KR102611312B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

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 carrier transport ability, luminescence ability, electrochemical stability, and thermal stability, and luminous efficiency by including the same in one or more organic material layers. This is about an organic electroluminescent device with improved characteristics such as 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 containing the same. More specifically, it relates to a compound having excellent electron transport ability, luminescence performance, and thermal stability, and including the same in one or more organic layers to improve luminous efficiency, driving voltage, and lifespan. It relates to an organic electroluminescent device with improved properties such as.

When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as 'organic EL device'), holes are injected from the anode and electrons are injected from the cathode into the organic material layer. 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.

Materials for forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials depending on the color of the light. In addition, yellow and orange luminescent materials are also used as luminescent materials to realize 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. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

To date, hole injection layer and hole transport layer. As hole blocking layers and electron transport layers, NPB, BCP, and Alq ₃ expressed by the following chemical formulas are widely known, and as light emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. In particular, among light emitting materials, phosphorescent materials that have great advantages in terms of improving efficiency include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _{2 ,} etc., which are used as blue, green, and red dopant materials. It is being used as. To date, CBP has shown excellent properties as a phosphorescent host material.

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

The present invention provides a novel compound that has improved electron injection and transport capabilities, excellent thermal stability and luminescence performance, and can be used as an organic layer material of an organic electroluminescent device, specifically a light-emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material. The purpose is to

Another object of the present invention is to provide an organic electroluminescent device with low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compound described above.

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 and Ar ₂ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazo Hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycle with 3 to 60 nuclear atoms Alkyl group, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group,

n ₁ and n ₂ are each integers from 0 to 2,

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 60 nuclear atoms,

R ₁ and R ₂ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazo Hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycle with 3 to 60 nuclear atoms Alkyl group, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group,

The arylene group and heteroarylene group of L ₁ and L ₂ , and the hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, and heterocycloalkyl group of Ar ₁ , Ar ₂ , R ₁ and R ₂ , cycloalkenyl group, heterocycloalkenyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group. And the arylamine group is each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ to C ₆₀ alkyl group, C ₂ to C ₆₀ alkenyl group, C ₂ to C ₆₀ alkynyl group, C ₃ to C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ to C ₆₀ cycloalke Nyl group, heterocycloalkenyl group of 3 to 60 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 ₆₀ , C ₆ to C ₆₀ of Aryloxy group, C ₁ ~ C ₆₀ 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 It is substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group. In this case, when the substituents are plural, they are mutually same or different).

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, wherein at least one of the one or more organic material layers includes the above-described organic compound.

The organic material layer containing the organic compound may be at least one selected from the group consisting of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

The compound of the present invention has excellent heat resistance, carrier transport ability, luminescence ability, electrochemical stability, etc., so 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 at least one of a phosphorescent host material, an electron transport layer material, and an electron transport auxiliary layer material, it has excellent luminous performance, low driving voltage, high efficiency, fast mobility, and long lifespan compared to conventional materials. It is possible to manufacture an organic electroluminescent device having a , and furthermore, a full-color display panel with improved performance and lifespan can also be manufactured.

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 organic compounds>

The present invention is a novel compound that can be used as a high-efficiency light-emitting layer material (specifically, host), electron transport layer material, or electron transport auxiliary layer material of an organic electroluminescent device with electron injection and transport ability, luminescence ability, electrochemical stability, and thermal stability. provides.

Specifically, the compound represented by Formula 1 has a [1,2,4]triazolo[1,5-a]pyridine moiety ([1 ,2,4]triazolo[1,5-a]pyrindine moiety) and a phosphineoxide moiety are combined directly or through a linker group. Here, the carbon position number of anthracene can be expressed as follows.

The present invention introduces (substitutes) phosphine oxide and 1,2,4]triazolo[1,5-a]pyridine moieties at the 9th and 10th carbon positions of the anthracene moiety, respectively, to form a core anthracene moiety. By controlling the reactive site, molecular structural stability can be secured. In addition, by controlling the reaction site of the anthracene moiety, the stress of the molecular structure caused by injection of carriers during operation of the device can be minimized and the long lifespan of the device can be secured.

As described above, the compound represented by Formula 1 has excellent luminescence ability, electron injection, and transport ability. Therefore, the compound of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably as a light-emitting layer material (particularly, a phosphorescent host material of the light-emitting layer) or an electron transport layer material. In addition, because the compound of Formula 1 has high triplet energy, it can be used as a material for an auxiliary layer (hereinafter referred to as 'electron transport auxiliary layer') sandwiched between the light-emitting layer and the electron transport layer. In particular, when the compound of Formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material, the light emission and current efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. In addition, the compound of Formula 1 contributes to light emission within the light-emitting layer because it can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer adjacent to the light-emitting layer or holes that have reached the light-emitting layer from diffusing into the electron transport layer. By increasing the number of excitons, the luminous efficiency of the device can be improved, and the durability and stability of the device can be improved, effectively increasing the lifespan of the device. In addition, since the organic electroluminescent device containing the compound of Formula 1 can be driven at low voltage, the lifespan of the device can be improved. Full-color organic light emitting panels using these organic electroluminescent devices can also maximize performance.

In the compound represented by Formula 1 according to the present invention, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents hydrogen, deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, and amidino group (amidino group). group), hydrazino group, hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, cycloalkenyl group of C ₃ to C ₆₀ , heterocycloalkenyl group of 3 to 60 nuclear atoms, aryl group of C ₆ to C ₆₀ nuclear atoms, 5 nuclear atoms to 60 heteroaryl groups, C ₁ ~ C ₆₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ A group consisting of an alkyl boron group of C ₄₀ , _an aryl boron group of C ₆ ~ C ₆₀ , an arylphosphine group of C ₆ ~ C ₆₀ , an arylphosphine oxide group of C 6 ~ C ₆₀ , and an arylamine group of C ₆ ~ C ₆₀ is selected from

According to one example, Ar ₁ and Ar ₂ may be the same or different from each other, and may each independently be hydrogen or a C ₆ to C ₃₀ aryl group. Here, when Ar ₁ and Ar ₂ are each an aryl group of C ₆ to C ₃₀ , exciton reduction due to intermolecular stacking during deposition can be minimized, thereby improving the lifespan characteristics and efficiency of the device. Meanwhile, when Ar ₁ and Ar ₂ are hydrogen, they can be deposited at a relatively low temperature by controlling the sublimation temperature by adjusting the molecular weight.

According to another example, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently hydrogen, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, anthryl group, naphtha. It may be selected from the group consisting of cenyl group, pyrenel group, and chrysenyl group.

Ar ₁ and Ar ₂ hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl group, aryl group, heteroaryl group, alkyloxy group, Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, and amino group. , amidino group, hydrazino group, hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group , C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, aryl with C ₆ ~ C ₆₀ group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₆₀ alkylsilyl group, C ₆ to C ₆₀ aryl Silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when the substituents are plural, they are the same or different from each other.

Depending on Ar ₁ and Ar ₂ , the compound represented by Formula 1 may be a compound represented by any one of Formulas 2 to 5 below, but is not limited thereto.

In Formulas 2 to 5,

n ₁ , n ₂ , L ₁ , L ₂ , R ₁ and R ₂ are each as defined in Formula 1 above.

In the compound represented by Formula 1 according to the present invention, n ₁ and n ₂ are each integers of 0 to 2. Here, when n ₁ is 0, L ₁ is a direct bond (single bond), while when n ₁ is 1 or 2, L ₁ is a divalent linker, and a plurality of L ₁ is They are the same or different from each other, and are each independently selected from the group consisting of an arylene group having C ₆ to C ₃₀ and a heteroarylene group having 5 to 60 nuclear atoms. On the other hand, when n ₂ is 0, L ₂ is a direct bond (single bond), and on the other hand, when n ₂ is 1 or 2, L ₂ is a divalent linker, and a plurality of L ₁ is They are the same or different from each other, and are each independently selected from the group consisting of an arylene group having C ₆ to C ₃₀ and a heteroarylene group having 5 to 60 nuclear atoms. At this time, L ₁ and L ₂ may be the same or different from each other.

The arylene group and heteroarylene group of L ₁ and L ₂ are each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazo Hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycle with 3 to 60 nuclear atoms Alkyl group, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, At this time, when the substituents are plural, they are the same or different from each other.

According to one example, when n ₁ and n ₂ are each 1 or 2, L ₁ and L ₂ are the same or different from each other, are each independently directly bonded, or are composed of the following linker groups Link-1 to Link-7 It may be one or more linker groups selected from the group.

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

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

Y is O or S.

Hydrogen of the linker groups Link-1 to Link-7 is deuterium (D), halogen, cyano group, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and 5 to 9 nuclear atoms. It may be substituted with one or more substituents such as heteroaryl group.

Depending on L ₁ and L ₂ , the compound represented by Formula 1 may be a compound represented by Formula 6 below, but is not limited thereto.

(In Formula 6 above,

Ar ₁ , Ar ₂ , R ₁ and R ₂ are each as defined in clause 1,

m ₁ , m ₂ , m ₃ and m ₄ are each 0 or 1,

a, b, c and d are each 0 or 1,

e, f, g and h are each integers from 0 to 6,

Ra to Rd are the same or different from each other, and each independently represents deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, and a hydrazono group. ), C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ ~C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₆₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, and C ₆ ~ C ₆₀ arylamine group, wherein the substituent is In case of plurality, they are the same or different from each other.

According to one example, the compound represented by Formula 1 may be a compound represented by any one of Formulas 7 to 14 below. However, it is not limited to this.

In Formulas 7 to 14,

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

In the compound represented by Formula 1 according to the present invention, R ₁ and R ₂ are the same or different from each other, and each independently represents hydrogen, deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, or amidino group. ), hydrazino group, hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ Cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, cycloalkenyl group having ₃ to ₆₀ nuclear atoms, _{heterocycloalkenyl} group having 3 to 60 nuclear atoms, aryl group having 5 to ₆₀ nuclear atoms, 60 heteroaryl groups, C _{1 ~} C ₆₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C 60 alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, and C ₆ ~ C ₆₀ arylamine group. is selected.

According to one example, R ₁ and R ₂ may be the same or different from each other, and may each independently be selected from the group consisting of a C ₁ to C ₃₀ alkyl group and a C ₆ to C ₆₀ aryl group. Here, when R ₁ and/or R ₂ are each an alkyl group of C ₁ to C ₃₀ , the structural bulkiness can be reduced in terms of molecular structure, which is advantageous for packing during the manufacture of the device, and this makes the device Efficiency can be improved in terms of driving. On the other hand, when R ₁ and/or R ₂ are each an aryl group of C ₆ to C ₆₀ , the overlap between the p-orbitals in the R ₁ and R ₂ portion increases, increasing the number of cases of intermolecular hopping. This can improve the driving efficiency of the device.

According to another example, R ₁ and R ₂ are the same or different from each other, and are each independently methyl, ethyl, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t -Can be selected from the group consisting of butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, anthryl group, naphthacenyl group, pyrenyl group, and chrysenyl group. .

R ₁ and R ₂ hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl group, aryl group, heteroaryl group, alkyloxy group, Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, and amino group. , amidino group, hydrazino group, hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group , C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, aryl with C ₆ ~ C ₆₀ group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₆₀ alkylsilyl group, C ₆ to C ₆₀ aryl Silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when the substituents are plural, they are the same or different from each other.

Depending on R ₁ and R ₂ , the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 15 to 18, but is not limited thereto.

In Formulas 15 to 18,

Ar ₁ , Ar ₂ , n ₁ , n ₂ , L ₁ , and L ₂ are each as defined in Formula 1 above,

x ₁ and x ₂ are each integers from 0 to 2,

y ₁ and y ₂ are each integers from 0 to 3,

R ₃ to R ₈ are the same or different from each other, and each independently represents hydrogen or an alkyl group of C ₁ to C ₄ . Specifically, R ₃ , R ₅ , R ₆ and R ₈ may each independently represent hydrogen or a methyl group, R ₄ and R ₇ may each be a methyl group.

The compound represented by Formula 1 according to the present invention described above may be specified as any one of the following compounds A-1 to Z-16. However, the compound represented by Formula 1 according to the present invention is not limited to the examples below.

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 in the ring, preferably 1 to 3 carbons, 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, preferably 1 to 3 carbons, of the ring is replaced 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 fused 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, or It refers to a combination of these forms.

<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 material layers 300 include any of the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport auxiliary layer 360, the electron transport layer 340, and the electron injection layer 350. It may include one or more, of which 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 at least one of the light emitting layer 330, the electron transport layer 340, and the electron transport auxiliary layer 360.

According to one example, the one or more organic layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, the light-emitting layer includes a host and a dopant, and the host is a compound represented by Formula 1 It can be. In this case, the light-emitting layer of the present invention may include a compound known in the art as a second host in addition to the compound of Formula 1 above.

In the present invention, the content of the host may be about 70 to 99.9% by weight based on the total amount of the light-emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light-emitting layer.

When the compound represented by Formula 1 is included as a light-emitting layer material of an organic electroluminescent device, specifically a blue, green, and red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer increases, thereby increasing the efficiency of the organic electroluminescent device ( Luminous efficiency and power efficiency), lifespan, brightness, and driving voltage can be improved. Specifically, the compound represented by Formula 1 is preferably included in an organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Formula 1 of the present invention is a green phosphorescent exciplex N-type host material of a highly efficient light-emitting layer.

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 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 this organic electroluminescent device, electrons are 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 bonding force between holes and electrons in the light-emitting layer is increased. 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 is a 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. At this time, the compound of 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 includes at least one of the organic material layers 300 (e.g., the light emitting layer 330, the electron transport layer 340, or the electron transport auxiliary layer 360) containing the compound represented by Formula 1 above. Except, the organic material layer and electrode can be formed by using materials and methods known in the art.

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 Core-1

<Step 1> Synthesis of 2-(4-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine

6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2,4]triazolo[1,5- a]pyridine (30.0 g, 63 mmol), 9-bromo-10-chloroanthracene (16.1 g, 55 mmol), Pd(PPh ₃ ) ₄ (3.2 g, 3.15 mmol), and K ₂ CO ₃ (23 g, 189 mmol) was added to THF (500 ml) and H ₂ O (200 ml), and stirred at 75°C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and then water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain 2-(4-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1, 5-a]pyridine (29 g, yield 83%) was obtained.

¹ H-NMR: δ 7.25 (d, 2H), 7.41 (t, 2H), 7.44 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.51 (d, 4H), 7.96 ( d, 2H), 8.18 (d, 2H), 8.37 (d, 2H), 8.43 (s, 1H), 9.03 (s, 1H)

<Step 2> Synthesis of Core-1

2-(4-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine (25 g, 36 mmol), Pd(dppf )Cl ₂ (1.32 g, 2 mmol), Pinacol diboron (11 g, 43.2 mmol), and KOAc (10.6 g, 108 mmol) were added to DMF (200 ml) and stirred at 110°C for 8 hours. After completion of the reaction, H ₂ O was added, extraction was performed with ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-1 (29 g, yield 82%).

¹ H-NMR: δ 1.24 (s, 12H), 7.25 (d, 2H), 7.41 (t, 2H), 7.44 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.51 ( d, 4H), 7.96 (d, 2H), 8.18 (d, 2H), 8.37 (d, 2H), 8.43 (s, 1H), 9.03 (s, 1H)

[Preparation Example 2] Synthesis of Core-2

<Step 1> Synthesis of 2-(2-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine

(2-(2-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)-4,5,5-trimethyl-1,3,2 -dioxaborolan-4-yl)methylium (30.0 g, 63 mmol), 9-bromo-10-chloroanthracene (16.1 g, 55 mmol), Pd(PPh ₃ ) ₄ (3.2 g, 3.15 mmol), and K ₂ CO ₃ (23 g, 189 mmol) was added to THF (500 ml) and H ₂ O (200 ml) and stirred at 75°C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and then water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain 2-(2-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1, 5-a]pyridine (29 g, yield 83%) was obtained.

¹ H-NMR: δ 7.25 (d, 2H), 7.42 (t, 2H), 7.43 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.59 (d, 4H), 7.96 ( d, 2H), 8.18 (d, 2H), 8.37 (d, 2H), 8.53 (s, 1H), 9.03 (s, 1H)

<Step 2> Synthesis of Core-2

2-(2-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine (25 g, 36 mmol), Pd(dppf )Cl ₂ (1.32 g, 2 mmol), Pinacol diboron (11 g, 43.2 mmol), and KOAc (10.6 g, 108 mmol) were added to DMF (200 ml) and stirred at 110°C for 8 hours. After completion of the reaction, H ₂ O was added, extraction was performed with ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-2 (16 g, yield 42%).

¹ H-NMR: δ 1.24 (s, 12H), 7.25 (d, 2H), 7.42 (t, 2H), 7.43 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.59 ( d, 4H), 7.96 (d, 2H), 8.18 (d, 2H), 8.37 (d, 2H), 8.53 (s, 1H), 9.03 (s, 1H)

[Preparation Example 3] Synthesis of Core-3

<Step 1> 2-(3'-(10-chloroanthracen-9-yl)-[1,1'-biphenyl]-3-yl)-6,8-diphenyl-[1,2,4]triazolo[1 Synthesis of ,5-a]pyridine

6,8-diphenyl-2-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)- [1,2,4]triazolo[1,5-a]pyridine (30.0 g, 55 mmol), 9-bromo-10-chloroanthracene (18.1 g, 65 mmol), Pd(PPh ₃ ) ₄ (4.2 g, 2.7 mmol), and K ₂ CO ₃ (28 g, 165 mmol) were added to THF (500 ml) and H ₂ O (200 ml) and stirred at 75°C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and then water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain 2-(3'-(10-chloroanthracen-9-yl)-[1,1'-biphenyl]-3-yl)-6,8- diphenyl-[1,2,4]triazolo[1,5-a]pyridine (35 g, yield 88%) was obtained.

¹ H-NMR: δ 7.41 (d, 2H), 7.44 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.51 (t, 2H), 7.61 (d, 4H), 7.73 ( d, 4H), 7.94 ( , 2H), 8.18 (d, 1H), 8.37 (d, 2H), 8.43 (s, 1H), 9.03 (s, 1H)

<Step 2> Synthesis of Core-3

2-(3'-(10-chloroanthracen-9-yl)-[1,1'-biphenyl]-3-yl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a ]pyridine (20 g, 36 mmol), Pd(dppf)Cl ₂ (1.32 g, 2 mmol), Pinacol diboron (11 g, 43.2 mmol), and KOAc (10.6 g, 108 mmol) were added to DMF (200 ml). Added and stirred at 110°C for 8 hours. After completion of the reaction, H ₂ O was added, extraction was performed with ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain Core-3 (17 g, yield 38%).

¹ H-NMR: δ 1.24 (s, 12H), δ 7.41 (d, 2H), 7.44 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.51 (t, 2H), 7.61 (d, 4H), 7.73 (d, 4H), 7.94 ( , 2H), 8.18 (d, 1H), 8.37 (d, 2H), 8.43 (s, 1H), 9.03 (s, 1H)

[Preparation Example 4] Synthesis of Core-4

<Step 1> Synthesis of 2-(3-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine

6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,2,4]triazolo[1,5- a]pyridine (16.1 g, 55 mmol), Pd(PPh ₃ ) ₄ (3.2 g, 3.15 mmol), and K ₂ CO ₃ (23 g, 189 mmol) were mixed with THF (500 ml) and H ₂ O (200 ml). ) and stirred at 75°C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and then water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain 2-(3-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1, 5-a]pyridine (31 g, yield 86%) was obtained.

¹ H-NMR: δ 7.25 (d, 2H), 7.42 (t, 2H), 7.43 (t, 2H), 7.45 (t, 2H), 7.46 (t, 4H), 7.59 (d, 4H), 7.96 ( d, 2H), 8.18 (d, 2H), 8.37 (d, 2H), 8.53 (s, 1H), 9.03 (s, 1H)

<Step 2> Synthesis of Core-4

2-(3-(10-chloroanthracen-9-yl)phenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine (28 g, 95 mmol), Pd(dppf )Cl ₂ (2.8 g, 4 mmol), Pinacol diboron (29 g, 114 mmol), and KOAc (28 g, 283 mmol) were added to DMF (200 ml) and stirred at 110°C for 8 hours. After completion of the reaction, H ₂ O was added, extraction was performed with ethyl acetate, the organic layer was separated, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography to obtain Core-4 (35 g, yield 88%).

¹ H-NMR: δ 1.24 (s, 12H), 7.00 (t, 1H), 7.38 (d, 1H), 7.50 (t, 1H), 7.52 (t, 1H), 7.59 (t, 1H), 7.98 ( d, 1H), 8.00 (d, 1H), 8.33 (d, 1H), 8.45 (d, 1H), 8.50 (d, 1H)

[Synthesis Example 1] Synthesis of Compound H-1

Core-1 (5.0g, 7.6mmol), (3-bromophenyl)diphenylphosphine oxide (3.6g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 1 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.2 g of compound H-1 (yield 65%) was obtained using column chromatography.

[LCMS] : 799

[Synthesis Example 2] Synthesis of Compound B-4

Core-1 (5.0g, 7.6mmol), (4-bromophenyl)dimethylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 1 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.9 g of compound B-4 (yield 76%) was obtained using column chromatography.

[LCMS] : 675

[Synthesis Example 3] Synthesis of Compound I-1

Core-1 (5.0g, 7.6mmol), (3-bromophenyl)dimethylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 1 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml), and then stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.4 g of compound I-1 (yield 73%) was obtained using column chromatography.

[LCMS] : 675

[Synthesis Example 4] Synthesis of Compound O-3

Core-2 (5.0g, 7.6mmol), (3-bromophenyl)diphenylphosphine oxide (3.6g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 2 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml), and then stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 1.8 g of compound O-3 (yield 36%) was obtained using column chromatography.

[LCMS] : 799

[Synthesis Example 5] Synthesis of Compound P-4

Core-2 (5.0g, 7.6mmol), (3-bromophenyl)dimethylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 2 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 2.1 g of compound P-4 (yield 46%) was obtained using column chromatography.

[LCMS] : 675

[Synthesis Example 6] Synthesis of Compound V-4

Core-3 (5.5g, 7.6mmol), (4-bromophenyl)diphenylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 3 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 2.3 g of compound V-4 (yield 46%) was obtained using column chromatography.

[LCMS]: 876

[Synthesis Example 7] Synthesis of Compound V-8

Core-3 (5.5g, 7.6mmol), (3-bromophenyl)diphenylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 3 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 2.4 g of compound V-8 (yield 48%) was obtained using column chromatography.

[LCMS] : 876

[Synthesis Example 8] Synthesis of Compound W-3

Core-3 (5.5g, 7.6mmol), (4-bromophenyl)diphenylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 3 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 2.8 g of compound W-3 (yield 58%) was obtained using column chromatography.

[LCMS] : 752

[Synthesis Example 9] Synthesis of Compound W-4

Core-3 (5.5g, 7.6mmol), (3-bromophenyl)diphenylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 3 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 2.6 g of compound W-4 (yield 54%) was obtained using column chromatography.

[LCMS] : 752

[Synthesis Example 10] Synthesis of Compound H-3

Core-4 (5.0g, 7.6mmol), (4-bromophenyl)diphenylphosphine oxide (3.6g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 4 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.2 g of compound H-3 (yield 65%) was obtained using column chromatography.

[LCMS] : 799

[Synthesis Example 11] Synthesis of Compound H-4

Core-4 (5.0g, 7.6mmol), (3-bromophenyl)diphenylphosphine oxide (3.6g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 4 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.6 g of compound H-4 (yield 72%) was obtained using column chromatography.

[LCMS] : 799

[Synthesis Example 12] Synthesis of Compound I-3

Core-4 (5.0g, 7.6mmol), (4-bromophenyl)dimethylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 4 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.9 g of compound I-3 (yield 76%) was obtained using column chromatography.

[LCMS] : 675

[Synthesis Example 13] Synthesis of Compound I-4

Core-4 (5.0g, 7.6mmol), (3-bromophenyl)dimethylphosphine oxide (2.4g, 10.0mmol), Pd(pph ₃ ) ₄ (0.43g, 0.38mmol), and K ₂ CO synthesized in Preparation Example 4 ₃ (3.1g, 22.8mmol) was dissolved in toluene (150ml), ethanol (40ml), and H ₂ O (40ml) and stirred at 120°C for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and H ₂ O, moisture was removed with MgSO ₄ , and 3.5 g of compound I-4 (yield 83%) was obtained using column chromatography.

[LCMS] : 675

[Example 1] Fabrication of a blue organic electroluminescent device

Compound H-1 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 as follows.

first. A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 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, DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm)/Compound H-1 (30 nm) )/LiF (1 nm)/Al (200 nm) were stacked in that order to produce an organic electroluminescent device. The structures of NPB and ADN used at this time are as follows.

[Examples 2 to 13] Fabrication of blue organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the electron transport layer materials in Table 1 were used instead of compound H-1 used as the electron transport layer material in Example 1.

[Comparative Example 1] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 1, except that Alq ₃ was used instead of Compound H-1 used as the electron transport layer material in Example 1. The structure of Alq ₃ used at this time is as follows.

[Comparative Example 2] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-1 was used instead of Compound H-1, which was used as the electron transport layer material in Example 1. The structure of compound T-1 used at this time is as follows.

[Comparative Example 3] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-2 was used instead of Compound H-1, which was used as the electron transport layer material in Example 1. The structure of compound T-2 used at this time is as follows.

[Comparative Example 4] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-3 was used instead of Compound H-1, which was used as the electron transport layer material in Example 1. The structure of compound T-3 used at this time is as follows.

[Comparative Example 5] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-4 was used instead of Compound H-1, which was used as the electron transport layer material in Example 1. The structure of compound T-4 used at this time is as follows.

[Evaluation Example 1]

For each of the blue organic electroluminescent devices manufactured in Examples 1 to 13 and Comparative Examples 1 to 5, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. shown in

Sample electron transport layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 Compound H-1 3.2 454 8.0 Example 2 Compound B-4 3.3 456 8.9 Example 3 Compound I-1 3.1 457 8.3 Example 4 Compound O-3 3.2 452 8.6 Example 5 Compound P-4 3.1 455 8.5 Example 6 Compound V-4 3.3 452 8.3 Example 7 Compound V-8 3.4 453 7.7 Example 8 Compound W-3 3.3 454 7.8 Example 9 Compound W-4 3.2 455 7.9 Example 10 Compound H-3 3.2 456 9.0 Example 11 Compound H-4 3.1 454 10.1 Example 12 Compound I-3 3.4 455 9.3 Example 13 Compound I-4 3.4 456 9.2 Comparative Example 1 Alq ₃ 5.4 458 5.5 Comparative Example 2 T-1 4.5 459 5.9 Comparative Example 3 T-2 4.4 458 6.0 Comparative Example 4 T-3 3.7 454 7.6 Comparative Example 5 T-4 3.6 456 7.8

As shown in Table 1, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, The blue organic electroluminescence devices of Examples 1 to 13 using H-3, H-4, I-3, I-4) in the electron transport layer are the blue organic electroluminescence devices of Comparative Example 1 using conventional Alq ₃ in the electron transport layer. It was found that it showed superior performance in terms of driving voltage, emission peak, and current efficiency compared to other devices.

In addition, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, H-3, H- The blue organic electroluminescent devices of Examples 1 to 13 using 4, I-3, I-4) in the electron transport layer have an anthracene-containing linker group as a linking group, and a comparison using a compound having an anthracene-free linker group in the electron transport layer It was found that compared to the blue organic electroluminescent device of Examples 2 and 3, it exhibited superior performance in terms of driving voltage, emission peak, and current efficiency. In addition, the blue organic electroluminescent devices of Examples 1 to 13 contain a triazolo-pyridine moiety, and thus the blue color of Comparative Examples 4 to 5 in which a compound containing another N-containing heterocycle such as triazine was used in the electron transport layer. It was found to exhibit superior performance in terms of driving voltage, emission peak, and current efficiency compared to organic electroluminescent devices.

[Example 14] Fabrication of a blue organic electroluminescent device

Compound H-1 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 1500 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, DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30nm)/Compound H-1 (5 nm) An organic electroluminescent device was manufactured by stacking /Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) in that order. The structures of NPB and ADN used at this time are the same as those described in Example 1, and the structures of Alq3 are the same as those described in Comparative Example 1, so they are omitted.

[Examples 15 to 26] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that the electron transport auxiliary layer materials listed in Table 2 were used instead of Compound H-1, which was used as the electron transport auxiliary layer material in Example 14. did.

[Comparative Example 6] Fabrication of blue organic electroluminescent device

Compound H-1, which was used as the electron transport auxiliary layer material in Example 14, was not used, and Alq ₃ , the electron transport layer material, was deposited at 30 nm instead of 25 nm, and was carried out in the same manner as Example 14 to obtain a blue color. An organic electroluminescent device was manufactured.

[Comparative Example 7] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound T-1 was used instead of Compound H-1, which was used as the electron transport auxiliary layer material in Example 14. Since the structure of compound T-1 used at this time is the same as that described in Comparative Example 2, it is omitted.

[Comparative Example 8] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 14, except that Compound T-2 was used instead of Compound H-1 as the electron transport auxiliary layer material in Example 14. Since the structure of compound T-2 used at this time is the same as that described in Comparative Example 3, it is omitted.

[Comparative Example 9] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 14, except that Compound T-3 was used instead of Compound H-1 as the electron transport auxiliary layer material in Example 14. Since the structure of compound T-3 used at this time is the same as that described in Comparative Example 4, it is omitted.

[Comparative Example 10] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound T-4 was used instead of Compound H-1 as the electron transport auxiliary layer material in Example 14. Since the structure of compound T-4 used at this time is the same as that described in Comparative Example 5, it is omitted.

[Evaluation Example 2]

For each of the blue organic electroluminescent devices manufactured in Examples 14 to 26 and Comparative Examples 6 to 10, the driving voltage, emission peak, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below. shown in

Sample Electron transport auxiliary layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 14 Compound H-1 4.3 452 8.0 Example 15 Compound B-4 3.7 451 8.4 Example 16 Compound I-1 4.5 452 7.6 Example 17 Compound O-3 3.8 454 8.2 Example 18 Compound P-4 3.7 451 7.3 Example 19 Compound V-4 4.2 452 8.0 Example 20 Compound V-8 4.5 453 7.6 Example 21 Compound W-3 4.4 454 7.5 Example 22 Compound W-4 4.1 455 7.4 Example 23 Compound H-3 4.6 456 6.2 Example 24 Compound H-4 3.7 451 8.4 Example 25 Compound I-3 4.5 452 7.6 Example 26 Compound I-4 3.8 454 8.2 Comparative Example 6 - 4.8 458 6.0 Comparative Example 7 T-1 4.7 457 6.1 Comparative Example 8 T-2 4.6 456 6.2 Comparative Example 9 T-3 4.2 454 6.8 Comparative Example 10 T-4 4.1 456 7.2

As shown in Table 2, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, The blue organic electroluminescent device of Examples 14 to 26 using H-3, H-4, I-3, I-4) in the electron transport auxiliary layer is the blue organic electroluminescent device of Comparative Example 6 without the electron transport auxiliary layer. Compared to , it was found to have excellent performance in terms of current efficiency, emission peak, and driving voltage.

In addition, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, H-3, H- The blue organic electroluminescent devices of Examples 14 to 26 using 4, I-3, and I-4) in the electron transport auxiliary layer have an anthracene-containing linker group as a linking group, thereby assisting electron transport of compounds having an anthracene-free linker group. It was found that it exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Examples 7 to 8 used in the layer. In addition, the blue organic electroluminescent devices of Examples 14 to 26 contain a triazolo-pyridine moiety, and thus the blue color of Comparative Examples 9 to 10 in which compounds containing other N-containing heterocycles such as triazine were used in the electron transport layer. It was found to exhibit superior performance in terms of driving voltage, emission peak, and current efficiency compared to organic electroluminescent devices.

[Example 27] Fabrication of a green organic electroluminescent device

Compound H-1 synthesized in Synthesis Example 1 was purified to high purity by sublimation using a commonly known method, and then a green 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 1500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .

m-MTDATA (60 nm)/TCTA (80 nm)/90% of compound H-1 + 10% of Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq on the ITO transparent electrode prepared as above. An organic electroluminescent device was manufactured by stacking ₃ (30 nm)/LiF (1 nm)/Al (200 nm) in the order. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used at this time are as follows.

[Examples 28 to 39] Fabrication of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 27, except that the host materials listed in Table 3 were used instead of Compound H-1 used as the host material in Example 27.

[Comparative Example 11] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same process as Example 27, except that CBP was used instead of Compound H-1, which was used as a light-emitting host material when forming the light-emitting layer in Example 27. The structure of CBP used at this time is as follows.

[Comparative Example 12] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same process as Example 27, except that Compound T-1 was used instead of Compound H-1, which was used as the light-emitting host material when forming the light-emitting layer in Example 27. Since the structure of compound T-1 used at this time is the same as that described in Comparative Example 2, it is omitted.

[Comparative Example 13] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same process as Example 27, except that Compound T-2 was used instead of Compound H-1, which was used as the light-emitting host material when forming the light-emitting layer in Example 27. Since the structure of compound T-2 used at this time is the same as that described in Comparative Example 3, it is omitted.

[Comparative Example 14] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same process as Example 27, except that Compound T-3 was used instead of Compound H-1, which was used as the light-emitting host material when forming the light-emitting layer in Example 27. Since the structure of compound T-3 used at this time is the same as that described in Comparative Example 4, it is omitted.

[Comparative Example 15] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same process as Example 27, except that Compound T-4 was used instead of Compound H-1, which was used as the light-emitting host material when forming the light-emitting layer in Example 27. Since the structure of compound T-4 used at this time is the same as that described in Comparative Example 5, it is omitted.

[Evaluation Example 3]

For each green organic electroluminescent device manufactured in Examples 27 to 39 and Comparative Examples 11 to 15, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 3 below. indicated.

Sample host material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 27 Compound H-1 6.81 518 39.7 Example 28 Compound B-4 6.48 518 44.9 Example 29 Compound I-1 6.66 518 41.3 Example 30 Compound O-3 6.70 517 41.3 Example 31 Compound P-4 6.70 515 43.1 Example 32 Compound V-4 6.51 518 43.5 Example 33 Compound V-8 6.77 518 41.4 Example 34 Compound W-3 6.82 517 41.3 Example 35 Compound W-4 6.66 515 41.3 Example 36 Compound H-3 6.86 516 41.2 Example 37 Compound H-4 6.81 518 39.7 Example 38 Compound I-3 6.48 518 44.9 Example 39 Compound I-4 6.66 518 41.3 Comparative Example 11 CBP 6.93 516 38.2 Comparative Example 12 T-1 6.9 517 39.5 Comparative Example 13 T-2 6.87 517 39.2 Comparative Example 14 T-3 6.88 518 39.9 Comparative Example 15 T-4 6.91 517 40.6

As shown in Table 3, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, The green organic electroluminescent devices of Examples 27 to 39 using H-3, H-4, I-3, I-4) in the emitting layer have a higher current than the green organic electroluminescent device of Comparative Example 11 using conventional CBP in the emitting layer. It was found to exhibit excellent performance in terms of efficiency and driving voltage.

In addition, the compounds of the present invention (compounds H-1, B-4, I-1, O-3, P-4, V-4, V-8, W-3, W-4, H-3, H- The green organic electroluminescent devices of Examples 27 to 39 using 4, I-3, and I-4) in the emitting layer had an anthracene-containing linker group as a linking group, and a compound having an anthracene-free linker group was used in the electron transport auxiliary layer. It was found that compared to the blue organic electroluminescent device of Comparative Examples 12 to 13, it exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency. In addition, the blue organic electroluminescent devices of Examples 27 to 39 contain a triazolo-pyridine moiety, and thus the blue color of Comparative Examples 14 to 15 in which a compound containing another N-containing heterocycle such as triazine was used in the electron transport layer. It was found to exhibit superior performance in terms of driving voltage, emission peak, and current efficiency compared to organic electroluminescent devices.

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)

Compound represented by Formula 1:
[Formula 1]

(In Formula 1 above,
Ar ₁ and Ar ₂ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazo Hydrazono group, C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycle with 3 to 60 nuclear atoms Alkyl group, C ₃ to C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₆₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group,
n ₁ and n ₂ are each integers from 0 to 2,
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 60 nuclear atoms,
R ₁ and R ₂ are the same as or different from each other, and are each independently an alkyl group of C ₁ to C ₆₀ ,
The arylene group and heteroarylene group of L ₁ and L ₂ , and the hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, hetero group of Ar ₁ and Ar ₂ Cycloalkenyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group, and The alkyl groups of R ₁ and R ₂ are each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group. , C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ ~ C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₆₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C It is substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphine group of _{6 to C 60, an arylphosphine oxide group of C 6 to} C ₆₀ , and an arylamine group of _{C 6} to C ₆₀ , wherein the substituents are plural. , they are the same or different from each other). According to paragraph 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen or an aryl group of C ₆ to C ₃₀ . According to paragraph 1,
Compounds represented by any of the following formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

(In Formulas 2 to 5,
n ₁ , n ₂ , L ₁ , L ₂ , R ₁ and R ₂ are each as defined in clause 1). According to paragraph 1,
wherein n ₁ and n ₂ are each 1 or 2,
Wherein L ₁ and L ₂ are the same or different from each other and are each independently directly bonded or a linker group selected from the group consisting of the following linker groups Link-1 to Link-7:

(In the linker group Link-7,
Y is O or S). According to paragraph 1,
Compound represented by the following formula (6):
[Formula 6]

(In Formula 6 above,
Ar ₁ , Ar ₂ , R ₁ and R ₂ are each as defined in clause 1,
m ₁ , m ₂ , m ₃ and m ₄ are each 0 or 1,
a, b, c and d are each 0 or 1,
e, f, g and h are each integers from 0 to 6,
Ra to Rd are the same or different from each other, and each independently represents deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, and a hydrazono group. ), C ₁ ~ C ₆₀ alkyl group, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ C ₆₀ cycloalkyl group, heterocycloalkyl group with 3 to 60 nuclear atoms, C ₃ ~C ₆₀ cycloalkenyl group, heterocycloalkenyl group with 3 to 60 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₆₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₆₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, selected from the group consisting of a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group). According to paragraph 1,
Compounds represented by any of the following formulas 7 to 14:
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

(In Formulas 7 to 14,
Ar ₁ , Ar ₂ , R ₁ and R ₂ are each as defined in clause 1). delete According to paragraph 1,
Compound represented by Formula 18:
[Formula 18]

(In Formula 18 above,
Ar ₁ , Ar ₂ , n ₁ , n ₂ , L ₁ , and L ₂ are each as defined in clause 1,
y ₁ and y ₂ are each integers from 0 to 3,
R ₃ to R ₈ are the same as or different from each other, and are each independently hydrogen or an alkyl group of C ₁ to C ₄ ). According to paragraph 1,
The compound represented by Formula 1 is any one of the following compounds:

. An organic electroluminescent device comprising an anode, a cathode, and one or more organic material 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 6, 8, and 9. According to clause 10,
An organic electroluminescent device wherein the organic material layer containing the compound is at least one selected from the group consisting of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

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