KR20240103075A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound with excellent carrier transport ability, luminescence ability, and thermal stability, and an organic electroluminescent device with improved properties such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers.

Description

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

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same. More specifically, it relates to a compound with excellent electron transport ability and an organic light-emitting compound with improved properties such as luminous efficiency, driving voltage, and lifespan by including it in one or more organic layers. It relates to electroluminescent devices.

Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices, which led to blue electroluminescence using anthracene single crystals in 1965, was divided into a functional layer of a hole layer and a light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure was presented. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

When a voltage is applied between two electrodes in an organic electroluminescent 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 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 layer materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials depending on the light-emitting color. 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 luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The dopant material can be divided into fluorescent dopant using organic material and phosphorescent dopant using metal complex compound 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, NPB, BCP, and Alq ₃ are widely known as materials used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, 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 efficiency improvement 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, conventional light-emitting materials have advantages in terms of light-emitting properties, but because their glass transition temperature is low and thermal stability is very poor, they are not at a satisfactory level in terms of lifespan in organic electroluminescent devices. Therefore, there is a demand for the development of light-emitting materials with excellent performance.

The present invention can be applied to organic electroluminescent devices, and its technical task is to provide a new organic compound with excellent hole and electron injection and transport capabilities, luminescence ability, etc.

In addition, another technical task of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage, high luminous efficiency, and improved lifespan by including the novel organic compound.

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

In Formula 1,

The plurality _of

R ₁ to R ₄ are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ It is selected from the group consisting of an aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or they are combined with adjacent groups to form a condensed ring. can be formed,

However, when R ₁ and R ₂ are each an aryl group of C ₆ to C ₆₀ , they are different from each other,

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 ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, or a C ₃ to C ₄₀ alkyl group. Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine group, an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ ,

The arylene group and heteroarylene group of L ₁ to L ₃ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, and alkyloxy group of Ar ₁ to Ar ₂ and R ₁ to R ₄ , cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium (D), halogen, and cyanogroup. No group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms , C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine It may be substituted with one or more substituents selected from the group consisting of an oxide group and an arylamine group of C ₆ to C ₆₀ . In this case, when the substituents are plural, they may be the same or different from each other.

In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and 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 includes a compound represented by Formula 1 above. provides.

Here, the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer. there is. At this time, the compound represented by Formula 1 may be included as at least one material among the phosphorescent host material, the electron transport layer, and the electron transport auxiliary layer of the light emitting layer.

For one embodiment of the present invention, the compound represented by Formula 1 has excellent electron transport ability, luminescence ability, heat resistance, etc., and therefore can be used as an organic material layer material of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host, electron transport layer, or electron transport auxiliary layer material, it has high thermal stability, low driving voltage, fast mobility, and high current efficiency compared to conventional host materials or electron transport materials. and long life characteristics.

Accordingly, the organic electroluminescent device containing the compound of Formula 1 can be greatly improved in aspects such as excellent light emission performance, low driving voltage, long life, and high efficiency, and therefore can be effectively applied to full color display panels, etc.

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.

Hereinafter, the present invention will be described in detail.

<New organic compounds>

The present invention provides novel aryl-based compounds, specifically tryptycene-based compounds, which have excellent thermal stability, carrier transport ability, and luminescence ability.

More specifically, the new organic compound according to the present invention adopts a triptycene group as a core, and an electron withdrawing group (EWG) with excellent electron transport ability is bonded to the core structure to form a basic skeleton.

The compound of Formula 1 having this structure can have structural stability, high glass transition temperature (Tg), and excellent thermal stability due to the substitution of the tryptycene group with a unique and rigid structure. In addition, it has a three-dimensional (3D) trigonal structure, so it has excellent packing density and increases steric hindrance, which can improve the efficiency of the device compared to materials with existing known structures. . In addition, the compound of Formula 1 can have physical and chemical properties more suitable for electron injection and electron transport by introducing an azine group, a functional group with strong electron attracting ability (EWG), to improve the electron transfer rate.

In addition, because the compound represented by Formula 1 of the present invention has high triplet energy, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. In particular, by introducing a strong EWG such as triazine or pyrimidine, the compound can induce polarization within the material and create a wide band gap, and utilize this to block holes coming from the light-emitting layer, thereby improving the stability of the device. can increase. Therefore, the number of excitons contributing to light emission in the light-emitting layer can be increased, thereby improving the light-emitting efficiency of the device, and the durability and stability of the device can be improved, effectively increasing the lifespan of the device. Most of the developed materials are capable of low-voltage operation and thus exhibit physical characteristics that improve their lifespan.

As described above, the compound represented by Formula 1 of the present invention is used as an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), an electron transport layer/injection layer material, and a hole material. When applied as a transport layer/injection layer material, a light emitting auxiliary layer material, and a lifespan improvement layer material, the performance and lifespan characteristics of an organic electroluminescent device can be greatly improved. In particular, when the compound of the present invention is used as an electron transport layer or electron transport auxiliary layer material, significantly improved performance can be expected in terms of device efficiency, driving voltage, and lifespan characteristics. These organic electroluminescent devices can ultimately maximize the performance of full-color organic light emitting panels.

The compound represented by Formula 1 according to the present invention uses a tritipcene group as a core, and the core structure includes a linker (eg, L ₁ to L ₃ ) and an electron withdrawing group (EWG) with excellent electron transport ability, For example, nitrogen-containing heterocycles (e.g., X-containing rings) are sequentially bonded to form the basic skeleton.

In Formula 1, the tryptycene-based core includes three benzene rings, and a nitrogen-containing heterocycle (e.g., X-containing ring) is connected to one of the two benzene rings located on a single plane.

The nitrogen-containing heterocycle (eg, X-containing ring) is a monocyclic or polycyclic nitrogen-containing heteroaryl group each containing at least one nitrogen atom. For example, in an example of a nitrogen _- containing heteroaromatic ring, the plurality of In this way, by including 2 to 3 nitrogen-containing heterocycles, it exhibits superior electron absorption characteristics and is advantageous for electron injection and transport.

Here, R ₄ is hydrogen, deuterium, 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 atoms 3 to 40 Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ arylheteroarylamine group and hetero of 5 to 60 nuclear atoms It may be selected from the group consisting of arylamine groups, or may be combined with adjacent groups (eg, R ₁ to R ₂ , R ₄ ) to form a condensed ring. Specifically, R ₄ is preferably selected from the group consisting of hydrogen, deuterium, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, and heteroaryl group with 5 to 60 nuclear atoms.

For example, the nitrogen-containing heterocycle may be further specified as one selected from the following structural formula. However, it is not limited to this.

In the above equation,

* refers to the region connected to Formula 1 above,

W is O or S,

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

_The nitrogen _- containing heterocycle (e.g., These R ₁ to R ₂ are the same as or different from each other, and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, or a C ₃ to C ₄₀ cyclo group. Alkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryl with C ₆ to C _60. Oxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a phosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or is bonded to any adjacent group (e.g., R ₁ to R ₂ , R ₄ ). Thus, a condensed ring can be formed. However, when R ₁ and R ₂ are each an aryl group of C ₆ to C ₆₀ , they are different from each other, and specifically, when both R ₁ and R ₂ are phenyl groups, they are excluded from the present invention. More specifically, R ₁ to R ₂ are each independently selected from the group consisting of an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms, but they are different from each other and are based on the nitrogen-containing heterocycle. Asymmetry is desirable.

For one specific example, R ₁ to R ₂ may each be independently selected from the structural formulas below.

In the structural formula above,

* is the portion connected to Chemical Formula 1. In addition, although not shown in the above structural formula, R ₁ to R ₂ may be substituted with at least one substituent (eg, R ₃ ) known in the art.

In addition, among the two benzene rings located on a single plane in the tryptycene core, Ar ₁ and Ar ₂ may be substituted with various substituents on one benzene ring and the phenyl ring on the other, respectively. These Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, and 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 to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ It may be 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. Specifically, Ar ₁ and Ar ₂ may each independently be selected from the group consisting of hydrogen, an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms, and more specifically, hydrogen, C ₆ It is preferable that they are an aryl group of ~C ₁₈ and a heteroaryl group of 5 to 18 nuclear atoms.

In addition, R ₃ may be substituted with various substituents on one benzene ring that does not exist in a single plane among the tryptycene cores. Such R ₃ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy with C ₆ to C _60. Period, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphos It may be selected from the group consisting of a pin group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group. Specifically, R ₃ may be hydrogen, an aryl group of C ₆ to C ₁₈ , or a heteroaryl group of 5 to 18 nuclear atoms, and is preferably hydrogen.

In the compound represented by Formula ₁ according to the present invention, the tryptycene-based core and _the nitrogen-containing heterocycle (e.g., Or, it is connected through a separate linker (e.g., L ₁ to L ₃ ). In this way, when a linker (eg, L ₁ to L ₃ ) is present, the HOMO region can be expanded to provide benefits to the HOMO-LUMO cell, and charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO.

The linker (eg, L ₁ to L ₃ ) is not particularly limited and may be a single bond or a linker of a common divalent group known in the art. For example, L ₁ to L ₃ are the same or different from each other, and each independently is a single bond (e.g., a direct bond) or consists of an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms. may be selected from the military.

Specific examples of the arylene group linker include phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, purinylene group, and quinine. There are nolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazonylene group, pyridinylene group, pyrimidinylene group, etc. More specifically, it is preferably a phenylene group or a biphenylene group. Additionally, an example of the heteroarylene group linker may be a dibenzo-based moiety, and specific examples thereof include dibenzofuran-based moieties, dibenzothiophene-based moieties, and/or dibenzoselenophenone-based moieties.

For one specific example, L ₁ to L ₃ are the same or different from each other, and each independently may be a single bond or a linker selected from a structural formula.

In the above equation,

* refers to the portion where a bond is formed with Formula 1 above. Although the above-described linkers (eg, L ₁ to L ₃ ) are not shown in the chemical formula, they may be substituted with at least one substituent (eg, R ₃ ) known in the art.

In the above-mentioned formula 1, the arylene group and heteroarylene group of L ₁ to L ₃ , the alkyl group of Ar ₁ to Ar ₂ and R ₁ to R ₄ , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryl Oxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium ( D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 Heterocycloalkyl group of 40 to 40, C ₆ to C ₆₀ aryl group, heteroaryl group of 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 ~ 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 ~ It may be substituted with one or more substituents selected from the group consisting of a C ₆₀ arylphosphine oxide group and a C ₆ to C ₆₀ arylamine group. In this case, when the substituents are plural, they may be the same or different from each other.

According to one embodiment of the present invention, the compound represented by Formula 1 may be further specified as one of the following Formulas 2 to 5 depending on the number of substituents bonded to the tryptycene-based core and its structure. However, it is not limited to this.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

X, Ar ₁ ~Ar ₂ , L ₁ ~L ₃ , and R ₁ ~R ₂ are each as defined in Formula 1.

According to another embodiment of the present invention, the compound represented by Formula 1 has the following Formula 6 or Formula 1 depending on the type of linker (L ₃ ) located between the tryptycene-based core and the nitrogen-containing heterocycle (X-containing ring): It can be specified as 7. However, it is not limited to this.

[Formula 6]

[Formula 7]

In Formula 6 or 7 above,

n is an integer from 1 to 3,

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

X, Ar ₁ ~Ar ₂ , L ₁ ~L ₂ , and R ₁ ~R ₂ are each as defined in claim 1.

According to another embodiment of the present invention, the compound represented by Formula 1 is specified as one of the following Formulas 8 to 11 depending on the type of R ₁ and R ₂ substituents connected to the nitrogen-containing heterocycle (X-containing ring). It can be. However, it is not limited to this.

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Formulas 8 to 11,

R ₅ and R ₆ are the same or different from each other, and are each independently selected from the group consisting of an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms,

Z is O or S,

o and q are each independently integers from 0 to 5,

X, Ar ₁ ~Ar ₂ , and L ₁ ~L ₃ are each as defined in Formula 1.

According to another embodiment of the present invention, the compound represented by Formula 1 is represented by any one of Formulas 12 to 14 below, depending on the type of R ₁ and R ₂ substituents connected to the nitrogen-containing heterocycle (X-containing ring). It can be materialized. However, it is not limited to this.

[Formula 12]

[Formula 13]

[Formula 14]

In Formulas 12 to 14,

In Formulas 14 to 16,

Ring A may be a monocyclic or polycyclic hydrocarbon ring group containing or not containing heteroatoms. Ring A may be a condensed or fused monocyclic or polycyclic hydrocarbon ring or nitrogen-containing ring known in the art, and may be, for example, an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a heteroaromatic ring. Preferably, it may be an aromatic ring with 6 to 18 carbon atoms, or a polycyclic heteroaromatic ring with 5 to 12 nuclear atoms containing heteroatoms. Here, the heteroatom may be N, O or S.

Z is O or S,

o is an integer from 0 to 5,

X, Ar ₁ ~Ar ₂ , and L ₁ ~L ₃ are each as defined in Formula 1.

The compound represented by Formula 1 of the present invention described above may be further specified as the compounds exemplified below, for example, compounds represented by 1 to 240. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified 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 methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc., but are not limited thereto.

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 and having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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 phenyl, naphthyl, phenanthryl, anthryl, etc., but are not limited thereto.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, 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 condensed form 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, “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, "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 alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 40 carbon atoms.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, 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, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

<Electron transport layer material>

The present invention provides an electron transport layer containing the compound represented by Formula 1 above.

The electron transport layer (ETL) serves to move electrons injected from the cathode to an adjacent layer, specifically the light emitting layer.

The compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with electron transport layer materials known in the art. Preferably it is used alone.

Electron transport layer materials that can be mixed 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) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq '2OAc, 2(Gaq'2)), etc. 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.

<Electron transport auxiliary layer material>

Additionally, the present invention provides an auxiliary electron transport layer containing the compound represented by Formula 1 above.

The electron transport layer is disposed between the light-emitting layer and the electron transport layer, and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

The compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with electron transport layer materials known in the art. Preferably it is used alone.

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. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a heterocyclic derivative containing nitrogen, etc.

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

<Organic electroluminescent device>

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more types.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic materials layers has the formula above. Includes compounds indicated by 1. Specifically, the organic material layer containing the compound of Formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and/or a lifespan improvement layer, and more specifically, a light-emitting layer (more specifically, a phosphorescent light-emitting host material). , an electron transport layer, or an electron transport auxiliary layer.

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

When the compound represented by Formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably 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.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. At this time, one or more of the hole injection layer, hole transport layer, auxiliary light emitting layer, light emitting layer, electron transport layer, and electron injection layer may include the compound represented by Formula 1, preferably a light emitting layer, more preferably a phosphorescent host. may include a compound represented by Formula 1 above. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the above-described organic material layer contains the compound represented by Formula 1. there is.

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 used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

Additionally, the anode material may be any cathode material known in the art without limitation. Examples 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, as the anode material, any anode material known in the art may be used without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO2/Al, etc., but are not limited thereto.

Additionally, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and common materials known in the art can be used without limitation.

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 examples 1 to 3]

[Preparation example 1]

<Step 1> Synthesis of Core 1

(9r,10r)-2-chloro-9,10-dihydro-9,10-[1,2]benzenoanthracene (50g, 173.2 mmol) and 4,4,4',4',5,5,5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (52.7 g, 207.8 mmol) and Pd(dppf)Cl ₂ (3.8 g, 5.19 mmol), KOAc (51 g, 519.4 mmol) , Xphos (8.25 g, 17.3 mmol) was added to 750ml of 1,4-Dioxane and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, Core1 (43 g, yield 65%) was obtained using column chromatography.

[LCMS] : 380

[Preparation example 2]

<Step 1> Synthesis of Core 2

(9R,10R)-2,6-dichloro-9,10-dihydro-9,10-[1,2]benzenoanthracene (63 g, 196.8 mmol) and phenylboronic acid (20 g, 164 mmol) were reacted with Pd(OAc). ₂ (1.1 g, 4.92 mmol), Cs ₂ CO ₃ ( ₁₀₆ g, 328 mmol), and It was heated and refluxed. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, Core 2 (32 g, yield 53%) was obtained using column chromatography.

[LCMS] : 365

<Step 2> Synthesis of Core 2

[Preparation Example 1] (9R,10R)-2-chloro-6-phenyl-9,10-dihydro-9,10-[1,2]benzenoanthracene (32 g, 87.7mmol) was used as a reactant in <Step 1>. Except for what was used, the same process as [Preparation Example 1] was performed to obtain 28g of Core2 (yield 70%).

[LCMS]: 457

[Preparation example 3]

<Step 1> Synthesis of Core 3

[Preparation Example 2] Except that (9r,10r)-2,3-dichloro-9,10-dihydro-9,10-[1,2]benzenoanthracene was used as the reactant in <Step 1>. 2] was performed to obtain 22g of Core3 (58% yield).

[LCMS]: 457

[Synthesis Examples 1 to 24]

[Synthesis Example 1] Synthesis of Inv 3

Core1 (10.8 g, 28.5 mmol) of [Preparation Example 1] and 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1, 3,5-triazine (10 g, 23.8 mmol), Pd(OAc) ₂ (0.16 g, 0.71 mmol), Cs ₂ CO ₃ (15.5 g, 47.6 mmol), and X-phos (1.13 g, 2.38 mmol) were mixed with Toluene. 120ml, 30ml of EtOH, and 30ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, Inv 3 (11.2 g, yield 73%) was obtained using column chromatography.

[LCMS] : 638

[Synthesis Example 2] Synthesis of Inv 22

4-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine The same process as [Synthesis Example 1] was performed, except that 2',1''-terphenyl]-4'-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine (10g 20.2mmol) was used. Inv 22 (10.3 g, yield 71%) was obtained.

[LCMS] : 713

[Synthesis Example 3] Synthesis of Inv 25

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-([1,1': [Synthesis example] Except that 3',1''-terphenyl]-4'-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (10g 20.16mmol) was used. 1] was performed to obtain Inv 25 (9.8 g, yield 68%).

[LCMS] : 714

[Synthesis Example 4] Synthesis of Inv 31

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4 Except that -phenyl-6-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,5-triazine (10g 17.4mmol) was used. Inv 31 (9.6 g, yield 69%) was obtained by performing the same process as [Synthesis Example 1].

[LCMS] : 790

[Synthesis Example 5] Synthesis of Inv 38

4-(3-chlorophenyl)-6 instead of 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine -(3',5'-diphenyl-[1,1':2',1''-terphenyl]-3-yl)-2-phenylpyrimidine (10g 15.45mmol) was used, [Synthesis Example 1 ] was performed to obtain Inv 38 (9.2 g, yield 68%).

[LCMS] : 866

[Synthesis Example 6] Synthesis of Inv 58

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(4-chlorophenyl)-4 -(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (10g 23.04mmol) was performed in the same manner as [Synthesis Example 1], except that Inv 58 (9.3 g, yield 62%) was obtained.

[LCMS] : 652

[Synthesis Example 7] Synthesis of Inv 68

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4 -(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (10g 23.04mmol) was performed in the same manner as [Synthesis Example 1], except that Inv 68 (9.5 g, yield 63%) was obtained.

[LCMS] : 652

[Synthesis Example 8] Synthesis of Inv 86

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 4-(4'-chloro-[ [Synthesis Example 1] except that 1,1'-biphenyl]-3-yl)-6-(dibenzo[b,d]furan-2-yl)-2-phenylpyrimidine (10g 19.6mmol) was used. The same process was performed to obtain Inv 86 (9.4 g, 65% yield).

[LCMS] : 727

[Synthesis Example 9] Synthesis of Inv 91

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ Except for using 1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10g 19.6mmol) Inv 91 (9.5 g, yield 66%) was obtained by performing the same process as [Synthesis Example 1].

[LCMS] : 728

[Synthesis Example 10] Synthesis of Inv 106

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ Except for using 1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10g 19.6mmol) Inv 106 (9.2 g, yield 64%) was obtained by performing the same process as [Synthesis Example 1].

[LCMS] : 728

[Synthesis Example 11] Synthesis of Inv 116

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4 Inv 116 was obtained by performing the same process as [Synthesis Example 1], except that ,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (10g 19.08mmol) was used. (9.8 g, yield 69%) was obtained.

[LCMS] : 742

[Synthesis Example 12] Synthesis of Inv 126

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4 -Carry out the same process as [Synthesis Example 1], except that (naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1,3,5-triazine (10g 20.6mmol) was used. Inv 126 (9.6 g, yield 66%) was obtained.

[LCMS] : 702

[Synthesis Example 13] Synthesis of Inv 139

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ 1,1'-biphenyl]-3-yl)-4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine (10g 17.85mmol) was used. Except, the same process as [Synthesis Example 1] was performed to obtain Inv 139 (9.7 g, yield 69%).

[LCMS] : 778

[Synthesis Example 14] Synthesis of Inv 152

4-(3-chlorophenyl)-6 instead of 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine -(naphtho[2,1-b]benzofuran-8-yl)-2-phenylpyrimidine (10g 20.7mmol) was performed in the same manner as [Synthesis Example 1], except for using Inv 152 (9.8 g, yield) 67%) was obtained.

[LCMS] : 701

[Synthesis Example 15] Synthesis of Inv 179

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4 [Synthesis Example 1], except that -(dibenzo[b,d]furan-4-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (10g 20.6mmol) was used. The same process was performed to obtain Inv 179 (9.5 g, 65% yield).

[LCMS] : 702

[Synthesis Example 16] Synthesis of Inv 197

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ 1,1'-biphenyl]-3-yl)-4-phenyl-6-(4-phenyldibenzo[b,d]furan-1-yl)-1,3,5-triazine (10g 17.06mmol) was used. Except, the same process as [Synthesis Example 1] was performed to obtain Inv 197 (9.2 g, yield 67%).

[LCMS]: 804

[Synthesis Example 17] Synthesis of Inv 200

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ 1,1'-biphenyl]-3-yl)-4-phenyl-6-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazine (10g 17.06mmol) was used. Except, the same process as [Synthesis Example 1] was performed to obtain Inv 200 (9.0 g, yield 65%).

[LCMS]: 804

[Synthesis Example 18] Synthesis of Inv 202

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 4-(3'-chloro-[ [Synthesis example] Except that 1,1'-biphenyl]-3-yl)-2-phenyl-6-(6-phenyldibenzo[b,d]furan-2-yl)pyrimidine (10g 17.09mmol) was used. 1] was followed to obtain Inv 202 (9.3 g, yield 67%).

[LCMS] : 803

[Synthesis Example 19] Synthesis of Inv 208

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(3'-chloro-[ Same process as [Synthesis Example 1], except that 1,1'-biphenyl]-3-yl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (10g 22.27mmol) was used. was performed to obtain Inv 208 (9.6 g, yield 64%).

[LCMS] : 667

[Synthesis Example 20] Synthesis of Inv 210

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4-(3- [Synthesis Example 1], except that (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (10g 20.04mmol) was used. By performing the same process, Inv 210 (9.7 g, yield 67%) was obtained.

[LCMS] : 717

[Synthesis Example 21] Synthesis of Inv 215

4-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine The same process as [Synthesis Example 1] was performed, except that 2',1''-terphenyl]-4'-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (10g 20.2mmol) was used. Inv 215 (9.36 g, yield 66%) was obtained.

[LCMS] : 713

[Synthesis Example 22] Synthesis of Inv 218

2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-(2-chlorophenyl)-4 -(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (10g 23.04mmol) was performed in the same manner as [Synthesis Example 1], except that Inv 218 (9.7 g, yield 64%) was obtained.

[LCMS] : 652

[Synthesis Example 23] Synthesis of Inv 227

Use Core2 (13g, 28.57mmol) instead of Core1 and 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5 Instead of -triazine, use 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine (10g, 23.8mmol) Inv 227 (10.6 g, yield 62%) was obtained by performing the same process as in [Synthesis Example 1], except that it was used.

[LCMS] : 714

[Synthesis Example 24] Synthesis of Inv 237

Instead of Core1, Core2 (12.6g, 27.65mmol) was used and 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3, Except that 2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (10g 23.04mmol) was used instead of 5-triazine. , Inv 237 (9.4 g, yield 56%) was obtained by performing the same process as [Synthesis Example 1].

[LCMS] : 728

[Reference example]

The structures of compounds HT-1, HAT-CN, HT-2, BH, BD, LiQ, and ET-1 to ET-4 used in the following Examples and Comparative Examples are as follows.

[Examples 1 to 10] Fabrication of blue organic electroluminescent device

Each compound synthesized above 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 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. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET An organic electroluminescent device was manufactured by stacking each compound of -2 (50 Å) / Inv 3 to Inv 106 in the following order: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å).

[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 ET-1 was used instead of compound Inv 3 as the electron transport layer material.

[Evaluation Example 1]

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

Sample electron transport layer driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 Inv 3 4.2 460 6.7 Example 2 Inv 22 4.5 461 6.8 Example 3 Inv 25 4.6 460 6.8 Example 4 Inv 31 4.4 461 6.6 Example 5 Inv 38 4.2 459 6.5 Example 6 Inv 58 4.6 458 6.8 Example 7 Inv 68 4.1 460 6.8 Example 8 Inv 86 4.2 462 7.0 Example 9 Inv 91 4.3 458 6.7 Example 10 Inv 106 4.3 461 6.6 Comparative Example 1 ET-1 4.8 460 6.0

As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 10 using the compound according to the present invention as the electron transport layer material are the blue organic electroluminescent devices of Comparative Example 1 using the conventional ET-1 compound as the electron transport layer material. It was found that it showed superior performance in terms of driving voltage, emission peak, and current efficiency compared to light-emitting devices.

[Examples 11 to 34] Preparation of blue organic electroluminescent device

Each compound synthesized above was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

A glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) 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, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / Inv An organic electroluminescent device was manufactured by stacking 3 ~ Inv 237 (50 Å) / ET-1: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in that order.

[Comparative Examples 2 to 4] Manufacturing of blue organic electroluminescent device

The blue color of Comparative Examples 2 to 4 was carried out in the same manner as Example 11, except that Inv 3 was not used as the electron transport auxiliary layer material and compounds ET-2 to ET-4 were used to deposit at 50 Å. An organic electroluminescent device was manufactured.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 11 to 34 and Comparative Examples 2 to 4, the driving voltage, emission wavelength, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm2, and the results are shown in the table below. It is shown in 2.

Sample electronic transport
auxiliary floor driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 11 Inv 3 4.1 460 6.8 Example 12 Inv 22 4.4 461 6.7 Example 13 Inv 25 4.0 462 7.2 Example 14 Inv 31 4.2 461 6.8 Example 15 Inv 38 3.9 460 7.0 Example 16 Inv 58 3.8 459 6.7 Example 17 Inv 68 4.4 458 6.6 Example 18 Inv 86 4.5 460 6.5 Example 19 Inv 91 4.0 462 7.2 Example 20 Inv 106 4.3 463 6.8 Example 21 Inv 116 4.1 458 6.6 Example 22 Inv 126 4.2 460 6.4 Example 23 Inv 139 3.8 461 7.2 Example 24 Inv 152 3.9 459 7.0 Example 25 Inv 179 4.2 460 6.8 Example 26 Inv 197 4.0 458 6.7 Example 27 Inv 200 3.9 459 6.9 Example 28 Inv 202 3.7 460 7.1 Example 29 Inv 208 3.8 459 6.7 Example 30 Inv 210 4.4 458 6.3 Example 31 Inv 215 4.5 460 7.2 Example 32 Inv 218 4.0 462 6.8 Example 33 Inv 227 4.3 463 6.6 Example 34 Inv 237 4.2 460 6.8 Comparative Example 2 ET-2 4.7 460 6.0 Comparative Example 3 ET-3 5.0 461 5.8 Comparative Example 4 ET-4 4.6 460 6.1

As shown in Table 2, the blue organic electroluminescent devices of Examples 11 to 34 containing the compound according to the present invention as an electron transport auxiliary layer material have lower current efficiency and driving compared to the organic electroluminescent devices of Comparative Examples 2 to 4. It was found that it showed excellent performance in terms of voltage.

Specifically, the organic electroluminescent device according to the present invention had the effect of increasing current efficiency compared to the previously known material of Comparative Example 2 due to the excellent packing density and increased steric hindrance of tryptycene. In addition, by introducing different moieties into the azine group of EWG characteristics, stability can be increased and the electron injection ability into EML can be improved, so a comparison is made of a compound containing a tryptycene group and an azine group, but the same aryl group is substituted on the azine group. It was confirmed that it had better current efficiency characteristics compared to the devices of Examples 3 and 4.

Claims (14)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
The plurality _of
R ₁ to R ₄ are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ It is selected from the group consisting of an aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or they are combined with adjacent groups to form a condensed ring. can be formed,
However, when R ₁ and R ₂ are each an aryl group of C ₆ to C ₆₀ , they are different from each other,
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 ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, or a C ₃ to C ₄₀ alkyl group. Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine group, an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ ,
The arylene group and heteroarylene group of L ₁ to L ₃ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, and alkyloxy group of Ar ₁ to Ar ₂ and R ₁ to R ₄ , cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium (D), halogen, and cyanogroup. No group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms , C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine It may be substituted with one or more substituents selected from the group consisting of an oxide group and an arylamine group having C ₆ to C ₆₀ . In this case, when the substituents are plural, they may be the same or different from each other. According to paragraph 1,
The X-containing moiety is a compound selected from the following structural formulas:

In the above equation,
* refers to the region connected to Formula 1 above,
W is O or S,
R ₁ and R ₂ are each as defined in clause 1. According to paragraph 1,
R ₁ and R ₂ are each independently selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms, but these are different from each other. According to paragraph 1,
R ₁ and R ₂ are the same as or different from each other, and each independently represents a compound selected from the following structural formulas:

In the structural formula above,
* is the portion connected to Chemical Formula 1. 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 linker selected from the following structural formulas:

In the above equation,
* refers to the portion where a bond is formed with Formula 1 above. According to paragraph 1,
Ar ₁ and Ar ₂ are the same or different from each other, and are each independently selected from the group consisting of hydrogen, an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
X, Ar ₁ ~Ar ₂ , L ₁ ~L ₃ , and R ₁ ~R ₂ are each as defined in claim 1. According to paragraph 1,
The compound represented by Formula 1 is represented by the following Formula 6 or Formula 7:
[Formula 6]

[Formula 7]

In Formula 6 or 7 above,
n is an integer from 1 to 3,
Y is selected from the group consisting of O, S and Se,
X, Ar ₁ ~Ar ₂ , L ₁ ~L ₂ , and R ₁ ~R ₂ are each as defined in claim 1. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 8 to 11:
[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Formulas 8 to 11,
R ₅ and R ₆ are the same or different from each other, and are each independently selected from the group consisting of an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms,
Z is O or S,
o and q are each independently integers from 0 to 5,
X, Ar ₁ ~Ar ₂ , and L ₁ ~L ₃ are each as defined in clause 1. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 12 to 14:
[Formula 12]

[Formula 13]

[Formula 14]

In Formulas 14 to 16,
Ring A is a monocyclic or polycyclic hydrocarbon ring group containing or not containing heteroatoms,
Z is O or S,
o is an integer from 0 to 5,
X, Ar ₁ ~Ar ₂ , and L ₁ ~L ₃ are each as defined in clause 1. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 1 to 240.












According to paragraph 1,
The compound represented by Formula 1 is a material for a light emitting layer, an electron transport layer, or an electron transport auxiliary layer. An organic material comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers contains the compound according to any one of claims 1 to 12. Electroluminescent device. According to clause 13,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer.