WO2015093818A2 - Organic compound and organic electroluminescent device including same - Google Patents

Abstract

The present invention relates to: a novel benzopyrrole carbazole-based compound having excellent hole injection and transport performance, light-emitting performance and the like; and an organic electroluminescenct device having improved characteristics such as light-emitting efficiency, a driving voltage, and life by including the compound in one or more organic layers.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the compound.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material included in the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color. In addition, a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.

The dopant material may 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. In this case, since phosphorescent dopants can theoretically improve luminous efficiency up to 4 times compared to fluorescent dopants, studies on phosphorescent dopants as well as phosphorescent hosts are being conducted.

At present, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. In addition, as a phosphorescent dopant material used in the light emitting layer, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.

However, existing materials have low glass transition temperature and poor thermal stability, and thus are not satisfactory in terms of lifespan in an organic EL device, and still need improvement in terms of light emission characteristics.

In order to solve the above problems, an object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and excellent luminescence properties.

Moreover, an object of this invention is to provide the organic electroluminescent element containing the said organic compound.

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

[Formula 1]

In Chemical Formula 1,

At least one of R ₁ and R ₂ and R ₂ and R ₃ may be bonded to each other to form a condensed ring represented by Formula 2 below;

[Formula 2]

In Chemical Formula 2,

The dotted line is a part which is combined with Formula 1,

X ₁ is selected from the group consisting of CAr ₂ Ar ₃ , NAr ₄ , O, S and SiAr ₅ Ar ₆ ,

R ₁ to R ₃ and R ₄ to R ₁₀ except for forming a condensed ring are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ of alkyloxy, C ₆ to C ₆₀ of the aryloxy group, C group ₃ ~ C ₄₀ alkylsilyl, C group ₆ to aryl of C ₆₀ alkylsilyl, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of the adjacent Combine with groups to form condensed rings,

Ar ₁ to Ar ₆ are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 3 nuclear atoms 40 heterocycloalkyl groups, C ₆ -C ₆₀ aryl groups, heteroaryl groups of _5-60 nuclear atoms, C ₁ -C ₄₀ alkyloxy groups, C ₆ -C ₆₀ aryloxy groups, C ₃ -C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group,

The alkyl group, alkenyl group, alkynyl group cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group of R ₁ to R ₁₀ and Ar ₁ to Ar ₆ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group , C ₃ ~ C ₄₀ cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group , C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group , C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl ring is a substituted or unsubstituted amine groups at least one member selected from the group consisting of. In this case, when substituted with a plurality of substituents a plurality of substituents are the same or different from each other.

On the other hand, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.

In the present invention, alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. It may also include a form in which two or more rings are attached to each other (pendant) or condensed. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included, and may also include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

In the present invention, arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.

Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The compound of the present invention is condensed with a 5-membered aromatic ring, or 5-membered heteroaromatic ring in the benzo pyrrole carbazole basic skeleton, and various substituents are bonded, represented by the formula (1).

As with the compound of the present invention, an electron withdrawing group (EWG) having an electron donating group (EDG) having a large electron donating property and having a high electron absorption in a benzopyrrolecarbazole basic skeleton having excellent hole transporting properties When introduced, the bonding force between holes and electrons is high and the whole molecule is bipolar, so that it can be advantageously applied as a host in the phosphorescent layer and can be applied to the electron transport layer. In addition, when an electron donating group (EDG) having a large electron donor is introduced as a substituent, the electron donating group (EDG) may be applied to a hole transport layer and a hole injection layer.

In addition, since the compound of the present invention has a high glass transition temperature by significantly increasing the molecular weight due to various aromatic ring substituents, it is superior in thermal stability to conventional organic material (for example, CBP).

Therefore, when the compound of the present invention is used as a material of a hole injection layer, a hole transport layer, an electron transport layer or a light emitting layer of the organic electroluminescent device, compared to the conventional organic material (for example, CBP), the efficiency and lifetime of the organic electroluminescent device Can be improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.

In view of the characteristics of the organic electroluminescent device, the compound of the present invention, X ₁ is preferably NAr ₄ , O or S, more preferably NAr ₄ .

In addition, in the compound of the present invention, considering the wide bandgap and thermal stability of the compound, Ar ₁ to Ar ₆ are each independently C ₆ ~ C ₆₀ aryl group, nuclear atomic number 5 to 60 heteroaryl group, C it is selected from the ₆ ~ C ₄₀ aryl amine group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl preferred.

In the compound of the present invention, R ₁ to R ₃ and R ₄ to R ₁₀ are each independently hydrogen, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₆ except forming a condensed ring. ~ to be C ₆₀ aryl group, nuclear atoms selected from 5 to 60 heteroaryl group, and the group consisting of C ₆ - C ₆₀ aryl amines are preferred.

Specifically, in the compound of the present invention, Ar ₁ to Ar ₆ , R ₁ to R ₃ and R ₄ to R ₁₀ which do not form a condensed ring are each independently selected from a structure (substituent) composed of hydrogen or the following S 1 to S 205. It is preferable.

Such a compound of the present invention is preferably selected from the group consisting of compounds represented by the following formula (3-6).

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,

X ₁ , R ₁ to R _10, Ar ₁ are the same as defined in Chemical Formula 1.

Compounds of the invention may be embodied in the compounds exemplified below. However, the compounds of the present invention are not limited to the compounds illustrated below.

The compound of Formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples.

2. Organic electroluminescent device

Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the present invention includes an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, at least one of the organic material layer comprises an organic electric field comprising at least one compound represented by the formula (1) Provided is a light emitting device.

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. Preferably, the compound represented by Chemical Formula 1 may be included in the organic electroluminescent device as a light emitting layer material. In this case, the organic EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.

In particular, the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, and more preferably a phosphorescent host of the light emitting layer.

The structure of the organic EL device of the present invention is not particularly limited, but a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode may be sequentially stacked. An electron injection layer may be positioned on the electron transport layer. In addition, the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted at an interface between an electrode and an organic material layer.

In the organic electroluminescent device of the present invention, the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1. Can be.

For example, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film, or the like may be used as the substrate.

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The material used for the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited as long as it is a conventional material known in the art.

Hereinafter, the present invention will be described in detail with reference to the following 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 Core1

Step 1 Synthesis of 3H-naphtho [1,2-g] indole

Dissolve 1-nitrophenanthrene (20 g, 89.59 mmol) in 800 ml THF under nitrogen stream, lower to -40 ° C and add vinylmagnesium bromide (35.27 g, 268.78 mmol). After stirring for 20 minutes, the reaction was terminated using a saturated NH ₄ Cl aqueous solution, and the organic layer was separated with ethyl acetate, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 12.6 g (yield 65%) of 3H-naphtho [1,2-g] indole. .

¹ H-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.71 (m, 2H), 7.88 (m, 3H), 8.12 (d, 1H), 8.93 (m, 2H), 11.35 ( s, 1 H)

<Step 2> Synthesis of 3-phenyl-3H-naphtho [1,2-g] indole

3H-naphtho [1,2-g] indole (12.6 g, 57.99 mmol), Iodobenzene (17.74 g, 86.98 mmol), Cu powder (1.9 g, 28.99 mmol), K ₂ CO ₃ (12 g, 86.98 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C. for 12 hours. After the reaction was completed, 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 12.7g (yield: 75%) of 3-phenyl-3H-naphtho [1,2-g] indole.

¹ H-NMR: δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.85 (m, 3H), 8.12 (d, 1H), 8.94 (m, 2H)

Step 3 Synthesis of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole

3-phenyl-3H-naphtho [1,2-g] indole (12.7 g, 43.34 mmol) was added to 1,4-dioxane (400 ml) and stirred under a nitrogen stream. The mixture was added to a solvent diluted with 15 ml of nitric acid to a constant of 24 ml and stirred at 60 ° C. for 0.5 hour. After completion of the reaction, a constant of 400 ml was added, 1,4-dioxane 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 8.0g (yield: 55%) of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole.

¹ H-NMR: δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.88 (d, 1H), 8.08 (t, 1H), 8.51 (d, 1H), 8.89 ( m, 2H)

<Step 4> Synthesis of Core1

9-nitro-3-phenyl-3H-naphtho [1,2-g] indole (8.0g, 23.66mmol), triphenylphosphine (15.4g, 59.15mmol), 1,2-dichlorobenzene (120ml) under nitrogen stream Stir for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed by distillation and extracted with dichloromethane. The extracted organic layer was dried over MgSO ₄ and filtered under reduced pressure. After distilling under reduced pressure on the filtered organic layer, 4.8 g (yield: 66%) of Core1 was obtained by using column chromatography.

¹ H-NMR: δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.88 (m, 3H), 8.12 (d, 1H), 8.51 (d, 1H), 11.15 ( s, 1 H)

Preparation Example 2 Synthesis of Core2

<Step 1> Synthesis of 8H-naphtho [1,2-f] indole and 1H-naphtho [2,1-e] indole

Except for using 2-nitrophenanthrene (30g, 134.39mmol) instead of 1-nitrophenanthrene, the same process as in <Step 1> of [Preparation Example 1] was performed, followed by 8H-naphtho [1,2-f] indole 10.21g ( yield 35%), and 9.34g (yield: 32%) of 1H-naphtho [2,1-e] indole was obtained.

¹ H-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.73 (m, 2H), 7.88 (m, 2H) 7, 8.13 (s, 1H), 8.93 (m, 2H), 11.22 (s, 1H)

¹ H-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.72 (m, 2H), 7.85 (d, 1H), 8.13 (d, 1H), 8.98 (m, 2H) 11.25 (s , 1H)

<Step 2> Synthesis of 8-phenyl-8H-naphtho [1,2-f] indole

Same procedure as in <Step 2> of [Preparation Example 1], except that 8H-naphtho [1,2-f] indole (10.21 g, 47.05 mmol) was used instead of 3H-naphtho [1,2-g] indole. 8-phenyl-8H-naphtho [1,2-f] indole 8.5g (yield: 62%) was obtained by the following procedure.

¹ H-NMR: δ 6.52 (d, 1H), 7.60 (m, 6H), 7.74 (m, 2H), 7.85 (m, 2H) 8.12 (m, 2H), 8.95 (m, 2H)

<Step 3> Synthesis of 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole

[Preparation Example 1], except that 8-phenyl-8H-naphtho [1,2-f] indole (8.5g, 29.01mmol) was used instead of 3-phenyl-3H-naphtho [1,2-g] indole. 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole 5.0g (yield: 52%) was obtained by the same process as in <Step 3>.

¹ H-NMR: δ 6.52 (m, 3H), 7.58 (m, 6H), 7.69 (m, 2H), 7.85 (m, 2H) 8.10 (m, 2H), 8.51 (d, 1H), 8.81 (d , 1H) 8.95 (s, 1H)

<Step 4> Synthesis of Core2

Use of 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole (5.0 g, 14.79 mmol) instead of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole Aside from the same procedure as in <Step 4> of [Preparation Example 1], 2.7g (yield: 61%) of Core2 was obtained.

¹ H-NMR: δ 6.48 (d, 1H), 7.55 (m, 6H), 7.73 (m, 2H), 7.88 (m, 2H) 8.13 (m, 2H), 11.18 (s, 1H)

Preparation Example 3 Synthesis of Core3

<Step 1> Synthesis of 1-phenyl-1H-naphtho [2,1-e] indole

Same procedure as in <Step 2> of [Preparation Example 1], except that 1H-naphtho [2,1-e] indole (9.34 g, 43.04 mmol) was used instead of 3H-naphtho [1,2-g] indole. Was carried out to obtain 8.57 g (yield: 68%) of 1-phenyl-1H-naphtho [2,1-e] indole.

¹ H-NMR: δ 6.52 (s, 3H) 7.60 (m, 6H), 7.15 (m, 2H), 7.88 (m, 3H) 8.13 (d, 1H), 8.92 (m, 2H)

<Step 2> Synthesis of 9-nitro-1-phenyl-1H-naphtho [2,1-e] indole

[Preparation Example 1], except that 1-phenyl-1H-naphtho [2,1-e] indole (8.57g, 29.26mmol) was used instead of 3-phenyl-3H-naphtho [1,2-g] indole. 5.2g (yield: 53%) of 9-nitro-1-phenyl-1H-naphtho [2,1-e] indole was obtained by following the same procedure as in <Step 3>.

¹ H-NMR: δ 6.50 (d, 1H) 7.55 (m, 6H), 7.72 (m, 2H), 7.88 (d, 1H) 8.08 (t, 1H), 8.52 (d, 1H), 8.92 (m, 2H)

<Step 3> Synthesis of Core3

Use of 9-nitro-1-phenyl-1H-naphtho [2,1-e] indole (5.2 g, 15.51 mmol) instead of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole Aside from the same procedure as in <Step 4> of [Preparation Example 1], 2.9g (yield: 62%) of Core3 was obtained.

¹ H-NMR: δ 6.52 (d, 1H) 7.58 (m, 6H), 7.72 (m, 2H), 7.88 (m, 2H) 8.11 (d, 1H), 11.12 (s, 1H)

Preparation Example 4 Synthesis of Core4

<Step 1> Synthesis of (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene

(E) -1- (2-bromovinyl) naphthalene (20 g, 85.83 mmol) under nitrogen stream, thiophen-2-ylboronic acid (13 g, 102.99 mmol), K ₂ CO ₃ (35.5 g, 257.49 mmol), 400 ml / 100 ml THF / H ₂ O was added and stirred. Pd (PPh ₃ ) ₄ (2.97 g, 2.57 mmol) was added at 40 ° C., and the mixture was stirred under reflux at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and 16.4 g (yield: 81%) of (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene was obtained by column chromatography.

¹ H-NMR: δ 6.95 (m, 3H) 7.17 (t, 1H), 7.52 (m, 3H), 7.69 (d, 1H) 7.78 (d, 1H), 7.96 (m, 2H), 8.08 (d, 1H)

<Step 2> Synthesis of phenanthro [1,2-b] thiophene

Under nitrogen stream, (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene (16.4g, 69.39mmol), Iodine (18.11g, 138.78mmol) and 300ml of cyclohexane were added for 12 hours at 80 ℃. It was stirred at reflux. After completion of the reaction, the mixture was extracted with dichloromethane and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, 10.7 g (yield: 66%) of phenanthro [1,2-b] thiophene was obtained by column chromatography.

¹ H-NMR: δ 7.75 (m, 7H), 8.12 (d, 1H), 8.93 (m, 2H)

Step 3 Synthesis of 9-nitrophenanthro [1,2-b] thiophene

Except for using phenanthro [1,2-b] thiophene (10.7g, 45.66mmol) instead of 3-phenyl-3H-naphtho [1,2-g] indole, The same procedure was followed to obtain 6.7 g (yield: 53%) of the target compound, 9-nitrophenanthro [1,2-b] thiophene.

¹ H-NMR: δ 7.72 (m, 4H), 7.88 (d, 1H), 8.52 (d, 1H), 8.82 (d, 1H) 8.95 (d, 1H)

<Step 4> Synthesis of Core4

[Preparation Example 1] except that 9-nitrophenanthro [1,2-b] thiophene (6.7 g, 24.01 mmol) was used instead of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole. 3.8g (yield: 64%) of Core4 was obtained by following the same procedure as in <Step 4>.

¹ H-NMR: δ 7.71 (m, 7H), 8.15 (d, 1H), 11.18 (s, 1H)

Preparation Example 5 Synthesis of Core5

<Step 1> Synthesis of (E) -2- (2- (naphthalen-1-yl) vinyl) furan

Except for using furan-2-ylboronic acid (11.4g, 102.99mmol) instead of thiophen-2-ylboronic acid, perform the same procedure as in <Step 1> of [Preparation Example 4] (E) -2- ( 13.6 g of 2- (naphthalen-1-yl) vinyl) furan (yield: 72%) was obtained.

¹ H-NMR: δ 6.52 (d, 1H), 6.95 (m, 3H), 7.55 (m, 3H), 7.78 (m, 2H), 7.96 (m, 2H), 8.10 (d, 1H)

Step 2 Synthesis of 13-nitrodibenzo [b, mn] xanthene

Use of (E) -2- (2- (naphthalen-1-yl) vinyl) furan (13.6 g, 61.80 mmol) instead of (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene Except for the same procedure as in <Step 2> of [Preparation Example 4] except that 13-nitrodibenzo [b, mn] xanthene 7.8g (yield: 58%) was obtained.

¹ H-NMR: δ 6.66 (d, 1H), 7.52 (d, 1H), 7.74 (m, 2H), 7.86 (m, 3H), 8.14 (d, 1H), 8.96 (m, 2H)

Step 3 Synthesis of 9-nitrophenanthro [1,2-b] furan

Except for using 13-nitrodibenzo [b, mn] xanthene (7.8g, 35.77mmol) instead of phenanthro [1,2-b] thiophene, the procedure was the same as in <Step 3> of [Preparation Example 4] 9 -4.5 g (yield: 48%) of nitrophenanthro [1,2-b] furan was obtained.

¹ H-NMR: δ 6.66 (d, 1H), 7.52 (d, 1H), 7.74 (m, 2H), 7.88 (d, 1H), 8.11 (t, 1H), 8.53 (d, 1H), 8.82 ( d, 1H), 8.95 (d, 1H)

<Step 4> Synthesis of Core5

Same procedure as in <Step 4> of [Preparation Example 4], except that 9-nitrophenanthro [1,2-b] furan (4.5 g, 17.17 mmol) was used instead of 9-nitrophenanthro [1,2-b] thiophene. Was carried out to obtain 2.5 g of Core5 (yield: 63%).

¹ H-NMR: δ 6.68 (d, 1H), 7.55 (d, 1H), 7.72 (m, 2H), 7.85 (m, 3H), 8.12 (d, 1H), 11.13 (s, 1H)

Synthesis Example 1 Synthesis of Inv 88

Under nitrogen stream, Core1 (3.0 g, 9.79 mmol), 4-chloro-2-phenylpyrimidine (2.24 g, 11.75 mmol), Pd (OAc) ₂ (0.1 g, 0.48 mmol), NaO (t-bu) (2.82 g, 29.37 mmol), P (t-bu) ₃ (0.39 g, 1.95 mmol) and Toluene (80 ml) were mixed and then stirred at 110 ° C. for 12 hours. After completion of the reaction was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to give the title compound Inv 88 (2.5g, 57% yield).

GC-Mass (Theoretical value: 460.53 g / mol, Measured value: 460 g / mol)

Synthesis Example 2 Synthesis of Inv 106

Core1 (3.0 g, 9.79 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.74 mmol), NaH (0.39 g, 9.79 mmol) and DMF (80 ml) under nitrogen stream 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 Inv 106 (3.5 g, yield 67%) as a target compound.

GC-Mass (Theoretical value: 537.61 g / mol, Measured value: 537 g / mol)

Synthesis Example 3 Synthesis of Inv 107

Inv 107 (3.3g, Yield) was carried out in the same manner as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (3.13g, 11.74mmol) was used instead of 4-chloro-2-phenylpyrimidine. 63%).

GC-Mass (Theoretical value: 536.62 g / mol, Measured value: 536 g / mol)

Synthesis Example 4 Synthesis of Inv 141

Except for using 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.02g, 11.74mmol) instead of 4-chloro-2-phenylpyrimidine, the same procedure as in Synthesis Example 1 was carried out to provide Inv 141 ( 3.6 g, yield 61%) was obtained.

GC-Mass (Theoretical value: 612.72 g / mol, Measured value: 612 g / mol)

Synthesis Example 5 Synthesis of Inv 168

The same procedure as in Synthesis Example 1 was performed except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.03 g, 11.74 mmol) was used instead of 4-chloro-2-phenylpyrimidine. Inv 168 (3.6 g, yield 60%) was obtained as a target compound.

GC-Mass (Theoretical value: 613.71 g / mol, Measured value: 613 g / mol)

Synthesis Example 6 Synthesis of Inv 199

Except for using 4- (2-chloropyrimidin-4-yl) benzonitrile (2.53 g, 11.74 mmol) instead of 4-chloro-2-phenylpyrimidine, the same procedure as in Synthesis Example 1 was carried out to obtain Inv 199 (2.9). g, yield 62%).

GC-Mass (Theoretical value: 485.54 g / mol, Measured value: 485 g / mol)

Synthesis Example 7 Synthesis of Inv 223

Core2 (3g, 9.79mmol) was used instead of Core1 and 2- (3-chlorophenyl) -4-phenylpyrimidine (3.13g, 11.74mmol) was used instead of 4-chloro-2-phenylpyrimidine and the same as Synthesis Example 1 The process was carried out to obtain the title compound Inv 223 (3.0g, yield 58%).

GC-Mass (Theoretical value: 536.62 g / mol, Measured value: 536 g / mol)

Synthesis Example 8 Synthesis of Inv 225

Core2 (3.0 g, 9.79 mmol), 4-bromo-N, N-diphenylaniline (3.8 g, 11.74 mmol), Cu powder (0.31 g, 4.89 mmol), K ₂ CO ₃ (2.02 g, 14.68 mmol) under nitrogen stream , And nitrobenzene (80 ml) were mixed and stirred at 190 ° C. for 12 hours. After the reaction was completed, 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 Inv 225 (3.5g, 65% yield).

GC-Mass (Theoretical value: 549.66 g / mo, Measured value: 549 g / mol)

Synthesis Example 9 Synthesis of Inv 232

Except for using 2-bromo-4,6-diphenylpyridine (3.64g, 11.74mmol) instead of 4-bromo-N, N-diphenylaniline, the same procedure as in Synthesis Example 8 was carried out to give Inv 232 (3.3g) as a target compound. , Yield 63%) was obtained.

GC-Mass (Theoretical value: 535.64 g / mol, Measured value: 535 g / mol)

Synthesis Example 10 Synthesis of Inv 233

Same as Synthesis Example 8 except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.5g, 11.74mmol) instead of 4-bromo-N, N-diphenylaniline The process was carried out to obtain the target compound Inv 233 (3.8g, 64% yield).

GC-Mass (Theoretical value: 613.71 g / mol, Measured value: 613 g / mol)

Synthesis Example 11 Synthesis of Inv 253

Except for using 9- (4-bromophenyl) -9H-carbazole (3.78g, 11.74mmol) instead of 4-bromo-N, N-diphenylaniline, Inv 253 ( 3.3 g, yield 62%).

GC-Mass (Theoretical value: 547.65 g / mol, Measured value: 547 g / mol)

Synthesis Example 12 Synthesis of Inv 274

Same as Synthesis Example 8 except that Core3 (3.0g 9.79mmol) was used instead of Core2 and 2-bromo-4,6-diphenylpyrimidine (3.6g, 11.74mmol) was used instead of 4-bromo-N, N-diphenylaniline. The procedure was followed to obtain the target compound Inv 274 (3.46 g, 66% yield).

GC-Mass (Theoretical value: 536.62 g / mol, Measured value: 536 g / mol)

Synthesis Example 13 Synthesis of Inv 278

Core3 (3.0g, 9.79mmol) is used instead of Core1 and 2,4-di (biphenyl-3-yl) -6- (4-chlorophenyl) -1,3,5-triazine instead of 4-chloro-2-phenylpyrimidine Except for using (5.82g, 11.74mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the title compound Inv 278 (4.5 g, yield 60%).

GC-Mass (Theoretical value: 765.9 g / mol, Measured value: 765 g / mol)

Synthesis Example 14 Synthesis of Inv 284

4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.02g, 11.74mmol) instead of 2,4-di (biphenyl-3-yl) -6- (4-chlorophenyl) -1,3,5-triazine Except for using the same procedure as in Synthesis Example 13 to obtain the title compound Inv 284 (3.4g, yield 57%).

GC-Mass (Theoretical value: 612.72 g / mol, Measured value: 612 g / mol)

Synthesis Example 15 Synthesis of Inv 364

A target compound Inv 364 (3.3 g, yield 58%) was obtained in the same manner as in Synthesis Example 2, except that Core4 (3.0 g, 12.13 mmol) was used instead of Core1.

GC-Mass (Theoretical value: 478.57 g / mol, Measured value: 478 g / mol)

Synthesis Example 16 Synthesis of Inv 376

Use Core4 (3.0g, 12.13mmol) instead of Core2, 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (instead of 4-bromo-N, N-diphenylaniline) 6.75 g, 14.55 mmol) was obtained in the same manner as in Synthesis Example 8 to obtain Inv 376 (4.9 g, yield 62%).

GC-Mass (Theoretical value: 630.76 g / mol, Measured value: 630 g / mol)

Synthesis Example 17 Synthesis of Inv 373

A target compound Inv 373 (3.8g, yield 57%) was obtained in the same manner as Synthesis Example 5 except for using Core4 (3.0 g, 12.13 mmol) instead of Core1.

GC-Mass (Theoretical value: 554.66 g / mol, Measured value: 554 g / mol)

Synthesis Example 18 Synthesis of Inv 451

A target compound Inv 451 (3.5 g, yield 59%) was obtained in the same manner as in Synthesis Example 3, except that Core5 (3.0 g, 12.97 mmol) was used instead of Core1.

GC-Mass (Theoretical value: 461.51 g / mol, Measured value: 461 g / mol)

Synthesis Example 19 Synthesis of Inv 455

Except for using 2- (4-chlorophenyl) -4,6-di (naphthalen-2-yl) -1,3,5-triazine (6.89g, 15.56mmol) instead of 4-chloro-2,6-diphenylpyrimidine Inv 455 (4.8 g, yield 58%) was obtained by the same procedure as in Synthesis Example 18.

GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)

Synthesis Example 20 Synthesis of Inv 467

Synthesis Example 8 Inv 467 (3.5 g, yield 62%) was obtained by the same procedure as the target compound.

GC-Mass (Theoretical value: 433.46 g / mol, Measured value: 433 g / mol)

Synthesis Example 21 Synthesis of Inv 212

Except for using 2-chloro-4-phenylquinazoline (2.82g, 11.75mmol) instead of 4-chloro-2-phenylpyrimidine was carried out in the same manner as in Synthesis Example 1 Inv 212 (3.0g, yield 61% )

GC-Mass (Theoretical value: 510.59 g / mol, Measured value: 510 g / mol)

Synthesis Example 22 Synthesis of Inv 216

The same procedure as in Synthesis Example 1 was conducted except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.3g, 11.75mmol) was used instead of 4-chloro-2-phenylpyrimidine. Inv 216 (3.4 g, yield 55%) was obtained as the target compound.

GC-Mass (Theoretical value: 636.74 g / mol, Measured value: 636 g / mol)

Synthesis Example 23 Synthesis of Inv 293

2-chloro-4- (4- (naphthalen-2-yl) phenyl) quinazoline (4.3 instead of 2,4-di (biphenyl-3-yl) -6- (4-chlorophenyl) -1,3,5-triazine g, 11.74 mmol) was obtained in the same manner as in Synthesis Example 13 to obtain Inv 293 (3.5 g, yield 57%) as a target compound.

GC-Mass (Theoretical value: 636.74 g / mol, Measured value: 636 g / mol)

Synthesis Example 24 Synthesis of Inv 383

Synthesis except using 4- (biphenyl-4-yl) -2-chloroquinazoline (3.84g, 12.13mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Inv 383 (3.3 g, yield 52%) was obtained by the same procedure as in Example 17.

GC-Mass (Theoretical value: 527.64 g / mol, Measured value: 527 g / mol)

[Examples 1 to 20] Fabrication of Green Organic Electroluminescent Device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and the device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Synthesis Example 1 to each compound + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) on the thus prepared ITO transparent substrate (electrode) The device was manufactured by laminating in order of / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

Comparative Example 1 Fabrication of Green Organic Electroluminescent Device

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

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , BCP and CBP used in Examples 1 to 20 and Comparative Example 1 are as follows.

[Evaluation Example 1]

The driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured for the green organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Example 1, and the results are shown in Table 1 below.

Table 1

Sample	Host	Drive voltage (V)	Light emitting peak (nm)	Current efficiency (cd / A)
Example 1	Inv-88	6.41	516	41.2
Example 2	Inv-106	6.57	517	42.3
Example 3	Inv-107	6.44	516	43.5
Example 4	Inv-141	6.73	514	45.6
Example 5	Inv-168	6.67	517	44.2
Example 6	Inv-199	6.65	516	43.3
Example 7	Inv-223	6.66	517	45.4
Example 8	Inv-225	6.73	517	41.5
Example 9	Inv-232	6.52	514	43.1
Example 10	Inv-233	6.53	516	45.2
Example 11	Inv-253	6.48	518	43.3
Example 12	Inv-274	6.48	517	43.6
Example 13	Inv-278	6.72	516	42.7
Example 14	Inv-284	6.80	517	43.3
Example 15	Inv-364	6.63	516	42.7
Example 16	Inv-376	6.75	516	42.8
Example 17	Inv-373	6.55	516	43.9
Example 18	Inv-451	6.63	518	41.3
Example 19	Inv-455	6.62	516	44.2
Example 20	Inv-467	6.51	516	41.4
Comparative Example 1	CBP	6.93	516	38.2

As shown in Table 1 above, the case where the compound of the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 20) was compared with the case where the conventional CBP was used for the light emitting layer of the green organic electroluminescent device (Comparative Example 1). It can be seen that the current efficiency and the driving voltage are excellent.

Examples 21 to 24 Fabrication of Red Organic Electroluminescent Device

After the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Synthesis Examples 21 to 24 + 10% (piq) ₂ Ir (acac) (30nm) / BCP 10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture a device.

Comparative Example 2 Fabrication of Red Organic Electroluminescent Device

A device was manufactured in the same manner as in Example 21, except that CBP was used instead of the compound of Synthesis Example 21 as a light emitting host material when forming the emission layer.

The structures of m-MTDATA, TCTA, BCP and CBP used in Examples 21 to 24 and Comparative Example 2 are as described above, and the structure of (piq) ₂ Ir (acac) is as follows.

[Evaluation Example 2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 21 to 24 and Comparative Example 2, and the results are shown in Table 2 below.

TABLE 2

Sample	Host	Drive voltage (V)	Current efficiency (cd / A)
Example 21	Inv-212	4.73	12.3
Example 22	Inv-216	4.68	13.1
Example 23	Inv-293	4.65	12.3
Example 24	Inv-383	4.69	12.9
Comparative Example 2	CBP	5.25	8.2

As shown in Table 2 above, when the compound of the present invention was used for the light emitting layer of the red organic electroluminescent device (Examples 21 to 24), the conventional CBP was used for the light emitting layer of the red organic electroluminescent device (Comparative Example 2). It can be seen that the current efficiency and the driving voltage are excellent.

The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.

Claims (8)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   R ₁ and R ₂ and R ₂ and R _3, at least one of which forms a condensed ring represented by formula (2),

   [Formula 2]

   

   In Chemical Formula 1,

   X ₁ is selected from the group consisting of CAr ₂ Ar ₃ , NAr ₄ , O, S and SiAr ₅ Ar ₆ ,

   R ₁ to R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ aryl amine, or by combining adjacent groups may form a fused ring,

   Ar ₁ to Ar ₆ are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 3 nuclear atoms 40 heterocycloalkyl groups, C ₆ -C ₆₀ aryl groups, heteroaryl groups of _5-60 nuclear atoms, C ₁ -C ₄₀ alkyloxy groups, C ₆ -C ₆₀ aryloxy groups, C ₃ -C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group,

   The alkyl group, alkenyl group, alkynyl group cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group of R ₁ to R ₁₀ and Ar ₁ to Ar ₆ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group , C ₃ ~ C ₄₀ cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group , C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group , C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl ring is a substituted or unsubstituted amine groups at least one member selected from the group consisting of.
2. The method of claim 1,

   Compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas 3 to 6:

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   In Chemical Formulas 3 to 6,

   X ₁ , R ₁ , R ₃ to R ₁₀ and Ar ₁ are as defined in claim ₁ .
3. The method of claim 1,

   X ₁ is NAr ₄ , O or S.
4. The method of claim 1,

   Ar ₁ to Ar ₆ are each independently composed of a C ₆ ~ C ₆₀ aryl group, a heteroaryl group of 5 to 60 nuclear atoms, a C ₆ ~ C ₄₀ arylamine group and a C ₆ ~ C ₄₀ arylsilyl group Compound selected from the group.
5. The method of claim 1,

   R ₁ to R ₁₀ are each independently hydrogen, halogen, and cyano group. A compound selected from the group consisting of a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
6. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,

   At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 5.
7. The method of claim 6,

   The organic light emitting device comprising the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and a light emitting layer.
8. The method of claim 7, wherein

   The organic material layer containing the compound is a light emitting layer,

   The compound is an organic electroluminescent device which is a phosphorescent host of the light emitting layer.