KR20180034925A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a compound having excellent light emitting ability and electron transporting ability, and to an organic electroluminescent device having enhanced characteristics such as light emitting efficiency, driving voltage and life by comprising at least one compound in an organic layer.

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 light emitting compound and an organic electroluminescent device using the same.

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, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known. Anthracene derivatives as a luminescent material have been 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.

Also, in Korean Patent Laid-Open Publication No. 2014-0069199, a carbazole derivative is disclosed as a matrix material for a dopant in a fluorescent or phosphorescent organic electroluminescent device.

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.

Korean Patent Publication No. 10-2014-0069199

The present invention is excellent in heat resistance, electron injecting ability, electron transporting ability, light emitting ability and the like, and can be used as an organic layer material of an organic electroluminescent device, specifically, a light emitting layer material, a life improving layer material, The present invention also provides a novel compound which can be used as an active ingredient.

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.

An example of the present invention provides a compound represented by the following Formula 1:

In Formula 1,

X ₁ and X ₂ are different from each other and each independently selected from the group consisting of N (Ar ₁ ), O, S and P (= O) Ar _{2 wherein} one of X ₁ and X ₂ is P ) Ar ₂ ,

Y ₁ to Y ₁₂ are the same or different and each independently N or C (R ₁ ), wherein when R ₁ is plural, they are the same or different,

Ar ₁ to Ar 2 are the same or different and each independently represents 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 , 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 A group selected from the group consisting of C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₆₀ aryl boron groups and C ₆ to C ₆₀ aryl amine groups, and may form a condensed ring by bonding with adjacent groups,

R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl , 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 aryl A silyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, and a C ₆ to C ₆₀ arylamine group, or may be bonded to an adjacent group to form a condensed ring ,

The alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group and the aryl group of Ar ₁ , Ar ₂ and R ₁ , arylamine groups are each independently a heavy hydrogen (D), a halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 of the An 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 Arylsulfonyl group, arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylboron group, and C ₆ to C ₆₀ arylamine group, which may be substituted or unsubstituted with at least one substituent selected from the group consisting of The substituent may be bonded to adjacent groups to form a condensed ring. When the substituent is plural, they may be the same or different from each other. Can.

In addition, one example of 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 represented by the above- An organic electroluminescent device comprising the compound represented by Formula

According to an embodiment of the present invention, the one or more organic layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Emitting layer or an electron transporting layer.

According to another example of the present invention, the one or more organic layers may include a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. At this time, the one or more organic layers including the compound represented by Formula 1 is a light-emitting auxiliary layer.

According to another embodiment of the present invention, the one or more organic layers may include a hole injection layer, a hole transport layer, a light emitting layer, a water surface improving layer, an electron transport layer, and an electron injection layer. At this time, one or more organic layers including the compound represented by Formula 1 is a life improving layer.

The compound represented by the formula (1) according to an example of the present invention is excellent in heat resistance, electron injecting ability, electron transporting ability, and light emitting ability, and can be used as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound according to an example of the present invention can greatly improve aspects of light emitting performance, driving voltage, lifetime, electron transport ability, lifetime, efficiency, and the like, .

Hereinafter, the present invention will be described.

1. New compound

A novel organic compound according to an exemplary embodiment of the present invention is a compound in which a 5-membered heteroaromatic ring moiety or an indole moiety condensed with benzene is condensed with dibenzoazepin (5H-dibenzo [b, f] azepine) And is represented by the above formula (1) having a ring structure containing a hetero structure containing phosphine oxide having excellent electron transporting ability and long life. The compound represented by Chemical Formula 1 has a higher molecular weight than conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], and thus has a high glass transition temperature, But it has excellent electron transporting ability and light emitting ability. 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.

Generally, in the phosphorescent light emitting layer of the organic electroluminescent device, the triplet energy gap of the host material must be higher than the triplet energy gap of the dopant. That is, when the lowest excitation state of the host is higher in energy than the lowest emission state of the dopant, the phosphorescence efficiency can be improved. The compound of Formula 1 has a triplet energy of 2.3 eV or higher. The compound represented by the above formula (1) has a structure in which an indole derivative having a singlet energy level and a triple energetic energy level having a broad basic skeleton are condensed, and a structure in which a specific substituent is introduced into the basic skeleton So that the energy level can be controlled to be higher than that of the dopant and can be used as a host material.

Further, since the compound according to one example of the present invention has a high triplet energy as described above, the excitons generated in the light emitting layer can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Therefore, when an organic layer (hereinafter, referred to as 'light emission-assisting layer') is formed between the hole transporting layer and the light emitting layer using the compound of Formula 1, the diffusion of the excitons is prevented by the compound, Unlike the conventional organic electroluminescent device not including the blocking layer, the number of the excitons contributing to light emission in the light emitting layer substantially increases, and the light emitting efficiency of the device can be improved. Also, when an organic material layer (hereinafter, referred to as a 'life improving layer') is formed between the light emitting layer and the electron transporting layer by using the compound of Formula 1, the diffusion of the exciton is prevented by the compound of Formula 1, The durability and stability of the light emitting element can be improved, and the half life of the element can be efficiently increased. Thus, the compound represented by Formula 1 may be used as a light-emitting auxiliary layer material or a life improving layer material in addition to the host of the light emitting layer.

In addition, the compound of Formula 1 can control the HOMO and LUMO energy levels according to the type of the substituent introduced into the basic skeleton, and can have a wide band gap and a high carrier transporting property. For example, when the electron donating group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, Since it has a bipolar characteristic, the bonding force between holes and electrons can be increased. As described above, the compound of Formula 1 in which EWG is introduced into the basic skeleton is excellent in carrier transportability and luminescence properties, and thus can be used as an electron injection / transport layer material or a life improving layer material in addition to the light emitting layer material of an organic electroluminescence device. . On the other hand, when the electron donor compound (EDG) is bonded to the basic skeleton of the compound of Formula 1 such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, etc., It can be usefully used as a hole injecting / transporting layer or a light emitting auxiliary layer material in addition to the light emitting layer material.

As described above, the compound represented by Formula 1 can improve the luminescent characteristics of the organic electroluminescent device and improve the hole injecting / transporting ability, the electron injecting / transporting ability, the light emitting efficiency, the driving voltage, . Accordingly, the compound of Chemical Formula (1) according to an embodiment of the present invention can be used as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / Emitting layer material, a light-emission-assisting layer material, a life-improving layer material, more preferably a light-emitting layer material, an electron-injecting layer material, a light-

In addition, the compound of formula (1) has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the basic skeleton and the molecular weight of the compound is significantly increased, thereby improving the glass transition temperature. And may have a higher thermal stability than the material (e.g., CBP). The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer. Accordingly, the organic electroluminescent device including the compound of Formula 1 according to an embodiment of the present invention can greatly improve performance and lifetime characteristics, and the full-color organic electroluminescent panel to which such an organic electroluminescent device is applied can also maximize the performance .

In the compound represented by Formula 1 according to an example of the present invention, X ₁ and X ₂ are different from each other and each independently selected from the group consisting of N (Ar ₁ ), O, S, and P (= O) Ar ₂ , Wherein one of X ₁ and X ₂ is P (= O) Ar ₂ .

The compound represented by the formula (1) may be represented by any one of the following formulas (2) to (7).

In the above Chemical Formulas 2 to 7,

Ar ₁ , Ar ₂ and Y ₁ to Y ₁₂ are each as defined in formula (1).

In the above Chemical Formulas 1 to 7,

Ar ₁ to Ar ₂ are the same or different and each independently represents 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 , 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 aryl A silyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, and a C ₆ to C ₆₀ arylamine group, and may be bonded to adjacent groups to form a condensed ring.

Preferably, Ar ₁ may be selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

Preferably, Ar ₂ may be selected from the group consisting of a C ₁ to C ₄₀ alkyl group and a C ₆ to C ₆₀ aryl group, more preferably Ar ₂ may be a phenyl group, a naphthyl group or a biphenyl group.

Y ₁ to Y ₁₂ are the same or different and are each independently N or C (R ₁ ), preferably Y ₁ to Y ₁₂ are both C (R ₁ ), or one of Y ₁ to Y ₁₂ May be N and the remainder may be C (R ₁ ). At this time, when R ₁ is plural, they are the same or different.

R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl , 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 aryl A silyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, and a C ₆ to C ₆₀ arylamine group, or may be bonded to an adjacent group to form a condensed ring .

The alkyl, aryl and heteroaryl groups of Ar ₁ , Ar ₂ and R ₁ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ aryloxy group, C _A group consisting of a C ₁ 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 arylboron group and a C ₆ to C ₆₀ arylamine group , And the substituent may be bonded to adjacent groups to form a condensed ring. However, when there are a plurality of substituents, they may be the same or different.

In the above Chemical Formulas 1 to 13, Ar ₁ and R ₁ are each independently a substituent represented by the following Chemical Formula 14 or a C ₆ -C ₆₀ aryl group (for example, a phenyl group, a biphenyl group, a terphenyl group, a fluorene group Etc.)

Wherein each of the aryl groups of Ar ₁ and R ₁ is independently selected from the group consisting of deuterium (D), 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, 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 , An arylsilyl group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, and a C ₆ to C ₆₀ arylamine group The substituent may be bonded to adjacent groups to form a condensed ring. When the substituent is plural, the substituents may be the same or different from each other.

In Formula 14,

L is a single bond or a group selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms,

Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₄ ), wherein when C (R ₁₄ ) is plural, they are the same or different,

R ₁₄ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of Or may combine with adjacent groups to form a condensed ring,

In this case, the alkyl group of said R _14, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an alkyl silyl group when the alkyl boron group, an aryl boron group, and an aryl silyl group each independently selected from deuterium, halogen, cyano, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₁ ~ C ₄₀ An alkylsulfonyl group, an alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, and a C ₆ to C ₄₀ arylsilyl group, When a plurality of substituents are present, they may be the same or different.

Examples of the substituent represented by the formula (14) include substituents represented by any one of the following formulas (S-1) to (S-15), but are not limited thereto.

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

및

,

And

In the above formulas (S-1) to (S-15)

L and R < ₁₄ > are the same as defined in the above formula (14)

When there are plural R < ₁₅ > s, they are the same or different from each other,

R ₁₅ represents a hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of Or may combine with adjacent groups to form a condensed ring,

n is an integer of 1 to 4,

In this case, the alkyl group of said R _15, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an alkyl silyl group when the alkyl boron group, an aryl boron group, and an aryl silyl group each independently selected from deuterium, halogen, cyano, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₁ ~ C ₄₀ An alkylsulfonyl group, an alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, and a C ₆ to C ₄₀ arylsilyl group, When a plurality of substituents are present, they may be the same or different.

The compound represented by the formula (1) according to an example of the present invention may be represented by any one of the following formulas (8) to (13), but is not limited thereto.

In the above Formulas 8 to 13,

Ar ₁ are as defined in formula I,

When a plurality of Ar _{1 s} are present, they are the same or different from each other.

Examples of the compound represented by the formula (1) according to an example of the present invention include the compounds A-1 to A-108, the compounds B-1 to B-108, and the like.

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 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 silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, Quot; unsubstituted alkylboron group "means a boron group substituted with alkyl having 1 to 40 carbon atoms," unsubstituted arylboron group "means a boron group substituted with aryl having 6 to 60 carbon atoms, Amine "means an amine substituted with aryl having 6 to 60 carbon atoms.

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.

2. Organic Field  Light emitting element

Meanwhile, the present invention provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1).

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compound represented by the formula (1) may be used singly or in combination of two or more.

According to an embodiment of the present invention, the at least one organic material layer includes a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. . Preferably, the organic material layer containing the compound of Formula 1 may be a light emitting layer or an electron transporting layer. Alternatively, a hole blocking layer may be interposed between the light emitting layer and the electron transporting layer.

For example, when the light emitting layer of the organic electroluminescent device includes a host material, the host material may include a compound represented by the above formula (1). When the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a green or red phosphorescent host, the bonding force between holes and electrons in the light emitting layer is increased, (Luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

According to another embodiment of the present invention, the one or more organic layers may include a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer. At least one organic layer, Layer may comprise the compound of Formula 1 above. Alternatively, a hole blocking layer may be interposed between the light emitting layer and the electron transporting layer.

According to another embodiment of the present invention, the one or more organic layers may include a hole injection layer, a hole transport layer, a light emitting layer, a life improving layer, an electron transport layer and an electron injection layer. The life improving layer may include the compound of the above formula (1). When the compound of Formula 1 is used as a material for improving the lifetime, it has a higher triplet energy than conventional BCP, so that the lifetime of the organic electroluminescent device can be improved.

The structure of the organic electroluminescent device according to an exemplary embodiment of the present invention is not particularly limited. For example, an anode, one or more organic material layers and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is formed on the electrode- It may be an inserted structure.

Specifically, the structure of the organic electroluminescent device may be a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are sequentially laminated on a substrate. Alternatively, a light emission-assisting layer may be interposed between the hole transporting layer and the light emitting layer. Further, a life improving layer may be interposed between the light emitting layer and the electron transporting layer. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer, the light emitting auxiliary layer, and the lifetime improving layer may include the compound represented by Formula 1, At least one of the light-emitting layer, the light-emitting layer, the light-emitting layer, the transport layer, the life improving layer, and the light-

The organic electroluminescent device according to an exemplary embodiment of the present invention includes at least one of the organic material layers (for example, at least one of a light emitting layer, an electron hydrogen layer, a light emitting auxiliary layer, and a life improving layer) , Can be produced by forming other organic layers and electrodes using materials and methods known in the art.

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.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metal oxides such as i) metals such as vanadium, chromium, copper, zinc and gold or their alloys, ii) metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide , iii), ZnO: Al or SnO _2: Sb combination of metal and oxides such as, iv), polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) Thiophene] (PEDT), conductive polymers such as polypyrrole or polyaniline, and v) carbon black, but are not limited thereto.

Examples of the negative electrode material include i) a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof, ii) LiF / Al or LiO ₂ / Al, and the like, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in detail with reference to 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] 14-phenyl-9,14- dihydrodibenzo [b, f] 포핀indolo [2,3-d] azepine  Synthesis of 14-oxide

≪ Step 1 > 3- (2- 아민ophenyl ) -1-phenyl-1H- phosphindole  Synthesis of 1-oxide

(2-aminophenyl) boronic acid (49.3 g, 360.5 mmol) and Pd (PPh3) ₄ (18.9 g, 16.3 mmol) were added to a solution of _3- bromo- , K ₂ CO ₃ (67.9 g, 491.6 mmol) were added to 1000 ml of toluene, 200 ml of EtOH and 200 ml of H ₂ O, and the mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 3- (2-aminophenyl) -1-phenyl-1H-phosphindole 1-oxide (72.8 g, yield 70%) was obtained by column chromatography.

^{1 H-NMR: δ 6.27 (} s, 2H), 6.58 (d, 1H), 6.73 (t, 1H), 6.76 (t, 1H), 7.00 (s, 1H), 7.13 (d, 1H), 7.33- 1H), 7.76-7.77 (m, 2H), 7.40 (m, 3H)

[LCMS]: 317

<Step 2> Synthesis of 3- (2- 아민ophenyl )-2- bromo -1-phenyl-1H- phosphindole  Synthesis of 1-oxide

(72.8 g, 248.3 mmol), NBS (N-bromosuccinimide) (44.2 g, 248.3 mmol) and DMF (700 mL) were mixed and reacted for 3 hours at room temperature Lt; / RTI &gt;

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 3- (2-aminophenyl) -2-bromo-1-phenyl-1H-phosphindole 1-oxide (62.9 g, yield 64%) was obtained by column chromatography.

^{1 H-NMR: δ 6.27 (} s, 2H), 6.58 (d, 1H), 6.73 (t, 1H), 6.76 (t, 1H), 7.13 (d, 1H), 7.33-7.40 (m, 3H), 7.44-7.45 (m, 3H), 7.72 (d, 1H), 7.76-7.77 (m, 2H)

[LCMS]: 396

&Lt; Step 3 > 3- (2- 아민ophenyl ) -2- (2- klorophenyl ) -1-phenyl-1H- phosphindole  Synthesis of 1-oxide

(2-chlorophenyl) boronic acid (27.3 g, 174.6 mmol) and Pd (PPh ₃ ) were added to a solution of 3- (2-aminophenyl) -2-bromo- ₄ (9.1 g, 7.9 mmol) and K ₂ CO ₃ (32.9 g, 238.0 mmol) were added to 600 ml of toluene, 150 ml of EtOH and 150 ml of H ₂ O and the mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 48.8 g (yield 72%) of 3- (2-aminophenyl) -2- (2-chlorophenyl) ).

^{1 H-NMR: δ 6.27 (} s, 2H), 6.63 (d, 1H), 6.70 (t, 1H), 6.81 (t, 1H), 7.24-7.33 (m, 4H), 7.44-7.50 (m, 7H ), 7.77 (d, 3H)

[LCMS]: 427

<Step 4> Synthesis of 14-phenyl-9,14- dihydrodibenzo [b, f] 포핀indolo [2,3-d] azepine  Synthesis of 14-oxide

Pd ₂ (dba) ₃ (5.2 g, 5.7 mmol), tri- (2-chlorophenyl) tert- butylphosphine (1.1 g, 5.7 mmol), sodium tert-butoxide (16.4 g, 171.0 mmol) and toluene (500 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (29.0 g, yield 65% ).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.81 (t, 2H), 7.05 (t, 2H), 7.25-7.30 (m, 3H), 7.45-7.50 (m, 5H), 7.77 (d, 3H ), 8.21 (d, 2H)

[LCMS]: 391

[ Preparation Example  2] 14- ( naphthalen -2- yl ) -9,14- dihydrodibenzo [b, f] 포핀indolo [2,3-d] azepine 14-oxide

The procedure of Preparation Example 1 was repeated except that 3-bromo-1- (naphthalen-2-yl) -1H-phosphindole 1-oxide was used as the starting reactant in Step 1 to obtain the desired compound 14- (naphthalen- 2-yl) -9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (26.0 g, yield 21%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.81 (t, 2H), 7.05 (t, 2H), 7.25-7.30 (m, 3H), 7.45-7.59 (m, 5H), 7.77 (d, 1H ), 7.94-8. 00 (m, 4H), 8.21 (d, 2H)

[LCMS]: 441

[Preparation Example 3] 14 - ([1,1'- biphenyl] -3- yl) -9,14-dihydrodibenzo [b, f] Synthesis of phosphindolo [2,3-d] azepine 14 -oxide

The procedure of Preparation Example 1 was repeated except that 1 - ([1,1'-biphenyl] -3-yl) -3-bromo-1H-phosphindole 1-oxide was used as a starting reactant in Step 1 The target compound 14 - ([1,1'-biphenyl] -3-yl) -9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (25.7 g, .

^{1 H-NMR: δ 4.0 (} s, 1H), 6.81 (t, 2H), 7.05 (t, 2H), 7.25-7.30 (m, 3H), 7.45-7.52 (m, 9H), 7.66 (s, 1H ), 7.73 (d, 1 H), 7.77 (d, 1 H), 8.21 (d,

[LCMS]: 467

[ Preparation Example  4] 9-phenyl-9,14- dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole  Synthesis of 9-oxide

<Step 1> phenylbis (2- vinylphenyl ) Synthesis of phosphine oxide

2-Bromotryrene (100 g, 546.2 mmol) was slowly added to the solution under the condition that water was removed under reduced pressure (THF) and MgCl 2 (13.3 g, 546.2 mmol) and the mixture was refluxed at 95 ° C for 6 hours. Phenylphosphonic dichloride (42.6 g, 218.8 mmol) was slowly added at 0 ° C and stirred at room temperature for 12 hours. 0.1M H ₂ SO ₄ was added thereto, and the mixture was extracted with methylene chloride, which was then mixed with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, phenylbis (2-vinylphenyl) phosphine oxide (49.1 g, yield 68%) was obtained by column chromatography.

^{1 H-NMR: δ 5.34 (} d, 2H), 5.44 (d, 2H), 6.90 (t, 2H), 7.33-7.45 (m, 9H), 7.72 (d, 2H), 7.77 (d, 2H)

[LCMS]: 330

&Lt; Step 2 > 5-phenyl-5H- dibenzo Synthesis of [b, f] phosphepine 5-oxide

Hoveyda-Grubbs second generation (4.6 g, 7.4 mmol) catalyst was added to a shrink tube connected with a condenser under an argon atmosphere. To the mixture was added phenylbis (2-vinylphenyl) phosphine oxide (49.1 g, 148.5 mmol) synthesized in Step 1 and Toluene 150 ml and heat at 100 ° C. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 5-phenyl-5H-dibenzo [b, f] phosphepine 5-oxide (38.2 g, yield 85%) was obtained by column chromatography.

^{1 H-NMR: δ 6.99 (} s, 2H), 7.30 (t, 2H), 7.45-7.50 (m, 7H), 7.77 (d, 4H)

[LCMS]: 302

&Lt; Step 3 > 6-phenyl-6,10b- dihydro -One aH - dibenzo [2,3: 6,7] phosphepino [4,5-b] oxirene 6- oxide  synthesis

(38.2 g, 126.3 mmol), meta- chloroperoxybenzoic acid (26.1 g, 151.5 mmol), silica (76.4 g), NaOCl (76.4 g), and acetonitrile (1500 ml) were mixed and stirred at 80 ° C for 2 hours.

After the reaction was completed, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and recrystallized from ethanol to obtain 30.1 g of 6-phenyl-6,10b-dihydro-1aH-dibenzo [2,3: 6,7] phosphepino [4,5- b] oxirene 6-oxide 75%).

^{1 H-NMR: δ 4.20 (} s, 2H), 7.36-7.38 (m, 6H), 7.45 (t, 3H), 7.70 (d, 2H), 7.77 (d, 2H)

[LCMS]: 318

<Step 4> Synthesis of 5-phenyl-5H- dibenzo [b, f] phosphepin-10 (11H) -one 5- oxide  synthesis

Dihydro-lH-dibenzo [2,3: 6,7] phosphepino [4,5-b] oxirene 6-oxide (30.1 g, 94.7 mmol) obtained in Step 3, lithium iodide (15.1 g, 113.4 mmol) and chloroform (300 ml) were mixed and stirred at 60 ° C for 1 hour.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed with MgSO ₄ , and the residue was recrystallized in ethanol to obtain 23.8 g of 5-phenyl-5H-dibenzo [b, f] phosphepin-10 , Yield: 79%).

^{1 H-NMR: δ 3.81 (} s, 2H), 7.23-7.33 (m, 3H), 7.45 (t, 3H), 7.56 (t, 1H), 7.64-7.65 (m, 2H), 7.77 (d, 2H ), 7.88 (d, 1 H), 7.94 (d, 1 H)

[LCMS]: 318

<Step 5> Synthesis of 9-phenyl-9,14- dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole  Synthesis of 9-oxide

(11H) -one 5-oxide (23.8 g, 74.7 mmol) obtained in <Step 4> and phenylhydrazine (8.9 g, 82.1 mmol) and acetic acid (900 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and purified by column chromatography to obtain 9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide (19.8 g, ).

¹ H-NMR:? 7.08 (t, 2H), 7.41-7.56 (m, 9H), 7.77-7.83

[LCMS]: 391

[ Preparation Example  5] 9- ( naphthalen -2- yl ) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9- oxide  synthesis

(Naphthalen-2-yl) -9,14-dihydrodibenzo [2,3: 6, 4-dihydrodibenzo [ 7] phosphepino [4,5-b] indole 9-oxide (21.2 g, yield 22%).

¹ H-NMR:? 7.08 (t, 2H), 7.41-7.59 (m, 9H), 7.79-7.84 (m, 3H), 7.83-8.00

[LCMS]: 441

[ Preparation Example  6] 9 - ([1,1'-biphenyl] -3- yl ) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9- oxide  synthesis

The procedure of Preparation Example 4 was repeated except that [1,1'-biphenyl] -3-ylphosphonic dichloride was used as a reactant in Step 1 to obtain the desired compound 9 - ([1,1'-biphenyl] -3 -yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (21.4 g, yield 21%).

¹ H-NMR:? 7.08 (t, 2H), 7.41-7.52 (m, 13H), 7.73-7.83

[LCMS]: 467

[ Synthetic example  1] Compound A-3 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 3-bromo-1,1'- g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) Were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 9 - ([1,1'-biphenyl] -3-yl) -14-phenyl-9,14- dihydrodibenzo [b, f] phosphindolo [ 2,3-d] azepine 14-oxide (2.9 g, yield 70%).

[LCMS]: 543

[ Synthetic example  2] Compound A-18 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 2- (4-bromophenyl) diphenyl-1,3,5-triazine (3.5 g , 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 9- (4,6-diphenyl-1,3,5-triazin-2-yl) Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3.5 g, yield 66%).

[LCMS]: 698

[ Synthetic example  3] Compound A-24 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 2- (3'-chloro- [1,1 3-yl) -4,6-diphenyl-1,3,5-triazine (3.8 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 9- (3 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1'-biphenyl ] -3-yl) -14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (4.0 g, yield 68%).

[LCMS]: 774

[ Synthetic example  4] Compound A-25 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 2- (1,1'- 4-yl) -4-bromo-6-phenyl-1,3,5-triazine (3.8 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine , 0.4 mmol), sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After the solvent of the filtered organic layer was removed, the desired compound, 9- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin-2 -yl) -14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (3.5 g, yield 65%).

[LCMS]: 698

[ Synthetic example  5] Compound A-26 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 2- (1,1'- 4-yl) -4- (4- bromophenyl) -6-phenyl-1,3,5-triazine (4.2 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert - butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the desired compound, 9- (4- (4 - ([1,1'-biphenyl] -4-yl) -6- triazin-2-yl) phenyl) -14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (3.5 g, yield 65%).

[LCMS]: 774

[ Synthetic example  6] Compound A-28 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) prepared in Preparation Example 1 and 4- (1,1'-biphenyl- Tert- butylphosphine (0.08 g, 0.4 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) And sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 9- (4- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin- -14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3.9 g, yield 67%).

[LCMS]: 773

[ Synthetic example  7] Compound A-31 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) and 2- (4-bromophenyl) dibenzo [b, ] thiophene (3.1 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert- (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 9- (4- (dibenzo [b, d] thiophen-2-yl) phenyl) -14-phenyl-9,14-dihydrodibenzo [ f] phosphindolo [2,3-d] azepine 14-oxide (3.6 g, yield 72%).

[LCMS]: 649

[ Synthetic example  8] Compound A-32 Synthesis

A mixture of 14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3 g, 8.8 mmol) and 2-bromodibenzo [b, , 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) to And the mixture was stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 9- (dibenzo [b, d] furan-2-yl) -14-phenyl-9,14-dihydrodibenzo [b, , 3-d] azepine 14-oxide (3.0 g, yield 70%).

[LCMS]: 557

[ Synthetic example  9] Compound A-33 Synthesis

(3.5 g, 8.8 mmol) and 14-phenyl-9,14-dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14- 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene And stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the desired compound 14-phenyl-9- (4- (triphenylen-2-yl) phenyl) -9,14-dihydrodibenzo [b, f] phosphindolo [ 3-d] azepine 14-oxide (3.3 g, yield 62%).

[LCMS]: 693

[ Synthetic example  10] Compound A-60 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3.38 g, 7.6 mmol) prepared in Preparation Example 2 and 2- (3'-chloro- [1,1 3-yl) -4,6-diphenyl-1,3,5-triazine (3.8 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 9- (3 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1'-biphenyl ] -3-yl) -14- (naphthalen-2-yl) -9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (3.8 g, yield 60%).

[LCMS]: 824

[ Synthetic example  11] Compound A-61 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3.38 g, 7.6 mmol) prepared in Preparation Example 2 and 2- ([1,1'-biphenyl] 4-yl) -4-bromo-6-phenyl-1,3,5-triazine (3.5 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine , 0.4 mmol), sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After the solvent of the filtered organic layer was removed, the desired compound, 9- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin-2 -yl) -14- (naphthalen-2-yl) -9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (3.5 g, yield 62%).

[LCMS]: 748

[ Synthetic example  12] Compound A-100 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide of Preparation Example 3 (3.6 g, 7.7 mmol) 4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (4.3 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) , tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 14 - ([1,1'-biphenyl] -3-yl) -9- (4- (6- ] -4-yl) -2-phenylpyrimidin-4-yl) phenyl) -9,14-dihydrodibenzo [b, f] phosphindolo [2,3- d] azepine 14-oxide (4.1 g, .

[LCMS]: 849

[ Synthetic example  13] Compound A-105 Synthesis

Dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide of Preparation Example 3 (3.6 g, 7.7 mmol) and 2- (4-bromophenyl) triphenylene ( 3.5 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the desired compound 14 - ([1,1'-biphenyl] -3-yl) -9- (4- (triphenylen- , 14-dihydrodibenzo [b, f] phosphindolo [2,3-d] azepine 14-oxide (3.7 g, yield 63%).

[LCMS]: 769

[ Synthetic example  14] Compound B-3 Synthesis

A mixture of 9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3 g, 8.8 mmol) prepared in Preparation Example 4 and 3-bromo- -biphenyl (2.1 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14 - ([1,1'-biphenyl] -3-yl) -9-phenyl-9,14- dihydrodibenzo [ 7] phosphepino [4,5-b] indole 9-oxide (2.9 g, yield 70%).

[LCMS]: 543

[ Synthetic example  15] Compound B-18 Synthesis

(3 g, 8.8 mmol) and 2- (4-bromophenyl) - indole-9-oxide of Preparation Example 4 were reacted with 9-phenyl-9,14-dihydrodibenzo [ 4,6-diphenyl-1,3,5-triazine (3.5 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) -butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl- 14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3.5 g, yield 66%).

[LCMS]: 698

[ Synthetic example  16] Compound B-24 Synthesis

A solution of 9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3 g, 8.8 mmol) (3.8 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), tri (3-methoxyphenyl) It was mixed with tert -butylphosphine (0.08 g, 0.4 mmol ) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) and stirred for 6 hours at room temperature. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (3 '- (4,6-diphenyl-1,3,5-triazin-2- yl) - [1,1'-biphenyl ] -3-yl) -9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide (4.0 g, yield 68%).

[LCMS]: 774

[ Synthetic example  17] Compound B-25 Synthesis

(3 g, 8.8 mmol) and 2 - ([1,1 '] biphenyl-3,3,6,7] phosphepino [4,5- -biphenyl] -4-yl) -4- bromo-6-phenyl-1,3,5-triazine (3.8 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert - butylphosphine (0.08 g, 0.4 mmol), sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin- -yl) -9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide (3.5 g, yield 65%).

[LCMS]: 698

[ Synthetic example  18] Compound B-26 Synthesis

(3 g, 8.8 mmol) and 2 - ([1,1 '] biphenyl-3,3,6,7] phosphepino [4,5- (4.2 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) were added to a solution of 4- tert- Butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (4- (4 - ([1,1'-biphenyl] -4-yl) -6- triazin-2-yl) phenyl) -9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide (3.5 g, yield 65%).

[LCMS]: 774

[ Synthetic example  19] Compound B-28 Synthesis

(3 g, 8.8 mmol) and 4 - ([1,1 '] bipyridyl) -9,11-dihydrodibenzo [2,3: (4-bromophenyl) -2-phenylpyrimidine (4.2 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) and tri- tert- butylphosphine , 0.4 mmol), sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (4- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin- -9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3.9 g, yield 67%).

[LCMS]: 773

[ Synthetic example  20] Compound B-31 Synthesis

Preparation of 9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3 g, 8.8 mmol) and 2- (4-bromophenyl) dibenzo [b, d] thiophene (3.1 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removal of the solvent of the filtered organic layer, the target compound, 14- (4- (dibenzo [b, d] thiophen-2-yl) phenyl-9-phenyl-9,14-dihydrodibenzo [ 3: 6,7] phosphepino [4,5-b] indole 9-oxide (3.6 g, yield 72%).

[LCMS]: 649

[ Synthetic example  21] Compound B-32 Synthesis

(3 g, 8.8 mmol) and 2-bromodibenzo [b, d] indole 9-oxide of Preparation Example 4 in 9-phenyl-9,14-dihydrodibenzo [ furan (2.3 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene ( 50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (dibenzo [b, d] furan-2-yl) -9-phenyl-9,14-dihydrodibenzo [ ] phosphepino [4,5-b] indole 9-oxide (3.0 g, yield 70%).

[LCMS]: 557

[ Synthetic example  22] Compound B-33 Synthesis

Preparation of 9-phenyl-9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3 g, 8.8 mmol) and 2- (4-bromophenyl) triphenylene (3.5 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the desired compound 9-phenyl-14- (4- (triphenylen-2-yl) phenyl) -9,14- dihydrodibenzo [2,3: phosphepino [4,5-b] indole 9-oxide (3.3 g, yield 62%).

[LCMS]: 693

[ Synthetic example  23] Compound B-60 Synthesis

A solution of 9- (naphthalen-2-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9- oxide (3.38 g, 7.6 mmol) (3.8 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 9.2 mmol) were added to a solution of 3'-chloro- [1,1'-biphenyl] , 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (3 '- (4,6-diphenyl-1,3,5-triazin-2- yl) - [1,1'-biphenyl ] -3-yl) -9- (naphthalen-2-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9- ).

[LCMS]: 824

[ Synthetic example  24] Compound B-61 Synthesis

A solution of 9- (naphthalen-2-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9- oxide (3.38 g, 7.6 mmol) (3.5 g, 9.2 mmol) and Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) in DMF (4 mL) ), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the target compound, 14- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin- -yl) -9- (naphthalen-2-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide .

[LCMS]: 748

[ Synthetic example  25] Compound B-100 Synthesis

Preparation of 9 - ([1,1'-biphenyl] -3-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide 4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (4.3 g, 9.2 mmol) and Pd ₂ (dba) ₃ , 0.4 mmol), tri- tert- butylphosphine (0.08 g, 0.4 mmol) and sodium tert-butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the objective compound, 9 - ([1,1'-biphenyl] -3-yl) -14- (4- (6- ] -4-yl) -2-phenylpyrimidin-4-yl) phenyl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide (4.1 g, %).

[LCMS]: 849

[ Synthetic example  26] Compound B-105 Synthesis

Preparation of 9 - ([1,1'-biphenyl] -3-yl) -9,14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5- b] indole 9-oxide , 7.7 mmol) and 2- (4-bromophenyl) triphenylene ( 3.5 g, 9.2 mmol) and _{Pd 2 (dba) 3 (0.4} g, 0.4 mmol), tri- tert -butylphosphine (0.08 g, 0.4 mmol) and Sodium tert -butoxide (1.1 g, 11.5 mmol) and Toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, the desired compound 9 - ([1,1'-biphenyl] -3-yl) -14- (4- (triphenylen- , 14-dihydrodibenzo [2,3: 6,7] phosphepino [4,5-b] indole 9-oxide (3.7 g, yield 63%).

[LCMS]: 769

[ Example  1 ~ 26] Blue organic Field  Manufacturing of light emitting device

A-3, A-18, A-24, A-25, A-26, A-28, A-31, A-32, A- A-100, A-105, B-3, B-18, B-24, B-25, B-26, B-28, B- 61, B-100 and B-105 were subjected to high purity sublimation purification by a commonly known method, and blue organic electroluminescent devices were prepared as follows.

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, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) The substrate was transferred to a vacuum evaporator.

 (DS-205, Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound A-3 and A-18 , A-24, A-25, A-26, A-28, A-31, A-32, A-33, A-60, A- (B), (B), (B), (B), (B) 30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to manufacture an organic electroluminescent device.

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

A blue organic electroluminescent device was produced in the same manner as in Example 1 except that Alq3 was used instead of Compound A-3 as the electron transport layer material.

[ Comparative Example  2] Blue organic Field  Manufacturing of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that A-3 was not used as the electron transport layer material.

 The structures of NPB, AND and Alq3 used in Examples 1 to 26 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices prepared in Examples 1 to 26 and Comparative Examples 1 and 2, Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 A-3 4.5 458 7.0 Example 2 A-18 4.6 459 6.9 Example 3 A-24 4.1 458 7.1 Example 4 A-25 3.8 452 6.8 Example 5 A-26 4.0 448 6.7 Example 6 A-28 4.4 457 6.8 Example 7 A-31 3.9 456 7.3 Example 8 A-32 3.8 452 6.8 Example 9 A-33 3.9 457 7.3 Example 10 A-60 4.1 456 7.3 Example 11 A-61 3.6 468 6.8 Example 12 A-100 3.5 465 6.9 Example 13 A-105 4.2 459 6.8 Example 14 B-3 4.1 461 6.4 Example 15 B-18 4.1 455 6.5 Example 16 B-24 4.2 459 6.8 Example 17 B-25 3.9 464 6.4 Example 18 B-26 3.6 467 7.1 Example 19 B-28 4.1 455 7.1 Example 20 B-31 4.2 459 6.7 Example 21 B-32 4.1 458 7.1 Example 22 B-33 4.4 457 6.8 Example 23 B-60 3.9 457 6.5 Example 24 B-61 4.1 456 6.9 Example 25 B-100 3.9 464 6.9 Example 26 B-105 3.9 457 7.1 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent devices (Examples 1 to 26) using the compound according to an example of the present invention as the electron transport layer were the same as those of the blue organic electroluminescent device using the conventional Alq3 as the electron transport layer ) And the blue organic electroluminescent device having no electron transporting layer (Comparative Example 2), it showed excellent performance in terms of driving voltage, luminescent peak and current efficiency.

Claims (10)

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

In Formula 1,
X ₁ and X ₂ are different from each other and each independently selected from the group consisting of N (Ar ₁ ), O, S and P (= O) Ar _{2 wherein} one of X ₁ and X ₂ is P ) Ar ₂ ,
Y ₁ to Y ₁₂ are the same or different and each independently N or C (R ₁ ), wherein when R ₁ is plural, they are the same or different,
Ar ₁ to Ar 2 are the same or different and each independently represents 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 , 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 A group selected from the group consisting of C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₆₀ aryl boron groups and C ₆ to C ₆₀ aryl amine groups, and may form a condensed ring by bonding with adjacent groups,
R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl , 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 aryl A silyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, and a C ₆ to C ₆₀ arylamine group, or may be bonded to an adjacent group to form a condensed ring ,
The alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group and the aryl group of Ar ₁ , Ar ₂ and R ₁ , arylamine groups are each independently a heavy hydrogen (D), a halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 of the An 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 Arylsulfonyl group, arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylboron group, and C ₆ to C ₆₀ arylamine group, which may be substituted or unsubstituted with at least one substituent selected from the group consisting of The substituent may be bonded to adjacent groups to form a condensed ring. When the substituent is plural, they may be the same or different from each other. Can. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (2) to (7)
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 2 to 7,
Ar ₁ , Ar ₂ and Y ₁ to Y ₁₂ are as defined in claim ₁ , respectively. The method according to claim 1,
Ar ₁ , Ar ₂ and R ₁ are the same or different and are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms ,
The alkyl, aryl and heteroaryl groups of Ar ₁ , Ar ₂ and R ₁ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ aryloxy group, C _A group consisting of a C ₁ 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 arylboron group and a C ₆ to C ₆₀ arylamine group , Wherein the substituent may be bonded to adjacent groups to form a condensed ring, provided that 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 represented by any one of the following formulas (8) to (13):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above formulas (8) to (13)
Ar ₁ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl, aryl and heteroaryl groups of Ar ₁ are each independently selected from the group consisting of deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, 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 ₁ to C ₄₀ alkyl silyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ aryl boron, and C ₆ ~ one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ Wherein the substituent may be bonded to adjacent groups to form a condensed ring, provided that when there are plural substituents, they may be the same or different. The method according to claim 1,
Each of Ar ₁ and R ₁ is independently a substituent represented by the following formula (14), or a C ₆ to C ₆₀ aryl group,
The aryl groups of Ar ₁ and R ₁ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, An alkyl 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 ₁ to C ₄₀ alkylsilyl group, a first substituent at least one selected from the group consisting of C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl boronic of C ₆₀ and C ₆ ~ with an aryl amine of the C ₆₀ Wherein the substituent may be bonded to an adjacent group to form a condensed ring, provided that when the substituent is plural, they may be the same or different from each other,
[Chemical Formula 14]

In Formula 14,
L is a single bond or a group selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms,
Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₄ ), wherein when C (R ₁₄ ) is plural, they are the same or different,
R ₁₄ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of Or may combine with adjacent groups to form a condensed ring,
In this case, the alkyl group of said R _14, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an alkyl silyl group when the alkyl boron group, an aryl boron group, and an aryl silyl group each independently selected from deuterium, halogen, cyano, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₁ ~ C ₄₀ An alkylsulfonyl group, an alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, and a C ₆ to C ₄₀ arylsilyl group, When a plurality of substituents are present, they may be the same or different. The method according to claim 1,
Wherein Ar ₁ and R ₁ are each independently a substituent represented by any of the following formulas (S-1) to (S-15):

,

,

,

,

,

,

,

,

,

,

,

,

,

And

In the above formulas (S-1) to (S-15)
L is a single bond or a group selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms,
When there are plural R &lt; _{14 &} gt ;, they are the same or different,
R ₁₄ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, A C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, and a C ₆ to C ₄₀ arylsilyl group, A condensed ring can be formed,
When there are plural R &lt; ₁₅ &gt; s, they are the same or different,
R ₁₅ represents a hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of Or may combine with adjacent groups to form a condensed ring,
n is an integer of 1 to 4,
The alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, alkylsilyl group, alkylboron group, arylboron group and arylsilyl group of R ₁₄ and R ₁₅ are each independently selected from the group consisting of deuterium, , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to 40 of the C ₆ ~ aryloxy group of C _40, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₁ ~ silyl C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ or unsubstituted be ring And when the substituent is plural, they may be the same or different from each other. 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 the compound according to any one of claims 1 to 6. 8. The method of claim 7,
Wherein the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer,
Wherein at least one organic compound layer containing the compound is a light emitting layer or an electron transporting layer. 8. The method of claim 7,
Wherein the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer,
Wherein at least one organic compound layer containing the compound is a light-emission-assisting layer. 8. The method of claim 7,
Wherein the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, a water surface improving layer, an electron transporting layer, and an electron injecting layer,
Wherein at least one organic layer including the compound is a life improving layer.