KR101418147B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel indoloacridine compound having excellent hole injecting and transporting ability and light emitting ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating it into one or more organic layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel acridine compound having excellent hole injection and transport ability, , A driving voltage, a lifetime, and the like.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film luminosity of Bernanose in the 1950s, (Tang) and a functional layer of a light emitting layer. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

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 light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting 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 such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. As the hole blocking layer and the electron transporting layer, NRMFPB, BCP, Alq ₃ and the like represented by the following formulas are widely known, and an anthracene derivative as a luminescent material is reported as a fluorescent dopant / host material. In particular Firpic, Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material _{(ppy) 3, (acac)} Ir (btp) 2 Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in organic EL devices.

Korea Public Patent 2011-0068330

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which has excellent hole injecting, transporting ability, and light emitting ability.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.

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

In this formula,

At least one of R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , and R ₆ and R ₇ forms a fused ring represented by Formula 2;

In the above formula, the dotted line represents a site where condensation is performed with the compound of Formula 1;

X is selected from the group consisting of NAr ₁ , O, S and SiAr ₂ Ar ₃ ;

Y ₁ to Y ₄ are each independently selected from CR ₁₄ or N;

R ₁ to R ₁₄ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group, a substituted or unsubstituted in the ring of the ring of the ring A C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group. , Wherein they form or are non-forming a fused ring with an adjacent group;

Ar ₁ to Ar ₃ are the same or different and each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkene group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group, a substituted or unsubstituted in the ring of the ring of the ring A C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group. Group, wherein they form or non-form a fused ring with adjacent groups.

In the above R ₁ to R ₁₄ and Ar ₁ to Ar ₃ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group , A C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C ₁ ~ C ₄₀ alkyl silyl group, the group is an aryl amine of the C ₆ ~ C ₆₀ aryl silyl group, or a C ₆ ~ C ₆₀ of each independently represents a deuterium, a halogen, a nitrile group, a nitro group, a cyano group, C ₁ ~ heterocycloalkyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ of, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, A C ₆ to C ₆₀ arylsilyl group and a C ₆ to C ₆₀ arylamine group ≪ / RTI >

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

At this time, the compound represented by Formula 1 may be used as a phosphorescent host or a hole transport layer of the light emitting layer.

The compound represented by formula (1) of the present invention can exhibit excellent heat resistance, hole injection and transport ability,

Therefore, an organic EL device including the compound represented by Formula 1 as a hole injection / transport layer or a phosphorescent / fluorescent host or dopant of a light emitting layer can be greatly improved in terms of light emitting performance, driving voltage, lifetime, efficiency, A full color display panel, and the like.

The present invention provides a novel compound having a higher molecular weight than conventional materials for organic EL devices [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)], and excellent driving voltage characteristics and efficiency.

According to the present invention, the compound represented by the general formula (1) is a compound in which a fused carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety, is connected to the indoloacridine group basic skeleton, The energy level is controlled by the substituent and thus has a broad band gap (sky blue to red). 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. In particular, the indoleacridine basic skeleton can exhibit excellent characteristics as a light emitting host material compared to conventional CBP.

Also, introduction of various aromatic ring substituents into the indoloacridine basic skeleton significantly increases the molecular weight of the compound, thereby enhancing the glass transition temperature and thus achieving higher thermal stability than conventional CBP. 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 the formula (1) of the present invention is employed as a hole injection / transport layer of an organic electroluminescence (EL) device, a blue, green and / or red phosphorescent host material or a fluorescent host material, It is possible to exert a remarkably excellent effect on the surface. 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 compound represented by the formula (1) according to the present invention, it is preferable that X is NAr ₁ considering wide band gap and thermal stability. Wherein Ar ₁ is an aryl group of C ₆ to C ₆₀ , or a heteroaryl group having 5 to 60 nuclear atoms.

In the above-mentioned NAr ₁ , the aryl group of C ₆ to C _{60 and} the heteroaryl group of 5 to 60 nucleus atoms are each independently selected from deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ A C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, may be substituted with one or more substituents selected from C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group and C ₆ ~ C ₆₀ aryl group consisting of amine groups of the.

In one example, the C ₆ ~ heteroaryl of C ₆₀ aryl group or a nuclear atoms of 5 to 60 of the group in Ar ₁ of the present invention, phenyl, naphthyl, indene, anthracene, phenanthrene, pyrene, triphenylene, pyridine, Benzothiophenes, benzimidazoles, benzothiazines, benzothiophenes, benzothiophenes, benzothiophenes, benzothiophenes, benzothiophenes, benzothiophenes, benzothiophenes, benzothiophenes, Azole, purine, and phenanthroline.

In the compounds represented by formula (1) according to the present invention, R ₁ to R ₁₄ are the same or different and each independently represents hydrogen, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl , A heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having ₆ to ₆₀ carbon atoms.

At this time, the C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ group is an aryl amine of the C _60, each independently selected from deuterium, halogen, C ₁ ~ of a C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 heteroaryl groups of 1 to 60, C ₁ ~ C ₄₀ of the alkyloxy, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, and a C ₆ ~ one or more substituents selected from the aryl group consisting of an amine group in the C ₆₀ . ≪ / RTI > In particular, R ₁₂ and R ₁₃ may be the same or different from each other, and each independently may be a C ₁ to C ₄₀ alkyl group, or a C ₆ to C ₆₀ aryl group. In this case, the C ₁ -C ₄₀ alkyl group and the C ₆ -C ₆₀ aryl group are preferably a methyl group or a phenyl group, respectively. More preferably, R ₁₂ and R ₁₃ are simultaneously the same substituent, such as a methyl group or a phenyl group. .

In the compounds represented by formula (I) according to the present invention, Y ₁ to Y ₄ may each independently be selected from CR ₁₄ or N, wherein Y ₁ to Y ₄ are each independently CR ₁₄ , or N is 1 Is preferably included.

In the compound of formula (I) according to the present invention, R ₁ to R ₁₄ and Ar ₁ to Ar ₃ may each independently be selected from the following substituent (functional group) groups.

According to the present invention, the compound represented by the general formula (1) can be further specified as the compound represented by the following general formulas (3) to (6).

In this formula,

Y ₁ to Y ₄ , R ₁ to R _{13, and} Ar ₁ are the same as defined in the above formula (1).

As described above, Ar ₁ is preferably a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, and Y ₁ to Y ₄ are each independently CR ₁₄ or N is preferably included.

The compounds of the formulas (3) to (6) according to the present invention may be further formulated by the following formulas (C-1) to (C-20).

In this formula,

R ₁ to R _{14 and} Ar ₁ are the same as defined in the formula (1).

On the other hand, when Y ₁ to Y ₄ in the illustrated compounds are all CR ₁₄ , each R ₁₄ may be fused with adjacent R ₁₄ to form a ring.

As used herein, "unsubstituted alkyl" refers to straight or branched chain saturated hydrocarbons having 1 to 40 carbon atoms, including but not limited to methyl, ethyl, propyl, isobutyl, sec- - Amyl, hexyl and the like.

"Unsubstituted aryl" means an aromatic moiety having from 6 to 60 carbon atoms, either alone or in combination with at least two rings. Where the 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 60 nuclear atoms in which at least one carbon, preferably one to three carbons, of the ring is replaced by N, O , S, or Se. Wherein 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.

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

According to the present invention described above, the compound represented by the formula (1) can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

The compound of formula (I) of the present invention can be synthesized according to a general synthesis method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

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 at least one organic layer sandwiched between (i) an anode, (ii) a cathode, and (iii) an anode and a cathode, wherein at least one Is one or more compounds represented by the formula (1).

Here, the organic material layer containing the compound represented by Formula 1 of the present invention 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 Formula 1 may be included in an organic electroluminescent device as a light emitting layer material. In this case, the organic electroluminescent device can improve the luminous efficiency, the luminance, the thermal efficiency of the power efficiency, and the lifetime of the device.

In particular, the compound represented by the formula (1) according to the present invention can be used as a phosphorescent host or a fluorescent host or a dopant material of the light emitting layer. Preferably, the compound represented by Formula 1 may be included in the organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

In addition, in the organic electroluminescent device according to the present invention, the organic compound layer other than the organic compound layer including the compound of Formula 1 may be a hole injecting layer, a hole transporting layer, a light emitting layer, and / or an electron transporting layer.

Non-limiting examples of the structure of the organic electroluminescent device according to the present invention include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. At this time, at least one of the hole injecting layer, the hole transporting layer and the light emitting layer may contain at least one compound represented by the above formula (1). In addition, the compound of the present invention can be used as a phosphorescent host or a fluorescent host of the luminescent layer. An electron injection layer may be disposed on the electron transport layer.

In addition, the organic EL device according to the present invention may have an insulating layer or an adhesive layer inserted into the interface between the electrode and the organic layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

In the organic electroluminescent device according to the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum evaporation 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 according to the present invention can be manufactured by using materials and methods known in the art, except that one or more of the organic layers are formed so as to include the compound represented by Formula 1 of the present invention. . ≪ / RTI >

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

Examples of the positive electrode material include 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 and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Preparation Example 1] Synthesis of IMC-1 and IMC-2

≪ Step 1 > 8,8- dimethyl -3- (2- nitrophenyl ) -8H- indolo [3,2,1- de ] Synthesis of acridine

18.11 g (50.0 mmol) of 3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine and 9.18 g (55.0 mmol) of 2-nitrophenylboronic acid, 6.00 g mmol) of NaOH and 200 ml / 100 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 2.90 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 15.37 g (yield: 76%) of the target compound, 8,8-dimethyl-3- (2-nitrophenyl) -8H- indolo [3,2,1- %).

^{1 H-NMR: δ 1.60 (} s, 6H), 7.32 (m, 6H), 7.63 (m, 1H), 8.01 (m, 6H), 8.17 (d, 1H)

<Step 2> IMC -1 and IMC Synthesis of -2

7.73 g (19.10 mmol) of 8,8-dimethyl-3- (2-nitrophenyl) -8H-indolo [3,2,1-de] acridine, 12.52 g (47.72 mmol) of triphenylphosphine, 1,2-dichlorobenzene And the mixture was stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ and 2.88 g (yield: 41%) of IMC-1 and 2.44 g (yield: 34.8%) of IMC-2 were obtained by column chromatography.

¹ H-NMR of IMC-1:? 1.60 (s, 6H), 7.33 (m, 8H), 7.55 (m, 3H), 7.99 )

¹ of IMC-2 H-NMR: δ 1.59 (s, 6H), 7.32 (m, 7H), 7.53 (m, 2H), 8.00 (m, 4H), 10.40 (s, 1H)

[Preparation Example 2] Synthesis of IMC-3 and IMC-4

&Lt; Step 1 > 8,8- dimethyl -3- (3- nitropyridine -2- yl ) -8H- indolo Synthesis of [3,2,1-de] acridine

3-nitropyridin-2-one was obtained by following the procedure of <Step 1> of Preparation Example 1, except that 3-nitropyridin-2-ylboronic acid was used in place of 2-nitrophenylboronic acid. -yl) -8H-indolo [3,2,1-de] acridine.

^{1 H-NMR: δ 1.60 (} s, 6H), 7.35 (m, 7H), 8.01 (m, 2H), 8.37 (m, 2H), 8.78 (m, 2H)

<Step 2> IMC -3 and IMC Synthesis of -4

8,8-dimethyl-3- (3-nitropyridin-2-yl) -8H-indolo [3,2,1-d] acridine instead of 8,8-dimethyl- 3- (2- nitrophenyl) 3,2,1-de] acridine was used in place of the compound of Preparation Example 1, to obtain the desired compounds IMC-3 and IMC-4.

¹ H-NMR of IMC-3: 隆 1.59 (s, 6H), 7.32 (m, 5H), 7.47 (m, 4H), 7.97 (m, 2H), 8.38 )

¹ H-NMR of IMC-4: 隆 1.59 (s, 6H), 7.34 (m, 5H), 7.48 (m, 2H), 7.99 (m, 4H), 8.39 )

[Preparation Example 3] Synthesis of IMC-5 and IMC-6

Step 1 Preparation of 8,8-dimethyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -8H-indolo [3,2,1-de] acridine synthesis

23.2 g (0.064 mol) of 3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine was reacted with 4,4,4 ', 4', 5,5,5 ' 24.29 g (0.096 mol) of 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane), 2.6 g (5 mol%) of Pd (dppf) Cl ₂ , 18.76 g And the mixture was stirred at 130 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO ₄ . The solvent removed was subjected to column chromatography to obtain the target compound, 8,8-dimethyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 3,2,1-de] acridine (yield: 52%).

¹ H-NMR:? 1.24 (s, 24H), 1.76 (s, 6H), 7.25 (m, 3H), 7.42

Step 2 Synthesis of 3- (6-chloro-3-nitropyridin-2-yl) -8,8-dimethyl-8H-indolo [3,2,1-de] acridine

3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine and 2-nitrophenylboronic acid in place of 8,8-dimethyl- 3- (4,4,5,5-tetramethyl- Step 1 of Preparation Example 1 was repeated except that 2,2-dioxaborolan-2-yl) -8H-indolo [3,2,1-de] acridine and 2,6-dichloro- (6-chloro-3-nitropyridin-2-yl) -8,8-dimethyl-8H-indolo [3,2,1-de] acridine.

^{1 H-NMR: δ 1.75 (} s, 6H), 7.24 (m, 3H), 7.41 (m, 4H), 7.94 (d, 1H), 8.11 (m, 2H), 8.64 (m, 2H)

<Step 3> IMC -5 and IMC Synthesis of -6

3- (6-chloro-3-nitropyridin-2-yl) -8,8-dimethyl-3- (2- nitrophenyl) -8H- indolo [3,2,1- The procedure of Step 2 of Preparation Example 1 was followed except that 8H-indolo [3,2,1-de] acridine was used to obtain the target compounds IMC-5 and IMC-6.

¹ H-NMR of IMC-5: 1.74 (s, 6H), 7.25 (m, 4H), 7.41 (m, 4H), 7.55 (s, ), 10.49 (s, 1 H)

Of ^{IMC-6 1 H-NMR:} δ 1.74 (s, 6H), 7.31 (m, 4H), 7.40 (m, 3H), 7.94 (m, 3H), 8.40 (d, 1H), 10.48 (s, 1H )

[Preparation Example 4] Synthesis of IMC-7 and IMC-8

&Lt; Step 1 > 3- (3- nitropyridine -2- yl ) -8,8- 피덴 -8H- indolo Synthesis of [3,2,1-de] acridine

Using 3-bromo-8,8-diphenyl-8H-indolo [3,2,1-de] acridine instead of 3-bromo-8,8-dimethyl-8H-indolo [3,2,1- 3-nitropyridin-2-yl) -8,8-diphenyl-8H-indolo [3,2,1-de] pyridine was obtained by following the procedure of <Step 1> of Preparation Example 1, acridine.

^{1 H-NMR: δ 7.22 (} m, 12H), 7.39 (m, 5H), 8.00 (m, 2H), 8.30 (m, 2H), 8.68 (m, 2H)

<Step 2> IMC -7 and IMC Synthesis of -8

(3-nitropyridin-2-yl) -8,8-diphenyl-8H-indolo [3,2-d] acridine in place of 8,8-dimethyl- 3- (2- nitrophenyl) 3,2,1-de] acridine was used in place of the compound of Preparation Example 1 to obtain the desired compounds IMC-7 and IMC-8.

¹ H-NMR of IMC-7: 隆 7.23 (m, 10H), 7.38 (m, 8H), 7.55 (s, 1H), 7.99 (m, 2H), 8.41 )

¹ H-NMR of IMC-8:? 7.22 (m, 10H), 7.37 (m, 7H), 8.00 (m, 4H), 8.41

[Preparation Example 5] Synthesis of IMC-9 and IMC-10

&Lt; Step 1 > 8,8- dimethyl -6- (2- nitrophenyl ) -8H- indolo [3,2,1- de ] Synthesis of acridine

Using 6-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine instead of 3-bromo-8,8-dimethyl-8H-indolo [ 8-dimethyl-6- (2-nitrophenyl) -8H-indolo [3,2,1-de] acridine was obtained by following the procedure of <Step 1> of Preparation Example 1,

¹ H-NMR:? 1.72 (s, 6H), 7.35 (m, 5H), 7.56 (m, 4H), 8.01

<Step 2> IMC -7 and IMC Synthesis of -8

8,8-dimethyl-6- (2-nitrophenyl) -8H-indolo [3,2-b] pyridine instead of 8,8-dimethyl- 3- (2- nitrophenyl) -8H- 1-de] acridine was used in place of the compound of Preparation Example 1 to obtain the desired compounds IMC-9 and IMC-10.

¹ H-NMR of IMC-9:? 1.72 (s, 6H), 7.33 (m, 7H), 7.58 (m, 4H), 8.11

¹ H-NMR:? 1.72 (s, 6H), 7.37 (m, 6H), 7.57 (m, 4H), 8.19 (m, 3H), 10.42

[ Synthetic example  One] AC Synthesis of -1

IMC-1 (4.95 g, 13.29 mmol), 2-bromo-4,6-diphenylpyridine (8.24 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol), K ₂ CO ₃ (3.66 g, 26.57 mmol), Na ₂ SO ₄ (3.78 g, 26.57 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, the residue was purified by column chromatography to obtain the desired compound AC-1 (4.64 g, yield 58%).

GC-Mass (theory: 601.74 g / mol, measurement: 601 g / mol)

[ Synthetic example  2] BIA Synthesis of -2

IMC-1 (2.18 g, 5.85 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10 g, 7.85 mmol), NaH g, 8.78 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into water and the solid compound was filtered and purified by column chromatography to obtain the target compound AC-2 (3.00 g, yield 85%).

GC-Mass (theory: 603.71 g / mol, measurement: 603 g / mol)

[ Synthetic example  3] AC Synthesis of -3

Except that 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl- (3.29 g, yield 78%) was obtained by carrying out the same procedure as in Synthesis Example 2 above.

GC-Mass (calculated: 755.91 g / mol, measured: 755 g / mol)

[ Synthetic example  4] AC Synthesis of -4

AC-4 (5.04 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that IMC-2 was used instead of IMC-1.

GC-Mass (theory: 601.74 g / mol, measurement: 601 g / mol)

[Synthesis Example 5] Synthesis of AC-5

AC-5 (2.93 g, yield 82%) was obtained in the same manner as in Synthesis Example 2, except that IMC-2 was used instead of IMC-1.

GC-Mass (theory: 603.71 g / mol, measurement: 603 g / mol)

[Synthesis Example 6] Synthesis of AC-6

AC-6 (3.37 g, yield 80%) was obtained in the same manner as in Synthesis Example 3, except that IMC-2 was used instead of IMC-1.

GC-Mass (calculated: 755.91 g / mol, measured: 755 g / mol)

[ Synthetic example  7] AC Synthesis of -7

AC-7 (4.72 g, yield 59%) was obtained in the same manner as in Synthesis Example 1, except that IMC-3 was used instead of IMC-1.

GC-Mass (theory: 602.73 g / mol, measurement: 602 g / mol)

[ Synthetic example  8] AC Synthesis of -8

AC-8 (2.96 g, yield 81%) was obtained in the same manner as in Synthesis Example 2, except that IMC-3 was used instead of IMC-1.

GC-Mass (theory: 604.70 g / mol, measurement: 604 g / mol)

[ Synthetic example  9] AC Synthesis of -9

AC-9 (3.52 g, yield 83%) was obtained in the same manner as in Synthesis Example 3, except that IMC-3 was used instead of IMC-1.

GC-Mass (calculated: 756.89 g / mol, measured: 756 g / mol)

[ Synthetic example  10] AC Synthesis of -10

AC-7 (5.08 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that IMC-4 was used instead of IMC-1.

GC-Mass (theory: 602.73 g / mol, measurement: 602 g / mol)

[ Synthetic example  11] AC Synthesis of -11

AC-11 (2.85 g, yield 80%) was obtained in the same manner as in Synthesis Example 2, except that IMC-4 was used instead of IMC-1.

GC-Mass (theory: 604.70 g / mol, measurement: 604 g / mol)

[ Synthetic example  12] AC Synthesis of -12

AC-12 (3.31 g, yield 78%) was obtained in the same manner as in Synthesis Example 3, except that IMC-4 was used instead of IMC-1.

GC-Mass (calculated: 756.89 g / mol, measured: 756 g / mol)

[ Synthetic example  13] AC Synthesis of -13

The mixture was stirred with IMC-5 (3.21 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 / Then, 0.46 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C, and the mixture was 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. The solvent of the obtained organic layer was removed and then purified by column chromatography to obtain IMC-5-1 (3.01 g, yield 85%) as an intermediate compound.

AC-13 (3.00 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that IMC-5-1 was used instead of IMC-1.

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[ Synthetic example  14] AC Synthesis of -14

AC-14 (3.99 g, yield: 88%) was obtained in the same manner as in Synthesis Example 2, except that IMC-5-1 was used instead of IMC-1.

GC-Mass (theory: 680.80 g / mol, measurement: 680 g / mol)

[ Synthetic example  15] AC Synthesis of -15

AC-15 (3.35 g, yield 74%) was obtained in the same manner as in Synthesis Example 3, except that IMC-5-1 was used instead of IMC-1.

GC-Mass (calculated: 832.99 g / mol, measured: 832 g / mol /)

[ Synthetic example  16] AC Synthesis of -16

AC-16 (2.94 g, yield 64%) was obtained in the same manner as in Synthesis Example 13, except that pyridin-3-ylboronic acid was used in place of phenylboronic acid.

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[ Synthetic example  17] AC Synthesis of -17

AC-17 (3.66 g, yield 80%) was obtained in the same manner as in Synthesis Example 14, except that pyridin-3-ylboronic acid was used in place of phenylboronic acid.

GC-Mass (calculated: 681.79 g / mol, measured: 681 g / mol)

[ Synthetic example  18] AC Synthesis of -18

AC-18 (3.47 g, yield 74%) was obtained in the same manner as in Synthesis Example 15, except that pyridin-3-ylboronic acid was used in place of phenylboronic acid.

GC-Mass (calculated: 833.98 g / mol, measured: 833 g / mol)

[ Synthetic example  19] AC -19 Synthesis

AC-19 (3.00 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 13, except that IMC-6 was used instead of IMC-5.

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[ Synthetic example  20] AC Synthesis of -20

AC-20 (3.92 g, yield 86%) was obtained in the same manner as in Synthesis Example 14, except that IMC-6 was used instead of IMC-5.

GC-Mass (theory: 680.80 g / mol, measurement: 680 g / mol)

[ Synthetic example  21] AC Synthesis of -21

AC-21 (3.53 g, yield 79%) was obtained in the same manner as in Synthesis Example 15, except that IMC-6 was used instead of IMC-5.

GC-Mass (calculated: 832.99 g / mol, measured: 832 g / mol)

[ Synthetic example  22] AC Synthesis of -22

AC-22 (2.97 g, yield 67%) was obtained by carrying out the same procedure as in Synthesis Example 16, except that IMC-6 was used instead of IMC-5.

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[ Synthetic example  23] AC Synthesis of -23

AC-23 (3.87 g, yield 84%) was obtained by carrying out the same procedure as in Synthesis Example 17, except that IMC-6 was used instead of IMC-5.

GC-Mass (calculated: 681.79 g / mol, measured: 681 g / mol)

[ Synthetic example  24] AC Synthesis of -24

AC-24 (3.61 g, yield 78%) was obtained in the same manner as in Synthesis Example 18, except that IMC-6 was used instead of IMC-5.

GC-Mass (calculated: 833.98 g / mol, measured: 833 g / mol)

[ Synthetic example  25] AC Synthesis of -25

AC-25 (3.88 g, yield: 61%) was obtained in the same manner as in Synthesis Example 1, except that IMC-7 was used instead of IMC-1.

GC-Mass (calculated: 726.86 g / mol, measured: 726 g / mol)

[ Synthetic example  26] AC Synthesis of -26

AC-26 (4.66 g, yield 85%) was obtained in the same manner as in Synthesis Example 2, except that IMC-7 was used instead of IMC-1.

GC-Mass (calculated: 728.84 g / mol, measured: 728 g / mol)

[ Synthetic example  27] AC -27

AC-27 (4.32 g, yield 76%) was obtained in the same manner as in Synthesis Example 3, except that IMC-7 was used instead of IMC-1.

GC-Mass (calculated: 881.03 g / mol, measured: 881 g / mol)

[ Synthetic example  28] AC -28 Synthesis

AC-28 (3.91 g, yield 62%) was obtained in the same manner as in Synthesis Example 1, except that IMC-8 was used instead of IMC-1.

GC-Mass (calculated: 726.86 g / mol, measured: 726 g / mol)

[ Synthetic example  29] AC Synthesis of -29

AC-29 (4.61 g, yield 84%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that IMC-8 was used instead of IMC-1.

GC-Mass (calculated: 728.84 g / mol, measured: 728 g / mol)

[ Synthetic example  30] AC Synthesis of -30

AC-30 (4.24 g, yield 74%) was obtained in the same manner as in Synthesis Example 3, except that IMC-8 was used instead of IMC-1.

GC-Mass (calculated: 881.03 g / mol, measured: 881 g / mol)

[ Synthetic example  31] AC Synthesis of -31

AC-31 (4.48 g, yield 82%) was obtained in the same manner as in Synthesis Example 2, except that IMC-9 was used instead of IMC-1.

GC-Mass (theory: 603.71 g / mol, measurement: 603 g / mol)

[ Synthetic example  32] AC Synthesis of -32

AC-30 (4.35 g, yield 77%) was obtained by carrying out the same procedure as in Synthesis Example 3, except that IMC-9 was used instead of IMC-1.

GC-Mass (calculated: 755.91 g / mol, measured: 755 g / mol)

[Synthesis Example 33] Synthesis of AC-33

AC-32 (4.51 g, yield 85%) was obtained in the same manner as in Synthesis Example 2, except that IMC-10 was used instead of IMC-1.

GC-Mass (theory: 603.71 g / mol, measurement: 603 g / mol)

[ Synthetic example  34] AC Synthesis of -34

AC-34 (4.01 g, yield 70%) was obtained in the same manner as in Synthesis Example 3, except that IMC-10 was used instead of IMC-1.

GC-Mass (calculated: 755.91 g / mol, measured: 755 g / mol)

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

The compounds AC-1 to AC-34 synthesized in Synthesis Example 1-34 were subjected to high-purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated 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.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / AC-1 to AC-34 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in that order.

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 fabricated in the same manner as in Example 1, except that CBP was used instead of the compound AC-1 as a luminescent host material in forming the light emitting layer.

[Evaluation example]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm &lt; 2 &gt; were measured for each green organic EL device manufactured in Example 1-34 and Comparative Example 1, .

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 AC-1 6.48 515 40.0 Example 2 AC-2 6.86 518 41.8 Example 3 AC-3 6.61 517 44.2 Example 4 AC-4 6.51 515 41.7 Example 5 AC-5 6.77 518 41.5 Example 6 AC-6 6.46 515 43.9 Example 7 AC-7 6.71 518 41.0 Example 8 AC-8 6.76 517 43.4 Example 9 AC-9 6.57 515 44.1 Example 10 AC-10 6.86 518 41.4 Example 11 AC-11 6.61 515 42.2 Example 12 AC-12 6.81 518 43.1 Example 13 AC-13 6.74 515 41.1 Example 14 AC-14 6.46 518 42.0 Example 15 AC-15 6.71 515 42.5 Example 16 AC-16 6.79 518 41.3 Example 17 AC-17 6.55 518 41.9 Example 18 AC-18 6.68 516 43.0 Example 19 AC-19 6.71 515 40.7 Example 20 AC-20 6.63 518 41.3 Example 21 AC-21 6.81 517 41.5 Example 22 AC-22 6.76 515 41.1 Example 23 AC-23 6.83 518 42.5 Example 24 AC-24 6.81 517 43.1 Example 25 AC-25 6.76 515 39.2 Example 26 AC-26 6.48 518 41.3 Example 27 AC-27 6.86 515 42.9 Example 28 AC-28 6.79 518 39.6 Example 29 AC-29 6.87 515 40.9 Example 30 AC-30 6.79 518 41.6 Example 31 AC-31 6.88 517 40.8 Example 32 AC-32 6.91 517 40.7 Example 33 AC-33 6.69 517 40.5 Example 34 AC-34 6.83 518 40.4 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compounds (AC-1 to AC-34) according to the present invention were used as a light emitting layer of a green organic EL device (Example 1-34) It can be seen that it shows better performance in terms of efficiency and driving voltage as compared with Example 1).

Claims (10)

A compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , and one of R ₆ and R ₇ form a condensed ring represented by the following formula 2;
(2)

In this formula,
X is selected from the group consisting of NAr ₁ , O, S and SiAr ₂ Ar ₃ ;
Y ₁ to Y ₄ are each independently selected from CR ₁₄ or N;
R ₁ to R ₁₄ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group, a substituted or unsubstituted in the ring of the ring of the ring A C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group. Group, wherein they form or are non-forming a condensed ring with adjacent groups;
Ar ₁ to Ar ₃ are the same or different and each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkene group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group, a substituted or unsubstituted in the ring of the ring of the ring A C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group. , Wherein they form or are non-forming a condensed ring with adjacent groups;
In the above R ₁ to R ₁₄ and Ar ₁ to Ar ₃ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ ~ C ₄₀ heterocycloalkyl 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 of the, C ₆ ~ aryloxy C _60, C _A halogen atom, a nitrile group, a nitro group, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group or a C ₆ to C ₆₀ arylamine group, the alkyl group, C an alkenyl group of _{2 ~ C 40, C 1 ~} C 40 alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ of the ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ - the one that is C ₆₀ aryl group and a C ₆ ~ silyl selected from the group consisting of C ₆₀ aryl amine of It is substituted or unsubstituted with. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (6)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

Wherein Y ₁ to Y ₄ , R ₁ to R ₁₃ , and Ar ₁ are as defined in Formula (1). 3. The compound according to claim 2, wherein the compound of the formulas (3) to (6) is selected from the group consisting of the following formulas C-1 to C-20.

In the above formulas, R ₁ to R _{14 and} Ar ₁ are as defined in formula (1). 4. The method of claim 3, wherein Ar ₁ is selected from the group consisting of heteroaryl group of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60,
The aryl group of C ₆ to C _{60 and} the heteroaryl group of 5 to 60 nucleus atoms are each independently selected from the group consisting of deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, a nuclear atom the number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group and a C An arylamine group having ₆ to ₆₀ carbon atoms, or an arylamine group having ₆ to ₆₀ carbon atoms. The compound according to claim 3, wherein R ₁ to R ₁₄ are each independently selected from the group consisting of hydrogen, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl, And an arylamine group of C ₆ to C ₆₀ ,
The C ₁ to C ₄₀ alkyl group, the C ₆ to C ₆₀ aryl group, the heteroaryl group having 5 to 60 nuclear atoms, and the arylamine group having ₆ to ₆₀ carbon atoms are each independently selected from the group consisting of deuterium, halogen, A C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ alkoxy group, ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl group and a C ₆ ~ silyl substituted with one or more selected from the group consisting of C ₆₀ aryl amine, or compounds characterized in that unsubstituted. The compound according to claim 3, wherein R ₁₂ and R ₁₃ are the same or different and are each independently a C ₁ to C ₄₀ alkyl group or a C ₆ to C ₆₀ aryl group. An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound of the formula (1) according to any one of claims 1 to 6. The organic electroluminescent device according to claim 7, wherein the organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer. The organic electroluminescent device according to claim 7, wherein the compound represented by Formula 1 is used as a phosphorescent host of the light emitting layer. The organic electroluminescent device according to claim 7, wherein the compound represented by Formula 1 is used as a hole transport layer in the light emitting layer.