KR20150010016A - Organic electroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device. More specifically, the organic electroluminescent device has excellent light emitting efficiency and color purity and is capable of reducing the driving voltage and while being used for an extended period of time. The organic electroluminescent device according to an embodiment of the present invention includes dopant compound of a specific combination and a host compound.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

The present invention relates to an organic electroluminescent device comprising a dopant compound and a host compound.

Among the display elements, electroluminescence devices (EL devices) are self-luminous display devices having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company developed an organic electroluminescent device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

Organic electroluminescent devices can reduce cost and material cost compared to liquid crystal displays (LCDs), have wide viewing angles, excellent contrast ratio, and fast response times. Organic electroluminescent devices have undergone dramatic technological advances that have improved efficiency by more than 80 times and lifetimes by more than 100 times.

In addition, the organic electroluminescent device is advantageous in large-sized display, and a 40-inch organic electroluminescent device panel has been announced, and the size of the organic electroluminescent device is rapidly increasing. However, in order to increase the size, it is necessary to improve the lifetime of the device and increase the luminous efficiency.

In order to improve the lifetime of the organic electroluminescent device, it is necessary to prevent crystallization of the material due to joule heat generated when the device is driven. Therefore, it is necessary to develop organic compounds having excellent electron injection and mobility and high electrochemical stability.

On the other hand, the most important factor determining the luminous efficiency of an organic electroluminescent device is a light emitting material. The light emitting material can be divided into fluorescence using a singlet state exciton and phosphorescent light using a triplet state depending on a light emitting mechanism. Generally, an organic electroluminescent device using phosphorescence has a short life, Widely used.

Further, a host / dopant system can be used as a light emitting material. When only one material is used as the light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuation effect. A host / dopant system is advantageous in terms of increasing color purity and increasing luminescence efficiency and stability through energy transfer.

In the case of blue fluorescent host materials, many materials have been developed and commercialized since 4,4'-bis (2,2'-diphenylvinyl) -1,1'-biphenyl (DPVBi) in Idemitsu Kosan The blue material system of Mitsubosan Corporation, the dinaphthylanthracene system and the tetra (t-butyl) perylene system of Kodak are known, but many researches have been made to develop a blue fluorescent host material which can exhibit better characteristics in the device .

Examples of the fluorescent dopant include an amine compound, an aromatic compound, a chelate complex such as a tris (8-quinolinolate) aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bistyrylarylene derivative, an oxadiazole derivative Can be selected.

On the other hand, when a conventional light emitting material containing a dopant compound and a host compound is applied to an organic electroluminescent device, the organic electroluminescent device has a disadvantage in terms of luminous efficiency, power efficiency, and operating life. Particularly, it has been difficult to obtain a light emitting layer exhibiting blue light emission with excellent lifetime characteristics.

Japanese Patent Registration JP 3148176 B (Mar. 19, 2001)

An object of the present invention is firstly to provide an organic electroluminescent device in which an organic material layer is interposed between a cathode and a cathode on a substrate, wherein the organic material layer comprises an organic electroluminescent device comprising at least one host compound and at least one dopant compound, In addition,

Second, an organic electroluminescent device having excellent luminescent efficiency, excellent color purity, low driving voltage and good driving life is provided.

In order to achieve the above object, the present invention provides an organic electroluminescent device comprising at least one host compound represented by the following general formula (1) and at least one dopant compound represented by the following general formula (2).

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₁₈ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 3 -C 30) cycloalkyl, alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted (C6-C30) unsubstituted (3-30 membered) heteroaryl, -SiR ₃₁ R ₃₂ R _33, cyano or hydroxy, or; R ₁ to R ₅ and R ₁₄ to R ₁₈ may be connected to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring of (3-30 member) An atom may form a spiro structure and the carbon atom of the ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

R ₃₁ to R ₃₃ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted ) Heteroaryl;

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Ar ₁ and Ar ₂ may be connected to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring of (3-30 membered), and the carbon atoms of the ring formed form a spiro structure And the carbon atoms of the ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur provided that Ar ₁ and Ar ₂ are not simultaneously hydrogen;

The heteroaryl includes at least one heteroatom selected from the group consisting of B, N, O, S, P (= O), Si and P.

(2)

In Formula 2,

Ar ₃ is substituted or unsubstituted pyrene;

L is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

Ar ₄ and Ar ₅ are each independently substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered heteroaryl); Ar ₄ and Ar ₅ may be joined together with the nitrogen atom to form a (3-30 membered) substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atoms of the ring formed may be nitrogen, Lt; / RTI > may be replaced by one or more heteroatoms selected from sulfur;

는 동일하거나 상이할 수 있다.
n is an integer of 1 to 3, and when n is 2 or more,

May be the same or different.

The organic electroluminescent device according to the present invention has an advantage of exhibiting excellent luminous efficiency, excellent color purity, low driving voltage and good driving life by containing a combination of a specific dopant compound and a host compound.

The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.

The present invention relates to an organic electroluminescent device comprising at least one host compound represented by the general formula (1) and at least one dopant compound represented by the general formula (2).

The compounds represented by the formulas (1) and (2) will be described in more detail as follows.

Specific examples of the "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Specific examples of the "alkenyl" herein include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. Examples of "alkynyl" herein include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2- Examples of "cycloalkyl" herein include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term " (3-7 member) heterocycloalkyl "as used herein refers to a heterocycloalkyl group having 3 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (= O) Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "aryl" refers to a single ring or fused ring radical derived from an aromatic hydrocarbon and includes, for example, phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, Wherein R is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, fluorine, chlorine, bromine, fluorine, chlorine, bromine, , Crycenyl, naphthacenyl, fluoranthenyl and the like. The term "(3-30) heteroaryl (phenylene)" used herein refers to a heteroaryl group having 3 to 30 ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, P Quot; means an aryl group containing an atom. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Further, in the phrase "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. Substituted (C ₁ -C 30) alkyl, substituted (C 3 -C 30) cycloalkyl, substituted (C ₁ -C 30) alkyl, or substituted (C ₁ -C 30) alkyl in R ₁ to R ₁₈ , R ₃₁ to R ₃₃ , Ar ₁ to Ar ₅ , (C6-C30) aryl, substituted (3-30 membered heteroaryl, substituted pyrene, substituted (C6-C30) arylene and substituted (3-30 membered heteroarylene) substituents are each independently selected from the group consisting of deuterium (C6-C30) alkoxy substituted by halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted by halogen, (C6-C30) aryl (C6-30 aryl), (C6-30 aryl), (3-30 membered heteroaryl, 3-30 membered heteroaryl substituted by (C6-30) aryl, (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl (C1-C30) alkylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Mono or di (C1-C30) alkylamino, (C1-C30) alkylamino, di (C6-C30) arylamino, di- (C1-C30) alkyl, (C6-C30) arylcarbonyl, (C6-C30) aryl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, (C 6 -C 15) aryl, or deuterium optionally substituted with halogen Substituted with (C6-C15) aryl, (5-15) heteroaryl, (5-15) heteroaryl substituted with (C6-C15) aryl, (C6-C15) arylsilyl, tri (C6-C15) arylsilyl, (C1-C6) ) Alkyl (C6-C15) aryl, and hydroxy.

In Formula 1, R ₁ to R ₁₈ are each preferably independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 6 -C 20) Or unsubstituted (5-20 membered) heteroaryl; R ₁ to R ₅ may be connected to adjacent substituents to form a substituted or unsubstituted monovalent or polycyclic alicyclic or aromatic ring of (5-20) atoms, and the ring formed may form a spiro structure ; More preferably each independently is hydrogen, deuterium, halogen, (CrC6) alkyl, (C6-C15) aryl, or (5-15 member) heteroaryl; R ₁ to R ₅ may be connected to adjacent substituents to form a monocyclic or polycyclic alicyclic or aromatic ring substituted or unsubstituted with methyl or phenyl (5-15 membered), and the ring formed may be spirofluorene Structure can be formed.

In the above formula (1), Ar ₁ and Ar ₂ are preferably each independently a substituted or unsubstituted (C 6 -C 20) aryl or a substituted or unsubstituted (5-20) heteroaryl, more preferably (C6-C15) aryl optionally substituted with (C1-C6) alkyl, (C6-C15) aryl, (5-15 membered heteroaryl, or C6-C18) aryl; Or (5-15 membered) heteroaryl which is unsubstituted or substituted by (C6-C15) aryl.

In the above formula (2), Ar ₃ is preferably (C 5 -C 15) aryl substituted with (C 6 -C 15) aryl, (C 6 -C 15) aryl substituted with (5-15 membered) heteroaryl substituted by (C1-C6) alkyl, (C6-C15) aryl or (C1- C6) alkyl.

It is preferable that Ar ₃ is selected from the following structures.

Wherein A is selected from the group consisting of deuterium, halogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkyl substituted by halogen, (C 1 -C 30) alkoxy, (C 6 -C 30) (3-30) heteroaryl substituted with (C6-C30) aryl, (C6-C30) aryl substituted with deuterium, (C6-30) (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, di (C6-C30) alkylamino, mono or di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkylcarbonyl, di (C1-C30) alkylboronyl, Alkyl (C6-C30) aryl, carboxyl, nitro, and hydroxy; m is an integer from 0 to 4, preferably A is (C6-C15) aryl substituted by (C6-C15) aryl, (C6-C15) aryl substituted by 5-15 membered heteroaryl, or (5-15 membered) heteroaryl substituted by (C1-C6) alkyl (C6-C15) aryl.

In Formula 2, L is preferably a single bond or a substituted or unsubstituted (C6-C20) arylene; More preferably a single bond or (C6-C15) arylene substituted or unsubstituted with (C1-C6) alkyl.

In the general formula (2), Ar ₄ and Ar ₅ are preferably each independently substituted or unsubstituted (C 6 -C 20) aryl, or Ar ₄ and Ar ₅ are linked together with a nitrogen atom to form a A substituted or unsubstituted monocyclic or polycyclic alicyclic group or an aromatic ring; (C1-C6) alkoxy, (C6-C15) aryl, tri (C1-C6) alkylsilyl, tri (C6-C15) arylsilyl, (C6-C18) alkylthi (C6-C15) arylsilyl, (C6-C18) arylene substituted or unsubstituted with cyano or hydroxy; Or (C6-C15) aryl, or aryl substituted or unsubstituted (5-15 membered) heterocycloalkyl with, Ar ₄ and Ar ₅ is halogen, cyano, (C1- of connected together with the nitrogen atom (5-15 W) C6) alkyl, or (C6-C15) aryl, or a substituted or unsubstituted polycyclic alicyclic or aromatic ring.

When Ar ₄ and Ar ₅ are linked together with a nitrogen atom to form a ring, the following ring can be formed.

The compound of formula (1) may be more specifically exemplified by the following compounds, but the following compounds do not limit the invention.

The compound of formula (2) may be more specifically exemplified as the following compounds, but the following compounds are not intended to limit the invention.

The compounds of formulas (1) and (2) according to the present invention can be prepared by synthetic methods known in the art. For example, it can be prepared as shown in the following Schemes 1 and 2, and the following production methods do not limit the method of preparing the compounds of the formulas (1) and (2) will be.

Specifically, the organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic compound layer sandwiched between the first electrode and the second electrode, wherein the organic compound layer comprises a light emitting layer, wherein the light emitting layer comprises at least one host compound represented by Formula 1, and 1 ≪ / RTI > combinations of more than two species of dopant compounds.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.

The light emitting layer may be a single layer as a light emitting layer, or may be a plurality of layers in which two or more layers are stacked. At this time, the light emitting layer can also play the role of injection and transport of electrons and holes and light emission. The dopant of the light emitting layer and the host are preferably doped with less than 17 wt% of the dopant.

According to another aspect of the present invention, there is provided a host / dopant combination of at least one host compound represented by Formula 1 and at least one dopant compound represented by Formula 2. The present invention also provides an organic electroluminescent device comprising the host / dopant combination.

The present invention provides, in a further aspect, an organic electroluminescent material comprising a combination of at least one host compound represented by Formula 1 and at least one dopant compound represented by Formula 2, and an organic electroluminescent device comprising the above- to provide. The material may be composed of only the combination of the compound of Formula 1 and the compound of Formula 2, and may further include common materials included in the organic electroluminescent material.

In another aspect, the present invention provides an organic material layer containing a combination of at least one host compound represented by Formula 1 and at least one dopant compound represented by Formula 2. The organic material layer includes a plurality of layers, and the dopant compound and the host compound may be included in the same layer or may be included in different layers, respectively. The present invention also provides an organic electroluminescent device including the organic material layer.

In the organic electroluminescent device of the present invention, the organic layer includes a combination of the host compound represented by the formula (1) and the dopant compound represented by the formula (2), and at the same time, at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound .

In addition, in the organic electroluminescent device of the present invention, in addition to the combination of the host compound represented by the formula (1) and the dopant compound represented by the formula (2) in the organic compound layer, group 1, group 2, group 4, group 5 transition metal, The organic layer may further include at least one light-emitting layer and a charge-generating layer, which are further included.

In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

In the organic electroluminescent device of the present invention, one layer (hereinafter referred to as a "surface layer") of a chalcogenide layer, a metal halide layer and a metal oxide layer is formed on at least one inner surface of a pair of electrodes ) Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO _X (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transport compound and the oxidative dopant, may be disposed on at least one surface of the pair of electrodes thus manufactured desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The formation of each layer of the organic electroluminescent device of the present invention may be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dip coating or flow coating Can be applied.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., And it may be any thing that does not have a problem in the tabernacle.

Hereinafter, for a detailed understanding of the present invention, the compounds according to the present invention, the preparation method thereof and the luminescent characteristics of the device are described for the representative compounds of the present invention, but the present invention is not limited thereto. It is not intended to limit the scope.

[ Example  1] Preparation of compound H-26

Preparation of Compound 1-2

Compound 11 (25 g, 0.157 mol) and HCl (10%, 840 mL) were placed in a flask and stirred at 0 ° C. NaNO ₂ (11.6 g, 0.168 mol) was dissolved in 85 mL of H ₂ O, And stirred at 0 < 0 > C for 20 min. KI (52 g, 0.314 mol) was dissolved in 165 mL of H ₂ O and added to the reaction mixture, which was stirred for 3 hours at 0 ° C. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate (EA). The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator, and the residue was purified by column to obtain Compound 1-2 (10.2 g, 24% .

Preparation of compounds 1-4

Compound 1-2 (9.2 g, 0.034 mol) is put into a flask, compound 1-3 (11 g, 0.037 mol) , Pd (PPh 3) 4 (2.0 g, 0.001 mol), K 2 CO 3 (2 M, 51 mL), 51 mL of EtOH and 100 mL of toluene were added, and then the reaction mixture was heated to 120 DEG C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The organic layer was purified by column to obtain Compound 1-4 (9.5 g, 70%).

Preparation of compounds 1-5

Compound 1-4 (9.5 g, 0.024 mol) and 200 mL of MC were placed in a flask and the reaction mixture was stirred at 0 ° C for 20 minutes before triethylamine (10 mL, 0.072 mol) was added to the reaction mixture. Then, trifluoromethanesulfonic anhydride (OTf ₂ ) (5.1 mL, 0.031 mol) was added to the mixture and stirred at room temperature for 6 hours. After the reaction was completed, 4 M HCl was added to the mixture, and the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , the solvent was removed using a rotary evaporator, , 63%).

compound H-26 Manufacturing

Compound 1-5 (8.0 g, 0.015 mol) were placed in the flask, the compound 1-6 (2.0 g, 0.016 mol) , Pd (PPh 3) 4 (1.0 g, 0.001 mol), K 2 CO 3 (2 M, 22 mL), EtOH (22 mL) and toluene (50 mL) were added and the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , the solvent was removed using a rotary evaporator, and the residue was purified by column to obtain 3.1 g (45%) of compound H-26 .

[ Example  2] Preparation of compound H-47

Compound 2-1 (2.7 g, 0.007 mol), Pd (PPh ₃ ) ₄ (465 mg, 0.0004 mol), K ₂ CO ₃ (0.007 mol) were added to a flask in the same manner as in Example 1 2 M, 11 mL), 11 mL EtOH and 22 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to obtain a compound H-47 (3.3 g, 78%).

[ Example  3] Preparation of compound H-48

Examples of the compound 1 1-5 (3.7 g, 0.006 mol ) were placed in the flask, the compound 3-1 (1.3 g, 0.006 mol) , Pd (PPh 3) 4 (350 mg, 0.0003 mol), K 2 CO 3 ( 2 M, 10 mL), 10 mL EtOH and 20 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure to obtain a compound H-48 (1.8 g, 48%).

[ Example  4] Production of compound H-45

Compound 4-1 (1.6 g, 0.008 mol), Pd (PPh ₃ ) ₄ (462 mg, 0.0004 mol) and K ₂ CO ₃ (0.005 mol) were added to a flask. 2 M, 11 mL), 11 mL EtOH and 22 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off to obtain a compound H-45 (1.7 g, 43%).

[ Example  5] Preparation of compound H-49

Compound 5-1 (1.5 g, 0.006 mol), Pd (PPh ₃ ) ₄ (330 mg, 0.0002 mol), K ₂ CO ₃ (0.005 mol) were added to a flask. 2 M, 9 mL), EtOH (9 mL) and toluene (22 mL) were added and the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to obtain a compound H-49 (2.0 g, 60%).

[ Example  6] Preparation of compound H-1

Compound 6-1 into a (5.4 g, 0.010 mol) in a flask compound 1-6 (1.4 g, 0.011 mol) , Pd (PPh 3) 4 (580 mg, 0.0005 mol), K 2 CO 3 (2 M, 15 mL), 15 mL of EtOH and 30 mL of toluene were added, and then the reaction mixture was heated to 120 DEG C and stirred for 8 hours. After the reaction was completed, the mixture was rinsed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed by a rotary evaporator. The solvent was distilled off to obtain a compound H-1 (3.3 g, 73%).

[ Example  7] Preparation of compound H-19

Compound 4-1 (1.6 g, 0.008 mol), Pd (PPh ₃ ) ₄ (462 mg, 0.0004 mol) and K ₂ CO ₃ (0.004 mol) were placed in a flask. 2 M, 11 mL), 11 mL EtOH and 22 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to obtain Compound H-19 (2.7 g, 67%).

[ Example  8] Preparation of compound H-20

Example 6 Compound 6-1 (3.0 g, 0.005 mol) were placed in the flask of the compound 5-1 (1.8 g, 0.008 mol), Pd (PPh 3) 4 (330 mg, 0.0003 mol), K 2 CO 3 ( 2 M, 10 mL), 10 mL EtOH and 20 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off to obtain a compound H-20 (1.5 g, 47%).

[ Example  9] Preparation of compound H-21

Compound 2-1 (2.2 g, 0.006 mol), Pd (PPh ₃ ) ₄ (346 mg, 0.0003 mol) and K ₂ CO ₃ (0.005 mol) were placed in a flask. 2 M, 10 mL), 10 mL EtOH and 20 mL toluene, the reaction mixture was heated to 120 < 0 > C and stirred for 8 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off to obtain a compound H-21 (2.2 g, 65%).

[ Example  10] Preparation of compound D-8

(5 g, 13.8 mmol), diphenylamine (5.8 g, 34.2 mmol), Pd (OAc) ₂ (0.16 g, 0.71 mmol) and NaOtBu (6.7 g, 69.7 mmol) were mixed with 1,6-dibromopyran After that, it was made into a vacuum state and a nitrogen atmosphere state. To the reaction mixture, P (t-Bu) ₃ (1 mL, 2.0 mmol) and toluene (80 mL) were added and the mixture was refluxed at 120 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with EA and distilled water, and recrystallized with EA / MeOH to obtain 2.5 g (9.3 mmol, 30%) of compound D-8 .

[ Example  11] Preparation of compound D-9

Compound D-9 was synthesized in the same manner as compound D-8 using 1,6-dibromopyrene and 4- (phenylamino) benzonitrile to obtain 4 g (yield: 50%).

[ Example  12] Preparation of compound D-10

Compound D-10 was synthesized in the same manner as Compound D-8 using 6-bromo-N, N-diphenylpyran-1 -amine and N-phenyl-4- (triphenylsilyl) aniline to give 5.6 g Yield: 40%).

[ Example  13] Preparation of compound D-21

A flask 1,6-di-bromo fur Len (13 g, 0.068 mol), 4- ( phenylamino) benzonitrile (52 g, 0.144 mol), Cu (7.6 g, 0.12 mol), Cs 2 CO 3 (54 g , 0.167 mol) and 18-Crown-6 (2.1 g, 0.008 mol) were dissolved in 300 mL of 1,2-dichlorobenzene, and the mixture was refluxed and stirred at 190 ° C for 12 hours. After the reaction was completed, the 1,2-dichlorobenzene was removed by a distillation apparatus, and the organic layer was extracted with EA. After removing residual water using magnesium sulfate, the product was separated into a column to obtain Compound 6-1 (15.5 g, 50%) .

The compound obtained in flasks 6-1 (6 g, 0.012 mol) , 3- (9H- carbazol-9-yl) phenylboronic acid (5.4 g, 0.019 mol), Pd (PPh 3) 4 (732 mg, 0.63 mmol ) And K ₂ CO ₃ (5.2 g, 0.036 mol) were dissolved in 40 mL of toluene, 20 mL of EtOH and 20 mL of H ₂ O, and the mixture was stirred at 120 ° C for 7 hours. After the reaction was terminated by slowly adding H ₂ O, the organic layer was extracted with EA, and the residue was dried with magnesium sulfate, dried and separated into a column to obtain a compound D-21 (4 g, 50%).

[ Example  14] Preparation of compound D-25

Compound D-25 was synthesized in the same manner as Compound D-21 , using Compound 6-1 and 9-phenyl-9H-carbazole-3-ylboronic acid to give 1.9 g (Yield: 30%).

[ Example  15] Preparation of compound D-32

T-butylphosphine (0.7 mL, 2.8 mmol), palladium acetate (318 mg, 1.4 mmol), 1,6-dibromopyran (10 g, 27.8 mmol), indoline And cesium carbonate (27 g, 83.3 mmol) were dissolved in toluene and refluxed at 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with EA and washed with distilled water. Dried over magnesium sulfate and distilled under reduced pressure. The column was separated to obtain a compound D-32 (5 g, 41%).

[ Example  16] Preparation of compound D-88

Preparation of Compound 16-1

3-amino-benzonitrile (50 g, 423 mmol), iodo-benzene (39 mL, 352 mmol), palladium (II) acetate _{(Pd (OAc) 2) 3.9} g, tree -t- butylphosphine (P (t -Bu) ₃ ) and 228 g of Cs ₂ CO ₃ were added to 1000 mL of toluene, and the mixture was stirred at 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was slowly cooled to room temperature, and H ₂ O was added thereto, followed by extraction with EA. The organic layer was dried over Na ₂ SO ₄ , concentrated, and then subjected to column separation to obtain Compound 16-1 (70 g, 85%).

Preparation of Compound 16-2

Dibromophene (30 g, 83 mmol), Cu (4.8 g) and Cs ₂ CO _{3 (} 34 g) were added to 400 mL of 1,2-dichlorobenzene, and 200 Lt; 0 > C for 19 hours. After completion of the stirring, H ₂ O was slowly added to terminate the reaction. The reaction mixture was cooled to room temperature, and H ₂ O was added thereto and extracted with EA. The organic layer was dried with Na ₂ SO ₄ concentrated and the separation column to obtain the title compound 16-2 (12 g, 60%) .

compound D-88 Manufacturing

Compound 16-2 (5 g, 10 mmol) and 1.6 mL of 1,2,3,4-tetrahydroquinoline were mixed and the compound D-88 (3.8 g, 69%) was obtained in the same manner as the compound 16-1, ≪ / RTI >

[ Example  17] Preparation of compound D-149

Preparation of Compound 17-1

4-Isobutyrylbenzonitrile (6.2 g, 35.7 mmol) and phenylhydrazine (3.8 g, 35.7 mmol) were added to 120 mL of acetic acid and stirred at 80 ° C for 3 hours. After cooling the mixture, 120 mL of 1,2-dichloroethane was added, and sodium triacetoxyborohydride (NaBH (OAc) ₃ ) (9.8 g, 46.6 mmol) was added little by little. After stirring at room temperature for 30 minutes, H ₂ O was added and extracted with EA. The organic layer is dried over Na ₂ SO ₄ and concentrated, and the separation column to yield the compound 17-1 (5.3 g, 60%) .

compound D-149 Manufacturing

Compound 16-2 (5 g, 10 mmol) and compound 17-1 (2.5 g, 20 mmol) were mixed and compound D-149 (4.5 g, 70%) was obtained in the same manner as for the synthesis of compound 16-1.

[ Example  18] Preparation of compound D-98

Preparation of Compound 18-1

2,4-di-bromo-6-fluoro-aniline to the parent (25g, 92.9 mmol), phenylboronic acid (34 g, 278 mmol), tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (10 g, 9.29 mmol) and K ₂ CO ₃ (64 g, 464 mmol) were dissolved in a mixed solution of 300 mL of toluene, 100 mL of ethanol (EtOH) and 100 mL of H ₂ O and the mixture was stirred at 120 ° C. for 7 hours. After the reaction, H ₂ O was added slowly to terminate the reaction. The organic layer was extracted with EA, dried over Na ₂ SO ₄ , and then separated into a column to obtain Compound 18-1 (20 g).

Preparation of Compound 18-2

Compound 18-2 (23 g, 72%) was obtained in the same manner as the compound 16-1 using the compound 18-1 (30 g, 113.9 mmol) and iodobenzene (19.3 g, 94 mmol).

Preparation of Compound 18-3

Compound 18-3 (2.2 g, 12%) was obtained in the same manner as the compound 16-2 using compound 18-2 (10 g, 29.4 mmol) and 1,6-dibromopyrene (21 g, ).

compound D-98 Manufacturing

Compound D-98 (1 g, 43%) was obtained in the same manner as in the synthesis of the compound D-88, using the compound 18-3 (5 g, 8 mmol) and indoline (1 mL, 9.6 mmol).

[ Example  19] Preparation of compound D-153

Compound 19-3 (5 g, 8 mmol) and 1,2,3,4-tetrahydro-6-carbonitrile (1.5 g, 9.6 mmol) by using the compound in the same manner as in Synthesis of Compound D-88 D -153 (1 g, 40%).

[ Example  20] Preparation of compound D-147

Preparation of Compound 20-1

Compound 20-1 (4 g, 60%) was reacted with Compound A (3 g, 8.6 mmol) and 1,6-dibromopyrrene (6.2 g, 17.2 mmol) in the same manner as in the synthesis of Compound 16-2 .

compound D-147 Manufacturing

Compound 20-1 (4 g, 6.4 mmol) and 1,2,3,4-tetrahydro-6-carbonitrile (1.2 g, 7.7 mmol) by using the compound in the same manner as in Synthesis of Compound 16-1 D -147 (2.2 g, 50%).

[ Example  21] Preparation of compound D-148

148 (2 g, 50%) was prepared in the same manner as the compound 16-1 using the compound 21-2 (6 g, 12.6 mmol) and 2-phenyl-1H-indole (3 g, 15.2 mmol) ≪ / RTI >

[ Example  22] Preparation of compound D-150

Preparation of Compound 22-1

Compound 12-1 (12 g, 10 mmol) was treated in the same manner as the compound 17-1 using 2-methyl-1-phenylpropan-l-one (15.7 mL, 104 mmol) and phenylhydrazine (15 g, 52%).

Preparation of Compound 22-2

Compound 22-2 (10.6 g, 50%) was obtained in the same manner as in the synthesis of compound 16-2, using diphenylamine (8 g, 47.3 mmol) and 1,6-dibromopyrene (34 g, 94.6 mmol) ≪ / RTI >

compound D-150 Manufacturing

Compound D-150 (12 g, 52%) was obtained in the same manner as the compound 16-1 using the compound 22-1 (3.1 g, 13.9 mmol) and the compound 22-2 (7.5 g, 16.7 mmol).

[ Example  23] Preparation of compound D-144

Compound D-144 (1.5 g, 20%) was obtained in the same manner as the compound 16-1 using the compound 22-1 (3.1 g, 13.9 mmol) and the compound 16-2 (6 g, 12.7 mmol).

[ Example  24] Preparation of compound D-143

Preparation of Compound 24-1

1-one (15 g, 101 mmol) and p-cyanophenylhydrazine (17.1 g, 101 mmol) in the same manner as in the synthesis of the compound 17-1, the compound 24-1 (7.5 g, 30%).

compound D-143 Manufacturing

Compound D-143 (1.25 g, 20%) was obtained in the same manner as the compound 16-1 using the compound 24-1 (2.5 g, 10.1 mmol) and the compound 16-2 (5 g, 10.6 mmol).

[ Example  25] Preparation of compound D-164

Compound 16-2 (6.3 g, 13.3 mmol) and 1,2,3,4-tetrahydro-6-carbonitrile (2 g, 12.6 mmol) to give the compound in the same manner as in the synthesis of compound 16-1, using the D -164 (5.4 g, 78%).

Host compounds H-1 to H-62 and dopant compounds D-1 to D-184 for organic electroluminescent devices were prepared using the methods of Examples 1 to 25, and the dopant compounds Yield (%), MS / EIMS, UV (nm) and PL (nm).

[Table 1]

[device Manufacturing example  1] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device having a structure using the light emitting material of the present invention was prepared. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N ¹ , N ^{1 '} - ([1,1'-biphenyl] -4,4'-diyl) bis ¹ - (naphthalene- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. And evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'-diamine was added to another cell in the vacuum vapor deposition apparatus, Lt; RTI ID = 0.0 > 20 nm < / RTI > A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The compound H-26 of the present invention was added as a host to one cell in a vacuum vapor deposition apparatus and the compound D-9 of the present invention was added as a dopant to another cell. Then, the two substances were evaporated at different rates, A light emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping the dopant in an amount of 3 wt%. Then, 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H- benzo [d] imidazole was placed in one cell on the above- The other cells were charged with lithium quinolate, and then the two materials were evaporated at different rates to deposit an electron transport layer of 30 nm by doping another material for one material in an amount of 30 to 70 wt%. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to produce an OLED device. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

As a result, a current of 72.2 mA / cm < ² > flowed and blue light emission of 2020 cd / m < ² > The half-time was 169 hours.

[device Manufacturing example  2] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was produced in the same manner as in the Device Production Example 1 except that H-1 was used as a host material and D-9 was used as a dopant.

As a result, a current of 73.9 mA / cm < ² > flowed and blue light emission of 2020 cd / m < ² > was confirmed. The half-time was 162 hours.

[device Manufacturing example  3] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that H-45 was used as a host material and D-9 was used as a dopant.

As a result, a current of 76.2 mA / cm < ² > flowed and blue light emission of 2020 cd / m < ² > The half-time was 165 hours.

[device Manufacturing example  4] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was produced in the same manner as in the Device Production Example 1 except that H-49 was used as a host material and D-9 was used as a dopant.

As a result, a current of 77.2 mA / cm < ² > flowed and blue light emission of 2140 cd / m < ² > The half-time was 164 hours.

[device Manufacturing example  5] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that H-48 was used as a host material and D-9 was used as a dopant.

As a result, a current of 73.6 mA / cm < ² > flowed and blue luminescence of 1890 cd / m < ² > was confirmed. The half-life time was 170 hours.

[device Manufacturing example  6] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that H-20 was used as a host material and D-9 was used as a dopant.

As a result, a current of 72.1 mA / cm < ² > flowed and blue light emission of 1890 cd / m < ² > The half-time was 178 hours.

[ Comparative Example  1] Using conventional light emitting materials OLED  Device Manufacturing

An OLED device was prepared in the same manner as in the Device Production Example 1 except that the following compound R-1 was used as a host material and D-9 was used as a dopant.

As a result, a current of 67.6 mA / cm < ² > flowed and blue light emission of 1890 cd / m < ² > was confirmed. The half-time was 146 hours.

As described above, it can be confirmed that the organic electroluminescent device including the combination of the host and the dopant according to the present invention exhibits improved lifetime characteristics while maintaining excellent current characteristics.

Claims (8)

1. An organic electroluminescent device comprising at least one host compound represented by the following formula (1) and at least one dopant compound represented by the following formula (2).
[Chemical Formula 1]

In Formula 1,
R ₁ to R ₁₈ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 3 -C 30) cycloalkyl, alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted (C6-C30) unsubstituted (3-30 membered) heteroaryl, -SiR ₃₁ R ₃₂ R _33, cyano or hydroxy, or; R ₁ to R ₅ and R ₁₄ to R ₁₈ may be connected to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring of (3-30 member) An atom may form a spiro structure and the carbon atom of the ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R ₃₁ to R ₃₃ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted ) Heteroaryl;
Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Ar ₁ and Ar ₂ may be connected to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring of (3-30 membered), and the carbon atoms of the ring formed form a spiro structure And the carbon atoms of the ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur provided that Ar ₁ and Ar ₂ are not simultaneously hydrogen;
The heteroaryl comprises at least one heteroatom selected from the group consisting of B, N, O, S, P (= O), Si and P.

(2)

In Formula 2,
Ar ₃ is substituted or unsubstituted pyrene;
L is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
Ar ₄ and Ar ₅ are each independently substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered heteroaryl); Ar ₄ and Ar ₅ may be joined together with the nitrogen atom to form a (3-30 membered) substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atoms of the ring formed may be nitrogen, Lt; / RTI > may be replaced by one or more heteroatoms selected from sulfur;
n is an integer of 1 to 3, and when n is 2 or more,

May be the same or different.
The method according to claim 1,
Substituted (C ₁ -C 30) alkyl, substituted (C 3 -C 30) cycloalkyl, substituted (C ₁ -C 30) alkyl, or substituted (C ₁ -C 30) alkyl in R ₁ to R ₁₈ , R ₃₁ to R ₃₃ , Ar ₁ to Ar ₅ , (C6-C30) aryl, substituted (3-30 membered heteroaryl, substituted pyrene, substituted (C6-C30) arylene and substituted (3-30 membered heteroarylene) substituents are each independently selected from the group consisting of deuterium (C6-C30) alkoxy substituted by halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted by halogen, (C6-C30) aryl (C6-30 aryl), (C6-30 aryl), (3-30 membered heteroaryl, 3-30 membered heteroaryl substituted by (C6-30) aryl, (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl (C1-C30) alkylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Mono or di (C1-C30) alkylamino, (C1-C30) alkylamino, di (C6-C30) arylamino, di- (C1-C30) alkyl, (C6-C30) arylcarbonyl, (C6-C30) aryl Wherein the organic electroluminescent element is at least one selected from the group consisting of organic electroluminescent elements.
The method of claim 1, wherein in Formula 1 R ₁ to R ₁₈ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C20) aryl, or Substituted or unsubstituted (5-20 membered) heteroaryl; R ₁ to R ₅ may be connected to adjacent substituents to form a substituted or unsubstituted monovalent or polycyclic alicyclic or aromatic ring of (5-20) atoms, and the ring formed may form a spiro structure ;
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C20) aryl, or a substituted or unsubstituted (5-20 membered) heteroaryl.
2. The compound according to claim 1, wherein Ar ₃ in the formula (2) is (5- (C 1 -C 6) alkyl) (5-15 membered) heteroaryl substituted with (C1-C6) alkyl, (C6-C15) aryl, (C1-C6) alkyl or
L is a single bond, or a substituted or unsubstituted (C6-C20) arylene;
Ar ₄ and Ar ₅ are each independently substituted or unsubstituted (C 6 -C 20) aryl, or Ar ₄ and Ar ₅ are connected together with the nitrogen atom to form a substituted or unsubstituted monocyclic or polycyclic An alicyclic group or an aromatic ring of a ring.
The organic electroluminescent device according to claim 1, wherein Ar ₃ in Formula 2 is selected from the following structures.

Wherein A is substituted by deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted by halogen, (C1- C30) alkoxy, (C6-C30) aryl, (C6-C30) aryl substituted by deuterium, (3-30) heteroaryl, (3-30) heteroaryl substituted by (C6- (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-30) (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, di (C6-C30) arylboronyl (C1-C30) alkylamino, mono- or di (C1-C30) alkylcarbonyl, (C1-C30) alkylcarbonyl, (C1-C30) alkylcarbamoyl, C30) aryl, carboxyl, nitro, and hydroxy;
m is an integer of 0 to 4;
2. The organic electroluminescent device according to claim 1, wherein Ar < ₄ > and Ar < ₅ > in the formula (2) together with the nitrogen atom form a ring selected from the following structures.

The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is selected from the following structures.

The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 2 is selected from the following structures.