KR20200107339A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent electron transport and luminescence ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer. In the compound represented by chemical formula 1 of the present invention, a ring A is a monocyclic or polycyclic heterocycle containing at least one heteroatom.

Description

An organic compound and an organic electroluminescent device containing the same TECHNICAL FIELD [ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

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

From the observation of Bernanose's organic thin-film emission in the 1950s, a study on organic electroluminescent (EL) devices (hereinafter simply referred to as'organic EL devices') followed by blue electroluminescence using an anthracene single crystal in 1965 was conducted in 1987. An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer by (Tang) was presented. 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 material layer in the device, leading to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, 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, and the like according to their function.

The material for forming the light emitting layer of the organic EL device may be classified 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 to realize better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material can be classified 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. Development of such a phosphorescent material can theoretically improve the luminous efficiency of up to 4 times compared to fluorescence, and thus attention is being 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 transport 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 as light emitting materials. In particular, as phosphorescent materials that have a great advantage in terms of efficiency improvement among light-emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ and (acac)Ir(btp) ₂ are blue, green, and red dopant materials. Is being used. Until now, CBP has shown excellent properties as a phosphorescent host material.

However, the existing materials have an advantage in terms of light emission characteristics, but the glass transition temperature is low and the thermal stability is very poor, so that the lifespan of the organic EL device is not satisfactory.

An object of the present invention is to provide a novel compound that can be used as an organic material layer material of an organic electroluminescent device, specifically, a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material, etc., because it has excellent electron injection and transport ability, and luminescence ability. To do.

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

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

In Formula 1,

Ring A is a monocyclic or polycyclic heterocycle containing at least one heteroatom,

Y ₁ and Y ₂ are the same as or different from each other, and each independently C(R ₁ ) or N, wherein when R ₁ is plural, the plural R _1s are the same or different from each other;

R ₁ and R ₂ are 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 to C ₄₀ Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to 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 aryl phosphazene group, a C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, the group bonded to C ₆ ~ C ₆₀ of the diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or adjacent the Can form a condensed ring,

a is an integer from 0 to 4,

However, the ring in which the ring A and the N-containing ring are fused is a 5-5 membered fused heteroring or a 6-5 membered fused heterocycle containing at least 3 or more heteroatoms,

In the above R ₁ and R ₂ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphanyl group, monoarylphosfinyl group, diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group of, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl A boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphanyl group, a C ₆ ~ C ₆₀ monoarylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and C ₆ It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group of ~C ₆₀ , and in this case, when substituted with a plurality of substituents, these 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 including the compound represented by Formula 1 above.

In addition, the present invention includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer is an organic electric field including the compound represented by the above-described formula (1). It provides a light emitting device.

Here, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of an emission layer, a light emission 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 Formula 1 according to the present invention not only has a novel structure, but also has excellent electron transport and luminescence capabilities, it can be used as an organic material layer material of 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, compared to conventional host material or electron transport material, high thermal stability, low driving voltage, fast mobility, high current efficiency And an organic electroluminescent device having a long lifespan, and further, it can be effectively applied to a full-color display panel with improved performance and lifespan.

The effects according to the present invention are not limited by the contents exemplified above, and more various effects are included in the present specification.

Hereinafter, the present invention will be described in detail.

<New organic compounds>

According to the present invention, the compound represented by Formula 1 has a fused heterocyclic core to which heterocyclic groups containing at least one heteroatom (eg, N, O, S, etc.) are bonded, This core has a new structure in which various substituents are substituted.

As such, the compound having the structure of Formula 1 condenses a triazine structure to have similar properties to the triazolopyridine compound (TAP), and is electrochemically stable, and the glass transition temperature (Tg) of the compound is It can increase significantly and further increase the thermal stability. Accordingly, it is possible to improve the long life characteristics of the organic electroluminescent device including the above compound.

In addition, the compound of Formula 1 not only contains a nitrogen-containing aromatic ring (e.g., triazine, imidazole, etc.), which is a kind of azine group, which is an electron attracting group (EWG) having high electron absorption, in the core structure, as well as a plurality of heterogeneous heterogeneous groups. The aromatic rings are bonded to form a fused bi-azine-based structure. As described above, a plurality of azine groups, which are functional groups having strong electron attraction ability (EWG), are introduced, thereby improving the electron transport speed, thereby enabling physicochemical properties more suitable 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 high efficiency and long life. You can induce. As a result, the organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

In particular, the compound of Formula 1 according to the present invention has a triplet (T1) energy and electron transport property by synthesizing a new structure condensed with triazine or oxadiazole, which is an example of an electron withdrawing group (EWG) having high electron absorption. It can be adjusted and used as a new EWG material.

Furthermore, the compound represented by Formula 1 is not only very advantageous for electron transport, but also exhibits low driving voltage, high efficiency, and long life. The excellent electron transport ability of these compounds can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to adjust the 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.

Meanwhile, the red and green emission layers of organic electroluminescent devices each use phosphorescent materials, and their technology maturity is high. In contrast, the blue light-emitting layer includes a fluorescent material and a phosphorescent material, of which the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, while the blue light emitting layer has a high possibility of development, the technical difficulty is relatively high, so there is a limit to improving the performance (eg, driving voltage, efficiency, life, etc.) of the blue organic light emitting device having the blue light emitting layer. Accordingly, in the present invention, the compound of Formula 1 may be applied as an electron transport layer (ETL) or an electron transport auxiliary layer material in addition to the light emitting layer (EML). In this way, by changing the material of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic EL device, the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic EL device having the same can be improved. There is an advantage that you can.

According to the present invention, the compound represented by Formula 1 is a heterocyclic group containing at least one heteroatom (e.g., N, O, S, etc.), specifically a fusion of rings A and N-containing rings. It has a heterocyclic core, and has a structure in which various substituents are substituted on this core.

Here, the heterocyclic core in which the ring A and the N-containing ring are fused is a 5-5 membered fused heterocycle containing at least 3 or more heteroatoms, or 6-5 membered ) It may be a fused heterocycle.

In Formula 1, ring A contains at least one heteroatom, and may be a conventional monocyclic or polycyclic heterocycle known in the art. For a specific example, ring A may be a 5- or 6-membered heteroalicyclic ring or a heteroaromatic ring, wherein the heteroatom may be at least one selected from N, O, and S. For a preferred example of the 6-membered ring A, it may be a nitrogen-containing 6-membered heterocycle containing 1 to 2 N. In addition, for a preferred example of the 5-membered ring A, it may be a 5-membered heterocyclic ring including O or S, or a 5-membered heterocycle including one of O or S and N.

R ₂ contained in the ring A is not particularly limited, and hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky Nyl 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 alkyl jade 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 aryl phosphazene group, C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, C ₆ ~ diaryl phosphine of C ₆₀ blood group and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or, it may be combined with adjacent groups (eg, R ₂ ) to form a condensed ring. At this time, the number (eg, a) of R ₂ introduced into ring A may be an integer of 0 to 4. For example, when a is 0, R ₂ may be hydrogen. In addition, when a is greater than 0 and less than or equal to 4, a plurality of R ₂ may be the same as or different from each other, and each independently may be the remaining substituents excluding hydrogen in the definition of R ₂ .

In the N-containing ring according to the present invention, Y ₁ and Y ₂ are the same as or different from each other, and each independently C(R ₁ ) or N. In this case, when R ₁ is plural, the plurality of R ₁ is 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 to C ₄₀ alkynyl group, 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, C ₁ ~ C ₄₀ alkyloxy 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 arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosfinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group of, or adjacent R ₁ may be bonded to each other to form a condensed ring.

For a specific example, a plurality of R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a 5 to 60 nuclear atom hetero It is preferable to form a condensed ring by being selected from the group consisting of aryl groups, or by bonding adjacent R _1s . Here, the alkyl group, aryl group, and heteroaryl group of R ₁ and R ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, number of nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylphosphanyl groups, C ₆ to C ₆₀ monoarylphosfinyl groups or substituted with one or more substituents selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl group of the diaryl phosphine blood group and C ₆ ~ C _60, or may be unsubstituted.

According to the present invention, the compound represented by Formula 1 includes a 6-5 membered fused hetero ring or a 5-5 membered fused hetero ring formed by bonding of heterocyclic groups as a core structure.

According to an embodiment of the present invention, a compound having a 6 to 5 membered fused hetero ring may be represented by any one of the following Chemical Formulas 2 and 3.

In Formula 2 or 3,

Y ₁ and Y ₂ are each the same as defined in Formula 1.

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C(R ₃ ). However, at least one of Z ₁ to Z ₅ is N. It preferably contains 1 or 2 N, more preferably 2 N.

Here, when R ₃ is plural, 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 alke Nyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ to C ₄₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ arylboronic a C ₄₀ group, C ₆ ~ C ₄₀ aryl phosphine group, 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 an adjacent It can be combined with a group to form a condensed ring. Specifically, a plurality of R ₃ are the same or different from each other, and each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, or a 5 to 40 nuclear atom heteroaryl group is preferred .

Ring B may be a conventional hydrocarbon-based or a hydrocarbon-based ring containing one or more heteroatoms known in the art, and they are condensed, fused, bridged, or spirocyclic with other adjacent rings (eg, core structure). It can be in the form. For example, ring B 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, and specifically, 6 carbon atoms It may be a monocyclic or polycyclic aromatic ring of to 18, or a monocyclic or polycyclic heteroaromatic ring of 5 to 18 nuclear atoms. For one embodiment of the present invention, ring B is preferably a C ₆ ~ C ₁₈ aromatic ring, or a heteroaromatic ring having 5 to 18 nuclear atoms.

R ₄ contained in the ring B is not particularly limited, and 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 alky Nyl 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 alkyl jade 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 aryl phosphazene group, C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, C ₆ ~ diaryl phosphine of C ₆₀ blood group and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or, it may form a condensed ring by bonding with adjacent groups (eg, R ₄ ). At this time, the number of R ₄ introduced into the ring B (eg, b) may be an integer of 0 to 4. For example, when b is 0, R ₄ may be hydrogen. In addition, when b is greater than 0 and less than or equal to ₄ , a plurality of R ₄ may be the same as or different from each other, and each independently may be the remaining substituents excluding hydrogen in the definition of R ₄ .

According to an embodiment of the present invention, the compound represented by Chemical Formula 2 may be further specified in any one of the following Chemical Formulas 2a to 2e. However, it is not limited thereto.

[Formula 2a]

[Formula 2b]

[Formula 2c]

[Formula 2d]

[Formula 2e]

According to another embodiment of the present invention, the compound represented by Formula 3 may be more embodied in any one of Formulas 3a to 3j below. However, it is not limited thereto.

[Formula 3a]

[Formula 3b]

[Formula 3c]

[Formula 3d]

[Formula 3e]

[Chemical Formula 3f]

[Chemical Formula 3g]

[Chemical Formula 3h]

[Formula 3i]

[Formula 3j]

In Formulas 2a to 3j,

Y ₁ , Y ₂ , R ₄ , and b are each the same as defined in claim 4. For a specific example, the chemical structure represented by Formula 3a described above may be preferable.

In addition, although not specifically indicated in the above structural formulas, the heteroaromatic ring into which R ₄ is introduced is a heteroaromatic ring having 5 to 18 nuclear atoms containing at least one hetero atom, and specifically containing 1 to 3 N It may be a nitrogen-containing heteroaromatic ring. At this time, the introduction position of the hetero atom is not particularly limited to the above structural formula, and may be introduced at various positions.

Ar ₁ and Ar ₂ 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 Of an alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy 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 aryl phosphazene group, a C ₆ ~ C ₆₀ monoaryl Phosphinicosuccinic group, diaryl phosphine of C ₆ ~ C ₆₀ blood group and a C ₆ ~ C ₆₀ group consisting of an aryl amine of the Is selected from;

In the above Ar ₁ and Ar ₂ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphanyl group, monoarylphosfinyl group, diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group of, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl A boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphanyl group, a C ₆ ~ C ₆₀ monoarylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and C ₆ It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group of ~C ₆₀ , and in this case, when substituted with a plurality of substituents, these may be the same or different from each other.

For a preferred example of the compound represented by any one of Formulas 2a to 3e, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently C ₆ ~ C ₆₀ aryl group or 5 to 60 nuclear atoms It is a heteroaryl group,

R ₄ is selected from the group consisting of hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,

The aryl and heteroaryl groups of Ar ₁ and Ar ₂ , the alkyl group, aryl group, and heteroaryl group of R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ - substituted with C ₆₀ or monoaryl Phosphinicosuccinic group or a C ₆ ~ C ₆₀ of diaryl phosphine group and a C ₆ ~ blood selected from the group consisting of aryl silyl C 1 ₆₀ kinds of substituents or may be unsubstituted.

Meanwhile, according to another embodiment of the present invention, a compound having a 5 to 5 membered fused hetero ring may be represented by any one of Formulas 4 to 7 below.

In Chemical Formulas 4 to 7,

Y ₁ and Y ₂ are the same as defined in Formula 1, and rings B, R ₄ and b are the same as defined in Formula 3,

X is O or S.

Y ₃ and Y ₄ are the same as or different from each other, and each independently C(R ₅ ) or N. In this case, when R ₅ is plural, a plurality of R ₅ 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 ₆ ~ C ₄₀ aryl group, nuclear atom number 5 ~ 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ to C ₄₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C group _{of 6} to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide group, and a C ₆ to C ₄₀ selected from the group consisting of aryl silyl, or of, or adjacent groups of It can be combined with (eg, R ₅ ) to form a condensed ring.

For a specific example, a plurality of R ₅ are the same as or different from each other, and each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms It is selected from the group, or it is preferable to combine adjacent R ₅ to form a condensed ring. Here, the alkyl group, aryl group, and heteroaryl group of R ₅ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, and 5 to 60 nuclear atoms Heteroaryl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosfinyl group or C ₆ - substituted from the group consisting of C ₆₀ diallyl Phosphinicosuccinic group and a C ₆ ~ C ₆₀ aryl silyl group of 1 or more substituents selected, or may be unsubstituted.

According to an embodiment of the present invention, the compound represented by Formula 4 may be further specified by the following Formula 4a or Formula 4b. However, it is not limited thereto.

[Formula 4a]

[Formula 4b]

According to an embodiment of the present invention, the compound represented by Chemical Formula 5 may be further specified by Chemical Formula 5a or Chemical Formula 5b. However, it is not limited thereto.

[Formula 5a]

[Formula 5b]

According to an embodiment of the present invention, the compound represented by Formula 6 may be further specified by Formula 6a or 6b below. However, it is not limited thereto.

[Formula 6a]

[Formula 6b]

According to an embodiment of the present invention, the compound represented by Chemical Formula 7 may be further specified by the following Chemical Formula 7a or 7b. However, it is not limited thereto.

[Formula 7a]

[Formula 7b]

In Formulas 4a to 7b,

X, Y ₃ , Y ₄ , R ₄ and b are each the same as defined in Formulas 4 to 7. For a specific example, the chemical structure represented by Formula 6a (wherein X is O, Y ₃ is C(R ₅ ), R ₅ is hydrogen, and Y ₄ is N) may be preferred.

In addition, although not specifically shown in the above structural formula, the heteroaromatic ring into which R ₄ is introduced is a heteroaromatic ring having 5 to 18 nuclear atoms containing at least one hetero atom, and specifically containing 1 to 3 N It may be a nitrogen heteroaromatic ring. At this time, the introduction position of the hetero atom is not particularly limited to the above structural formula, and may be introduced at various positions.

For a preferred example of the compound represented by any one of Formulas 4a to 7a, X is O or S, Y ₃ and Y ₄ are the same as or different from each other, and each independently C (R ₅ ) or N, In this case, when R ₅ is plural, the plurality of R ₅ are the same or different from each other, and each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl having 5 to 60 nuclear atoms It is preferable to form a condensed ring by being selected from the group consisting of groups, or by combining adjacent R _5s ,

R ₄ is selected from the group consisting of hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,

The alkyl group, aryl group, and heteroaryl group of R ₄ and R ₅ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of monoaryl Phosphinicosuccinic group or substituted by one or more substituent species selected from the group C ₆ ~ C ₆₀ diallyl Phosphinicosuccinic group and a C ₆ ~ C ₆₀ aryl group consisting of silyl, or may be unsubstituted.

Meanwhile, the aforementioned Chemical Formulas 2a to 3j; Formulas 4 to 7; And in the compound represented by any one of Formulas 4a to 7b, at least one of Ar ₁ , Ar ₂ , R ₄ and R ₅ may have a substituent represented by Formula 8 below.

In the above formula,

* Means a part bonded to the corresponding formula.

L may be a conventional linker of a conventional divalent group known in the art. For example, L may be a single bond (eg, direct bond), or may be selected from the group consisting of an arylene group of C ₆ ~ C _{18 and} a heteroarylene group having 5 to 18 nuclear atoms. Specific examples of such L include phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl And a ene group, a pyrroleylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, and a pyrimidinylene group. More specifically, it is preferable that L is a single bond, a phenylene group, a biphenylene group, or a carbazolyl group.

For one embodiment of the present invention, L may be a single bond or a linker selected from the following structures.

In the above formula, * means a portion in which a bond is formed.

Here, when L is a fluorene-based linker, two of the three * can be freely selected as the bonding site.

R ₆ is an aryl group of C ₆ to C ₆₀ or a heteroaryl group having 5 to 60 nuclear atoms, and the aryl group and heteroaryl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ Alkyl group of, C ₆ to C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, arylamine group of C ₆ to C ₆₀ , alkylsilyl group of C ₁ to C ₄₀ , aryl of C ₆ to C ₆₀ It may be substituted with one or more substituents selected from the group consisting of a phosphanyl group, a C ₆ ~ C ₆₀ monoarylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and a C ₆ ~ C ₆₀ arylsilyl group. .

The compound represented by Formula 1 of the present invention described above may be further embodied as a compound illustrated below, for example, a compound represented by 1 to 150. However, the compound represented by Formula 1 of the present invention is not limited by those illustrated below.

In the present invention, "alkyl" refers to 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, hexyl, and the like.

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

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

In the present invention, "aryl" refers to 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 phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring 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, fused or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as 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-, and R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is 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 the 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" refers to an amine substituted with an aryl having 6 to 40 carbon atoms.

In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such 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, but are not limited to, morpholine and piperazine.

In the present invention, "alkylsilyl" is 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.

<Electron transport layer material>

The present invention provides an electron transport layer comprising the compound represented by Chemical Formula 1.

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 electron transport materials that can be used include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylenes ( perylene) compounds, aluminum complexes (e.g. Alq ₃ (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq) There are '2OAc, 2(Gaq'2)), etc. These can be used alone or two or more types can be used in combination.

In the present invention, when the compound of Formula 1 and the material for the electron transport layer 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 auxiliary electron transport layer comprising the compound represented by the 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.

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 layer material known in the art. It is preferably used alone.

The electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. 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 material for the electron transport auxiliary layer are mixed, the mixing ratio thereof is not particularly limited, and may be appropriately adjusted within a range known in the art.

<Organic EL device>

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) including the compound represented by 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 It includes a compound represented by Formula 1. In this case, the compounds 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, an emission layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 above. Contains compounds. Specifically, the organic material layer including the compound of Formula 1 is preferably a phosphorescent host material for the light emitting layer, an electron transport layer, or an electron transport material for an electron transport auxiliary layer.

The emission layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and in this case, the compound of Formula 1 may be included as a host material. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

When the compound represented by Formula 1 is included as a material for an emission layer of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, and red, the binding force between holes and electrons in the emission layer increases, so 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 Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Formula 1 of the present invention is 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 have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. At this time, 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 May include the compound represented by Formula 1 above. 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 an interface between an electrode and an organic material layer.

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

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 method.

The substrate used in the manufacture of 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, and the like may be used.

In addition, as the cathode material, a cathode material known in the art may be used without limitation. For example, 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); Combinations of metals and oxides 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.

In addition, as the negative electrode material, a negative electrode material known in the art may be used without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multi-layered material such as LiF/Al or LiO2/Al, but is not limited thereto.

Further, 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 may be used without limitation.

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

[Preparation Example 1] Synthesis of C-1

<Step 1> Synthesis of N-(1H-benzo[d]imidazol-2-yl)benzimidamide

1H-benzo[d]imidazol-2-amine (1.33 g, 10 mmol), benzonitrile (1.03 g, 10 mmol), and anhydrous tin tetrachloride (7.8 g, 30 mmol) were added to 100 ml of Toluene under an argon stream at 130℃. Stir for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent in the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(1H-benzo[d]imidazol-2-yl)benzimidamide (1.41 g, yield 60%) was obtained by column chromatography.

<Step 2> Synthesis of C-1

N-(1H-benzo[d]imidazol-2-yl)benzimidamide (2.36 g, 10 mmol), 4-bromobenzaldehyde (5.55 g, 30 mmol) was added to 100 ml of Toluene, stirred at 110° C. for 1 hour, and then CuI (0.19 g, 1 mmol), N,N-dimethylglycine (0.21 g, 2 mmol) was added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. After cooling to room temperature, extraction with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , Na ₂ SO ₄ was added to the organic layer, filtered and concentrated, and then the target compound C-1 (2.36 g, using column chromatography) Yield 59%) was obtained.

[Preparation Example 2] Synthesis of C-2

<Step 1> Synthesis of N-(5-bromo-1H-benzo[d]imidazol-2-yl)benzimidamide

5-bromo-1H-benzo[d]imidazol-2-amine (2.12 g, 10 mmol), benzonitrile (1.03 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) was added to 100 ml of Toluene under an argon stream. And stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent of the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(5-bromo-1H-benzo[d]imidazol-2-yl)benzimidamide (1.82 g, yield 58%) was obtained by column chromatography.

<Step 2> Synthesis of C-2

N-(5-bromo-1H-benzo[d]imidazol-2-yl)benzimidamide (3.15 g, 10 mmol) and benzaldehyde (3.18 g, 30 mmol) were added to 100 ml of Toluene and stirred at 110° C. for 1 hour. Then CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to perform the target compound C-2 (2.28 g, yield) 57%).

[Preparation Example 3] Synthesis of C-3

<Step 1> Synthesis of N-(2-bromophenyl)-4-chloro-6-phenyl-1,3,5-triazin-2-amine

2,4-dichloro-6-phenyl-1,3,5-triazine (2.26 g, 10 mmol), 2-bromoaniline (1.72 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P (t-Bu) ₃ (0.4 g, 2 mmol) and NaOt-Bu (1.9 g, 20 mmol) were added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, the target compound, N-(2-bromophenyl)-4-chloro-6-phenyl-1,3,5-triazin-2-amine (2.02 g, yield 56) was used by column chromatography. %).

<Step 2> Synthesis of C-3

N-(2-bromophenyl)-4-chloro-6-phenyl-1,3,5-triazin-2-amine (3.61 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and the target compound, C-3 (0.84 g, yield 30%) was obtained by column chromatography.

[Preparation Example 4] Synthesis of C-4

N-(2-bromophenyl)-4-chloro-6-phenyl-1,3,5-triazin-2-amine (3.61 g, 10 mmol) synthesized in <Step 1> of [Preparation Example 3], Pd( PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After the reaction was completed, the organic layer was concentrated, and the target compound C-4 (0.42 g, yield 15%) was obtained by column chromatography.

[Preparation Example 5] Synthesis of C-5

<Step 1> Synthesis of N-(3-bromo-1H-1,2,4-triazol-5-yl)benzimidamide

3-bromo-1H-1,2,4-triazol-5-amine (1.62 g, 10 mmol), benzonitrile (1.03 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) was added to Toluene 100 under an argon stream. ml and stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent in the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(3-bromo-1H-1,2,4-triazol-5-yl)benzimidamide (1.46 g, yield 55%) was prepared by column chromatography. Got it.

<Step 2> Synthesis of C-5

N-(3-bromo-1H-1,2,4-triazol-5-yl)benzimidamide (2.66 g, 10 mmol), benzaldehyde (3.18 g, 30 mmol) was added to 100 ml of Toluene for 1 hour at 110°C. After stirring, CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to perform the target compound C-5 (1.90 g, yield) 54%).

[Preparation Example 6] Synthesis of C-6

<Step 1> Synthesis of N-(1H-benzo[d]imidazol-2-yl)-8-chlorodibenzo[b,d]furan-3-carboximidamide

1H-benzo[d]imidazol-2-amine (1.33 g, 10 mmol), 8-chlorodibenzo[b,d]furan-3-carbonitrile (2.27 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, in an argon stream) 30 mmol) was added to 100 ml of Toluene and stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent of the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(1H-benzo[d]imidazol-2-yl)-8-chlorodibenzo[b,d]furan-3-carboximidamide (1.91) was used by column chromatography. g, yield 53%) was obtained.

<Step 2> Synthesis of C-6

N-(1H-benzo[d]imidazol-2-yl)-8-chlorodibenzo[b,d]furan-3-carboximidamide (3.60 g, 10 mmol), benzaldehyde (3.18 g, 30 mmol) in 100 ml of Toluene After the mixture was stirred at 110° C. for 1 hour, CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to obtain the target compound C-6 (2.32 g, yield 52%).

[Preparation Example 7] Synthesis of C-7

<Step 1> Synthesis of N-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)nicotinimidamide

6-bromo-1H-imidazo[4,5-b]pyridin-2-amine (2.13 g, 10 mmol), nicotinonitrile (1.04 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) in an argon stream Put in 100 ml of Toluene and stirred at 130 ℃ for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent of the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)nicotinimidamide (1.61 g, yield 51%) using column chromatography. ).

<Step 2> Synthesis of C-7

Add N-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)nicotinimidamide (3.17 g, 10 mmol) and furan-2-carbaldehyde (2.88 g, 30 mmol) in 100 ml of Toluene. After stirring at 110° C. for 1 hour, CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to perform the target compound C-7 (1.96 g, yield) 50%).

[Preparation Example 8] Synthesis of C-8

<Step 1> Synthesis of N-(3H-imidazo[4,5-b]pyridin-2-yl)-2-naphthimidamide

3H-imidazo[4,5-b]pyridin-2-amine (1.34 g, 10 mmol), 2-naphthonitrile (1.53 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) was added to Toluene 100 under an argon stream. ml and stirred for 24 hours at 130°C. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent in the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(3H-imidazo[4,5-b]pyridin-2-yl)-2-naphthimidamide (1.40 g, yield 49%), was used by column chromatography. Got it.

<Step 2> Synthesis of C-8

Add N-(3H-imidazo[4,5-b]pyridin-2-yl)-2-naphthimidamide (2.87 g, 10 mmol), 3,5-dichlorobenzaldehyde (5.25 g, 30 mmol) in 100 ml of Toluene and 110 After stirring at °C for 1 hour, CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to determine the target compound C-8 (2.12 g, yield). 48%).

[Preparation Example 9] Synthesis of C-9

<Step 1> Synthesis of N-(5-chloro-4H-1,2,4-triazol-3-yl)-[1,1'-biphenyl]-4-carboximidamide

5-chloro-4H-1,2,4-triazol-3-amine (1.18 g, 10 mmol), [1,1'-biphenyl]-4-carbonitrile (1.79 g, 10 mmol), anhydrous tin under an argon stream Tetrachloride (7.8 g, 30 mmol) was added to 100 ml of Toluene and stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. After distilling the solvent in the filtered organic layer under reduced pressure, the target compound, N-(5-chloro-4H-1,2,4-triazol-3-yl)-[1,1'-biphenyl]-, was used by column chromatography. 4-carboximidamide (1.39 g, yield 49%) was obtained.

<Step 2> Synthesis of C-9

N-(5-chloro-4H-1,2,4-triazol-3-yl)-[1,1'-biphenyl]-4-carboximidamide (2.97 g, 10 mmol), picolinaldehyde (3.21 g, 30 mmol) Was added to 100 ml of Toluene, stirred at 110° C. for 1 hour, and then CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to obtain the target compound C-9 (1.77 g, yield) 46%).

[Preparation Example 10] Synthesis of C-10

<Step 1> Synthesis of N-(2-bromophenyl)-5-(3-chlorophenyl)-1,3,4-oxadiazol-2-amine

2-bromo-5-(3-chlorophenyl)-1,3,4-oxadiazole (2.59 g, 10 mmol), 2-bromoaniline (1.72 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol) , P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, the target compound, N-(2-bromophenyl)-5-(3-chlorophenyl)-1,3,4-oxadiazol-2-amine (1.57 g, yield 45) was used by column chromatography. %).

<Step 2> Synthesis of C-10

N-(2-bromophenyl)-5-(3-chlorophenyl)-1,3,4-oxadiazol-2-amine (3.50 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and then the target compound, C-10 (1.18 g, yield 44%) was obtained by column chromatography.

[Preparation Example 11] Synthesis of C-11

<Step 1> Synthesis of N-(1-bromonaphthalen-2-yl)-5-chloroisoxazol-3-amine

3-bromo-5-chloroisoxazole (1.82 g, 10 mmol), 1-bromonaphthalen-2-amine (2.22 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol) and NaOt-Bu (1.9 g, 20 mmol) were added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, N-(1-bromonaphthalen-2-yl)-5-chloroisoxazol-3-amine (1.39 g, yield 43%) was obtained by column chromatography.

<Step 2> Synthesis of C-11

N-(1-bromonaphthalen-2-yl)-5-chloroisoxazol-3-amine (3.23 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) in 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and then the target compound, C-11 (1.01 g, yield 42%) was obtained by column chromatography.

[Preparation Example 12] Synthesis of C-12

<Step 1> Synthesis of N-(2,3-dibromophenyl)-5-phenyloxazol-2-amine

2-bromo-5-phenyloxazole (2.24 g, 10 mmol), 2,3-dibromoaniline (2.50 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, N-(2,3-dibromophenyl)-5-phenyloxazol-2-amine (1.61 g, yield 41%) was obtained by column chromatography.

<Step 2> Synthesis of C-12

N-(2,3-dibromophenyl)-5-phenyloxazol-2-amine (3.94 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) Was placed in 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After the reaction was completed, the organic layer was concentrated, and then the target compound C-12 (1.25 g, yield 40%) was obtained by column chromatography.

[Preparation Example 13] Synthesis of C-13

<Step 1> Synthesis of N-(2-bromo-5-chlorophenyl)-5,6-diphenyl-1,2,4-triazin-3-amine

5,6-diphenyl-1,2,4-triazin-3-amine (2.48 g, 10 mmol), 1-bromo-4-chloro-2-iodobenzene (3.17 g, 10 mmol), Pd(OAc) ₂ ( 0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol), and NaOt-Bu (1.9 g, 20 mmol) were added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, the target compound, N-(2-bromo-5-chlorophenyl)-5,6-diphenyl-1,2,4-triazin-3-amine (1.79 g, Yield 41%).

<Step 2> Synthesis of C-13

N-(2-bromo-5-chlorophenyl)-5,6-diphenyl-1,2,4-triazin-3-amine (4.37 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol) , K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and then the target compound, C-13 (0.78 g, yield 22%) was obtained by column chromatography.

[Preparation Example 14] Synthesis of C-14

[Preparation Example 13] N-(2-bromo-5-chlorophenyl)-5,6-diphenyl-1,2,4-triazin-3-amine (4.37 g, 10 mmol) obtained in <Step 1>, Pd( PPh3) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After the reaction was completed, the organic layer was concentrated, and the target compound, C-14 (0.82 g, yield 23%) was obtained by column chromatography.

[Preparation Example 15] Synthesis of C-15

<Step 1> Synthesis of N-(2,4-dibromophenyl)-3,6-diphenyl-1,2,4-triazin-5-amine

5-chloro-3,6-diphenyl-1,2,4-triazine (2.67 g, 10 mmol), 2,4-dibromoaniline (2.50 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol) , P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 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, N-(2,4-dibromophenyl)-3,6-diphenyl-1,2,4-triazin-5-amine (2.12 g, yield 44) was used by column chromatography. %).

<Step 2> Synthesis of C-15

N-(2,4-dibromophenyl)-3,6-diphenyl-1,2,4-triazin-5-amine (4.82 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and the target compound, C-15 (1.80 g, yield 45%) was obtained by column chromatography.

[Preparation Example 16] Synthesis of C-16

<Step 1> Synthesis of N-(2,4-dibromophenyl)-3,5-diphenyl-1,2,4-triazin-6-amine

6-chloro-3,5-diphenyl-1,2,4-triazine (2.67 g, 10 mmol), 2,4-dibromoaniline (2.50 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol) , P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, N-(2,4-dibromophenyl)-3,5-diphenyl-1,2,4-triazin-6-amine (2.21 g, yield 46) was used by column chromatography. %).

<Step 2> Synthesis of C-16

N-(2,4-dibromophenyl)-3,5-diphenyl-1,2,4-triazin-6-amine (4.82 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 75 ml of DMF and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and then the target compound C-16 (1.88 g, yield 47%) was obtained by column chromatography.

[Preparation Example 17] Synthesis of C-17

<Step 1> Synthesis of 3-bromo-N-(1H-naphtho[2,3-d]imidazol-2-yl)benzimidamide

1H-naphtho[2,3-d]imidazol-2-amine (1.83 g, 10 mmol), 3-bromobenzonitrile (1.82 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) was added to Toluene 100 under an argon stream. ml and stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent in the filtered organic layer was distilled under reduced pressure, and then the target compound, 3-bromo-N-(1H-naphtho[2,3-d]imidazol-2-yl)benzimidamide (1.75 g, yield 48%) was used by column chromatography. ).

<Step 2> Synthesis of C-17

3-bromo-N-(1H-naphtho[2,3-d]imidazol-2-yl)benzimidamide (3.65 g, 10 mmol), dibenzo[b,d]furan-4-carbaldehyde (5.88 g, 30 mmol) Was added to 100 ml of Toluene and stirred at 110° C. for 1 hour, and then CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to perform the target compound C-17 (2.65 g, yield) 49%).

[Preparation Example 18] Synthesis of C-18

<Step 1> Synthesis of 4-bromo-N-(6-chloro-1H-benzo[d]imidazol-2-yl)benzimidamide

6-chloro-1H-benzo[d]imidazol-2-amine (1.67 g, 10 mmol), 4-bromobenzonitrile (1.82 g, 10 mmol), anhydrous tin tetrachloride (7.8 g, 30 mmol) was added to Toluene 100 under an argon stream. ml and stirred at 130° C. for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. After distilling the solvent of the filtered organic layer under reduced pressure, the target compound, 4-bromo-N-(6-chloro-1H-benzo[d]imidazol-2-yl)benzimidamide (1.74 g, yield 50) was used by column chromatography. %).

<Step 2> Synthesis of C-18

4-bromo-N-(6-chloro-1H-benzo[d]imidazol-2-yl)benzimidamide (3.49 g, 10 mmol), [1,1'-biphenyl]-3-carbaldehyde (5.46 g, 30 mmol ) Was added to 100 ml of Toluene and stirred at 110° C. for 1 hour, and then CuI (0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract with 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to obtain the target compound C-18 (2.50 g, yield). 49%).

[Preparation Example 19] Synthesis of C-19

<Step 1> Synthesis of N-(4-bromo-1H-imidazol-2-yl)benzimidamide

Add 4-bromo-1H-imidazol-2-amine (1.61 g, 10 mmol), benzonitrile (1.03 g, 10 mmol), and anhydrous tin tetrachloride (7.8 g, 30 mmol) in 100 ml of Toluene under an argon stream at 130°C. Stir for 24 hours. After completion of the reaction, it was cooled to room temperature and ethyl acetate was added. After slowly pouring into a cold 20% NaOH solution, extraction was performed three times with ethyl acetate, Na ₂ SO ₄ was added and filtered. The solvent in the filtered organic layer was distilled under reduced pressure, and then the target compound, N-(4-bromo-1H-imidazol-2-yl)benzimidamide (1.27 g, yield 48%) was obtained by column chromatography.

<Step 2> Synthesis of C-19

N-(4-bromo-1H-imidazol-2-yl)benzimidamide (2.65 g, 10 mmol) and benzaldehyde (3.18 g, 30 mmol) were added to 100 ml of Toluene and stirred at 110° C. for 1 hour, and then CuI ( 0.19 g, 1 mmol) and N,N-dimethylglycine (0.21 g, 2 mmol) were added. After 1 hour, iodine (1.26 g, 5 mmol) was added and stirred for 4 hours. After the completion of the reaction was confirmed by TLC, DDQ (2.72 g, 12 mmol) was added and stirred for 1 hour. Cool to room temperature, extract using 5% Na ₂ SO ₃ and CH ₂ Cl ₂ , add Na ₂ SO ₄ to the organic layer, filter and concentrate, and then use column chromatography to perform the target compound C-19 (1.65 g, yield) 47%).

[Preparation Example 20] Synthesis of C-20

<Step 1> Synthesis of N-(2,3-dibromophenyl)isothiazol-3-amine

3-bromoisoxazole (1.64 g, 10 mmol), 2,3-dibromoaniline (2.50 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol) ), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 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, N-(2,3-dibromophenyl)isothiazol-3-amine (1.53 g, yield 46%) was obtained by column chromatography.

<Step 2> Synthesis of C-20

N-(2,3-dibromophenyl)isothiazol-3-amine (3.34 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.2 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) in DMF 75 ml and heated at 150° C. for 24 hours under a nitrogen stream. After completion of the reaction, the organic layer was concentrated, and the target compound, C-20 (1.13 g, yield 45%), was obtained by column chromatography.

[Synthesis Example 1] Synthesis of Compound 1

C-1 (3.43 g, 10 mmol), 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl)pyrimidine (5.10 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) to 1,4 -Dioxane 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 in the filtered organic layer, the target compound 1 (3.10 g, yield 44%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 704

[Synthesis Example 2] Synthesis of Compound 2

C-2 (4.01 g, 10 mmol), 2-(3-(dibenzo[b,d]furan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 3.70 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) in 1,4-Dioxane 100 ml/ H ₂ O 25 ml and 100°C It was stirred 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 in the filtered organic layer, the target compound 2 (2.42 g, yield 43%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 564

[Synthesis Example 3] Synthesis of Compound 3

C-3 (2.80 g, 10 mmol), 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole (3.32 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P (t-Bu) ₃ (0.4 g, 2 mmol) and NaOt-Bu (1.9 g, 20 mmol) were added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound 3 (2.42 g, yield 42%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 576

[Synthesis Example 4] Synthesis of Compound 4

C-4 (2.80 g, 10 mmol), 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4 ,5,5-tetramethyl-1,3,2-dioxaborolane (4.72 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) as 1, 4-Dioxane 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 in the filtered organic layer, the target compound 4 (2.42 g, yield 41%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 590

[Synthesis Example 5] Synthesis of Compound 5

C-5 (3.52 g, 10 mmol), 4,4,5,5-tetramethyl-2-(3-(triphenylen-2-yl)phenyl)-1,3,2-dioxaborolane (4.30 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 1,4-Dioxane 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 in the filtered organic layer, the target compound 5 (2.30 g, yield 40%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 575

[Synthesis Example 6] Synthesis of Compound 6

C-6 (4.46 g, 10 mmol), 9H-carbazole (1.67 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound 6 (2.36 g, yield 41%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 577

[Synthesis Example 7] Synthesis of Compound 7

C-7 (3.93 g, 10 mmol), diphenyl(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3 -yl)phosphine oxide (4.80 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) 1,4-Dioxane 100 ml/ H ₂ O Put into 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 in the filtered organic layer, the target compound 7 (2.80 g, yield 42%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 666

[Synthesis Example 8] Synthesis of Compound 8

C-8 (4.42 g, 10 mmol), 2-(benzo[b]naphtho[1,2-d]thiophen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.20 g, 20 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) into 1,4-Dioxane 100 Into 25 ml of 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, compound 8 (3.60 g, yield 43%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 838

[Synthesis Example 9] Synthesis of Compound 9

C-9 (3.84 g, 10 mmol), 2-(4-(dibenzo[b,e][1,4]dioxin-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3 ,2-dioxaborolane (3.86 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 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 in the filtered organic layer, compound 9 (2.67 g, yield 44%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 608

[Synthesis Example 10] Synthesis of Compound 10

C-10 (5.23 g, 10 mmol), 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)-[1, 1'-biphenyl]-4-carbonitrile (4.31 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 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 in the filtered organic layer, compound 10 (2.42 g, yield 45%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 538

[Synthesis Example 11] Synthesis of Compound 11

C-11 (2.42 g, 10 mmol), 10-(9H-carbazol-3-yl)-7-phenyl-7H-benzo[c]carbazole (4.58 g, 10 mmol), Pd(OAc) ₂ (0.22 g , 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound 11 (3.05 g, yield 46%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 664

[Synthesis Example 12] Synthesis of Compound 12

C-12 (3.13 g, 10 mmol), 2-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoxaline (4.08 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) in 1,4-Dioxane 100 ml/ H ₂ O 25 ml and at 100° C. for 8 hours While stirring. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound 12 (2.41 g, yield 47%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 514

[Synthesis Example 13] Synthesis of Compound 13

C-13 (3.56 g, 10 mmol), 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[ d]imidazole (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) 1,4 -Dioxane 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 13 (2.69 g, yield 48%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 560

[Synthesis Example 14] Synthesis of Compound 14

C-14 (3.56 g, 10 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (4.33 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/ Put into 25 ml of H ₂ O 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 14 (3.07 g, yield 49%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 627

[Synthesis Example 15] Synthesis of Compound 15

C-15 (4.01 g, 10 mmol), 2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (5.25 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) in 100 ml of 1,4-Dioxane/ 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 in the filtered organic layer, the target compound 15 (3.59 g, yield 50%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 719

[Synthesis Example 16] Synthesis of Compound 16

C-16 (4.01 g, 10 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1, 3,5-triazine (4.35 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) 1,4-Dioxane 100 ml/ H ₂ O Put into 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 in the filtered organic layer, the target compound 16 (3.21 g, yield 51%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 629

[Synthesis Example 17] Synthesis of Compound 17

C-17 (5.41 g, 10 mmol), 14H-benzo[c]benzo[4,5]thieno[2,3-a]carbazole (3.23 g, 10 mmol), Pd(OAc) ₂ (0.22 g, 1 mmol), P(t-Bu) ₃ (0.4 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Xylene and stirred at 140° C. for 12 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 17 (4.07 g, yield 52%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 783

[Synthesis Example 18] Synthesis of Compound 18

<Step 1> 4-([1,1'-biphenyl]-3-yl)-2-([1,1'-biphenyl]-4-yl)-7-chlorobenzo[4,5]imidazo[1, Synthesis of 2-a][1,3,5]triazine

C-18 (5.11 g, 10 mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (2.04 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 1,4-Dioxane 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 from the filtered organic layer, the target compound, 4-([1,1'-biphenyl]-3-yl)-2-([1,1'-biphenyl]-4-yl), was used by column chromatography. -7-chlorobenzo[4,5]imidazo[1,2-a][1,3,5]triazine (2.69 g, yield 53%) was obtained.

Mass: [(M+H) ⁺ ]: 509

<Step 2> Synthesis of 18

4-([1,1'-biphenyl]-3-yl)-2-([1,1'-biphenyl]-4-yl)-7-chlorobenzo[4,5]imidazo[1,2-a] [1,3,5]triazine (5.09 g, 10 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline (3.06 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 was put into 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 18 (3.52 g, yield 54%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 652

[Synthesis Example 19] Synthesis of Compound 19

C-19 (3.51 g, 10 mmol), 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (5.11 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 1,4-Dioxane 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 in the filtered organic layer, the target compound 19 (3.60 g, yield 55%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 655

[Synthesis Example 20] Synthesis of Compound 20

C-20 (2.53 g, 10 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (5.23 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 1,4-Dioxane 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, the target compound 20 (3.19 g, yield 56%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 569

[Examples 1 to 20] Fabrication of blue organic electroluminescent devices

After the compound synthesized in Synthesis Example was subjected to high-purity sublimation purification by a conventionally known method, a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with a thin film of 1500 Å in ITO (Indium tin oxide) was washed with ultrasonic distilled water. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30nm)/ electron transport layer material of Table 1 below ( 30 nm)/LiF (1 nm)/Al (200 nm) were sequentially stacked 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 layer Each compound in Table 1 30 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 Alq ₃ was used instead of Compound 1 as the electron transport layer material.

[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 J-2 was used instead of Compound 1 as the electron transport layer material.

For reference, the structures of NPB, ADN, Alq ₃ and compound J-2 used in Examples 1 to 20 and Comparative Examples 1 to 2 are as follows, respectively.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Examples 1 to 2, respectively, 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. Done.

Sample Electron transport layer
material Driving voltage
(V) Luminescence peak
(nm) Current efficiency
(cd/A) Example 1 One 4.5 453 7.5 Example 2 2 4.8 454 7.0 Example 3 3 4.7 453 7.6 Example 4 4 3.9 455 8.0 Example 5 5 4.2 452 7.4 Example 6 6 4.4 459 8.2 Example 7 7 4.8 454 6.5 Example 8 8 5.0 456 7.4 Example 9 9 5.0 454 6.1 Example 10 10 4.9 457 7.2 Example 11 11 4.8 458 7.3 Example 12 12 4.7 457 7.0 Example 13 13 4.6 454 6.8 Example 14 14 4.5 457 6.8 Example 15 15 4.4 456 7.3 Example 16 16 4.3 458 6.8 Example 17 17 4.9 457 6.7 Example 18 18 5.0 457 6.6 Example 19 19 5.1 454 6.4 Example 20 20 4.5 456 6.1 Comparative Example 1 Alq ₃ 5.4 458 5.5 Comparative Example 2 J-2 5.4 457 5.9

As shown in Table 2, the blue organic light emitting devices of Examples 1 to 20 using the compound of the present invention as an electron transport layer material include Comparative Example 1 in which Alq ₃ was used for the electron transport layer; And compared with the blue organic light-emitting device of Comparative Example 2 using an electron transport layer material having a similar structure, it was confirmed that the device was superior in terms of driving voltage, emission peak, and current efficiency.

Claims (15)

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

In Formula 1,
Ring A is a monocyclic or polycyclic heterocycle containing at least one heteroatom,
Y ₁ and Y ₂ are the same as or different from each other, and each independently C(R ₁ ) or N, wherein when R ₁ is plural, the plural R _1s are the same or different from each other;
R ₁ and R ₂ are 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 to C ₄₀ Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to 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 aryl phosphazene group, a C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, the group bonded to C ₆ ~ C ₆₀ of the diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or adjacent the Can form a condensed ring,
a is an integer from 0 to 4,
However, the ring in which the ring A and the N-containing ring are fused is a 5-5 membered fused heterocycle or a 6-5 membered fused heterocycle containing at least 3 or more heteroatoms,
In the above R ₁ and R ₂ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphanyl group, monoarylphosfinyl group, diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group of, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl A boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphanyl group, a C ₆ ~ C ₆₀ monoarylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and C ₆ It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group of ~C ₆₀ , and in this case, when substituted with a plurality of substituents, these may be the same or different from each other. The method of claim 1,
The ring A is a 5- or 6-membered heteroalicyclic ring or a heteroaromatic ring, and the heteroatom is at least one compound selected from N, O, and S. The method of claim 1,
The plurality of R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a group consisting of a heteroaryl group having 5 to 60 nuclear atoms It is selected from, or adjacent R ₁ can be combined to form a condensed ring,
The alkyl group, aryl group, and heteroaryl group of R ₁ and R ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of monoaryl Phosphinicosuccinic group or C ₆ ~ C ₆₀ diallyl Phosphinicosuccinic group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ or aryl silyl compounds unsubstituted in. The method of claim 1,
The 6-membered-5 membered fused hetero ring contained in Formula 1 is a compound represented by the following Formula 2 or 3:
[Formula 2]

[Formula 3]

In Formula 2 or 3,
Y ₁ and Y ₂ are each the same as defined in claim 1,
Z ₁ to Z ₅ are the same as or different from each other, each independently N or C (R ₃ ), provided that at least one of Z ₁ to Z ₅ is N, and in this case, when R ₃ is plural, a plurality of R ₃ is Are the same or different from each other;
Ring B is 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,
R ₃ and 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 of, C ₆ to C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ to C ₄₀ C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cyclo alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, aryl group of C ₆ ~ C ₄₀ boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, 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 group to form a condensed ring Can;
b is an integer from 0 to 4,
In the above R ₃ and R ₄ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group are each independently 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 ₆ to C ₄₀ aryl group, heteroaryl group with 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ may be substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ of, In this case, when the substituents are plural, they may be the same or different from each other. The method of claim 4,
The Z ₁ to Z ₅ is a compound containing 1 or 2 N. The method of claim 4,
The 6-membered-5 membered fused hetero ring is a compound selected from the group consisting of the following Formulas 2a to 3j:
[Formula 2a]

[Formula 2b]

[Formula 2c]

[Formula 2d]

[Formula 2e]

[Formula 3a]

[Formula 3b]

[Formula 3c]

[Formula 3d]

[Formula 3e]

[Chemical Formula 3f]

[Chemical Formula 3g]

[Chemical Formula 3h]

[Formula 3i]

[Formula 3j]

In Formulas 2a to 3j,
Y ₁ , Y ₂ , R ₄ , and b are each the same as defined in claim 4,
Ar ₁ and Ar ₂ 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 Of an alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy 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 aryl phosphazene group, a C ₆ ~ C ₆₀ monoaryl Phosphinicosuccinic group, diaryl phosphine of C ₆ ~ C ₆₀ blood group and a C ₆ ~ C ₆₀ group consisting of an aryl amine of the Is selected from;
In the above Ar ₁ and Ar ₂ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphanyl group, monoarylphosfinyl group, diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group of, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl A boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphanyl group, a C ₆ ~ C ₆₀ monoarylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and C ₆ It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group of ~C ₆₀ , and in this case, when substituted with a plurality of substituents, these may be the same or different from each other. The method of claim 6,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a C ₆ ~ C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,
The aryl and heteroaryl groups of Ar ₁ and Ar ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, and 5 to 60 nuclear atoms Heteroaryl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosfinyl group or C ₆ ~ C ₆₀ diallyl Phosphinicosuccinic group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ or aryl silyl compounds unsubstituted in. The method of claim 1,
The 5 membered-5 membered fused heterocycle contained in Formula 1 is a compound represented by any one of the following Formulas 4 to 7:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 4 to 7,
Y ₁ and Y ₂ are each the same as defined in claim 1,
X is O or S,
Y ₃ and Y ₄ are the same as or different from each other, and each independently C(R ₅ ) or N, wherein when R ₅ is plural, a plurality of R ₅ are the same or different from each other,
Ring B is 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,
R ₄ and R ₅ 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 of, C ₆ to C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ to C ₄₀ C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cyclo alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, aryl group of C ₆ ~ C ₄₀ boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, 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 group to form a condensed ring Can;
b is an integer from 0 to 4,
In the above R ₄ and R ₅ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl A boron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group are each independently 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 ₆ to C ₄₀ aryl group, heteroaryl group with 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ may be substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ of, In this case, when there are a plurality of the substituents, they may be the same or different from each other. The method of claim 8,
The 5 to 5 membered fused heterocycle is a compound represented by any one of the following formulas 4a to 7b:
[Formula 4a]

[Formula 4b]

[Formula 5a]

[Formula 5b]

[Formula 6a]

[Formula 6b]

[Formula 7a]

[Formula 7b]

In Formulas 4a to 7b,
X, Y ₃ , Y ₄ , R ₄ and b are each the same as defined in claim 8. The method according to claim 6 or 8,
At least one of Ar ₁ , Ar ₂ , R ₄ , and R ₅ is a compound having a substituent represented by Formula 8 below:
[Formula 8]

In Chemical Formula 8,
* Means a part bonded to the corresponding formula,
L is a single bond or is 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,
R ₆ is a C ₆ ~ C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,
The arylene group and heteroarylene group of L and the aryl group and heteroaryl group of R ₆ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group , Heteroaryl group of 5 to 60 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono It may be substituted with one or more substituents selected from the group consisting of an arylphosfinyl group or a C ₆ ~ C ₆₀ diarylphosfinyl group and a C ₆ ~ C ₆₀ arylsilyl group. The method of claim 1,
The compound represented by Formula 1 (wherein the ring A and N-containing ring are fused is a 6-membered-5 membered fused heterocycle) is a compound selected from the group of compounds consisting of the following formula.

The method of claim 1,
The compound represented by Formula 1 (wherein the ring A and the N-containing ring fused is a 5-membered 5-membered fused heterocycle) is a compound selected from the group consisting of the following formula.

The method of claim 1,
The compound represented by Formula 1 is an electron transport layer or an electron transport auxiliary layer material. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer comprises the compound of claim 1. The method of claim 14,
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.