KR20200119647A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to: a novel compound having excellent electron transporting ability and light emitting ability; and an organic electroluminescent element which includes the compound in at least one organic material layer, and thus has improved characteristics such as luminous efficiency, driving voltage, and lifespan. The compound is represented by chemical formula 1.

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 using the same, and more particularly, to a compound having excellent electron transport ability and an organic electric field 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 a light emitting device.

The study of organic electroluminescent (EL) devices (hereinafter simply referred to as'organic EL devices') followed by blue electroluminescence using an anthracene single crystal in 1965, starting from Bernanose's observation of organic thin-film emission in the 1950s, 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 as a light emitting material are reported as fluorescent dopant/host 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.

The present invention provides a novel compound that can be used as an organic material layer material of an organic electroluminescent device, specifically, a light emitting layer material (green), an electron transport layer material, or an electron transport auxiliary layer material, etc., due to its excellent electron injection and transport ability and luminous ability. It aims to do.

In addition, another object of the present invention is to provide an organic electroluminescent device including the above-described novel compound, capable of low voltage driving, high luminous efficiency, and implementing long life characteristics.

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

In Formula 1,

X ₁ to X ₃ are the same as or different from each other, and each independently C(R ₁ ) or N, provided that at least one of X ₁ to X ₃ is N,

At this time, when C (R ₁ ) is plural, the plurality of R ₁ is the same or different from each other,

R ₁ and R 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 It may be selected from or combined with an adjacent group to form a condensed ring,

a is an integer of 0 to 3, b is an integer of 0 to 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,

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,

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group in the R ₁ to R ₂ , and Ar ₁ to Ar ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylsilyl group, 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 ~ C ₄₀ aryl group, nuclear atom number 5 ~ 40 heteroaryl group, C ₆ ~ C ₄₀ Aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C It may be substituted with one or more substituents selected from the group consisting of ₄₀ arylsilyl groups. In this case, when the substituents are plural, they may be the same or different from each other.

In addition, the present invention provides an electron transport layer or an electron transport auxiliary layer 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 has excellent electron transport and luminescence properties, 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 material for a green light-emitting layer (phosphorescent host), an electron transport layer, or an auxiliary electron transport layer, it has higher thermal stability, lower driving voltage, and faster than the conventional host material or electron transport material. An organic electroluminescent device having mobility, high current efficiency, and long life can be manufactured, and further, it can be effectively applied to a full color display panel with improved performance and lifetime.

Hereinafter, the present invention will be described in detail.

<New organic compounds>

According to the present invention, the compound represented by Formula 1 includes a carbazole moiety in which a phenyl group is bonded to carbon positions 2 and 4; And a nitrogen-containing heteroaryl group (X ₁ to X ₃ containing ring), and the carbazole group and the heteroaryl group are directly bonded or linked through a linker (L) as a basic skeleton structure.

The compound represented by Formula 1 having such a structure is a nitrogen-containing aromatic ring (e.g., pyridine), a carbazole group having electron donor (EDG) characteristics and a kind of azine group, which is an electron attracting group (EWG) having high electron absorption. , pyrazine, triazine) in the molecule at the same time. By introducing an azine group, which is a functional group having a strong electron attracting ability (EWG), the electron transfer speed is improved, and thus it is possible to have 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 addition, in the present invention, due to the EWG group and the EDG group contained in the molecule, it is advantageous as a host in the phosphorescent light emitting layer due to the bipolar property, and the charge balance can be adjusted through linkage conversion and sub moiety conversion. Such a bipolar compound can improve hole injection/transport capability, luminous efficiency, driving voltage, life characteristics, durability, etc. due to high recombination power between holes and electrons. In addition, by combining the positions 2 and 4 of the carbazole with a specific substituent and blocking, conventional unsubstituted carbazole or carbazole containing an aryl group substituted at other positions (eg, 1 and 3) Compared to the compound, it is possible to improve the driving voltage and efficiency characteristics of the device. In addition, it is possible to improve electron transport capacity and the like according to the type of substituent introduced into the basic skeleton structure, and adjust the HOMO and LUMO energy levels, thereby having a wide band gap and high carrier transportability. Accordingly, the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a green light emitting layer material (eg, a phosphorescent host material).

In addition, 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 such a compound 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.

Furthermore, in the phosphorescent emission layer, the host material must have a triplet energy gap of the host higher than that of the dopant, because in order to provide effective phosphorescence emission from the dopant, the lowest excited state of the host must have a higher energy than the lowest emission state of the dopant. Conventional carbazole moieties have a large triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, and are mainly used for blue phosphorescent hosts. In contrast, the compound according to the present invention is lower than the triplet energy of a compound having a simple carbazole moiety as a basic skeleton by bonding a phenyl group at positions 2 and 4 of the carbazole group, respectively, and is suitable for green phosphorescence emission. You can have energy.

Due to the foregoing, the compound represented by Formula 1 of the present invention is used as an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (a phosphorescent host material in blue, green and/or red), an electron transport layer/injection layer material, When applied as a light emitting auxiliary layer material, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved. As a result, the organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

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.

Specifically, the compound represented by Formula 1 according to the present invention includes a carbazole moiety in which a plurality of phenyl groups are bonded at a specific position on both sides of the molecule, and a nitrogen-containing heteroaryl group (X ₁ to X ₃ containing ring), and they are directly bonded or have a basic skeleton structure linked through a linker (L).

In Formula 1, the nitrogen-containing heteroaryl group (azine derivative) may be a monocyclic or polycyclic heteroaryl group containing at least one nitrogen atom. For an example of such a nitrogen-containing azine derivative (eg, X ₁ to X ₃ containing heterocycle), X ₁ to X ₃ are the same as or different from each other, and each independently N or CR ₁ , but X ₁ to At least one of X ₃ is N. For a specific example, a plurality of X ₁ to X ₃ includes 1 to 3 N, preferably 2 to 3, more preferably 3 N. By including a heterocycle containing three nitrogens as described above, it exhibits more excellent electron absorption characteristics, which is advantageous for electron injection and transport.

Here, R ₁ may be plural, and a plurality of R ₁ may be the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ groups of an alkyl boron, C ₆ ~ aryl boronic of C _60, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or of , Or it may be combined with an adjacent group (eg, another R ₁ ) to form a condensed ring. Specifically, R ₁ is preferably selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, and heteroaryl group having 5 to 60 nuclear atoms. Do.

For one embodiment according to the present invention, the nitrogen-containing heterocycle (X ₁ to X ₃ containing ring) may be any one selected from the group of substituents represented by the following formulas A-1 to A-5.

In the above A-1 to A-5,

R ₁ , Ar ₁ and Ar ₂ are each as defined in Formula 1.

Wherein also the same each other, Ar ₁ and Ar ₂ in the nitrogen heterocycle or different, each independently represent hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ alkynyl group of C ₄₀ , 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 ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group , C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be selected from the arylamine group. Specifically, Ar ₁ and Ar ₂ are each independently selected from hydrogen, an aryl group of C ₆ to C ₆₀ , and a heteroaryl group having 5 to 60 nuclear atoms.

In Formula 1, the nitrogen-containing heteroaryl group (X ₁ to X ₃ containing ring) is directly or through a linker (L) connected to a carbazole moiety to which a plurality of phenyl groups are bonded.

Specifically, since the carbazole moiety according to the present invention is blocked by bonding a phenyl group at positions 2 and 4, respectively, it is lower than the triplet energy of a compound having a simple carbazole moiety as a basic skeleton, and green It may have triplet energy suitable for phosphorescence emission.

R ₂ may be introduced into the carbazole moiety as various substituents. Such R ₂ 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 alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atom heteroaryl group, C ₁ to C ₄₀ alkyloxy group, 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 arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosfinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of arylamine group, or adjacent It can form a condensed ring by combining with groups (eg, R ₂ ). Specifically, R ₂ is hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and in the heteroaryl group having 5 to 60 nuclear atoms It is preferably selected.

At this time, the number of R ₂ introduced into the carbazole group (eg, b) may be an integer of 0 to 4. For example, when b is 0, R ₂ may be hydrogen. In addition, when b is greater than 0 and less than or equal to 4, a plurality of R ₂ may be the same or different from each other, and each independently may be the remaining substituents excluding hydrogen in the definition of R ₂ .

In Formula 1 according to the present invention, L, which is a linker, may be introduced between the nitrogen-containing indene derivative (X ₁ to X ₃ containing ring) and the carbazole group. Such a linker may use a divalent linker known in the art without limitation. Specifically, L may be a single bond or may be selected from a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

For a preferred example according to the present invention, L may be a substituent represented by any one of the following formulas 2 and 3.

[Formula 2]

[Formula 3]

In Formula 2 or 3,

* Means a portion in which a bond with Formula 1 is formed,

Y is selected from the group consisting of O, S and Se,

n is an integer of 0 to 3.

In addition, the number of L (eg, a) may be an integer of 0 to 3. For example, when a is 0, L may be a single bond (direct bond). In addition, when a is greater than 0 and less than or equal to 3, a plurality of L may be the same or different from each other, and each independently may be the remaining substituents excluding a single bond in the definition of L described above, such as an aryl group or a heteroaryl group.

For one embodiment according to the present invention, L may be each independently a single bond, or may be any one selected from the group of substituents represented by the following structural formula.

In the above structural formula,

* Means a portion in which a bond with Formula 1 is formed. In addition, although not specifically indicated, in the above structural formula, at least one or more substituents known in the art (eg, the same as the definition part of R ₁ ) may be substituted.

In Formula 1, L arylene group, heteroarylene group, R _1, Ar ₁ to Ar ₂ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine 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 ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group , Heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl Group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylamine group, and in this case, when the substituents are plural, they may be the same or different from each other.

According to the present invention, the compound represented by Formula 1 may be further specified in any one of the following Formulas 4 to 9 depending on the type and position of the linker (L).

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 4 to 9,

X ₁ to X ₃ , Y, Ar ₁ , Ar ₂ , R ₂ , b and n are each as defined in Formula 1.

When the above-described Chemical Formulas 4 to 9 are more specific, it may be represented by a compound represented by any one of the following Chemical Formulas 4a to 9a.

[Formula 4a]

[Formula 5a]

[Formula 6a]

[Formula 7a]

[Formula 8a]

[Formula 9a]

In Formulas 4a to 9a,

Y, Ar ₁ , Ar ₂ , R ₂ and n are each as defined in Formula 1.

For a preferred example of the compound represented by any one of Formulas 4 to 9 according to the present invention, X ₁ to X ₃ are the same as or different from each other, and each independently N or C (R ₁ ), but X ₁ to X ₃ is all N,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently selected from an aryl group of C ₆ to C _{60 and} a heteroaryl group having 5 to 60 nuclear atoms,

R ₁ and R ₂ are different from each other, and each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, or a heteroaryl group having 5 to 60 nuclear atoms,

A plurality of Y is the same as or different from each other, each independently O or S, n is an integer of 0 to 3, b is an integer of 0 to 4,

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 71. 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 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 containing the compound of Formula 1 is preferably a green light-emitting layer material (specifically, a phosphorescent host material), 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 2,4-diphenyl-9H-carbazole

<Step 1> Synthesis of 4'-chloro-1,1':3',1''-terphenyl

2,4-dibromo-1-chlorobenzene (100.0g, 369.9 mmol), phenylboronic acid (90.2 g, 739.8 mmol) and Pd(PPh ₃ ) ₄ (21.4 g, 18.5 mmol), K ₂ CO ₃ (153.4 g, 1109.7 mmol) was added to 500ml of Toluene, 100ml of EtOH, and 100ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 4'-chloro-1,1':3',1''-terphenyl (89.1 g, 91% yield) was obtained by column chromatography.

¹ H-NMR: δ 7.40-7.41 (m, 2H), 7.46-7.51 (m, 6H), 7.75 (d, 2H), 7.80 (d, 1H), 7.87-7.88 (m, 2H)

[LCMS]: 265

<Step 2> Synthesis of 2-([1,1':3',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Target compound of step 1 (89.1 g, 336.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (102.5 g, 403.8 mmol) and Pd(dppf)Cl ₂ (8.2 g, 10.1 mmol), Xphos (16.0 g, 33.6 mmol), KOAc (66.0 g, 673.1 mmol) were added to 500 ml of 1,4-Dioxane for 12 hours. During heating to reflux. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent from the filtered organic layer, the target compound 2-([1,1':3',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl was used by column chromatography. -1,3,2-dioxaborolane (85.1 g, yield 71%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 7.40-7.41 (m, 2H), 7.46-7.50 (m, 6H), 7.75 (d, 2H), 7.87 (d, 1H), 8.01 (s, 1H ), 8.13 (d, 1H)

[LCMS]: 357

<Step 3> Synthesis of 2-nitro-4'-phenyl-1,1':2',1''-terphenyl

Target compound of step 2 (64.1 g, 179.9 mmol1-bromo-2-nitrobenzene (36.3 g, 179.9 mmol) and Pd(PPh ₃ ) ₄ (10.4 g, 9.0 mmol), K ₂ CO ₃ (74.6 g, 539.7 mmol) Was added to 500ml of Toluene, 100ml of EtOH, 100ml of H ₂ O and heated to reflux for 12 hours After completion of the reaction, the mixture was extracted with methylene chloride, added with MgSO ₄ , and filtered. Compound 2-nitro-4'-phenyl-1,1':2',1''-terphenyl (50.6 g, 80% yield) was obtained.

¹ H-NMR: δ 7.35 (d, 1H), 7.40-7.41 (m, 2H), 7.46-7.49 (m, 4H), 7.55-7.56 (m, 2H), 7.72 (t, 1H), 7.78-7.79 (m, 2H), 7.89 (t, 1H), 8.00 (d, 1H), 8.03 (d, 1H), 8.13 (s, 1H), 8.15 (d, 1H)

[LCMS]: 352

<Step 4> Synthesis of 2,4-diphenyl-9H-carbazole

The target compound of step 3 (50.6 g, 143.9 mmol), triphenylphosphine (113.3 g, 431.9 mmol), and 500 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, followed by extraction with dichloromethane. Water was removed from the extracted organic layer with MgSO ₄ , and the target compound, 2,4-diphenyl-9H-carbazole (36.8 g, yield 80%) was obtained by column chromatography.

¹ H-NMR: δ 7.20 (t, 1H), 7.40-7.41 (m, 2H), 7.45-7.50 (m, 5H), 7.63 (d, 1H), 7.68 (s, 1H), 7.75-7.79 (m , 4H), 7.84 (s, 1H), 8.19 (d, 1H), 11.66 (s, 1H)

[LCMS]: 320

[Synthesis Example 1] Synthesis of Compound 1

The target compound of Preparation Example 1 (2.1 g, 6.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (1.8 g, 6.6 mmol) Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol) ), P(t-bu) ₃ (0.1 g, 0.6 mmol), NaO(t-bu) (1.3 g, 13.5 mmol) was added to 500 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound (3.0 g, yield 81%) was obtained by column chromatography.

[LCMS]: 551

[Synthesis Example 2] Synthesis of Compound 2

Except that 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used as the reactant, the target compound 3.3 g (yield 80%) was performed in the same manner as in [Synthesis Example 1]. ).

[LCMS]: 627

[Synthesis Example 3] Synthesis of Compound 3

Except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used as the reactant, the target compound 3.4 g (yield 80%) was performed in the same manner as in [Synthesis Example 1]. ).

[LCMS]: 627

[Synthesis Example 4] Synthesis of Compound 4

[Synthesis Example 1], except that 2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used as a reactant. By following the same procedure as, 3.9 g of the title compound (83% yield) was obtained.

[LCMS]: 703

[Synthesis Example 5] Synthesis of Compound 5

[Synthesis Example 1], except that 2-(3'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used as a reactant. By following the same procedure as, 3.9 g of the title compound (83% yield) was obtained.

[LCMS]: 703

[Synthesis Example 6] Synthesis of Compound 6

[Synthesis Example 1], except that 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used as a reactant. The same procedure as described above was performed to obtain 3.7 g (79% yield) of the title compound.

[LCMS]: 703

[Synthesis Example 7] Synthesis of Compound 7

[Synthesis Example 1], except that 2-(4'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used as a reactant. The same procedure as described above was performed to obtain 3.7 g (79% yield) of the title compound.

[LCMS]: 703

[Synthesis Example 8] Synthesis of Compound 8

Except for using 2-(3''-bromo-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine as a reactant Was performed in the same manner as in [Synthesis Example 1] to obtain 3.9 g (yield 75%) of the target compound.

[LCMS]: 779

[Synthesis Example 9] Synthesis of Compound 9

The same procedure as in [Synthesis Example 1], except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used as the reactant To obtain the title compound 3.3 g (yield 79%).

[LCMS]: 627

[Synthesis Example 10] Synthesis of Compound 10

[Synthesis Example 1], except that 2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant. ] To obtain the title compound 3.7 g (yield 78%).

[LCMS]: 703

[Synthesis Example 11] Synthesis of Compound 11

[Synthesis Example 1], except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant. ] To obtain the title compound 3.7 g (yield 78%).

[LCMS]: 703

[Synthesis Example 12] Synthesis of Compound 12

2-([1,1'-biphenyl]-4-yl)-4-(4'-bromo-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5 as reactant Except for using -triazine, the same procedure as in [Synthesis Example 1] was carried out to obtain 3.9 g (yield 75%) of the target compound.

[LCMS]: 779

[Synthesis Example 13] Synthesis of Compound 13

2-([1,1'-biphenyl]-4-yl)-4-(3'-bromo-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5 as reactant Except for using -triazine, the same procedure as in [Synthesis Example 1] was carried out to obtain 3.9 g (yield 75%) of the target compound.

[LCMS]: 779

[Synthesis Example 14] Synthesis of Compound 14

2-([1,1'-biphenyl]-4-yl)-4-(3'-bromo-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5 Except for using -triazine, the same procedure as in [Synthesis Example 1] was performed to obtain 4.2 g (yield 80%) of the target compound.

[LCMS]: 779

[Synthesis Example 15] Synthesis of Compound 15

2-([1,1'-biphenyl]-4-yl)-4-(4'-bromo-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5 Except for using -triazine, the same procedure as in [Synthesis Example 1] was performed to obtain 4.2 g (yield 80%) of the target compound.

[LCMS]: 779

[Synthesis Example 16] Synthesis of Compound 16

Except for using 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine as the reactant, the target compound 3.2 g ( Yield 76%).

[LCMS]: 626

[Synthesis Example 17] Synthesis of Compound 17

Except that 4-([1,1'-biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine was used as the reactant, the same procedure as in [Synthesis Example 1] was performed. To give the compound 3.5 g (75% yield).

[LCMS]: 702

[Synthesis Example 18] Synthesis of Compound 18

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-2-phenylpyrimidine as a reactant, the same procedure as in [Synthesis Example 1] was performed to Compound 3.6 g (yield 76%) was obtained.

[LCMS]: 702

[Synthesis Example 19] Synthesis of Compound 19

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(4'-bromo-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine as a reactant , 4.1 g of the target compound (79% yield) was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 778

[Synthesis Example 20] Synthesis of Compound 20

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(3'-bromo-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine as a reactant , 4.1 g of the target compound (79% yield) was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 778

[Synthesis Example 21] Synthesis of Compound 21

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(3'-bromo-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine as a reactant , 4.0 g (yield 76%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 778

[Synthesis Example 22] Synthesis of Compound 22

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(4'-bromo-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine as a reactant , 4.0 g (yield 76%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 778

[Synthesis Example 23] Synthesis of Compound 23

Except for using 2-(6-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.6 g of the title compound (75% yield).

[LCMS]: 717

[Synthesis Example 24] Synthesis of Compound 24

Except for using 2-(7-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to give 4.0 g (yield 76%) of the title compound.

[LCMS]: 717

[Synthesis Example 25] Synthesis of Compound 25

Except for using 2-(8-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.5 g of the target compound (73% yield) was obtained.

[LCMS]: 717

[Synthesis Example 26] Synthesis of Compound 26

Except for using 2-(9-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.4 g (yield 71%) of the target compound was obtained.

[LCMS]: 717

[Synthesis Example 27] Synthesis of Compound 27

Except for using 2-(6-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.6 g of the title compound (75% yield).

[LCMS]: 717

[Synthesis Example 28] Synthesis of Compound 28

Except for using 2-(7-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to give 4.0 g (yield 76%) of the title compound.

[LCMS]: 717

[Synthesis Example 29] Synthesis of Compound 29

Except for using 2-(8-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.5 g of the target compound (73% yield) was obtained.

[LCMS]: 717

[Synthesis Example 30] Synthesis of Compound 30

Except for using 2-(9-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.4 g (yield 71%) of the target compound was obtained.

[LCMS]: 717

[Synthesis Example 31] Synthesis of Compound 31

Except that 2-(6-bromodibenzo[b,d]furan-2-yl)-4,6-diphenyl-1,3,5-triazine was used as a reactant, the same procedure as in [Synthesis Example 1] was performed. Then, 3.5 g of the target compound (73% yield) was obtained.

[LCMS]: 717

[Synthesis Example 32] Synthesis of Compound 32

Except for using 2-(7-bromodibenzo[b,d]furan-2-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.4 g (yield 71%) of the target compound was obtained.

[LCMS]: 717

[Synthesis Example 33] Synthesis of Compound 33

Except for using 2-(8-bromodibenzo[b,d]furan-2-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to give 4.0 g (yield 76%) of the title compound.

[LCMS]: 717

[Synthesis Example 34] Synthesis of Compound 34

Except for using 2-(9-bromodibenzo[b,d]furan-2-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.5 g of the target compound (73% yield) was obtained.

[LCMS]: 717

[Synthesis Example 35] Synthesis of Compound 35

Except for using 2-(6-bromodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.4 g (yield 71%) of the target compound was obtained.

[LCMS]: 717

[Synthesis Example 36] Synthesis of Compound 36

Except for using 2-(7-bromodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.6 g of the title compound (75% yield).

[LCMS]: 717

[Synthesis Example 37] Synthesis of Compound 37

Except for using 2-(8-bromodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to give 4.0 g (yield 76%) of the title compound.

[LCMS]: 717

[Synthesis Example 38] Synthesis of Compound 38

Except for using 2-(9-bromodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] Then, 3.5 g of the target compound (73% yield) was obtained.

[LCMS]: 717

[Synthesis Example 39] Synthesis of Compound 39

Using 2-([1,1'-biphenyl]-4-yl)-4-(6-bromodibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine as a reactant Except that, 3.6 g (yield 68%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 793

[Synthesis Example 40] Synthesis of Compound 40

Using 2-([1,1'-biphenyl]-4-yl)-4-(8-bromodibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine as a reactant Except that, 3.6 g (yield 68%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 793

[Synthesis Example 41] Synthesis of Compound 41

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(6-bromodibenzo[b,d]furan-4-yl)-2-phenylpyrimidine as a reactant, the [synthesis The same procedure as in Example 1] was performed to obtain 3.6 g of the title compound (68% yield).

[LCMS]: 792

[Synthesis Example 42] Synthesis of Compound 42

Except for using 4-([1,1'-biphenyl]-4-yl)-6-(8-bromodibenzo[b,d]furan-4-yl)-2-phenylpyrimidine as a reactant, the above [synthesis The same procedure as in Example 1] was performed to obtain 3.6 g of the title compound (68% yield).

[LCMS]: 792

[Synthesis Example 43] Synthesis of Compound 43

Except for using 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.4 g (79% yield) of the target compound.

[LCMS]: 641

[Synthesis Example 44] Synthesis of Compound 44

[Synthesis Example 1], except for using 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant By following the same procedure as, 3.3 g of the title compound (68% yield) was obtained.

[LCMS]: 717

[Synthesis Example 45] Synthesis of Compound 45

Except for using 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant, [Synthesis Example 1] and By performing the same procedure, 3.4 g (yield 70%) of the target compound was obtained.

[LCMS]: 717

[Synthesis Example 46] Synthesis of Compound 46

2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5- Except that triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain 3.6 g of the target compound (68% yield).

[LCMS]: 793

[Synthesis Example 47] Synthesis of Compound 47

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5- Except that triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain 3.6 g of the target compound (68% yield).

[LCMS]: 793

[Synthesis Example 48] Synthesis of Compound 48

Except for using 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.4 g (79% yield) of the target compound.

[LCMS]: 641

[Synthesis Example 49] Synthesis of Compound 49

[Synthesis Example 1], except that 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used as a reactant. By performing the same procedure as to obtain the title compound 3.7 g (yield 77%).

[LCMS]: 717

[Synthesis Example 50] Synthesis of Compound 50

[Synthesis Example 1], except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used as a reactant. By performing the same procedure as to obtain the title compound 3.7 g (76% yield).

[LCMS]: 717

[Synthesis Example 51] Synthesis of Compound 51

2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 52] Synthesis of Compound 52

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 53] Synthesis of Compound 53

Except for using 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.4 g (79% yield) of the target compound.

[LCMS]: 641

[Synthesis Example 54] Synthesis of Compound 54

[Synthesis Example 1], except that 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine was used as a reactant. By performing the same procedure as to obtain the title compound 3.7 g (yield 77%).

[LCMS]: 717

[Synthesis Example 55] Synthesis of Compound 55

[Synthesis Example 1], except for using 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine as a reactant. By performing the same procedure as to obtain the title compound 3.7 g (76% yield).

[LCMS]: 717

[Synthesis Example 56] Synthesis of Compound 56

2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 57] Synthesis of Compound 57

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 58] Synthesis of Compound 58

Except for using 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant, the same procedure as in [Synthesis Example 1] This was carried out to obtain 3.4 g (79% yield) of the target compound.

[LCMS]: 641

[Synthesis Example 59] Synthesis of Compound 59

[Synthesis Example 1], except for using 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant By performing the same procedure as to obtain the title compound 3.7 g (yield 77%).

[LCMS]: 717

[Synthesis Example 60] Synthesis of Compound 60

[Synthesis Example 1], except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used as a reactant. By performing the same procedure as to obtain the title compound 3.7 g (76% yield).

[LCMS]: 717

[Synthesis Example 61] Synthesis of Compound 61

2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 62] Synthesis of Compound 62

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5- Except for using triazine, by performing the same procedure as in [Synthesis Example 1] to obtain 4.0 g (yield 75%) of the target compound.

[LCMS]: 793

[Synthesis Example 63] Synthesis of Compound 63

The same procedure as in [Synthesis Example 1] was performed, except that 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine was used as the reactant. Thus, 3.7 g (yield 76%) of the target compound was obtained.

[LCMS]: 731

[Synthesis Example 64] Synthesis of Compound 64

Except for using 2-(4-bromophenyl)-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine as a reactant, the above [Synthesis Example 1] and By performing the same procedure, 3.8 g of the title compound (70% yield) was obtained.

[LCMS]: 807

[Synthesis Example 65] Synthesis of Compound 65

Except for using 2-(3-bromophenyl)-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine as a reactant, the above [Synthesis Example 1] and By performing the same procedure, 3.8 g of the title compound (70% yield) was obtained.

[LCMS]: 807

[Synthesis Example 66] Synthesis of Compound 66

2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine as reactant Except for using, by performing the same procedure as in [Synthesis Example 1] to obtain 3.8 g (yield 65%) of the target compound.

[LCMS]: 884

[Synthesis Example 67] Synthesis of Compound 67

Using 2-(6-bromodibenzo[b,d]furan-4-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant Except, by performing the same procedure as in [Synthesis Example 1], 3.6 g (yield 66%) of the target compound was obtained.

[LCMS]: 807

[Synthesis Example 68] Synthesis of Compound 68

Using 2-(8-bromodibenzo[b,d]furan-4-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine as a reactant Except, by performing the same procedure as in [Synthesis Example 1], 3.6 g (yield 66%) of the target compound was obtained.

[LCMS]: 807

[Synthesis Example 69] Synthesis of Compound 69

Using 2-(6-bromodibenzo[b,d]furan-4-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine as a reactant Except, by performing the same procedure as in [Synthesis Example 1], 3.6 g (yield 66%) of the target compound was obtained.

[LCMS]: 807

[Synthesis Example 70] Synthesis of Compound 70

Using 2-(7-bromodibenzo[b,d]furan-4-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine as a reactant Except, by performing the same procedure as in [Synthesis Example 1], 3.6 g (yield 66%) of the target compound was obtained.

[LCMS]: 807

[Synthesis Example 71] Synthesis of Compound 71

Except for using 2-(8-bromodibenzo[b,d]furan-4-yl)-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine as a reactant Then, 3.6 g (yield 60%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].

[LCMS]: 898

[Examples 1 to 71] Fabrication of a blue organic electroluminescent device

After the compounds 1 to 71 synthesized in Synthesis Example were subjected to high-purity sublimation purification by a conventionally known method, a blue organic electroluminescent device was fabricated as follows.

First, ITO (Indium tin oxide) was washed with a thin film coated glass substrate with a thickness of 1500 Å with distilled water and ultrasonic waves. 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 The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30 nm)/Compounds 1 to 71 (30 nm) /LiF (1 nm)/Al (200 nm) was stacked in order to fabricate 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 1-71 in Table 1 30 Electron injection layer LiF One cathode Al 200

[Comparative Example 1] Fabrication of blue organic electroluminescent device

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

[Comparative Example 2] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device of Comparative Example 2 was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transport layer material.

[Comparative Example 3] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device of Comparative Example 3 was manufactured in the same manner as in Example 1, except that Ref-1 having the following structure was used instead of Compound 1 as the electron transport layer material.

[Comparative Example 4] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device of Comparative Example 4 was manufactured in the same manner as in Example 1, except that Ref-2 having the following structure was used instead of Compound 1 as the electron transport layer material.

For reference, the structures of NPB, ADN, Alq3, Ref-1 and Ref-2 used in Examples 1 to 71 and Comparative Examples 1 to 4 are as follows, respectively.

[Evaluation Example 1]

For each of the blue organic electroluminescent devices prepared in Examples 1 to 71 and Comparative Examples 1 to 4, the driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. Indicated.

Sample
Electron transport layer
material
Driving voltage
(V)
EL peak
(nm)
Current efficiency
(cd/A)
Example 1
One
3.6
456
6.8
Example 2
2
3.2
456
6.7
Example 3
3
3.2
457
6.9
Example 4
4
3.6
456
7.1
Example 5
5
3.2
457
7.1
Example 6
6
3.2
456
7.1
Example 7
7
3.9
456
6.9
Example 8
8
3.6
457
6.7
Example 9
9
3.6
456
7.0
Example 10
10
3.2
457
7.1
Example 11
11
3.2
456
6.8
Example 12
12
3.1
456
7.3
Example 13
13
3.9
457
6.9
Example 14
14
3.9
452
6.8
Example 15
15
3.3
448
6.7
Example 16
16
3.6
460
6.8
Example 17
17
3.6
456
6.9
Example 18
18
3.2
456
7.1
Example 19
19
3.2
457
7.1
Example 20
20
3.2
456
6.8
Example 21
21
3.9
456
6.9
Example 22
22
3.6
457
6.7
Example 23
23
3.8
457
7.1
Example 24
24
3.2
452
6.9
Example 25
25
3.1
456
7.3
Example 26
26
3.9
457
6.9
Example 27
27
3.9
457
6.8
Example 28
28
3.9
459
6.9
Example 29
29
3.3
456
7.1
Example 30
30
3.8
455
6.9
Example 31
31
3.4
459
6.8
Example 32
32
4.1
457
6.4
Example 33
33
3.6
456
7.1
Example 34
34
3.3
457
6.7
Example 35
35
3.6
456
7.0
Example 36
36
4.1
456
6.9
Example 37
37
3.2
457
6.8
Example 38
38
3.2
456
6.9
Example 39
39
3.3
457
6.8
Example 40
40
3.6
456
7.0
Example 41
41
4.1
456
7.1
Example 42
42
3.2
457
6.8
Example 43
43
3.2
452
6.7
Example 44
44
3.3
448
6.9
Example 45
45
3.6
456
7.1
Example 46
46
3.2
457
7.1
Example 47
47
3.3
456
6.8
Example 48
48
3.6
456
6.9
Example 49
49
4.1
457
6.9
Example 50
50
3.7
452
6.9
Example 51
51
3.9
448
7.1
Example 52
52
3.8
460
7.1
Example 53
53
3.2
456
6.9
Example 54
54
3.2
456
6.8
Example 55
55
3.8
457
6.6
Example 56
56
4.1
465
6.8
Example 57
57
3.7
455
6.9
Example 58
58
3.9
459
7.1
Example 59
59
3.8
457
7.1
Example 60
60
3.2
452
6.9
Example 61
61
3.2
457
6.4
Example 62
62
3.8
452
7.1
Example 63
63
4.1
456
6.7
Example 64
64
3.6
460
7.1
Example 65
65
4.1
456
6.9
Example 66
66
4.1
456
6.8
Example 67
67
3.7
457
6.7
Example 68
68
3.9
459
6.8
Example 69
69
3.8
457
6.7
Example 70
70
3.6
456
6.7
Example 71
71
3.9
457
6.9
Comparative Example 1
Alq ₃
4.7
459
5.9
Comparative Example 2
-
4.8
460
5.6
Comparative Example 3
Ref-1
4.6
460
6.3
Comparative Example 4
Ref-2
4.5
459
6.5

As shown in Table 2, the blue organic electroluminescent devices of Examples 1 to 71 using the compound of the present invention as an electron transport layer material include the blue organic electroluminescent devices of Comparative Example 1 using Alq3 for the electron transport layer; The blue organic electroluminescent device of Comparative Example 2 without an electron transport layer; The blue organic electroluminescent device of Comparative Example 3 using unsubstituted carbazole; And it was found that the blue organic light emitting device of Comparative Example 4 using a carbazole substituted with a phenyl group at carbon positions 1 and 3 showed superior performance in terms of driving voltage, emission peak, and current efficiency.

[Examples 72 to 142] Fabrication of green organic electroluminescent device

Compounds 1 to 71 synthesized in Synthesis Example were subjected to high-purity sublimation purification by a commonly known method, and then a green organic electroluminescent device was manufactured as follows.

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

On the thus prepared ITO transparent glass substrate (electrode), m-MTDATA (60 nm)/TCTA (80 nm)/90 wt% of compounds 1 to 71 + 10 wt% of Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were sequentially stacked to fabricate a green organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used at this time are as follows, respectively.

[Comparative Example 5] Fabrication of green organic electroluminescent device

The green organic electroluminescent device of Comparative Example 5 was manufactured in the same manner as in Example 72, except that CBP was used instead of Compound 1 as a light emitting host material when forming the emission layer.

The structure of the CBP used at this time is as follows.

[Comparative Example 6] Fabrication of green organic electroluminescent device

The green organic electroluminescent device of Comparative Example 6 was manufactured in the same manner as in Example 72, except that Ref-1 was used instead of Compound 1 as a light emitting host material when forming the emission layer.

[Comparative Example 7] Fabrication of green organic electroluminescent device

The green organic electroluminescent device of Comparative Example 7 was manufactured in the same manner as in Example 72, except that Ref-2 was used instead of Compound 1 as a light emitting host material when forming the emission layer.

[Evaluation Example 2]

For the green organic electroluminescent devices prepared in Examples 72 to 142 and Comparative Examples 5 to 7, respectively, driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below. Shown in.

Sample
Host material
Driving voltage
(V)
Emission peak (nm)
Current efficiency (cd/A)
Example 72
One
4.0
458
57.0
Example 73
2
3.6
458
59.5
Example 74
3
4.1
458
56.5
Example 75
4
3.8
458
58.3
Example 76
5
3.7
459
59.3
Example 77
6
4.1
458
57.0
Example 78
7
3.8
458
59.1
Example 79
8
4.1
458
57.0
Example 80
9
3.8
459
59.1
Example 81
10
3.9
458
58.0
Example 82
11
3.6
458
60.5
Example 83
12
3.8
459
57.7
Example 84
13
3.8
458
58.6
Example 85
14
3.7
458
55.9
Example 86
15
3.8
458
58.5
Example 87
16
3.8
458
57.0
Example 88
17
3.7
458
59.1
Example 89
18
3.7
458
58.0
Example 90
19
3.8
458
60.0
Example 91
20
3.8
459
58.8
Example 92
21
3.9
457
56.0
Example 93
22
4.0
458
57.0
Example 94
23
3.6
459
59.1
Example 95
24
4.1
458
58.0
Example 96
25
3.9
457
54.8
Example 97
26
4.0
457
60.5
Example 98
27
3.8
458
57.7
Example 99
28
3.8
459
58.6
Example 100
29
3.9
458
55.9
Example 101
30
4.0
457
58.5
Example 102
31
3.6
458
59.1
Example 103
32
4.1
458
60.0
Example 104
33
3.9
459
57.2
Example 105
34
4.0
457
50.1
Example 106
35
3.6
457
58.5
Example 107
36
4.1
458
57.1
Example 108
37
3.8
457
58.9
Example 109
38
3.7
458
58.4
Example 110
39
4.1
458
57.0
Example 111
40
3.8
459
59.1
Example 112
41
3.9
458
58.0
Example 113
42
3.6
458
60.5
Example 114
43
3.8
459
57.7
Example 115
44
4.1
458
58.6
Example 116
45
3.8
458
55.9
Example 117
46
3.9
458
57.0
Example 118
47
3.6
459
59.1
Example 119
48
4.1
458
58.0
Example 120
49
3.8
458
60.5
Example 121
50
3.9
459
58.0
Example 122
51
3.6
458
60.5
Example 123
52
3.8
458
57.7
Example 124
53
3.9
458
59.1
Example 125
54
3.6
458
58.0
Example 126
55
3.8
458
60.5
Example 127
56
3.8
458
58.0
Example 128
57
3.8
458
58.0
Example 129
58
3.7
458
60.5
Example 130
59
3.8
459
57.7
Example 131
60
3.8
458
58.6
Example 132
61
3.7
458
58.5
Example 133
62
3.7
458
57.0
Example 134
63
3.8
458
59.1
Example 135
64
3.7
459
58.0
Example 136
65
3.8
458
58.0
Example 137
66
4.1
458
60.5
Example 138
67
3.8
458
57.7
Example 139
68
3.9
459
59.1
Example 140
69
4.0
458
58.0
Example 141
70
4.1
458
60.5
Example 142
71
3.9
458
57.0
Comparative Example 5
CBP
5.5
459
44.2
Comparative Example 6
Ref-1
5.3
459
49.1
Comparative Example 7
Ref-2
4.8
459
54.1

As shown in Table 3, the green organic electroluminescent device of Examples 72 to 142 using the compound according to the present invention as a host material of the emission layer includes the green organic electroluminescent device of Comparative Example 5 in which CBP was applied as a host material; The green organic light-emitting device of Comparative Example 6 using unsubstituted carbazole; And it was found that the current efficiency and driving voltage were excellent compared to the green organic light emitting device of Comparative Example 7 using carbazole substituted with a phenyl group at carbon positions 1 and 3.

Claims (11)

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

In Formula 1,
X ₁ to X ₃ are the same as or different from each other, and each independently C(R ₁ ) or N, provided that at least one of X ₁ to X ₃ is N,
At this time, when C (R ₁ ) is plural, the plurality of R ₁ is the same or different from each other,
R ₁ and R 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 It may be selected from or combined with an adjacent group to form a condensed ring,
a is an integer of 0 to 3, b is an integer of 0 to 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,
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,
The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group in the R ₁ to R ₂ , and Ar ₁ to Ar ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylsilyl group, 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 ~ C ₄₀ aryl group, nuclear atom number 5 ~ 40 heteroaryl group, C ₆ ~ C ₄₀ Aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C It may be substituted with one or more substituents selected from the group consisting of ₄₀ arylsilyl groups. In this case, when the substituents are plural, they may be the same or different from each other. The method of claim 1,
L is a compound represented by any one of the following formula (2) and formula (3):
[Formula 2]

[Formula 3]

In Formula 2 or 3,
* Means a portion in which a bond with Formula 1 is formed,
Y is selected from the group consisting of O, S and Se,
n is an integer of 0 to 3. The method of claim 1,
L is a single bond or a linker selected from the group of substituents represented by the following structural formula.

The method of claim 1,
remind

Is a compound selected from the group of substituents represented by the following formulas A-1 to A-5:

In the above A-1 to A-5,
R ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. The method of claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 4 to 9:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 4 to 9,
X ₁ to X ₃ , Y, Ar ₁ , Ar ₂ , R ₂ , and b are each as defined in claim 1,
n is an integer of 0 to 3. The method of claim 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently selected from the group consisting of an aryl group of C ₆ to C _{60 and} a heteroaryl group having 5 to 60 nuclear atoms,
The aryl and heteroaryl groups of Ar ₁ to Ar ₂ are each independently hydrogen, deuterium (D), 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ - an aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~ C ₆₀ aryl optionally substituted with 1 substituent at least one selected from the group consisting of amine groups of In this case, when the substituents are plural, they are the same or different from each other. The method of claim 2,
The compound represented by Formula 1 (wherein L is a substituent represented by Formula 2) is a compound selected from the group consisting of the following formula.

The method of claim 1,
The compound represented by Formula 1 (wherein L is a substituent represented by Formula 3) 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 material 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 according to any one of claims 1 to 9 EL device. The method of claim 10,
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.