KR101577121B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same, and the compound according to the present invention is used for an organic compound layer, preferably a light emitting layer, of an organic electroluminescent device, And the like can be improved.

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 that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity 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 make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing 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 organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

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

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, since the conventional materials have low glass transition temperature and their thermal stability deteriorates, they are not satisfactory in terms of lifetime in OLED devices, and improvements in light emission characteristics are also needed. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound which has a high glass transition temperature and is excellent in thermal stability and can improve the bonding property between holes and electrons and improve the luminescent properties.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and having improved driving voltage, luminous efficiency, and the like.

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

In Formula 1,

X ₁ to X ₃ are the same or different and each independently CR ₃ or N, and at least one of X ₁ to X ₃ is N, and when CR ₃ is plural, a plurality of R _{3 s} are the same Or different;

R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atoms, 3 to 40 heterocycloalkyl group of the , 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 alkyloxy group, a C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted or unsubstituted C ₁ ~ C _A substituted or unsubstituted 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, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, or they may form a condensed ring with adjacent groups;

Wherein at least one of R ₁ to R ₃ has a structure of the following formula 2 or 3;

In the general formula (2) or (3)

Y ₁ to Y ₈ are the same as or different from each other, and each independently CR ₄ or N, wherein when CR ₄ is plural, plural R _{4 s} are the same as or different from each other;

R ₄ and R ₅ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atoms, 3 to 40 heterocycloalkyl group of the , 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 alkyloxy group, a C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ of an alkyl boron group, a substituted or aryl phosphine of the unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the ring pingi, Is selected from unsubstituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine, or may form a condensed ring group and they are adjacent,

L ₁ is selected from a single bond, an arylene group having ₆ to ₆₀ carbon atoms, or a heteroarylene group having 5 to 60 nuclear atoms;

n is an integer from 0 to 4;

In R ₁ to R ₅ , 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 of 60, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ arylamine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the group each independently , deuterium, 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 aryl group, the number of nuclear atoms of 5 to a heteroaryl group of 60, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C _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 having ₆ to ₆₀ carbon atoms. Here, when a plurality of substituents are introduced to R ₁ to R ₅ , these substituents may be the same as or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more organic compounds A light emitting device is provided.

At least one of the one or more organic layers including the compound of Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer. In this case, the compound represented by Formula 1 may be a blue, green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time, A full-color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel organic electroluminescent compound according to the present invention has a structure represented by the above formula (1) in which various substituents, particularly N-containing heterocyclic rings, aromatic rings, etc., are connected to a triazolopyridine core.

In the above compound, the triazolopyridine core is a core having a high triple energy and stable structure and electron withdrawing characteristics. Such cores can be used for a blue phosphorescent host material having excellent efficiency by introducing a carbazole-type substituent having high triplet energy and excellent luminescence characteristics.

Most of the triazolo pyridine derivatives developed in the present invention have a bipolar characteristic as a whole due to a core having an electron withdrawing property and a carbazole substituent having a large electron donating property. The bipolar compound represented by the formula (1) of the present invention can be used not only as a host in a phosphorescent light emitting layer, but also as a hole transport layer, a hole injection layer, and an electron transport layer since it can increase the bonding force between holes and electrons . Accordingly, the compound of Formula 1 can improve the phosphorescence characteristics of the organic EL device, and improve the carrier transporting ability or the light emission efficiency.

In addition, since the solubility of the core itself is improved, the compound of Formula 1 can be used not only as a vapor deposition material but also as a soluble material. Therefore, not only an organic material layer of an organic electroluminescent device can be formed by a vacuum deposition method, but also a device can be manufactured by a solution process.

As a result, when the compound of Chemical Formula 1 according to the present invention is used as a hole injecting / transporting layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material and an electron injecting / transporting layer material, For example, CBP), the efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

In the compound represented by formula (1) of the present invention, X ₁ to X ₃ are the same as or different from each other, and each independently CR ₃ or N, and at least one of X ₁ to X ₃ is N. When a plurality of CR &lt; ₃ &gt; s are present, the plurality of R &lt; ₃ &gt; In this case, in consideration of the EWG (electron-attracting group) function, it is preferable that X ₁ to X ₃ are all N.

R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero A substituted or unsubstituted C ₁ to C ₆₀ alkyl group, 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 alkyloxy group, An unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ a ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the O Phosphine group, a substituted or unsubstituted and selected from the group consisting of an aryl phosphine oxide of the unsubstituted C ₆ ~ C ₆₀ group, and a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine, or may form a group and the condensed ring to which they are adjacent have.

In the present invention, at least one of the above-mentioned R ₁ to R ₃ has a structure represented by the following general formula (2) or (3) Herein, R ₁ to R ₃ which do not have the structure of the following formula 2 or 3 are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms , More preferably R ₂ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms. For example, R ₁ is a carbazole or a pyridoindole, and R ₂ or R ₃ is preferably a substituted or unsubstituted aryl group or a heteroaryl group.

(2)

(3)

In Formula 2 or Formula 3,

Y ₁ to Y ₈ are the same as or different from each other, and each independently CR ₄ or N, and when CR ₄ is plural, plural R _{4 s} are the same as or different from each other.

When the structure of Formula 2 or Formula 3 is bonded to Formula 1, at least one of R ₄ and R ₅ is bonded to Formula 1 through L ₁ . In this case, in the formula (2) or (3), * denotes a site connected to the formula (1).

In the present invention, R ₄ and / or R _{5 which} are non-bonded to the formula (1) are the same or different and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a cycloalkyl group of the substituted or unsubstituted C ₃ ~ C ₄₀ of, 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 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 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 ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, an aryl boronic a substituted or unsubstituted C ₆ ~ C ₆₀ group, Ring or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or they may form a condensed ring with adjacent groups.

The L is a divalent group linker known in the art and is a single bond, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted 5 to 60 &Lt; / RTI &gt; heteroarylene groups of the formula &lt; RTI ID = 0.0 &gt;

Here, the C ₆ ~ C ₆₀ arylene group, for example, the nuclear atoms of 5 to 60 hetero arylene group, the phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, an indenyl group, a pyran tray carbonyl group , A carbazolyl group, a thiophenylene group, an indolylene group, a prolinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, And the like. In the present invention, it is preferable that L is selected from a single bond, a phenylene group, or a biphenylene group.

In the L, C ₆ ~ C ₆₀ arylene group, the number of nuclear atoms of 5 to 60 hetero arylene group each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , A C ₂ to C ₄₀ alkynyl 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 alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ with an aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituents of two or more selected from the group consisting of And when the substituent is plural, they may be the same or different.

n is an integer of 0 to 4;

In the above-mentioned R ₁ to R ₅ , 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, of to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, 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 ~ C ₆₀ aryl amine groups are each independently by, heavy hydrogen, halogen, cyano, an alkyl group of _{C 1 ~ C 40, C 3} ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 of to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ of the aryloxy group, C-alkyl silyl group of _{3 ~ C 40, C 6 ~} C 60 aryl silyl group, C ₂ ~ of C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine of pingi, C ₆ ~ C ₆₀ An aryl phosphine oxide group, and an arylamine group having ₆ to ₆₀ carbon atoms.

Here, when a plurality of substituents are introduced to R ₁ to R ₅ , these substituents may be the same as or different from each other.

The compound represented by the formula (1) of the present invention may be further compounded by any one of the compounds represented by the following formulas (4) to (6).

In the above Chemical Formulas 4 to 6,

X ₁ to X ₃ , Y ₁ to Y ₈ , R ₁ to R ₅ and L ₁ are the same as defined in formulas (1) to (3).

According to a preferred embodiment of the present invention, when X ₁ to X ₃ are both N and L ₁ is a phenyl linker group, R ₁ is a carbazole or pyridoindole group, and R ₂ is Structures in which aromatic compounds are formed by CC bonds, for example, a substituted or unsubstituted aryl group or a heteroaryl group.

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

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

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

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

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. 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; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . &Lt; / RTI &gt; Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

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

The compounds of formula (1) of the present invention can be synthesized in various manners with reference to Synthesis Examples, and preferred examples thereof can be prepared by the following Reaction Schemes I and II.

[Reaction Scheme I]

[Reaction Scheme II]

The above-mentioned steps are reactions known in the art. Step a is a reaction for forming a substituent through Suzuki coupling reaction. Step b is an amine (NH ₂ ) group. (Step c) involves Suzuki coupling when a linker is introduced, and Buchwald (I, Br, Cl) when reacting with a carbazole or pyridoindole. coupling reaction proceeds. As in Scheme I, Scheme II is also different in sequence and the types of reactions used are the same.

Hereinafter, the detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

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

Specifically, the organic electroluminescent device according to the present invention includes an anode, 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 includes Include compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ Preferably, the organic compound layer containing the compound of Formula 1 may be a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved. The compound represented by Formula 1 may be included in the organic light emitting device as a phosphorescent host, a fluorescent host, or a dopant material of green, blue, and / or red.

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 layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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.

Non-limiting examples of usable cathode materials 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 or polyaniline; And carbon black, but are not limited thereto.

Non-limiting examples of usable cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

Hereinafter, the present invention will be described in detail with reference to 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 2,8-Dibromo- [1,2,4] triazolo [1,5-a] pyridine

<Step 1> Synthesis of 1- (3-Bromo-pyridine-2-yl) -3-carboethoxy-thiourea

1.0 g of DCB was added to 100 g (0.58 mol) of 2-amino-3-bromopyridine. Cooled to 0 ° C and 68.2 mL (0.58 mol) of ethoxycarbonyl isothiocyanate was slowly added dropwise over 15 minutes. The reaction solution was warmed to room temperature and stirred for 20 hours. The solvent was appropriately removed by distillation under reduced pressure and the mixture was filtered. After drying with warm air, 158 g of the objective compound (yield: 90%) was obtained.

<Step 2> Synthesis of 5-Bromo- [1,2,4] triazolopyridin-2-ylamine

A mixed solvent of EtOH / MeOH (1: 1, 1.5 L) was added to 180.5 g (2.60 mol) of hydroxylamine hydrochloride. 271 mL (1.56 mol) of N, N-diisopropylethylamine was added to the reaction solution and stirred for 1 hour. 158 g (0.52 mol) of 1- (3-Bromo-pyridine-2-yl) -3-carboethoxy-thiourea was added and the temperature was slowly raised and refluxed for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered. The filtrate was distilled under reduced pressure and the resulting solid was filtered. The resulting solid product was combined, washed with purified water, EtOH / MeOH mixed solvent and n-hexane, and dried under a warm air stream to obtain 91 g (yield 82%) of the desired compound.

^{1 H-NMR (300Mz, CDCl} 3- d6) 8.54 (d, 1H), 7.69 (d, 1H), 6.77 (t, 1H), 6.22 (s, 2H)

HRMS: 213

Preparation Example 2 Synthesis of 8- (9-phenyl-9H-carbazol-3-yl) - [1,2,4] triazolo [1,5-a] pyridin-

10 g (46.9 mmol) of 9-phenyl-3- (4,4,5,5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H-carbazole (19.1 g, 51.6 mmol) were added 200 mL of toluene, 50 mL of EtOH and 50 mL of H ₂ O. _{Pd (PPh 3) 4 2.7 g} (2.3 mmol), Na 2 CO 3 14.9 g (141 mmol) and then the mixture was heated to reflux at 120 ℃ 8 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (13.0 g, yield 74%).

_{^{1 H-NMR (in CDCl 3}} ): δ 7.79 (d, 1H), 7.76 (d, 1H), 7.40 (s, 1H), 7.36 (m, 2H)

Preparation Example 3 Synthesis of 3- (2-bromo- [1,2,4] triazolo [1,5-a] pyridin-8-yl) -9-phenyl-9H-

To 13 g (34.6 mmol) of CuBr _{2 was added} 3.9 g (17.3 mmol) of 8- (9-phenyl-9H-carbazol-3- yl) - [1,2,4] triazolo [1,5- ) And 130 mL of HBr. The mixture was cooled to 0 ° C and 2.9 g (41.6 mmol) of NaNO ₂ was dissolved in 30 mL of purified water and slowly added dropwise. The reaction solution was stirred at room temperature for 12 hours. 100 mL of an aqueous solution of sodium carbonate was added to the reaction mixture, and the mixture was stirred for 1 hour, and the resulting solid was filtered. The resulting solid was recrystallized from 150 mL of EA to obtain 13.4 g (yield 88%) of the desired compound.

[HRMS]: 439

Preparation Example 4 Synthesis of 8- (9-phenyl-9H-carbazol-2-yl) - [1,2,4] triazolo [1,5-a] pyridin-

A mixture of 8-bromo- [1,2,4] triazolo [1,5-a] pyridin-2-amine and 9-phenyl- 2- (4,4,5,5-tetramethyl- dioxaborolan-2-yl) -9H-carbazole was used in place of the compound obtained in Preparation Example 2 to obtain 15.0 g (yield: 85%) of the target compound.

[HRMS]: 375

Preparation Example 5 Synthesis of 2- (2-bromo- [1,2,4] triazolo [1,5-a] pyridin-8-yl) -9-phenyl-9H-

Preparation Example 3 was repeated except that 8- (9-phenyl-9H-carbazol-2-yl) - [1,2,4] triazolo [1,5- a] pyridin- The same procedure was followed to obtain the desired compound (8.5 g, yield 90%).

[HRMS]: 439

Preparation Example 6 Synthesis of 9- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole

20 g (72 mmol) of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (20.1 g, 79.2 mmol). 2.9 g (3.6 mmol) of Pd (dppf) Cl ₂ and 21.2 g (216 mmol) of KOAc were added to the reaction solution. The mixture was heated to reflux at 130 占 폚 for 12 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (20.0 g, yield 75%).

_{^{1 H-NMR (in CDCl 3}} ): δ 8.55 (d, 1H), 8.12 (d, 1H), 7.94 (m, 2H), 7.63 (m, 2H), 7.50 (m, 4H), 7.44 (s, 1H), 7.25 (m, 1H), 1.28 (s, 12H)

[HRMS]: 369

Preparation Example 7 Synthesis of 8- (9,9-dimethyl-9H-fluoren-3-yl) - [1,2,4] triazolo [1,5-a] pyridin-

Except that the reaction was carried out in the same manner as in Preparation Example 1 except that 2- (9,9-dimethyl-9H-fluoren-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used as a reactant. The procedure of Example 2 was repeated to obtain 9.4 g of the desired compound (yield 77%).

[HRMS]: 326

Preparation Example 8 Synthesis of 8- (9,9-dimethyl-9H-fluoren-3-yl) - [1,2,4] triazolo [1,5-a] pyridin-

The procedure of Preparation Example 3 was repeated except that Preparation Example 7 was used as a reactant, to obtain 8.8 g (yield 82%) of the desired compound.

[HRMS]: 390

Preparation Example 9 Synthesis of 8- (4- (diphenylamino) phenyl) - [1,2,4] triazolo [1,5-a] pyridin-2-amine

Preparation Example 2 was repeated except that Preparation Example 1 and N, N-diphenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- The same procedure was followed to obtain 21.8 g (yield 82%) of the desired compound.

_{^{1 H-NMR (in CDCl 3}} ): δ 8.22 (d, 1H), 7.83 (d, 2H), 7.47 (d, 1H), 7.28 (m, 5H), 7.13 (m, 5H), 7.04 (t, 2H), 6.87 (t, 1 H), 4.49 (s, 2 H)

[HRMS]: 377

Preparation Example 10 Synthesis of 4- (2-bromo- [1,2,4] triazolo [1,5-a] pyridin-8-yl) -N, N-diphenylaniline

The procedure of Preparation Example 3 was repeated, except that Preparation Example 9 was used as a reactant, to obtain 20.4 g (yield 83%) of the desired compound.

_{^{1 H-NMR (in CDCl 3}} ): δ 8.41 (d, 1H), 7.86 (d, 2H), 7.61 (d, 1H), 7.26 (m, 5H), 7.13 (m, 5H), 7.05 (t, 3H)

[HRMS]: 441

[Preparation Example 11] Synthesis of 9- (4-bromophenyl) -9H-pyrido [2,3-b] indole

300 mL of dioxane was added to 10.0 g (59.5 mmol) of 9H-pyrido [2,3-b] indole and 33.6 g (119 mmol) of 1-bromo-4-iodobenzene. 2.7 g (3.0 mmol) of Pd ₂ (dba) ₃ , 1.9 g (2.3 mmol) of BINAP and 38.7 g (119 mmol) of Cs ₂ CO ₃ were added and the mixture was refluxed at 120 ° C for 12 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (12.3 g, yield 64%).

[HRMS]: 323

Preparation Example 12 Synthesis of 9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-pyrido [2,3-b]

Except that the reaction was carried out in the same manner as in Preparation Example 11 except that 2- (9,9-dimethyl-9H-fluoren-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used as a reactant. The procedure of Example 6 was followed to obtain 9.9 g (yield 72%) of the desired compound.

[HRMS]: 326

Preparation Example 13 Synthesis of 8- (4- (naphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridin-2-amine

The procedure of Preparation Example 2 was repeated except that Preparation Example 1 and 4- (naphthalen-1-yl) phenylboronic acid were used as a reactant, to obtain 12.8 g (yield 81%) of the desired compound.

[HRMS]: 336

Preparation Example 14 Synthesis of 8- (4- (naphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridin-2-amine

12.6 g (yield: 88%) of the desired compound was obtained by carrying out the same procedure as Preparation Example 3, except that Preparation Example 13 was used as a reactant.

_{^{1 H-NMR (in CDCl 3}} ): δ 8.95 (d, 1H), 8.55 (t, 2H), 8.17 (t, 2H), 8.04 (d, 1H), 7.85 (m, 2H), 7.75 (m, 2H), 7.47 (t, 2H), 7.35 (d, 2H)

[HRMS]: 400

Preparation Example 15 Synthesis of 8- (4-phenylnaphthalen-1-yl) - [1,2,4] triazolo [1,5- a] pyridin-2-amine

The procedure of Preparation Example 2 was repeated except that Preparation Example 1 and 4-phenylnaphthalen-1-ylboronic acid were used as reactants to obtain 11.2 g (yield 71%) of the desired compound.

[HRMS]: 336

Preparation Example 16 Synthesis of 2-bromo-8- (4-phenylnaphthalen-1-yl) - [1,2,4] triazolo [1,5-

The procedure of Preparation Example 3 was repeated, except that Preparation Example 15 was used as a reactant, to obtain 10.9 g (yield: 83%) of the desired compound.

[HRMS]: 400

[Synthesis Example 1] Synthesis of Compound 1

Preparation Example 1 To 5.0 g (11.4 mmol) of 9H-carbazole and 2.1 g (12.5 mmol) of dioxane was added 100 mL. 0.2 g (1.1 mmol) of Pd (OAc) ₂ , 1.1 g (2.3 mmol) of XPhos and 4.7 g (34.1 mmol) of K ₂ CO ₃ were added and the mixture was refluxed at 120 ° C for 12 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (3.4 g, yield 57%).

_{^{1 H-NMR (in CDCl 3}} ): δ 9.29 (s, 1H), 9.00 (d, 2H), 8.60 (d, 1H), 8.31 (d, 1H), 8.17 (d, 1H), 8.10 (d, 2H), 7.85 (d, 1H), 7.63 (m, 4H), 7.58 (m, 3H), 7.51 (m, )

[HRMS]: 525

[Synthesis Example 2] Synthesis of Compound 10

Preparation Example 3 was added 7.0 g (15.9 mmol) and Preparation Example 6 6.5 g toluene 200 mL, EtOH 50 mL, H 2 O 50 mL in (17.5 mmol). _{Pd (PPh 3) 4 0.92 g} (0.8 mmol), Na 2 CO 3 5.1 g After the addition of (47.8 mmol) was heated 12 hours under reflux at 120 ℃. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (13.0 g, yield 74%).

[HRMS]: 601

[Synthesis Example 3] Synthesis of Compound 23

The procedure of Synthesis Example 1 was repeated except that Preparation Example 8 and 9H-carbazole were used to obtain 9.4 g (yield 77%) of the title compound.

[HRMS]: 476

[Synthesis Example 4] Synthesis of Compound 28

The procedure of Preparation Example 2 was repeated except that Preparation Example 5 and Preparation Example 12 were used to obtain 4.8 g (44%) of the desired compound.

[HRMS]: 603

[Synthesis Example 5] Synthesis of Compound 40

The procedure of Preparation Example 2 was repeated except that Preparation Example 1 and Preparation Example 4 were used as reactants to obtain the desired compound (3.6 g, yield 38%).

[HRMS]: 602

[Synthesis Example 6] Synthesis of Compound 54

The procedure of Preparation Example 11 was repeated, except that Preparation 8 and 9H-pyrido [2,3-b] indole were used as reactants to obtain the desired compound (3.4 g, yield 46%).

[HRMS]: 631

[Synthesis Example 7] Synthesis of Compound 65

The procedure of Synthesis Example 1 was repeated except that 9H-carbazole and Preparation Example 14 were used as a reactant, to obtain the object compound (5.5 g, yield: 57%).

[HRMS]: 486

[Synthesis Example 8] Synthesis of Compound 82

The procedure of Preparation Example 2 was repeated except that Preparation Example 6 and Preparation Example 14 were used as reactants, to obtain 4.0 g of the objective compound (yield: 44%).

[HRMS]: 562

[Synthesis Example 9] Synthesis of Compound 88

The procedure of Preparation Example 11 was repeated except that Preparation Example 16 and 9H-pyrido [2,3-b] indole were used as a reactant to obtain the desired compound (4.9 g, yield 51%).

[HRMS]: 487

[Synthesis Example 10] Synthesis of Compound 100

The procedure of Preparation Example 2 was repeated except that Preparation Example 12 and Preparation Example 16 were used as reactants to obtain the desired compound (4.7 g, yield 48%).

[HRMS]: 563

[Example 1] Production of blue organic EL device

Compound 1 synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured by the following procedure.

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, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

(30 nm) / Alq ₃ (30 nm) / LiF (0.2 nm) / Al (150 nm) on the ITO transparent electrode in the order of CuPc (10 nm) / TPAC (30 nm) / Mat 3 + 7% Flrpic Thereby preparing an organic EL device.

The structures of CuPc, TPAC, and Flrpic used are as follows.

[Examples 2 to 10] Preparation of blue organic EL device

10, 23, 28, 40, 54, 65, 82, 88 and 100 were used instead of the compound 1 used as a host material in the formation of the light emitting layer in Example 1, Thereby preparing a blue organic EL device.

[Comparative Example 1] Production of blue organic EL device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that CBP was used instead of the compound 1 used as a host material in forming the light emitting layer in Example 1.

[Evaluation Example 1]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the blue organic EL devices manufactured in Example 1 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Compound 1 7.38 456 6.20 Example 2 Compound 10 7.50 470 6.30 Example 3 Compound 23 7.45 475 6.44 Example 4 Compound 28 7.40 465 6.36 Example 5 Compound 40 7.55 480 6.33 Example 6 Compound 54 7.60 477 6.60 Example 7 Compound 65 7.45 485 6.20 Example 8 Compound 82 7.50 470 6.47 Example 9 Compound 88 7.44 466 6.36 Example 10 Compound 100 7.55 450 6.29 Comparative Example 1 CBP 7.80 474 5.80

As a result of the experiment, as shown in Table 1, the blue organic EL devices of Examples 1 to 100, in which the compound according to the present invention was used as a host material of the light emitting layer, Which is superior in terms of current efficiency and driving voltage.

Claims (7)

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

In Formula 1,
X ₁ to X ₃ are both N,
R ₁ and R ₂ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, an amino group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the, or the group condensed ring to which they are adjacent &Lt; / RTI &gt;
Wherein at least one of R ₁ and R ₂ has the structure of Formula 2 or Formula 3;
(2)

(3)

In Formula 2 or Formula 3,
Y ₁ to Y ₈ are each independently CR _4, wherein the plurality of R ₄ are the same or different;
R ₄ and R ₅ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, an amino group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the, or the group condensed ring to which they are adjacent Lt; / RTI &gt;
L ₁ is selected from a single bond, an arylene group having ₆ to ₆₀ carbon atoms, or a heteroarylene group having 5 to 60 nuclear atoms;
n is an integer from 0 to 4;
In the above R ₁ , R ₂ and R ₄ to R ₅ , 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 of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the arylamine group, each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₆ ~ 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 alkylsilyl 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 ~ C ₆₀ aryl phosphine oxide groups and may be substituted with C 1 ~ ₆ or more selected from the group consisting of an aryl amine of the C _60. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (4) to (6)
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Chemical Formulas 4 to 6,
X ₁ to X ₃ , Y ₁ to Y ₈ , R ₁ , R ₂ , R ₄ to R ₅ and L ₁ are the same as defined in claim 1. delete The compound according to claim 1, wherein R ₂ is a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and the heteroaryl group are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C ₆ to C ₆₀ 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 ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ group, the alkyl boron C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine oxide of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the group, and a C ₆ ~ C An arylamine group having 1 to ₆₀ carbon atoms, or an arylamine group having _{6 to 60} carbon atoms. 2. The compound according to claim 1, wherein L &lt; ₁ &gt; is a single bond, a phenylene group, or a biphenylene group. A cathode, and at least one organic 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, 2, 4 to 5. The organic electroluminescent device according to claim 6, wherein the organic compound layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer.