efficiency and long life.

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

An aspect of the present invention relates to an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), A ₁ to A ₄ each independently represent CX ₁₁ , and two adjacent ones of A ₁ to A ₄ are bonded to B to form a condensed ring. According to a preferred embodiment, The formula (1) may be any one selected from the following formulas (1-a) to (1-f)

[Chemical Formula 1-a] [Chemical Formula 1-b]

[Chemical Formula 1-c] [Chemical Formula 1-d]

[Chemical Formula 1-e] [Chemical Formula 1-f]

Wherein X ₁ to X ₁₁ are the same or different from each other and each independently represents a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2- To 50 heteroaryl groups, hydrogen and deuterium.

L is a chemical bond, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P), and silicon A substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, and a substituted or unsubstituted C3 to C30 cycloalkyl; and m is an integer of 0 to 3.

R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, An aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms .

According to a preferred embodiment, R may be selected from the following [formula 1].

[Structural formula 1]

Y is CR ₁ , NR ₁ , S, O, or N, and at least one of Y in the structural formulas is N.

R ₁ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, an amino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, A substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, A substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, a substituted Is selected from the alkynyl group of the unsubstituted carbon atoms of from 5 to 60 get Im aryl, substituted or unsubstituted C2 to 60 alkenyl group and a substituted or unsubstituted C2 to 60 ring unsubstituted.

When a plurality of R _{1 s} are present, they may be the same or different from each other and may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group, and the monocyclic or polycyclic ring May be substituted with any one or more heteroatoms selected from N, S, and O.

When the X ₁ to X _11, L, R and R ₁ is further substituted, the substituent is hydrogen, heavy hydrogen, a cyano group, a halogen group, a nitro group, an alkyl group having 1 to 40 carbon atoms, C 6 -C 40 aryl group, An aryloxy group having 1 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, and an arylthio group having 6 to 40 carbon atoms. And at least one selected from the group consisting of

The organic luminescent compound represented by the formula (1) according to the present invention may be more specifically a compound represented by the following formulas (2) to (163).

[Chemical Formula 2] < EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Chemical Formula 115]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[Formula 124] [Formula 124] [Formula 125]

[Formula 126] < EMI ID = 129.1 >

[Formula 130] < EMI ID = 131.0 >

[Formula 135] [Formula 135] [Formula 137]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[163]

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, And at least one organic luminescent compound represented by the following formula (1).

The organic layer includes at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the organic light emitting compound according to the present invention is contained in the light emitting layer and used as a phosphorescent host compound.

In addition, the light emitting layer may further include at least one phosphorescent dopant compound in addition to the organic electroluminescent compound represented by Formula 1, and the phosphorescent dopant compound to be applied to the organic electroluminescent device according to the present invention is not particularly limited, , A compound represented by the following formula (I).

(I)

In the above formula (I)

M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ₁ , L ₂ And L < ₃ > are each independently selected from the following [formula 2].

[Structural formula 2]

In the above formula 2,

R is the same or different from each other and is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms .

Each R is independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, Which is further substituted with one or more substituents selected from adjacent alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

Further, L is selected from the following [formula 3].

[Structural Formula 3]

In Formula 3, X is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, A substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 cycloalkyl group.

The L may be an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, More preferably more than one kind of substituent, and may be connected to adjacent substituents by alkylene or alkenylene to form a spiro ring or a fused ring.

According to a preferred embodiment of the present invention, the formula (I) may be selected from the compounds represented by the following formula (II).

[Formula II]

The organic electroluminescent device according to the present invention may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer in addition to the light emitting layer. May be used for the hole injecting layer, the hole transporting layer, the electron injecting layer, and the electron transporting layer in addition to the light emitting layer.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO) or the like which is transparent and excellent in conductivity is used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. It will be clear to those who have knowledge.

Synthesis Example 1 Synthesis of Compound Represented by Formula 2

(1) Synthesis of Compound Represented by Formula (1-a)

A compound represented by the formula (1-a) was synthesized by the following reaction scheme (1).

[Reaction Scheme 1]

[Chemical Formula 1-a]

The dried 2 L reactor was charged with nitrogen, 100 g (510 mmol) of xanthan and 600 mL of toluene were added and the temperature was lowered to 0 占 폚. 612 mL (1223 mmol) of 2 M trimethylaluminum was slowly dropped, stirred at 0 ° C for 2 hours, and then stirred at room temperature for 4 hours.

When the reaction was completed, 300 mL of hydrochloric acid was diluted with 2 L of water, and the reaction product was gradually poured at a low temperature. The mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, and then separated by column chromatography to obtain 53.8 g of a compound represented by the formula (1-a). (Yield: 52%)

(2) Synthesis of Compound Represented by Formula (1-b)

[Chemical Formula 1-b] was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

[Chemical Formula 1-a] [Chemical Formula 1-b]

53.8 g (256 mmol) of the compound represented by the formula (1-a) obtained from the above-mentioned scheme 1 was dissolved in 540 mL of tetrahydrofuran in a nitrogen stream, and 160 mL of 1.6 M normal- 256 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining the temperature at -78 ° C. Then, 31.9 g (307 mmol) of trimethyl borate was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour.

When the reaction is completed, 200 mL of a 1 M aqueous hydrochloric acid solution is added dropwise at room temperature, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and recrystallized in methylene chloride and hexane to obtain 15 g of a compound represented by the formula (1-b). (Yield: 23%)

(3) Synthesis of Compound Represented by Formula (1-c)

The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].

[Reaction Scheme 3]

[Chemical Formula 1-b] [Chemical Formula 1-c]

19.4 g (76 mmol) of the compound represented by the general formula [1-b] obtained from the above-mentioned Reaction Scheme 2, 14 g (69 mmol) of 2-bromonitrobenzene, 1.6 g of tetrakis (triphenylphosphine) palladium 1.38 mmol), potassium carbonate (19.2 g, 139 mmol), 1,4-dioxane (100 mL), toluene (100 mL) and distilled water (40 mL).

When the reaction is complete, extract using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure to obtain 5.8 g of a compound represented by the formula (1-c). (Yield: 25%)

(4) Synthesis of a compound represented by the formula (1-d)

[Chemical Formula 1-d] was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

[Chemical Formula 1-c] [Chemical Formula 1-d]

7.0 g (13 mmol) of the compound represented by the formula (1-c) and 10 g (42 mmol) of triphenylphosphine obtained from the above scheme 3 are added to 100 mL of dichlorobenzene and the mixture is refluxed for 12 hours. When the reaction was completed, the solution was concentrated and then separated by column chromatography to obtain 4 g of a compound represented by the formula (1-d). (Yield: 49%)

(5) Synthesis of Compound Represented by Formula 2

A compound represented by the formula (2) was synthesized by the following reaction scheme (5).

[Reaction Scheme 5]

[Chemical Formula 1-d] [Chemical Formula 2]

6 g (20.04 mmol) of the compound represented by the formula 1-d and 0.72 g (30.063 mmol) of 60% sodium hydride obtained from the above scheme 4 are added to 60 mL of dimethylformamide and stirred at room temperature for 30 minutes . Then, 6.44 g (24.05 mmol) of chlorodiphenyltriazine was dissolved in 60 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, 60 mL of distilled water was added, followed by filtration and recrystallization to obtain 5.5 g of a compound represented by the formula (2). (Yield: 51%)

Synthesis Example 2 Synthesis of Compound Represented by Formula 3

(1) Synthesis of Compound Represented by Formula (2-a)

A compound represented by the formula (2-a) was synthesized by the following reaction scheme [6].

[Reaction Scheme 6]

[Chemical Formula 2-a]

18.0 g (89.7 mmol) of 3-bromophenylboronic acid, 1.7 g (1.5 mmol) of tetrakis (triphenylphosphine) palladium and 20.7 g (149.4 mmol ), 100 mL of 1,4-dioxane, 100 mL of toluene, and 50 mL of distilled water, and the mixture is stirred at 100 ° C for 12 hours.

When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 23.2 g of a compound represented by the formula (2-a). (Yield: 80%)

(2) Synthesis of Compound Represented by Formula 3

[Chemical Formula 3] was synthesized by the following Reaction Scheme 7.

[Reaction Scheme 7]

[Chemical Formula 1-d] [Chemical Formula 2-a] [Chemical Formula 3]

20.0 g (55.80 mmol) of the compound represented by the formula (1-d) obtained from the above scheme 4, 36.43 g (88.7 mmol) of the compound represented by the formula 2-a obtained from the above scheme 6, 7.09 g (111.6 mmol) of 18-crown-6, 2.95 g (11.16 mmol) of potassium carbonate and 123.14 g (167.4 mmol) of potassium carbonate were added in this order. 200 mL of 1,2-dichlorobenzene was added thereto, Reflux and stir.

After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 27.3 g of a compound represented by the formula (3). (Yield: 73.5%)

Synthesis Example 3 Synthesis of Compound Represented by Formula 4

(1) Synthesis of Compound Represented by Formula 3-a

A compound represented by the general formula [3-a] was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

[Formula 3-a]

23.88 g (120.6 mmol) of 4-biphenylboronic acid, 2.3 g (2.0 mmol) of tetrakis (triphenylphosphine) palladium and 27.78 g (200.9 mmol) Add 600 mL of tetrahydrofuran, 400 mL of toluene and 400 mL of distilled water, and stir for 9 hours.

After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure and then recrystallized with toluene to obtain 26.7 g of a compound represented by the formula (3-a). (Yield: 83%)

(2) Synthesis of Compound Represented by Formula 4

[Chemical Formula 4] was synthesized by the following Reaction Scheme 9.

[Reaction Scheme 9]

[Chemical Formula 1-d] [Chemical Formula 3-a] [Chemical Formula 4]

7.0 g (23.382 mmol) of the compound represented by the formula (1-d) obtained in the above scheme 4 and 0.84 g (35.074 mmol) of 60% sodium hydride were placed in 70 mL of dimethylformamide and stirred at room temperature for 30 minutes . Then, 8.89 g (28.059 mmol) of [Formula 3-a] is dissolved in 100 mL of dimethylformamide, and the solution is slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 6.0 g of a compound represented by the formula (4). (Yield: 44%)

Synthesis Example 4 Synthesis of Compound Represented by Formula 36

(1) Synthesis of Compound Represented by Formula (36)

A compound represented by the formula (36) was synthesized by the following reaction scheme (10).

[Reaction Scheme 10]

[Chemical Formula 1-d] [Chemical Formula 36]

7.0 g (23.382 mmol) of the compound represented by the formula (1-d) obtained in the above scheme 4 and 0.84 g (35.074 mmol) of 60% sodium hydride were placed in 70 mL of dimethylformamide and stirred at room temperature for 30 minutes . 7.48 g (28.059 mmol) of chlorodiphenylpyrimidine is dissolved in 100 mL of dimethylformamide, and the mixture is slowly added dropwise, followed by stirring for 1 hour.

When the reaction was completed, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 8.3 g of a compound represented by the formula (36). (Yield 67%)

Synthesis Example 5 Synthesis of Compound Represented by Formula 38

(1) Synthesis of a compound represented by the formula (5-a)

A compound represented by the following formula (5-a) was synthesized by the following reaction scheme (11).

[Reaction Scheme 11]

[Formula 5-a]

2.3 g (2.0 mmol) of tetrakis (triphenylphosphine) palladium and 27.78 g (200.9 mmol) of potassium carbonate were added to a solution of 20.0 g (100.5 mmol) of dichloroquinazoline, 14.70 g 600 mL of toluene, 400 mL of toluene and 400 mL of distilled water, and the mixture is refluxed with stirring for 9 hours.

After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and then recrystallized from toluene to obtain 18.54 g of a compound represented by the formula (5-a). (Yield: 77%)

(2) Synthesis of Compound Represented by Formula 5-b

[Chemical Formula 5-b] was synthesized by the following Reaction Scheme 12.

[Reaction Scheme 12]

[Formula 5-a] [Formula 5-b]

10.0 g (41.55 mmol) of the compound represented by the formula 5-a obtained from the above Reaction Scheme 11, 10.0 g (49.86 mmol) of 4- bromophenylboronic acid, 0.97 g of tetrakis (triphenylphosphine) palladium (0.83 mmol), potassium carbonate (11.48 g, 83.09 mmol), 1,4-dioxane (100 mL), toluene (100 mL) and distilled water (50 mL).

When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 9.6 g of a compound represented by the formula 5-b. (Yield 64%)

(3) Synthesis of Compound Represented by Formula 38

[Chemical Formula 38] was synthesized by the following Reaction Scheme (13).

[Reaction Scheme 13]

[Chemical Formula 1-d] [Chemical Formula 5-b] [Chemical Formula 38]

5.8 g (16.702 mmol) of the compound represented by the above formula [5-b], 3.18 g (50.105 mmol) of the copper powder obtained in the above Reaction Scheme 4, 0.88 g (3.34 mmol) of 18-crown-6 and 11.54 g (83.509 mmol) of potassium carbonate were added in this order. 50 mL of 1,2-dichlorobenzene was added thereto and the mixture was refluxed and stirred at 180 ° C for 1 day .

After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 4.3 g of a compound represented by the formula (38). (Yield: 42%)

Synthesis Example 6 Synthesis of Compound Represented by Formula 39

(1) Synthesis of Compound Represented by Formula (6-a)

A compound represented by the formula (6-a) was synthesized by the following reaction scheme [14].

[Reaction Scheme 14]

[Formula 5-a] [Formula 6-a]

10.0 g (41.55 mmol) of the compound represented by the formula 5-a obtained from the above-mentioned scheme 11, 10.0 g (49.86 mmol) of 3-bromophenylboronic acid, 0.97 g of tetrakis (triphenylphosphine) palladium (0.83 mmol), potassium carbonate (11.48 g, 83.09 mmol), 1,4-dioxane (100 mL), toluene (100 mL) and distilled water (50 mL).

When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 11.0 g of a compound represented by the formula 6-a. (Yield: 73%)

(2) Synthesis of Compound Represented by Formula 39

A compound represented by the formula (39) was synthesized by the following scheme (15).

[Reaction Scheme 15]

[Chemical Formula 1-d] [Chemical Formula 6-a] [Chemical Formula 39]

5.5 g (18.37 mmol) of the compound represented by the formula 1-d obtained from the above reaction scheme 4, 8.25 g (20.21 mmol) of the compound 6-a obtained from the above scheme 14 and 3.5 g 0.74 g (3.67 mmol) of 18-crown-6 and 12.70 g (91.86 mmol) of potassium carbonate were added in this order. 555 mL of 1,2-dichlorobenzene was added thereto, and the mixture was refluxed and stirred for 1 day at 180 ° C .

After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 6.3 g of a compound represented by the formula (39). (Yield: 59%)

Synthesis Example 7 Synthesis of Compound Represented by Formula 62

(1) Synthesis of Compound Represented by Formula 7-a

A compound represented by the general formula [7-a] was synthesized by the following scheme [Scheme 16].

[Reaction Scheme 16]

[Formula 1-a] [Formula 7-a]

50 g (237.79 mmol) of the compound represented by the formula (1-a) obtained in the above reaction scheme 1 was dissolved in 400 mL of tetrahydrofuran in a nitrogen stream, and 111 mL of 1.6 M n-butyllithium 285.34 mmol) was slowly added dropwise, and the mixture was stirred for 1 hour while keeping the temperature at -78 ° C. After that, 66.38 g (261.56 mmol) of iodine was slowly added dropwise, and the mixture was stirred at room temperature for 1 hour.

After completion of the reaction, 500 mL of sodium thiosulfate aqueous solution is added dropwise, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 21.4 g of a compound represented by the formula 7-a. (Yield: 26%)

(2) Synthesis of Compound Represented by Formula 7-b

[Chemical Formula 7-b] was synthesized by the following Reaction Scheme [17].

[Reaction Scheme 17]

[Formula 7-a] [Formula 7-b]

20 g (53.58 mmol) of the compound represented by the general formula [7-a], 9.22 g (53.58 mmol) of 2-bromoaniline and 0.9 g 10 g (107.17 mmol) of sodium tertiary butoxide, 1.1 g (2.14 mmol) of 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl and 200 mL of toluene, Lt; / RTI >

When the reaction is completed, the reaction is filtered under reduced pressure in a hot state. After the solution was dried under reduced pressure, 16.4 g (73%) of the compound represented by the general formula [7-b] was obtained by column chromatography.

(3) Synthesis of Compound Represented by Formula 7-c

[Chemical Formula 7-c] was synthesized by the following Reaction Scheme 18.

[Reaction Scheme 18]

[Formula 7-b] [Formula 7-c]

20 g (39.45 mmol) of the compound represented by the formula [7-b] obtained from the above-mentioned scheme [17], tetrakistriphenylphosphine palladium 1.82 g (1.58 mmol), potassium acetate (5.8 g, 59.167 mmol) and dimethylacetamide (150 mL) were added and refluxed for 12 hours. The reaction solution was filtered using celite, and the filtrate was concentrated under reduced pressure, and then purified by column chromatography to obtain 5.3 g of [Formula 7-c]. (Yield: 44.9%)

(4) Synthesis of Compound Represented by Formula 62

A compound represented by the formula (62) was synthesized according to the following scheme (Scheme 19).

[Reaction Scheme 19]

[Chemical Formula 7-c] [Chemical Formula 62]

4 g (13.36 mmol) of the compound represented by the above formula [7-c] and 0.48 g (20.04 mmol) of 60% sodium hydride obtained from the above-mentioned Scheme 18 were added to 60 mL of dimethylformamide and stirred at room temperature for 30 minutes . Then, 4.29 g (24.05 mmol) of chlorodiphenyltriazine was dissolved in 40 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, 50 mL of distilled water was added, followed by filtration and recrystallization to obtain 5.2 g of a compound represented by the formula (62). (Yield: 73%)

Synthesis Example 8 Synthesis of Compound Represented by Formula 64

(1) Synthesis of Compound Represented by Formula 64

A compound represented by the formula (64) was synthesized by the following reaction scheme (20).

[Reaction Scheme 20]

[Chemical Formula 7-c] [Chemical Formula 3-a] [Chemical Formula 64]

7.0 g (23.382 mmol) of the compound represented by the above formula [7-c] and 0.84 g (35.074 mmol) of 60% sodium hydride obtained in the above Reaction Scheme 18 were placed in 70 ml of dimethylformamide and stirred at room temperature for 30 minutes . Then, 8.89 g (28.059 mmol) of [Formula 3-a] is dissolved in 100 mL of dimethylformamide, and the solution is slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 9.0 g of a compound represented by the formula (64). (Yield 66%)

Synthesis Example 9 Synthesis of Compound Represented by Formula 74

(1) Synthesis of Compound Represented by Formula 74

A compound represented by the formula (74) was synthesized by the following Reaction Scheme (21).

[Reaction Scheme 21]

[Chemical Formula 7-c] [Chemical Formula 5-a] [Chemical Formula 74]

5.0 g (16.702 mmol) of the compound represented by the formula [7-c] obtained from the above scheme 18 and 0.60 g (25.053 mmol) of 60% sodium hydride were placed in 50 mL of dimethylformamide and stirred at room temperature for 30 minutes . Then, 4.82 g (20.042 mmol) of [Formula 5-a] was dissolved in 100 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour.

When the reaction was completed, 50 mL of distilled water was added, followed by filtration and recrystallization to obtain 5.2 g of a compound represented by the formula (74). (Yield: 62%)

Synthesis Example 10 Synthesis of Compound Represented by Formula 75

(1) Synthesis of Compound Represented by Formula 75

A compound represented by the formula (75) was synthesized by the following reaction scheme (22).

[Reaction Scheme 22]

[Chemical Formula 7-c] [Chemical Formula 5-b] [Chemical Formula 75]

, 5.8 g (16.702 mmol) of the compound represented by the above formula [5-b], 3.18 g (50.105 g) of the copper powder obtained in the above Reaction Scheme 18, 0.88 g (3.34 mmol) of 18-crown-6 and 11.54 g (83.509 mmol) of potassium carbonate were added in this order. 50 mL of 1,2-dichlorobenzene was added thereto and the mixture was refluxed and stirred at 180 ° C for 1 day .

After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 5.9 g of a compound represented by the formula (75). (Yield: 56%)

Synthesis Example 11 Synthesis of Compound Represented by Formula 76

(1) Synthesis of Compound Represented by Formula (11-a)

A compound represented by the formula (11-a) was synthesized by the following reaction scheme [Reaction formula 23].

[Reaction Scheme 23]

[Formula 3-a] [Formula 11-a]

5 g (13.39 mmol) of the compound represented by the formula 3-a obtained from the above-mentioned reaction formula 8, 3.25 g (16.07 mmol) of 4-bromophenylboronic acid, 0.31 g of tetrakis (triphenylphosphine) palladium (0.26 mmol), potassium carbonate (3.7 g, 26.78 mmol), 1,4-dioxane (50 mL), toluene (50 mL) and distilled water (50 mL).

When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 5.2 g of a compound represented by the formula (11-a). (Yield: 88%)

(2) Synthesis of Compound Represented by Formula 76

A compound represented by the formula [Formula 76] was synthesized by the following Reaction Formula 24.

[Reaction Scheme 24]

[Chemical Formula 7-c] [Chemical Formula 11-a] [Chemical Formula 76]

2.1 g (7.02 mmol) of the compound represented by the formula 7-c obtained from the above scheme 18, 4.0 g (8.42 mmol) of the compound 11-a obtained from the above scheme 23 and 1.34 g 0.37 g (1.4 mmol) of 18-crown-6 and 4.8 g (35.07 mmol) of potassium carbonate were added in this order, and 50 mL of 1,2-dichlorobenzene was added thereto. The mixture was refluxed and stirred at 180 ° C for 1 day . After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 2.9 g of a compound represented by the formula (76). (Yield: 63%)

Synthesis Example 12 Synthesis of Compound Represented by Formula (158)

(1) Synthesis of Compound Represented by Formula 12-a

A compound represented by the formula [12-a] was synthesized by the following reaction scheme [25].

[Reaction Scheme 25]

[Chemical Formula 1-a] [Chemical Formula 12-a]

56 g (266 mmol) of the compound represented by the formula (1-a) obtained from the above-mentioned scheme 1 was dissolved in 600 mL of acetic acid under a nitrogen stream, 42.56 g (266 mmol) of bromine was slowly added dropwise with stirring at 0 ° C, When the dropwise addition is completed, the mixture is stirred for 1 hour while maintaining the temperature at 0 ° C. When the reaction is completed, 200 mL of a 1 M aqueous hydrochloric acid solution is added dropwise at room temperature, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and recrystallized in methylene chloride and hexane to obtain 19.3 g of a compound represented by the formula (12-a). (Yield 32%)

(2) Synthesis of Compound Represented by Formula 12-b

[Chemical Formula 12-b] was synthesized by the following Reaction Formula 26.

[Reaction Scheme 26]

[Chemical Formula 12-a] [Chemical Formula 12-b]

100 g (346 mmol) of the compound represented by the formula 12-a obtained from the above-mentioned reaction scheme 25 was dissolved in 100 mL of tetrahydrofuran in a nitrogen stream, and thereto was added dropwise a solution of 1.6 M of n-butyl lithium in 260 mL 415 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while maintaining the temperature at -78 ° C. Then, 50.3 g (484 mmol) of trimethyl borate was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour.

When the reaction is completed, 200 mL of a 1 M aqueous hydrochloric acid solution is added dropwise at room temperature, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and recrystallized in methylene chloride and hexane to obtain 72 g of a compound represented by the formula (12-b). (Yield: 82%)

(3) Synthesis of Compound Represented by Formula 12-c

[Chemical Formula 12-c] was synthesized by the following Reaction Scheme 27.

[Reaction Scheme 27]

[Chemical Formula 12-b] [Chemical Formula 12-c]

50 g (196 mmol) of the compound represented by the formula 12-b obtained from the above-mentioned scheme 26, 33 g (163 mmol) of 2-bromonitrobenzene and 3.7 g of tetrakis (triphenylphosphine) palladium 3.26 mmol), potassium carbonate (45.2 g, 139 mmol), 1,4-dioxane (300 mL), toluene (300 mL) and distilled water (120 mL). When the reaction is complete, extract using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure to obtain 43 g of a compound represented by the formula (12-c). (Yield: 79%)

(4) Synthesis of Compound Represented by Formula 12-d

A compound represented by the formula [12-d] was synthesized by the following scheme [Reaction formula 28].

[Reaction Scheme 28]

[Chemical Formula 12-c] [Chemical Formula 12-d]

43 g (129 mmol) of the compound represented by the above formula [12-c] and 88 g (337 mmol) of triphenylphosphine obtained from the above-mentioned scheme 27 were placed in 430 mL of dichlorobenzene and refluxed with stirring for 12 hours. When the reaction was completed, the reaction mixture was concentrated and then separated by column chromatography to obtain 4 g of the product. Filtered and then recrystallized to obtain 7.1 g of a compound represented by the formula [12-d]. (Yield: 18%)

(5) Synthesis of Compound Represented by Formula (158)

A compound represented by the formula (158) was synthesized by the following scheme (29).

[Reaction Scheme 29]

[Chemical Formula 12-d]

7 g (23.38 mmol) of the compound represented by the formula 12-d obtained in the above Reaction scheme 28 and 0.85 g (28.05 mmol) of 60% sodium hydride were placed in 70 ml of dimethylformamide and stirred at room temperature for 30 minutes . 7.5 g (28.06 mmol) of chlorodiphenyltriazine was dissolved in 70 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, 70 ml of distilled water was added, followed by filtration and recrystallization to obtain 8.6 g of a compound represented by the formula (158). (Yield 69%)

Synthesis Example 13 Synthesis of Compound Represented by Formula 159

(1) Synthesis of Compound Represented by Formula (13-a)

[Chemical Formula 13-a] was synthesized by the following Reaction Formula 30.

[Reaction Scheme 30]

[Chemical Formula 12-a] [Chemical Formula 13-a]

A mixture of 50 g (172 mmol) of the compound represented by the formula 12-a obtained in the above Reaction Scheme 25, 29.74 g (172 mmol) of 2-bromoaniline and 3.16 g (3.4 mmol) of tris (dibenzylideneacetone) dipalladium ), Sodium tertiary butoxide (33.23 g, 345.82 mmol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (3.8 g, 6.92 mmol) and toluene (200 mL) . When the reaction is completed, the reaction is filtered under reduced pressure in a hot state. After the solution was dried under reduced pressure, 45.5 g of a compound represented by the following formula (13-a) was obtained by column chromatography (yield: 69%).

(2) Synthesis of Compound Represented by Formula (13-b)

[Chemical Formula 13-b] was synthesized by the following Reaction Formula 31.

[Reaction Scheme 31]

[Chemical Formula 13-a] [Chemical Formula 13-b]

45.5 g (109 mmol) of the compound represented by the formula (13-a) obtained from the above-mentioned scheme [30], tetrakistriphenylphosphine palladium 5.04 g, (4.3 mmol), 16.04 g (160.4 mmol) of potassium acetate and 450 mL of dimethylacetamide were added and refluxed for 12 hours. The reaction solution was filtered using celite, and the filtrate was concentrated under reduced pressure and then purified by column chromatography to obtain 4.9 g of a compound represented by the formula (13-b). (Yield: 13%)

(3) Synthesis of Compound Represented by Formula 159

A compound represented by the formula (159) was synthesized according to the following scheme (Reaction formula 32).

[Reaction Scheme 32]

[Chemical Formula 13-b]

4 g (13 mmol) of the compound represented by the above formula [13-b] and 0.48 g (25 mmol) of 60% sodium hydride obtained in the above Reaction Scheme 31 were added to 40 mL of dimethylformamide and stirred at room temperature for 30 minutes . 3.8 g (16 mmol) of [Formula 5-a] was dissolved in 40 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 40 mL of distilled water was added, followed by filtration and recrystallization to obtain 4.3 g of a compound represented by the formula (159). (Yield 64%)

Synthesis Example 14 Synthesis of Compound Represented by Formula 161

(1) Synthesis of Compound Represented by Formula (14-a)

A compound represented by the following formula (14-a) was synthesized by the following reaction scheme (33).

[Reaction Scheme 33]

[Chemical Formula 13-a] [Chemical Formula 14-a]

45.5 g (109 mmol) of the compound represented by the formula (13-a) obtained from the above-mentioned Reaction formula 30, 10 g of tetrakistriphenylphosphine palladium 5.04 g (4.3 mmol) of potassium acetate, 16.04 g (160.4 mmol) of potassium acetate and 450 mL of dimethylacetamide were charged and refluxed for 12 hours. The reaction solution was filtered using celite, and the filtrate was concentrated under reduced pressure and then purified by column chromatography to obtain 3.6 g of a compound represented by the following formula (14-a). (Yield: 9.5%)

(2) Synthesis of Compound Represented by Formula 161

A compound represented by the formula (161) was synthesized by the following reaction scheme (34).

[Reaction Scheme 34]

[Chemical Formula 14-a] [Chemical Formula 161]

3.6 g (12 mmol) of the compound represented by the formula 14-a and 0.43 g (18 mmol) of 60% sodium hydride obtained in the above reaction scheme 33 were added to 35 ml of dimethylformamide and stirred at room temperature for 30 minutes . Then 3.4 g (14 mmol) of [Formula 5-a] was dissolved in 35 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 35 mL of distilled water was added, followed by filtration and recrystallization to obtain 2.9 g of a compound represented by the formula (161). (Yield: 48%)

Examples 1 to 14: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, an organic material was deposited on the ITO using DNTPD (700 Å), NPD (300 Å) (10 Å) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å) were deposited in this order and measured at 0.4 mA.

[RD-1]

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that BAlq, which is generally used as a phosphorescent host material, was used instead of the compound manufactured by the invention in the device structure of the embodiment, and the structure of BAlq is as follows.

division Host Dopant Current (mA) V Cd / m ² CIEx CIEy T ₅₀ (Hr) Comparative Example 1 BAlq RD-1 10 6.7 1100 0.636 0.338 2500 Example 1 2 RD-1 10 4.5 1340 0.633 0.335 4700 Example 2 3 RD-1 10 5.2 1310 0.634 0.334 5600 Example 3 4 RD-1 10 4.5 1540 0.635 0.332 9300 Example 4 36 RD-1 10 4.7 1280 0.630 0.336 4500 Example 5 38 RD-1 10 4.2 1570 0.632 0.334 9700 Example 6 39 RD-1 10 5.1 1550 0.634 0.335 9500 Example 7 62 RD-1 10 4.6 1320 0.632 0.334 4500 Example 8 64 RD-1 10 4.4 1350 0.639 0.338 5100 Example 9 74 RD-1 10 4.7 1490 0.633 0.336 9800 Example 10 75 RD-1 10 4.5 1520 0.633 0.335 9100 Example 11 76 RD-1 10 4.8 1510 0.639 0.334 8900 Example 12 158 RD-1 10 4.2 1340 0.630 0.334 4900 Example 13 159 RD-1 10 4.7 1540 0.633 0.332 9700 Example 14 161 RD-1 10 4.6 1500 0.632 0.333 8900

In Table 1, T ₅₀ represents the time required for the luminance to be reduced to 50% of the initial luminance.

As shown in Table 1, when the organic electroluminescent compound implemented according to the present invention is employed as a host compound for the light emitting layer of an organic electroluminescent device, the lifetime characteristics Is remarkably improved, and not only the light emitting characteristic is excellent, but also the drive voltage is lowered, thereby leading to an increase in the power efficiency, thereby improving the power consumption.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (16)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
A ₁ to A ₄ each independently represent CX ₁₁ , and two adjacent ones of A ₁ to A ₄ are bonded to B to form a condensed ring,
X ₁ to X ₁₁ are the same or different from each other and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted group having 2 to 50 carbon atoms Lt; / RTI > is selected from hydrogen,
L is a chemical bond, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P), and silicon A substituted or unsubstituted aryl group having 2 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms wherein at least one of substituted or unsubstituted C3 to C30 cycloalkyl is fused,
R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, A substituted or unsubstituted C1-C30 alkylamino group, or a substituted or unsubstituted C6-C30 arylamino group. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms ,
and m is an integer of 0 to 3. The method according to claim 1,
Wherein X ₁ to X _11, L and R is hydrogen, heavy hydrogen, a cyano group, a halogen group, a nitro group, a heteroaryl group having 1 to 40 alkyl group, having 6 to 40 carbon atoms of the aryl group, having 2 to 40 carbon atoms, 1 Further substituted with at least one member selected from the group consisting of an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 1 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms and an arylthio group having 6 to 40 carbon atoms Wherein the organic compound is an organic compound. The method according to claim 1,
Wherein X ₁ to X ₁₁ , L, R and substituents thereof are bonded to each other with adjacent substituents to form a saturated or unsaturated ring. The method according to claim 1,
The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following Formulas 1-a to 1-f:
[Chemical Formula 1-a] [Chemical Formula 1-b]

[Chemical Formula 1-c] [Chemical Formula 1-d]

[Chemical Formula 1-e] [Chemical Formula 1-f]

In the above formulas (1-a) to (1-f)
The definitions of X ₁ to X ₁₁ , L and R are the same as those in formula (1). The method according to claim 1,
Wherein R is selected from the following Structural Formula 1:
[Structural formula 1]

In the above formula 1,
Y is CR ₁ , NR ₁ , S, O or N, and at least one of Y in the structural formulas is N, and R ₁ is hydrogen, deuterium, a halogen group, a cyano group, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted heterocyclic group, A substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C30 arylsilyl group, a substituted or unsubstituted C1-C50 arylalkylamino group, a substituted or unsubstituted C1-C60 arylthio group, a substituted or unsubstituted C2-C60 alkenyl group, And an alkynyl group having 2 to 60 carbon atoms. 6. The method of claim 5,
Wherein when a plurality of R < _{1 > s} are present, they are the same as or different from each other and are connected to adjacent substituents to form a saturated or unsaturated ring. The method according to claim 1,
The organic luminescent compound according to claim 1, wherein the compound represented by formula (1) is any one selected from compounds represented by the following formulas (2) to (163)

[Chemical Formula 2] < EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Chemical Formula 115]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[Formula 124] [Formula 124] [Formula 125]

[Formula 126] < EMI ID = 129.1 >

[Formula 130] < EMI ID = 131.0 >

[Formula 135] [Formula 135] [Formula 137]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[163] 8. An organic electroluminescent device comprising at least one organic electroluminescent compound selected from the group consisting of the organic electroluminescent compounds according to any one of claims 1 to 7. A first electrode; A second electrode, and at least one organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises at least one organic electroluminescent compound selected according to any one of claims 1 to 7. 10. The method of claim 9,
Wherein the organic layer comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. 10. The method of claim 9,
Wherein the organic light emitting compound is used as a phosphorescent host, and the organic layer further comprises at least one phosphorescent dopant compound. 12. The method of claim 11,
Wherein the dopant compound is a compound represented by the following formula (I): < EMI ID =
(I)

In the above formula (I)
M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16,
The ligands L ₁ , L ₂ And L < ₃ > are each independently selected from the following [formula 2]
[Structural formula 2]

In the above formula 2,
R is the same or different from each other and is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms . 13. The method of claim 12,
Each R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen Wherein the substituent is further substituted with one or more substituents, and adjacent substituents are connected to alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. 13. The method of claim 12,
Wherein L in the above formula 2 is selected from the following formula 3:
[Structural Formula 3]

In the above formula 3,
X is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms,
Wherein L is at least one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, Lt; / RTI > is further substituted with a substituent and may be connected to an adjacent substituent with an alkylene or alkenylene to form a spiro ring or a fused ring. 13. The method of claim 12,
The organic electroluminescent device according to claim 1, wherein the compound represented by Formula (I) is selected from compounds represented by Formula (II)
[Formula II]

10. The method of claim 9,
Wherein the organic electroluminescent device comprises one or more organic electroluminescent layers emitting blue, red or green light to emit white light.

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