KR20240105533A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

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

Description

Organic compounds and organic electroluminescent devices containing the same {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 specifically, 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, It relates to an organic electroluminescent device with improved characteristics such as driving 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 has a low refractive index that 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. The purpose is to provide

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,

X ₁ to X ₃ are N or C(R ₁ ), provided that at least one of X ₁ to X ₃ is N,

n1 to n3 are each integers from 0 to 3,

L ₁ to L ₃ are the same or different from each other, and are each independently a single bond or 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,

R ₁ and Ar ₁ to Ar ₃ 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 ~ 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 ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,

However, at least one of Ar ₁ to Ar ₃ is a substituent represented by the formula CY,

[Chemical formula CY]

In the above formula CY,

m1 is 0 or 1,

Rings Cy1 to Cy3 are the same or different from each other, and are each independently selected from the group consisting of 5- to 6-membered aromatic rings and 4- to 6-membered aliphatic rings, provided that one of rings Cy1 to Cy3 is 4-membered. It is selected from ~6-membered aliphatic rings,

n4 is an integer from 0 to 2,

L ₄ is a single bond, or is 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,

m2 is 0 or 1,

A is selected from the group consisting of a cyano group (-CN), an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms,

The arylene group and heteroarylene group of L ₁ to L ₄ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group of R ₁ and Ar ₁ to Ar ₃ , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group and heteroaryl amine group, and The aryl group and heteroaryl group of A are each independently 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 ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and nuclear atom Substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroarylamine groups, wherein 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 has a low refractive index and 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 one or more condensed polycyclic groups bonded directly to a nitrogen-containing heteroaromatic ring (e.g. azine) or through a linker group, wherein the condensed polycyclic group contains an aliphatic ring of 4 to 6 members, It is represented by the formula 1 above. These compounds have excellent carrier transport ability (e.g., electron injection and transport ability), electrochemical stability, and thermal stability, and can realize the characteristics of organic electroluminescent devices, such as high efficiency, long life, and low driving voltage characteristics of the device.

Specifically, in the compound represented by Formula 1, the nitrogen-containing heteroaromatic ring (eg, azine) is an electron withdrawing group (EWG) with high electron absorption. Such nitrogen-containing heteroaromatic rings can improve electron mobility and improve electron transport and injection properties of compounds. 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.

To these nitrogen-containing heteroaromatic rings, a condensed polycyclic group in which one or more (e.g., 1 to 3) rings are condensed is bonded directly or through a linker group (e.g., phenylene group, biphenylene group, naphthalene group, etc.). there is. The condensed polycyclic group is a hydrocarbon group having 7 to 14 carbon atoms formed by condensing 2 to 3 rings, and one of the rings is an aliphatic ring of 4 to 6 members. Because of the 4- to 6-membered aliphatic ring in this condensed polycyclic group, the compound of Formula 1 according to the present invention can have high triplet energy and wide band gap. In addition, the compound of the present invention can have a relatively bulky form compared to a condensed polycyclic group consisting of only an aromatic ring, which can reduce the refractive index when depositing the material and increase the electron density, thereby increasing electrochemical stability. You can. Therefore, when the compound of the present invention is applied as a material for an electron transport layer or an electron transport auxiliary layer, the light efficiency of the device can be improved.

In addition, the condensed polycyclic group includes a cyano group (-CN), an aryl group of C ₆ to C ₆₀ (e.g., phenyl group, biphenyl group, fluorene group, spiro[cyclohexane-fluorene] group, etc.), and the number of nuclear atoms. It may be unsubstituted or substituted with a substituent (A) selected from the group consisting of 5 to 60 heteroaryl groups (e.g., dibenzofuran group, dibenzothiophene group, carbazole group, etc.). Depending on the substituent (A), the compound of the present invention can have a symmetric or asymmetric structure, and has a high molecular weight, so it has a high glass transition temperature and excellent thermal stability.

As described above, the compound represented by Formula 1 of the present invention has a low refractive index and is excellent in electron transport ability, thermal stability, electrochemical stability, carrier transport ability, luminescence ability, etc., and is used as an organic material layer material of an organic electroluminescent device, specifically It can be used as a light-emitting layer material, an electron transport layer/injection layer material, an electron transport auxiliary layer material, and more specifically, an electron transport layer material and 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 according to the present invention, X ₁ to X ₃ are N or C(R ₁ ), 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 are the same or different from each other. These X ₁ to X ₃ containing-rings ( ) is a type of nitrogen (N)-containing heteroaromatic ring, and is a monocyclic heteroaryl group (eg, azine group) containing at least one nitrogen atom. As a result, the compound of Formula 1 according to the present invention exhibits better electron absorption properties and may be advantageous for electron injection and transport.

One or more R ₁ are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), and nitro group. (-NO ₂ ), amino group (-NH ₂ ), 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 ₆ ~ C ₆₀ arylphosphine group, C A group consisting of an arylphosphine oxide group of ₆ to C 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. It may be selected from or condensed with an adjacent group (e.g., R ₁ -R ₁ , R ₁ -L ₁ , R ₁ -L ₂ , R ₁ -L ₃ , etc.) to form a condensed ring. Here, the condensed ring is a C ₃ ~ C ₆₀ condensed aliphatic ring (specifically, a C ₃ ~ C ₃₀ condensed aliphatic ring), a C ₆ ~ C ₆₀ condensed aromatic ring (specifically, a C ₆ ~ C ₃₀ condensed ring) aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing one or more heteroatoms (e.g., N, O, S, Se, etc.) (specifically, a 5- to 30-membered ring containing one or more heteroatoms) It may be one or more types selected from the group consisting of a circular condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and a combination thereof.

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, arylboron group, Arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, and 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, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nuclear atom Heteroaryl group with numbers 5 to 60, 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 arylphosphine oxide group, C 6 ~ C 60} arylamine group , C ₆ ~ C ₆₀ It may be substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 nuclear atoms. At this time, when the substituents are plural, they are the same or different from each other.

According to one example, one or more R ₁ are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN ), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ to C ₂₀ alkyl group, C ₃ to C ₂₀ cycloalkyl group, heterocycloalkyl group with 3 to 20 nuclear atoms, C ₆ to C ₃₀ is selected from the group consisting of an aryl group, a heteroaryl group with 5 to 30 nuclear atoms, and an arylamine group with C ₆ to C ₃₀ , or an adjacent group (e.g., R ₁ -R ₁ , R ₁ -L ₁ , R ₁ -L ₂ , R ₁ -L ₃ , etc.) can be condensed to form a condensed ring, and the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group of R ₁ are each independently selected from deuterium, halogen, and cyanogroup. No group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₃ ~ C ₂₀ cycloalkyl group, heterocycloalkyl group with 3 to 30 nuclear atoms, C ₆ to C ₃₀ aryl group, hetero group with 5 to 30 nuclear atoms It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a C ₆ to C ₃₀ arylamine group. At this time, when the substituents are plural, they are the same or different from each other.

According to one example, The moiety may be any one of the following moieties Mo-1 to Mo-6, but is not limited thereto.

In the moieties Mo-1 to Mo-6,

* is a portion connected to Formula 1 above,

R ₁ is as defined in Formula 1 above.

In the compound represented by Formula 1 according to the present invention, Ar ₁ to Ar ₃ are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc. ), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), 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 ~ 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 ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and nuclear atom It may be selected from the group consisting of 5 to 60 heteroarylamine groups, or may be condensed with an adjacent group (e.g. Ar ₁ -L ₁ , Ar ₂ -L ₂ , Ar ₃ -L ₃ ) to form a condensed ring. .

However, at least one of Ar ₁ to Ar ₃ is a substituent represented by the formula CY below, and the others are as described above.

[Chemical formula CY]

In the above formula CY,

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

m1 is 0 or 1,

Rings Cy1 to Cy3 are the same or different from each other, and are each independently selected from the group consisting of a 5-membered to 6-membered aromatic ring and a 4- to 6-membered aliphatic ring,

However, one of rings Cy1 to Cy3 is selected from 4- to 6-membered aliphatic rings,

n4 is an integer from 0 to 2, specifically 0 or 1,

L ₄ is a single bond, or is 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 is specifically a single bond or an arylene group of C ₆ to C ₁₈ and selected from the group consisting of heteroarylene groups having 5 to 18 nuclear atoms,

m2 is 0 or 1,

A is selected from the group consisting of a cyano group (-CN), an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms,

The arylene group and heteroarylene group of L ₄ and the aryl group and heteroaryl group of A 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 ~ 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ It may be substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amine groups and heteroarylamine groups having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same or Different.

The substituent represented by the formula CY is a C ₇ to C ₁₄ condensed polycyclic group containing a 4 to 6 membered aliphatic ring. Because of the 4- to 6-membered aliphatic ring in the substituent, the compound of the present invention can have high triplet energy and wide band gap, and can have a relatively bulky form compared to polycyclic groups condensed only with aromatic rings. Therefore, the refractive index can be reduced when depositing the material, and the electron density can also be increased, thereby increasing electrochemical stability.

According to one example, the substituent represented by the formula CY may be a substituent represented by any one of the following formulas CY1 to CY5. However, it is not limited to this.

[Formula CY1]

[Formula CY2]

[Chemical formula CY3]

[Chemical formula CY4]

[Chemical formula CY5]

In the above formulas CY1 to CY5,

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

Ring Cy1 to ring Cy3, n4, L ₄ , m1 and m2 are each as defined in the formula CY above,

X ₄ to X ₆ are N or C(R ₄ ), provided that at least one of X ₄ to X ₆ is N,

Y ₁ is selected from the group consisting of S, O, N(R ₅ ) and C(R ₆ )(R ₇ ),

o1 is an integer from 0 to 7,

o2 is an integer from 0 to 8,

R ₂ to R ₇ , Ar ₄ to Ar ₆ 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 to C ₄₀ alkyl group, C ₂ to 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ It may be selected from the group consisting of (aryl)(heteroaryl)amine groups and heteroarylamine groups having 5 to 60 nuclear atoms, or may be condensed with adjacent groups (e.g., R ₆ -R ₇ ) to form a condensed ring. , specifically, R ₂ to R ₇ , Ar ₄ to Ar ₆ 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 to C ₂₀ alkyl group, C ₃ to In the group consisting of a C ₂₀ cycloalkyl group, a heterocycloalkyl group with 3 to 20 nuclear atoms, a C ₆ to C ₃₀ aryl group, a heteroaryl group with 5 to 30 nuclear atoms, and an arylamine group with C ₆ to C ₃₀ It may be selected or condensed with adjacent groups to form a condensed ring.

According to another example, in the substituent represented by the formula CY, The moiety may be selected from the group consisting of the following moieties CY1-1 to CY1-16. However, it is not limited to this.

In the moieties CY1-1 to CY1-16,

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

According to another example, at least one of Ar ₁ to Ar ₃ may be a substituent represented by the formula CY, and the remaining substituents may be selected from the group consisting of the following substituents S1-1 to S1-8. However, it is not limited to this.

In the substituents S1-1 to S1-8,

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

a is an integer from 0 to 5, specifically an integer from 0 to 2,

b is an integer from 0 to 9, specifically an integer from 0 to 2,

c is an integer from 0 to 7, specifically an integer from 0 to 2,

d is an integer from 0 to 8, specifically an integer from 0 to 2,

X ₇ to X _{9 are} the same or different from each other and are each independently N or C(R ₈ ), provided that at least one of X ₇ to

Y ₂ is selected from the group consisting of O, S, N(R ₉ ) and C(R ₁₀ ) (R ₁₁ ),

R ₈ to R ₁₁ and Ar ₇ to Ar ₁₀ 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 ~ 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ It may be selected from the group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be condensed with an adjacent group (e.g., R ₁₀ -R ₁₁ ) to form a condensed ring. .

Depending on the bonding position of the substituent represented by the above-mentioned formula CY, the compound represented by the formula 1 may be a compound represented by any one of the following formulas 2 to 4. However, it is not limited to this.

In Formulas 2 to 4,

_{X 1 to ​ ​ ​}

In the compound represented by Formula 1 according to the present invention, n1 to n3 are each an integer of 0 to 3.

Here, when n1 to n3 are each 0, it means that L ₁ to L ₃ are each a single bond (direct bond). On the other hand, when n1 to n3 are each an integer of 1 to 3, L ₁ to L ₃ are each a divalent linker group, an arylene group of C ₆ to C ₃₀ and a heteroarylene group of 5 to 30 nuclear atoms. It may be selected from the group consisting of, and specifically, from the group consisting of an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms. Here, one or more L ₁ , one or more L ₂ and one or more L ₃ may be the same or different from each other.

The arylene group of L ₁ to L ₃ and the heteroarylene group are each independently selected from deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group ( -NO ₂ ), amino group (-NH ₂ ), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkyl boron group, C ₆ ~C ₆₀ aryl boron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ In the group consisting of an arylphosphine oxide group of ~C ₆₀ , an arylamine group of C ₆ ~C ₆₀ , an (aryl)(heteroaryl)amine group of C ₆ ~C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. It may be substituted or unsubstituted with one or more selected substituents. At this time, when the substituents are plural, they are the same or different from each other.

According to one example, L ₁ to L ₃ 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, a carbazole group, and a dibenzo group. It may be selected from the group consisting of furan group, dibenzothiophene group, fluorene group, and combinations thereof. Here, the hydrogen of the phenylene group, biphenylene group, terphenylene group, naphthalene group, phenanthrene group, triphenylene group, carbazole group, dibenzofuran group, dibenzothiophene group, and fluorene group is deuterium (D), halogen. (Example: -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ ~ C ₁₂ alkyl group, C ₆ ~ It may be substituted or unsubstituted with one or more substituents selected from the group consisting of a C ₁₀ aryl group and a heteroaryl group having 5 to 10 nuclear atoms.

According to another example, L ₁ to L ₃ may be the same or different from each other, and may each independently be a single bond or a linker group selected from the group consisting of the following linker groups L1-1 to L1-7. However, it is not limited to this.

In the linker groups L1-1 to L1-7,

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

Y ₃ is selected from the group consisting of O, S, N (R ₁₃ ), C (R ₁₄ ) (R ₁₅ ),

q is an integer from 0 to 2,

e is an integer from 0 to 4,

f is an integer from 0 to 6,

g is an integer from 0 to 8,

h is an integer from 0 to 3,

i is an integer from 0 to 7,

R ₁₂ to R ₁₅ are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group ( -NO ₂ ), amino group (-NH ₂ ), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkyl boron group, C ₆ ~C ₆₀ aryl boron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ In the group consisting of an arylphosphine oxide group of ~C ₆₀ , an arylamine group of C ₆ ~C ₆₀ , an (aryl)(heteroaryl)amine group of C ₆ ~C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. Can be condensed with selected or adjacent groups (e.g. R ₁₂ -R ₁₂ , R ₁₂ -R ₁₃ , R ₁₂ -R ₁₄ , R ₁₂ -R ₁₅ , R ₁₄ -R ₁₅ , etc.) to form a condensed ring. Specifically, R ₁₂ to R ₁₅ are the same or different from each other, and each independently represents deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ to C ₂₀ alkyl group, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, and C ₆ to C ₃₀ aryl group. Can be selected from the group consisting of amine groups, or condensed with adjacent groups (e.g. R ₁₂ -R ₁₂ , R ₁₂ -R ₁₃ , R ₁₂ -R ₁₄ , R ₁₂ -R ₁₅ , R ₁₄ -R ₁₅ , etc.) Thus, a condensed ring can be formed.

According to another example, L ₁ to L ₃ 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 the following linker groups L2-1 to L2-21. However, it is not limited to this.

In the linker groups L2-1 to L2-21,

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

R ₁₃ to R ₁₅ are deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ) , 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 ~ 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 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 arylphosphine oxide group, C It is 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, and specifically, R ₁₃ to R ₁₅ are The same or different from each other, each independently deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (- NH ₂ ), C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, and C ₆ ~ C ₃₀ arylamine group.

Hydrogen of the above-mentioned linker groups L2-1 to L2-21 is deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), an amino group (-NH ₂ ), an alkyl group of C ₁ to C ₁₂ , an aryl group of C ₆ to C ₁₀ , and a heteroaryl group having 5 to 10 nuclear atoms. )-can be substituted.

The compound represented by Formula 1 may be embodied as a compound represented by any one of the following Formulas 5 to 20. However, it is not limited to this.

In Formulas 5 to 20,

_{X 1 to ​ ​ ​ ​}

X ₄ to X ₆ are N or C(R ₄ ), provided that at least one of X ₄ to X ₆ is N,

Y ₁ is selected from the group consisting of S, O, N(R ₅ ) and C(R ₆ )(R ₇ ),

X ₇ to X _{9 are} the same or different from each other and are each independently N or C(R ₈ ), provided that at least one of X ₇ to

Y ₂ is selected from the group consisting of O, S, N(R ₉ ) and C(R ₁₀ ) (R ₁₁ ),

a is an integer from 0 to 5,

c is an integer from 0 to 7,

d is an integer from 0 to 8,

o1 is an integer from 0 to 7,

o2 is an integer from 0 to 8,

R ₄ to R ₁₁ , Ar ₄ to Ar ₉ 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 ~ 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ It may be selected from the group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be condensed with an adjacent group to form a condensed ring.

The compound represented by Formula 1 according to the present invention described above may be further specified as the following compounds 1 to 120, 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.

<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 BB-1

2,4-dichloro-6-phenyl-1,3,5-triazine (30.0g, 132.7mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (46.9g, 132.7mmol), Pd(PPh ₃ ) ₄ (4.6g, 4.0mmol), and K ₂ CO ₃ (36.7g, 265.5mmol) were added to 600ml of Toluene, 150ml of EtOH, and 150ml of H ₂ O and incubated for 3 hours. It was heated, refluxed, and stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound BB-1 (22.5 g, yield 34%).

1H-NMR: δ 8.38-8.36 (m, 8H), 7.94 (s, 1H), 7.73 (t, 1H), 7.50-7.48 (m, 9H)

Mass : [(M+H) ⁺ ] : 500

[Preparation Example 2] Synthesis of compound BB-2

2,4-dichloro-6-phenyl-1,3,5-triazine (30.0g, 132.7mmol), (3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[ 1,1'-biphenyl]-3-yl)boronic acid (57.0g, 132.7mmol), Pd(PPh ₃ ) ₄ (4.6g, 4.0mmol), and K ₂ CO ₃ (36.7g, 265.5mmol) were mixed with Toluene. It was added to 600ml, 150ml of EtOH, and 150ml of H ₂ O, heated, refluxed, and stirred for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound BB-2 (21.4 g, yield 28%).

1H-NMR: δ 8.38-8.36 (m, 8H), 7.94 (s, 2H), 7.73 (t, 2H), 7.61 (d, 2H), 7.50-7.48 (m, 9H)

Mass : [(M+H) ⁺ ] : 576

[Preparation Example 3] Synthesis of compound BB-3

2,4,6-trichloro-1,3,5-triazine (52.2g, 283.0mmol), dibenzo[b,d]furan-1-ylboronic acid (20.0g, 94.3mmol), Pd(PPh ₃ ) ₄ ( 3.3g, 2.8mmol), and K ₂ CO ₃ (26.1g, 188.7mmol) were added to 600ml of Toluene, 150ml of EtOH, and 150ml of H ₂ O and heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound BB-3 (11.9 g, yield 40%).

1H-NMR: δ 7.98(d, 1H), 7.82(d, 1H), 7.69(d, 1H), 7.57-7.54(m, 2H), 7.39(t, 1H), 7.31(t, 1H)

Mass : [(M+H) ⁺ ] : 317

[Preparation Example 4] Synthesis of compound BB-4

2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (30.0g, 71.0mmol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (16.9g, 71.0mmol), Pd(PPh ₃ ) ₄ (2.5g, 2.1mmol), and K ₂ CO ₃ (19.6g, 141.9mmol) were added to 600ml of Toluene, 150ml of EtOH, and 150ml of H ₂ O for 3 hours. It was heated, refluxed, and stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound BB-4 (20.5 g, yield 54%).

1H-NMR: δ 8.36(d, 4H), 8.12(s, 1H), 8.07(s, 1H), 7.90-7.88(m, 2H), 7.82-7.78(m, 2H), 7.55(d, 1H) , 7.50(m, 6H), 7.38(t, 1H), 7.28(t, 1H)

Mass : [(M+H) ⁺ ] : 537

[Synthesis Example 1] Synthesis of Compound 2

Compound BB-1 (10.0g, 20.0mmol), (5,6,7,8-tetrahydronaphthalen-1-yl)boronic acid (3.5g, 20.0mmol), Pd(PPh ₃ ) ₄ ( 0.7g, 0.6mmol) and K ₂ CO ₃ (5.5g, 40.1mmol) were added to 240ml of Dioxane and 60ml of H ₂ O, heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 2 (4.1 g, yield 34%).

Mass : [(M+H) ⁺ ] : 596

[Synthesis Example 2] Synthesis of Compound 5

(5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

Compound BB-2 (10.0g, 17.4mmol), (5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid (3.1g, 17.4mmol), Pd(PPh ₃ ) ₄ ( 0.6g, 0.5mmol) and K ₂ CO ₃ (4.8g, 34.8mmol) were added to 240ml of Dioxane and 60ml of H ₂ O, heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 5 (4.2 g, yield 36%).

Mass : [(M+H) ⁺ ] : 672

[Synthesis Example 3] Synthesis of Compound 15

Compound BB-3 (10.0g, 31.6mmol), (5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid (11.1g, 63.3mmol), Pd(PPh ₃ ) ₄ ( 2.2g, 1.8mmol) and K ₂ CO ₃ (8.7g, 63.3mmol) were added to 200ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 15 (5.3 g, yield 33%).

Mass : [(M+H) ⁺ ] : 509

[Synthesis Example 4] Synthesis of Compound 37

Compound BB-4 (10.0g, 18.7mmol), bicyclo[4.2.0]octa-1(6),2,4-trien-3-ylboronic acid (2.8g, 18.7mmol), Pd synthesized in Preparation Example 4 (OAc) ₂ (0.1g, 0.6mmol), XPhos (0.5g, 1.1mmol), and Cs ₂ CO ₃ (12.2g, 37.3mmol) were added to 200ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O, and incubated for 3 hours. It was heated, refluxed, and stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 37 (4.3 g, yield 38%).

Mass : [(M+H) ⁺ ] : 605

[Synthesis Example 5] Synthesis of Compound 42

Compound BB-1 (10.0g, 20.0mmol), (5,6,7,8-tetrahydroanthracen-2-yl)boronic acid (4.5g, 20.0mmol), Pd(PPh ₃ ) ₄ ( 0.7g, 0.6mmol) and K ₂ CO ₃ (5.5g, 40.1mmol) were added to 240ml of Dioxane and 60ml of H ₂ O, heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 42 (4.4 g, yield 34%).

Mass : [(M+H) ⁺ ] : 646

[Synthesis Example 6] Synthesis of Compound 45

Compound BB-2 (10.0g, 17.4mmol), (9,10-dihydroanthracen-1-yl)boronic acid (3.9g, 17.4mmol), Pd(PPh ₃ ) ₄ (0.6g, 0.5) synthesized in Preparation Example 2 mmol), K ₂ CO ₃ (4.8 g, 34.8 mmol) was added to 240 ml of Dioxane and 60 ml of H ₂ O and heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 45 (4.1 g, yield 33%).

Mass : [(M+H) ⁺ ] : 720

[Synthesis Example 7] Synthesis of Compound 55

Compound BB-3 (10.0g, 31.6mmol), (9,10-dihydroanthracen-1-yl)boronic acid (14.2g, 63.3mmol), Pd(PPh ₃ ) ₄ (2.2g, 1.8) synthesized in Preparation Example 3 mmol), K ₂ CO ₃ (8.7 g, 63.3 mmol) was added to 200 ml of Toluene, 50 ml of EtOH, and 50 ml of H ₂ O, and heated to reflux and stirred for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 55 (5.9 g, yield 31%).

Mass : [(M+H) ⁺ ] : 605

[Synthesis Example 8] Synthesis of Compound 77

Compound BB-4 (10.0g, 18.7mmol), (5,6,7,8-tetrahydroanthracen-2-yl)boronic acid (4.2g, 18.7mmol), Pd(OAc) ₂ (0.1) synthesized in Preparation Example 4 g, 0.6 mmol), XPhos (0.5 g, 1.1 mmol), and Cs ₂ CO ₃ (12.2 g, 37.3 mmol) were added to 200 ml of Toluene, 50 ml of EtOH, and 50 ml of H ₂ O, and heated to reflux and stirred for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 77 (3.9 g, yield 31%).

Mass : [(M+H) ⁺ ] : 683

[Synthesis Example 9] Synthesis of Compound 82

Compound BB-1 (10.0g, 20.0mmol), (5,6,7,8-tetrahydrophenanthren-3-yl)boronic acid (4.5g, 20.0mmol), Pd(PPh ₃ ) ₄ ( 0.7g, 0.6mmol), and K ₂ CO ₃ (5.5g, 40.1mmol) were added to 240ml of Dioxane and 60ml of H ₂ O, heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 82 (4.1 g, yield 32%).

Mass : [(M+H) ⁺ ] : 646

[Synthesis Example 10] Synthesis of Compound 85

Compound BB-2 (10.0g, 17.4mmol), (5,6,7,8-tetrahydrophenanthren-9-yl)boronic acid (3.9g, 17.4mmol), Pd(PPh ₃ ) ₄ ( 0.6g, 0.5mmol), and K ₂ CO ₃ (4.8g, 34.8mmol) were added to 240ml of Dioxane and 60ml of H ₂ O, heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 85 (4.5 g, yield 36%).

Mass : [(M+H) ⁺ ] : 722

[Synthesis Example 11] Synthesis of Compound 95

Compound BB-3 (10.0g, 31.6mmol), (5,6,7,8-tetrahydrophenanthren-2-yl)boronic acid (12.5g, 63.3mmol), Pd(PPh ₃ ) ₄ ( 2.2g, 1.8mmol), and K ₂ CO ₃ (8.7g, 63.3mmol) were added to 200ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated and refluxed for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 95 (7.0 g, yield 34%).

Mass : [(M+H) ⁺ ] : 609

[Synthesis Example 12] Synthesis of Compound 117

Compound BB-4 (10.0g, 18.7mmol), (1,2-dihydrocyclobuta[a]naphthalen-7-yl)boronic acid (3.7g, 18.7mmol), Pd(OAc) ₂ (0.1) synthesized in Preparation Example 4 g, 0.6 mmol), XPhos (0.5 g, 1.1 mmol), and Cs ₂ CO ₃ (12.2 g, 37.3 mmol) were added to 200 ml of Toluene, 50 ml of EtOH, and 50 ml of H ₂ O, and heated to reflux and stirred for 3 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 117 (3.8 g, yield 31%).

Mass : [(M+H) ⁺ ] : 655

[Example 1] Fabrication of a blue organic electroluminescent device

Compound 2 synthesized in Synthesis Example 1 was purified by 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 2 + Liq (1:1 ) (30 nm)/LiF (1 nm)/Al (100 nm) were stacked in that order to manufacture an organic electroluminescent device. The structures of HI, HAT-CN6, EB, BH, BD, and Liq used at this time are as follows.

[Examples 2 to 12]

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 2, which was used as the electron transport layer material in Example 1.

[Comparative Examples 1 to 5] Preparation of blue organic electroluminescent device

Same as Example 1, except that Alq ₃ , Compound DA-1, Compound DA-2, Compound DA-3, and Compound DA-4 were used instead of Compound 2, which was used as the electron transport layer material in Example 1. A blue organic electroluminescent device was manufactured by performing this procedure. The structures of Alq ₃ , Compound DA-1, Compound DA-2, Compound DA-3, and Compound DA-4 used at this time are as follows.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 14 and Comparative Examples 1 to 5, 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 compound 2 3.3 455 8.2 Example 2 Compound 5 3.2 454 8.1 Example 3 Compound 15 3.3 455 8.3 Example 4 Compound 37 3.4 454 8.2 Example 5 Compound 42 3.2 455 8.0 Example 6 Compound 45 3.2 454 8.1 Example 7 Compound 55 3.3 455 8.0 Example 8 Compound 77 3.3 455 8.2 Example 9 compound 82 3.2 454 8.1 Example 10 Compound 85 3.2 455 8.0 Example 11 Compound 95 3.3 454 8.0 Example 12 Compound 117 3.4 455 8.1 Comparative Example 1 Alq ₃ 4.6 457 5.4 Comparative Example 2 Compound DA-1 4.0 460 6.8 Comparative Example 3 Compound DA-2 3.7 458 7.0 Comparative Example 4 Compound DA-3 4.6 4578 6.9 Comparative Example 5 Compound DA-4 4.5 459 7.2

As shown in Table 1, the organic electroluminescent devices of Examples 1 to 12 using the compound of the present invention in the electron transport layer were conventional electron transport layer materials (e.g. Alq ₃ ) or 4- to 6-membered aliphatic ring-ratio (non-). ) is superior in terms of driving voltage, emission peak, and current efficiency compared to the organic electroluminescent devices of Comparative Examples 1 to 5 using compounds containing condensed polycyclic groups (e.g., compounds DA-1 to DA-4) in the electron transport layer. could be confirmed.

[Example 13] Fabrication of a blue organic electroluminescent device

Compound 2 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 (20 nm)/Compound 2 (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 as follows.

[Examples 14 to 24] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that the electron transport auxiliary layer materials listed in Table 2 below were used instead of Compound 2 used as the electron transport auxiliary layer material in Example 13. .

[Comparative Example 6]

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that the electron transport auxiliary layer formed of Compound 2 in Example 13 was not included.

[Comparative Examples 7 to 10] Preparation of blue organic electroluminescent device

Proceed in the same manner as Example 13, except that Compound DA-1, Compound DA-2, Compound DA-3, and Compound DA-4 were used instead of Compound 2, which was used as the electron transport auxiliary layer material in Example 13. A blue organic electroluminescent device was manufactured. The structures of DA-1, DA-2, DA-3, and DA-4 used at this time are as follows.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 2 to 28 and Comparative Examples 6 to 10, 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 13 compound 2 3.2 455 8.3 Example 14 Compound 5 3.0 454 8.2 Example 15 Compound 15 3.1 455 8.3 Example 16 Compound 37 3.0 454 8.1 Example 17 Compound 42 3.2 453 8.3 Example 18 Compound 45 3.1 455 8.0 Example 19 Compound 55 3.1 455 8.1 Example 20 Compound 77 3.3 455 8.1 Example 21 Compound 82 3.2 454 8.0 Example 22 Compound 85 3.3 454 8.1 Example 23 Compound 95 3.3 456 8.0 Example 24 Compound 117 3.4 455 8.0 Comparative Example 6 - 4.6 455 6.3 Comparative Example 7 DA-1 3.9 454 6.9 Comparative Example 8 DA-2 4.2 456 6.9 Comparative Example 9 DA-3 4.4 455 6.7 Comparative Example 10 DA-4 4.1 455 6.9

As shown in Table 2, the organic light-emitting devices of Examples 13 to 24 using the compound of the present invention in the electron transport auxiliary layer are the organic electroluminescent devices of Comparative Example 6 or 4 to 6 that do not include the electron transport auxiliary layer. Driving voltage compared to the organic electroluminescent devices of Comparative Examples 7 to 10 using a compound containing a circular aliphatic ring-non-containing condensed polycyclic group (dP: compounds DA-1 to DA-4) in the electron transport auxiliary layer. , it was confirmed that it was superior in terms of luminescence 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 (11)

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

(In Formula 1 above,
X ₁ to X ₃ are N or C(R ₁ ), provided that at least one of X ₁ to X ₃ is N,
n1 to n3 are each integers from 0 to 3,
L ₁ to L ₃ are the same or different from each other, and are each independently a single bond or 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,
R ₁ and Ar ₁ to Ar ₃ 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 ~ 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 ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,
However, at least one of Ar ₁ to Ar ₃ is a substituent represented by the formula CY,
[Chemical formula CY]

In the above formula CY,
m1 is 0 or 1,
Rings Cy1 to Cy3 are the same or different from each other, and are each independently selected from the group consisting of 5- to 6-membered aromatic rings and 4- to 6-membered aliphatic rings, provided that one of rings Cy1 to Cy3 is 4-membered. It is selected from ~6-membered aliphatic rings,
n4 is an integer from 0 to 2,
L ₄ is a single bond, or is 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,
m2 is 0 or 1,
A is selected from the group consisting of a cyano group (-CN), an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms,
The arylene group and heteroarylene group of L ₁ to L ₄ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group of R ₁ and Ar ₁ to Ar ₃ , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group and heteroaryl amine group, and The aryl group and heteroaryl group of A are each independently 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 ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and nuclear atom Substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroarylamine groups, wherein 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 any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

(In Formulas 2 to 4,
_{X 1 to ​ ​ ​} According to paragraph 1,
A compound represented by the formula CY is a substituent represented by any one of the following formulas CY1 to CY5:
[Formula CY1]

[Formula CY2]

[Chemical formula CY3]

[Chemical formula CY4]

[Chemical formula CY5]

(In the above formulas CY1 to CY5,
Ring Cy1 to ring Cy3, n4, L ₄ and m1 to m2 are each as defined in claim 1,
X ₄ to X ₆ are N or C(R ₄ ), provided that at least one of X ₄ to X ₆ is N,
Y ₁ is selected from the group consisting of S, O, N(R ₅ ) and C(R ₆ )(R ₇ ),
o1 is an integer from 0 to 7,
o2 is an integer from 0 to 8,
R ₂ to R ₇ , Ar ₄ to Ar ₆ 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 to C ₄₀ alkyl group, C ₂ to 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl)(heteroaryl)amine group and heteroarylamine group having 5 to 60 nuclear atoms, or condensed with adjacent groups to form a condensed ring). According to paragraph 1,
In the substituent represented by the formula CY, A compound wherein the moiety is selected from the group consisting of the following moieties CY1-1 to CY1-16:
. According to paragraph 1,
At least one of Ar ₁ to Ar ₃ is a substituent represented by the formula CY, and the others are selected from the group consisting of the following substituents S1-1 to S1-8:

(In the substituents S1-1 to S1-8,
a is an integer from 0 to 5,
b is an integer from 0 to 9,
c is an integer from 0 to 7,
d is an integer from 0 to 8,
X ₇ to X _{9 are} the same or different from each other and are each independently N or C(R ₈ ), provided that at least one of X ₇ to
Y ₂ is selected from the group consisting of O, S, N(R ₉ ) and C(R ₁₀ ) (R ₁₁ ),
R ₈ to R ₁₁ and Ar ₇ to Ar ₁₀ 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 ~ 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl)(heteroaryl)amine group and heteroarylamine group having 5 to 60 nuclear atoms, or condensed with adjacent groups to form a condensed ring). According to paragraph 1,
L ₁ to L ₃ are the same or different from each other, and are each independently a single bond, or a compound selected from the group consisting of the following linker groups L1-1 to L1-7:

(In the linker groups L1-1 to L1-7,
Y ₃ is selected from the group consisting of O, S, N (R ₁₃ ), C (R ₁₄ ) (R ₁₅ ),
q is an integer from 0 to 2,
e is an integer from 0 to 4,
f is an integer from 0 to 6,
g is an integer from 0 to 8,
h is an integer from 0 to 3,
i is an integer from 0 to 7,
R ₁₂ to R ₁₅ are the same or different from each other, and are each independently 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 ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) selected from the group consisting of amine groups and heteroarylamine groups 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 5 to 15:
[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

(In Formulas 5 to 15,
_{X 1 to ​ ​ ​}
X ₇ to X _{9 are} the same or different from each other and are each independently N or C(R ₈ ), provided that at least one of X ₇ to
Y ₂ is selected from the group consisting of O, S, N(R ₉ ) and C(R ₁₀ ) (R ₁₁ ),
a is an integer from 0 to 5,
c is an integer from 0 to 7,
d is an integer from 0 to 8,
R ₈ to R ₁₁ , Ar ₇ to Ar ₉ 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 ~ 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl)(heteroaryl)amine group and heteroarylamine group having 5 to 60 nuclear atoms, or condensed with adjacent groups to form a condensed ring). According to paragraph 1,
The compound represented by Formula 1 is represented by any one of the following Formulas 16 to 20:
[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

(In Formulas 16 to 20,
_{X 1 to ​ ​ ​ ​}
X ₄ to X ₆ are N or C(R ₄ ), provided that at least one of X ₄ to X ₆ is N,
Y ₁ is selected from the group consisting of S, O, N(R ₅ ) and C(R ₆ )(R ₇ ),
o1 is an integer from 0 to 7,
o2 is an integer from 0 to 8,
R ₄ to R ₇ , Ar ₄ and Ar ₅ 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 to C ₄₀ alkyl group, C ₂ to 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 ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl)(heteroaryl)amine group and heteroarylamine group having 5 to 60 nuclear atoms, or condensed with adjacent groups to form a condensed ring). According to paragraph 1,
The compound represented by Formula 1 is selected from the group consisting of the following compounds 1 to 120:




. 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 9. According to clause 10,
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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