KR102263237B1 - Organic electro luminescence device - Google Patents

Abstract

The present invention is a positive electrode; cathode; and at least one organic material layer interposed between the anode and the cathode, wherein the at least one organic material layer is positioned between the light emitting layer and the light emitting layer and the cathode, and a first organic material layer containing a novel electron transporting compound. It provides an organic electroluminescent device, characterized in that.

Description

Organic electroluminescent device {ORGANIC ELECTRO LUMINESCENCE DEVICE}

The present invention relates to an organic electroluminescent device with significantly improved performance and lifetime by including an electron transporting organic material layer containing a novel organic compound between a cathode and a light emitting layer.

Starting with Bernanose's observation of organic thin film emission in the 1950s, research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices'), which led to blue electroluminescence using anthracene single crystals, continued in 1965. Oda, and Tang (1987) proposed an organic EL device having a stacked structure divided into a hole layer and a functional layer of a light emitting layer. Since then, in order to make an organic EL device with high efficiency and long life, 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 the 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 injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted.

In such an organic electroluminescent device, excitons are sometimes generated in a region other than the emission layer due to the fast movement of holes. As such, excitons generated in a region other than the emission layer emit light in the region, and thus there is a problem in that the color and luminance of the emitted light are deteriorated.

Accordingly, in the prior art, in order to increase the performance and brightness of the organic electroluminescent device, a material capable of blocking the movement of holes, such as BCP or BPhen, is formed around the light emitting layer to block the movement of holes to areas other than the light emitting layer, and the light emitting layer By limiting it, the recombination rate of holes and electrons was increased. However, derivatives such as BCP or BPhen have poor oxidative stability for holes and poor durability against heat, resulting in reduced lifespan of organic electroluminescent devices, and thus have not been commercialized. In addition, these materials inhibit the movement of electrons to increase the driving voltage of the organic electroluminescent device.

Accordingly, there is a demand for the development of an organic electroluminescent device capable of lowering a driving voltage and improving light-emitting characteristics and lifespan due to excellent electron mobility.

An object of the present invention is to provide an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifespan in order to solve the above problems.

The present invention is a positive electrode; cathode; and at least one organic material layer interposed between the anode and the cathode, wherein the at least one organic material layer comprises a light emitting layer and a first organic layer containing a compound represented by the following formula (1) between the light emitting layer and the cathode An organic electroluminescent device is provided.

In Formula 1,

Cy1 and Cy2 are the same as or different from each other, and are each independently _{selected from the group consisting of a C 6} ~ C ₄₀ aromatic ring and a heteroaromatic ring having 5 to 40 nuclear atoms;

R _{1 To} R ₄ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ aryl boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent group to form a condensed ring can;

X ₁ and X ₂ are the same as or different from each other, and each independently from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ) selected, provided that at least one of _{X 1} and X _{2 is N(Ar 1} ), wherein when Ar ₁ is plural, they are the same or different from each other; Ar ₁ to Ar ₅ are the same as or different from each other, and are each independently As C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, Heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ groups of the alkyl silyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C of ₆ ~ C ₄₀ is selected from the group consisting of an arylsilyl group;

In this case, the C ₆ ~ C ₄₀ aromatic ring of Cy1 and Cy2, the heteroaromatic ring having 5 to 40 nuclear atoms, and the C ₁ ~ C ₄₀ alkyl group of _{R 1} to R ₄ and Ar ₁ to Ar _{5 , C 2} ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ of alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl groups are each independently a heavy hydrogen of the (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 nuclear atoms of heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms of heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ of an arylphosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group substituted or unsubstituted with one or more substituents selected from the group consisting of, in this case, when a plurality of the substituents are the same or different from each other.

According to an example, the one or more organic layer includes an electron transport layer between the first organic layer and the cathode, wherein the first organic layer is an electron transport auxiliary layer.

According to another example, the first organic material layer containing the compound represented by Formula 1 is an electron transport layer.

The organic electroluminescent device according to the present invention includes a first organic material layer formed of a novel compound between the cathode and the light emitting layer, particularly between the light emitting layer and the electron transport layer, so that the first organic material layer due to the novel organic compound excellent in thermal stability and electron transport properties In addition to having superior light emitting performance compared to the conventional organic electroluminescent device that does not include, it can have a low driving voltage, high efficiency, and a long lifespan, and further improve the performance and lifespan of the full color display panel.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.

Hereinafter, the present invention will be described in detail.

In the organic electroluminescent device according to the present invention, an anode, at least one organic material layer and a cathode are sequentially stacked, in which case the at least one organic material layer is a light emitting layer, and between the light emitting layer and the cathode by Formula 1 It is characterized in that it comprises a first organic material layer containing the indicated compound.

The compound represented by Formula 1 is an electron-transporting compound, and an aromatic ring at one end of an indenoindole moiety, an indoloindole moiety, or a benzothianoindole moiety. and/or a heteroaromatic ring is fused to form a basic skeleton, and has a structure in which various substituents are bonded to the basic skeleton.

Since the compound represented by Chemical Formula 1 has a planar molecular structure, interaction between molecules increases and thus has strong electron transport properties, the driving voltage of the OLED can be lowered. When an electron withdrawing group (EWG) having high electron absorption is bound to the basic skeleton of such a compound, since the entire molecule of the compound has a bipolar characteristic, it is possible to increase the bonding force between holes and electrons in the light emitting layer, thereby Due to this, excitons are efficiently formed, so that luminous efficiency may be improved. Therefore, when the compound represented by Formula 1 is applied between the light emitting layer and the cathode of the organic EL device, the phosphorescence emission characteristics of the organic EL device can be improved, and the electron injection ability, transport ability or luminous efficiency can also be improved. and the driving voltage of the device is lowered.

In addition, in the compound of Formula 1, various aromatic ring substituents introduced into the basic skeleton, in particular an aryl group and/or a heteroaryl group, are introduced, thereby significantly increasing the molecular weight of the compound, and thus the glass transition temperature can be improved to have higher thermal stability than conventional CBP (4,4-dicarbazolybiphenyl). In addition, when the compound represented by Formula 1 is included in an organic material layer such as an electron transport layer, since it is effective in suppressing crystallization of the organic material layer due to the various aromatic ring substituents, the organic EL device including the compound has great durability and lifespan characteristics. can be improved

Accordingly, the organic electroluminescent device according to the present invention includes the compound represented by Formula 1 as a first organic material layer material between the cathode and the light emitting layer, preferably the first organic material layer material between the electron transport layer and the light emitting layer, or as an electron transport layer material, Luminous efficiency, driving voltage, and lifespan may be improved. As such, the organic electroluminescent device of the present invention with improved performance and lifespan can maximize the performance of the full color organic light emitting panel as a result.

The organic electroluminescent device of the present invention has a structure in which one or more organic material layers and a cathode are sequentially stacked on an anode, and will be described with reference to FIGS. 1 and 2 as follows.

The anode 100 of the present invention is an electrode for injecting holes into the organic material layer 300 , particularly the hole injection layer 301 . The material forming the anode is not particularly limited, and examples thereof include metals such as vanadium, chromium, copper, zinc, and gold; alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal such as ZnO:Al, SnO _{2 :Sb and an oxide;} conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, and polyaniline; and carbon black.

Such an anode may be formed by coating the anode material on a substrate through a known thin film forming method such as a sputtering method, an ion plating method, a vacuum deposition method, or a spin coating method.

The substrate (not shown) is a plate-shaped member for supporting the organic electroluminescent device, and includes, for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet, but is not limited thereto.

The cathode 200 of the present invention is an electrode for injecting electrons into the organic material layer 300 , in particular, the electron injection layer 306 or the electron transport layer 303 . The material forming the negative electrode is not particularly limited, and examples thereof include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; alloys thereof; and a multilayer structure material such as LiF/Al, LiO ₂ /Al, and the like.

Such a negative electrode, like the positive electrode, may be formed by coating the negative electrode material through a thin film forming method known in the art.

In the present invention, the at least one organic material layer 300 includes a light emitting layer 301; and a first organic material layer 302 which is positioned between the light emitting layer 301 and the cathode 200 and is represented by Chemical Formula 1 above.

According to one example, as described above, the first organic material layer 302 is an electron transport auxiliary layer that effectively moves electrons transferred from the electron transport layer to the light emitting layer between the light emitting layer and the electron transport layer due to the compound of Formula 1 having strong electron transport properties. can play the role of In this case, the at least one organic material layer 300 includes a light emitting layer 301 , a first organic material layer 302 and an electron transport layer 303 , in addition to a hole injection layer 304 , a hole transport layer 305 and an electron injection layer. 306 may be further included.

1, on the anode 100, a hole injection layer 304, a hole transport layer 305, a light emitting layer 301, a first organic material layer 302, an electron transport layer 303, an electron injection layer ( 306) and the cathode 200 may be sequentially stacked. In some cases, an insulating layer (not shown) or an adhesive layer (not shown) may be inserted at the interface between the electrode and each organic material layer.

According to another example, the first organic material layer 302 is formed of the compound of Formula 1, which is an electron transporting compound, so that the electrons injected from the cathode are moved between the light emitting layer 301 and the cathode 200 toward the light emitting layer. can do. In this case, the at least one organic material layer 300 includes a light emitting layer 301 and a first organic material layer 302, and further includes a hole injection layer 304, a hole transport layer 305, and an electron injection layer 306. can do.

As shown in FIG. 2 , the anode 100 , the hole injection layer 304 , the hole transport layer 305 , the emission layer 301 , the first organic material layer 302 , the electron injection layer 306 and the cathode 200 . These may be sequentially stacked. In some cases, an insulating layer (not shown) or an adhesive layer (not shown) may be inserted at the interface between the electrode and each organic material layer.

As such, since the organic electroluminescent device of the present invention includes the first organic material layer 302, electron movement to the light emitting layer 301 is smooth, thereby increasing the exciton formation efficiency in the light emitting layer, thereby improving light emitting performance. This can be achieved, the driving voltage is low, the current efficiency is high, and the lifespan can be increased.

The first organic material layer 302 of the present invention includes the compound represented by Formula 1 above.

In the compound represented by Formula 1, Cy1 and Cy2 are the same as or different from each other, and are each independently _{selected from the group consisting of a C 6} ~ C ₄₀ aromatic ring and a heteroaromatic ring having 5 to 40 nuclear atoms.

In this case, the C ₆ ~ C ₄₀ aromatic ring of Cy1 and Cy2, and the heteroaromatic ring having 5 to 40 nuclear atoms are each independently deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ C ₄₀ from the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ arylsilyl group the group consisting of C ₄₀ of It is substituted or unsubstituted with one or more selected substituents, and in this case, when the substituents are plural, they may be the same as or different from each other.

Non-limiting examples of the C ₆ ~ C ₄₀ aromatic ring include benzene, indene, naphthalene, fluorene, anthracene, phenanthrene, naphthacene, pyrene, triphenylene, etc., which are each independently deuterium (D ), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 nuclear atoms hetero Aryl group, C ₆ ~ C ₄₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 nuclear atoms hetero Cycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Aryl It is substituted or unsubstituted with one or more substituents selected from the group consisting of a phosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group, and in this case, when the substituents are plural, they may be the same or different from each other.

In addition, non-limiting examples of the heteroaromatic ring having 5 to 40 nuclear atoms include furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, triazole, thiazole, oxadiazole. , pyridine, pyrimidine, triazine, indole, benzofuran, benzothiophene, benzoimidazole, benzothiazole, purine, quinoline, isoquinoline, quinoxaline, carbazole, dibenzothiophene, dibenzofuran, acryl There are din, phenanthroline, etc., these are deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl group, the group alkyl boronic of C ₁ ~ C _40, an aryl boronic a _{C 6 ~ C 40, C 6} ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and C ₆ ~ C ₄₀ arylsilyl group is substituted or unsubstituted with one or more substituents selected from the group consisting of, wherein the substituents are plural , they may be the same as or different from each other.

Preferably, Cy1 and Cy2 are the same as or different from each other, and each independently may be selected from the group consisting of benzene, thiophene and thianoindole, and more preferably benzene.

For example, when both Cy1 and Cy2 are benzene, the compound of Formula 1 may be represented by Formula 2 below.

In Formula 2,

X ₁ , X ₂ and R ₁ to R ₄ are each as defined in Formula 1;

a is an integer of 0 to 4, and when a is 0, _{it means that hydrogen is not substituted with R 5} , and when a is an integer of 1 to 4, one or more R ₅ are each independently deuterium (D) , halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl of 5 to 40 nuclear atoms group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocyclo of 3 to 40 nuclear atoms alkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine It is selected from the group consisting of a fin oxide group and a C ₆ ~ C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

b is an integer of 0 to 4, and when b is 0, _{it means that hydrogen is not substituted with R 6} , and when b is an integer of 1 to 4, one or more R ₆ are each independently deuterium (D) , halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl of 5 to 40 nuclear atoms group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocyclo of 3 to 40 nuclear atoms alkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine It may be selected from the group consisting of a fin oxide group and a C ₆ ~ C ₄₀ arylsilyl group, or combined with an adjacent group to form a condensed ring.

In Formula 1, R _{1 To} R _{4 Are} the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups of binding to the the to form a condensed ring.

Preferably, considering the HOMO, LUMO, band-gap and thermal stability of the compound, R _{1 To} R _{4 Are} the same as or different from each other, and each independently hydrogen, C ₆ ~ C ₄₀ An aryl group (such as , a phenyl group, a naphthyl group, a bisphenyl group, etc.) and a heteroaryl group having 5 to 40 nuclear atoms (eg, a pyridine group, a pyrimidine group, a triazine group, a quinazoline group, etc.).

In this case, the R _{1 To} R ₄ C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, the number of nuclear atoms 5 to 40 of heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms of heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ of arylphosphine oxide group and C ₆ ~ C ₄₀ arylsilyl group are each independently deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one substituent at least one selected from an aryl silyl group consisting of C ₄₀ unsubstituted in and, when the substituents are plural, they may be the same as or different from each other.

In Formula 1, X ₁ and X ₂ are the same as or different from each other, and each independently O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar _{5 )} ), provided that at least one of _{X 1} and X _{2 is N(Ar 1} ), and in this _{case, when Ar 1} is plural, they are the same or different from each other.

Preferably, X ₁ and X ₂ may be each independently selected from the group consisting of O, S, N(Ar ₁ ) and C(Ar ₂ )(Ar ₃ ), provided that at least one of _{X 1} and X _{2 is} N(Ar ₁ ) _{, wherein when Ar 1} is a plurality, they are the same as or different from each other.

According to one example, when one of X ₁ and X ₂ is N(Ar ₁ ) and the other is C(Ar ₂ )(Ar ₃ ), Ar ₁ may be a substituent represented by the following Chemical Formula 3, Ar ₂ and Ar ₃ may be the same as or different from each other, and may each independently be a methyl group or a phenyl group.

According to another example, when one of X ₁ and X ₂ is N(Ar ₁ ) and the other is O or S, Ar ₁ may be a substituent represented by Formula 3 below.

According to another example, _{when both X 1} and X ₂ are N(Ar ₁ ), one of the plurality of Ar ₁ may be a substituent represented by the following Chemical Formula 3, and the rest may be a methyl group, a phenyl group, or a pyridine group.

The Ar _{1 To} Ar _{5 Are} the same as or different from each other, and each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cyclo Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₄₀ arylboron group, C ₆ to C ₄₀ aryl A phosphine group, a C ₆ ~ C ₄₀ arylphosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group are selected from the group consisting of.

Preferably, the Ar ₁ to Ar ₅ are the same as or different from each other, and each independently _{selected from the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, and a heteroaryl group of 5 to 40 nuclear atoms. can be

More preferably, Ar ₁ may be a substituent represented by the following Chemical Formula 3 or a phenyl group.

In Formula 3,

* means a moiety bonded to Formula 1;

L 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, preferably a single bond, or a phenylene group or a biphenylene group;

Z _{1 To} Z _{5 Are} the same as or different from each other, and each independently is N or C(R ₁₁ ), provided that Z _{1 To} Z ₅ at least one of them is N, wherein when R ₁₁ is plural, they are the same as or different from each other;

R ₁₁ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ Aryloxy group C ₁ to C ₄₀ Alkyloxy group, C ₃ to C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Aryl phosphine oxide group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or is _{combined with an adjacent group (eg, L, other adjacent R 11} ) to form a condensed ring. can;

In this case, R ₁₁ is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently 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 ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ substituted with an aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group and one substituent at least one selected from the group consisting arylsilyl of C ₆ ~ C ₄₀ of or is unsubstituted, In this case, when the substituents are plural, they may be the same as or different from each other.

Examples of the substituent represented by Formula 3 include, but are not limited to, the ring body represented by the following A-1 to A-15.

In the above A-1 to A-15,

L and R ₁₁ are each as defined in Formula 3 above,

n is an integer of 0 to 4, and when n is 0, _{it means that hydrogen is not substituted with a substituent R 12} , and when n is an integer of 1 to 4, R ₁₂ is hydrogen, deuterium, halogen, or a 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 ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl group, C ₆ ~ C _{40 60} aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Aryl phosphine group, C ₆ ~ C ₄₀ Aryl phosphine oxide A group and a C ₆ ~ C ₄₀ may be selected from the group consisting of an arylsilyl group, or _{combined with an adjacent group (eg, L, R 11} or other R _12, etc.) to form a condensed ring,

In this case, R ₁₂ is an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently 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 ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ substituted with an aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group and one substituent at least one selected from the group consisting arylsilyl of C ₆ ~ C ₄₀ of or is unsubstituted, When the substituents are plural, they may be the same as or different from each other.

The compound represented by Formula 1 may be embodied as the following compounds Inv-1 to Inv-200, and the like, but is not limited thereto.

Meanwhile, "alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl. , hexyl, and the like.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond, and examples thereof include ethynyl, 2-propynyl and the like.

"Aryl" in the present invention means 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 phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, it is interpreted to include a form in which two or more rings are simply attached to each other or fused to each other, and further includes a form condensed with an aryl group. 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, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

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 phenyloxy, naphthyloxy, diphenyloxy and the like.

"Alkyloxy" in the present invention is a monovalent substituent represented by R'O-, wherein R' means 1 to 40 alkyl, and has a linear, branched or cyclic structure. interpreted as including Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with an aryl having 6 to 40 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention 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, substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like.

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.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compound of Formula 1 according to the present invention can be synthesized in various ways with reference to the following synthesis examples. The detailed synthesis process for the compound of the present invention will be described in detail in the following Synthesis Examples.

One or more organic material layers 300 according to the present invention include a light emitting layer 301 . The light emitting layer 301 is a layer in which holes and electrons meet to form excitons, and the color of light emitted from the organic electroluminescent device may vary depending on a material forming the light emitting layer. The light emitting layer may include a host and a dopant, and a mixing ratio of the host and the dopant may be 70 to 99.9: 0.1 to 30 by weight.

According to one example, when the emission layer 301 is blue fluorescent, green fluorescent, or red fluorescent, the host may be included in an amount of 80 to 99.9 wt%, and the dopant may be included in an amount of 0.1 to 20 wt%.

According to another example, when the emission layer 301 is blue fluorescence, green fluorescence, or red fluorescence, the host may be included in an amount of 70 to 99% by weight, and the dopant may be included in an amount of 1 to 30% by weight.

The host is not particularly limited as long as it is known in the art, and for example, an alkali metal complex; alkaline earth metal complexes; or a condensed aromatic ring derivative, and the like, but is not limited thereto. In particular, examples of the host that can increase the luminous efficiency and lifespan of the organic EL device include aluminum complex compounds, beryllium complexes, anthracene derivatives, pyrene derivatives, triphenylene derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, etc.

The dopant is not particularly limited as long as it is known in the art, and for example, an anthracene derivative; pyrene derivatives; arylamine derivatives; There are metal complex compounds containing heavy atoms such as iridium (Ir) and platinum (Pt), but is not limited thereto.

The light emitting layer 301 may be manufactured by a conventional light emitting layer forming method known in the art. For example, there are a co-evaporation method, a vacuum evaporation method, a solution coating method, and the like.

Meanwhile, the one or more organic material layers 300 according to the present invention may further include a hole injection layer 304 as shown in FIGS. 1 and 2 . The hole injection layer 304 is formed between the anode 100 and the light emitting layer 301 or between the anode 100 and the hole transport layer 305 to transport holes injected from the anode 100 into the light emitting layer 301 or the hole transport layer. It serves to move to (305). The material forming the hole injection layer is not particularly limited as long as it is a material capable of well accepting holes from the anode at a low voltage. However, in order to control the difference between the work function level of the anode and the HOMO energy level of the light emitting layer, it is preferable to use a material having a HOMO energy level intermediate between the work function level of the anode and the HOMO energy level of the light emitting layer as the hole injection layer material. .

Non-limiting examples of the material for the hole injection layer include metal porphyrine, oligothiophene, arylamine-based derivatives, hexanitrile hexaazatriphenylene-based derivatives, quinacridone-based derivatives, and perylene-based derivatives. based) derivatives, or conductive polymers such as anthraquinone derivatives, polyaniline derivatives, and polythiophene derivatives.

In addition, one or more organic material layers 300 according to the present invention may further include a hole transport layer 305 . The hole transport layer 305 is formed between the anode 100 and the light emitting layer 301 or between the hole injection layer 304 and the light emitting layer 301 to move holes injected from the anode or the hole injection layer to the light emitting layer. . The material for forming the hole transport layer is not particularly limited as long as it is a material having high hole mobility. However, since the hole mobility of the hole transport layer affects the charge balancing effect, the HOMO energy level is the work function level of the anode or the intermediate value between the HOMO energy level of the hole injection layer and the HOMO energy level of the light emitting layer. It is preferable to use it as

Examples of the hole transport layer material include, but are not limited to, an arylamine-based derivative, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

In addition, the one or more organic material layer 300 according to the present invention may further include a separate electron transport layer 303 only when the above-described first organic material layer serves as an electron transport auxiliary layer. The electron transport layer 303 is formed between the first organic material layer 302 and the cathode 200 or between the first organic material layer 302 and the electron injection layer 306 to transport electrons injected from the cathode or the electron injection layer. It serves to move toward the light emitting layer. The material for forming the electron transport layer is not particularly limited as long as it is a material having high mobility with respect to electrons from the cathode.

Examples of the electron transport layer include an Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.

In addition, the one or more organic material layers 300 according to the present invention may further include an electron injection layer 306 . The electron injection layer 306 is formed between the first organic material layer 302 and the cathode 200 or between the electron transport layer and the cathode to move electrons injected from the cathode toward the emission layer. The material for forming the electron injection layer is not particularly limited as long as it is a material that can easily accept electrons from the cathode.

Examples of the electron injection layer material include alkali metals, alkaline earth metals, and halides, oxides, peroxides, and sulfides thereof, and specifically, alkali metals such as Ce and Li, alkaline earth metals such as Ca, Sr, Ba, and Ra; fluorides such as lithium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, and barium fluoride; and oxides such as lithium oxide. Among these, LiF is preferable.

The above-described hole injection layer/transport layer and electron injection layer/transport layer may be formed by a vacuum deposition method or a solution coating method like the light emitting layer. Non-limiting examples of the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of compound IC-1

<Step 1> Synthesis of 2-chloro-1-phenyl-1H-indole

Under a nitrogen stream, 1-phenylindolin-2-one (75 g, 358.44 mmol) was added to MC (1000 ml) and stirred, and then _{POCl 3} (196.87 ml, 2.15 mol) was slowly added dropwise, and then at 40 °C for 12 hours. stirred.

After the reaction was slowly added dropwise to water (2 L), the mixture was stirred for 3 hours. After the reaction was completed, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 5:1 (v/v)) to obtain 2-chloro-1-phenyl-1H-indole (28.56 g, yield 35%).

¹ H-NMR: δ 6.62 (s, 1H), 7.15 (m, 3H), 7.41 (d, 2H), 7.49 (d, 1H), 7.58 (m, 3H)

<Step 2> Synthesis of 2-(phenanthren-9-yl)-1-phenyl-1H-indole

2-chloro-1-phenyl-1H-indole (25 g, 109.80 mmol), phenanthren-9-ylboronic acid (29.26 g, 131.76 mmol), Pd(OAc) ₄ (1.23) obtained in <Step 1> under a nitrogen stream g, 5 mol%), XPhos (7.85 g, 16.47 mmol), CsCO ₃ (71.55 g, 219.60 mmol) and Toluene/ethanol/H ₂ O (400 ml/50 ml/50 ml) were mixed, and then 110 ° C. was stirred for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 2:1 (v/v)) and 2-(phenanthren-9-yl)-1-phenyl-1H-indole (24.75 g, yield 61) %) was obtained.

¹ H-NMR: δ 6.88 (s, 1H), 7.07 (t, 1H), 7.15 (t, 2H), 7.24 (m, 4H), 7.43 (m, 2H), 7.57 (m, 2H), 7.64 ( t, 1H), 7.71 (s, 1H), 7.77 (m, 2H), 7.97 (d, 1H), 8.64 (d, 2H)

<Step 3> Synthesis of 3-nitroso-2-(phenanthren-9-yl)-1-phenyl-1H-indole

2-(phenanthren-9-yl)-1-phenyl-1H-indole (20 g, 54.13 mmol) obtained in <Step 2> above under a nitrogen stream was put in THF (400 ml), and after lowering to 0 ℃ 2, 2,2-trifluoroacetic acid (20.73 ml, 270.67 mmol) was slowly added dropwise. Thereafter, while maintaining the reaction temperature at 0° C., _{NaNO 2 (7.47 g, 108.27 mmol) dissolved in H 2} O (30 ml) was slowly added dropwise, followed by stirring for 1 hour.

After completion of the reaction, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 1:1 (v/v)) to 3-nitroso-2-(phenanthren-9-yl)-1-phenyl-1H-indole ( 11.65 g, yield 54%) was obtained.

¹ H-NMR: δ 7.22 (d, 1H), 7.29 (d, 1H), 7.34 (m, 2H), 7.44 (m, 1H), 7.52 (m, 2H), 7.61 (m, 2H), 7.65 ( d, 2H), 7.79 (m, 1H), 7.87 (d, 1H), 8.01 (d, 1H), 8.21 (d, 1H), 8.46 (s, 1H), 8.84 (m, 2H)

<Step 4> Synthesis of compound IC-1

3-nitroso-2-(phenanthren-9-yl)-1-phenyl-1H-indole (10 g, 25.10 mmol), P(OEt) ₃ (20.85 g, 125.48 mmol) obtained in <Step 3> under a nitrogen stream ), and Toluene (100 ml) were mixed, followed by stirring at 110 °C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 1:1 (v/v)) to obtain compound IC-1 (5.57 g, yield 58%).

¹ H-NMR: δ 6.97 (d, 1H), 7.04 (m, 1H), 7.24 (m, 3H), 7.35 (t, 1H), 7.61 (m, 6H), 7.71 (m, 1H), 7.90 ( d, 1H), 8.52 (d, 1H), 8.73 (d, 1H), 8.78 (d, 1H), 12.59 (s, 1H)

[Preparation Example 2] Synthesis of compound IC-2

<Step 1> Synthesis of 3-nitro-2-(phenanthren-9-yl)benzo[b]thiophene

2-bromo-3-nitrobenzo[b]thiophene (30 g, 116.24 mmol), phenanthren-9-ylboronic acid (28.39 g, 127.86 mmol), K ₂ CO ₃ (48.20 g, 348.72 mmol) and Toluene/ Ethanol/H ₂ O (300 ml/80 ml/80 ml) was mixed, and then Pd(PPh ₃ ) ₄ (6.72 g, 5 mol%) was added at 40° C. and stirred at 110° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 2:1 (v/v)) and 3-nitro-2-(phenanthren-9-yl)benzo[b]thiophene (19.83 g, yield) 48%) was obtained.

¹ H-NMR: δ 7.38 (t, 1H), 7.54 (t, 1H), 7.61 (m, 2H), 7.76 (d, 1H), 7.79 (d, 1H), 8.07 (d, 1H), 8.08 ( d, 1H), 8.17 (d, 1H), 8.45 (s, 1H), 8.50 (d, 1H), 8.85 (d, 1H), 8.87 (d, 1H)

<Step 2> Synthesis of compound IC-2

3-nitro-2-(phenanthren-9-yl)benzo[b]thiophene (17.8 g, 50.08 mmol), triphenylphosphine (32.84 g, 125.21 mmol) and 1,2-dichlorobenzene obtained in <Step 1> under a nitrogen stream (200 ml) was mixed and stirred for 12 h.

After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. After water was removed from the obtained organic layer with MgSO _{4 , it} was purified by column chromatography (Hexane:MC = 1:1 (v/v)) to obtain compound IC-2 (13.06 g, yield 56%).

¹ H-NMR: δ 7.38 (t, 1H), 7.54 (t, 1H), 7.61 (m, 2H), 7.76 (d, 1H), 7.79 (d, 1H), 8.07 (d, 1H), 8.08 ( d, 1H), 8.17 (d, 1H), 8.50 (d, 1H), 8.85 (d, 1H), 8.87 (d, 1H), 13.07 (s, 1H)

[Preparation Example 3] Synthesis of compound IC-3

<Step 1> Synthesis of 2-bromo-1H-dibenzo[e,g]indole

2,3,5-tribromo-1H-pyrrole (20 g, 65.84 mmol), 5,5-dimethyl-5H-dibenzo[b,d]stannole (19.81 g, 65.84 mmol), Pd(PtBu ₃ ) under a nitrogen stream ₂ (1.68 g, 3.29 mmol), CsF (50.00 g, 329.19 mol) and THF (500 ml) were mixed and stirred at 60° C. for 12 hours.

After completion of the reaction, the temperature was lowered to room temperature, the reaction product was filtered through Florisil, the solvent was removed, and purified by column chromatography (Hexane:MC = 10:1 (v/v)) to 2-bromo- 1H-dibenzo[e,g]indole (6.04 g, yield 31%) was obtained.

¹ H-NMR: δ 7.63 (m, 4H), 7.82 (s, 1H), 7.92 (d, 1H), 8.13 (d, 1H), 8.61 (d, 2H), 11.30 (s, 1H)

<Step 2> 2-(2- nitrophenyl )-1H- dibenzo Synthesis of [e,g]indole

2-bromo-1H-dibenzo[e,g]indole (6 g, 20.26 mmol) instead of 2-bromo-3-nitrobenzo[b]thiophene (30 g, 116.24 mmol) used in <Step 1> of Preparation Example 2 ), and using 2-nitrophenylboronic acid (4.06 g, 24.31 mmol) instead of phenanthren-9-ylboronic acid (28.39 g, 127.86 mmol), the same procedure as <Step 1> of Preparation Example 2 to obtain 2-(2-nitrophenyl)-1H-dibenzo[e,g]indole (4.04 g, yield 59%).

¹ H-NMR: δ 7.43 (t, 1H), 7.62 (m, 5H), 7.75 (m, 2H), 7.85 (d, 1H), 7.94 (d, 1H), 8.15 (d, 1H), 8.63 ( d, 2H), 11.28 (s, 1H)

<Step 3> Synthesis of 2-(2-nitrophenyl)-1-phenyl-1H-dibenzo[e,g]indole

2-(2-nitrophenyl)-1H-dibenzo[e,g]indole (4 g, 11.82 mmol), iodobenzene (3.62 g, 17.73 mmol), Cu powder (0.08 g, 1.18 mmol), K ₂ CO ₃ (1.63 g, 11.82 mmol), Na ₂ SO ₄ (1.68 g, 11.82 mmol), and nitrobenzene (50 ml) were mixed and stirred at 200° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent from the water-removed organic layer, it was purified by column chromatography (Hexane:MC = 3:1 (v/v)) to 2-(2-nitrophenyl)-1-phenyl-1H-dibenzo[e,g] Indole (2.06 g, yield 42%) was obtained.

¹ H-NMR: δ 7.42 (m, 2H), 7.51 (t, 2H), 7.60 (m, 7H), 7.72 (m, 2H), 7.83 (d, 1H), 7.91 (d, 1H), 8.13 ( d, 1H), 8.62 (d, 2H)

<Step 4> Synthesis of compound IC-3

2-(2-(2-) obtained in <Step 3> instead of 3-nitro-2-(phenanthren-9-yl)benzo[b]thiophene (17.8 g, 50.08 mmol) used in <Step 2> of Preparation Example 2 Except for using nitrophenyl)-1-phenyl-1H-dibenzo[e,g]indole (2 g, 4.83 mmol), the same procedure as in <Step 2> of Preparation Example 2 was performed to compound IC-3 (1.11 g, yield 60%) was obtained.

¹ H-NMR: δ 7.41 (m, 2H), 7.50 (t, 2H), 7.59 (m, 7H), 7.70 (d, 1H), 7.81 (d, 1H), 7.92 (d, 1H), 8.14 ( d, 1H), 8.63 (d, 2H), 11.32 (s, 1H)

[Preparation Example 4] Synthesis of compound IC-4

<Step 1> Synthesis of 2-bromophenanthro[9,10-b]thiophene

Except for using 2,3,5-tribromothiophene (20 g, 62.34 mmol) instead of 2,3,5-tribromo-1H-pyrrole (20 g, 65.84 mmol) used in <Step 1> of Preparation Example 3 and 2-bromophenanthro[9,10-b]thiophene (6.25 g, yield 32%) was obtained by performing the same process as <Step 1> of Preparation Example 3.

¹ H-NMR: δ 7.61 (m, 4H), 7.88 (s, 1H), 7.94 (d, 1H), 8.15 (d, 1H), 8.65 (d, 2H)

<Step 2> Synthesis of 2-(2-nitrophenyl)phenanthro[9,10-b]thiophene

Instead of 2-bromo-3-nitrobenzo[b]thiophene (30 g, 116.24 mmol) used in <Step 1> of Preparation Example 2, 2-bromophenanthro[9,10-b]thiophene (6 g, 19.16 mmol) Except for using 2-nitrophenylboronic acid (3.84 g, 22.99 mmol) instead of phenanthren-9-ylboronic acid (28.39 g, 127.86 mmol), the same procedure as in Preparation Example 2 <Step 1> was performed. 2-(2-nitrophenyl)phenanthro[9,10-b]thiophene (4.29 g, yield 63%) was obtained.

¹ H-NMR: δ 7.41 (t, 1H), 7.63 (m, 5H), 7.73 (s, 1H), 7.75 (d, 1H), 7.85 (d, 1H), 7.92 (d, 1H), 8.14 ( d, 1H), 8.62 (d, 2H)

<Step 3> Synthesis of compound IC-4

2-(2-(2-) obtained in <Step 2> instead of 3-nitro-2-(phenanthren-9-yl)benzo[b]thiophene (17.8 g, 50.08 mmol) used in <Step 2> of Preparation Example 2 Except for using nitrophenyl) phenanthro[9,10-b]thiophene (4 g, 11.25 mmol), the same procedure as in <Step 2> of Preparation Example 2 was performed, and compound IC-4 (2.04 g, yield) 56%) was obtained.

¹ H-NMR: δ 7.37 (m, 2H), 7.62 (m, 5H), 7.89 (d, 1H), 7.91 (d, 1H), 8.12 (d, 1H), 8.60 (d, 2H), 11.32 ( s, 1H)

[Preparation Example 5] Synthesis of compound IC-5

3,3-dimethyl-2,3-dihydro-1H-inden-1-one (10 g, 62.42 mmol), phenanthren-9-ylhydrazine hydrochloride (15.27 g, 62.42 mmol), NMP (100 ml) The mixture was mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, NMP was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After the solvent was removed from the organic layer from which water was removed, it was purified by column chromatography (Hexane:MC = 1:1 (v/v)) to obtain compound IC-5 (10.61 g, yield 51%).

¹ H-NMR: δ 1.70 (s, 6H), 7.54 (m, 2H), 7.61 (m, 5H), 7.90 (d, 1H), 7.95 (d, 1H), 8.14 (d, 1H), 8.62 ( d, 2H), 11.35 (s, 1H)

[Preparation Example 6] Synthesis of compound IC-6

Instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (10 g, 62.42 mmol) used in the above preparation example, benzofuran-3(2H)-one (10 g, 74.55 mmol) was used. Except for that, the same procedure as in Preparation Example 5 was performed to obtain compound IC-6 (9.62 g, yield 42%).

¹ H-NMR: δ 7.41 (m, 2H), 7.60 (m, 5H), 7.86 (d, 1H), 7.92 (d, 1H), 8.11 (d, 1H), 8.61 (d, 2H), 11.33 ( s, 1H)

[Synthesis Example 1] Synthesis of compound Inv-3

Compound IC-1 (5 g, 13.07 mmol), 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol), Pd ₂ (dba ₃ ) (1.20 g, 1.31 mmol) synthesized in Preparation Example 1 under a nitrogen stream ), NaO(t-bu) (3.77 g, 39.22 mmol), P(t-bu) ₃ (0.26 g, 1.31 mmol) and Xylene (150 ml) were mixed and stirred at 140 °C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane _{, water was removed with MgSO 4} , and purified by column chromatography (Hexane:MC = 3:1 (v/v)) to compound Inv-3 (5.37 g, yield 67%) was obtained.

GC-Mass (theoretical: 612.23 g/mol, measured: 612 g/mol)

[Synthesis Example 2] Synthesis of compound Inv-4

Except for using 4-chloro-2,6-diphenylpyrimidine (3.84 g, 14.38 mmol) instead of 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) used in Synthesis Example 1, the above synthesis The same procedure as in Example 1 was followed to obtain compound Inv-4 (4.97 g, yield 62%).

GC-Mass (theoretical: 612.23 g/mol, measured: 612 g/mol)

[ Synthesis example 3] compound Inv -5 synthesis

Compound IC-1 (5 g, 13.07 mmol) synthesized in Preparation Example 1 was dissolved in DMF (150 ml) under nitrogen, and NaH (0.78 g, 32.68 mmol) was added thereto and stirred for 1 hour. To this, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.70 g, 26.15 mmol) dissolved in DMF (200ml) was slowly added. After stirring for 5 hours, the reaction was terminated, and the mixture was filtered through silica, washed with water and methanol, and the solvent was removed. The solid product from which the solvent was removed was purified by column chromatography (Hexane:MC = 1:3 (v/v)) to obtain compound Inv-5 (4.65 g, yield 58%).

GC-Mass (theoretical: 613.23 g/mol, measured: 613 g/mol)

[Synthesis Example 4] Synthesis of compound Inv-8

Synthesis Example 1, except for using 2-(4-chlorophenyl)pyrimidine (2.74 g, 14.38 mmol) instead of 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) used in Synthesis Example 1 The same procedure was followed to obtain compound Inv-8 (4.28 g, yield 61%).

GC-Mass (theoretical: 536.20 g/mol, measured: 536 g/mol)

[Synthesis Example 5] Synthesis of compound Inv-18

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of Compound Inv-18 (4.68 g, yield 65%) was carried out in the same manner as in Synthesis Example 1, except that 2-(4-chlorophenyl)-4,6-diphenylpyrimidine (3.94 g, 11.50 mmol) was used. got

GC-Mass (theoretical: 688.26 g/mol, measured: 688 g/mol)

[Synthesis Example 6] Synthesis of compound Inv-19

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of Except for using 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (3.94 g, 11.50 mmol), the same procedure as in Synthesis Example 1 was performed to compound Inv-19 (4.47 g, yield 62%) got

GC-Mass (theoretical: 688.26 g/mol, measured: 688 g/mol)

[Synthesis Example 7] Synthesis of compound Inv-20

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.96 g, 11.50 mmol) was carried out in the same manner as in Synthesis Example 1, except that compound Inv-20 (4.83 g, yield 67%) was obtained.

GC-Mass (theoretical: 689.26 g/mol, measured: 689 g/mol)

[Synthesis Example 8] Synthesis of compound Inv-23

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of Compound Inv-23 (4.61 g, yield 64%) was performed in the same manner as in Synthesis Example 1, except that 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (3.94 g, 11.50 mmol) was used. got

GC-Mass (theoretical: 688.26 g/mol, measured: 688 g/mol)

[Synthesis Example 9] Synthesis of compound Inv-24

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of Compound Inv-24 (4.54 g, yield 63%) was performed in the same manner as in Synthesis Example 1, except that 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (3.94 g, 11.50 mmol) was used. got

GC-Mass (theoretical: 688.26 g/mol, measured: 688 g/mol)

[Synthesis Example 10] Synthesis of compound Inv-25

Compound IC-1 (4 g, 10.46 mmol) was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84 g, 14.38 mmol) was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.96 g, 11.50 mmol) was carried out in the same manner as in Synthesis Example 1, except that compound Inv-25 (5.12 g, yield 71%) was obtained.

GC-Mass (theoretical: 689.26 g/mol, measured: 689 g/mol)

[Synthesis Example 11] Synthesis of compound Inv-28

Compound IC-2 (5 g, 15.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-chloro-4,6-diphenylpyrimidine (4.54 g, 17.01 mmol), except for using the compound Inv-28 (5.48 g, yield 64) in the same manner as in Synthesis Example 1 %) was obtained.

GC-Mass (theoretical: 553.16 g/mol, measured: 553 g/mol)

[Synthesis Example 12] Synthesis of compound Inv-29

Compound IC-2 (5 g, 15.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 4-chloro-2,6-diphenylpyrimidine (4.54 g, 17.01 mmol), except for using the compound Inv-29 (5.65 g, yield 66) in the same manner as in Synthesis Example 1 %) was obtained.

GC-Mass (theoretical: 553.16 g/mol, measured: 553 g/mol)

[Synthesis Example 13] Synthesis of compound Inv-30

Compound IC-2 (5 g, 15.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 3, and 2-chloro-4,6-diphenyl-1 Synthesis Example 3, except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (8.28 g, 30.92 mmol) instead of ,3,5-triazine (6.70 g, 26.15 mmol) The same procedure was followed to obtain compound Inv-30 (4.63 g, yield 54%).

GC-Mass (theoretical: 554.16 g/mol, measured: 554 g/mol)

[Synthesis Example 14] Synthesis of compound Inv-33

Compound IC-2 (5 g, 15.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-(4-chlorophenyl)pyrimidine (3.24 g, 17.01 mmol), except for using the compound Inv-33 (3.62 g, yield 49%) in the same manner as in Synthesis Example 1 above. ) was obtained.

GC-Mass (theoretical: 477.13 g/mol, measured: 477 g/mol)

[Synthesis Example 15] Synthesis of compound Inv-35

Compound IC-2 (5 g, 15.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-chloro-5-phenylpyrimidine (3.24 g, 17.01 mmol), except for using the compound Inv-35 (3.47 g, yield 47%) in the same manner as in Synthesis Example 1 above) got

GC-Mass (theoretical: 477.13 g/mol, measured: 477 g/mol)

[Synthesis Example 16] Synthesis of compound Inv-38

Compound IC-2 (4 g, 10.46 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) in the same manner as in Synthesis Example 1, except that 2-(4-chlorophenyl)-5-phenylpyrimidine (3.84 g, 12.37 mmol) was used instead of compound Inv-38 (4.45 g, Yield 65%) was obtained.

GC-Mass (theoretical: 553.16 g/mol, measured: 553 g/mol)

[Synthesis Example 17] Synthesis of compound Inv-43

The compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) in the same manner as in Synthesis Example 1, except that 2-(4-chlorophenyl)-4,6-diphenylpyrimidine (4.66 g, 13.61 mmol) was used instead of compound Inv-43 (5.45). g, yield 70%) was obtained.

GC-Mass (theoretical: 629.19 g/mol, measured: 629 g/mol)

[Synthesis Example 18] Synthesis of compound Inv-44

Compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol), except that 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (4.66 g, 13.61 mmol) was used instead of the compound Inv-44 (5.61) in the same manner as in Synthesis Example 1 g, yield 72%) was obtained.

GC-Mass (theoretical: 629.19 g/mol, measured: 629 g/mol)

[Synthesis Example 19] Synthesis of compound Inv-45

Compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.67 g, 13.61 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain compound Inv-45 (5.38 g, yield 69%).

GC-Mass (theoretical: 630.19 g/mol, measured: 630 g/mol)

[Synthesis Example 20] Synthesis of compound Inv-48

Compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) in the same manner as in Synthesis Example 1, except that 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (4.66 g, 13.61 mmol) was used instead of Compound Inv-48 (4.99) g, yield 64%) was obtained.

GC-Mass (theoretical: 629.19 g/mol, measured: 629 g/mol)

[Synthesis Example 21] Synthesis of compound Inv-49

Compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (4.66 g, 13.61 mmol), the same procedure as in Synthesis Example 1 was performed, except that compound Inv-49 (5.06 g, yield 65%) was obtained.

GC-Mass (theoretical: 629.19 g/mol, measured: 629 g/mol)

[Synthesis Example 22] Synthesis of compound Inv-50

Compound IC-2 (4 g, 12.37 mmol) synthesized in Preparation Example 2 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.68 g, 13.61 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain compound Inv-50 (5.54 g, yield 71%).

GC-Mass (theoretical: 630.19 g/mol, measured: 630 g/mol)

[Synthesis Example 23] Synthesis of compound Inv-53

The same procedure as in Synthesis Example 1 was followed, except that IC-3 (5 g, 13.07 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1 was carried out to obtain the compound Inv-53 (5.21 g, yield 65%).

GC-Mass (theoretical: 612.23 g/mol, measured: 612 g/mol)

[Synthesis Example 24] Synthesis of compound Inv-54

Compound IC-3 (5 g, 13.07 mmol) synthesized in Preparation Example 3 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 4-chloro-2,6-diphenylpyrimidine (3.84 g, 14.38 mmol), except for using the compound Inv-54 (5.45 g, yield 68) in the same manner as in Synthesis Example 1 %) was obtained.

GC-Mass (theoretical: 612.23 g/mol, measured: 612 g/mol)

[Synthesis Example 25] Synthesis of compound Inv-55

Compound IC-3 (5 g, 13.07 mmol) synthesized in Preparation Example 3 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 3, and 2-chloro-4,6-diphenyl-1 Synthesis Example 3, except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (7.00 g, 26.15 mmol) instead of ,3,5-triazine (6.70 g, 26.15 mmol) The same procedure was followed to obtain the compound Inv-55 (4.17 g, yield 52%).

GC-Mass (theoretical: 613.23 g/mol, measured: 613 g/mol)

[Synthesis Example 26] Synthesis of compound Inv-60

Compound IC-3 (5 g, 13.07 mmol) synthesized in Preparation Example 3 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-chloro-5-phenylpyrimidine (2.74 g, 14.38 mmol), except for using the compound Inv-60 (4.21 g, yield 60%) in the same manner as in Synthesis Example 1 above. got

GC-Mass (theoretical: 536.20 g/mol, measured: 536 g/mol)

[Synthesis Example 27] Synthesis of compound Inv-70

Compound IC-3 (4 g, 10.46 mmol) synthesized in Preparation Example 3 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.96 g, 11.50 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain the compound Inv-70 (5.27 g, yield 73%).

GC-Mass (theoretical: 689.26 g/mol, measured: 689 g/mol)

[Synthesis Example 28] Synthesis of compound Inv-78

Compound IC-4 (5 g, 15.46 mmol) synthesized in Preparation Example 4 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-chloro-4,6-diphenylpyrimidine (4.54 g, 17.01 mmol), the same procedure as in Synthesis Example 1 was performed, except that compound Inv-78 (5.56 g, yield 65) %) was obtained.

GC-Mass (theoretical: 553.16 g/mol, measured: 553 g/mol)

[Synthesis Example 29] Synthesis of compound Inv-80

The compound IC-4 (5 g, 15.46 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 3, and 2-chloro-4,6-diphenyl-1 Synthesis Example 3, except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (8.28 g, 30.92 mmol) instead of ,3,5-triazine (6.70 g, 26.15 mmol) The same procedure was performed to obtain compound Inv-80 (4.46 g, yield 52%).

GC-Mass (theoretical: 554.16 g/mol, measured: 554 g/mol)

[Synthesis Example 30] Synthesis of compound Inv-83

Compound IC-4 (5 g, 15.46 mmol) synthesized in Preparation Example 4 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-(4-chlorophenyl)pyrimidine (3.24 g, 17.01 mmol), except for using the compound Inv-83 (4.36 g, yield 59%) in the same manner as in Synthesis Example 1 above. ) was obtained.

GC-Mass (theoretical: 477.13 g/mol, measured: 477 g/mol)

[Synthesis Example 31] Synthesis of compound Inv-95

Compound IC-4 (4 g, 12.37 mmol) synthesized in Preparation Example 4 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.68 g, 13.61 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain the compound Inv-95 (5.62 g, yield 72%).

GC-Mass (theoretical: 630.19 g/mol, measured: 630 g/mol)

[Synthesis Example 32] Synthesis of compound Inv-104

Compound IC-5 (5 g, 15.00 mmol) synthesized in Preparation Example 5 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 4-chloro-2,6-diphenylpyrimidine (4.40 g, 16.50 mmol), except for using the compound Inv-104 (4.99 g, yield 59) in the same manner as in Synthesis Example 1 above. %) was obtained.

GC-Mass (theoretical: 563.24 g/mol, measured: 563 g/mol)

[Synthesis Example 33] Synthesis of compound Inv-120

Compound IC-5 (4 g, 12.00 mmol) synthesized in Preparation Example 5 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.54 g, 13.20 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain the compound Inv-120 (4.38 g, yield 57%).

GC-Mass (theoretical: 640.26 g/mol, measured: 640 g/mol)

[Synthesis Example 34] Synthesis of compound Inv-125

Compound IC-5 (4 g, 12.00 mmol) synthesized in Preparation Example 5 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.54 g, 13.20 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain compound Inv-125 (5 g, yield 65%).

GC-Mass (theoretical: 640.26 g/mol, measured: 640 g/mol)

[Synthesis Example 35] Synthesis of compound Inv-130

The compound IC-5 (5 g, 16.27 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 3, and 2-chloro-4,6-diphenyl-1 Synthesis Example 3, except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (8.71 g, 32.54 mmol) instead of ,3,5-triazine (6.70 g, 26.15 mmol) The same procedure was followed to obtain compound Inv-130 (4.29 g, yield 49%).

GC-Mass (theoretical: 538.18 g/mol, measured: 538 g/mol)

[Synthesis Example 36] Synthesis of compound Inv-137

Compound IC-6 (5 g, 16.27 mmol) synthesized in Preparation Example 6 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol), except that 5-chloro-2,2'-bipyridine (3.41 g, 17.90 mmol) was used instead of the compound Inv-137 (5.18 g, yield) by the same procedure as in Synthesis Example 1 69%) was obtained.

GC-Mass (theoretical: 461.15 g/mol, measured: 461 g/mol)

[Synthesis Example 37] Synthesis of compound Inv-145

Compound IC-6 (4 g, 13.01 mmol) synthesized in Preparation Example 6 was used instead of compound IC-1 (5 g, 13.07 mmol) used in Synthesis Example 1, and 2-chloro-4,6-diphenylpyrimidine (3.84) g, 14.38 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.92 g, 14.32 mmol), except for using the same procedure as in Synthesis Example 1 was carried out to obtain compound Inv-145 (5.28 g, yield 66%).

GC-Mass (theoretical: 614.21 g/mol, measured: 614 g/mol)

[Example 1] Manufacturing of blue organic EL device

After high-purity sublimation purification of the compound Inv-3 synthesized in Synthesis Example 1 by a commonly known method, a blue organic EL device was manufactured according to the following procedure.

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 (80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (Doosan Electronics, 30 nm)/Compound Inv-3 (5 nm)/Alq ₃ ( 25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

The structures of NPB, ADN and Alq ₃ used at this time are as follows.

[Example 2] to [Example 37] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used as the electron transport auxiliary layer material instead of the compound Inv-3 used in Example 1.

[Comparative Example 1] Preparation of blue organic electroluminescent device

_{Except for depositing Alq 3} , which is an electron transport layer material, at 30 nm instead of 25 nm, without using the compound Inv-3 used as the electron transport auxiliary layer material in Example 1, and in the same manner as in Example 1, blue An organic EL device was fabricated.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Example 1, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. indicated.

Sample electron transport layer Driving voltage (V) Emission peak (nm) Current efficiency cd/A) Example 1 Inv-3 4.2 457 6.3 Example 2 Inv-4 4.2 458 6.2 Example 3 Inv-5 4.1 458 6.5 Example 4 Inv-8 4.3 457 6.3 Example 5 Inv-18 4.3 456 6.0 Example 6 Inv-19 4.3 458 5.9 Example 7 Inv-20 4.2 455 6.1 Example 8 Inv-23 4.4 458 5.7 Example 9 Inv-24 4.3 459 5.8 Example 10 Inv-25 4.3 458 6.0 Example 11 Inv-28 4.3 457 6.2 Example 12 Inv-29 4.3 458 6.2 Example 13 Inv-30 4.2 458 6.3 Example 14 Inv-33 4.4 458 6.2 Example 15 Inv-35 4.3 456 6.3 Example 16 Inv-38 4.5 457 6.1 Example 17 Inv-43 4.4 458 5.7 Example 18 Inv-44 4.4 458 5.8 Example 19 Inv-45 4.3 457 6.0 Example 20 Inv-48 4.5 457 5.7 Example 21 Inv-49 4.5 458 5.7 Example 22 Inv-50 4.4 457 5.8 Example 23 Inv-53 4.2 456 6.3 Example 24 Inv-54 4.2 458 6.2 Example 25 Inv-55 4.1 458 6.5 Example 26 Inv-60 4.3 457 6.2 Example 27 Inv-70 4.2 458 6.1 Example 28 Inv-78 4.3 457 6.2 Example 29 Inv-80 4.2 458 6.3 Example 30 Inv-83 4.4 456 6.2 Example 31 Inv-95 4.3 457 6.0 Example 32 Inv-104 4.5 458 5.8 Example 33 Inv-120 4.5 459 5.7 Example 34 Inv-125 4.6 458 5.7 Example 35 Inv-130 4.4 457 5.9 Example 36 Inv-137 4.6 459 5.7 Example 37 Inv-145 4.6 457 5.8 Comparative Example 1 - 4.7 458 5.6

As shown in Table 1, the blue organic EL devices of Examples 1 to 37 including an electron transport auxiliary layer formed of the compound according to the present invention are of Comparative Example 1 including an electron transport layer made of Alq ₃ without an electron transport auxiliary layer. It was found that the blue organic EL device exhibited superior performance in terms of current efficiency and driving voltage.

[Example 38] Manufacturing of blue organic EL device

In the same manner as in Example 1, except that the compound Inv-5 used in Example 1 was used as an electron transport auxiliary layer material instead of the compound Inv-3 used in Example 1, and _{Bphen was used instead of Alq 3} as the electron transport layer material. An organic EL device was manufactured.

The structure of Bphen used in this case is as follows.

[Example 39] to [Example 44] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 38, except that the compounds shown in Table 2 below were used as the electron transport auxiliary layer material instead of the compound Inv-5 used in Example 38.

[Comparative Example 2] Preparation of blue organic electroluminescent device

A blue organic EL device was carried out in the same manner as in Example 38, except that the compound Inv-5 used as the electron transport layer material in Example 38 was not used and Bphen, the electron transport layer material, was deposited at 30 nm instead of 25 nm. was produced.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 38 to 44 and Comparative Example 2, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. indicated.

Sample electron transport layer Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 38 Inv-5 4.2 458 6.7 Example 39 Inv-19 4.3 458 6.1 Example 40 Inv-25 4.2 458 6.2 Example 41 Inv-45 4.3 457 6.2 Example 42 Inv-78 4.2 457 6.4 Example 43 Inv-83 4.4 458 6.3 Example 44 Inv-137 4.5 459 5.9 Comparative Example 2 - 4.6 458 5.8

As shown in Table 2, the blue organic EL devices of Examples 38 to 44 including the electron transport auxiliary layer formed of the compound according to the present invention were the blue color of Comparative Example 2 including the electron transport layer formed of Bphen without the electron transport auxiliary layer. It was found that the organic EL device exhibited superior performance in terms of current efficiency and driving voltage.

[Example 45] Manufacturing of blue organic EL device

In the same manner as in Example 1, except that the compound Inv-5 used in Example 1 was used as an electron transport auxiliary layer material instead of the compound Inv-3 used in Example 1, and _{TPBI was used instead of Alq 3} as the electron transport layer material. An organic EL device was manufactured. The structure of the TPBI used at this time is as follows.

[Example 46] to [Example 54] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 45, except that the compounds shown in Table 3 below were used as the electron transport auxiliary layer material instead of the compound Inv-5 used in Example 45.

[Comparative Example 3] Preparation of blue organic electroluminescent device

Except for depositing the electron transport layer material, TPBI, at 30 nm instead of 25 nm, without using the compound Inv-5 used as the electron transport auxiliary layer material in Example 45, and in the same manner as in Example 45, blue organic An EL device was fabricated.

[Evaluation Example 3]

For the organic electroluminescent devices prepared in Examples 45 to 54 and Comparative Example 3, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below. indicated.

Sample electron transport layer Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 45 Inv-5 3.9 458 6.9 Example 46 Inv-19 4.0 458 6.4 Example 47 Inv-25 4.0 458 6.5 Example 48 Inv-38 4.2 457 6.4 Example 49 Inv-45 4.0 457 6.5 Example 50 Inv-55 3.9 458 6.8 Example 51 Inv-83 4.1 458 6.6 Example 52 Inv-104 4.3 459 6.2 Example 53 Inv-130 4.2 458 6.3 Example 54 Inv-145 4.3 457 6.2 Comparative Example 3 - 4.4 458 6.1

As shown in Table 3, the blue organic EL devices of Examples 45 to 54 including the electron transport auxiliary layer made of the compound according to the present invention are the blue color of Comparative Example 3 including the TPBI electron transport layer without the electron transport auxiliary layer. It was found that the organic EL device exhibited excellent performance in terms of current efficiency and driving voltage.

[Example 55] Manufacturing of blue organic EL device

_{Except for depositing compound Inv-20 instead of Alq 3 as an} electron transport layer material instead of using the compound Inv-3 used as the electron transport auxiliary layer material in Example 1, it was carried out in the same manner as in Example 1, An EL device was fabricated.

[Example 56] to [Example 61] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 4 below were used as electron transport layer materials instead of the compound Inv-20 used in Example 55.

[Evaluation Example 4]

For the organic electroluminescent devices prepared in Examples 55 to 61, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 4 below.

Sample electron transport layer Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 55 Inv-20 4.1 457 6.3 Example 56 Inv-25 4.2 458 6.2 Example 57 Inv-30 4.1 458 6.3 Example 58 Inv-45 4.2 457 6.2 Example 59 Inv-125 4.3 457 6.2 Example 60 Inv-130 4.1 458 6.3 Example 61 Inv-145 4.2 458 6.2 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 Bphen 4.6 458 5.8 Comparative Example 3 TPBI 4.4 458 6.1

As shown in Table 4, the blue organic EL devices of Examples 55 to 61 including the electron transport layer made of the compound according to the present invention were superior in current efficiency and driving voltage to the blue organic EL devices of Comparative Examples 1 to 3 performance was found to be

100: positive electrode, 200: negative electrode
300: one or more organic material layers, 301: light emitting layer,
302: a first organic material layer, 303: an electron transport layer,
304: hole injection layer, 305: hole transport layer;
306: electron injection layer

Claims (6)

anode; cathode; and one or more organic material layers interposed between the positive electrode and the negative electrode,
The at least one organic material layer may include a light emitting layer; an electron transport auxiliary layer positioned between the light emitting layer and the cathode and containing a compound represented by the following formula (1); an electron transport layer positioned between the electron transport auxiliary layer and the cathode; and an electron injection layer positioned between the electron transport layer and the cathode;
[Formula 1]

(In Formula 1,
Cy1 and Cy2 are the same as or different from each other, and are each independently _{selected from the group consisting of a C 6} ~ C ₄₀ aromatic ring and a heteroaromatic ring having 5 to 40 nuclear atoms;
R _{1 To} R ₄ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ aryl boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent group to form a condensed ring can;
X ₁ and X ₂ are the same as or different from each other, and each independently from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ) selected, provided that at least one of _{X 1} and X _{2 is N(Ar 1} ), wherein when Ar ₁ is plural, they are the same or different from each other;
Ar _{1 To} Ar _{5 Are} the same as or different from each other, and each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group , Heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ Cycloalkyl group , Heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphos a pin group, a C ₆ ~ C ₄₀ arylphosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group selected from the group consisting of;
However, at least one Ar ₁ is a substituent represented by the following formula (3),
[Formula 3]

In Formula 3,
L 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;
Z ₁ to Z ₅ are the same or different from each other, and each independently is N or C(R ₁₁ ), provided _{that at least one of Z 1} to Z ₅ is N, and in this _{case, when R 11} is plural, they are the same or different from each other and;
R ₁₁ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ Aryloxy group C ₁ to C ₄₀ Alkyloxy group, C ₃ to C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Aryl phosphine oxide group and C ₆ ~ C _{40 It} may be selected from the group consisting of an arylsilyl group, or combined with an adjacent group to form a condensed ring,
In this case, the C ₆ ~ C ₄₀ aromatic ring of Cy1 and Cy2, the heteroaromatic ring having 5 to 40 nuclear atoms, R ₁ to R ₄ and Ar _{1 To} Ar ₅ C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group, L of the arylene group , a heteroaryl group, and the alkyl group of said R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boronic group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ substituted to the aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ 1 substituent at least one selected from an aryl silyl group consisting of C ₄₀ of or unsubstituted, wherein when the substituents are plural, they may be the same or different from each other) delete delete According to claim 1,
The compound represented by Formula 1 is an organic electroluminescent device characterized in that it is represented by Formula 2:
[Formula 2]

(In Formula 2,
X ₁ , X ₂ and R ₁ to R ₄ are each as defined in claim 1 ;
a and b are each independently an integer of 0 to 4, and when a and b are each an integer of 1 to 4, R ₅ and R ₆ are the same as or different from each other, and each independently deuterium (D), halogen, cyano No, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₄₀ group, and C ₆ ~ C ₄₀ may be selected from the group consisting of an arylsilyl group, or combined with an adjacent group to form a condensed ring). delete According to claim 1,
The substituent represented by Formula 3 is an organic electroluminescent device, characterized in that it is selected from the group consisting of substituents represented by the following A-1 to A-15:

(In A-1 to A-15 above,
L and L2 are a single bond, or _{are selected from the group consisting of a C 6} ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
When R ₁₁ is plural, they are the same as or different from each other,
R ₁₁ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ Aryloxy group C ₁ to C ₄₀ Alkyloxy group, C ₃ to C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Aryl phosphine oxide group and C ₆ ~ C _{40 It} may be selected from the group consisting of an arylsilyl group, or combined with an adjacent group to form a condensed ring,
n is an integer of 0 to 4, and when n is 1 to 4, R ₁₂ is deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C _{40 60} Aryloxy group C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ an aryl boronic of C _40, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups combine to the can form a condensed ring,
In this case, the arylene group and heteroarylene group of L and L2, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkylox group of _{R 11} and R ₁₂ Group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently 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 ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl It is unsubstituted or substituted with one or more substituents selected from the group consisting of, and when the substituents are plural, they may be the same or different from each other).

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