KR20220063558A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent electron transport ability, luminescent ability, and thermal stability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including a compound in one or more organic material layers. In order to achieve the above object, the present invention provides a compound represented by chemical formula 1.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device including the same, and more particularly, to a compound excellent in electron transport ability, light emitting ability and heat resistance, and luminous efficiency, driving voltage, lifespan, etc. by including the compound in one or more organic material layers It relates to an organic electroluminescent device with improved characteristics.

Taking the observation of organic thin film emission by Bernanose in the 1950s as a starting point, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 continued. ) presented an organic electroluminescent device with a stacked structure divided into a hole layer and a functional layer of a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, an exciton is formed, and when the exciton falls to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing better natural colors according to the emission color. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as the phosphorescent dopant are in progress.

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

However, conventional organic material layer materials are advantageous in terms of light emitting characteristics, but have not reached a satisfactory level in terms of the lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is not very good. Accordingly, there is a demand for the development of an organic layer material having excellent performance.

The present invention is to provide a novel compound that 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, etc. make it a task

In addition, it is another technical task of the present invention to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound described above.

Other objects and advantages of the present invention may be more clearly explained by the following detailed description and claims.

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

In Formula 1,

X is Si or Ge,

Y is O, S or Se,

Z ₁ To Z ₃ Are the same as or different from each other, and each independently C(R ₁₃ ) or N, provided that at least one of Z ₁ To Z ₃ is N,

Ar ₁ 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, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a 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 Aryl phosphine group , C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or these may be combined with an adjacent group to form a condensed ring;

L ₁ To L ₃ Are the same as or different from each other, and each independently is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

a, b, and c are each an integer from 0 to 3,

R ₁ To R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or they combine with an adjacent group to form a condensed ring can form;

The arylene group and heteroarylene group of L ₁ to L ₃ , and the Ar ₁ , R ₁ to R ₁₃ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, a phosphine group, a phosphine oxide group, and an arylamine group, and the Ar ₁ to Ar ₄ aryl groups are each independently hydrogen, 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 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylamine group, and in this case, when a plurality of the substituents are the same or different from each other.

In addition, the present invention includes 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 an organic electroluminescent device comprising a compound represented by Formula 1 provides

Here, the organic material layer including 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, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Formula 1 may be included as at least one material of a phosphorescent host material of the emission layer, an electron transport layer, and an electron transport auxiliary layer.

In one embodiment of the present invention, since the compound represented by Formula 1 has excellent electron transport ability, light emitting ability, heat resistance, etc., it can be used as an organic material layer material of an organic electroluminescent device.

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

Accordingly, the organic electroluminescent device including the compound represented by Chemical Formula 1 can greatly improve aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel or the like.

Effects according to the present invention are not limited by the contents exemplified above, and more various effects are included in the present specification.

Hereinafter, the present invention will be described in detail.

<Organic compound>

According to the present invention, the compound represented by Formula 1 is centered on a nitrogen-containing heteroaromatic ring (eg, azine, Z ₁ to Z ₃ containing ring), and has three substituents, such as a silane/germane-based moiety ( For example, an X-containing ring), a dibenzo-based moiety (eg, a Y-containing ring) and an Ar ₁ moiety are directly linked or have a basic skeleton structure connected through a separate linker (eg, L ₁ to L ₃ ) .

Specifically, the compound of Formula 1 includes a dibenzo-based moiety and a silane/Germane-based moiety having weak electron donor (EDG) properties; It contains a nitrogen-containing aromatic ring (eg, pyrazine, pyrimidine, triazine), which is a kind of azine group, which is an electron withdrawing group (EWG) with high electron absorption. By introducing an azine group, which is a functional group having a strong electron withdrawing capability (EWG) as described above, the electron transfer speed is improved, and thus it is possible to have physicochemical properties more suitable for electron injection and electron transport. When the compound of Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can accept electrons from the cathode well and thus smoothly transfer electrons to the light emitting layer, thereby lowering the driving voltage of the device and improving high efficiency and long lifespan can induce As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.

In particular, the two weak EDG groups described above have structural features bound to one strong EWG group, and thus have widely distributed HOMO and LUMO orbitals throughout the molecule. In addition, since the silane/germain-based moiety (eg, tetraphenylsilane, dibenzo-based cillin, etc.) has a high triplet energy (T1) value through steric hindrance, the exciton generated in the light-emitting layer is adjacent to the light-emitting layer. It is possible to prevent diffusion into the electron transport layer or the hole transport layer. In addition, the number of excitons contributing to light emission in the light emitting layer can be increased to improve the luminous efficiency of the device, and the durability and stability of the device can be improved to effectively increase the lifetime of the device.

In addition, since the compound of Formula 1 is a bipolar compound, the recombination of holes and electrons is high, so that hole injection/transport capability, luminous efficiency, driving voltage, lifespan characteristics, durability, etc. can be improved. In addition, the electron transport ability and the like can be improved depending on the type of the introduced substituent. Therefore, the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a light emitting layer material.

Furthermore, the compound represented by Formula 1 is not only very advantageous for electron transport, but also shows low driving voltage, high efficiency, and long lifespan characteristics. The excellent electron transport ability of these compounds can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, the organic electroluminescent device using the compound can exhibit high electron transport ability.

On the other hand, the red and green light emitting layers of the organic electroluminescent device use phosphorescent materials, respectively, and their technological maturity is high. In contrast, the blue light emitting layer has a fluorescent material and a phosphorescent material. Among them, the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a high development possibility and a relatively high technical difficulty, there is a limit in improving the performance (eg, driving voltage, efficiency, lifespan, etc.) of a blue organic light emitting device having the blue light emitting layer. Accordingly, in the present invention, the compound of Formula 1 may be applied as a material for an electron transport layer (ETL) or an electron transport auxiliary layer in addition to the light emitting layer (EML). As such, through the material change of the electron transport layer or electron transport auxiliary layer used as a common layer in the organic electroluminescent device, the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic electroluminescent device having the same are improved. There are advantages to being able to

According to the present invention, the compound represented by Formula 1 is centered on a nitrogen-containing heteroaromatic ring (eg, azine, Z ₁ to Z ₃ containing ring), and has three substituents, such as a dibenzo-based moiety (eg, Y containing ring), a silane/Germane-based moiety (eg, an X containing ring, X = Si, Ge), and an Ar ₁ moiety, which may be directly linked or a separate linker (eg, L ₁ to L ₃ ) has a basic skeletal structure connected through Here, at least two or more of the three substituents described above are different, or all of them are different.

The nitrogen-containing heterocycle (eg, Z ₁ to Z ₃ containing ring) may be a monocyclic nitrogen-containing heteroaryl group including at least one nitrogen atom. In an embodiment of the nitrogen-containing heteroaromatic ring (eg, Z ₁ to Z ₃ containing ring), Z ₁ to Z ₃ are the same as or different from each other, and each independently is N or CR ₁₃ , provided that Z ₁ to Z At least one of ₃ is N. For a specific example, Z ₁ to Z ₃ include 1 to 3 N, preferably 2 to 3 N. As such, by including a heterocyclic ring containing 2 to 3 nitrogens, more excellent electron absorption properties are exhibited, which is advantageous for electron injection and transport.

For example, the nitrogen-containing heterocycle (Z ₁ to Z ₃ containing ring) may be any one selected from the group of substituents represented by the following Chemical Formulas A-1 to A-5.

In the above formula,

* means a moiety combined with Formula 1 above.

R ₁₃ located in the nitrogen-containing heterocycle is the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alke Nyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms , C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group , C ₆ ~ C ₆₀ Aryl boron group, C ₁ ~ C ₄₀ phosphine group, C ₁ ~ C ₄₀ phosphine oxide group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group. Specifically, R ₁₃ is preferably selected from the group consisting of hydrogen, deuterium, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

The nitrogen-containing heterocycle according to the present invention (eg, Z ₁ to Z ₃ containing ring) includes a silane/germaine-based moiety; dibenzo-based moieties; and Ar ₁ is introduced through a direct bond or a separate linker (eg, L ₁ to L ₃ ).

As the silane/germaine-based moiety (eg, X-containing ring, X=Si/Ge, etc.), conventional silane/germaine-based moieties known in the art may be used without limitation, for example, arylsilane-based and/or aryl It may be a Germain-based moiety.

For example, the silane/germaine-based moiety may be selected from structural formulas represented by the following Chemical Formulas 2a to 2c. However, the present invention is not particularly limited thereto.

[Formula 2a]

[Formula 2b]

[Formula 2c]

In the above formula,

* means a moiety combined with Formula 1,

X and R ₉ to R ₁₂ are each as defined in Formula 1.

For a specific example of the silane/germane-based moiety (X-containing ring), it may be represented by the following structural formula.

As various substituents, R ₉ to R ₁₂ may be substituted in the silane/germaine-based moiety (X-containing ring). These R ₉ to R ₁₂ are not particularly limited, and hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 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 Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, Alternatively, it may combine with adjacent groups (eg, R ₉ to R ₁₂ ) to form a condensed ring. Specifically, R ₉ to R ₁₂ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and nucleus It may be selected from a heteroaryl group having 5 to 60 atoms. Here, at least one of R ₉ to R ₁₂ , specifically R ₁₀ is preferably selected from the group consisting of hydrogen, a cyano group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

The dibenzo-based moiety (eg, Y-containing ring) according to the present invention is excellent in terms of high glass transition temperature (Tg) and thermal stability. In one embodiment of such a dibenzo-based moiety (eg, a Y-containing ring), Y is O, S, or Se, specifically O (dibenzofuran) or S (dibenzothiophene), preferably is O.

The dibenzo-based moiety may be substituted with R ₁ to R ₈ as various substituents. These R ₁ to R ₈ are not particularly limited, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl Boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ From the group consisting of an arylamine group It may be selected or combined with adjacent groups (eg, R ₁ to R ₈ ) to form a condensed ring. Specifically, R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and nucleus It may be selected from a heteroaryl group having 5 to 60 atoms. Here, at least one of R ₁ to R ₈ , specifically R ₁ is preferably selected from the group consisting of a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

In addition, to one side of the aforementioned nitrogen-containing heterocycle (eg, Z ₁ to Z ₃ containing ring), Ar ₁ is introduced as a substituent. Ar ₁ is not particularly limited, and for example, 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, 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 Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or these may be combined with an adjacent group to form a condensed ring.

For example, Ar ₁ may have a substituent represented by Formula 3 or Formula 4 below.

[Formula 3]

[Formula 4]

In the above formula,

* means a moiety combined with Formula 1,

Y is O or S;

n is an integer of 1 or 2.

the aforementioned silane/germaine-based moieties (eg, an X-containing ring); dibenzo-based moieties (eg, Y-containing rings); and Ar ₁ moieties are each directly bonded to a nitrogen-containing aromatic ring (eg, a ring containing Z ₁ to Z ₃ ) or bonded through a linker (L ₁ to L ₃ ). As such, when a separate linker exists between the above-described moiety and the nitrogen-containing aromatic ring, the HOMO region is expanded to give a benefit to the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through proper overlap of the HOMO-LUMO. .

Such a linker (eg, L ₁ to L ₃ ) is not particularly limited, and may be a single bond or a linker of a conventional divalent group known in the art. Specifically, L _One To L ₃ Are the same as or different from each other, and each independently a single bond (eg, a direct bond) or C ₆ ~ C ₁₈ Arylene group and 5 to 18 nuclear atoms composed of a heteroarylene group may be selected from the group. Specific examples of the arylene group and heteroarylene group include a phenylene group, a biphenylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, and a pyrimidinylene group. . More specifically, L ₁ to L ₃ are the same as or different from each other, and each independently is a single bond or a C ₆ to C ₁₂ arylene group and a heteroarylene group having 5 to 12 nuclear atoms Can be selected from the group consisting of there is.

In this case, the number of linkers (eg, a, b, c) may be an integer of 0 to 3, respectively. For example, when a, b, and c are 0, L ₁ to L ₃ may each be a single bond. In addition, when a, b, and c are respectively greater than 0 and less than or equal to 3, a plurality of L ₁ to L ₃ may be the same as or different from each other, and may each independently be the remaining substituents except for a single bond in the definition portion of the above-mentioned linker.

For example, L ₁ to L ₃ may be the same as or different from each other, and may each independently be a single bond or a linking group selected from the following structural formula.

In the above formula,

* means a moiety combined with Formula 1 above.

In addition, although not shown in the above-mentioned structural formula, at least one or more substituents known in the art (eg, the same as the definition of R ₁ to R ₈ ) may be substituted.

In the above formula 1, the arylene group and heteroarylene group of L ₁ to L ₃ , the Ar ₁ , R ₁ to R ₁₃ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, An alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, a phosphine group, a phosphine oxide group, and an arylamine group are each independently hydrogen, 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, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group.

For an embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Formulas 5 to 7 below depending on the type of a silane/germaine-based moiety (eg, an X-containing ring).

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,

X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , a, b and c are each as defined in Formula 1 .

The compounds represented by Chemical Formulas 5 to 7 may be more specific to any one of the following Chemical Formulas 5a to 7b.

[Formula 5a]

[Formula 5b]

[Formula 6a]

[Formula 6b]

[Formula 7a]

[Formula 7b]

In Formulas 5a to 7b,

Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , a, b and c are each as defined in Formula 5-7.

In another embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 8 or 9 according to the type of Ar ₁ connected to an azine group (eg, Z ₁ to Z ₃ containing ring).

[Formula 8]

[Formula 9]

In Formula 8 or 9,

X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , R ₁ to R ₁₂ , a, b and c are each as defined in Formula 1,

n is an integer of 1 or 2.

The compound represented by Formula 8 or 9 may be more specific to any one of Formulas 8a to 9b below.

[Formula 8a]

[Formula 8b]

[Formula 9a]

[Formula 9b]

In Formula 8a or 9b,

Y, Z ₁ to Z ₃ , L ₁ to L ₃ , R ₁ to R ₁₂ , n, a, b and c are each as defined in Formula 8-9.

In another embodiment of the present invention, the compound represented by Chemical Formula 1 may be prepared according to the following Chemical Formulas 10 to 13 according to the type of a substituent (eg, R ₁₀ ) introduced to a silane/germaine-based moiety (eg, an X-containing ring). may be displayed as any one of them.

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In Formulas 10 to 13,

X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , a, b and c are each as defined in Formula 1,

R ₁₄ and R ₁₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,

The alkyl group, aryl group and heteroaryl group of R ₁₄ and R ₁₅ are each independently hydrogen, 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, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 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 Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ With one or more substituents selected from the group consisting of an arylamine group may be substituted, and in this case, when the substituents are plural, they may be the same as or different from each other. Specifically, R ₁₄ and R ₁₅ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and nucleus It may be selected from a heteroaryl group having 5 to 60 atoms.

The compound represented by Chemical Formulas 10 to 13 may be more specific to any one of the following Chemical Formulas 10a to 13b.

[Formula 10a]

[Formula 10b]

[Formula 11a]

[Formula 11b]

[Formula 12a]

[Formula 12b]

[Formula 13a]

[Formula 13b]

In Formula 10a or 13b,

X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , R ₁₄ to R ₁₅ , a, b and c are each as defined in Formula 10-13.

The compound represented by Formula 1 of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by 1 to 120. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

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

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

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

In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means an 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, pentoxy, and the like.

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

In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, "alkylsilyl" 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 comprising the compound represented by the formula (1).

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 an electron transport layer material known in the art. It is preferably used alone.

The electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compound, aluminum complex (eg, Alq ₃ (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg, Gaq'2OPiv, Gaq) '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.

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 may be appropriately adjusted within a range known in the art.

<Electron transport auxiliary layer material>

In addition, the present invention provides an electron transport auxiliary layer comprising the compound represented by the formula (1).

The electron transport layer is disposed between the emission layer and the electron transport layer, and serves to prevent the excitons or holes generated in the emission 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 an electron transport layer material known in the art. It is preferably used alone.

The electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a heterocyclic derivative containing nitrogen, and the like.

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

<Organic electroluminescent device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Formula 1 according to the present invention.

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

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer is represented by Formula 1 including compounds. Specifically, the organic material layer including the compound of Formula 1 is preferably a light emitting layer (more specifically, a phosphorescent light emitting host material), an electron transport layer, and 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 compound of Formula 1 may be included as the host material. In addition, the light emitting layer of the present invention may include a known compound 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, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of the light emitting layer having high efficiency.

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, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably the 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 stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at 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 organic material layer includes the compound represented by Formula 1 above. there is.

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

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.

In addition, as the cathode material, a cathode material known in the art may be used without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, as the negative electrode material, any negative electrode material known in the art may be used without limitation. For example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.

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

[Synthesis Example 1] Synthesis of compound 1

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 1 (3.28 g, yield 50%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 657

[Synthesis Example 2] Synthesis of compound 2

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-4-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 2 (3.22 g, yield 49%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 657

[Synthesis Example 3] Synthesis of compound 3

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-phenyl-6-(6 -phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazine (4.33 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g) , 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 3 (3.52 g, yield 48%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 734

[Synthesis Example 4] Synthesis of compound 4

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-([1,1'-biphenyl]- 3-yl)-4-chloro-6-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazine (5.09 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 4 (3.80 g, yield 47%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 810

[Synthesis Example 5] Synthesis of compound 5

triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 5 (3.02 g, yield 46%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 657

[Synthesis Example 6] Synthesis of compound 6

triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(3-(dibenzo[ b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (4.33 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 6 (3.30 g, yield 45%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 734

[Synthesis Example 7] Synthesis of compound 7

triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-phenyl-6-(6 -phenyldibenzo[b,d]furan-1-yl)-1,3,5-triazine (4.33 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g) , 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 7 (3.22 g, yield 44%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 734

[Synthesis Example 8] Synthesis of compound 8

triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-([1,1'-biphenyl]- 4-yl)-4-chloro-6-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazine (5.09 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 8 (3.48 g, yield 43%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 810

[Synthesis Example 9] Synthesis of compound 9

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4,6-bis(dibenzo[ b,d]furan-4-yl)-1,3,5-triazine (4.47 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) ) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 9 (3.14 g, yield 42%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 748

[Synthesis Example 10] Synthesis of compound 10

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-4-yl)-6-(naphthalen-1-yl)-1,3,5-triazine (4.07 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 10 (2.90 g, yield 41%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 708

[Synthesis Example 11] Synthesis of compound 11

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-3-yl)-6-(dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine (4.63 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 11 (3.13 g, yield 41%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 764

[Synthesis Example 12] Synthesis of compound 12

triphenyl(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)silane (5.38 g, 10 mmol) , 2-chloro-4-phenyl-6-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine (4.49 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 12 (3.46 g, yield 42%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 826

[Synthesis Example 13] Synthesis of compound 13

4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)benzonitrile (4.87 g, 10 mmol), 2-chloro-4-( dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 13 (2.93 g, yield 43%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 682

[Synthesis Example 14] Synthesis of compound 14

5,5-diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole (4.60 g, 10 mmol), 2 -chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (4.47 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol) , K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 14 (3.28 g, yield 44%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 746

[Synthesis Example 15] Synthesis of compound 15

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3'-(triphenylsilyl)-[1,1'-biphenyl]-3-carbonitrile (5.63 g, 10 mmol), 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 15 (3.41 g, yield 45%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 759

[Synthesis Example 16] Synthesis of compound 16

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-([1,1':3', 1''-terphenyl]-5'-yl)-4-chloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (5.09 g, 10 mmol), Pd ( PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 1,4-Dioxane 100 ml/ H ₂ O 25 ml and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 16 (3.72 g, yield 46%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 810

[Synthesis Example 17] Synthesis of compound 17

3-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)pyridine (5.39 g, 10 mmol), 2- chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol) , K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 17 (3.45 g, yield 47%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 735

[Synthesis Example 18] Synthesis of compound 18

diphenylbis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (5.88 g, 10 mmol), 2-bromo-6-(dibenzo[b,d ]furan-4-yl)pyridine (6.48 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) 1,4-Dioxane 100 ml/ It was put in 25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 18 (3.95 g, yield 48%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 823

[Synthesis Example 19] Synthesis of compound 19

triphenyl(3''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':3',1''-terphenyl]-3-yl) silane (6.14 g, 10 mmol), 4-chloro-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (3.56 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 19 (3.96 g, yield 49%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 809

[Synthesis Example 20] Synthesis of compound 20

triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)germane (5.07 g, 10 mmol), 2-chloro-4-(dibenzo[b,d ]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H ₂ O and stirred at 100° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound 20 (3.51 g, yield 50%) was obtained by column chromatography.

Mass : [(M+H) ⁺ ] : 702

[Examples 1 to 20] Fabrication of a blue organic electroluminescent device

After high-purity sublimation purification of the compound synthesized in the above synthesis example by a commonly known method, a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Solus, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Solus, 30 nm)/Electron transport auxiliary layer material in Table 1 (5 nm)/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

[Comparative Example 1] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transport auxiliary layer material, and Alq3, an electron transport layer material, was deposited at 30 nm instead of 25 nm.

The structures of NPB, ADN, and Alq3 used in Examples 1 to 20 and Comparative Example 1 are as follows.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Example 1, respectively, the driving voltage, the emission wavelength, and the current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample electronic transport
auxiliary layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 One 4.2 453 8.1 Example 2 2 3.7 454 8.2 Example 3 3 4.7 453 8.1 Example 4 4 3.8 455 8.1 Example 5 5 4.2 452 8.2 Example 6 6 4.4 453 8.3 Example 7 7 4.8 454 8.0 Example 8 8 5.2 454 8.1 Example 9 9 5.1 452 8.2 Example 10 10 4.2 454 8.5 Example 11 11 4.3 453 7.7 Example 12 12 4.4 453 8.3 Example 13 13 4.1 455 7.4 Example 14 14 4.2 453 8.1 Example 15 15 4.2 453 7.7 Example 16 16 4.1 454 6.8 Example 17 17 4.2 451 6.7 Example 18 18 4.1 452 7.6 Example 19 19 3.2 453 6.1 Example 20 20 3.2 456 6.0 Comparative Example 1 - 5.4 458 5.5

As shown in Table 1, the blue organic light emitting devices of Examples 1 to 20 using the compound of the present invention as an electron transport auxiliary layer material were applied to the blue organic electroluminescent device of Comparative Example 1 without an electron transport auxiliary layer. In comparison, it was found that the device exhibits superior performance in terms of driving voltage, emission peak, and current efficiency.

Claims (16)

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

In Formula 1,
X is Si or Ge,
Y is O, S or Se,
Z ₁ To Z ₃ Are the same as or different from each other, and each independently C(R ₁₃ ) or N, provided that at least one of Z ₁ To Z ₃ is N,
Ar ₁ 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, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a 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 Aryl phosphine group , C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or these may be combined with an adjacent group to form a condensed ring;
L ₁ To L ₃ Are the same as or different from each other, and each independently is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
a, b, and c are each an integer from 0 to 3,
R ₁ To R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or they combine with an adjacent group to form a condensed ring can form;
The arylene group and heteroarylene group of L ₁ to L ₃ , and the Ar ₁ , R ₁ to R ₁₃ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, a phosphine group, a phosphine oxide group, and an arylamine group, and the Ar ₁ to Ar ₄ aryl groups are each independently hydrogen, 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 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylamine group, and in this case, when a plurality of the substituents are the same or different from each other. According to claim 1,
The X-containing ring is a compound represented by any one of the following formulas 2a to 2c:
[Formula 2a]

[Formula 2b]

[Formula 2c]

In the above formula,
* means a moiety combined with Formula 1,
X and R ₉ to R ₁₂ are each as defined in claim 1. According to claim 1,
The X ₁ to X ₃ containing ring is a compound selected from the group of substituents represented by the following A-1 to A-5:

In the above formula,
* means a moiety combined with Formula 1,
R ₁₃ is as defined in claim 1. According to claim 1,
Z ₁ to Z ₃ is a compound comprising 2 to 3 N. According to claim 1,
Ar ₁ is a compound represented by Formula 3 or Formula 4:
[Formula 3]

[Formula 4]

In the above formula,
* means a moiety combined with Formula 1,
Y is O or S;
n is an integer of 1 or 2. According to claim 1,
L ₁ To L ₃ Are the same as or different from each other, and each independently a single bond or a linking group selected from the following structural formula.

In the above formula,
* means a moiety combined with Formula 1 above. According to claim 1,
R ₁ To R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and heteroaryl having 5 to 60 nuclear atoms selected from the group consisting of
The alkyl group, the aryl group and the heteroaryl group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of 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 Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ May be substituted with one or more substituents selected from the group consisting of an arylamine group, wherein When the substituents are plural, they may be the same as or different from each other. According to claim 1,
At least one of R ₉ to R ₁₂ is hydrogen, a cyano group, a C ₆ to C ₆₀ aryl group, and a compound selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 5 to 7:
[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,
X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , a, b and c are each as defined in claim 1 . According to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 8 or Formula 9:
[Formula 8]

[Formula 9]

In Formula 8 or 9,
X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , R ₁ to R ₁₂ , a, b and c are each as defined in claim 1 ,
n is an integer of 1 or 2. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 10 to 13:
[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In Formulas 10 to 13,
X, Y, Z ₁ to Z ₃ , L ₁ to L ₃ , Ar ₁ , R ₁ to R ₁₂ , a, b and c are each as defined in claim 1,
R ₁₄ and R ₁₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 1 to 120.

According to claim 1,
The compound represented by Formula 1 is a material of a light emitting layer, an electron transport layer, or an electron transport auxiliary layer. A positive electrode, a negative electrode, and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers is an organic material comprising the compound according to any one of claims 1 to 13. electroluminescent device. 15. The method of claim 14,
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 hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer. 16. The method of claim 15,
The compound is an organic electroluminescent device comprising at least one material of a phosphorescent host material of the light emitting layer, an electron transport layer, and an electron transport auxiliary layer.