KR20150038811A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. According to the present invention, the compound is used in an organic layer of the organic electroluminescent device, desirably a light emitting layer, a hole transport layer, an electron blocking layer, or a light emitting auxiliary layer, thereby improving light emitting efficiency, driving voltage, life, etc of the organic electroluminescent device.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device including the same. More specifically, the present invention relates to a novel indole compound having excellent electron blocking ability, hole transport ability, and light emitting 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, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to improve the efficiency and lifetime of the organic EL device, the organic EL device has been developed to introduce a characteristic organic material layer in the device, and the development of specialized materials used thereon has been continued.

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

The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a 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 phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq ₃ and the like represented by the following chemical formulas are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, it is still required to eliminate the efficiency loss in terms of the luminous efficiency of the conventional light emitting materials, and the lifetime is not satisfactory.

Japanese Patent Application Laid-Open No. 2001-160489

It is an object of the present invention to provide a novel compound which is excellent in luminous efficiency, hole transporting ability and electron blocking ability, and can improve luminous efficiency when used together with a light emitting material.

Another object of the present invention is to provide an organic electroluminescent device including the novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

Y ₁ and Y ₂ are the same as or different from each other and each independently N or CR _11, wherein when CR ₁₁ is plural, they are the same or different,

R ₁ and R ₂ , R ₂ and R ₃ , or one of R ₃ and R ₄ are bonded to each other to form a condensed ring represented by the following formula (2)

X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ Selected,

Provided that at least one of X ₁ and X ₂ is N (Ar ₁ ), and when N (Ar ₁ ) is plural, they are the same or different,

Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyl A substituted or unsubstituted aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ - group of the C ₄₀ alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine It is selected from oxide group and a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group consisting of an amine group,

Provided that at least one of the at least one Ar ₁ is a substituent represented by the following formula (3)

L is a single bond, or a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms, or may be a group selected from the group consisting of A condensed aromatic ring or a condensed heteroaromatic ring,

R _a and R _b are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or may be a group selected from the group consisting of A condensed aromatic ring or a condensed heteroaromatic ring,

R ₁ to R ₄ of which does not form a condensed ring of the general formula (2) as R ₅ to R ₈ and R ₁₁ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted hwandoen C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group of the number of ring 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ ~ C ₆₀ of A substituted or unsubstituted aryloxy 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 aryloxy group, A substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkylboron group, a substituted or unsubstituted A C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₆₀ Aryl phosphine oxide group is selected from the pin, and the group consisting of substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine;

The alkyl group, cycloalkyl group, heterocyclic alkyl group, aryl group and heteroaryl group of the R _a and R _{b and} the alkyl group of Ar ₁ to Ar ₅ , R ₁ to R ₈ , and R ₁₁ , An aryloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an aryl group such as an aryloxy group, an aryloxy group, amine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear A heteroaryl group having 5 to 60 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, group C ₂ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and the C An arylamine group having ₆ to ₆₀ carbon atoms, or a substituted or unsubstituted arylamine group having ₆ to ₆₀ carbon atoms,

When a plurality of substituents are present, they may be the same or different.

Also, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers is a compound represented by the above- And an organic electroluminescent device.

The one or more organic layers including the compound represented by Formula 1 may be a light emitting layer, a hole transporting layer, an electron blocking layer, or a light emitting auxiliary layer. Here, the compound of Formula 1 may be a light emitting layer, a hole transporting layer material, or a light emitting auxiliary layer material.

Since the compound according to the present invention is excellent in heat resistance, light emitting ability, hole transporting ability, electron blocking ability and the like, it can be used as an organic material layer material of an organic electroluminescence device, preferably as a light emitting layer material, a hole transporting layer, .

In addition, the organic electroluminescent device including the compound according to the present invention in the light emitting layer, the hole transporting layer, or the light emitting auxiliary layer can greatly improve aspects of light emitting performance, driving voltage, lifetime, efficiency, Can be effectively applied.

Hereinafter, the present invention will be described.

1. Compound

The organic compound according to the present invention is a compound in which the substituent of the above formula (3), such as a diarylamine moiety, a diheteroaryl moiety and the like, is added at the N position of a core in which an indole-based moiety, (Such as an aryl group) bonded to the basic skeleton through a direct bond or through a linking group (e.g., arylene group) to form a basic skeleton, . The compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device materials such as NPB, BCP and CBP, has a high glass transition temperature and is excellent in thermal stability, and has a light emitting property, a hole transporting ability, great. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

In the compound represented by Formula 1, the indole moiety in the core has a high singlet energy level and a high triplet energy level (2.5 eV or more) while having excellent hole transporting ability. The substituent of the above formula (3) such as a diarylamine moiety, a diheteroaryl moiety and the like is introduced to the N position of the core. The substituent of the above formula (3) has excellent hole transporting ability. Accordingly, since the hole mobility of the compound of Formula 1 is higher than that of NPB, the compound of Formula 1 can be used as a hole transporting layer material of the organic electroluminescent device or a light emitting auxiliary layer material assisting the hole transport of the hole transporting layer.

In addition, in the case of implementing the phosphorescent device by using the compound represented by the above formula (1) as a light emitting auxiliary layer material between the hole transporting layer and the light emitting layer, the compound of the above formula (1) It is possible to limit the injection into the relevant layer. At the same time, since the compound of Formula 1 has the delta Est property of 0.5 eV or less, the triplet exciton is shifted to the singlet level by the compound of Formula 1, which is then transited to the singlet level of the light emitting layer, And as a result, it is transferred to the triplet level of the light emitting layer, and the light emitting efficiency of the phosphorescent light emitting layer can be increased. In addition, since the compound of formula (1) has a high LUMO value, it has excellent electron blocking function.

In addition, the compounds of the present invention can be used to enhance the efficiency of a fluorescent blue element. The compound of Formula 1 has a hole mobility higher than that of NPB, and a triplet energy level higher than that of the blue fluorescent light-emitting layer. Accordingly, the compound of Formula 1 can prevent the triplet exciton from flowing into the emitter layer, restrict the triplet exciton in the light emitting layer, and convert the triplet exciton into singlet exciton through TTA (TTF) . In addition, the compound of Formula 1 can improve the interface characteristics between the hole-related layer and the light emitting layer, such as the hole injecting layer and the hole transporting layer.

In addition, the compound of formula (1) has various substituents, especially aryl groups, introduced into the basic skeleton, and the molecular weight of the compound is significantly increased, thereby improving the glass transition temperature. As a result, BCP, CBP). ≪ / RTI >

Thus, the compound represented by Formula 1 can improve the phosphorescence characteristics of the organic electroluminescent device and improve the hole transporting ability, electron blocking ability, luminous efficiency, driving voltage, lifetime characteristics, and the like. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics, and further, the performance of the full-color organic light emitting panel can be maximized.

The compound represented by the formula (1) according to the present invention is a compound represented by the following formula (4), wherein _one of R ₁ and R ₂ , R ₂ and R ₃ , or R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the formula To < RTI ID = 0.0 > 9. ≪ / RTI >

In the above Chemical Formulas 4 to 9,

X ₁ , X ₂ , Y ₁ , Y _2, and R ₁ to R ₈ are the same as defined in Formula 1, respectively.

The compound represented by formula (1) of the present invention may be represented by any one of the following formulas (1-1) to (1-42).

In Formulas 1-1 to 1-42,

Ar ₁ , R ₁ to R ₈ and R ₁₁ are as defined in the above formula (1)

When a plurality of Ar < ₁ > s are the same or different from each other,

When R < ₁₁ > is plural, they are the same as or different from each other.

In the compound of Formula 1, Y ₁ and Y ₂ are the same as or different from each other, and each independently N or CR _11, wherein when CR ₁₁ is plural, they are the same or different from each other.

Further, X ₁ and X ₂ are the same or different, each independently consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) Lt; / RTI >

Preferably, X ₁ is O, S or N (Ar ₁ ), X ₂ can be N (Ar ₁ ), and more preferably X ₁ and X ₂ can all be N (Ar ₁ ). At this time, when a plurality of N (Ar ₁ ) s are present, they may be the same or different.

Provided that at least one of the at least one Ar ₁ is a substituent represented by the above formula (3).

In Formula 3, L is a single bond or a group selected from the group consisting of a phenylene group, a biphenylene group, a fluorenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, It is preferably selected from the group consisting of a quinolinylene group and a carbazolylene group or a group capable of forming a condensed aromatic ring or a condensed heteroaromatic ring by bonding with an adjacent group, Or a biphenylene group, or may be bonded to an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring.

In the L, the phenylene group, the biphenylene group, the fluorenylene group, the naphthylene group, the pyridinylene group, the pyrimidinylene group, the quinolinylene group and the carbazolylene group are each independently substituted with deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ of the C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, the C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, 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 ~ substituted by one or more substituents selected from the aryl group consisting of an amine group in the C ₆₀ or beach . However, when there are a plurality of substituents, they may be the same or different.

In formula (3), R _a and R _b each independently represent a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group a pyrimidinyl group, a quinolyl group, and a carbazolyl group, or may be bonded to an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring.

In this case, the R group in the _a and R _b, biphenyl group, fluorenyl group, a naphthyl group, a pyridyl group, a pyrimidine group, a quinolyl group and carbazolyl groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ the alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ of the C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ substituted with a boron group, C ₆ ~ C ₆₀ aryl phosphine group, at least one substituent selected from the group consisting of group C ₆ ~ C ₆₀ aryl phosphine oxide group, and an aryl amine of the C ₆ ~ C ₆₀ of or may be unsubstituted. However, when there are a plurality of substituents, they may be the same or different.

Examples of the substituent represented by the above formula (3) include, but are not limited to, the following substituents U1 to U91.

In the compound of Formula 1, R ₁ to R ₄ , which do not form the condensed ring of Formula 2, and R ₅ to R ₈ and R ₁₁ , which are the same or different, are each independently hydrogen, C ₆ to C ₆₀ , And a heteroaryl group having 5 to 60 nuclear atoms are preferable.

In this case, the R ₁ to R as that of which does not form a condensed ring represented by the above formula 2 _4, R ₅ to R _8, and aryl group in R _11, heteroaryl group each independently selected from deuterium, halogen, cyano, C ₁ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic alkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted . However, when there are a plurality of substituents, they may be the same or different.

In Formula 1, at least one of R ₅ to R ₈ may be a substituent represented by Formula 10 below.

In Formula 10,

L ₁ is a single bond, or a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms, preferably a single bond Or a phenylene group or a biphenylene group,

X ₃ is O, S, Se, N ( Ar 6), C (Ar 7) (Ar 8) and Si (Ar ₉₎ is selected from the group consisting of (Ar _10), preferably O, S or N ( Ar ₆ ), more preferably N (Ar ₆ )

Ar ₆ to Ar ₁₀ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyl A substituted or unsubstituted aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ - group of the C ₄₀ alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine An oxy group and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group,

R ₂₁ to R ₂₆ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, 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, a C ₃ to C ₄₀ An arylsilyl group of C ₆ to C ₆₀ , a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ An arylphosphine oxide group and an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,

The arylene group and a heteroarylene group, Ar ₆ to Ar ₁₀ and R ₂₁ to R ₂₆ represents an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl in the L ₁ A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C group ₁ ~ C ₄₀ alkyl silyl, C ₆ ~ C group ₆₀ aryl silyl group, an alkyl boronic of C ₂ ~ C ₄₀ of, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ with an aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a substituent at least one selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of When unsubstituted or may be unsubstituted, wherein the substituent is a plurality, they may be the same or different from each other.

The substituent represented by the formula (10) may be a substituent represented by any one of the following formulas (10a) to (10h).

[Chemical Formula 10a]

[Chemical Formula 10b]

[Chemical Formula 10c]

[Chemical Formula 10d]

[Chemical Formula 10e]

[Formula 10f]

[Chemical Formula 10g]

[Chemical Formula 10h]

In the above formulas (10a) to (10g)

X ₃ and R ₂₁ To R ₂₆ Are each as defined in Formula 10,

R ₂₇ to R ₂₉ are the same or different and each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, A cycloalkyl 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, a C ₃ to C ₄₀ alkyl A silyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ aryl A phosphine oxide group and an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed aromatic ring or condensed heteroaromatic ring,

n is an integer of 0 to 2,

m is an integer of 0 to 5;

More specific examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the following compounds C 1 to C 139.

As used herein, "unsubstituted alkyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

As used herein, "unsubstituted alkenyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. do. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

As used herein, "unsubstituted alkynyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. do. Non-limiting examples thereof include ethynyl, 2-propynyl, and the like.

As used herein, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

As used herein, "unsubstituted heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon , Preferably one to three carbons, is substituted with a heteroatom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.

As used herein, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

The "unsubstituted heteroaryl" used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, , One to three carbons are substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

As used herein, "unsubstituted alkyloxy" means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic ) Structure. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

As used herein, "unsubstituted aryloxy" means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

As used herein, the term "unsubstituted alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, an arylsilyl means a silyl substituted with an aryl having 6 to 60 carbon atoms, Lt; RTI ID = 0.0 > 60 < / RTI >

As used herein, "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

More particularly, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers A compound represented by the formula (1), preferably a compound represented by any one of the formulas (4) to (9). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron transporting layer and an electron injecting layer. . ≪ / RTI > Preferably, one or more organic layers including the compound of Formula 1 may be selected from the group consisting of a light emitting layer, a hole transporting layer, and a light emitting auxiliary layer. Here, the light-emission-assisting layer can assist the hole transport in the hole transport layer while blocking electrons, and assist the light emission of the light-emitting layer to improve the light-emitting efficiency.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially stacked . Here, the electron injection layer and / or the hole blocking layer may be further stacked on the electron transporting layer.

In addition, the organic electroluminescent device according to the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between the electrode and the organic layer.

The organic electroluminescent device according to the present invention can be produced by a method known in the art, except that at least one of the organic material layers, preferably a light emitting layer, a hole transporting layer and / or a light emitting auxiliary layer, Can be prepared by using the materials and methods.

The organic material layer 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.

A silicon wafer, a quartz or glass plate, a metal plate, a plastic film, a sheet, or the like may be used as the substrate used in manufacturing the organic electroluminescent device of the present invention, but the present invention is not limited thereto.

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 may be used, but the present invention is 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 blocking layer, the light emitting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and 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 illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound IC-1

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

(25 g, 0.128 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (48.58 g , 0.191 mol), mixed with _{Pd (dppf) Cl 2 (5.2} g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and 130 ℃ Lt; / RTI &gt; for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ , and the residue was purified by column chromatography to obtain 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 1H-indole (22.32 g, yield 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.27 (d, IH), 7.42 s, 1 H)

<Step 2> Synthesis of 5- (2-nitrophenyl) -1H-indole

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol), NaOH (9.05 g, 226.24 mmol) and THF / H ₂ O, and then, Pd (PPh ₃₎ in 40 ℃ ₄ (4.36 g mixture of (400 ml / 200 ml) , 5 mol%) were added, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 5- (2-nitrophenyl) -1H-indole (11.32 g, yield 63%).

^{1 H-NMR: δ 6.47 (} d, 1H), 7.25 (d, 1H), 7.44 (d, 1H), 7.53 (d, 1H), 7.65 (t, 1H), 7.86 (t, 1H), 7.95 ( (s, 1 H), 8.00 (d, 1 H), 8.09 (t,

<Step 3> Synthesis of 5- (2-nitrophenyl) -1-phenyl-1H-indole

Indole (11 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), K ₂ CO ₃ (6.38 g, 46.17 mmol), Na ₂ SO ₄ (6.56 g, 46.17 mmol), and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and the residue was purified by column chromatography to obtain 5- (2-nitrophenyl) -1-phenyl-1H-indole (10.30 g, yield 71%).

^{1 H-NMR: δ 6.48 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 3H), 7.55 (m, 4H), 7.63 (t, 1H), 7.84 (t, 1H), 7.93 ( s, 1 H), 8.01 (d, 1 H), 8.11 (t, 1 H)

<Step 4> Synthesis of Compound IC-1

Phenyl-1H-indole (5 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2-dichlorobenzene (50 ml ) Were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography to obtain a compound IC-1 (2.38 g, yield 53%).

^{1 H-NMR: δ 6.99 (} d, 1H), 7.12 (t, 1H), 7.27 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.50 (d, 1H), 7.60 ( (d, IH), 8.05 (d, IH)

[ Preparation Example  2] Compound IC Synthesis of -2

<Step 1> Synthesis of 5-bromo-1-phenyl-1H-indole

Except that 5-bromo-1H-indole (9.05 g, 46.17 mmol) was used instead of 5- (2-nitrophenyl) -1H-indole used in Step 3 of Preparation Example 1, Step 3>, 5-bromo-1-phenyl-1H-indole (12.6 g, yield 74%) was obtained.

^{1 H-NMR: δ 6.73 (} d, 1H), 7.18 (d, 1H), 7.33 (m, 2H), 7.43 (m, 3H), 7.51 (m, 3H)

<Step 2> Synthesis of 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole

1-phenyl-1H-indole (20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78 g, 88.18 mmol) and K ₂ CO ₃ 30.47 g, 220.47 mmol) and THF / H ₂ O (400 ml / 100 ml) were added and stirred. Pd (PPh ₃₎ at 40 ℃ into the ₄ (2.54 g, 2.204mmol) was stirred under reflux at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then the target compound, 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18 g, yield: 72%) was obtained by column chromatography.

¹ H-NMR:? 6.52 (d 1H), 7.55 (m, 4H), 8.70 (m, 4H)

<Step 3> Synthesis of 7-chloro-3-phenyl-3,10-dihydropyrrolo [3,2-a]

5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18 g, 51.60 mmol) obtained in the above Step 2 was dissolved in a mixture of triphenylphosphine (33.84 g, dichlorobenzene (200 ml) and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and an organic layer was extracted with dichloromethane. The extracted organic layer was dried with MgSO ₄ and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and 7-chloro-3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (10 g, yield: 62%) was obtained by column chromatography.

^{1 H-NMR: δ 6.55 (} d, 1H), 7.12 (d, 1H), 7.55 (m, 8H), 8.02 (d, 2H), 10.23 (s, 1H)

<Step 4> Synthesis of Compound IC-2

7-chloro-3-phenyl-3 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H- indole used in Step 2 of Preparation Example 1 was used instead of 5- Phenyl-3- (4,4,5,5-tetramethyl-1, 3-dihydropyrrolo [3,2-a] carbazole (5 g, 15.78 mmol) was used instead of 1-bromo- 2-yl) -9H-carbazole (8.74 g, 23.67 mmol) was used in place of the compound IC-2 (5.21 g, , Yield: 63%).

¹ H-NMR:? 6.55 (d, 1H), 7.58 (m, 14H), 8.05 (m, 9H)

[Preparation Example 3] Synthesis of Compound IC-3

Instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in <Step 4> of Preparation Example 2, The compound IC-3 (5.32 g, yield: 71%) was prepared in the same manner as in <Step 4> of Preparation Example 2 except that -9H-fluoren-3-ylboronic acid (5.64 g, 23.67 mmol) ).

^{1 H-NMR: δ 1.75 (} s, 6H), 6.52 (d, 1H), 7.31 (m, 2H), 7.50 (m, 4H), 7.58 (m, 5H), 7.67 (m, 2H), 7.87 ( m, 2 H), 8.00 (m, 3 H), 10.24 (s, 1 H)

[Preparation Example 4] Synthesis of Compound IC-4

Instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in <Step 4> of Preparation Example 2, dibenzo [b, 4-ylboronic acid (5.02 g, 23.67 mmol) was used in place of 4-chloro-4-fluorobenzaldehyde to obtain the compound IC-4 (5.38 g, yield: 76%) .

^{1 H-NMR: δ 6.53 (} d, 1H), 7.33 (m, 3H), 7.49 (m, 3H), 7.58 (m, 3H), 7.63 (m, 2H), 7.87 (m, 4H), 8.02 ( m, 3 H), 10.23 (s, 1 H)

[Preparation Example 5] Synthesis of Compound IC-5

Instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in <Step 4> of Preparation Example 2, dibenzo [b, (7.33 g, yield: 72%) was obtained by carrying out the same procedure as <Step 4> of Preparation Example 2, except that thiophen-4-ylboronic acid (5.40 g, 23.67 mmol) .

^{1 H-NMR: δ 6.53 (} d, 1H), 7.34 (m, 3H), 7.51 (m, 2H), 7.58 (m, 4H), 7.63 (m, 2H), 7.88 (m, 3H), 8.01 ( m, 4H), 10.23 (s, 1 H)

[Preparation Example 6] Synthesis of compound IC-6

<Step 1> Synthesis of 1- (biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole

Step 3 of Preparation Example 1 was repeated except that 4-bromobiphenyl (16.14 g, 69.26 mmol) was used instead of iodobenzene used in Step 3 of Preparation Example 1 to prepare 1- (biphenyl- 4-yl) -5- (2-nitrophenyl) -1H-indole (13.52 g, yield 75%).

^{1 H-NMR: δ 6.48 (} d, 1H), 7.27 (d, 1H), 7.46 (m, 7H), 7.53 (m, 5H), 7.63 (t, 1H), 7.83 (t, 1H), 7.99 ( m, 2 H), 8.12 (t, 1 H)

&Lt; Step 2 > IC Synthesis of -6

(Biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole obtained in Step 1 was used instead of 5- (2-nitrophenyl) (4.51 g, yield: 79%) was obtained by carrying out the same procedure as <Step 4> of Preparation Example 1, except that 1-indole (6.21 g, 15.91 mmol) .

^{1 H-NMR: δ 6.49 (} d, 1H), 7.27 (t, 1H), 7.32 (d, 1H), 7.45 (m, 5H), 7.52 (m, 2H), 7.60 (m, 5H), 7.85 ( d, 1 H), 8.00 (d, 1 H), 10.45 (s, 1 H)

[Preparation Example 7] Synthesis of compound IC-7

Step 1 Synthesis of biphenyl-4-yl) -N- (4- (5- (2-nitrophenyl) -1H-indol-1- yl) phenyl) biphenyl-4-amine

Except that N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine (33.00 g, 69.26 mmol) was used instead of iodobenzene used in Step 3 of Preparation Example 1, (Biphenyl-4-yl) -N- (4- (5- (2-nitrophenyl) -1H-indol-1-yl) phenyl) biphenyl- 4-amine (18.43 g, yield: 63%).

LC-Mass: 633 g / mol

Elemental Analysis: C, 83.39; H, 4.93; N, 6.63; O, 5.05

<Step 2> Synthesis of Compound IC-7

(Biphenyl-4-yl) -N- (4- (2-nitrophenyl) -1-phenyl-1H-indole obtained in Step 1 was used instead of 5- Step 4 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -1 H-indol-1-yl) phenyl) biphenyl-4-amine (6.21 g, 15.91 mmol) To obtain compound IC-7 (5.84 g, yield: 61%).

LC-Mass: 601 g / mol

Elemental Analysis: C, 87.82; H, 5.19; N, 6.98

[Synthesis Example 1] Synthesis of Compound C 1

(2.82 g, 10.00 mmol), 4-bromo-N, N-diphenylaniline (3.89 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol) prepared in Preparation Example 1 (t-Bu) ₃ P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 50 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the solution was filtered with MgSO ₄ . The solvent was removed from the filtered organic layer, and the desired compound C 1 (3.73 g, yield 71%) was obtained by column chromatography.

LC-Mass: 525 g / mol

[Synthesis Example 2] Synthesis of Compound C 3

Except that N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine (5.72 g, 12.00 mmol) was used in place of 4-bromo-N, N- diphenylaniline used in Synthesis Example 1 , The target compound C 3 (4.87 g, yield 72%) was obtained in the same manner as in Synthesis Example 1.

LC-Mass: 677 g / mol

[Synthesis Example 3] Synthesis of Compound C 5

(Biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (6.20 g, , 12.00 mmol), the target compound C 5 (5.52 g, yield 77%) was obtained in the same manner as in Synthesis Example 1.

LC-Mass: 717 g / mol

[Synthesis Example 4] Synthesis of Compound C 12

Except that N, N-di (biphenyl-4-yl) -4'-bromobiphenyl-4-amine (6.63 g, 12.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline used in Synthesis Example 1 Was subjected to the same procedure as in Synthesis Example 1 to give the desired compound C 12 (5.27 g, yield 70%).

LC-Mass: 753 g / mol

[Synthesis Example 5] Synthesis of Compound C14

(Biphenyl-4-yl) -N- (4'-bromobiphenyl-4-yl) -9,9-dimethyl-9H-fluorene- 2, instead of the 4-bromo-N, N- diphenylaniline used in Synthesis Example 1 -amine (7.11 g, 12.00 mmol), the target compound C 14 (5.39 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 1.

LC-Mass: 793 g / mol

[Synthesis Example 6] Synthesis of Compound C 20

Except that N, N-di (biphenyl-4-yl) -3'-bromobiphenyl-4-amine (6.63 g, 12.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline used in Synthesis Example 1 , The target compound C 20 (5.35 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 1.

LC-Mass: 753 g / mol

[Synthesis Example 7] Synthesis of Compound C21

(Biphenyl-4-yl) -N- (3'-bromobiphenyl-4-yl) -9,9-dimethyl-9H-fluorene- 2 as a starting material instead of the 4-bromo-N, N- diphenylaniline used in Synthesis Example 1 -amine (7.11 g, 12.00 mmol) was used in place of N, N-dimethylformamide (5 mL) to obtain the target compound C21 (5.41 g, yield 69%).

LC-Mass: 793 g / mol

[Synthesis Example 8] Synthesis of Compound C 24

Except that N, N-di (biphenyl-4-yl) -4'-bromobiphenyl-3-amine (6.63 g, 12.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline used in Synthesis Example 1 Was subjected to the same procedure as in Synthesis Example 1 to obtain C24 (5.42 g, yield 73%) as a target compound.

LC-Mass: 753 g / mol

[Synthesis Example 9] Synthesis of Compound C 25

(Biphenyl-4-yl) -N- (4'-bromobiphenyl-3-yl) -9,9-dimethyl-9H-fluorene- 2 as a ligand instead of 4-bromo- N, diphenylaniline used in Synthesis Example 1 -amine (7.11 g, 12.00 mmol) was used in place of the compound obtained in Preparation Example 1 to obtain the target compound C 25 (5.41 g, yield 69%).

LC-Mass: 793 g / mol

[Synthesis Example 10] Synthesis of Compound C 28

Except that N, N-di (biphenyl-4-yl) -3'-bromobiphenyl-3-amine (6.63 g, 12.00 mmol) was used instead of 4-bromo-N, N-diphenylaniline used in Synthesis Example 1 , The target compound C28 (5.42 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 1.

LC-Mass: 753 g / mol

[Synthesis Example 11] Synthesis of Compound C 29

(Biphenyl-4-yl) -N- (3'-bromobiphenyl-3-yl) -9,9-dimethyl-9H-fluorene- 2 -amine (7.11 g, 12.00 mmol), the target compound C 29 (5.45 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1.

LC-Mass: 793 g / mol

[Synthesis Example 12] Synthesis of Compound C36

The procedure of Synthesis Example 4 was repeated except that the compound IC-2 (5.23 g, 10.00 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 4, (6.56 g, yield 66%).

LC-Mass: 994 g / mol

[Synthesis Example 13] Synthesis of Compound C37

The procedure of Synthesis Example 5 was repeated except that the compound IC-2 (5.23 g, 10.00 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 4, (6.41 g, yield 62%).

LC-Mass: 1034 g / mol

[Synthesis Example 14] Synthesis of Compound C 56

The procedure of Synthesis Example 4 was repeated except that the compound IC-3 (4.74 g, 10.00 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 4 to obtain the target compound C 56 (6.81 g, yield 72%).

LC-Mass: 945 g / mol

[Synthesis Example 15] Synthesis of Compound C 57

The procedure of Synthetic Example 5 was repeated except that the compound IC-3 (4.74 g, 10.00 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthetic Example 5 to obtain the target compound C 57 (6.90 g, yield 70%).

LC-Mass: 985 g / mol

[Synthesis Example 16] Synthesis of Compound C 76

The procedure of Synthetic Example 4 was repeated except that the compound IC-4 (4.48 g, 10.00 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthetic Example 4 to obtain the target compound C 76 (7.17 g, yield 78%).

LC-Mass: 919 g / mol

[Synthesis Example 17] Synthesis of Compound C77

The procedure of Synthesis Example 5 was repeated except that the compound IC-4 (4.48 g, 10.00 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 5 to obtain the target compound C 77 (6.81 g, yield 71%).

LC-Mass: 959 g / mol

[Synthesis Example 18] Synthesis of Compound C 96

The procedure of Synthesis Example 4 was repeated except that the compound IC-5 (4.64 g, 10.00 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 4, (6.73 g, yield 72%).

LC-Mass: 935 g / mol

[Synthesis Example 19] Synthesis of Compound C97

The procedure of Synthesis Example 5 was repeated except that the compound IC-5 (4.64 g, 10.00 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 5, (6.53 g, yield 67%).

LC-Mass: 975 g / mol

[Synthesis Example 20] Synthesis of Compound C 112

The procedure of Synthesis Example 3 was repeated except that the compound IC-6 (3.58 g, 10.00 mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 3 to obtain the target compound C 112 6.19 g, yield 78%).

LC-Mass: 793 g / mol

[Synthesis Example 21] Synthesis of Compound C 121

(2.80 g, 12.00 mmol) instead of 4-bromo-N, N-diphenylaniline was used instead of the compound IC-7 (6.01 g, 10.00 mmol) synthesized in Preparation Example 7 instead of the compound IC- mmol), the target compound C 121 (5.35 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 1.

LC-Mass: 753 g / mol

[Example 1] Production of green organic electroluminescent device

Compound C-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / compound C 1 (40 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq on the ITO transparent electrode prepared above. ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[Examples 2 to 21] Preparation of green organic electroluminescent device

An organic EL device was manufactured in the same manner as in Example 1 except that the compound synthesized in Synthesis Examples 2 to 21 was used instead of the compound C 1 in Example 1.

[ Comparative Example  1] Green organic Field  Manufacturing of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound C 1 was not used in Example 1.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Example 1, respectively, and the results are shown in Table 1 below .

Emitting material The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 C 1 6.95 519 42.1 Example 2 C 3 6.80 521 42.0 Example 3 C 5 6.80 520 42.1 Example 4 C 12 6.90 519 42.0 Example 5 C 14 6.95 520 41.8 Example 6 C 20 6.95 521 42.0 Example 7 C 21 6.80 518 42.1 Example 8 C 24 6.85 521 41.9 Example 9 C 25 6.85 520 42.0 Example 10 C 28 6.90 519 41.9 Example 11 C 29 6.95 519 41.8 Example 12 C 36 6.85 518 42.0 Example 13 C 37 6.90 520 42.1 Example 14 C 52 6.90 519 41.9 Example 15 C 53 6.80 521 41.5 Example 16 C 76 6.95 520 41.9 Example 17 C 77 6.90 521 42.2 Example 18 C 96 6.85 522 42.1 Example 19 C 97 6.95 519 41.7 Example 20 C 112 6.90 522 42.0 Example 21 C 121 6.80 521 42.3 Comparative Example 1 - 6.93 516 38.2

As shown in Table 1, the green organic electroluminescent devices (the green organic electroluminescent devices manufactured in Examples 1 to 21, respectively) using the compound represented by Formula 1 according to the present invention as the light emitting auxiliary layer material, The driving voltage was similar to that of the green organic electroluminescent device (green organic electroluminescent device of Comparative Example 1) in which only the conventional CBP was used as the material of the light emitting layer without the layer. However, compared with the green organic electroluminescent device of Comparative Example 1, It can be further improved.

[Example 22] Preparation of red organic electroluminescent device

The compound synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. 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.

(60 nm) / TCTA (80 nm) / Compound C 1 (40 nm) / CBP + 10% (piq) ₂ Ir (acac) (300 nm) / The organic electroluminescent device was fabricated by stacking BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

The structures of m-MTDATA, TCTA, CBP and BCP used are as described in Example 1 and (piq) ₂ Ir (acac) is as follows.

[ Example  23 ~ 42] Red organic Field  Manufacturing of light emitting device

A red organic EL device was manufactured in the same manner as in Example 22 except that the compound synthesized in Synthesis Examples 2 to 21 was used instead of the compound C 1 in Example 22.

[Comparative Example 2] Production of red organic electroluminescent device

A red organic electroluminescent device was manufactured in the same manner as in Example 21 except that the compound C 1 was not used in Example 22.

[ Evaluation example  2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each red organic electroluminescent device fabricated in Examples 22 to 42 and Comparative Example 2, and the results are shown in Table 2 below.

Emitting material The driving voltage (V) Current efficiency (cd / A) Example 22 C 1 5.10 10.9 Example 23 C 3 5.20 11.1 Example 24 C 5 5.25 10.6 Example 25 C 12 5.25 10.7 Example 26 C 14 5.20 11.2 Example 27 C 20 5.30 11.2 Example 28 C 21 5.20 11.1 Example 29 C 24 5.15 10.8 Example 30 C 25 5.20 11.1 Example 31 C 28 5.25 10.5 Example 32 C 29 5.30 10.8 Example 33 C 36 5.20 11.2 Example 34 C 37 5.20 11.1 Example 35 C 52 5.25 11.0 Example 36 C 53 5.10 11.2 Example 37 C 76 5.25 11.3 Example 38 C 77 5.20 10.8 Example 39 C 96 5.30 10.5 Example 40 C 97 5.25 11.0 Example 41 C 112 5.21 11.3 Example 42 C 121 5.30 10.9 Comparative Example 1 _ 5.25 8.2

As shown in Table 2, the red organic electroluminescent devices (red organic electroluminescent devices manufactured in Examples 22 to 42, respectively) using the compound represented by Formula 1 according to the present invention as the light emitting auxiliary layer material, The organic electroluminescent device was similar to the red organic electroluminescent device of Comparative Example 2 except that the driving voltage was similar to that of the red organic electroluminescent device of Comparative Example 2, .

[Example 43] Production of blue organic electroluminescent device

The compound synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. 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.

(15 nm) / ADN + 5% DS-405 (Doosan) (manufactured by Doosan Heavy Industries, Ltd.) on the ITO transparent electrode prepared above 300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The BCP used is as described in Example 1, and the structures of NPB and ADN are as follows.

[Examples 44 to 63] Preparation of blue organic electroluminescent device

A blue organic EL device was fabricated in the same manner as in Example 43 except that the compound synthesized in Synthesis Examples 2 to 21 was used instead of the compound C 1 in Example 43.

[Comparative Example 3] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 43 except that the compound C 1 was not used in Example 43.

[ Evaluation example  3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 43 to 63 and Comparative Example 3, and the results are shown in Table 3 below.

Emitting material The driving voltage (V) Current efficiency (cd / A) Example 43 C 1 5.58 7.1 Example 44 C 3 5.55 6.8 Example 45 C 5 5.62 6.5 Example 46 C 12 5.60 7.2 Example 47 C 14 5.50 6.7 Example 48 C 20 5.50 7.0 Example 49 C 21 5.60 6.5 Example 50 C 24 5.55 6.7 Example 51 C 25 5.55 6.9 Example 52 C 28 5.60 6.8 Example 53 C 29 5.60 6.4 Example 54 C 36 5.50 6.6 Example 55 C 37 5.50 6.0 Example 56 C 52 5.65 6.8 Example 57 C 53 5.55 7.1 Example 58 C 76 5.60 6.8 Example 59 C 77 5.60 7.5 Example 60 C 96 5.55 7.0 Example 61 C 97 5.51 7.1 Example 62 C 112 5.50 6.9 Example 63 C 121 5.55 6.8 Comparative Example 1 - 5.6 4.8

As shown in Table 3, the blue organic electroluminescent devices (blue organic electroluminescent devices manufactured in Examples 43 to 63, respectively) using the compound represented by Formula 1 according to the present invention as the light emitting auxiliary layer material, The organic electroluminescent device of Comparative Example 3 had a similar driving voltage to that of the conventional blue organic electroluminescent device (Comparative Example 3) without the layer, but the current efficiency could be further improved as compared with the organic electroluminescent device of Comparative Example 3. [

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (10)

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

(In the formula 1,
Y ₁ and Y ₂ are the same as or different from each other and each independently N or CR _11, wherein when CR ₁₁ is plural, they are the same or different,
R ₁ and R ₂ , R ₂ and R ₃ , or one of R ₃ and R ₄ are bonded to each other to form a condensed ring represented by the following formula (2)
(2)

X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ Selected,
Provided that at least one of X ₁ and X ₂ is N (Ar ₁ ), and when N (Ar ₁ ) is plural, they are the same or different, and Ar ₁ to Ar ₅ are the same or different from each other, or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group of the number of ring nucleus atoms of 3 to 40, a substituted or unsubstituted C ₆ ~ of C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group can be unsubstituted nuclear atoms of 5 to 60, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted aryloxy group, a substituted or unsubstituted Substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl groups, substituted or unsubstituted C ₆ to C ₆₀ arylsilyl groups, substituted or unsubstituted C ₁ to C ₄₀ alkylboron groups, substituted or unsubstituted C ₆ to C _A substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group It is selected from the side group and a substituted or unsubstituted C ₆ ~ aryl group consisting of an amine group of the C _60,
Provided that at least one of the at least one Ar ₁ is a substituent represented by the following formula (3)
(3)

L is a single bond, or a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms, or may be a group selected from the group consisting of A condensed aromatic ring or a condensed heteroaromatic ring,
R _a and R _b are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or may be a group selected from the group consisting of A condensed aromatic ring or a condensed heteroaromatic ring,
R ₁ to R ₄ of which does not form a condensed ring of the general formula (2) as R ₅ to R ₈ and R ₁₁ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted hwandoen C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group of the number of ring 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ ~ C ₆₀ of A substituted or unsubstituted aryloxy 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 aryloxy group, A substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkylboron group, a substituted or unsubstituted A C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₆₀ Aryl phosphine oxide group is selected from the pin, and the group consisting of substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine;
The alkyl group, cycloalkyl group, heterocyclic alkyl group, aryl group and heteroaryl group of the above R _a and R _{b and} the alkyl group of Ar ₁ to Ar ₅ , R ₁ to R ₈ and R ₁₁ , An alkoxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine Each of which is independently selected from the group consisting of deuterium, halogen, cyano, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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, a C ₆ ~ C ₆₀ aryl silyl group, C of ₂ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C substituted with at least ₆₀ aryl selected from the group consisting of amine groups, or one kind of substituent may be unsubstituted, wherein when the substituent is plural, they may be the same or different from each other). The method according to claim 1,
Wherein the compound represented by the formula (1) is a compound represented by any one of the following formulas (4) to (9):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

(In the above formulas 4 to 9,
X ₁ , X ₂ , Y ₁ , Y ₂ and R ₁ to R ₈ are each as defined in claim 1. The method according to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-42:

(In the above Formulas 1-1 to 1-42,
Ar ₁ , R ₁ to R ₈ and R ₁₁ are as defined in claim 1,
When a plurality of Ar &lt; ₁ &gt; s are the same or different from each other,
And when R &lt; ₁₁ &gt; is plural, they are the same or different from each other). The method according to claim 1,
Wherein the substituent represented by Formula 3 is selected from the group consisting of Substituents U1 to U91 below.

The method according to claim 1,
And at least one of R ₅ to R ₈ is a substituent represented by the following formula (10).
[Chemical formula 10]

In Formula 10,
L ₁ is a single bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms,
X ₃ Is selected from the group consisting of O, S, Se, N ( Ar 6), C (Ar 7) (Ar 8) and _{Si (Ar 9) (Ar 10} ),
Ar ₆ to Ar ₁₀ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyl A substituted or unsubstituted aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ - group of the C ₄₀ alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine It is selected from oxide group, and a substituted or unsubstituted C ₆ ~ the group consisting of an aryl amine of the C ₆₀ ring,
R ₂₁ to R ₂₆ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, 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, a C ₃ to C ₄₀ An arylsilyl group of C ₆ to C ₆₀ , a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ An arylphosphine oxide group and an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed aromatic ring or a condensed heteroaromatic ring,
In the above L ₁ arylene group and a heteroarylene group, Ar ₆ to Ar ₁₀ and R ₂₁ to R ₂₆ represents an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, aryl silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C alkyl group of _{1 ~ C 40, C 3 ~} C 40 a cycloalkyl group, a nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl of nuclear atoms of 5 to 60 aryl group, an alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₂ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine being substituted with one or more substituents selected from the group consisting of Or where the substituents are plural, they may be the same or different. 6. The method of claim 5,
Wherein the substituent represented by the formula (10) is a substituent represented by any one of the following formulas (10a) to (10h).
[Chemical Formula 10a]

[Chemical Formula 10b]

[Chemical Formula 10c]

[Chemical Formula 10d]

[Chemical Formula 10e]

[Formula 10f]

[Chemical Formula 10g]

[Chemical Formula 10h]

In the above formulas (10a) to (10g)
X ₃ and R ₂₁ to R ₂₆ are each as defined in claim 5,
R ₂₇ to R ₂₉ are the same or different and each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, A cycloalkyl 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, a C ₃ to C ₄₀ alkyl A silyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ aryl A phosphine oxide group and an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed aromatic ring or condensed heteroaromatic ring,
n is an integer of 0 to 2,
and m is an integer of 0 to 5). The method according to claim 1,
X ₁ and X ₂ are both N (Ar ₁ )
The plurality of N (Ar ₁ ) s may be the same or different from each other,
Wherein Ar &_lt; 1 _&gt; is as defined in claim 1. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds C 1 to C 139.

An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 8. 10. The method of claim 9,
Wherein at least one organic compound layer containing the compound is a light emitting layer, a hole transporting layer, or a light emitting auxiliary layer.