KR20160076355A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent luminescence, and to an organic electroluminescent device comprising the compound in at least one organic matter layer, which has improved properties such as light emitting efficiency, driving voltage, lifespan, etc. The compound is represented by chemical formula 1.

Description

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

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel condensed benzocarbazole compound having excellent hole injection and transport ability, An organic electroluminescent device having improved characteristics such as efficiency, driving voltage, and lifetime.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film 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 and Alq ₃ represented by the following formulas are widely known, and an anthracene derivative as a luminescent material has 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.

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

Korea public patent 2011-0066763

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

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

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

In Formula 1,

X ₁ and X ₂ are each independently selected from the group consisting of O, S, N (Ar ₁ ), and C (Ar ₂ ) (Ar ₃ );

R ₁ to R ₁₀ are the same or different and are each independently hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ An alkyloxyl 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 C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ is selected from an aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of,

Wherein _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₉ and R ₁₀ combine with each other to form N, O, S , Si, or a condensed aromatic ring containing at least one of Si and Si,

Ar ₁ to Ar ₃ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group , A 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 C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, is selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of,

In the above Ar ₁ to Ar ₃ and R ₁ to R ₁₀ , an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, are each independently a C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group, and the amine may be substituted with at least one member selected from the group consisting of a, where a plurality of substituents If hwandoel they may be the same or different from each other.

The present invention also provides 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 comprises a compound And an organic electroluminescent device.

Here, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer. The one or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, and an electron transporting layer.

The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent 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 of 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 improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<New Organic Compound>

The present invention relates to a novel condensed benzocarb which has a higher molecular weight than conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)) and has excellent driving voltage characteristics and efficiency Based compound.

6H-benzo [def] carbazole is similar in energy level to 9H-carbazole. The novel compound of the present invention having a condensed ring in 6H-benzo [def] carbazole has a wide energy band gap and a high triplet energy level due to the similar energy level to the conventional phosphorescent host.

The condensed benzocarbazole-based compound represented by the formula (1) of the present invention can have good phosphorescence efficiency characteristics based on a benzocarbazole structure having a high triplet energy and a chemically stable structure. As functional groups are introduced, they can have various energy bandgaps and chemical properties. In addition, it has a higher molecular weight than conventional host materials and has a relatively higher thermal stability. Thus, it has excellent lifetime characteristics of a material, and it is possible to manufacture an OLED device having improved power consumption by inducing an increase in power efficiency There is an advantage.

In the compound represented by the general formula (1) of the present invention, functional groups having excellent hole-transporting properties such as aryl groups (e.g., phenyl, biphenyl, terphenyl, triphenylene, naphthalene and anthracene) It can be used as a hole transporting layer, a light emission assisting layer, and the like because it has a wide band gap, excellent hole injection and transportability.

The compound represented by the general formula (1) according to the present invention may be a compound having a nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine, triazine, imidazole, pyrrole, quinoline or quinazoline, phosphine oxide, An electron injection layer, an electron transport layer, a hole barrier layer, and the like because it has excellent electron injection and transportability as a whole when a functional group having excellent electron injection and transportability is introduced.

According to the invention, and in the compound of the formula 1, X ₁ and X ₂ are the same or different from each other, consisting of each independently O, S, N (Ar _1), and _{C (Ar 2) (Ar 3} ) Lt; / RTI &gt; More specifically, at least one of X ₁ and X ₂ is N (Ar ₁ ), and more preferably both X ₁ and X ₂ are N (Ar ₁ ). Wherein each Ar &lt; ₁ &gt; may be the same or different.

In addition, R ₁ to R ₁₀ are to each other the same or different and each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl 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 alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, is selected from C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of. Wherein _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₉ and R ₁₀ combine with each other to form N, O, S , Si, or a condensed aromatic ring containing at least one of Si and Si.

In the present invention, R ₁ to R ₁₀ are the same or different and each independently represents hydrogen, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ aryl And an amine group.

In Formula 1, Ar ₁ to Ar ₃ are to each other the same or different and each independently represents a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, and is selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of.

More specifically, it is preferable that Ar ₁ to Ar ₃ are the same or different and each independently is a C ₆ to C ₆₀ aryl group, or a heteroaryl group having 5 to 60 nuclear atoms. For example, the C ₆ -C ₆₀ aryl group may be selected from a phenyl group, a biphenyl group, a naphthyl group, a phenanthrene group, a pyrenylene group, a triphenylene group, a fluorene group and the like, and the heteroaryl group having 5 to 60 nuclear atoms The group may be selected from pyridine, pyrimidine, triazine, quinazoline, carbazole, dibenzofuran, dibenzothiophene and the like.

In the above Ar ₁ to Ar ₃ and R ₁ to R ₁₀ , an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, are each independently a C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group, and the amine may be substituted with at least one member selected from the group consisting of a, where a plurality of substituents If hwandoel they may be the same or different from each other.

The compound represented by the formula (1) according to the present invention may be further exemplified by any of the following C-1 to C-7.

In the compounds represented by the above-mentioned C-1 to C-7, Ar ₁ to Ar ₃ and R ₁ to R ₁₀ are the same as defined in the formula (1).

Particularly, in the present invention, when an aromatic ring or a heteroaromatic ring is introduced as a substituent at a position of Ar ₁ in the present invention, a phosphorescent host capable of enhancing electron mobility and balancing holes and electrons in the light emitting layer and maximizing efficiency characteristics with a thermally stable structure There is an advantage as a material.

According to a preferred embodiment of the present invention, Ar ₁ is a substituent represented by the following formula (2) or may be a phenyl group.

In Formula 2,

* Represents a moiety bonded to Formula 1;

L is a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms and is preferably a single bond or a phenylene group or a biphenylene group.

Y ₁ to Y ₅ are the same or different and are each independently N or C (R ₁₁ ), provided that at least one of Y ₁ to Y ₅ is N, wherein at least two of Y ₁ to Y ₅ are C ₁₁ ), a plurality of R &lt; ₁₁ &gt; s may be the same or different from each other even if they are the same,

R ₁₁ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of the an aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy C ₁ ~ C ₄₀ of the alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero A C ₆ to C ₄₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ aryl phosphine group, in combination with a C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups (e.g., L, the other R ₁₁ which are adjacent) to a condensed ring Can be formed.

In R ₁₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, an aryloxycarbonyl group, an aryloxycarbonyl 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, a C ₆ to C ₄₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ 1 or more substituents selected from the group consisting of C ₄₀ aryl silyl Substituted or may be unsubstituted. When there are a plurality of substituents, they may be the same or different.

According to the present invention, the substituent represented by the above-mentioned formula (2) may be further exemplified by any one of the following substituents A-1 to A-15. However, it is not particularly limited.

In the above A-1 to A-15,

L and R &lt; ₁₁ &gt; are the same as defined in the above formula (2)

p is an integer of 0 to 4, when said n is 0, means that a hydrogen substituent is replaced by R _12, and doedoe wherein n is an integer when the hydrogen of a 1 to 4 is substituted with R _12, wherein R ₁₂ is When there are a plurality of them, they may be the same or different from each other,

R ₁₂ is each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , an aryloxy group of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₄₀ heteroaryl group of the aryl group, the number of nuclear atoms of 5 to 40 group, C ₆ ~ C _{40-C 1} ~ alkyloxy group of C ₄₀ , C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups , in combination with a C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups (e. g., such as L, R ₁₁ or other R ₁₂₎ to the condensed ring Can be formed.

In R ₁₂ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ 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, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ values in the aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group one or more substituents selected from the group consisting of Or unsubstituted or ring and, wherein when the plurality of individual substituents, they may be the same or different from each other.

According to a preferred example of the present invention, it is preferable that both of X ₁ and X ₂ are N (Ar ₁ ), and at least one of Ar ₁ is a substituent represented by the general formula (2).

The compound of the present invention described above can be further compounded by a compound represented by any of the following formulas (R1) to (R250). However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

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

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

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

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. 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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 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 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 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 of the carbons, preferably one to three carbons, Or &lt; RTI ID = 0.0 &gt; Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means 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.

&Lt; Organic electroluminescent device &

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of 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. have. More specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transporting layer, or a hole transporting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as a host material. The light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably includes a hole transporting layer, The auxiliary layer may include a compound represented by the above formula (1). On the other hand, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).

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 used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: 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.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO2 / 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 ordinary 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 A4

<Step 1> Synthesis of A1

Iodobenzene, 24.5 g (120.0 mmol), Cu powder, 1.8 g (28.0 mmol), K ₂ CO _3, 11.1 g (80.0 mmol) of nitrobenzene 60 ml were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound A1 (9.0 g, 33.6 mmol, yield 84%).

GC-Mass (theory: 267.32 g / mol, measured: 267 g / mol)

2H), 7.83-7.88 (m, 4H), 8.12 (d, 2H)

<Step 2> Synthesis of A2

9.0 g (33.6 mmol) of A1, N-bromosuccinimide (NBS), 6.0 g (33.6 mmol) of DM and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A2 (3.7 g, 10.8 mmol, yield 32%).

GC-Mass (theory: 346.22 g / mol, measurement: 346 g / mol)

1H-NMR:? 7.45-7.54 (m, 5H), 7.83-7.88 (m, 5H)

<Step 3> Synthesis of A3

Pd (PPh ₃ ) ₄ and potassium carbonate, 4.5 g (32.3 mmol) of A2, 3.7 g (10.8 mmol), 2-nitrophenylboronic acid, 1.3 g And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A3 (3.4 g, 8,7 mmol, yield: 81%).

GC-Mass (theory: 388.42 g / mol, measurement: 388 g / mol)

^{1 H-NMR: δ 7.45 ~} 7.65 (m, 6H), 7.82 ~ 8.05 (m, 8H), 8.12 (d, 2H)

<Step 4> Synthesis of A4

3.4 g (8.7 mmol) of A3, 5.7 g (21.8 mmol) of triphenylphosphine and 40 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound A4 (2.3 g, 6.4 mmol, yield 74%).

GC-Mass (356.42 g / mol, measured: 356 g / mol)

¹ H-NMR:? 7.25 (m, 1H), 7.45-7.64 (m, 7H), 7.82-7.87 (m, 4H), 8.10-8.12

[Preparation Example 2] Synthesis of B4

<Step 1> Synthesis of B1

(40.0 mmol) of 6H-benzo [def] carbazole, 41.3 g (120.0 mmol) of Cu powder, 1.8 (3-chlorophenyl) g (28.0 mmol), K ₂ CO _3, 11.1 g (80.0 mmol) and 60 ml of nitrobenzene were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound B1 (8.8 g, 32.8 mmol, yield 82%).

GC-Mass (calculated: 498.58 g / mol, measured: 498 g / mol)

8H), 7.71 (s, 2H), 7.82-7.87 (m, 4H), 8.09-8.11 (m, 3H), 8.25-8.27 (m, 5H)

<Step 2> Synthesis of B2

8.8 g (32.8 mmol) of B1, N-bromosuccinimide (NBS), 5.8 g (32.8 mmol) of DMF and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain objective compound B2 (4.0 g, 6.9 mmol, yield 21%).

GC-Mass (calculated: 577.47 g / mol, measured: 577 g / mol)

1H-NMR:? 7.41-50 (m, 8H), 7.82-7.86 (m, 5H), 8.09-8.11 (m, 3H), 8.24-8.26

<Step 3> Synthesis of B3

Pd (PPh ₃ ) ₄ and potassium carbonate, 2.9 g (20.7 mmol) of B2, 4.0 g (6.9 mmol), 2-nitrophenylboronic acid, 0.8 g And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound B3 (3.5 g, 5.6 mmol, yield 81%).

GC-Mass (calculated: 619.67 g / mol, measured: 619 g / mol)

^{1 H-NMR: δ 7.41 ~} 50 (m, 8H), 7.65 (m, 1H), 7.82 ~ 7.89 (m, 6H), 8.00 ~ 8.11 (m, 5H), 8.23 ~ 8.25 (m, 5H)

<Step 4> Synthesis of B4

3.5 g (5.6 mmol) of B3, 3.7 g (13.9 mmol) of triphenylphosphine and 40 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound B4 (2.6 g, 3.3 mmol, yield 78%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

¹ H-NMR:? 7.28 (m, 1H). (M, 4H), 8.03-8.12 (m, 4H), 8.23-8.25 (m, 5H), 10.0

[Preparation Example 3] Synthesis of C4

<Step 1> Synthesis of C1

2-chloro-4-phenylquinazoline, 28.9 g (120.0 mmol), Cu powder, 1.8 g (28.0 mmol), K ₂ CO _3, 11.1 g (40.0 mmol) of 6H- 80.0 mmol) and 60 ml of nitrobenzene were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound C1 (9.0 g, 33.6 mmol, yield 84%).

GC-Mass (calculated: 395.45 g / mol, measured: 395 g / mol)

^{1 H-NMR: δ 7.41 ~} 50 (m, 3H), 7.71 (s, 2H), 7.80 ~ 7.87 (m, 7H), 8.05 ~ 8.11 (m, 5H)

<Step 2> Synthesis of C2

9.0 g (33.6 mmol) of C1, NBS (N-bromosuccinimide), 5.8 g (32.8 mmol) of C1 and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound C2 (3.7 g, 7.7 mmol, yield: 23%).

GC-Mass (calculated: 474.35 g / mol, measured: 474 g / mol)

1 H-NMR:? 7.41-50 (m, 3H), 7.80-7.88 (m, 8H), 8.05-8.10 (m,

<Step 3> Synthesis of C3

Pd (PPh ₃ ) ₄ and potassium carbonate, 3.2 g (23.2 mmol) of C2, 3.7 g, 7.7 mmol, 2-nitrophenylboronic acid, 0.9 g (7.7 mmol) And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound C3 (3.2 g, 4.0 mmol, yield 79%).

GC-Mass (calculated: 516.55 g / mol, measured: 516 g / mol)

^{1 H-NMR: δ 1H-} NMR: δ 7.41 ~ 49 (m, 3H), 7.65 (m, 1H), 7.80 ~ 8.09 (m, 16H)

<Step 4> Synthesis of C4

3.2 g (6.1 mmol) of C3, 4.0 g (15.3 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene were added under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound C4 (2.2 g, 4.6 mmol, yield 76%).

GC-Mass (calculated: 484.55 g / mol, measured: 484 g / mol)

7H), 8.03-8.10 (m, 6H), 10.0 (s, 1H), 7.41-7.50 (m, 4H) 1H)

[Preparation Example 4] Synthesis of D3

<Step 1> Synthesis of A1

Iodobenzene, 24.5 g (120.0 mmol), Cu powder, 1.8 g (28.0 mmol), K ₂ CO _3, 11.1 g (80.0 mmol) of nitrobenzene 60 ml were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A1 (9.0 g, 33.6 mmol, yield 84%).

GC-Mass (theory: 267.32 g / mol, measured: 267 g / mol)

^{1 H-NMR: δ 7.46 ~} 7.55 (m, 5H), 7.70 (s, 2H), 7.83 ~ 7.88 (m, 4H), 8.12 (d, 2H)

<Step 2> Synthesis of A2

9.0 g (33.6 mmol) of A1, N-bromosuccinimide (NBS), 6.0 g (33.6 mmol) of DM and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound A2 (3.7 g, 10.8 mmol, yield 32%).

GC-Mass (theory: 346.22 g / mol, measurement: 346 g / mol)

1H-NMR:? 7.45-7.54 (m, 5H), 7.83-7.88 (m, 5H)

<Step 3> Synthesis of D1

2.2 g (10.8 mmol), 0.6 g (5 mol%) of Pd (PPh ₃ ) ₄ , and potassium carbonate, 4.5 g (32.3 mmol) and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound D1 (3.7 g, 8,7 mmol, yield 81%).

GC-Mass (calculated: 422.86 g / mol, measured: 422 g / mol)

^{1 H-NMR: δ 7.44 ~} 7.56 (m, 5H), 7.71 (d, 1H), 7.82 ~ 8.87 (m, 5H), 8.11 (d, 2H), 8.25 (d, 1H), 8.27 (s, 1H )

<Step 4> Synthesis of D2

3.7 g (8.7 mmol) of D1, 5.7 g (21.8 mmol) of triphenylphosphine and 40 ml of 1,2-dichlorobenzene were placed in a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound D2 (2.5 g, 6.4 mmol, yield 74%).

GC-Mass (theory: 390.86 g / mol, measurement: 390 g / mol)

^{1 H-NMR: δ 7.08 (} s, 1H), 7.44 ~ 7.57 (m, 7H), 7.82 ~ 8.84 (m, 4H), 8.11 (d, 2H), 10.1 (s, 1H)

<Step 5> Synthesis of D3

Pd (PPh ₃ ) ₄ , and potassium carbonate, 2.7 g (19.3 mmol), and 80 ml (0.15 mmol) of D2, 2.5 g, 6.4 mmol, phenylboronic acid, 0.8 g / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol was added thereto, followed by stirring at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound D3 (2.3 g, 5.2 mmol, yield 81%).

GC-Mass (calculated: 432.51 g / mol, measured: 432 g / mol)

¹ H-NMR:? 7.44-7.57 (m, 10H), 7.69 (d, 1H), 7.77-7.88 (m, 6H)

[Preparation Example 5] Synthesis of E4

<Step 1> Synthesis of E2

6.5 g (33.6 mmol) of E1, 6.0 g (33.6 mmol) of NBS (N-bromosuccinimide) and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound E2 (2.9 g, 10.8 mmol, yield 32%).

GC-Mass (calculated value: 271.11 g / mol, measured: 271 g / mol)

^{1 H-NMR: δ 7.83 ~} 7.88 (m, 5H), 8.10 (d, 2H)

<Step 2> Synthesis of E3

(10.8 mmol), 2-nitrophenylboronic acid, 1.3 g (10.8 mmol), 0.6 g (5 mol%) of Pd (PPh ₃ ) ₄ and potassium carbonate, 4.5 g (32.3 mmol) of E2, 2.9 g And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound E3 (2.7 g, 8,7 mmol, yield 81%).

GC-Mass (theory: 313.31 g / mol, measurement: 313 g / mol)

^{1 H-NMR: δ 7.65 (} m, 1H), 7.79 ~ 8.05 (m, 8H), 8.10 (d, 2H)

<Step 3> Synthesis of E4

2.7 g (8.7 mmol) of E3, 5.7 g (21.8 mmol) of triphenylphosphine and 40 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound E4 (1.8 g, 6.4 mmol, yield 74%).

GC-Mass (281.31 g / mol, measured: 281 g / mol)

¹ H-NMR:? 7.27 (m, IH), 7.51 (m, IH), 7.63 (d, IH), 7.83-8.88

[Preparation Example 6] Synthesis of F4

<Step 1> Synthesis of F2

Under nitrogen flow, 7.0 g (33.6 mmol) of F1, N-bromosuccinimide (NBS), 6.0 g (33.6 mmol) of DMF and 90 ml of DMF were mixed and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound F2 (3.1 g, 10.8 mmol, yield 32%).

GC-Mass (287.17 g / mol, measured: 287 g / mol)

^{1 H-NMR: δ 7.83 ~} 7.91 (m, 5H), 8.10 (d, 2H)

<Step 2> Synthesis of F3

In a nitrogen stream F2, 3.1g, (10.8 mmol) , 2-nitrophenylboronic acid, 1.3g (10.8 mmol), Pd (PPh 3) 4, and potassium carbonate, 4.5g (32.3 mmol) of 0.6g (5 mol%) And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound F3 (2.8 g, 8.5 mmol, yield 79%).

GC-Mass (theory 329.37 g / mol, measurement 329 g / mol)

^{1 H-NMR: δ 7.58 (} m, 1H), 7.77 ~ 8.02 (m, 8H), 8.10 (d, 2H)

<Step 3> Synthesis of F4

2.8 g (8.5 mmol) of F3, 5.6 g (21.2 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound F4 (2.0 g, 6.6 mmol, yield 78%).

GC-Mass (298.37 g / mol, measured: 298 g / mol)

^{1 H-NMR: δ 7.24 (} m, 1H), 7.48 (m, 1H), 7.60 (d, 1H), 7.80 ~ 8.85 (m, 4H), 8.08 (d, 3H), 10.0 (s, 1H)

[Preparation Example 7] Synthesis of G4

<Step 1> Synthesis of FG2

7.3 g (33.6 mmol) of G1, 6.0 g (33.6 mmol) of NBS (N-bromosuccinimide) and 90 ml of DMF were mixed under a nitrogen stream and stirred at 60 ° C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound G2 (2.3 g, 7.7 mmol, yield: 23%).

GC-Mass (297.19 g / mol, measured: 297 g / mol)

^{1 H-NMR: δ 1.99 (} s, 6H), 7.82 ~ 7.90 (m, 5H), 8.11 (d, 2H)

<Step 2> Synthesis of F3

In a nitrogen stream F2, 2.3g, (7.7 mmol) , 2-nitrophenylboronic acid, 0.9g (7.7 mmol), 0.4g Pd (PPh 3) of (5 mol%) _4, and potassium carbonate, 3.2g (23.2 mmol) And 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound G3 (2.1 g, 6.1 mmol, yield 79%).

GC-Mass (calculated: 339.39 g / mol, measured: 339 g / mol)

^{1 H-NMR: δ 1.99 (} s, 6H), 7.55 (m, 1H), 7.76 ~ 8.01 (m, 8H), 8.08 (d, 2H)

<Step 3> Synthesis of F4

2.1 g (6.1 mmol) of F3, 4.0 g (15.3 mmol) of triphenylphosphine and 20 ml of 1,2-dichlorobenzene were added under a nitrogen stream, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removal of the organic layer solvent, the residue was purified by column chromatography to obtain the target compound G4 (1.4 g, 4.6 mmol, yield 76%).

GC-Mass (theory: 307.39 g / mol, measurement: 307 g / mol)

^{1 H-NMR: δ 1.99 (} s, 6H), 7.22 (m, 1H), 7.45 (m, 1H), 7.57 (d, 1H), 7.78 ~ 8.82 (m, 4H), 8.06 (d, 3H), 10.0 (s, 1 H)

[Synthesis Example 1] Synthesis of R1

(5 mol%) of Pd ₂ (dba (5 mol%)) in the presence of nitrogen and a nitrogen stream in the same manner as in Example 1 except that A4, 2.3 g (6.4 mmol), 5'-chloro-1,1 ' ) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 19.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.4 g (4.1 mmol, yield 63%) of the target compound R1.

GC-Mass (calculated: 584.71 g / mol, measured: 584 g / mol)

[Synthesis Example 2] Synthesis of R2

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2 -chloro-4,6-diphenylpyrimidine, 1.9g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- tert -butylphosphine, 0.1 g (0.3 mmol) of sodium tert-butoxide, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.3 g (4.0 mmol, yield 62%) of the objective compound R2.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 3] Synthesis of R3

Pd ₂ (dba) ₃ (5 mol%), 0.3 g (5 mol%) of A ₂ , 3'-chloro-6'- , 0.1 g (0.3 mmol) of tri- tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.5 g (4.3 mmol, yield 67%) of the desired compound R3.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 4] Synthesis of R10

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (4-chlorophenyl) pyridine, 1.3g (7.1mmol), 0.3g (5 mol%) of _{Pd 2 (dba) 3, tri-} tert -butylphosphine, 0.1 g (0.3 mmol), sodium tert-butoxide (1.9 g, 19.3 mmol) and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.0 g (3.9 mmol, yield 61%) of the target compound R10.

GC-Mass (theory: 509.60 g / mol, measurement: 509 g / mol)

[Synthesis Example 5] Synthesis of R11

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (3-chlorophenyl) pyridine, 1.3g (7.1mmol), 0.3g (5 mol%) of _{Pd 2 (dba) 3, tri-} tert -butylphosphine, 0.1 g (0.3 mmol), sodium tert-butoxide (1.9 g, 19.3 mmol) and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.1 g (4.1 mmol, yield 64%) of the target compound R11.

GC-Mass (theory: 509.60 g / mol, measurement: 509 g / mol)

[Synthesis Example 6] Synthesis of R12

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (2-chlorophenyl) pyridine, 1.3g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- tert -butylphosphine, 0.1 g (0.3 mmol), sodium tert-butoxide (1.9 g, 19.3 mmol) and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.1 g (4.1 mmol, yield 63%) of the target compound R12.

GC-Mass (theory: 509.60 g / mol, measurement: 509 g / mol)

[Synthesis Example 7] Synthesis of R14

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (4-chlorophenyl) -4,6-diphenylpyridine, 2.4g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.0 g (4.6 mmol, yield 71%) of the target compound R14.

GC-Mass (calculated: 661.79 g / mol, measured: 661 g / mol)

[Synthesis Example 8] Synthesis of R15

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 4- (4-chlorophenyl) -2,6-diphenylpyrimidine, 2.4g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.1 g (4.7 mmol, yield 73%) of the desired compound R15.

GC-Mass (calculated: 661.79 g / mol, measured: 661 g / mol)

[Synthesis Example 9] Synthesis of R16

2.3 g (6.4 mmol) of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 2.4 g (7.1 mmol) of Pd ₂ (dba) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.1 g (4.7 mmol, yield 72%) of the target compound R16.

GC-Mass (calculated: 661.79 g / mol, measured: 661 g / mol)

[Synthesis Example 10] Synthesis of R18

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 4- (3-chlorophenyl) -2,6-diphenylpyridine, 2.4g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.0 g (4.5 mmol, yield 70%) of the objective compound R18.

GC-Mass (calculated: 661.79 g / mol, measured: 661 g / mol)

[Synthesis Example 11] Synthesis of R19

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (3-chlorophenyl) -4,6-diphenylpyrimidine, 2.4g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.0 g (4.5 mmol, yield 70%) of the target compound R19.

GC-Mass (calculated: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 12] Synthesis of R20

2.3 g (6.4 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 2.4 g (7.1 mmol) of Pd ₂ (dba) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.1 g (4.6 mmol, yield 72%) of the target compound R20.

GC-Mass (theory: 663.77 g / mol, measurement: 663 g / mol)

[Synthesis Example 13] Synthesis of R22

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 4- (3-chlorophenyl) -2,6-diphenylpyridine, 2.4g (7.1mmol), Pd 2 (dba) of _{0.3g (5 mol%) 3,} tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.0 g (4.1 mmol, yield 64%) of the target compound R22.

GC-Mass (calculated: 661.79 g / mol, measured: 661 g / mol)

[Synthesis Example 14] Synthesis of R23

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2- (2-chlorophenyl) -4,6-diphenylpyrimidine, 2.4g (7.1mmol), 0.3g (5 mol%) of Pd ₂ (dba) _3, tri- 0.1 g (0.3 mmol) of tert- butylphosphine, 1.9 g (19.3 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.6 g (4.0 mmol, yield 62%) of the target compound R19.

GC-Mass (calculated: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 15] Synthesis of R24

2.3 g (6.4 mmol) of 2- (2-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 2.4 g (7.1 mmol) of Pd ₂ (dba) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.8 g (4.3 mmol, yield 66%) of the target compound R24.

GC-Mass (theory: 663.77 g / mol, measurement: 663 g / mol)

[Synthesis Example 16] Synthesis of R25

Under nitrogen gas stream, A4, 2.3g (6.4mmol), 2 -chloro-4-phenylquinazoline, 1.7g (7.1mmol), 0.3g (5 mol%) Pd 2 (dba) of _3, tri- tert -butylphosphine, 0.1g (0.3 mmol), sodium tert-butoxide (1.9 g, 19.3 mmol) and 50 ml of toluene, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.5 g (4.4 mmol, yield 69%) of the target compound R25.

GC-Mass (calculated: 560.65 g / mol, measured: 560 g / mol)

[Synthesis Example 17] Synthesis of R45

Pd ₂ (dba) ₃ , tri- tert- butylphosphine, 0.1 g (0.2 mmol) and Sodium (0.2 mmol) of B4, 2.6 g (4.4 mmol), iodobenzene, 1.3 g (13.1 mmol) of tert-butoxide and 50 ml of toluene were placed, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.2 g (3.3 mmol, yield 75%) of the objective compound R45.

GC-Mass (theory: 395.49 g / mol, measurement: 395 g / mol)

[Synthesis Example 18] Synthesis of R50

Pd ₂ (dba) ₃ , tri- tert- butylphosphine, 0.2 g (0.2 mmol) of sodium chloride, and 0.2 g (0.2 mmol) of C4, 2.2 g 1.3 g (13.9 mmol) of tert-butoxide and 50 ml of toluene were placed, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 1.49 g (3.4 mmol, yield 74%) of the target compound R50.

GC-Mass (calculated: 560.65 g / mol, measured: 560 g / mol)

[Synthesis Example 19] Synthesis of R70

1.8 g (6.4 mmol) of E4, 2.4 g (7.1 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 0.3 g ₂ (dba) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.9 g (2.9 mmol, yield 72%) of the target compound R70.

GC-Mass (calculated: 614.74 g / mol, measured: 614 g / mol)

[Synthesis Example 20] Synthesis of R120

2.0 g (6.4 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 2.4 g (7.1 mmol) of P4 and 0.3 g ₂ (dba) into a _{3, tri- tert -butylphosphine, 0.1g (} 0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol ) and 50ml of Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.8 g (3.1 mmol, yield 72%) of the target compound R120.

GC-Mass (theory: 604.72 g / mol, measurement: 604 g / mol)

[Synthesis Example 21] Synthesis of R170

(4.6 mmol) of G4, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 1.8 g (5.1 mmol) 0.1 g (0.2 mmol) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine, 1.3 g (13.9 mmol) of sodium tert-butoxide and 50 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.0 g (2.2 mmol, yield 72%) of the target compound R170.

GC-Mass (calculated: 588.66 g / mol, measured: 588 g / mol)

[Synthesis Example 22] Synthesis of R220

2.3 g (5.2 mmol) of D3, 1.4 g (5.7 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 0.2 g (5 mol%) of Pd _{2 (dba) 3, tri- tert} -butylphosphine, 0.1g (0.3mmol) and Sodium tert-butoxide, put 1.5g (15.7mmol) and 50ml of Toluenel was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.7 g (3.6 mmol, yield 69%) of the objective compound R220.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[Synthesis Example 23] Synthesis of R225

D3, 2.3g (5.2mmol), 2 -chloro-4-phenylquinazoline, 1.4g (5.7mmol), 0.2g (5 mol%) of _{Pd 2 (dba) 3, tri-} tert -butylphosphine, 0.2g was conducted in a nitrogen atmosphere (0.3 mmol), sodium tert-butoxide, 1.5 g (15.7 mmol) and 50 ml of toluene were placed, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.3 g (3.6 mmol, yield 69%) of the objective compound R225.

GC-Mass (theory: 636.74 g / mol, measurement: 636 g / mol)

[Examples 1 to 17] Preparation of green organic EL device

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

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / R1, R10, R11, R12, R15, R16, R18, R19, R20, R22, R23, R24, R45, R70, R170, each of the compounds of the R220 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) the organic EL element by sequentially stacked with Respectively.

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

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound R1 as a luminescent host material in forming the light emitting layer.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm &lt; 2 &gt; were measured for each of the green organic EL devices manufactured in Examples 1 to 17 and Comparative Example 1, .

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 R1 5.9 515 41.2 Example 2 R10 6.1 515 42.1 Example 3 R11 6.0 514 41.2 Example 4 R12 5.8 515 41.4 Example 5 R15 6.6 514 40.2 Example 6 R16 6.4 515 40.3 Example 7 R18 6.0 515 40.7 Example 8 R19 6.2 515 42.3 Example 9 R20 5.8 515 44.0 Example 10 R22 5.5 515 42.5 Example 11 R23 6.8 514 41.3 Example 12 R24 5.7 515 43.6 Example 13 R45 5.6 515 43.8 Example 14 R70 6.0 515 44.5 Example 15 R120 5.0 515 40.1 Example 16 R170 4.5 515 39.5 Example 17 R220 5.5 515 43.1 Comparative Example 1 CBP 7.2 517 36.1

As shown in Table 1, the compound (R1, R10, R11, R12, R15, R16, R18, R19, R20, R22, R23, R24, R45, R70, R1120, R170, , The green organic EL device of Example 1-17 exhibits superior performance in terms of efficiency and driving voltage as compared with the conventional green organic EL device using CBP (Comparative Example 1).

[Examples 18 to 23] Preparation of red organic EL device

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

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

On this ITO transparent electrode, a compound of m-MTDATA (60 nm) / TCTA (80 nm) / R2, R3, R14, R25, R50 and R225 + 10% (piq) ₂ Ir (acac) 10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[Comparative Example 2]

A red organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound of Synthesis Example 2 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 18 to 23 and Comparative Example 2 are as follows.

[Evaluation Example 2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 18 to 23 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 18 R2 4.1 621 12.7 Example 19 R3 4.4 621 11.5 Example 20 R14 4.4 620 10.9 Example 21 R25 3.8 621 13.7 Example 22 R50 3.5 621 13.2 Example 23 R225 3.5 621 12.8 Comparative Example 2 CBP 5.5 622 9.1

As shown in Table 2, the red organic electroluminescent devices of Examples 18 to 23 using the compound according to the present invention as the material of the light emitting layer were the red organic electroluminescent device using CBP as the material of the light emitting layer (Comparative Example 2 ), It was found that it shows excellent performance in terms of efficiency and driving voltage.

Claims (8)

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

In Formula 1,
X ₁ and X ₂ are each independently selected from the group consisting of O, S, N (Ar ₁ ), and C (Ar ₂ ) (Ar ₃ );
R ₁ to R ₁₀ are the same or different and are each independently hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ An alkyloxyl 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 C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ is selected from an aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of,
Wherein _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₉ and R ₁₀ combine with each other to form N, O, S , Si, or a condensed aromatic ring containing at least one of Si and Si,
Ar ₁ to Ar ₃ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group , A 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 C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, is selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of,
In the above Ar ₁ to Ar ₃ and R ₁ to R ₁₀ , an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, are each independently a C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group, and the amine may be substituted with at least one member selected from the group consisting of a, where a plurality of substituents If hwandoel they may be the same or different from each other. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (C-1) to (C-7):

In the compounds represented by the above-mentioned C-1 to C-7,
Ar ₁ to Ar ₃ , and R ₁ to R ₁₀ are the same as defined in claim 1. 3. The method of claim 2,
Wherein at least one of Ar &lt; ₁ &gt; is a substituent represented by the following formula (2): &lt; EMI ID =
(2)

In Formula 2,
* Represents a moiety bonded to Formula 1;
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,
Y ₁ to Y ₅ are the same as or different from each other and each independently N or C (R ₁₁ ), provided that at least one of Y ₁ to Y ₅ is N, and when R ₁₁ is plural, Different;
R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, 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, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms , C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups , C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl group, or of, or adjacent groups to be bonded to form a condensed ring;
In R ₁₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ 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, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ values in the aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group one or more substituents selected from the group consisting of It may be, and wherein when the substituent is plural, they may be the same or different from each other. 3. The method of claim 2,
At least one of said Ar ₁ is a compound wherein the substituent represented by any one of the following A-1 to A-15.

In the above A-1 to A-15,
L and R &lt; ₁₁ &gt; are as defined in the above formula (2)
p is an integer of 0 to 4,
R ₁₂ represents a group selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl 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, a C C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or, or adjacent groups of binding to, and may form a condensed ring, wherein when R is ₁₂ with a plurality, they each other Identical or different;
In R ₁₂ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ 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, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ values in the aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group one or more substituents selected from the group consisting of It may be, and wherein when said plurality of individual substituents, they may be the same or different from each other. The method according to claim 1,
X ₁ and X ₂ are All are N (Ar ₁ )
Ar ₁ is independently an aryl group of C ₆ to C ₆₀ or a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and heteroaryl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ aralkyl group, Wherein the aryl group is substituted or unsubstituted with at least one substituent selected from the group consisting of aryl phosphine groups, C ₆ to C ₄₀ aryl phosphine oxide groups and C ₆ to C ₄₀ arylsilyl groups. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by formula (1) according to any one of claims 1 to 5. The organic electroluminescent device according to claim 6, wherein the compound represented by Formula 1 is used as a phosphorescent host of the light emitting layer. The organic electroluminescent device according to claim 6, wherein the one or more organic layers including the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, and an electron injecting layer.