KR101390616B1 - Novel compounds and organic electro luminescence device using the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device using the same. Specifically, benzothienopyridine and a fused heterocyclic moiety are linked to form a basic skeleton, and various substituents are formed on the basic skeleton. By including the combined new compound and the compound in at least one organic material layer, it is possible to provide an organic EL device having improved efficiency, lifespan, and stability.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

TECHNICAL FIELD The present invention relates to a novel compound and an organic electroluminescent device including the same and more particularly to a compound used in an organic material layer of an organic electroluminescent device.

A study on the electroluminescent (EL) devices that led to the blue electroluminescence using the anthracene single crystal in 1965 based on the observation of the organic thin film emission of the Bernanose in the 1950s was carried out by Tang in 1987, An organic electroluminescent device having a laminated structure divided by functional layers has been proposed. In order to improve the efficiency and lifetime of the organic electroluminescent device, the organic electroluminescent device has been developed to introduce characteristic organic layers in the device.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, so that the phosphorescent dopant as well as the phosphorescent host have been studied.

To date, NPB, BCP, Alq _3, and the like are widely used as materials for the hole transport layer, the hole blocking layer, and the electron transport layer, and anthracene derivatives are used as the light emitting material. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having great advantages in terms of efficiency improvement of light emitting materials are blue, green, red phosphorescent dopant materials, CBP is used as a phosphorescent host material.

However, since conventional luminescent materials have good luminescence characteristics, they have low glass transition temperature and are not very satisfactory in terms of the lifetime of the organic electroluminescent devices because of their poor thermal stability, development of luminescent materials having excellent performance is required .

In order to solve the above problems, it is an object of the present invention to provide a novel compound that can improve the efficiency, lifespan and stability of the organic electroluminescent device.

Another object of the present invention is to provide an organic electroluminescent device using the novel compound.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

In Formula 1,

Ar ₁ is a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₆ -C ₄₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted A substituted C ₃ to C ₄₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group;

R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, Substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₆ to C ₄₀ Arylalkyl group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted C ₃ -C ₄₀ heterocycloalkyl group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, and substituted or is selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C _40, wherein these adjacent groups condensed (fused) to form a ring or also It is not formed, and;

Provided that at least one of R ₁ to R ₈ forms an fused ring represented by Formula 2 with an adjacent group;

In Formula 2,

X ₁ to X ₄ are the same as or different from each other, and are each independently selected from CR ₉ , N, wherein at least one of X ₁ to X ₄ is N;

R ₉ are the same as or different from each other even though they are the same, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted A substituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₆ to C ₄₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted C ₃ -C ₄₀ heterocycloalkyl group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, And substituted or unsubstituted C ₆ -C ₄₀ arylsilyl groups, where they are condensed with adjacent groups Forming or not forming a ring,

In R ₁ to R ₉ , and Ar ₁ , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, Nuclear atom number 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₆ to C ₄₀ arylalkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, and C ₆ to C ₄₀ arylsilyl group are each independently deuterium, halogen, cyano group, C _1- C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryl Oxy group, C ₁ -C ₄₀ alkyloxy group, C ₆ -C ₄₀ arylamine group, C ₆ -C ₄₀ aryl group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nucleus atoms in the group consisting of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, and a C ₆ ~ C ₄₀ aryl group in the silyl Substituted with one or more substituents selected, or is unsubstituted.

The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer Provides an organic electroluminescent device comprising at least one compound represented by the formula (1).

When the compound represented by Chemical Formula 1 of the present invention is used as a light emitting material of an organic light emitting device, it can be greatly improved in terms of light emitting performance, driving voltage, lifespan, efficiency, etc. of the organic light emitting device as compared to the conventional light emitting material. It can be effectively applied to a full color display panel.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention is a benzothienopyridine and a fused heterocyclic moiety is linked to form a basic skeleton, and a structure in which various substituents are bonded to the basic skeleton, wherein Formula 1 (hereinafter, ' Compound I '). As a result, it is possible to improve the phosphorescence characteristics of the device and improve the electron and / or hole transporting ability, luminous efficiency, driving voltage, lifetime characteristics, and the like. And the like.

The pyridothian carbazole skeleton of the present invention in which an indole structure is introduced into benzothienopyridine has a bipolar characteristic according to substituents, so that the balance between hole and electron mobility is achieved. It is expected to exhibit excellent properties at.

In particular, in the basic skeleton in which the indole structure is introduced into benzocyanopyridine, various aromatic ring substituents are introduced to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature (Tg), thereby improving the conventional CBP. It can have high thermal stability. Accordingly, the organic electroluminescent device comprising the compound represented by Formula 1 of the present invention can greatly improve the durability and lifetime characteristics.

In addition, when the compound represented by Formula 1 of the present invention is adopted as a hole injection / transport layer, blue, green, and / or red phosphorescent host material of an organic EL device, the compound having an excellent efficiency and lifespan will be superior to conventional CBP. Can be. Therefore, the compounds according to the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device.

In the above R ₁ to R ₉ and Ar _1, a C ₁ ~ with a substituent in which the term is described of "substituted or unsubstituted", for example C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the Alkynyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ aryl Amine group, C ₆ -C ₄₀ arylalkyl group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, and C ₆ -C ₄₀ arylsilyl Groups may be introduced independently of each other a plurality of substituents the same or different. Non-limiting examples of such substituents include deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ of the C ₄₀ of the alkyloxy group, an arylamine group of C ₆ ~ C _40, C ₆ ~ C ₄₀ aryl group, C alkyl group of ₁ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, and a C ₆ ~ C ₄₀ group consisting arylsilyl of One or more types selected from can be used.

In the compound represented by Formula 1 according to the present invention, Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, and is preferably a substituted or unsubstituted C ₆ ~ selected from the group consisting of C ₄₀ aryl silyl.

For example, in the Ar ₁ of the present invention, the C ₆ ~ C ₄₀ aryl group or a heteroaryl group having 5 to 40 nuclear atoms, phenyl, naphthyl, indene, anthracene, phenanthrene, pyrene, triphenylene, pyridine, Pyrimidine, pyrazine, triazine, quinoline, isoquinoline, quinoxaline, fluorene, carbazole, dibenzothiophene, dibenzofuran, acridine, indole, benzofuran, benzothiophene, benzimidazole, benzothiophene Azole, purine, phenanthroline.

And R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₆ -C ₄₀ An aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, and It is preferably selected from the group consisting of a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group.

R ₁ to R ₉ and Ar _{1, which} are substituents of the compound of formula 1 according to the present invention, may each independently be selected from the following substituent (functional group) groups, for example S1 to S138. However, it is not limited thereto.

The compound represented by the formula (1) according to the present invention may be more specified as a compound of any one of the following formula (3) to (8).

Where

X ₁ to X ₄ , R ₁ to R ₉ and Ar ₁ are the same as defined in the formula (1).

As described above, Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C ₆ ~ C ₄₀ It is preferably selected from the group consisting of an arylamine group and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, and a double-substituted or unsubstituted C ₆ -C ₄₀ aryl group, a substituted or unsubstituted nuclear atom. More preferred are heteroaryl groups of 5 to 40 carbon atoms.

And R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₆ -C ₄₀ Aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group and substituted Or an unsubstituted C ₆ -C ₄₀ arylsilyl group.

Compounds represented by the formula (3) to formula (8) according to the present invention can be more specifically represented by the following formula C-1 to C-24.

Where

R ₁ to R ₉ and Ar ₁ are as defined in the above formula (1).

Meanwhile, when X ₁ to X ₄ in the exemplified compounds are CR ₉ , each R ₉ may be fused with an adjacent R ₉ to form a ring.

As used herein, "unsubstituted alkyl" is a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like. Include.

"Unsubstituted aryl" means an aromatic moiety having 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached to each other in a pendant or fused form to each other.

"Unsubstituted heteroaryl" means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. It is interpreted that two or more rings may be attached to each other in a pendant or fused form to each other and further include a condensed form with an aryl group.

"Fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

The compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

The compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

<Organic Field  Light emitting element>

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device according to the present invention comprises (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, wherein the one or more organic material layers At least one is characterized in that it comprises any one of the compounds represented by the formula (1).

Herein, the organic material layer including the compound represented by Chemical Formula 1 may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Specifically, the organic material layer is preferably a hole transporting layer, a light emitting layer, or an electron transporting layer, more preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device according to the present invention may contain a host material, wherein any one of the compounds represented by Formula 1 may be used as the host material. As such, when the light emitting layer contains any one of the compounds represented by Chemical Formula 1, organic electroluminescence having excellent efficiency (light emitting efficiency and power efficiency), lifetime, luminance, driving voltage, etc., because the bonding force between holes and electrons in the light emitting layer is increased. An element can be provided. The compound represented by Formula 1 may be included in an organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic EL device according to the present invention is not particularly limited, but non-limiting examples thereof may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. . Here, the electron injection layer may be further stacked on the electron transport layer.

In addition, the organic electroluminescent device according to the present invention may not only have a structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked, but also have a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

Examples of the material usable as the anode included in the organic electroluminescent device according to the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black.

Examples of materials usable as a cathode included in the organic electroluminescent device according to the present invention include, but are not limited to, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, Tin, or lead, or alloys thereof; And a multilayer structure material such as LiF / Al or LiO ₂ / Al.

In addition, the organic material layer included in the organic electroluminescent device according to the present invention is a material known in the art, except for using any one of the compounds represented by the formula (1) in the light emitting layer, hole transport layer or electron transport layer Can be done.

Materials that can be used as the substrate included in the organic electroluminescent device according to the present invention are not particularly limited, but examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

Such an organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art. In this case, the light emitting layer included in the organic material layer may be formed by a vacuum deposition method or a solution coating method. Here, examples of the solution coating method include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of SC-1

<Step 1> 2- chloro- 3- (2- chloropyridin- 3- yl ) -9H- carbazole Synthesis of

200 ml / with 6.23 g (39.6 mmol) of 2-chloropyridin-3-ylboronic acid, 11.10 g (39.6 mmol) of 3-bromo-2-chloro-9H-carbazole, 4.75 g (118.8 mmol) under nitrogen stream 100 ml of THF / H ₂ O was added thereto and stirred. 1.15 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 5.33 g (yield: 43%) of 2-chloro-3- (2-chloropyridin-3-yl) -9H-carbazole as a target compound was obtained by using column chromatography.

¹ H-NMR: δ 7.30 (t, 1H), 7.54 (m, 3H), 7.78 (m, 2H), 8.24 (m, 3H), 10.42 (s, 1H)

<Step 2> Synthesis of ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate

15.22 g (48.6 mmol) of 2-chloro-3- (2-chloropyridin-3-yl) -9H-carbazole, 7.17 g (53.54 mmol) of ethyl 3-mercaptopropanoate, 334 mg (0.36 mmol) of Pd under nitrogen stream ₂ dba ₃ , 393 mg (0.73 mmol) of dpephos and 16.8 g (122 mmol) of K ₂ CO ₃ were added to 200 ml of Toluene and stirred at 110 ° C. for 15 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 16.58 g (yield: 83%) of the target compound ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate was removed by removing the solvent of the filtered organic layer using column chromatography. ) Was obtained.

¹ H-NMR: δ 1.22 (t, 3H), 2.51 (t, 2H), 3.02 (t, 2H), 4.09 (q, 2H), 7.17 (m, 1H), 7.30 (m, 1H), 7.54 ( m, 3H), 7.80 (m, 2H), 8.20 (m, 2H), 10.52 (s, 1H)

Step 3 Synthesis of SC-1

19.03 g (46.3 mmol) of ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate, 7.80 g (69.50 mmol) of potassium tert-butoxide under nitrogen stream Put into ml of THF and stirred for 8 hours at 50 ℃. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain 9.77 g (yield: 77%) of the target compound SC-1.

¹ H-NMR: δ 7.32 (m, 2H), 7.55 (m, 2H), 7.80 (m, 2H), 8.10 (m, 1H), 8.60 (m, 2H), 10.51 (s, 1H)

Preparation Example 2 Synthesis of SC-2

<Step 1> Synthesis of 2-chloro-3- (2,6-dichloropyridin-3-yl) -9H-carbazole

Except for using 2,6-dichloropyridin-3-ylboronic acid instead of 2-chloropyridin-3-ylboronic acid, 2-chloro-3- (2 , 6-dichloropyridin-3-yl) -9H-carbazole was obtained.

¹ H-NMR: δ 7.30 (t, 1H), 7.51 (m, 2H), 7.68 (m, 3H), 8.10 (m, 1H), 8.49 (m, 1H), 10.43 (s, 1H)

<Step 2> Synthesis of ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate

Except for using 2-chloro-3- (2,6-dichloropyridin-3-yl) -9H-carbazole instead of 2-chloro-3- (2-chloropyridin-3-yl) -9H-carbazole, Ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate was obtained in the same manner as in <Step 2> of Preparation Example 1.

¹ H-NMR: δ 1.23 (t, 3H), 2.52 (t, 2H), 3.03 (t, 2H), 4.09 (q, 2H), 7.10 (m, 1H), 7.30 (m, 1H), 7.50 ( m, 2H), 7.69 (m, 2H), 8.14 (m, 2H), 10.51 (s, 1H)

Step 3 Synthesis of SC-2

ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-3-yl) instead of ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate Except for using pyridin-2-ylthio) propanoate, SC-2 was obtained by the same process as <Step 3> of Preparation Example 1.

¹ H-NMR: δ 7.30 (m, 2H), 7.51 (m, 1H), 7.71 (m, 3H), 8.08 (m, 2H), 10.48 (s, 1H)

Preparation Example 3 Synthesis of SC-3

<Step 1> Synthesis of 2-chloro-1- (2-chloropyridin-3-yl) -9H-carbazole

Except for using 1-bromo-2-chloro-9H-carbazole instead of 3-bromo-2-chloro-9H-carbazole, the same procedure as in <Step 1> of Preparation Example 1 was carried out to 2-chloro- 1- (2-chloropyridin-3-yl) -9H-carbazole was obtained.

¹ H-NMR: δ 7.08 (m, 1H), 7.29 (m, 1H), 7.52 (m, 1H), 7.68 (m, 2H), 8.09 (m, 2H), 8.31 (m, 2H), 10.42 ( s, 1 H)

<Step 2> Synthesis of ethyl 3- (3- (2-chloro-9H-carbazol-1-yl) pyridin-2-ylthio) propanoate

Except for using 2-chloro-1- (2-chloropyridin-3-yl) -9H-carbazole instead of 2-chloro-3- (2-chloropyridin-3-yl) -9H-carbazole, Preparation Example The same procedure as in <Step 2> of 1 was performed to obtain ethyl 3- (3- (2-chloro-9H-carbazol-1-yl) pyridin-2-ylthio) propanoate.

¹ H-NMR: δ 1.23 (t, 3H), 2.51 (t, 2H), 3.02 (t, 2H), 4.10 (q, 2H), 7.07 (m, 1H), 7.16 (m, 1H), 7.29 ( m, 1H), 7.58 (m, 2H), 7.92 (m, 2H), 8.10 (m, 1H), 8.29 (m, 1H), 10.50 (s, 1H)

Step 3 Synthesis of SC-3

ethyl 3- (3- (2-chloro-9H-carbazol-1-yl) pyridin-2- instead of ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyridin-2-ylthio) propanoate Except for using ylthio) propanoate, SC-3 was obtained by the same process as <Step 3> of Preparation Example 1.

¹ H-NMR: δ 7.33 (m, 2H), 7.55 (m, 2H), 7.80 (m, 1H), 8.11 (m, 2H), 8.59 (m, 2H), 10.50 (s, 1H)

Preparation Example 4 Synthesis of SC-4

<Step 1> Synthesis of 2-chloro-1- (2,6-dichloropyridin-3-yl) -9H-carbazole

Except for using 2,6-dichloropyridin-3-ylboronic acid instead of 2-chloropyridin-3-ylboronic acid, 2-chloro-1- (2 , 6-dichloropyridin-3-yl) -9H-carbazole was obtained.

¹ H-NMR: δ 7.07 (m, 1H), 7.30 (m, 1H), 7.51 (m, 1H), 7.67 (m, 2H), 8.09 (m, 2H), 8.55 (m, 1H)

<Step 2> Synthesis of ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-1-yl) pyridin-2-ylthio) propanoate

Except for using 2-chloro-1- (2,6-dichloropyridin-3-yl) -9H-carbazole instead of 2-chloro-1- (2-chloropyridin-3-yl) -9H-carbazole, Ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-1-yl) pyridin-2-ylthio) propanoate was obtained by the same procedure as in <Step 2> of Preparation Example 3.

¹ H-NMR: δ 1.23 (t, 3H), 2.52 (t, 2H), 3.02 (t, 2H), 4.09 (q, 2H), 7.07 (m, 1H), 7.26 (m, 1H), 7.49 ( m, 1H), 7.64 (m, 1H), 8.10 (m, 3H), 10.49 (s, 1H)

Step 3 Synthesis of SC-4

ethyl 3- (6-chloro-3- (2-chloro-9H-carbazol-1-yl) instead of ethyl 3- (3- (2-chloro-9H-carbazol-1-yl) pyridin-2-ylthio) propanoate Except for using pyridin-2-ylthio) propanoate, SC-4 was obtained by the same process as <Step 3> of Preparation Example 3.

¹ H-NMR: δ 7.29 (m, 2H), 7.49 (m, 1H), 7.61 (m, 1H), 7.80 (m, 1H), 8.11 (m, 3H), 10.48 (s, 1H)

Synthesis Example 1 Synthesis of Mat-1

SC-1 (2.43 g, 8.86 mmol), 1-bromobenzene (4.17 g, 26.56 mmol), Cu powder (0.11 g, 1.77 mmol), K ₂ CO ₃ (2.44 g), which is the compound prepared in Preparation Example 1, under nitrogen stream. , 17.71 mmol), Na ₂ SO ₄ (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-1 (2.17 g, yield 70%).

GC-Mass (calculated: 350.44 g / mol, measured: 350 g / mol)

Synthesis Example 2 Synthesis of Mat-2

Except for using 2-bromonaphthalene instead of 1-bromobenzene, the same process as in Synthesis Example 1 was carried out to obtain a target compound Mat-2 (2.44g, 69% yield).

GC-Mass (theory: 400.49 g / mol, measurement: 400 g / mol)

Synthesis Example 3 Synthesis of Mat-3

Except for using 2-bromopyridine instead of 1-bromobenzene, the same process as in Synthesis Example 1 was carried out to obtain a target compound Mat-3 (2.11g, yield 68%).

GC-Mass (351.42 g / mol, measured: 351 g / mol)

Synthesis Example 4 Synthesis of Mat-4

Except for using 1-bromo-3,5-diphenylbenzene instead of 1-bromobenzene, the same process as in Synthesis Example 1 was performed to obtain Mat-4 (2.89 g, yield 65%) as a target compound.

GC-Mass (Theoretical value: 502.63 g / mol, Measured value: 502 g / mol)

Synthesis Example 5 Synthesis of Mat-5

SC-1 (1.60 g, 5.85 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10 g, 7.85 mmol), NaH (2.11) as a compound prepared in Preparation Example 1 under a nitrogen stream. g, 8.78 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-5 (2.48 g, yield 84%) as a target compound.

GC-Mass (calculated: 505.59 g / mol, measured: 505 g / mol)

Synthesis Example 6 Synthesis of Mat-6

Except for using 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 1-bromobenzene, the same process as in Synthesis Example 5 was carried out to Mat -6 (3.11 g, yield 81%) was obtained.

GC-Mass (calculated: 657.78 g / mol, measured: 657 g / mol)

Synthesis Example 7 Synthesis of Mat-7

The same procedure as in Synthesis Example 5 was performed except that 3-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole was used instead of 1-bromobenzene. To obtain the title compound Mat-7 (3.21g, yield 82%).

GC-Mass (calculated: 670.78 g / mol, measured: 670 g / mol)

Synthesis Example 8 Synthesis of Mat-8

Except for using 2-bromo-4,6-diphenylpyridine instead of 1-bromobenzene, the same process as in Synthesis Example 1 was carried out to obtain a target compound Mat-8 (2.76 g, yield 62%).

GC-Mass (calculated: 503.62 g / mol, measured: 503 g / mol)

Synthesis Example 9 Synthesis of Mat-9

SC-3 (2.43 g, 8.86 mmol), 1-bromobenzene (4.17 g, 26.56 mmol), Cu powder (0.11 g, 1.77 mmol), K ₂ CO ₃ (2.44 g), which is a compound prepared in Preparation Example 3, under nitrogen stream. , 17.71 mmol), Na ₂ SO ₄ (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-9 (2.01 g, yield 65%).

GC-Mass (calculated: 350.44 g / mol, measured: 350 g / mol)

Synthesis Example 10 Synthesis of Mat-10

Except for using 2-bromonaphthalene instead of 1-bromobenzene, the same procedure as in Synthesis Example 9 was carried out to obtain a target compound Mat-1 (2.44g, 69% yield).

GC-Mass (theory: 400.49 g / mol, measurement: 400 g / mol)

Synthesis Example 11 Synthesis of Mat-11

Except for using 2-bromopyridine instead of 1-bromobenzene, the same procedure as in Synthesis Example 9 was carried out to obtain a target compound Mat-11 (2.11 g, yield 68%).

GC-Mass (351.42 g / mol, measured: 351 g / mol)

Synthesis Example 12 Synthesis of Mat-12

Except for using 1-bromo-3,5-diphenylbenzene instead of 1-bromobenzene, the same procedure as in Synthesis Example 9 was carried out to obtain a target compound Mat-12 (2.71 g, yield 61%).

GC-Mass (Theoretical value: 502.63 g / mol, Measured value: 502 g / mol)

Synthesis Example 13 Synthesis of Mat-13

SC-3 (1.60 g, 5.85 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10 g, 7.85 mmol), NaH (2.11) as a compound prepared in Preparation Example 3 under a nitrogen stream. g, 8.78 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-13 (2.36 g, yield 80%) as a target compound.

GC-Mass (calculated: 505.59 g / mol, measured: 505 g / mol)

Synthesis Example 14 Synthesis of Mat-14

Except for using 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 1-bromobenzene, the same process as in Synthesis Example 13 was carried out to Mat -14 (3.15 g, yield 82%) was obtained.

GC-Mass (calculated: 657.78 g / mol, measured: 657 g / mol)

Synthesis Example 15 Synthesis of Mat-15

The same procedure as in Synthesis Example 13 was carried out except that 3-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole was used instead of 1-bromobenzene. To give Mat-15 (3.21 g, yield 82%) as the target compound.

GC-Mass (calculated: 670.78 g / mol, measured: 670 g / mol)

Synthesis Example 16 Synthesis of Mat-16

Except for using 2-bromo-4,6-diphenylpyridine instead of 1-bromobenzene, the same procedure as in Synthesis Example 1 was carried out to obtain a target compound Mat-16 (2.81 g, yield 63%).

GC-Mass (calculated: 503.62 g / mol, measured: 503 g / mol)

Synthesis Example 17 Synthesis of Mat-17

Under a stream of nitrogen, the compound prepared in Preparation Example 2, SC-2 (2.43 g, 7.88 mmol), phenylboronic acid (1.15 g, 9.47 mmol), NaOH (0.95 g, 23.67 mmol) and THF / H ₂ O (100 ml) / 50 ml) was mixed and stirred, and then 0.46 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the obtained organic layer was purified by column chromatography to give the intermediate compound IMC-17 (2.28 g, yield 83%).

Except for using IMC-18 instead of SC-1, 2-bromo-4,6-diphenylpyridine instead of 1-bromobenzene, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound Mat-17 (2.45 g, yield 65%).

GC-Mass (calculated: 579.71 g / mol, measured: 579 g / mol)

Synthesis Example 18 Synthesis of Mat-18

Except for using IMC-18 instead of SC-1, the same process as in Synthesis Example 5 was performed to obtain Mat-18 (3.03 g, yield 80%) as a target compound.

GC-Mass (calculated: 581.69 g / mol, measured: 581 g / mol)

Synthesis Example 19 Synthesis of Mat-19

Except for using IMC-18 instead of SC-1, the same procedure as in Synthesis Example 6 was performed to obtain Mat-19 (3.72 g, yield 78%) as a target compound.

GC-Mass (733.88 g / mol, measured: 733 g / mol /)

Synthesis Example 20 Synthesis of Mat-20

Except for using pyridin-3-ylboronic acid instead of phenylboronic acid, the same process as in Synthesis Example 17 was carried out to obtain Mat-20 (2.42 g, yield 64%) as a target compound.

GC-Mass (calculated: 580.70 g / mol, measured: 580 g / mol)

Synthesis Example 21 Synthesis of Mat-21

Except for using IMC-20 instead of SC-1, the same procedure as in Synthesis Example 5 was performed to obtain Mat-21 (2.95 g, yield 78%) as a target compound.

GC-Mass (calculated: 582.68 g / mol, measured: 582 g / mol)

Synthesis Example 22 Synthesis of Mat-22

Except for using IMC-20 instead of SC-1, the same procedure as in Synthesis Example 6 was carried out to obtain Mat-22 (3.58 g, yield 75%) as a target compound.

GC-Mass (calculated: 734.87 g / mol, measured: 734 g / mol)

Synthesis Example 23 Synthesis of Mat-23

The same procedure as in Synthesis Example 17 was carried out except that 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-ylboronic acid was used instead of phenylboronic acid. The target compound Mat-23 (3.39 g, yield 58%) was obtained.

GC-Mass (Theoretical value: 899.28 g / mol, Measured value: 899 g / mol)

Synthesis Example 24 Synthesis of Mat-24

Except for using IMC-23 instead of SC-1, the same procedure as in Synthesis Example 5 was performed to obtain Mat-24 (4.10 g, yield 70%) as a target compound.

GC-Mass (Theoretical value: 901.27 g / mol, Measured value: 901 g / mol)

Synthesis Example 25 Synthesis of Mat-25

Except for using IMC-23 instead of SC-1, the same procedure as in Synthesis Example 6 was carried out to obtain a target compound Mat-25 (4.65 g, yield 68%).

GC-Mass (Theoretical value: 1053.34 g / mol, Measured value: 1053 g / mol)

Synthesis Example 26 Synthesis of Mat-26

Under a stream of nitrogen, the compounds prepared in Preparation Example 4, SC-4 (2.43 g, 7.88 mmol), phenylboronic acid (1.15 g, 9.47 mmol), NaOH (0.95 g, 23.67 mmol) and THF / H ₂ O (100 ml) / 50 ml) was mixed and stirred, and then 0.46 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the obtained organic layer was purified by column chromatography to give the intermediate compound IMC-26 (2.34 g, yield 85%).

Except for using IMC-26 instead of SC-1, 2-bromo-4,6-diphenylpyridine instead of 1-bromobenzene, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound Mat-26 (2.48 g, yield 66%).

GC-Mass (calculated: 579.71 g / mol, measured: 579 g / mol)

Synthesis Example 27 Synthesis of Mat-27

Except for using IMC-26 instead of SC-1, the same procedure as in Synthesis Example 5 was carried out to obtain a target compound Mat-27 (3.10 g, yield 80%).

GC-Mass (calculated: 581.69 g / mol, measured: 581 g / mol)

Synthesis Example 28 Synthesis of Mat-28

Except for using IMC-26 instead of SC-1, the same procedure as in Synthesis Example 6 was carried out to obtain a target compound Mat-28 (3.73 g, 74% yield).

GC-Mass (733.88 g / mol, measured: 733 g / mol /)

Synthesis Example 29 Synthesis of Mat-29

Except for using pyridin-3-ylboronic acid instead of phenylboronic acid, the same procedure as in Synthesis Example 26 was carried out to obtain a target compound Mat-29 (2.51 g, yield 65%).

GC-Mass (calculated: 580.70 g / mol, measured: 580 g / mol)

Synthesis Example 30 Synthesis of Mat-30

Except for using IMC-29 instead of SC-1, the same process as in Synthesis Example 5 was performed to obtain Mat-30 (2.91 g, yield 75%) as a target compound.

GC-Mass (calculated: 582.68 g / mol, measured: 582 g / mol)

Synthesis Example 31 Synthesis of Mat-31

Except for using IMC-29 instead of SC-1, the same procedure as in Synthesis Example 6 was carried out to obtain a target compound Mat-31 (3.53 g, yield 72%).

GC-Mass (calculated: 734.87 g / mol, measured: 734 g / mol)

Synthesis Example 32 Synthesis of Mat-32

The same procedure as in Synthesis Example 26 was performed except that 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-ylboronic acid was used instead of phenylboronic acid. The obtained compound Mat-32 (3.71 g, yield 60%) was obtained.

GC-Mass (Theoretical value: 899.28 g / mol, Measured value: 899 g / mol)

Synthesis Example 33 Synthesis of Mat-33

Except for using IMC-32 instead of SC-1, the same procedure as in Synthesis Example 5 was performed to obtain Mat-33 (4.09 g, yield 68%) as a target compound.

GC-Mass (Theoretical value: 901.27 g / mol, Measured value: 901 g / mol)

Synthesis Example 34 Synthesis of Mat-34

Except for using IMC-32 instead of SC-1, the same procedure as in Synthesis Example 6 was carried out to obtain Mat-25 (4.42 g, 61% yield) as a target compound.

GC-Mass (Theoretical value: 1053.34 g / mol, Measured value: 1053 g / mol)

[Examples 1 to 34] Fabrication of green organic EL device

After the high purity sublimation purification of Mat-1 to Mat-34 compounds synthesized in Synthesis Example 1-34 by a conventionally known method, a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / Matt-1 to Mat-34 compound + 10% Ir (ppy) ₃ (300nm) / BCP (10 nm) / Alq ₃ on the prepared ITO transparent electrode The organic EL device was fabricated by laminating in the order of (30 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 as a light emitting host material when forming the emission layer.

[Evaluation example]

For each of the green organic EL devices produced in Examples 1-34 and Comparative Example 1, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 MAT-1 6.55 520 39.3 Example 2 MAT-2 6.50 518 39.7 Example 3 MAT-3 6.69 521 40.3 Example 4 MAT-4 6.41 520 41.0 Example 5 MAT-5 6.46 517 40.8 Example 6 MAT-6 6.50 515 41.0 Example 7 MAT-7 6.51 521 41.4 Example 8 MAT-8 6.70 520 40.5 Example 9 MAT-9 6.50 523 40.8 Example 10 MAT-10 6.40 519 41.1 Example 11 MAT-11 6.43 520 40.8 Example 12 MAT-12 6.54 518 41.5 Example 13 MAT-13 6.70 519 41.3 Example 14 MAT-14 6.50 516 42.0 Example 15 MAT-15 6.57 520 41.9 Example 16 MAT-16 6.60 522 41.5 Example 17 MAT-17 6.65 518 39.9 Example 18 MAT-18 6.70 519 41.5 Example 19 MAT-19 6.63 518 41.0 Example 20 MAT-20 6.52 519 41.3 Example 21 MAT-21 6.60 515 40.8 Example 22 MAT-22 6.55 517 41.0 Example 23 MAT-23 6.45 516 40.5 Example 24 MAT-24 6.50 520 39.8 Example 25 MAT-25 6.60 520 39.9 Example 26 MAT-26 6.75 519 39.8 Example 27 MAT-27 6.60 520 40.1 Example 28 MAT-28 6.55 523 39.6 Example 29 MAT-29 6.70 515 40.9 Example 30 MAT-30 6.54 519 40.5 Example 31 MAT-31 6.67 520 40.0 Example 32 MAT-32 6.68 521 41.0 Example 33 MAT-33 6.50 520 41.3 Example 34 MAT-34 6.65 522 40.7 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the organic EL device of Examples 1 to 34 using the compounds (Mat-1 to Mat-34) according to the present invention as a light emitting layer of the green organic EL device, uses a conventional CBP When compared with the green organic electroluminescent element of the comparative example 1, it turns out that it shows more excellent performance in efficiency and a drive voltage.

Claims (7)

delete Compound represented by the formula of any one of formulas (3) to (8):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In this formula,
Ar ₁ is a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₆ -C ₄₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted A substituted C ₃ to C ₄₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group;
R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, Substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₆ to C ₄₀ Arylalkyl group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted C ₃ -C ₄₀ heterocycloalkyl group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, and substituted or is selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C _40, wherein they form a fused ring or non-adjacent groups Castle and;
X ₁ to X ₄ are the same as or different from each other, and are each independently selected from CR ₉ , N, wherein one of X ₁ to X ₄ is N;
R ₉ is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, substituted or unsubstituted Substituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₆ to C ₄₀ arylalkyl group, Substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted C ₃ to C ₄₀ heterocycloalkyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, and substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, wherein they form a condensed ring or non-form with adjacent groups ,
In R ₁ to R ₉ , and Ar ₁ , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, Nuclear atom number 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₆ to C ₄₀ arylalkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, and C ₆ to C ₄₀ arylsilyl group are each independently deuterium, halogen, cyano group, C _1- C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryl Oxy group, C ₁ -C ₄₀ alkyloxy group, C ₆ -C ₄₀ arylamine group, C ₆ -C ₄₀ aryl group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nucleus atoms in the group consisting of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, and a C ₆ ~ C ₄₀ aryl group in the silyl Substituted with one or more substituents selected, or is unsubstituted. 3. The method of claim 2,
The compound represented by Formula 3 to Formula 8 is selected from the group consisting of compounds represented by the following formulas C-1 to C-24:

Wherein R ₁ to R ₉ and Ar ₁ are as defined in claim 2. The method of claim 3, wherein Ar ₁ Is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,
The C ₆ ~ C ₄₀ aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ -aryl group, C ₆ -C ₄₀ arylalkyl group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, and C ₆ -C A compound, which is unsubstituted or substituted with one or more substituents selected from the group consisting of ₄₀ arylsilyl groups. The method according to claim 3, wherein R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₁ ~ C ₄₀ It is selected from the group consisting of an alkylsilyl group of, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group,
The C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 nuclear aryl heteroaryl group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C _The arylsilyl group of ₆ to C ₄₀ is each independently deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C _40, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ arylamine group of C _40, C ₆ ~ C ₄₀ At least one selected from the group consisting of an arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, and a C ₆ to C ₄₀ arylsilyl group Compound substituted or unsubstituted by a substituent. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
At least one of the one or more organic material layers comprises the compound according to any one of claims 2 to 5, characterized in that the organic electroluminescent device. The organic electroluminescent device according to claim 6, wherein the organic material layer including the compound is a light emitting layer.