KR20200061721A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent electron transporting ability and luminescent ability, and an organic electroluminescent device having improved properties such as luminous efficiency, driving voltage, and lifespan by containing the compound in one or more organic material layers. The compound represented by chemical formula 1 according to the present invention can be used as an organic material layer material of the organic electroluminescent device.

Description

Organic compounds and organic electroluminescent devices using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more specifically, an organic compound having excellent electron transport ability and improved characteristics such as luminous efficiency, driving voltage, and lifetime by including it in one or more organic material layers. It relates to an electroluminescent device.

The study of organic electroluminescent (EL) devices (hereinafter simply referred to as'organic EL devices') that led to blue electroluminescence using anthracene single crystals in 1965 from the point of view of organic thin film emission by Bernanose in the 1950s An organic EL device having a stacked structure divided by a functional layer of a hole layer and a light emitting layer by (Tang) has been proposed. Since then, in order to make a high-efficiency, high-life organic EL device, it has been developed in the form of introducing each characteristic organic layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode to the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.

The light emitting layer forming material of the organic EL device can be divided into blue, green, and red light emitting materials according to the light emission color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better natural colors. In addition, a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer. The dopant material may 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 that of fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

To date, the hole injection layer and the hole transport layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formula are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials. Particularly, among the light-emitting materials, a metal complex compound containing Ir, such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _2, etc., which has a great advantage in terms of efficiency improvement, is a blue, green, red dopant material Is being used as To date, CBP has shown excellent properties as a phosphorescent host material.

However, the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device.

An object of the present invention is to provide a novel compound that can be used as an organic material layer material, specifically a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material of an organic electroluminescent device, which is excellent in electron injection and transport, luminescence, etc. Is done.

In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compounds described above.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1), specifically an electron transport layer or a compound for an electron transport auxiliary layer.

In Chemical Formula 1,

A plurality of Xs are the same as or different from each other, each independently N or CR ₃ ,

R ₁ and R ₂ are the same as or different from each other, and each independently selected from an alkyl group of C ₁ to C ₄₀ and an aryl group of C ₆ to C ₄₀ , or they may combine with adjacent groups to form a condensed ring,

Y is O, S or Se,

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

A plurality of Z are the same as or different from each other, and each independently N or CR ₄ , provided that at least one of the plurality of Z is N,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, and a C ₃ to C ₄₀ cycloalkyl group. , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , arylox of C ₆ to C ₆₀ Period, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl force wave group, C ₆ ~ C ₆₀ aryl mono Phosphinicosuccinic group, C ₆ ~ C ₆₀ of the diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

R ₃ to R ₄ are the same as or different from each other, and each independently hydrogen, 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 ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Group consisting of aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group Or they may combine with adjacent groups to form a condensed ring;

The arylene group and heteroarylene group of L, the alkyl group and aryl group of R ₁ to R _2, the alkyl group of the R ₃ to R ₄ and Ar ₁ to Ar ₂ , alkenyl group, alkynyl group, aryl group, heteroaryl group , Aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, phosphine group, phosphine oxide group, and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ may be substituted by one substituent at least one selected from the group consisting of an aryl amine of the C _60, the case when the substituent is plural, they may be the same or different from each other.

In addition, the present invention provides an electron transport layer or an electron transport auxiliary layer comprising the compound represented by Formula 1 described above.

In addition, the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the organic material layers of the one or more layers includes an organic electric field comprising a compound represented by Formula 1 described above A light emitting device is provided.

Here, the organic material layer containing 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 injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.

Since the compound represented by Chemical Formula 1 according to the present invention has excellent electron transport ability and luminescence ability, it can be used as an organic material layer material for an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host, electron transport layer or electron transport auxiliary layer material, it has higher thermal stability, lower driving voltage, faster mobility, and higher current efficiency than conventional host materials or electron transport materials. And it is possible to manufacture an organic electroluminescent device having a long life property, and furthermore, it can be effectively applied to a full color display panel with improved performance and life.

Hereinafter, the present invention will be described in detail.

<New organic compound>

In the compound represented by Chemical Formula 1 according to the present invention, fluorene and nitrogen-containing heteroaromatic rings (eg, azine) are located at both ends of the molecule, and 2,6-dibenzoic moieties are present between them. It has a basic framework structure that is linked by a linker. Here, the fluorene group may be directly connected to a 2,6-dibenzoic moiety or may be connected through a separate linker (L).

Since the compound represented by Chemical Formula 1 of this structure uses a 2,6-dibenzoic moiety (eg, Y-containing ring) as a linker connecting a fluorene group and a nitrogen-containing heteroaromatic ring, it is phenyl as a linker. Compared to a compound having the same structure in which a ren group or a biphenylene group is introduced, it is electrochemically stable, and the glass transition temperature (Tg) of the compound is significantly increased, thereby increasing thermal stability. Accordingly, it is possible to improve the long life characteristics of the organic light emitting device comprising the above-described compound. Particularly, in the present invention, a 2,6-dibenzoic moiety is employed as a linker, but an electron withdrawal (EWG) is bound to the 6th position than other carbon sites (7 or 8) which are linear positions. Accordingly, since the EWG group is positioned on a relatively non-planar surface, triplet energy can be maintained high, thereby preventing trapping and improving efficiency.

More specifically, the compound of Formula 1 uses a dibenzoic moiety (eg, dibenzofuran (DBF) or dibenzothiophene (DBT)) as a linker that has physicochemical properties for both holes and electrons. And, on both sides thereof, includes a nitrogen-containing aromatic ring (eg, pyridine, pyrazine, triazine), which is a type of fluorene which is an electron donor (EDG) and an azine group that is an electron attracting agent (EWG) with high electron absorption. By introducing an azine group, which is a functional group having a strong electron withdrawing ability (EWG), it is possible to improve the electron transfer speed and have more suitable physicochemical properties for electron injection and electron transport. When the compound of Formula 1 is applied as a material for the electron transport layer or the electron transport auxiliary layer, electrons can be well received from the cathode, and thus electrons can be smoothly transferred to the light emitting layer, thereby lowering the driving voltage of the device and improving efficiency and long life. Can be induced. As a result, the organic electroluminescent device can maximize the performance of the full color organic light emitting panel.

In addition, since the compound of Chemical Formula 1 is a bipolar compound, high recombination of holes and electrons can improve hole injection/transport capability, luminous efficiency, driving voltage, life characteristics, and durability. Also, the electron transport ability and the like can be improved depending on the type of the substituent to be introduced. Therefore, the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a light emitting layer material.

Furthermore, the compound represented by Chemical Formula 1 is not only very advantageous for electron transport, but also exhibits low driving voltage, high efficiency, and long life characteristics. The excellent electron transport ability of these compounds can have high efficiency and fast mobility in organic electroluminescent devices, and it is easy to control HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, it is possible to exhibit high electron transport properties in an organic electroluminescent device using such a compound.

On the other hand, the red and green light-emitting layers of the organic electroluminescent device use phosphorescent materials, respectively, and their technology maturity is high. On the other hand, the blue light emitting layer has a fluorescent material and a phosphorescent material, of which the fluorescent material needs to improve performance, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a great possibility of development, the technical difficulty is relatively high, and thus there is a limit to improve the performance (eg, driving voltage, efficiency, life, etc.) of the blue organic light emitting device having the same. Thus, in the present invention, the compound of Formula 1 may be applied as an electron transport layer (ETL) or electron transport auxiliary layer material in addition to the light emitting layer (EML). In this way, the material of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic electroluminescent device may be improved to improve the performance of the light emitting layer, specifically the blue light emitting layer and the organic electroluminescent device having the same. It has the advantage of being able to.

According to the present invention, the compound represented by Chemical Formula 1 has a fluorene and nitrogen-containing heteroaromatic ring (eg, azine) directly or a linker (L), respectively, on both sides thereof, centering on a 2,6-dibenzoic moiety. It has a basic skeletal structure that is connected through.

Since the 2,6-dibenzoic moiety (eg, Y-containing ring) is used as a linker connecting a fluorene group and a nitrogen-containing heteroaromatic ring, it is excellent in terms of high glass transition temperature (Tg) and thermal stability. Do. For one example of such a 2,6-dibenzoic moiety (eg, Y-containing ring), Y may be O, S, or Se, preferably O (dibenzofuran).

The fluorene group (X-containing ring) is directly connected to one phenyl group (eg, 2 digit) of the above-mentioned 2,6-dibenzoic moiety or through a linker (L). For one embodiment of such an X-containing ring, a plurality of Xs are the same as or different from each other, and may each independently be N or CR ₃ . Specifically, all of the plurality of X may be CR ₃ , or may include at least one nitrogen atom (N).

A plurality of R ₃ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl Boron group, C ₆ ~ C ₆₀ arylphosphinyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group in the group consisting of Alternatively, they may combine with adjacent groups (another R ₃ , or R ₁ to R ₂ ) to form a condensed ring. Specifically, a plurality of R ₃ are the same as or different from each other, each independently hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and a group consisting of a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from.

In addition, R ₁ and R ₂ included in the X-containing ring are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, or groups adjacent to them (eg, CR ₃₎ ) May be a condensed or fused monocyclic or polycyclic condensed ring. The X-containing ring may be a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, for example, 6 carbon atoms. It may be a monocyclic or polycyclic aromatic ring of 18 to 18, or a monocyclic or polycyclic heteroaromatic ring of 5 to 18 nuclear atoms.

For one embodiment of the present invention, the X-containing ring can be more specific to any one selected from the following structural formulae. However, it is not limited thereto.

In the above formula,

* Means a portion that is combined with the formula (1),

In addition, although not specifically indicated, at least one of the above-described structural formulas may be substituted with a substituent (eg, the same as the definition part of R ₃ ) known in the art.

The aforementioned X-containing ring (fluorene group) may be directly bound to a 2,6-dibenzoic moiety or may be bound through a separate linker (L). As described above, when a separate linker (L) is present between the fluorene group and the 2,6-dibenzoic moiety, the HOMO region is expanded to benefit the HOMO-LUMO distribution, and charge is appropriately overlaid by HOMO-LUMO. It is possible to increase the moving efficiency.

The linker (L) may be a conventional divalent group linker known in the art. Specifically, L may be a single bond (eg, a direct bond) or may be selected from the group consisting of an arylene group of C ₆ to C _{18 and} a heteroarylene group of 5 to 18 nuclear atoms. More specific examples of the arylene group and heteroarylene group include phenylene group, biphenylene group, naphthylene group, anthracenyl group, indylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, fury And an alkylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylylene group, and a pyrimidinylene group. For a preferred example of the L, L is a single bond or may be selected from the group consisting of C ₆ ~ C ₁₂ arylene group and a heteroarylene group having 5 to 12 nuclear atoms.

More specifically, L may be a single bond or a linking group selected from the following structural formula.

In the above formula,

* Means a portion that is combined with the formula (1),

In addition, although not shown in the above-mentioned structural formula, at least one or more substituents known in the art (eg, the same as the definition of R ₃ ) may be substituted.

In the compound represented by Formula 1 according to the present invention, a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom in the other phenyl group (eg, 6-position) of a 2,6-dibenzoic moiety (eg, azine, Z-containing heterocycle). For one embodiment of the nitrogen-containing heteroaromatic ring (eg, Z-containing ring), a plurality of Z are the same as or different from each other, and each independently N or CR ₄ , but at least one of the plurality of Z is N . For a preferred example, the plurality of Zs comprises 1 to 3 Ns. As such, by including a heterocycle containing at least one, preferably two to three nitrogens, it exhibits excellent electron absorption properties and is advantageous for electron injection and transport.

Here, R ₄ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ phosphine group, C ₁ ~ C ₄₀ phosphine oxide group and C ₆ ~ C ₆₀ arylamine group. Specifically, R ₄ is preferably selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and heteroaryl group having 5 to 60 nuclear atoms. Do.

In the Z-containing heterocycle according to the present invention, Ar ₁ and Ar ₂ may be substituted as various substituents.

Ar ₁ to Ar ₂ are the same or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, and a C ₃ to C ₄₀ cyclo. Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryl of C ₆ to C ₆₀ Oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl It may be selected from the group consisting of phosphine groups, C ₆ ~C ₆₀ arylphosphine oxide groups and C ₆ ~C ₆₀ arylamine groups. Specifically, Ar ₁ to Ar ₂ are each independently a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a nuclear number of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₆ ~ C ₆₀ It is preferably selected from aryl phosphine oxide groups and C ₆ ~ C ₆₀ arylamine groups, more preferably C ₆ ~ C ₆₀ aryl group and a heteroaryl of 5 to 60 nuclear atoms Group.

In the above formula (1), the arylene group and heteroarylene group of L, the alkyl group and aryl group of R ₁ to R _2, the alkyl group, alkenyl group, alkynyl group of R ₃ to R ₄ and Ar ₁ to Ar ₂ , Aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group, and arylamine group Each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ may be substituted with one or more substituents selected from the group consisting of arylamine groups, wherein when the plurality of substituents, they are the same as each other Or it may be different.

According to an embodiment of the present invention, the compound represented by Chemical Formula 1 may be more specifically embodied as any of the following Chemical Formulas 2 to 5. However, it is not limited thereto.

In Chemical Formulas 2 to 5,

X, Y, Z, L, R ₁ to R ₂ , Ar ₁ and Ar ₂ are as defined in Formula 1, respectively.

For a preferred example of the compound represented by any one of Formula 2 to Formula 5, a plurality of X are all CR ₃ or contain 1 to 2 N, R ₁ and R ₂ are each independently a methyl group, a phenyl group, or They may be condensed or fused monocyclic or polycyclic spiro rings.

In addition, Y may be O, and L may be a single bond, a phenylene or biphenylene group.

In addition, a plurality of Z are each independently N or CR ₄ , provided that 1 to 3 of the plurality of Z may include N, and Ar ₁ and Ar ₂ are each independently aryl groups and nuclei of C ₆ to C ₆₀ It may be selected from the group consisting of a heteroaryl group having 5 to 60 atoms.

When the 2,6-dibenzoic moiety introduced into the linker (L) according to the present invention is more specifically 2,6-dibenzofuran (Y = O), it is represented by any one of the following formulas 6 to 9 Can be.

In the above formulas 6 to 9,

X, Z, L, R ₁ to R ₂ , Ar ₁ and Ar ₂ are each as defined in Chemical Formula 1.

The compound represented by the formula (1) of the present invention described above may be more specifically as a compound exemplified below, for example, a compound represented by 1 to 270. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

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

In the present invention, "alkenyl (alkenyl)" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl (alkynyl)" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.

In the present invention, "aryl" 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. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and condensed form with an aryl group may also be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, and indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.

In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "arylamine" 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 the cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include morpholine and piperazine, but are not limited thereto.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 40 carbon atoms.

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

<Electronic transport layer material>

The present invention provides an electron transport layer comprising a compound represented by Formula 1 above.

The electron transport layer (ETL) serves to move electrons injected from the cathode to an adjacent layer, specifically, a light emitting layer.

The compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

The electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isooxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, and perylene ( perylene) compounds, aluminum complexes (e.g. Alq ₃ (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.

In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited, and may be appropriately adjusted within a range known in the art.

<Electron transport auxiliary layer material>

In addition, the present invention provides an electron transport auxiliary layer comprising the compound represented by Chemical Formula 1.

The electron transport auxiliary layer is disposed between the light emitting layer and the electron transport layer, and serves to prevent diffusion of excitons or holes generated in the light emitting layer into the electron transport layer. Accordingly, the electron transport auxiliary layer material has a high triplet energy and has an appropriate HOMO and LUMO level, so that a hole and electron balance material can be used.

The compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport auxiliary layer/electron transport layer material known in the art. It is preferably used alone.

As the electron transport auxiliary layer material that can be mixed with the compound of Formula 1, an electron transport layer material commonly known in the art can be used without limitation. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a heterocyclic derivative containing nitrogen, and the like.

In the present invention, when the compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited, and can be appropriately adjusted within a range known in the art.

<Organic electroluminescent device>

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Chemical Formula 1 according to the present invention.

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

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 Compounds. Specifically, the organic material layer containing the compound of Formula 1 is preferably a phosphorescent host material, an electron transport layer, or an electron transport material of the electron transport auxiliary layer of the light emitting layer.

According to an embodiment of the present invention, the organic electroluminescent device may be in the form of simultaneously comprising an electron transporting auxiliary layer comprising the compound of Formula 1 and an electron transporting layer comprising an electron transporting layer material known in the art. .

Meanwhile, the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, wherein the compound of Formula 1 may be included as a host material. In addition, the light emitting layer of the present invention may contain a compound known in the art as a host other than the compound of the formula (1).

When the compound represented by Chemical Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, or red, the bonding force between holes and electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Light emission efficiency and power efficiency), life, brightness and driving voltage can be improved. Specifically, the compound represented by Chemical Formula 1 is preferably included in an organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material. In particular, the compound represented by Chemical Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light emitting layer having high efficiency.

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 injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Formula 1, preferably a light emitting layer, more preferably a phosphorescent host It may include a compound represented by the formula (1). Meanwhile, an electron injection layer may be additionally 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 at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the above-described organic material layer contains the compound represented by Chemical Formula 1 above. have.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet may be used.

In addition, a positive electrode material known in the art can be used as the positive electrode material without limitation. Metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO ₂ :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 is not limited thereto.

Further, as the negative electrode material, a negative electrode material known in the art can be used without limitation. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF/Al or LiO2/Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, the present invention is not limited by the following examples.

 [Preparation Example 1] Synthesis of C1

<Step 1> Synthesis of 3'-bromo-5-chloro-2'-fluoro-[1,1'-biphenyl]-2-ol

(3-bromo-2-fluorophenyl)boronic acid (2.18 g, 10 mmol), 4-chloro-2-iodophenol (2.54 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 3'-bromo-5-chloro-2'-fluoro-[1,1'-biphenyl]-2-ol (2.11 g, yield 70% ).

1H-NMR: δ 7.20 (t, 1H), 7.65 (m, 2H), 7.80 (m, 3H), 8.98 (s, 1H)

<Step 2> Synthesis of 6-bromo-2-chlorodibenzo[b,d]furan

3'-bromo-5-chloro-2'-fluoro-[1,1'-biphenyl]-2-ol (3.01 g, 10 mmol), K ₂ CO ₃ (1.38 g, 10 mmol) in 50 ml of NMP Put and stirred at 140 ℃ for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and water was added to precipitate a solid. After filtering the precipitated solid, the desired compound 6-bromo-2-chlorodibenzo[b,d]furan (1.94 g, yield 69%) was obtained by column chromatography.

1H-NMR: δ 7.20 (m, 2H), 7.36 (d, 1H), 7.50 (m, 2H), 7.92 (d, 1H)

<Step 3> Synthesis of C1

6-bromo-2-chlorodibenzo[b,d]furan (2.81 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi( 1,3,2-dioxaborolane) (2.53 g, 10 mmol), Pd(dppf)Cl ₂ (0.73 g, 1 mmol), potassium acetate (2.94 g, 30 mmol) in 100 ml of 1,4-Dioxane 110 Stir at 8° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, and after removal of the solvent, C1 (2.23 g, yield 68%) as a target compound was obtained using column chromatography.

1H-NMR: δ 1.20 (s, 12H), 7.20 (d, 1H), 7.32 (t, 1H), 7.42 (d, 1H), 7.50 (m, 2H), 7.98 (d, 1H)

[Preparation Example 2] Synthesis of C2

2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C2 (2.90 g, yield 67%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 9H), 7.88 (d, 1H), 8.08 (d, 1H), 8.36 (m, 4H)

[Preparation Example 3] Synthesis of C3

2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C3 (3.36 g, yield 66%) was obtained using column chromatography.

1H-NMR: δ 7.25 (m, 3H), 7.50 (m, 9H), 7.75 (m, 2H), 7.88 (d, 1H), 7.96 (m, 2H), 8.08 (d, 1H), 8.36 (m , 2H)

[Preparation Example 4] Synthesis of C4

2-chloro-4,6-diphenylpyridine (2.65 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) ) Into 100 ml of THF/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C4 (2.80 g, yield 65%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 9H), 7.75 (m, 2H), 8.15 (m, 4H), 8.29 (m, 2H)

[Preparation Example 5] Synthesis of C5

2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (3.17 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C5 (3.09 g, yield 64%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 8H), 7.88 (d, 1H), 8.10 (m, 4H), 8.30 (m, 3H), 8.97 (d, 1H)

[Preparation Example 6] Synthesis of C6

2-chloro-4,6-diphenylpyrimidine (2.66 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) ) Into 100 ml of THF/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C6 (2.72 g, yield 63%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 9H), 7.90 (m, 5H), 8.10 (d, 1H), 8.23 (s, 1H)

[Preparation Example 7] Synthesis of C7

4-chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) ) Into 100 ml of THF/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C7 (2.68 g, yield 62%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 9H), 7.74 (d, 1H), 7.90 (m, 2H), 8.10 (d, 1H), 8.23 (s, 1H), 8.35 (m , 2H)

[Preparation Example 8] Synthesis of C8

4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g , 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C8 (3.10 g, yield 61%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 9H), 7.74 (m, 3H), 7.85 (m, 2H), 8.10 (d, 1H), 8.23 (s, 1H), 8.35 (m , 4H)

[Preparation Example 9] Synthesis of C9

4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine (3.43 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C9 (3.05 g, yield 60%) was obtained using column chromatography.

1H-NMR: δ 7.20 (m, 3H), 7.50 (m, 7H), 7.74 (d, 1H), 8.10 (d, 1H), 8.23 (s, 1H), 8.35 (m, 5H), 8.70 (d , 1H), 9.24 (s, 1H)

[Preparation Example 10] Synthesis of C10

2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd( PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C10 (3.09 g, yield 59%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.35 (m, 2H), 7.50 (m, 8H), 7.69 (d, 1H), 7.85 (m, 2H), 7.98 (d, 1H), 8.10 (d , 1H), 8.35 (m, 2H)

[Preparation Example 11] Synthesis of C11

2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd( PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C11 (3.03 g, yield 58%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.35 (m, 2H), 7.50 (m, 7H), 7.80 (m, 3H), 8.00 (m, 3H), 8.35 (m, 2H)

[Preparation Example 12] Synthesis of C12

2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd( PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C12 (2.98 g, yield 57%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.35 (m, 2H), 7.50 (m, 8H), 7.88 (m, 2H), 8.00 (m, 3H), 8.35 (m, 2H)

[Preparation Example 13] Synthesis of C13

2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (3.83 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C13 (3.08 g, yield 56%) was obtained using column chromatography.

1H-NMR: δ 1.69 (s, 6H), 7.30 (m, 3H), 7.50 (m, 7H), 7.78 (d, 1H), 7.88 (m, 3H), 8.05 (m, 2H), 8.35 (m , 2H)

[Preparation Example 14] Synthesis of C14

2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine (3.73 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd( PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 25 ml of THF 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C14 (2.97 g, yield 55%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.50 (m, 8H), 7.90 (m, 3H), 8.05 (d, 1H), 8.20 (m, 2H), 8.35 (m, 2H), 8.45 (d , 1H)

[Preparation Example 15] Synthesis of C15

2-chloro-4,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (4.47 g, 10 mmol), C1 (3.28 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of THF/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound C15 (3.31 g, yield 54%) was obtained using column chromatography.

1H-NMR: δ 7.20 (d, 1H), 7.30 (m, 4H), 7.50 (m, 7H), 7.90 (m, 3H), 8.05 (m, 5H)

[Synthesis Example 1] Synthesis of Compound 16

C2 (4.33 g, 10 mmol), 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.20 g, 10 mmol) ), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 Put into ml and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, Compound 16 (3.13 g, yield 53%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 591

[Synthesis Example 2] Synthesis of Compound 92

C3 (5.09 g, 10 mmol), 2-(9,9-diphenyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.44 g, 10 mmol) ), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 Put into ml and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, Compound 92 (4.11 g, yield 52%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 591

[Synthesis Example 3] Synthesis of Compound 123

C4 (4.31 g, 10 mmol), 2-(9,9'-spirobi[fluoren]-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.42 g, 10 mmol) ), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 Put into ml and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 123 (3.63 g, yield 51%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 711

[Synthesis Example 4] Synthesis of Compound 184

C5 (4.83 g, 10 mmol), 4,4,5,5-tetramethyl-2-(9-methyl-9-phenyl-9H-fluoren-4-yl)-1,3,2-dioxaborolane (3.82 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 184 (3.51 g, yield 50%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 703

[Synthesis Example 5] Synthesis of Compound 186

C6 (4.32 g, 10 mmol), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile (3.45 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) with 1,4-Dioxane 100 ml/ Put into 25 ml of H ₂ O and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 186 (3.14 g, yield 51%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 615

[Synthesis Example 6] Synthesis of Compound 266

C7 (4.32 g, 10 mmol), 2-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.96 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) with 1,4-Dioxane 100 ml/ Put into 25 ml of H ₂ O and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, a compound 266 (3.46 g, yield 52%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 666

[Synthesis Example 7] Synthesis of Compound 267

C8 (5.09 g, 10 mmol), 2-(10,10-dimethyl-10H-spiro[anthracene-9,9'-fluoren]-2'-yl)-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (4.84 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1 ,4-Dioxane into 100 ml/H ₂ O 25 ml and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, compound 267 (4.40 g, yield 53%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 831

[Synthesis Example 8] Synthesis of Compound 268

C9 (5.09 g, 10 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-3'-yl)-1,3,2-dioxaborolane (4.58 g , 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) with 1,4-Dioxane 100 ml/H ₂ O 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, a compound 268 (4.35 g, yield 54%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 805

[Synthesis Example 9] Synthesis of Compound 269

C10 (5.23 g, 10 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-thioxanthen]-4-yl)-1,3,2-dioxaborolane (4.74 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 269 (4.59 g, yield 55%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 835

[Synthesis Example 10] Synthesis of Compound 270

C11 (5.23 g, 10 mmol), 10-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-10H-spiro[acridine-9,9' -fluorene] (5.33 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4 -Dioxane 100 ml / H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, a compound 270 (5.01 g, yield 56%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 895

[Synthesis Example 11] Synthesis of Compound 219

C12 (5.23 g, 10 mmol), 4,4,5,5-tetramethyl-2-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,2-dioxaborolane (4.44 g , 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) with 1,4-Dioxane 100 ml/H ₂ O 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 219 (4.59 g, yield 57%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 805

[Synthesis Example 12] Synthesis of Compound 12

C13 (5.50 g, 10 mmol), 2-(9,9-dimethyl-9H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.20 g, 10 mmol) ), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 Put into ml and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 12 (4.10 g, yield 58%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 707

[Synthesis Example 13] Synthesis of Compound 221

C14 (5.40 g, 10 mmol), 2-(2-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 3.96 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) in 1,4-Dioxane 100 ml /H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 221 (4.56 g, yield 59%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 773

[Synthesis Example 14] Synthesis of Compound 227

C15 (5.40 g, 10 mmol), 2-(3-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 5.20 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) in 1,4-Dioxane 100 ml /H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 227 (5.83 g, yield 60%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 972

[Synthesis Example 15] Synthesis of Compound 233

C2 (4.33 g, 10 mmol), 2-(4-(9,9'-spirobi[fluoren]-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 5.18 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) in 1,4-Dioxane 100 ml /H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, Compound 233 (4.81 g, yield 61%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 789

[Synthesis Example 16] Synthesis of Compound 236

C8 (5.09 g, 10 mmol), 2-(4-(9,9-dimethyl-9H-fluoren-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3, 2-dioxaborolane (4.46 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) to 1,4 -Dioxane 100 ml / H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, a compound 236 (4.91 g, yield 62%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 792

[Synthesis Example 17] Synthesis of Compound 242

C10 (5.23 g, 10 mmol), 2-(4'-(9,9-diphenyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5 ,5-tetramethyl-1,3,2-dioxaborolane (5.96 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) was added to 25 ml of 1,4-Dioxane 100 ml/H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, a compound 242 (6.03 g, yield 63%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 958

[Synthesis Example 18] Synthesis of Compound 248

C11 (5.23 g, 10 mmol), 2-(9,9'-spirobi[fluoren]-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyridine (5.19 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4 -Dioxane 100 ml / H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 248 (5.63 g, yield 64%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 881

[Synthesis Example 19] Synthesis of Compound 41

C12 (5.23 g, 10 mmol), 2-(9,9-dimethyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.20 g, 10 mmol) ), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H ₂ O 25 Put in ml and stir at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, Compound 41 (4.43 g, yield 65%) was obtained using column chromatography.

Mass: [(M+H) ⁺ ]: 681

[Synthesis Example 20] Synthesis of Compound 57

C13 (5.50 g, 10 mmol), 5,5-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-indeno[1,2-b ]pyridine (3.21 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) 1,4- Dioxane 100 ml / H ₂ O into 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the compound 57 (4.67 g, yield 66%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 708

[Examples 1 to 20] Preparation of blue organic electroluminescent device

The compound synthesized in the above synthesis example was subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 Å was washed with distilled water. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone, or methanol, and then dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes. Then, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30nm)/ each compound in Table 2 (5 nm )/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) in order to prepare an organic electroluminescent device (see Table 1 below).

compound Thickness (nm) Hole injection layer DS-205 80 Hole transport layer NPB 15 Emitting layer ADN + 5% DS-405 30 Electron transport auxiliary layer Each compound in Table 2 5 Electron transport layer Alq ₃ 25 Electron injection layer LiF One cathode Al 200

[Comparative Example 1] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 16 was not used as the electron transport auxiliary layer material, and Alq ₃ as the electron transport layer material was deposited at 30 nm instead of 25 nm. .

[Comparative Example 2] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that C-1 was used instead of Compound 16 as the electron transport auxiliary layer material.

[Comparative Example 3] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that C-2 was used instead of Compound 16 as the electron transport auxiliary layer material.

For reference, the structures of NPB, AND, Alq _3, C-1 and C-2 used in Examples 1 to 20 and Comparative Examples 1 to 3 of the present application are as follows.

[Evaluation Example 1]

For the organic electroluminescent devices manufactured in Examples 1 to 20 and Comparative Example 1, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below.

Sample Electron transport layer Electron transport auxiliary layer Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd/A) Example 1 Alq ₃
(25nm) 16 4.5 453 7.6 Example 2 92 3.8 453 7.0 Example 3 123 4.6 453 7.5 Example 4 184 3.9 455 8.1 Example 5 186 4.0 452 7.2 Example 6 266 4.3 453 8.0 Example 7 267 4.6 454 7.5 Example 8 268 5.2 455 7.4 Example 9 269 5.0 454 7.1 Example 10 270 4.9 457 7.2 Example 11 219 4.8 458 7.1 Example 12 12 4.8 458 7.0 Example 13 221 4.6 454 6.8 Example 14 227 4.5 457 6.8 Example 15 233 4.6 456 6.7 Example 16 236 4.8 458 6.8 Example 17 242 4.9 457 6.8 Example 18 248 5.0 457 6.6 Example 19 41 5.1 454 6.5 Example 20 57 4.5 453 6.0 Comparative Example 1 Alq ₃
(30nm) - 5.5 458 5.5 Comparative Example 2 Alq ₃
(25nm) C-1 5.3 457 5.9 Comparative Example 3 C-2 5.4 457 5.6

As shown in Table 2 above, the blue organic electroluminescent devices of Examples 1 to 20 using the compound of the present invention as an electron transport auxiliary layer material were compared with the conventional Alq ₃ used for the electron transport layer without using the electron transport auxiliary layer. Compared to the blue organic light emitting device of Example 1, it was confirmed that it is superior in terms of driving voltage, emission peak, and current efficiency.

Claims (10)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
A plurality of Xs are the same as or different from each other, each independently N or CR ₃ ,
R ₁ and R ₂ are the same as or different from each other, and each independently selected from an alkyl group of C ₁ to C ₄₀ and an aryl group of C ₆ to C ₄₀ , or may combine with adjacent groups to form a condensed ring,
Y is O, S or Se,
L is a single bond or is selected from the group consisting of C ₆ to C ₁₈ arylene group and 5 to 18 heteroarylene group;
A plurality of Z is the same as or different from each other, each independently N or CR ₄ , provided that at least one of the plurality of Z is N,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, and a C ₃ to C ₄₀ cycloalkyl group. , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , arylox of C ₆ to C ₆₀ Period, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl force wave group, C ₆ ~ C ₆₀ aryl mono Phosphinicosuccinic group, C ₆ ~ C ₆₀ of the diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
R ₃ to R ₄ are the same as or different from each other, and each independently hydrogen, 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 ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Group consisting of aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group Or they may combine with adjacent groups to form a condensed ring;
The arylene group and heteroarylene group of L, the alkyl group and aryl group of R ₁ to R _2, the alkyl group of the R ₃ to R ₄ and Ar ₁ to Ar ₂ , alkenyl group, alkynyl group, aryl group, heteroaryl group , Aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, phosphine group, phosphine oxide group, and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ may be substituted by one substituent at least one selected from the group consisting of an aryl amine of the C _60, the case when the substituent is plural, they may be the same or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,
X, Y, Z, L, R ₁ to R ₂ , Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
The X-containing ring is any one compound selected from the following structural formula:

In the above formula,
* Means the part to be combined with the formula (1). According to claim 1,
The L is a single bond or a compound selected from the following structural formula.

In the above formula,
* Means the part to be combined with the formula (1). According to claim 1,
The Z-containing ring is a compound selected from the group of substituents represented by the following A-1 to A-5:

In the above formula,
* Means a portion that is combined with the formula (1),
R ₄ , Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently selected from the group consisting of an aryl group of C ₆ to C _{60 and} a heteroaryl group having 5 to 60 nuclear atoms,
The aryl groups and heteroaryl groups of Ar ₁ to Ar ₂ are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C Alkynyl group of ₂ to C ₄₀ , cycloalkyl group of C ₃ to C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ - an aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~ C ₆₀ aryl optionally substituted with 1 substituent at least one selected from the group consisting of amine groups of In this case, when the substituents are plural, they may be the same or different from each other. According to claim 1,
R ₃ to R ₄ are the same as or different from each other, and each independently selected from the group consisting of hydrogen, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group having 5 to 60 nuclear atoms. And
The alkyl group, aryl group and heteroaryl group of R ₃ to R ₄ are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, arylboronic group of _{C 6 ~ C 60, C 6} ~ C 60 of the aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and one substituent at least one selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of It may be substituted, wherein when the plurality of substituents, they may be the same as or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound that is an electron transport layer or an electron transport auxiliary layer material. An organic material comprising a positive electrode, a negative electrode, and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the organic material layers of the one or more layers comprises the compound according to any one of claims 1 to 8. EL device. The method of claim 9,
The organic material layer containing the compound is an organic electroluminescent device, characterized in that selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.