KR20140034709A - Heterocyclic com pounds and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a novel heterocyclic compound and an organic light emitting element including the same as a light-emitting material and, more specifically, to a heterocyclic compound having excellent light emission properties, such as a driving voltage, luminous efficiency, and lifetime, and an organic light emitting element including the same. Since the organic light-emitting compound according to the present invention is more stable compared to conventional materials and has the excellent light emission properties for a driving voltage or current efficiency, the organic light emitting element including the same can be driven with a low-voltage and light emission efficiency can be improved.

Description

Heterocyclic com pounds and organic light-emitting diodes including the same

The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same as a light emitting material, and more particularly, to a heterocyclic compound having excellent driving voltage, luminous efficiency and lifetime characteristics, and an organic electroluminescent device comprising the same. will be.

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type have superior viewing angles and contrast ratios as compared with liquid crystal displays (LCDs), which are the mainstream of flat panel display devices, and require no backlight, It is attracting attention as a next-generation display device because it is advantageous in terms of power and has a wide color reproduction range.

In organic light emitting diodes (OLEDs), when electrons are injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), electrons and holes are paired, to be. The organic electroluminescent device usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, . When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out.

Organic electroluminescent devices can not only form devices on flexible transparent substrates such as plastics, but also at lower voltages of 10V or less than plasma display panels or inorganic electroluminescent (EL) displays. It has the advantage of being able to drive, relatively low power consumption, and excellent color. In addition, organic electroluminescent devices can display three colors of green, blue, and red, making them an object of interest for a large number of people as a next-generation rich color display device.

In order to fully exhibit these characteristics, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. must be supported by a stable and efficient material, yet Until now, the development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved. Therefore, the development of new materials continues to be demanded.

Accordingly, the present invention is to provide a novel heterocyclic compound having a low driving voltage, excellent luminous efficiency and lifespan characteristics, and an organic light emitting device including the same, as compared with the compound used in the conventional phosphorescent material.

The present invention provides a heterocyclic compound represented by the following [Formula 1] to solve the above problems.

[Formula 1]

In addition, the present invention provides an organic light emitting display device including an anode, a cathode, and an organic material layer interposed between the anode and the cathode and including a heterocyclic compound represented by the above [Formula 1].

Specific substituents of the organic light emitting compound represented by the above [Formula 1] will be described later.

The heterocyclic compound according to the present invention is more stable than conventional materials, and enables low voltage driving of the organic light emitting device, thereby improving power efficiency of the device, and also having an excellent light emitting efficiency and long lifespan. The device can be implemented.

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.

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

The organic luminescent compound according to the present invention is characterized by being a compound represented by the following formula (1).

[Formula 1]

In the above formula (1)

,수소, 중수소, 할로겐 원자, 히드록실기, 시아노기, 니트로기, 아미노기, 아미디노기, 히드라진, 히드라존, 카르복실기나 이의 염, 술폰산기나 이의 염, 인산이나 이의 염, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기, 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 40의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 40의 알키닐기, -SiR₁R₂R₃ 및 -NR₄R₅ 중에서 선택될 수 있다. 또한, 상기 X₁ 내지 X₈이 각각 -NR₄R₅인 경우 R₄ 및 R₅는 서로 결합하여 탄소수 6 내지 30의 고리를 형성할 수 있다.X ₁ to X ₈ are the same as or different from each other, and each independently

Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted carbon number An alkyl group of 1 to 30, a substituted or unsubstituted aryl group of 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 60 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, -SiR ₁ R ₂ R ₃ and -NR ₄ R ₅ ≪ / RTI > In addition, when X ₁ to X ₈ are each -NR ₄ R ₅ , R ₄ and R ₅ may be bonded to each other to form a ring having 6 to 30 carbon atoms.

R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group Alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or Unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl jade having 5 to 50 carbon atoms A timing, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. It may be selected from a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and a substituted or unsubstituted arylsilyl group having 5 to 50 carbon atoms.

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted carbon group having 2 to 30 carbon atoms It may be a heteroaryl group.

L ₁ and L ₂ are the same as or different from each other, and each independently represent a single bond or a divalent linking group, and when L ₁ and L ₂ are a divalent linking group, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, substituted or Unsubstituted alkenylene group having 2 to 30 carbon atoms, substituted or unsubstituted alkynylene group having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, substituted or unsubstituted carbon group having 6 to 40 carbon atoms It may be an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

n and m are each independently an integer of 0 to 3, when n and m are 2 or more, a plurality of L ₁ and L ₂ are the same or different, respectively, and p is an integer of 0 to 3.

X ₁ to X ₈ , L ₁ , L ₂ , Ar ₁ , Ar ₂ And substituents thereof may be linked to adjacent substituents to form a saturated or unsaturated ring.

In addition, the X ₁ to X ₈ may be connected to an adjacent substituent to form an alicyclic, aromatic monocyclic or polycyclic ring, the carbon atoms of the formed alicyclic, aromatic aromatic monocyclic or polycyclic ring is N, S It may be substituted with any one or more heteroatoms selected from, and O.

According to one embodiment of the present invention, L ₁ and L ₂ may be any one linking group selected from the following [Formula A1] to [Formula A16].

[Formula A1] [Formula A2] [Formula A3] [Formula A4]

[Structure A5] [Structure A6] [Structure A7] [Structure A8]

[Formula A9] [Formula A10] [Formula A11] [Formula A12]

[Structural formula A13] [Structural formula A14] [Structural formula A15] [Structural formula A16]

In the above structural formulas A1 to A16, hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each structural formula.

The 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 20 carbon atoms, alkenyl group of 1 to 20 carbon atoms, alkynyl group of 1 to 20 carbon atoms, A halogenated alkyl group of 1 to 20 carbon atoms, an aryl group of 5 to 24 carbon atoms, a heteroaryl group of 2 to 24 carbon atoms, an alkoxy group of 1 to 20 carbon atoms, an aryloxy group of 5 to 24 carbon atoms, an alkylsilyl group of 1 to 20 carbon atoms It is meant that the substituent is further substituted with one or more substituents selected from a C5-C24 arylsilyl group, a C1-C20 alkylamine group and a C6-C24 arylamine group, said substituents being bonded to each other with adjacent substituents To form a saturated or unsaturated ring.

The carbon number of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 5 to 50 carbon atoms', etc., Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is regarded as unsubstituted. For example, a phenyl group substituted with a butyl group in the para position means a aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

The aryl group, which is a substituent used in the present invention, is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. When an aryl group has a substituent, it may be fused with a neighboring substituent to further form a ring.

Specific examples of the aryl group include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, Naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, naphthyl group, An aromatic group such as a fluorenyl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a pyrenyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

At least one hydrogen atom of the aryl group may be replaced by a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R) 'And R''each independently represent an alkyl group having 1 to 10 carbon atoms, which is referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the present invention may be any one selected from the following [formula 1] to [formula 6].

[Structure 1] [Structure 2] [Structure 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In the above Structural Formulas 1 to 6,

T ₁ to T ₈ may be the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ) , R ₃₁ to R ₄₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms having a substituted or unsubstituted heteroatom, O, N, S, or P, and each of [structural formulas 1] to [ In the structural formula 6, R ₃₁ to R ₄₄ One may form a single bond with the substituent of [Formula 1].

The above-mentioned [formula 3] may include a compound represented by the following formula [3] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above Structural Formulas 1 to 6 can be selected from the following Structural Formula 7.

[Structural Formula 7]

In the above formula 7,

X is hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms 2-20 alkynyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted A substituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Amine group, substituted or unsubstituted aryl group having 5 to 5 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, cyano group, nitro group, halogen group Any one selected from the group consisting of, m is an integer of 1 to 11, when m is 2 or more, a plurality of X is the same or different from each other, any one of the at least one X is a single substituent with the substituent of [Formula 1] Can be combined.

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, , An octyl group, a stearyl group, a trichloromethyl group, and a trifluoromethyl group, and at least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, (in this case, "alkylsilyl group" hereinafter), a substituted or unsubstituted amino group (-NH _2, -NH (R), -N (R ') (R "), where R, R' and R" are each A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms (preferably an alkyl group having 1 to 24 carbon atoms) A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms Group, may be substituted with a heteroarylalkyl group having 1 to 24 carbon atoms heteroaryl group, having 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of the.

Specific examples of the alkoxy group used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group which is a substituent used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl and the like.

Specific examples of the alkenyl group used in the present invention include straight chain or branched chain alkenyl groups and include 3-pentenyl, 4-hexenyl, 5-heptenyl, 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

Although the present invention is not limited by the specific examples of the heterocyclic compound according to [Formula 1] having the structure as described above, specifically, any one of the compounds represented by the following [Formula 2] to [Formula 161] Can be.

    [Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Formula 146] [Formula 147] [Formula 148] [Formula 149]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

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

In addition, the present invention provides an organic light emitting device having an anode, a cathode, interposed between the anode and the cathode, and having a layer containing a heterocyclic compound represented by the above [Formula 1].

At this time, the layer containing the heterocyclic compound is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode as a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer It may further comprise one or more layers selected from the group consisting of.

In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa, and the light emitting layer may further include a material of the following structural formula.

[Ir (ppy) ₃ ]

[Ir (chpy) ₃ ]

[Ir (mchpy) ₃ ]

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The transport layer is laminated in order to easily inject holes from the anode. As the material of the hole transport layer, electron donating molecules having a small ionization potential are used. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. Is used a lot.

In the present invention, the material of the hole transport layer is not particularly limited as commonly used in the art, for example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl-[1, 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (copper phthalocyanine) or Starburst type amines TCTA (4,4 ', 4''-tri (N -carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4 '' -tris- (3-methyl phenylphenylamino) triphenylamine) may be used.

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 light emitting display device according to 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) and the like which are transparent and excellent in conductivity are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. 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, the metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front 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 production examples and examples. However, the following Preparation Examples and Examples are only for illustrating the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited by the following Preparation Examples and Examples. will be.

Manufacturing example

< Manufacturing example  1> Preparation of the compound represented by Formula 5

Step 1: Preparation of the compound represented by Formula 1-a

As shown in [Scheme 1], a compound represented by Chemical Formula 1-a was prepared.

[Reaction Scheme 1]

120.0 g (614.6 mmol) of 10,11-dihydro-5H-dibenz [b, f] azepine was dissolved in 1.2 L of dimethylformamide and stirred at room temperature. To the reaction was added 109.4 g (614.6 mmol) of N-bromosuccinimide in portions and stirred for 10 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water, and the organic layer was concentrated under reduced pressure, and then recrystallized with methylene chloride and hexane to obtain 93.0 g of the compound represented by Chemical Formula 1-a (yield 55%).

Step 2: Preparation of the compound represented by Formula 1-b

As shown in [Scheme 2], a compound represented by Chemical Formula 1-b was prepared.

[Reaction Scheme 2]

50.0 g (182.4 mmol) of the compound represented by Chemical Formula 1-a obtained in step 1, 55.8 g (273.56 mmol) of 2-iodobenzene, 23.2 g (364.75 mmol) of copper powder, and 9.6 g (36.48) of 18-crown-6 mmol) and 75.6 g (547.1 mmol) of potassium carbonate were added in this order, and 500 ml of 1,2-dichlorobenzene was added thereto, followed by reflux and stirring at 180 ° C for 1 day. After completion of the reaction, the solution after the high temperature filter was concentrated and separated by column chromatography with nucleic acid alone to obtain 51.0 g of the compound represented by the general formula 1-b (yield 80%).

Step 3: Synthesis of Compound Represented by Formula 1-c

As shown in [Scheme 3], a compound represented by Chemical Formula 1-c was prepared.

Scheme 3

50.0 g (142.76 mmol) of the compound represented by Chemical Formula 1-b obtained from step 2, 29.5 g (171.31 mmol) of 2-bromoaniline, 2.6 g (2.86 mmol) of tris (dibenzylideneacetone) dipalladium, 1, 1.6 g (2.86 mmol) of 1'-bis (diphenylphosphino) ferrocene, 20.58 g (214.13 mmol) of sodium tert-butoxide and 500 ml of toluene were added, followed by reflux and stirring for 24 hours. After completion of the reaction, the temperature was adjusted to room temperature, and extracted with water and ethyl acetate. The organic layer was dried, concentrated under reduced pressure, separated by column chromatography to obtain 44.0 g of the compound represented by the target compound of Chemical Formula 1-c (yield 70%).

Step 4: Preparation of the compound represented by Formula 1-d

As shown in [Scheme 4], a compound represented by Chemical Formula 1-d was prepared.

[Reaction Scheme 4]

44.0 g (99.96 mmol) of the compound represented by Chemical Formula 1-d obtained from step 3, 2.3 g (1.99 mmol) of tetrakis (triphenylphosphine) palladium, and 14.7 g (149.54 mmol) of potassium acetate are 440 ml of dimethylformamide. After addition to the mixture, the mixture was refluxed and stirred for 24 hours. After the completion of the reaction, the temperature was adjusted to room temperature, and the crystals were filtered off. The filtrate was concentrated and recrystallized with methylene chloride and nucleic acid to obtain 8.0 g of the compound represented by the target compound of Chemical Formula 1-c (yield 22%).

Step 5: Preparation of the compound represented by Formula 5

As shown in [Scheme 5], a compound represented by Chemical Formula 5 was prepared.

[Reaction Scheme 5]

8.0 g (22.19 mmol) of the compound represented by Chemical Formula 1-d obtained in step 4 and 1.3 g (33.19 mmol) of 60% sodium hydride were added to 120 ml of dimethylformamide, followed by stirring at room temperature for 30 minutes. Thereafter, 7.1 g (26.63 mmol) of chlorodiphenyltriazine was dissolved in 80 ml of dimethylformamide, and slowly added dropwise thereto, followed by stirring for 1 hour. After completion of the reaction, 100 ml of distilled water was added, and the resultant was filtered and recrystallized with methylene chloride and acetone to obtain 5.3 g of the compound represented by the target compound of formula (5) (yield 40%).

MS [M] ⁺ 592

< Manufacturing example  2> Preparation of the compound represented by the formula (6)

Step 1: Preparation of the Compound Represented by Formula 2-a

As shown in [Scheme 6], a compound represented by Chemical Formula 2-a was prepared.

 [Reaction Scheme 6]

50.0 g (102.0 mmol) of 5-bromoindole, 41.6 g (204.0 mmol) of iodobenzene, 19.4 g (306.0 mmol) of copper powder, 5.4 g (20.4 mmol) of 18-crown-6, 42.3 g (306.0 mmol) of potassium carbonate ) Was added in this order, 200 ml of 1,2-dichlorobenzene was added, and the mixture was refluxed and stirred at 180 ° C. for 1 day.

After completion of the reaction, the solution after the high temperature filter was concentrated and subjected to column chromatography with hexane alone to obtain 18.9 g of the compound represented by the formula 2-a (yield 68%).

Step 2: Preparation of the Compound Represented by Formula 2-b

As shown in [Scheme 7], a compound represented by Chemical Formula 2-b was prepared.

 [Reaction Scheme 7]

18.9 g (69.4 mmol) of the compound represented by Chemical Formula 2-a obtained in step 1 was dissolved in 400 ml of tetrahydrofuran under a nitrogen stream, stirred at -78 ° C, and 52 ml (83.3 mmol) of 1.6M normal-butyllithium. After slowly dropping, when the dropping was completed, the mixture was stirred for 1 hour while maintaining at -78 ° C. Then, 8.7 g (83.3 mmol) of trimethyl borate was slowly added dropwise, and then stirred at room temperature for 3 hours.

After completion of the reaction, 200 ml of 1M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Then extracted with ethyl acetate and water, the organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and hexane to obtain 9.0 g of the compound represented by the formula 2-b (yield 55%).

Step 3: Preparation of the compound represented by Formula 2-c

As shown in [Scheme 8], a compound represented by Chemical Formula 2-c was prepared.

 [Reaction Scheme 8]

30.0 g (109.43 mmol) of the compound represented by Formula 1-a obtained from step 1 of Preparation Example 1 and 6.6 g (164.14 mmol) of 60% sodium hydride were added to 500 ml of dimethylformamide, followed by 30 minutes at room temperature. Was stirred. Then, 35.15 g (131.31 mmol) of chlorodiphenyltriazine was dissolved in 250 ml of dimethylformamide, slowly added dropwise, and stirred for 1 hour. After completion of the reaction, 100 ml of distilled water was added, and after filtration, recrystallized with methylene chloride and acetone to give 31.0 g of the compound represented by the formula 2-c (yield 56%).

Step 4: Formula To 6  Preparation of indicated compounds

As shown in [Scheme 9], a compound represented by Chemical Formula 6 was prepared.

 [Reaction Scheme 9]

7.0 g (29.68 mmol) of the compound represented by Chemical Formula 2-b obtained from step 2, 10.0 g (19.79 mmol) of the compound represented by Chemical Formula 2-c obtained from Step 3, 460 mg of tetrakis (triphenylphosphine) palladium (0.4 mmol), 5.5 g (39.57 mmol) of potassium carbonate, 50 ml of 1,4-dioxane, 50 ml of toluene, and 20 ml of distilled water were added thereto, followed by stirring at 100 ° C for 12 hours. After the completion of the reaction, the temperature was adjusted to room temperature and the crystals were filtered off. The crystals were recrystallized from methylene chloride and acetone to obtain 6.7 g of a compound represented by the formula (6) (yield 55%).

MS [M] ⁺ 618

< Manufacturing example  3> Preparation of the compound represented by the formula (7)

Step 1: Preparation of the Compound Represented by Formula 3-a

As shown in [Scheme 10], a compound represented by Chemical Formula 7 was prepared.

 [Reaction Scheme 10]

10.0 g (19.79 mmol) of the compound represented by Chemical Formula 2-c obtained from step 3 of Preparation Example 2, 4.0 g (23.74 mmol) of carbazole, 0.36 g (0.40 mmol) of tris (dibenzylideneacetone) dipalladium, 1 0.22 g (0.40 mmol) of 1′-bis (diphenylphosphino) ferrocene, 2.9 g (29.68 mmol) of sodium tert-butoxide and 100 ml of toluene were added thereto, and the mixture was refluxed and stirred for 24 hours. After the completion of the reaction, the temperature was adjusted to room temperature and the crystals were filtered off. The crystals were recrystallized from methylene chloride and acetone to obtain 6.7 g of a compound represented by the formula (7) (yield 57%).

MS [M] ⁺ 592

< Manufacturing example  4> Preparation of the compound represented by the formula (8)

Step 1: Preparation of the Compound of Formula 8

As shown in [Scheme 11], a compound represented by the formula (8) was prepared.

 [Reaction Scheme 11]

10.0 g (19.79 mmol) of the compound represented by Chemical Formula 2-c obtained from step 3 of Preparation Example 2, (9-phenyl-9H-carbazol-3-yl) boronic acid 8.5 g (19.79 mmol), tetrakis (Triphenylphosphine) palladium 460 mg (0.4 mmol), potassium carbonate 5.5 g (39.57 mmol), 50 ml of 1,4-dioxane, 50 ml of toluene, 20 ml of distilled water, and then stirred at 100 ℃ for 12 hours It was. After the completion of the reaction, the temperature was adjusted to room temperature and the crystals were filtered off. The crystals were recrystallized from methylene chloride and acetone to obtain 5.4 g of a compound represented by the formula (8) (yield 41%).

MS [M] ⁺ 668

< Manufacturing example  5> Preparation of the compound represented by Chemical Formula 30]

Step 1: Preparation of a Compound Represented by Formula 5-a

As shown in [Scheme 12], a compound represented by Chemical Formula 5-a was prepared.

 [Reaction Scheme 12]

20.0 g (81.27 mmol) of 3-bromo-9H-carbazole and 4.9 g (121.90 mmol) of 60% sodium hydride were added to 300 ml of dimethylformamide, followed by stirring at room temperature for 30 minutes. Then, 26.11 g (97.52 mmol) of chlorodiphenyltriazine was dissolved in 200 ml of dimethylformamide, slowly added dropwise, and stirred for 1 hour. After completion of the reaction, 200 ml of distilled water was added, and after filtration, recrystallized with methylene chloride and acetone to give 24.0 g of the compound represented by the formula (5-a) (yield 62%).

Step 2: Preparation of the compound represented by Formula 5-b

As shown in [Scheme 13], a compound represented by Chemical Formula 5-b was prepared.

 [Reaction Scheme 13]

51.0 g (145.61 mmol) of the compound represented by Chemical Formula 1-b obtained in Step 2 of Preparation Example 1 were dissolved in 510 ml of tetrahydrofuran under a nitrogen stream, stirred at −78 ° C., and 110 ml of 1.6M normal-butyllithium. (175.0 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining at -78 ° C. Then, 21.2 g (203.85 mmol) of trimethyl borate was slowly added dropwise, and then stirred at room temperature for 3 hours. After completion of the reaction, 200 ml of 1M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Then, the mixture was extracted with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and hexane to obtain 26.2 g of a compound represented by Chemical Formula 5-b (yield 57%).

Step 3: Preparation of the compound represented by Formula 5-c

As shown in [Scheme 14], a compound represented by Chemical Formula 5-c was prepared.

 [Reaction Scheme 14]

9.9 g (31.42 mmol) of the compound represented by Chemical Formula 5-a obtained from step 1, 10.0 g (20.95 mmol) of the compound represented by Chemical Formula 5-b obtained from Step 2, 480 mg of tetrakis (triphenylphosphine) palladium (0.4 mmol), potassium carbonate 5.8 g (41.90 mmol), 50 ml of 1,4-dioxane, 50 ml of toluene, and 20 ml of distilled water were added, followed by stirring at 100 ° C for 12 hours. After the completion of the reaction, the temperature was adjusted to room temperature and the crystals were filtered off. The crystals were recrystallized from methylene chloride and acetone to obtain 5.6 g of a compound represented by Chemical Formula 30 (yield 40%).

MS [M] ⁺ 668

< Manufacturing example  6> Preparation of a compound represented by Formula 34

Step 1: Preparation of the Compound of Formula 6-a

As shown in [Scheme 14], a compound represented by Chemical Formula 6-a was prepared.

 [Reaction Scheme 14]

50.0 g (182.4 mmol) of the compound represented by Chemical Formula 1-a obtained from step 1 of Preparation Example 1, 57.2 g (273.56 mmol) of iodobenzene-D5, copper powder 23.2 g (364.75 mmol), and 18-crown-6 After adding 9.6 g (36.48 mmol) and 75.6 g (547.1 mmol) of potassium carbonate in that order, 500 ml of 1,2-dichlorobenzene was added, followed by reflux and stirring at 180 ° C for 1 day. After completion of the reaction, the solution after the high temperature filter was concentrated and subjected to column chromatography with hexane alone to obtain 44.2 g of the compound represented by the formula 6-a (yield 69%).

Step 2: Preparation of the compound represented by Formula 6-b

As shown in [Scheme 15], a compound represented by Chemical Formula 6-b was prepared.

 [Reaction Scheme 15]

44.2 g (124.41 mmol) of the compound represented by Chemical Formula 6-a obtained in step 1 was dissolved in 440 ml of tetrahydrofuran under a stream of nitrogen, stirred at -78 ° C, and 93 ml (149.2 mmol) of 1.6M normal-butyllithium. After slowly dropping, when the dropping was completed, the mixture was stirred for 1 hour while maintaining at -78 ° C. Then, 18.1 g (174.17 mmol) of trimethyl borate was slowly added dropwise, and then stirred at room temperature for 3 hours. After completion of the reaction, 200 ml of 1M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Then, the mixture was extracted with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and hexane to obtain 23.2 g of the compound represented by Chemical Formula 6-b (yield 58%).

Step 3: Preparation of the compound represented by Formula 6-c

As shown in [Scheme 16], a compound represented by Chemical Formula 6-c was prepared.

 [Reaction Scheme 16]

10.0 g (20.95 mmol) of the compound represented by Chemical Formula 5-a obtained from step 1 of Preparation Example 5, 10.1 g (31.42 mmol) of the compound represented by Chemical Formula 6-b obtained from step 2, tetrakis (triphenylphosphate) Pin) palladium 480 mg (0.4 mmol), potassium carbonate 5.8 g (41.90 mmol), 50 ml of 1,4-dioxane, 50 ml of toluene, 20 ml of distilled water, and then stirred at 100 ℃ for 12 hours. After the completion of the reaction, the temperature was adjusted to room temperature and the crystals were filtered off. The crystals were recrystallized from methylene chloride and acetone to obtain 5.2 g of a compound represented by the formula (34) (yield 37%).

MS [M] ^&lt; ⁺ & gt ^; 673

< Manufacturing example  7> Preparation of the compound represented by formula 52

Step 1: Preparation of the Compound of Formula 7-a

As shown in [Scheme 17], a compound represented by Chemical Formula 7-a was prepared.

 [Reaction Scheme 17]

20.0 g (109 mmol) of 2,4,6-trichlorotriazine, 17.1 g (109.0 mmol) of bromobenzene and 2.5 g (2.2 mmol) of tetrakis (triphenylphosphine) palladium, 30.1 g (218.0 mmol) of potassium carbonate Was added to a mixed solvent of 600 ml of tetrahydrafuran, 400 ml of toluene and 400 ml of distilled water, followed by stirring and refluxing for 9 hours. After completion of the reaction, the organic layer was washed with saturated aqueous sodium chloride solution after extraction and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and then recrystallized with toluene to obtain 20.7 g of a compound represented by Chemical Formula 7-a (yield 84%).

Step 2: Preparation of the compound represented by Formula 7-b

As shown in [Scheme 18], a compound represented by Chemical Formula 7-b was prepared.

 [Reaction Scheme 18]

20.7 g (91.56 mmol) of the compound represented by Chemical Formula 7-a obtained from step 1, 20.9 g (91.56 mmol) of dibenzothiophen-4-boronic acid, and 2.1 g (1.8) of tetrakis (triphenylphosphine) palladium mmol) and 25.3 g (183.1 mmol) of potassium carbonate were added to a mixed solvent of 600 ml of tetrahydrafuran, 400 ml of toluene and 400 ml of distilled water, followed by stirring and refluxing for 12 hours. After completion of the reaction, the organic layer was washed with saturated aqueous sodium chloride solution after extraction and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and then recrystallized with methylene chloride and hexane to obtain 23.6 g of a compound represented by Chemical Formula 7-b (yield 69%).

Step 3: Preparation of the compound represented by Formula 7-c

As shown in [Scheme 19], a compound represented by Chemical Formula 7-c was prepared.

 Scheme 19

19.7 g (52.69 mmol) of the compound represented by Chemical Formula 1-a obtained from step 1 of Preparation Example 1 and 3.2 g (79.04 mmol) of 60% sodium hydride were added to 200 ml of dimethylformamide, and then, at room temperature Stir for minutes. Then, 23.6 g (63.23 mmol) of the compound represented by Chemical Formula 7-b obtained in step 2 was dissolved in 150 ml of dimethylformamide, and slowly added dropwise thereto, followed by stirring for 1 hour.

After completion of the reaction, 100 ml of distilled water was added, and after filtration, recrystallized to obtain 16.0 g of the compound represented by the formula (7-c) (yield 50%).

Step 3: Preparation of a Compound Represented by Formula 52

As shown in [Scheme 20], a compound represented by Chemical Formula 52 was prepared.

 [Reaction Scheme 20]

 10.0 g (16.35 mmol) of the compound represented by Chemical Formula 7-c obtained from step 3, 5.8 g (24.53 mmol) of the compound represented by Chemical Formula 2-b obtained from step 2 of Preparation Example 2, tetrakis (triphenylphosphine Palladium was added to 380 mg (0.33 mmol), potassium carbonate 4.5 g (32.7 mmol), 50 ml of 1,4-dioxane, 50 ml of toluene, and 20 ml of distilled water, followed by stirring at 100 ° C for 12 hours. After completion of the reaction, the mixture was extracted using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized with methylene chloride and acetone to obtain 5.1 g of the compound represented by Chemical Formula 52 (yield 46%).

MS [M] ⁺ 724

< Manufacturing example  8> Preparation of the compound represented by Chemical Formula 55

Step 1: Preparation of the Compound of Formula 8-a

As shown in [Scheme 20], a compound represented by Chemical Formula 55 was prepared.

 [Reaction Scheme 20]

10.0 g (16.35 mmol) of the compound represented by Chemical Formula 7-c obtained from step 2 of Preparation Example 7, 8.4 g (19.62 mmol) of (9-phenyl-9H-carbazol-3-yl) boronic acid, tetrakis (Triphenylphosphine) palladium 380 mg (0.33 mmol), potassium carbonate 4.5 g (32.7 mmol), 50 ml of 1,4-dioxane, 50 ml of toluene, 20 ml of distilled water and then stirred at 100 ° C for 12 hours It was. After completion of the reaction, the mixture was extracted using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized with methylene chloride and acetone to obtain 5.4 g of a compound represented by Chemical Formula 55 (yield 43%).

MS [M] ⁺ 774

Example

< Example  1 to 23> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound + Ir (ppy) ₃ (prepared by the present invention) 10%) (300 mW), Alq ₃ (350 mW), LiF (5 mW), and Al (1,000 mW) were formed in this order and measured at 0.4 mA.

[DNTPD]

[NPD]

[Ir (ppy) ₃ ]

[Alq ₃ ]

< Comparative Example  1>

The organic light emitting diode device for the comparative example was manufactured in the same manner except for using CBP instead of the compound prepared by the present invention as a host material in the device structure of the above embodiment.

[CBP]

division Host Dopant Doping concentration% V Cd / m ² CIEx CIEy T ₈₀
(Hr) Comparative Example 1 CBP Ir (ppy) ₃ 10 7.9 3800 0.297 0.624 68 Example 1 5 Ir (ppy) ₃ 10 4.1 5230 0.310 0.620 198 Example 2 6 Ir (ppy) ₃ 10 4.0 5120 0.303 0.623 215 Example 3 7 Ir (ppy) ₃ 10 4.1 5450 0.305 0.626 171 Example 4 8 Ir (ppy) ₃ 10 3.9 5290 0.311 0.624 191 Example 5 30 Ir (ppy) ₃ 10 3.5 5170 0.313 0.620 237 Example 6 34 Ir (ppy) ₃ 10 4.2 5200 0.311 0.622 167 Example 7 52 Ir (ppy) ₃ 10 3.8 5210 0.321 0.623 187 Example 8 55 Ir (ppy) ₃ 10 4.7 5180 0.309 0.622 231 Example 9 2 Ir (ppy) ₃ 10 4.8 4790 0.301 0.621 168 Example 10 3 Ir (ppy) ₃ 10 4.1 4930 0.303 0.620 178 Example 11 4 Ir (ppy) ₃ 10 4.3 5320 0.314 0.625 159 Example 12 14 Ir (ppy) ₃ 10 4.0 5010 0.313 0.626 156 Example 13 18 Ir (ppy) ₃ 10 4.3 4780 0.307 0.624 179 Example 14 53 Ir (ppy) ₃ 10 3.9 4820 0.313 0.620 164 Example 15 74 Ir (ppy) ₃ 10 4.2 5120 0.311 0.622 170 Example 16 93 Ir (ppy) ₃ 10 4.3 4910 0.321 0.623 177 Example 17 101 Ir (ppy) ₃ 10 4.2 4920 0.318 0.623 155 Example 18 115 Ir (ppy) ₃ 10 4.1 5110 0.307 0.624 192 Example 19 116 Ir (ppy) ₃ 10 4.4 4720 0.313 0.620 162 Example 20 119 Ir (ppy) ₃ 10 4.3 4890 0.317 0.622 157 Example 21 129 Ir (ppy) ₃ 10 3.9 5150 0.321 0.620 183 Example 21 131 Ir (ppy) ₃ 10 4.7 4780 0.308 0.622 191 Example 22 132 Ir (ppy) ₃ 10 4.5 4920 0.313 0.621 188 Example 23 136 Ir (ppy) ₃ 10 4.3 5030 0.305 0.624 173

As shown in Table 1, the organic electroluminescent device comprising a heterocyclic compound prepared according to Examples 1 to 23 of the present invention as a host material is CBP (Comparative Example 1) (7.9 V) which is a phosphorescent host material. Compared with the low driving voltage (V) of 3.5 to 4.8 V and excellent luminous efficiency (Cd / ㎡) and long life (T ₈₀ ), it can be usefully used for display device, display device and lighting. Can be.

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 (10)

A heterocyclic compound represented by the following [Formula 1]:
[Chemical Formula 1]

In [Formula 1],
X ₁ to X ₈ are the same as or different from each other, and each independently

Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted carbon number An alkyl group of 1 to 30, a substituted or unsubstituted aryl group of 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 60 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, -SiR ₁ R ₂ R ₃ and -NR ₄ R ₅ &Lt; / RTI &gt;
When X ₁ to X ₈ are each -NR ₄ R ₅ , R ₄ and R ₅ may be bonded to each other to form a ring having 6 to 30 carbon atoms,
R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group Alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or Unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl jade having 5 to 50 carbon atoms A timing, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and a substituted or unsubstituted arylsilyl group having 5 to 50 carbon atoms,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted carbon group having 2 to 30 carbon atoms Heteroaryl group,
L ₁ and L ₂ are the same as or different from each other, and each independently a single bond or a divalent linking group,
When L ₁ and L ₂ are a divalent linking group, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted alky having 2 to 30 carbon atoms. A niylene group, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
n and m are each independently an integer of 0 to 3, when n and m are 2 or more, a plurality of L ₁ and L ₂ are the same or different, and p is an integer of 0 to 3,
X ₁ to X ₈ , L ₁ , L ₂ , Ar ₁ , Ar ₂ And substituents thereof may be linked to adjacent substituents to form a saturated or unsaturated ring. The method of claim 1,
X ₁ to X ₈ is a heterocyclic compound, characterized in that connected to each other or adjacent substituents to form an alicyclic, aromatic monocyclic or polycyclic ring. 3. The method of claim 2,
The heterocyclic, aromatic monocyclic or polycyclic ring carbon atom formed is a heterocyclic compound, characterized in that the alicyclic with any one or more heteroatoms selected from N, S and O. The method of claim 1,
Wherein L ₁ and L ₂ is a heterocyclic compound, characterized in that any one selected from the following [formula A1] to [formula A16]:
[Structural formula A1] [Structural formula A2] [Structural formula A3] [Structural formula A4]

[Structural formula A5] [Structural formula A6] [Structural formula A7] [Structural formula A8]

[Structural formula A9] [Structural formula A10] [Structural formula A11] [Structural formula A12]

[Structural formula A13] [Structural formula A14] [Structural formula A15] [Structural formula A16]

In the above structural formulas A1 to A16, hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each structural formula. The method of claim 1,
X ₁ to X ₈ , L ₁ , L ₂ , Ar ₁ and Ar ₂ are each independently deuterium, cyano group, halogen group, hydroxy group, nitro group, C1-C20 alkyl group, C1-C20 Alkenyl group, C1-C20 alkynyl group, C1-C20 halogenated alkyl group, C5-C24 aryl group, C2-C24 heteroaryl group, C1-C20 alkoxy group, C5-C24 aryl It is further substituted with at least one substituent selected from an oxy group, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 5 to 24 carbon atoms, an alkylamine group having 1 to 20 carbon atoms and an arylamine group having 6 to 24 carbon atoms. With
The heterocyclic compound is characterized in that the substituents are bonded to each other to form a saturated or unsaturated ring. The method of claim 1,
[Formula 1] is a heterocyclic compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 161]:

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

[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] Anode; cathode; And a layer interposed between the anode and the cathode, the layer including a heterocyclic compound represented by [Formula 1] according to claim 1. 8. The method of claim 7,
The heterocyclic compound is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode. 8. The method of claim 7,
Wherein 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 is further interposed between the anode and the cathode. 10. The method of claim 9,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process.

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