KR20240107002A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, it relates to an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, and luminescence ability, and including the same in one or more organic layers to increase luminous efficiency, This is about an organic electroluminescent device with improved characteristics such as driving voltage and lifespan.

Description

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

The present invention relates to novel organic compounds and organic electroluminescent devices using the same, and more specifically, to organic compounds with excellent electron injection and transport capabilities, heat resistance, and electrochemical stability, and their inclusion in one or more organic material layers to improve luminous efficiency and driving. It relates to an organic electroluminescent device with improved characteristics such as voltage and lifespan.

When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as an 'organic EL device'), holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

So far, hole injection layer and hole transport layer. NPB, BCP, Alq ₃ , etc. are widely known as hole blocking layer and electron transport layer materials, and anthracene derivatives are reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, although conventional organic layer materials are advantageous in terms of luminescent properties, their glass transition temperature is low and their thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

The present invention provides a novel compound that has excellent electron transport ability, heat resistance, carrier transport ability, luminescence ability, etc., and can be used as an organic layer material of an organic electroluminescent device, specifically an electron transport layer material or an electron transport auxiliary layer material, etc. The purpose.

Another object of the present invention is to provide an organic electroluminescent device containing the novel compound, which has low driving voltage, high luminous efficiency, excellent electrical stability, and improved lifespan.

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

(In Formula 1 above,

Ar ₁ is a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, or a heterocycle with 3 to 40 nuclear atoms. Alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphos Pin group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine selected from the group consisting of a heteroarylamine group having 5 to 60 nuclear atoms,

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

X ₄ to X _{8 are} the same or different from each other and are each independently N or C(R ₂ ), provided that at least one of X ₄ to

R ₁ , R ₂ , Ar ₂ and Ar ₃ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl with 5 to 60 nuclear atoms 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 alkylboron group, C ₆ to C ₆₀ aryl boron group, C ₁ to C ₄₀ alkylphosphine group, C ₆ to C ₆₀ arylphosphine group, C ₁ to C ₄₀ alkylphosphine oxide group, C ₆ to C ₆₀ It is selected from the group consisting of an arylphosphine oxide group, an arylamine group of C ₆ to C ₆₀ , an (aryl)(heteroaryl)amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms,

n1 and n2 are each integers from 0 to 4,

L ₁ and L ₂ are the same or different from each other, and are each independently selected from the group consisting of an arylene group of C ₆ to C ₃₀ and a heteroarylene group of 5 to 30 nuclear atoms,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, and arylsilyl group of Ar ₁ to Ar ₃ , R ₁ and R ₂ , alkyl boron group, aryl boron group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group and heteroaryl amine group; And the arylene group and heteroarylene group of L ₁ and L ₂ are each independently selected from deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to 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 ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C 40 alkylphosphine oxide group _, C ₆ ~ C ₆₀ arylphosphine oxide group, Substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ , and a heteroarylamine group having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same or different from each other).

In addition, the present invention is an anode; cathode; Provided is an organic electroluminescent device comprising one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers including the compound represented by the above-mentioned formula (1).

According to one example, the organic material layer containing the compound may be at least one selected from the group consisting of an electron transport layer and an electron transport auxiliary layer.

Since the compound of the present invention is excellent in electron transport ability, heat resistance, carrier transport ability, luminescence ability, etc., it can be used as an organic layer material of an organic electroluminescent device. In particular, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, an organic electroluminescent device can be manufactured with excellent light emission performance, low driving voltage, high efficiency, and long life characteristics compared to conventional materials. Full-color display panels with improved performance and lifespan can also be manufactured.

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

1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.
Figure 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

Hereinafter, the present invention will be described.

<New compound>

The compound according to the present invention is a benzene ring in which the first nitrogen-containing heteroaromatic ring is bonded to the benzene ring directly or through a linker, and the second nitrogen-containing heteroaromatic ring is in an ortho position with respect to the first nitrogen-containing heteroaromatic ring. It is a structure in which an arylene group, etc. is substituted at another position of the benzene ring while being bonded (introduced) to the 2nd carbon position, and is represented by the above formula (1). The compound of the present invention has excellent electron injection and transport capabilities, heat resistance, and electrochemical stability, and is an organic material layer material, especially an electron transport layer material, that can realize the characteristics of an organic electroluminescent device, such as high efficiency, long life, and low driving voltage of the device. Alternatively, it can be used as an auxiliary electron transport layer.

Specifically, in the compound represented by Formula 1, the first and second nitrogen-containing heteroaromatic rings are each 6-membered heteroaromatic ring containing at least one nitrogen (N), and are selected from the group consisting of pyridine, pyrimidine, There is triazine. These first and second nitrogen-containing heteroaromatic rings are electron attractors (EWG) with high electron absorption, and can improve electron mobility and electron transport and injection properties of the compound. Therefore, when the compound according to the present invention is applied as a material for the electron transport layer or electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light emitting layer, and as a result, the driving voltage of the device can be increased. is lowered, and high efficiency and long life characteristics can be realized.

These first and second nitrogen-containing heteroaromatic rings are introduced into the benzene ring at ortho positions to each other. That is, the first and second nitrogen-containing heteroaromatic rings are introduced at positions 1 and 2 of the benzene ring, respectively. At this time, the first and second nitrogen-containing heteroaromatic rings are introduced into the benzene ring directly or through a linker. In this way, when the first and second nitrogen-containing heteroaromatic rings are bonded to the benzene ring in the ortho-position, the driving voltage can be reduced.

Additionally, a substituent (Ar ₁ ) such as an aryl group is introduced into another position of the benzene ring. Depending on the substituent (Ar ₁ ), the electron-withdrawing or electron-donating characteristics can be strengthened. If a substituent (Ar ₁ ) is introduced at the 3-position of the benzene ring, the electron injection characteristics are improved, and if a substituent (Ar ₁ ) is introduced at the 4-position of the benzene ring, the electron transfer characteristics are improved.

In addition, the compound represented by Formula 1 may have various substituents (R) introduced into the nitrogen-containing heteroaromatic ring described above. Depending on the type of substituent (R), the HOMO and LUMO energy levels of the compound can be adjusted, allowing it to have a wide band gap and high carrier transport properties. In addition, the molecular weight of the compound of the present invention is significantly increased by introducing various substituents (e.g., aryl group, heteroaryl group, etc.), and as a result, the glass transition temperature is high, so thermal and electrochemical stability can be improved. .

As described above, the compound represented by Formula 1 of the present invention is excellent in electron injection and transport ability, thermal stability, electrochemical stability, etc., and is used as an organic material layer material of an organic electroluminescent device, specifically a light emitting layer material, and an electron transport layer/injection layer material. , can be used as an electron transport auxiliary layer material, more specifically as an electron transport layer material or an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of an organic electroluminescent device containing the compound of Formula 1 can be greatly improved, and the performance of a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.

In the compound represented by Formula 1, Ar ₁ is a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , 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 ₁ ~ C ₄₀ alkylphosphine group , C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ is selected from the group consisting of (aryl)(heteroaryl)amine groups and heteroarylamine groups having 5 to 60 nuclear atoms, specifically cyano groups, C ₁ to C ₄₀ alkyl groups, C ₃ to C ₄₀ cycloalkyl groups, It may be selected from the group consisting of a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ .

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, and arylboron of Ar ₁ group, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group are each independently deuterium, halogen, cyano group, and nitro group. group, amino 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 with 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 , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group, and Substituted or unsubstituted with one or more substituents selected from the group consisting of heteroarylamine groups having 5 to 60 nuclear atoms, and specifically, each independently deuterium, halogen, cyano group, nitro group, amino group, and C ₁ to C ₄₀ alkyl group. , C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkylphosphine group. , C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, and C ₆ ~ C ₆₀ arylamine group selected from the group consisting of It may be substituted or unsubstituted with one or more substituents. If the substituents are plural, they may be the same or different from each other.

According to one example, Ar ₁ may be selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms. At this time, the aryl group and heteroaryl group of Ar ₁ are cyano group, C ₃ ~ C ₂₀ cycloalkyl group, heterocycloalkyl group with 3 to 20 nuclear atoms, C ₆ ~ C ₃₀ aryl group, 5 to 30 nuclear atoms. Consisting of heteroaryl groups, C ₁ to C ₂₀ alkylphosphine groups, C ₆ to C ₃₀ arylphosphine groups, C ₁ to C ₂₀ alkylphosphine oxide groups, and C ₆ to C ₃₀ arylphosphine oxide groups. It may be substituted or unsubstituted with one or more substituents selected from the group. If the substituents are plural, they may be the same or different from each other.

According to another example, Ar ₁ may be selected from the group consisting of the following substituents S1-1 to S1-7. However, it is not limited to this.

In the substituents S1-1 to S1-7,

Y ₁ is selected from the group consisting of O, S, N(R ₃ ) and C(R ₄ )(R ₅ ),

R ₃ to R ₅ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C 40 alkylphosphine oxide group _, C ₆ ~ C ₆₀ arylphosphine oxide group, Is selected from the group consisting of an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ and a heteroarylamine group of 5 to 60 nuclear atoms, or an adjacent group (e.g. R ₄ -R ₅ ) and condensed to form a condensed ring,

a1 is an integer from 0 to 5, specifically 0 or 1,

a2 is an integer from 0 to 4, specifically 0 or 1,

a3 is an integer from 0 to 7, specifically 0 or 1,

a4 is an integer from 0 to 8, specifically 0 or 1,

A plurality of R is the same or different from each other,

R is a cyano group, a cycloalkyl group of C ₃ to C ₂₀ , a heterocycloalkyl group of 3 to 20 nuclear atoms, an aryl group of C ₆ to C ₃₀ , a heteroaryl group of 5 to 30 nuclear atoms, C ₁ to C ₂₀ It is selected from the group consisting of an alkylphosphine group, a C ₆ ~ C ₃₀ arylphosphine group, a C ₁ ~ C ₂₀ alkylphosphine oxide group, and a C ₆ ~ C ₃₀ arylphosphine oxide group.

According to another example, Ar ₁ may be selected from the group consisting of the following substituents S2-1 to S2-28. However, it is not limited to this.

In the substituents S2-1 to S2-28,

* refers to the part where a bond is formed with Formula 1,

a5 is 0 or 1.

The hydrogen of the above-mentioned substituents S2-1 to S2-28 is deuterium (D), halogen, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heteroaryl having 5 to 10 nuclear atoms. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of groups.

Depending on the position at which Ar ₁ is introduced, the compound represented by Formula 1 may be a compound represented by Formula 2 or 3 below, but is not limited thereto. Compounds represented by Formula 2 or 3 below have superior electron injection or electron transport capabilities compared to compounds without Ar ₁ (i.e., compounds where Ar ₁ is hydrogen), so driving voltage characteristics can be improved.

In Formulas 2 and 3,

X ₁ to X ₈ , Ar ₁ to Ar ₃ , n1, n2, L ₁ and L ₂ are each as defined in Formula 1 above.

In the compound represented by Formula 1, X ₁ to X ₃ are the same or different from each other and are each independently N or C(R ₁ ), provided that at least one of X ₁ to X ₃ is N. At this time, if C(R ₂ ) is plural, the plurality of R ₂ are the same or different from each other. These X _{1 to} In this way, by including at least one nitrogen-containing heteroaromatic ring, the compound of Formula 1 according to the present invention may exhibit better electron absorption characteristics and be advantageous for electron injection and transport.

According to one example, the X ₁ to X ₃ -containing ring moiety ( moiety) may be any one of the following moieties Az1-1 to Az1-5, but is not limited thereto.

In the moieties Az1-1 to Az1-5,

* is a portion connected to Formula 1 above,

Ar ₂ , Ar ₃ and R ₁ are each as defined in Formula 1 above.

According to another example, at least two of X ₁ to X ₃ may be N. That is, the X ₁ to X ₃ -containing ring moiety may be one of the moieties Az-3 to Az1-5. In the compound represented by Formula 1, X ₄ to X ₆ are the same or different from each other and are each independently N or C(R ₂ ), provided that at least one of X ₄ to X ₆ is N. At this time, if C(R ₂ ) is plural, the plurality of R ₂ are the same or different from each other. These X ₄ to X ₆ -containing ring moieties, like the X _{1 to} In this way, by including at least one nitrogen-containing heteroaromatic ring, the compound of Formula 1 according to the present invention may exhibit better electron absorption characteristics and be advantageous for electron injection and transport.

According to one example, the X ₄ to X ₆ -containing ring moiety ( moiety) may be any one of the following moieties Az2-1 to Az2-6, but is not limited thereto.

In the moieties Az2-1 to Az2-6,

* is a portion connected to Formula 1 above,

A plurality of R ₂ is the same as or different from each other,

R ₂ is as defined in Formula 1 above.

Here, R ₁ , R ₂ and Ar ₂ and Ar ₃ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, 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 ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C It is selected from the group consisting of an arylphosphine oxide group of ₆₀ , an arylamine group of C ₆ to C ₆₀ , an (aryl)(heteroaryl)amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. , specifically, each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C It may be selected from the group consisting of an aryl group having ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms.

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, and aryl group of R ₁ , R _{2 ,} Ar ₂ and Ar ₃ Silyl group, alkyl boron group, aryl boron group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine and heteroaryl amine group are each independent. Deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom Heterocycloalkyl group with 3 to 40 atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ ( Aryl) (heteroaryl) is substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, specifically deuterium, halogen, cyano group, C ₁ to C ₄₀ Alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkylphos. 1 selected from the group consisting of a pin group, a C ₆ to C ₆₀ arylphosphine group, a C ₁ to C ₄₀ alkylphosphine oxide group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group. It may be substituted or unsubstituted with more than one type of substituent. If the substituents are plural, they may be the same or different from each other.

In the compound represented by Formula 1, n1 and n2 are each integers from 0 to 4.

Here, when n1 and n2 are each 0, it means that L ₁ and L ₂ are each a single bond (direct bond). On the other hand, when n1 and n2 are each integers of 1 to 3, L ₁ and L ₂ are divalent linker groups, consisting of an arylene group of C ₆ to C ₃₀ and a heteroarylene group of 5 to 30 nuclear atoms. selected from the military. At this time, the plurality of L ₁ is the same as or different from each other, and the plurality of L ₂ are the same as or different from each other.

The L ₁ and L ₂ are the same as or different from each other, and are each independently selected from the group consisting of an arylene group of C ₆ to C ₃₀ and a heteroarylene group of 5 to 30 nuclear atoms, and specifically, each independently of C ₆ to It may be selected from the group consisting of a C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

The arylene group and heteroarylene group of L ₁ and L ₂ are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to 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 ~ C ₆₀ Aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C Substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group of ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. , specifically, each independently, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), C ₁ ~ C ₂₀ alkyl group, C ₃ ~ C ₂₀ Cycloalkyl group, heterocycloalkyl group with 3 to 20 nuclear atoms, C ₆ to C ₃₀ aryl group, C ₁ to C ₂₀ alkylphosphine oxide group, C ₆ to C ₃₀ arylphosphine oxide group, C ₆ to It may be substituted or unsubstituted with one or more substituents selected from the group consisting of C ₃₀ arylamine groups, and when the substituents are plural, they may be the same or different from each other.

According to one example, L ₁ and L ₂ may be the same or different from each other, and may each independently be a single bond or an arylene group of C ₆ to C ₁₈ , and the arylene group of L ₁ and L ₂ may be a deuterium (D) , halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), C ₁ ~ C ₂₀ alkyl group, C ₃ ~ C ₂₀ cycloalkyl group, nuclear atoms 3 to 20 Heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group, C ₁ ~ C ₂₀ alkylphosphine oxide group, C ₆ ~ C ₃₀ arylphosphine oxide group, C ₆ ~ C ₃₀ arylamine group selected from the group consisting of It may be substituted or unsubstituted with one or more types of substituents, and when the substituents are plural, they are the same or different from each other.

According to another example, one or more L ₁ and L ₂ are the same or different from each other, and are each independently a single bond, or a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, It may be selected from the group consisting of fluorene groups and combinations thereof. Here, the hydrogen of the phenylene group, biphenylene group, terphenylene group, naphthalene group, phenanthrene group, triphenylene group, and fluorene group is deuterium (D), halogen (e.g. -F, -Cl, -Br, -I etc.), cyano group (-CN), C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heteroaryl group having 5 to 10 nuclear atoms or is substituted with one or more substituents selected from the group consisting of (非)-Can be substituted.

According to another example, L ₁ and L ₂ may be the same or different from each other, and may each independently be a single bond, or may be selected from the group consisting of linker groups L1-1 to L1-3. However, it is not limited to this.

In the linker groups L1-1 to L1-3,

* refers to the part where a bond is formed with Formula 1,

b is an integer from 0 to 4,

One or more R are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino 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 with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to 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 ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C It may be selected from the group consisting of (aryl) (heteroaryl) amine groups of ₆ to C ₆₀ and heteroarylamine groups having 5 to 60 nuclear atoms, and specifically, each independently hydrogen, deuterium, halogen group, cyano group, and nitro group. group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl with 5 to 60 nuclear atoms. It may be selected from the group consisting of groups.

Depending on the introduction position of Ar ₁ and the types of L ₁ and L ₂ described above, the compound represented by Formula 1 may be a compound represented by any one of Formulas 4 to 39 below. However, it is not limited to this.

In Formulas 4 to 39,

Ar ₁ to Ar ₃ , R ₁ , R ₂ , n1 and n2 are each as defined in Formula 1 above.

It may be further specified as the following compounds A1 to C64 represented by Chemical Formula 1 according to the present invention described above, but is not limited thereto.

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

In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

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

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, and adamantine.

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, preferably 1 to 3 carbons in the ring, is N, O, S Or it is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a form in which two or more rings are condensed with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

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

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. In addition, “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

In the present invention, “alkyl boron group” refers to a boron group substituted with alkyl having 1 to 40 carbon atoms, and “aryl boron group” refers to a boron group substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “alkylphosphinyl group” refers to a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. Additionally, in the present invention, “arylphosphinyl group” refers to a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamine.

In the present invention, “heteroarylamine” refers to an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.

In the present invention, (aryl)(heteroaryl)amine refers to an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.

In the present invention, “condensed ring” refers to a condensed aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, It refers to a C ₃ to C ₆₀ spiro ring or a combination thereof.

In the present invention, “nuclear atom number” refers to the number of ring atoms constituting a ring structure, and the nuclear atom refers to carbon or a heteroatom selected from the group consisting of N, O, S, and Se. can do. For example, the number of nuclear atoms of pyridine is 6, including 5 C and 1 N that make up the pyridine ring.

<Organic electroluminescent device>

Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as 'organic EL device') containing the compound represented by the above-mentioned formula (1).

Specifically, the organic electroluminescent device according to the present invention, as shown in FIGS. 1 to 3, includes an anode 100, a cathode 200, and an electroluminescent device interposed between the anode and the cathode. It includes one or more organic layers 300, and at least one of the one or more organic layers includes the compound represented by Chemical Formula 1. At this time, the above compounds may be used alone, or two or more may be used in combination.

The one or more organic layer 300 may include one or more of a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and an electron injection layer 350, Optionally, an electron transport auxiliary layer 360 may be additionally included. At this time, at least one organic layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer containing the compound of Formula 1 may be the electron transport layer 340 or the electron transport auxiliary layer 360.

According to one example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes the compound represented by Formula 1 above. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer into the electron transport layer due to the compound of Formula 1, and can also quickly move from the electron transport layer to the light-emitting layer, so that the holes and electrons in the light-emitting layer The binding force is high. Therefore, the organic electroluminescent device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. In addition, the compound of Formula 1 has excellent thermal and electrochemical stability, and can improve the performance of organic electroluminescent devices.

The compound of Formula 1 may be used alone or mixed with electron transport layer materials known in the art.

In the present invention, electron transport layer materials that can be used interchangeably with the compound of Formula 1 include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene ( perylene)-based compounds, aluminum complexes (e.g. Alq _3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g. Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or two or more types can be used together.

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

According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes the compound represented by Formula 1. Includes. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. The compound represented by Formula 1 has high triplet energy. For this reason, when the compound of Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. Additionally, the compound of Formula 1 can prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer adjacent to the light-emitting layer. Accordingly, the number of excitons contributing to light emission in the light-emitting layer can be increased to improve the light-emitting efficiency of the device, and the durability and stability of the device can be improved to effectively increase the lifespan of the device.

The compound of Formula 1 may be used alone or mixed with materials for the electron transport layer auxiliary layer known in the art.

In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives (e.g. , BCP), heterocyclic derivatives containing nitrogen, etc., but are not limited thereto.

The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, the anode 100, one or more organic layer 300, and cathode 200 may be sequentially stacked on a substrate (FIGS. 1 to 1) 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

According to one example, as shown in FIG. 1, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and a cathode on a substrate. (200) may have a sequentially stacked structure. Optionally, as shown in FIG. 2, an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200. Additionally, an auxiliary electron transport layer 360 may be located between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3).

The organic electroluminescent device of the present invention contains a It can be manufactured by forming an organic material layer and an electrode using materials and methods known in the technical field.

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

The substrate that can be used in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

Additionally, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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 are not limited thereto.

Additionally, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

Additionally, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and common materials known in the art can be used.

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

[Preparation Example 1] - Synthesis of compound MM1

2-(3-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (100.0 g, 238.15 mmol), bis(pinacolato)diboron under nitrogen flow. (72.57 g, 285.78 mmol), PdCl ₂ (dppf) (5.83 g, 7.14 mmol), KOAc (98.14 g, 476.29 mmol), X-Phos (11.35g, 23.81 mmol) and 2000 ml of 1,4-dioxane were mixed and stirred at 110°C for 8 hours. After completion of the reaction, it was filtered with silica gel and Celite. After removing the solvent in the filtered organic layer, 103 g (yield: 85%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 472.35 g/mol, measured value: 472 g/mol)

[Preparation Example 2] - Synthesis of compound MM2

2-(2-chloro-4-(naphthalen-2-yl) instead of 2-(3-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine )phenyl)-4,6-diphenyl-1,3,5-triazine was performed in the same manner as in Preparation Example 1 to obtain 98 g (yield: 82%) of the target compound.

GC-Mass (theoretical value: 561.49 g/mol, measured value: 561 g/mol)

[Preparation Example 3] - Synthesis of compound MM3

1,2-dibromo-4-chlorobenzene (20.00 g, 73.98 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-1,3,5-triazine (70.85 g, 162.75 mmol), Pd(PPh ₃ ) ₄ (5.13 g, 4.44 mmol), K ₂ CO ₃ (51.12 g, 369.89 mmol), 1, 400 ml of 4-dioxane and 100 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 47 g (yield: 88%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 727.27 g/mol, measured value: 727 g/mol)

[Preparation Example 4] - Synthesis of compound MM4

Under nitrogen flow, (4-chloro-1,2-phenylene)diboronic acid (30.00 g, 149.86 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (88.26 g, 329.69 mmol), Pd (PPh ₃ ) ₄ (10.39 g, 8.99 mmol), K ₂ CO ₃ (103.56 g, 749.29 mmol), 400 ml of 1,4-dioxane, and 100 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 64 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 575.07 g/mol, measured value: 575 g/mol)

[Preparation Example 5] - Synthesis of compound MM5

Under nitrogen flow, (3-chloro-1,2-phenylene)diboronic acid (30.00 g, 149.86 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (88.26 g, 329.69 mmol), Pd (PPh ₃ ) ₄ (10.39 g, 8.99 mmol), K ₂ CO ₃ (103.56 g, 749.29 mmol), 400 ml of 1,4-dioxane, and 100 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 56 g (yield: 65%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 575.07 g/mol, measured value: 575 g/mol)

[Preparation Example 6] - Synthesis of compound MM6

1,2-dibromo-3-chlorobenzene (20.00 g, 73.98 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-1,3,5-triazine (70.85 g, 162.75 mmol), Pd(PPh ₃ ) ₄ (5.13 g, 4.44 mmol), K ₂ CO ₃ (51.12 g, 369.89 mmol), 1, 400 ml of 4-dioxane and 100 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 55 g (yield: 91%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 727.27 g/mol, measured value: 727 g/mol)

[Synthesis Example 1] - Synthesis of Compound A1

2-(3-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (20.00 g, 30.95 mmol), 2,4-diphenyl under nitrogen flow. -6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (10.37 g, 23.81 mmol), Pd(OAc ) ₂ (0.16 g, 0.71 mmol), Cs ₂ CO ₃ (15.52 g, 47.63 mmol), X-Phos (1.14g, 2.38 mmol), 200 ml of 1,4-dioxane and 50 ml of H ₂ O were mixed and It was stirred at ℃ for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 12 g (yield: 75%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 692.83 g/mol, measured value: 692 g/mol)

[Synthesis Example 2] - Synthesis of Compound A10

2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1 Instead, 2-(naphthalen-2-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3, The same process as Synthesis Example 1 was performed except for using 5-triazine, and 13 g (yield: 77%) of the target compound was obtained.

GC-Mass (theoretical value: 742.89 g/mol, measured value: 742 g/mol)

[Synthesis Example 3] - Synthesis of Compound A41

2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1 Instead, 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) The same process as Synthesis Example 1 was performed except for using phenyl)pyrimidine to obtain 14 g (yield: 80%) of the target compound.

GC-Mass (theoretical value: 767.94 g/mol, measured value: 767 g/mol)

[Synthesis Example 4] - Synthesis of Compound A51

2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1 Instead, 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl) 14 g (yield: 80%) of the target compound was obtained by performing the same process as Synthesis Example 1 except for using -1,3,5-triazine.

GC-Mass (theoretical value: 768.92 g/mol, measured value: 768 g/mol)

[Synthesis Example 5] - Synthesis of Compound C1

Compound MM1 (20.00 g, 39.11 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (11.52 g, 43.02 mmol), Pd(PPh ₃ ) ₄ synthesized in Preparation Example 1 under a nitrogen stream. (1.36 g, 1.17 mmol), K ₂ CO ₃ (16.21 g, 117.32 mmol), 200 ml of 1,4-dioxane, and 50 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 18 g (yield: 78%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 616.73 g/mol, measured value: 616 g/mol)

[Synthesis Example 6] - Synthesis of Compound A5

2-(2-chloro-4-(naphthalen-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.00 g, 42.56 mmol), 2,4-diphenyl-6 under nitrogen flow. -(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (18.53 g, 42.56 mmol), Pd(OAc) ₂ (0.19 g, 0.85 mmol), Cs ₂ CO ₃ (27.73 g, 85.11 mmol) _, It was stirred for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, 25 g (yield: 82%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 742.89 g/mol, measured value: 742 g/mol)

[Synthesis Example 7] - Synthesis of Compound C15

Compound MM2 (20.00 g, 35.62 mmol), 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (12.21 g, 35.62 mmol) synthesized in Preparation Example 2 under a nitrogen stream. , Pd(OAc) ₂ (0.16 g, 0.71 mmol), Cs ₂ CO ₃ (23.21 g, 71.24 mmol) _, were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 22 g (yield: 85%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 741.90 g/mol, measured value: 741 g/mol)

[Synthesis Example 8] - Synthesis of Compound C32

Compound MM3 (20.00 g, 27.50 mmol), naphthalen-1-ylboronic acid (4.73 g, 27.50 mmol), Pd(OAc) ₂ (0.12 g, 0.55 mmol), Cs ₂ CO ₃ synthesized in Preparation Example 3 under a nitrogen stream. (17.92 g, 55.00 mmol), X-Phos (0.52g, 1.10 mmol), 200 ml of 1,4-dioxane, and 50 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 17 g (yield: 79%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 818.98 g/mol, measured value: 818 g/mol)

[Synthesis Example 9] - Synthesis of Compound C33

The same process as Synthesis Example 8 was performed except that naphthalen-2-ylboronic acid was used instead of naphthalen-1-ylboronic acid used in Synthesis Example 8, and 18 g (yield: 82%) of the target compound was obtained.

GC-Mass (theoretical value: 768.92 g/mol, measured value: 768 g/mol)

[Synthesis Example 10] - Synthesis of Compound C34

17 g of the target compound (yield: 76 %) was obtained.

GC-Mass (theoretical value: 845.02 g/mol, measured value: 845 g/mol)

[Synthesis Example 11] - Synthesis of Compound C37

The same process as Synthesis Example 8 was performed except that (3-cyanophenyl)boronic acid was used instead of naphthalen-1-ylboronic acid used in Synthesis Example 8, and 17 g (yield: 81%) of the target compound was obtained.

GC-Mass (theoretical value: 793.93 g/mol, measured value: 793 g/mol)

[Synthesis Example 12] - Synthesis of Compound C36

The same process as Synthesis Example 8 was performed except that pyridin-3-ylboronic acid was used instead of naphthalen-1-ylboronic acid used in Synthesis Example 8, and 16 g (yield: 76%) of the target compound was obtained.

GC-Mass (theoretical value: 769.91 g/mol, measured value: 769 g/mol)

[Synthesis Example 13] - Synthesis of Compound C35

Compounds synthesized in Preparation Example 3 under nitrogen stream MM3 (20.00 g, 27.50 mmol), 9H-carbazole (4.60 g, 27.50 mmol), Pd ₂ (dba) ₃ (0.76 g, 0.83 mmol), P(t-Bu) ₃ (1.11 g, 5.50 mmol), NaO(t-Bu) (5.29g, 55.00 mmol) and 200 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 18 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 858.02 g/mol, measured value: 858 g/mol)

[Synthesis Example 14] - Synthesis of Compound C20

Compound MM4 (20.00 g, 34.78 mmol), [1,1'-biphenyl]-2-ylboronic acid (6.89 g, 34.78 mmol), Pd(OAc) ₂ (0.16 g, 0.70 mmol) synthesized in Preparation Example 4 under a nitrogen stream. mmol), Cs ₂ CO ₃ (22.66 g, 69.56 mmol) _, . After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 17 g (yield: 72%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 692.83 g/mol, measured value: 692 g/mol)

[Synthesis Example 15] - Synthesis of Compound C2

17 g of the target compound (yield: 75 %) was obtained.

GC-Mass (theoretical value: 666.79 g/mol, measured value: 666 g/mol)

[Synthesis Example 16] - Synthesis of Compound C4

The same process as Synthesis Example 14 was performed except that (3-cyanophenyl)boronic acid was used instead of [1,1'-biphenyl]-2-ylboronic acid used in Synthesis Example 14, and 17 g of the target compound (yield: 76%) was obtained.

GC-Mass (theoretical value: 641.74 g/mol, measured value: 641 g/mol)

[Synthesis Example 17] - Synthesis of Compound C7

17 g of the target compound (yield: 80 %) was obtained.

GC-Mass (theoretical value: 617.72 g/mol, measured value: 617 g/mol)

[Synthesis Example 18] - Synthesis of Compound C11

The same process as Synthesis Example 14 was performed except that (3-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of [1,1'-biphenyl]-2-ylboronic acid used in Synthesis Example 14. 21 g (yield: 85%) of the target compound was obtained.

GC-Mass (theoretical value: 781.92 g/mol, measured value: 781 g/mol)

[Synthesis Example 19] - Synthesis of Compound C12

The target compound was obtained by carrying out the same process as Synthesis Example 14, except that dibenzo[b,d]furan-4-ylboronic acid was used instead of [1,1'-biphenyl]-2-ylboronic acid used in Synthesis Example 14. 19 g (yield: 80%) was obtained.

GC-Mass (theoretical value: 706.81 g/mol, measured value: 706 g/mol)

[Synthesis Example 20] - Synthesis of Compound C13

The target compound was obtained by carrying out the same process as Synthesis Example 14, except that dibenzo[b,d]thiophen-4-ylboronic acid was used instead of [1,1'-biphenyl]-2-ylboronic acid used in Synthesis Example 14. 19 g (yield: 76%) was obtained.

GC-Mass (theoretical value: 722.87 g/mol, measured value: 722 g/mol)

[Synthesis Example 21] - Synthesis of Compound C21

Compound MM5 (20.00 g, 34.78 mmol), phenylboronic acid (4.24 g, 34.78 mmol), Pd(OAc) ₂ (0.16 g, 0.70 mmol), Cs ₂ CO ₃ (22.66 g, 69.56 mmol), X-Phos (0.66g, 1.39 mmol), 200 ml of 1,4-dioxane, and 50 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 17 g (yield: 78%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 616.73 g/mol, measured value: 616 g/mol)

[Synthesis Example 22] - Synthesis of Compound C23

The same process as Synthesis Example 21 was performed except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid used in Synthesis Example 14, and 18 g (yield: 80%) of the target compound was obtained.

GC-Mass (theoretical value: 666.79 g/mol, measured value: 666 g/mol)

[Synthesis Example 23] - Synthesis of compound C30-1

Compound MM5 (20.00 g, 34.78 mmol), 9H-carbazole (5.82 g, 34.78 mmol), Pd ₂ (dba) ₃ (0.96 g, 1.04 mmol), P(t-Bu) synthesized in Preparation Example 5 under a nitrogen stream. ₃ (1.41 g, 6.96 mmol), NaO(t-Bu) (6.69g, 69.56 mmol) and 200 ml of toluene were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 20 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 705.83 g/mol, measured value: 705 g/mol)

[Synthesis Example 24] - Synthesis of Compound C38

Compound MM6 (20.00 g, 27.50 mmol), phenylboronic acid (3.35 g, 27.50 mmol), Pd(OAc) ₂ (0.12 g, 0.55 mmol), Cs ₂ CO ₃ (17.92 g, 55.00 mmol), X-Phos (0.52g, 1.10 mmol), 200 ml of 1,4-dioxane, and 50 ml of H ₂ O were mixed and stirred at 110°C for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, 17 g (yield: 80%) of the target compound was obtained using column chromatography.

GC-Mass (theoretical value: 768.92 g/mol, measured value: 768 g/mol)

[Synthesis Example 25] - Synthesis of Compound C39

The same process as Synthesis Example 24 was performed except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid used in Synthesis Example 24, and 18 g (yield: 80%) of the target compound was obtained.

GC-Mass (theoretical value: 818.98 g/mol, measured value: 818 g/mol)

[Example 1] Fabrication of a blue organic electroluminescent device

Compound A1 synthesized in Synthesis Example 1 was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1200 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, HI + 2% HAT-CN6 (10 nm)/HI (140 nm)/EB (5 nm)/BH + 2% BD (20nm)/Compound A1 +Liq (1:1 ) (30 nm)/LiF (1 nm)/Al (100 nm) were stacked in that order to manufacture an organic electroluminescent device. At this time, the structures of HI, HAT-CN6, EB, BH, BD, and Liq used are respectively as follows.

[Examples 2 to 25] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the materials listed in Table 1 below were used instead of Compound A1, which was used as the electron transport layer material in Example 1.

[Comparative Examples 1 to 4] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET, HB2, ET-1, and ET-2 were used instead of Compound A1, which was used as the electron transport layer material in Example 1. . The structures of ET, HB2, ET-1, and ET-2 used at this time are respectively as follows.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 25 and Comparative Examples 1 to 4, the driving voltage, emission wavelength, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. It was.

Sample electron transport layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 A1 3.2 454 8.2 Example 2 A10 3.7 455 8.5 Example 3 A41 3.5 455 7.7 Example 4 A51 3.5 455 8.8 Example 5 C1 3.7 458 9.1 Example 6 A51 3.8 451 8.5 Example 7 C15 3.4 457 9.1 Example 8 C32 3.5 451 8.4 Example 9 C33 3.8 458 8.5 Example 10 C34 4 455 8.7 Example 11 C37 3.5 453 8.8 Example 12 C36 3.5 458 8.9 Example 13 C35 3.4 455 8.7 Example 14 C20 3.5 453 8.5 Example 15 C2 3.5 457 8.7 Example 16 C4 3.7 455 8.5 Example 17 C7 4 453 8.7 Example 18 C11 3.5 458 9.1 Example 19 C12 3.4 453 8.4 Example 20 C13 3.5 451 8.5 Example 21 C21 3.8 457 7.8 Example 22 C23 3.2 451 8.4 Example 23 C30-1 3.9 458 7.9 Example 24 C38 4.1 455 9.1 Example 25 C39 4.1 453 9 Comparative Example 1 ET 4.7 458 6.9 Comparative Example 2 HB2 5.2 454 6.5 Comparative Example 3 ET-1 5.5 452 7.1 Comparative Example 4 ET-2 4.8 455 6.8

As shown in Table 1, the organic electroluminescent devices of Examples 1 to 25 using the compounds of the present invention in the electron transport layer have lower driving voltage and lower driving voltage compared to the organic electroluminescent devices of Comparative Examples 1 to 4 using conventional electron transport layer materials. It was confirmed that it was excellent in terms of luminescence peak and current efficiency.

[Example 26] Fabrication of a blue organic electroluminescent device

Compound C11 synthesized in Synthesis Example 18 was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1200 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, HI + 2% HAT-CN6 (10 nm)/HI (140 nm)/EB (5 nm)/BH + 2% BD (20 nm)/Compound A1 (5 nm)/ET An organic electroluminescent device was manufactured by stacking + Liq (1:1) (30 nm)/LiF (1 nm)/Al (100 nm) in that order. The structures of HI, HAT-CN6, EB, BH, BD, and Liq used at this time are the same as those described in Example 1, and the structures of ET are the same as those described in Comparative Example 1, so they are omitted.

[Examples 27 to 33] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 26, except that the materials listed in Table 2 below were used instead of Compound C11, which was used as the electron transport auxiliary layer material in Example 26.

[Comparative Examples 5 to 8] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 26, except that HB1, HB2, HB3, and HB4 were used instead of compound C11, which was used as the electron transport auxiliary layer material in Example 26. The structures of HB1, HB2, HB3, and HB4 are respectively as follows.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 26 to 33 and Comparative Examples 5 to 8, the driving voltage, emission wavelength, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below. It was.

Sample Electron transport auxiliary layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 26 C11 4 454 7.9 Example 27 C12 3.9 455 8.1 Example 28 C13 4.5 456 8 Example 29 C21 3.9 459 6.9 Example 30 C23 4.1 452 8.1 Example 31 C30-1 4.2 454 8.3 Example 32 C38 4.4 455 7.7 Example 33 C39 5 455 7.5 Comparative Example 5 HB1 5.1 458 5.9 Comparative Example 6 HB2 5.2 454 5.5 Comparative Example 7 HB3 5.5 452 5.1 Comparative Example 8 HB4 6 455 4.8

As shown in Table 2, the organic electroluminescent devices of Examples 26 to 33 in which the compound of the present invention was used in the electron transport auxiliary layer were the organic electroluminescent devices of Comparative Examples 5 to 8 in which conventional materials were used in the electron transport auxiliary layer, respectively. It was confirmed that it was superior in terms of driving voltage, emission peak, and current efficiency.

100: anode, 200: cathode,
300: organic material layer, 310: hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer,
360: Electron transport auxiliary layer

Claims (9)

Compound represented by Formula 1:
[Formula 1]

(In Formula 1 above,
Ar ₁ is a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, or a heterocycle with 3 to 40 nuclear atoms. Alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphos Pin group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine selected from the group consisting of heteroarylamine groups having 5 to 60 nuclear atoms,
X ₁ to X _{3 are} the same or different from each other, and are each independently N or C(R ₁ ), provided that at least one of X ₁ to
X ₄ to X _{8 are} the same or different from each other and are each independently N or C(R ₂ ), provided that at least one of X ₄ to
R ₁ , R ₂ , Ar ₂ and Ar ₃ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl with 5 to 60 nuclear atoms 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 alkylboron group, C ₆ to C ₆₀ aryl boron group, C ₁ to C ₄₀ alkylphosphine group, C ₆ to C ₆₀ arylphosphine group, C ₁ to C ₄₀ alkylphosphine oxide group, C ₆ to C ₆₀ It is selected from the group consisting of an arylphosphine oxide group, an arylamine group of C ₆ to C ₆₀ , an (aryl)(heteroaryl)amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms,
n1 and n2 are each integers from 0 to 4,
L ₁ and L ₂ are the same as or different from each other, and are each independently selected from the group consisting of an arylene group of C ₆ to C ₃₀ and a heteroarylene group of 5 to 30 nuclear atoms,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, and arylsilyl group of Ar ₁ to Ar ₃ , R ₁ and R ₂ , alkyl boron group, aryl boron group, alkyl phosphine group, aryl phosphine group, alkyl phosphine oxide group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group and heteroaryl amine group; And the arylene group and heteroarylene group of L ₁ and L ₂ are each independently selected from deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to 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 ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C 40 alkylphosphine oxide group _, C ₆ ~ C ₆₀ arylphosphine oxide group, Substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ , and a heteroarylamine group having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same or different from each other). According to paragraph 1,
The compound represented by Formula 1 is represented by the following Formula 2 or 3:
[Formula 2]

[Formula 3]

(In Formulas 2 and 3 above,
X ₁ to X ₈ , Ar ₁ to Ar ₃ , n1, n2, L ₁ and L ₂ are each defined in clause 1). According to paragraph 1,
Ar ₁ is selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and heteroaryl group of Ar ₁ include a cyano group, a cycloalkyl group of C ₃ to C ₂₀ , a heterocycloalkyl group of 3 to 20 nuclear atoms, an aryl group of C ₆ to C ₃₀ , and a hetero group of 5 to 30 nuclear atoms. In the group consisting of an aryl group, a C ₁ ~ C ₂₀ alkylphosphine group, a C ₆ ~ C ₃₀ arylphosphine group, a C ₁ ~ C ₂₀ alkylphosphine oxide group, and a C ₆ ~ C ₃₀ arylphosphine oxide group A compound that is substituted or unsubstituted with one or more selected substituents. According to paragraph 1,
Ar ₁ is a compound selected from the group consisting of the following substituents S1-1 to S1-7:

(In the substituents S1-1 to S1-7,
Y ₁ is selected from the group consisting of O, S, N(R ₃ ) and C(R ₄ )(R ₅ ),
R ₃ to R ₅ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkylphosphine group, C ₆ ~ C ₆₀ arylphosphine group, C ₁ ~ C 40 alkylphosphine oxide group _, C ₆ ~ C ₆₀ arylphosphine oxide group, Selected from the group consisting of an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ and a heteroarylamine group having 5 to 60 nuclear atoms, or condensed with an adjacent group to form a condensed ring to form,
a1 is an integer from 0 to 5,
a2 is an integer from 0 to 4,
a3 is an integer from 0 to 7,
a4 is an integer from 0 to 8,
A plurality of R is the same or different from each other,
R is a cyano group, a cycloalkyl group of C ₃ to C ₂₀ , a heterocycloalkyl group of 3 to 20 nuclear atoms, an aryl group of C ₆ to C ₃₀ , a heteroaryl group of 5 to 30 nuclear atoms, C ₁ to C ₂₀ is selected from the group consisting of an alkylphosphine group, a C ₆ to C ₃₀ arylphosphine group, a C ₁ to C ₂₀ alkylphosphine oxide group, and a C ₆ to C ₃₀ arylphosphine oxide group). According to paragraph 1,
L ₁ and L ₂ are the same or different from each other, and are each independently a single bond, or a compound selected from the group consisting of linker groups L1-1 to L1-3:

(In the linker groups L1-1 to L1-3,
b is an integer from 0 to 4,
R is hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group. Period, 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 arylphos Pin group, C ₁ ~ C ₄₀ alkylphosphine oxide group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 nuclear atoms). According to paragraph 1,
The compound represented by Formula 1 is represented by any one of the following Formulas 4 to 39:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

(In Formulas 4 to 39,
Ar ₁ to Ar ₃ , R ₁ , R ₂ , n1 and n2 are each as defined in clause 1). According to paragraph 1,
The compound represented by Formula 1 is selected from the group consisting of the following compounds A1 to C64:


. anode; cathode; It includes one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 7. According to clause 8,
An organic electroluminescent device in which the organic layer containing the compound is an electron transport layer or an electron transport auxiliary layer.

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