KR20160001537A - Pyrazole-based compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a pyrazole-based compound and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a pyrazole-based compound and an organic light emitting device using the pyrazole-based compound.

The present invention relates to a novel pyrazole-based compound and an organic light-emitting device comprising the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

The present invention provides a novel pyrazole-based compound and an organic light-emitting device comprising the same.

The present application provides compounds of formula (1).

[Chemical Formula 1]

In Formula 1,

L1 to L3 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic arylene; Or a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroarylene,

t is an integer from 0 to 5,

R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C ₁ to C ₆₀ straight or branched alkyl; Substituted or unsubstituted C ₂ to C ₆₀ straight or branched chain alkenyl; Substituted or unsubstituted C ₂ to C ₆₀ straight or branched chain alkynyl; A substituted or unsubstituted C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; Substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; Substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl; -SiRR'R "; -P (= O) RR '; and -NRR'

Wherein R, R and R "are the same or different from each other and each independently represents hydrogen; C ₁ to C ₆₀ linear or branched alkyl; substituted or unsubstituted C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; A C ₆ to C ₆₀ monocyclic or polycyclic aryl, and a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl,

m and n are each independently an integer of 0 to 4,

p and q are each independently an integer of 0 to 2,

When m, n, p, q, and t are each an integer of 2 or more, the substituents in each parenthesis are the same or different from each other.

In addition, the present application provides an organic light emitting device including a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of Formula 1 .

The compound described in this specification can be used as an organic layer material of an organic light emitting device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting device.

In particular, the compound of Formula 1 may be used as a material of an electron transport layer of an organic light emitting device.

The compound of Formula 1 may be used as a hole blocking layer of an organic light emitting device.

The compound of Formula 1 may be used as a material of the light emitting layer of the organic light emitting device.

FIGS. 1 to 3 illustrate the stacking order of electrodes and organic layers of the organic light emitting diode according to the embodiments of the present application.

Hereinafter, the present application will be described in detail.

The compounds described in this specification can be represented by the above formula (1). Specifically, the compound of Formula 1 may be used as an organic material layer material of an organic light emitting diode according to the structural features of the core structure and the substituent.

In particular, the compound of Chemical Formula 1 is a dimer structure of pyrazoloquinazoline having a strong electron attracting property. When the compound is used as a material of an electron transport layer, it is easy to transfer electrons to a light emitting layer and has a linear structure And thus it is possible to facilitate the intermolecular packing and to exhibit the effect of excellent electron mobility.

In addition, the compound of Formula 1 can be designed to include various aryls or heteroaryls as a linking group located between two pyrazole quinazolines, and it is easy to synthesize and purify.

In the present specification, the term "substituted or unsubstituted" means halogen; C ₁ to C ₆₀ linear or branched alkyl; C ₂ to C ₆₀ straight or branched chain alkenyl; C ₂ to C ₆₀ linear or branched alkynyl; C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic aryl; C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl; -SiRR'R ", -P (= O) RR ', and -NRR', or a substituted or unsubstituted aryl group, wherein at least two of the substituents exemplified above are substituted, For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group, that is, the biphenyl group may be an aryl group, and two phenyl groups may be connected to each other. R "are the same or different and are each independently selected from the group consisting of C ₁ to C ₆₀ linear or branched alkyl; C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

In the present specification, the halogen includes F, Cl, Br and I.

In the present specification, alkyl includes straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.

In the present specification, alkenyl includes straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, alkynyl includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, the cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which cycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be other ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like. The carbon number of the cycloalkyl may be 3 to 60, specifically 3 to 40, more particularly 5 to 20.

In the present specification, heterocycloalkyl includes O, S, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which heterocycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be heterocycloalkyl, but may be other ring groups such as cycloalkyl, aryl, heteroaryl, and the like. The heterocycloalkyl may have from 2 to 60 carbon atoms, specifically from 2 to 40, more specifically from 3 to 20 carbon atoms.

In the present specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, the polycyclic ring means a group in which aryl is directly connected to another ring group or condensed. Here, the other ring group may be aryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl and the like. Aryl includes a spiro group. The carbon number of the aryl may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of aryl include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, klycenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, But are not limited to, fluorenyl, indenyl, acenaphthylenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, spirocyclopentafluorenyl, and condensed rings thereof.

In the present specification, the spiro group is a group including a spiro structure and may have from 15 to 60 carbon atoms. For example, a spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorene group. Specifically, the spiro group includes groups of the following structural formulas.

As used herein, heteroaryl includes S, O, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms and may be further substituted by other substituents. Herein, the term "polycyclic" means a heteroaryl group directly bonded to another ring group or condensed therewith. Here, the other ring group may be heteroaryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like. The heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40, more specifically 3 to 25 carbon atoms. Specific examples of heteroaryl include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, Thiadiazolyl, thiazolyl, thiazolyl, pyrazinyl, thiopyranyl, diazinyl, oxazinyl, oxadiazolyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, Thiazolidinyl, quinolyl, isoquinolyl, quinazolinyl, quinazolinyl, isoquinazolinyl, naphthyridyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazanaphthalenyl, triazinene, Benzothiophenyl, benzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiophenyl, benzofuranyl, Phenazinyl, dibenzosiloryl, dibenzoselenophenyl, dibenzosilinyl, There may be mentioned condensed rings such as thienyl, thienyl, thioxanthienyl, selenoxanthienyl, dihydrophenazinyl, phenoxazinyl, phenanthridyl, pyrazolaphthalazinyl, pyrazoloquinazolyl and pyridoindazolyl. But is not limited thereto.

In the present specification, m, n, p, q and t mean the numbers of R1, R2, R3, R4 and L2, respectively.

According to one embodiment of the present application, when m is an integer of 2 or more, R1 may be the same as or different from each other.

According to an embodiment of the present application, when n is an integer of 2 or more, R2 may be the same or different from each other.

According to one embodiment of the present application, when p is an integer of 2 or more, R3 may be the same as or different from each other.

According to one embodiment of the present application, when q is an integer of 2 or more, R4 may be the same as or different from each other.

According to one embodiment of the present application, when t is an integer of 2 or more, L2 may be the same or different from each other.

According to one embodiment of the present application, L1 to L3 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ monocyclic or polycyclic arylene; Or a substituted or unsubstituted C ₂ to C ₂₀ monocyclic or polycyclic heteroarylene.

According to one embodiment of the present application, L1 and L3 are the same or different from each other and each independently represent a group consisting of phenylene, biphenylene, naphthylene, anthracenylene, pyridylene, pyrimidylene, and triazienylene ≪ / RTI >

Which may be further substituted or unsubstituted with C ₁ -C ₂₀ alkyl, C ₆ -C ₂₀ aryl, or C ₂ -C ₂₀ heteroaryl.

That is, L1 and L3 are the same or different and each independently represents a substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracenylene, Substituted or unsubstituted pyridylenes, substituted or unsubstituted pyridylenes, substituted or unsubstituted pyrimidylenes, and substituted or unsubstituted triazinylenes,

Means that the "substituted or unsubstituted" may be further substituted or unsubstituted with at least one selected from C ₁ -C ₂₀ alkyl, C ₆ -C ₂₀ aryl, and C ₂ -C ₂₀ heteroaryl .

According to one embodiment of the present application, L2 is selected from the group consisting of phenylene, biphenylene, naphthylene, anthracenylene, phenanthrenylene, chrysinylene, pyrenylene, triphenylrenylene, pyridylene, Wherein the aromatic ring is selected from the group consisting of a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, Thioxanthrenylene, dibenzosiliconylene, and selenoxanthienylene, and the sum of

Which may be further substituted or unsubstituted with C ₁ -C ₂₀ alkyl, C ₆ -C ₂₀ aryl, or C ₂ -C ₂₀ heteroaryl.

That is, the L2 may be substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, naphthylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted crecenyl Substituted or unsubstituted pyridylenes, substituted or unsubstituted pyridylenes, substituted or unsubstituted pyridylenes, substituted or unsubstituted pyridylenes, substituted or unsubstituted pyrazinylenes, substituted or unsubstituted pyrazinylenes, substituted or unsubstituted pyridylenes, Substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted spirocyclopentafluorenylenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, Unsubstituted dibenzoselenophenylene, substituted or unsubstituted dibenzosilolylene, substituted or unsubstituted acrylidynylene, substituted or unsubstituted xanthenylene, substituted or unsubstituted thioxanthrenylene, substituted Or unsubstituted dibenzosilinylene, and substituted or unsubstituted stenylene selenate,

Means that the "substituted or unsubstituted" may be further substituted or unsubstituted with at least one selected from C ₁ -C ₂₀ alkyl, C ₆ -C ₂₀ aryl, and C ₂ -C ₂₀ heteroaryl .

According to one embodiment of the present application, L2 is selected from the group consisting of methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, Dibenzothiophenyl, dibenzosilylolyl, dibenzoselenophenyl, acridinyl, xanthenyl, thioxanthinyl, dibenzosilinyl, dibenzothiophenyl, dibenzothiophenyl, Or selenoxanthienyl. ≪ / RTI > In addition, the fluorenyl may include the spiro group described above.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₂₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₂₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, the formula (1) may be represented by any one of the following formulas (2) to (4).

According to one embodiment of the present application, t is an integer from 1 to 3.

According to one embodiment of the present application, t is one.

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

R 1, R 2, R 3, R 4, m and n are the same as defined in formula (1)

R5 and R6 are the same as defined in R1 of formula (1).

According to one embodiment of the present application, in the general formulas (2) to (4), R1 to R6 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, in the general formulas (2) to (4), R1 to R6 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₂₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₂₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, in the general formulas 2 to 4, at least one of R 1 to R 6 is a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, in the general formulas 2 to 4, at least two of R 1 to R 6 are substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, in the general formulas (2) to (4), R1 to R6 are the same or different and each independently hydrogen; heavy hydrogen; And substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl.

According to one embodiment of the present application, in the general formulas (2) to (4), R1, R2, R5 and R6 are the same or different and each independently hydrogen; heavy hydrogen; And substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl.

According to one embodiment of the present application, in the general formulas (2) to (4), R1, R2, R5 and R6 are the same or different and each independently hydrogen; It can be deuterium.

According to one embodiment of the present application, in the general formulas (2) to (4), R 3 and R 4 may be the same or different and each independently a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl .

According to one embodiment of the present application, in the general formulas (2) to (4), R 3 and R 4 may be the same or different and each independently a substituted or unsubstituted C ₆ to C ₂₀ monocyclic or polycyclic aryl .

According to one embodiment of the present application, in the general formulas 2 to 4, R 3 and R 4 may be phenyl, biphenyl, naphthyl, anthracenyl, or phenanthrenyl.

According to one embodiment of the present application, the formula (1) may be selected from the following formulas.

The above-mentioned compounds can be produced on the basis of the preparation examples described later. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

Another embodiment of the present application provides an organic light emitting device comprising the compound of formula (1). Specifically, the organic light emitting device according to the present application includes a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, and at least one of the organic layers includes the compound of Formula 1.

FIGS. 1 to 3 illustrate the stacking process of the electrodes and organic layers of the organic light emitting diode according to the embodiments of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present application.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG.

FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305 and an electron injection layer 306. However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of the above formula (1).

The compound of formula (I) may constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The compound of Formula 1 may be used as a hole injecting material, a hole transporting material, a light emitting material, a hole blocking material, an electron transporting material, and an electron injecting material in an organic light emitting device.

For example, the compound according to one embodiment of the present application can be used as an electron injecting layer, an electron transporting layer, or a material of a layer which simultaneously injects electrons and transports the organic light emitting element.

Further, the compound according to one embodiment of the present application can be used as a light emitting layer material of an organic light emitting device. Specifically, the compound can be used singly as a light emitting material, or as a host material or a dopant material in a light emitting layer.

In addition, the compound according to one embodiment of the present application can be used as a phosphorescent host material of an organic light emitting device. In this case, the compound according to one embodiment of the present application is included with the phosphorescent dopant.

In addition, the compound according to one embodiment of the present application can be used as a material for the hole blocking layer of the organic light emitting device.

In the organic light emitting device according to the present application, materials other than the compound of Formula 1 are exemplified below, but they are for illustrative purposes only and are not intended to limit the scope of the present application and include materials known in the art Can be replaced.

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used.

As the cathode material, materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can be used.

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) PANDOT / PSS (Polyaniline / Dodecylbenzenesulfonic acid), which is a soluble conductive polymer such as TCA, m-MTDATA, m-MTDAPB, 4-ethylenedioxythiophene / poly (4-styrenesulfonate) / poly (4-styrene sulfonate) / Pani / CSA (polyaniline / camphor sulfonic acid) PANI / PSS (polyaniline / poly (4-styrene-sulfonate): polyaniline / poly (4-styrenesulfonate)).

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.

As the electron injecting material, for example, LiF is typically used in the art, but the present application is not limited thereto.

As the light emitting material, red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used. Further, a fluorescent material may be used as the light emitting material, but a phosphorescent material may also be used. As the light emitting material, a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used.

When the compound according to the present application is used as a phosphorescent host material, phosphorescent dopant materials used together can be those known in the art.

For example, phosphorescent dopant materials represented by LL'MX, LL'L "M, LMXX ', L ₂ MX and L ₃ M can be used, but the scope of the present application is not limited by these examples.

Here, L, L ', L ", X and X' are two different left ligands and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, and the like.

L is sp ² An anionic bidentate ligand that is coordinated to M by carbon and hetero atoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (7,8-benzoquinoline) Phenyl) pyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and the like. Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

Hereinafter, the present application will be described in more detail by way of examples, but these are for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[Preparation Example 1] Preparation of a compound having a substituent shown in the following Table 1

Preparation of Compound 1-1

Methyl 2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF (tetrahydrofuran), followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, acetophenone (1 eq.) Was slowly added dropwise, followed by stirring at room temperature for 2 hours and heating at 100 ° C for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1N HCl, aqueous NaHCO ₃ solution, and H ₂ O. The extract was separated and purified by column chromatography to obtain Compound 1-1.

Preparation of Compound 1-2

Compound 1-1 (1 eq.) Was dissolved in 160 mL of DMF, followed by addition of H ₂ NNH ₂ .H ₂ O (1.1 eq.) And the mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain a compound 1-2.

Preparation of compounds 1-3

Compound 1-2 (1 eq.) Was dissolved in DMF (240 mL), CuI (0.1 eq.) And 4-bromobenzaldehyde (1.2 eq.) Were added and stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 1-3.

Preparation of compounds 1-4

Compound 1-3 (1 eq.) Was dissolved in 60 mL of DMF, CuI (0.1 eq.) Was added, and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain the compound 1-4.

Preparation of compounds 1-5

Compound 1-4 (1 eq.) Was dissolved in 300 mL of DMF, and then 2,2,3,3,7,7,8,8-octamethyl-1,4,6,9-tetraoxa-514- [4.4] nonane (2,2,3,3,7,7,8,8-octamethyl-1,4,6,9-tetraoxa-5l4-boraspiro [4.4] nonane) (2 eq.), PdCl ₂ (dppf) (0.05 eq.) and KOAc (3 eq.) were added, and the mixture was stirred at 80 ° C for 24 hours. After the reaction was completed, dichloromethane and H ₂ O were extracted. The extract was separated and purified by column chromatography to obtain a compound 1-5.

compound P1 Manufacturing

The compound 1-5 (2.2 eq.) Was dissolved in toluene / ethanol / H ₂ O = 5: 1: 1 and then Pd (PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq. Compound S-1 (1 eq.) Was added and heated for 4 hours. After the reaction was completed, dichloromethane and H ₂ O were extracted. The extract was separated and purified by column chromatography to obtain the desired compound P1.

In Preparation Example 1, Ar of S-1 was applied as shown in Table 1 below to prepare Compounds 1 to 20.

compound No . Ar compound No . Ar One

11

2

12

3

13

4

14

5

15

6

16

7

17

8

18

9

19

10

20

[Preparation Example 2] Preparation of a compound having a substituent shown in the following Table 2

Preparation of Compound 2-3

Compound 1-2 (1 eq.) Was dissolved in 240 mL of DMF, CuI (0.1 eq.) And 3-bromobenzaldehyde (1.2 eq.) Were added and stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 2-3.

Preparation of compound 2-4

Compound 2-4 was obtained in the same manner as in the production of 1-4 in Preparative Example 1 except that Compound 2-3 was used instead of Compound 1-3.

Preparation of Compound 2-5

Compound 2-5 was obtained in the same manner as in the production of 1-5 in Production Example 1 except that Compound 2-4 was used instead of Compound 1-4.

compound P2 Manufacturing

The target compound P2 was obtained in the same manner as in the production of P1 in Production Example 1, except that the compound 2-5 was used instead of the compound 1-5.

In Preparation Example 2, Ar of S-1 was applied as shown in Table 2 below to prepare compounds 26 and 45.

compound No . Ar compound No . Ar 26

36

27

37

28

38

29

39

30

40

31

41

32

42

33

43

34

44

35

45

[Preparation Example 3] Preparation of a compound having a substituent shown in the following Table 3

Preparation of compound 3-3

Compound 1-2 (1 eq.) Was dissolved in 240 mL of DMF and CuI (0.1 eq.) And 6-bromo-2-naphthaldehyde (1.2 eq.) And the mixture was stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain the compound 3-3.

Preparation of compound 3-4

Compound 3-4 was obtained in the same manner as in the production of 1-4 in Production Example 1 except that Compound 3-3 was used instead of Compound 1-3.

Preparation of Compound 3-5

Compound 3-5 was obtained in the same manner as in the production of 1-5 in Production Example 1 except that Compound 3-4 was used instead of Compound 1-4.

compound P3 Manufacturing

The procedure of Production Example 1 was repeated except that Compound 3-5 was used instead of Compound 1-5 to obtain the target compound P3.

In Preparation Example 3, Ar of S-1 was applied as shown in Table 3 below to prepare Compounds 21 to 23.

compound No . Ar compound No . Ar 21

23

22

[Preparation Example 4] Preparation of a compound having a substituent shown in the following Table 4

Preparation of compound 4-3

Compound 1-2 (1 eq.) Was dissolved in 240 mL of DMF. CuI (0.1 eq.) And 5-bromopicolinaldehyde (1.2 eq.) Were added thereto and stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 1-3.

Preparation of compound 4-4

Compound 4-4 was obtained in the same manner as in the production of 1-4 in Production Example 1, except that Compound 4-3 was used instead of Compound 1-3.

Preparation of Compound 4-5

Compound 4-5 was obtained in the same manner as in the production of 1-5 in Production Example 1 except that Compound 4-4 was used in place of Compound 1-4.

compound P4 Manufacturing

The procedure of Production Example 1 was repeated except that Compound 4-5 was used instead of Compound 1-5 to obtain the desired compound P4.

In Preparation Example 4, Ar of S-1 was applied as shown in Table 4 to prepare Compounds 24 and 25.

compound No . Ar compound No . Ar 24

25

[Preparation Example 5] Preparation of a compound having a substituent shown in the following Table 5

Preparation of Compound 5-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 4-bromoacetophenone (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1N HCl, aqueous NaHCO ₃ solution, and H ₂ O. The extract was separated and purified by column chromatography to obtain Compound 5-1.

Preparation of Compound 5-2

Compound 5-1 (1 eq.) Was dissolved in 160 mL of DMF, followed by addition of H ₂ NNH ₂ .H ₂ O (1.1 eq.) And the mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 5-2.

Preparation of Compound 5-3

Compound 5-2 (1 eq.) Was dissolved in DMF (240 mL), CuI (0.1 eq.) And benzaldehyde (1.2 eq.) Were added and stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain a compound 5-3.

Preparation of compound 5-4

Compound 5-3 (1 eq.) Was dissolved in 60 mL of DMF, CuI (0.1 eq.) Was added, and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain a compound 5-4.

Preparation of Compound 5-5

Compound 5-4 (1 eq.) Was dissolved in 300 mL of DMF, and then 2,2,3,3,7,7,8,8-octamethyl-1,4,6,9-tetraoxa-514- [4.4] nonane (2,2,3,3,7,7,8,8-octamethyl-1,4,6,9-tetraoxa-5l4-boraspiro [4.4] nonane) (2 eq.), PdCl2 dppf) (0.05 eq.) and KOAc (3 eq.) were added, and the mixture was stirred at 80 占 폚 for 24 hours. After the reaction was completed, dichloromethane and H ₂ O were extracted. The extract was separated and purified by column chromatography to obtain Compound 5-5.

compound P5 Manufacturing

Compound 5-5 (. 2.2 eq) in toluene / ethanol _{/ H 2 O = 5: 1} : was dissolved in the proportion of _{1, Pd (PPh 3) 4} (. 0.05 eq), K2CO3 (. 3eq), the compound S- 1 (1 eq.) And heated for 4 hours. After the reaction was completed, dichloromethane and H ₂ O were extracted. The extract was separated and purified by column chromatography to obtain the desired compound P5.

In Preparation Example 5, compounds of 51 and 70 were prepared by applying Ar of S-1 as shown in Table 5 below.

compound No . Ar compound No . Ar 51

61

52

62

53

63

54

64

55

65

56

66

57

67

58

68

59

69

60

70

[Preparation Example 6] Preparation of a compound having a substituent shown in the following Table 6

Preparation of Compound 6-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 3-bromoacetophenone (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1 N HCl, aqueous NaHCO ₃ solution and H ₂ O. The extract was separated and purified by column chromatography to obtain 6-1.

Preparation of Compound 6-2

Compound 6-2 was obtained in the same manner as in the production of 5-2 in Production Example 5 except that Compound 6-1 was used instead of Compound 5-1.

Preparation of Compound 6-3

Compound 6-2 was prepared in the same manner as in the production of 5-3 in Production Example 5, except that Compound 6-2 was used instead of Compound 5-2.

Preparation of Compound 6-4

Compound 6-3 was prepared in the same manner as in the production of 5-4 in Production Example 5 except that Compound 6-3 was used instead of Compound 5-3.

Preparation of Compound 6-5

Compound 6-5 was obtained in the same manner as in the production of 5-5 in Production Example 5, except that Compound 6-4 was used instead of Compound 5-4.

compound P6 Manufacturing

Compound P6 was obtained in the same manner as in the production of P5 in Production Example 5 except that Compound 6-5 was used instead of Compound 5-5.

In Preparation Example 6, Ar of S-1 was applied as shown in the following Table 6 to prepare Compounds 76 to 95.

compound No . Ar compound No . Ar 76

86

77

87

78

88

79

89

80

90

81 91

82

92

83

93

84

94

85

95

[Preparation Example 7] Preparation of a compound having a substituent shown in the following Table 7

Preparation of Compound 7-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 1- (6-bromonaphthalen-2-yl) ethan-1-one (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1N HCl, aqueous NaHCO ₃ solution, and H ₂ O. The extract was separated and purified by column chromatography to obtain 7-1.

Preparation of Compound 7-2

Compound 7-2 was obtained in the same manner as in the production of 5-2 in Production Example 5, except that Compound 7-1 was used instead of Compound 5-1.

Preparation of Compound 7-3

Compound 7-2 was prepared in the same manner as in the production of 5-3 in Production Example 5, except that Compound 7-2 was used instead of Compound 5-2.

Preparation of Compound 7-4

Compound 7-4 was obtained in the same manner as in the production of 5-4 in Production Example 5, except that Compound 7-3 was used instead of Compound 5-3.

Preparation of Compound 7-5

Compound 7-5 was obtained in the same manner as in the production of 5-5 in Production Example 5, except that Compound 7-4 was used instead of Compound 5-4.

compound P7 Manufacturing

Compound P7 was obtained in the same manner as in the production of P5 in Production Example 5 except that Compound 7-5 was used instead of Compound 5-5.

In Preparation Example 7, Ar of S-1 was applied as shown in Table 7 below to prepare compounds 71 to 73.

compound No . Ar compound No . Ar 71

73

72

[Preparation Example 8] Preparation of a compound having a substituent shown in the following Table 8

Preparation of Compound 8-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 1- (5-bromopyridin-2-yl) ethan-1-one (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1 N HCl, aqueous NaHCO ₃ solution and H ₂ O. The extract was separated and purified by column chromatography to obtain 8-1.

Preparation of Compound 8-2

Compound 8-2 was obtained in the same manner as in the production of 5-2 in Production Example 5 except that Compound 8-1 was used instead of Compound 5-1.

Preparation of Compound 8-3

Compound 8-3 was obtained in the same manner as in the production of 5-3 in Production Example 5, except that Compound 8-2 was used instead of Compound 5-2.

Preparation of Compound 8-4

Compound 8-4 was obtained in the same manner as in the production of 5-4 in Production Example 5, except that Compound 8-3 was used instead of Compound 5-3.

Preparation of Compound 8-5

Compound 8-4 was obtained in the same manner as in the production of 5-5 in Production Example 5, except that Compound 8-4 was used instead of Compound 5-4.

compound P8 Manufacturing

Compound P5 was obtained in the same manner as in the production of P5 in Production Example 5, except that Compound 8-5 was used instead of Compound 5-5.

In Preparation Example 8, Ar of S-1 was applied as shown in Table 8 below to prepare Compounds 74 and 75.

compound No . Ar compound No . Ar 74

75

[Preparation Example 9] Preparation of a compound having a substituent shown in the following Table 9

compound P9 Manufacturing

The compound 1-5 (1.1 eq.) Was dissolved in a toluene / ethanol / H ₂ O ratio of 5: 1: 1 and then Pd (PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq. Compound S-1 (3 eq.) Was added and stirred. Compound 5-5 (1.1 eq.) Was added and heated for 4 hours. After the reaction was completed, the reaction mixture was extracted with dichloromethane and H ₂ O. The extract was separated and purified by column chromatography to obtain a compound P9.

In Preparation Example 9, Ar of S-1 was applied as shown in Table 9 to prepare Compounds 101 to 110.

compound No . Ar compound No . Ar 101

106

102

107

103

108

104

109

105

110

[Preparation Example 10] Preparation of a compound having a substituent shown in the following Table 10

Preparation of compound 10-3

Compound 1-2 (1 eq.) Was dissolved in 240 mL of DMF and CuI (0.1 eq.) And 5-bromo-2-naphthaldehyde (1.2 eq.) And the mixture was stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 10-3.

Preparation of Compound 10-4

Compound 10-4 was obtained in the same manner as in the production of 1-4 in Production Example 1, except that Compound 10-3 was used instead of Compound 1-3.

Preparation of Compound 10-5

Compound 10-5 was obtained in the same manner as in the production of 10-5 in Production Example 1, except that Compound 10-4 was used instead of Compound 1-4.

compound P10 Manufacturing

The procedure of Production Example 1 was repeated except that Compound 10-5 was used instead of Compound 1-5 to obtain the target compound P10.

In Preparation Example 10, Ar of S-1 was applied as shown in Table 10 below to prepare Compounds 46 to 48.

compound No . Ar compound No . Ar 46

48

47

[Preparation Example 11] Preparation of a compound having a substituent shown in the following Table 11

Preparation of Compound 11-3

Compound 1-2 (1 eq.) Was dissolved in 240 mL of DMF. CuI (0.1 eq.) And 4-bromopicolinaldehyde (1.2 eq.) Were added thereto and stirred for 30 minutes. After stirring, 66 mL of NH ₃ .H ₂ O was added and the mixture was stirred at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and H ₂ O. [ The extract was separated and purified by column chromatography to obtain Compound 11-3.

Preparation of Compound 11-4

Compound 11-4 was obtained in the same manner as in the production of 1-4 in Production Example 1, except that Compound 4-3 was used instead of Compound 1-3.

Preparation of Compound 11-5

Compound 11-5 was obtained in the same manner as in the production of 1-5 in Preparative Example 1, except that Compound 4-4 was used in place of Compound 1-4.

compound P11 Manufacturing

The target compound P11 was obtained in the same manner as in the production of P1 in Production Example 1 except that the compound 4-5 was used instead of the compound 1-5.

In Preparation Example 11, Ar of S-1 was applied as shown in the following Table 11 to prepare Compounds 49 and 50.

compound No . Ar compound No . Ar 49

50

[Preparation Example 12] Preparation of a compound having a substituent shown in the following Table 12

Preparation of Compound 12-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 1- (4-bromopyridin-2-yl) ethan-1-one (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1 N HCl, aqueous NaHCO ₃ solution and H ₂ O. The extract was separated and purified by column chromatography to obtain 12-1.

Preparation of Compound 12-2

Compound 12-2 was obtained in the same manner as in the production of 5-2 in Production Example 5 except that Compound 12-1 was used instead of Compound 5-1.

Preparation of Compound 12-3

Compound 12-3 was obtained in the same manner as in the production of 5-3 in Production Example 5, except that Compound 12-2 was used instead of Compound 5-2.

Preparation of Compound 12-4

Compound 12-4 was obtained in the same manner as in the production of 5-4 in Production Example 5 except that Compound 12-3 was used instead of Compound 5-3.

Preparation of Compound 12-5

Compound 12-5 was obtained in the same manner as in the production of 5-5 in Production Example 5, except that Compound 12-4 was used instead of Compound 5-4.

compound P12 Manufacturing

Compound P12 was obtained in the same manner as in the production of P5 in Production Example 5, except that Compound 12-5 was used instead of Compound 5-5.

In Production Example 12, Ar of S-1 was applied as shown in the following Table 12 to produce compounds 99 and 100.

compound No . Ar compound No . Ar 99

100

[Preparation Example 13] Preparation of a compound having a substituent shown in the following Table 13

Preparation of Compound 13-1

Methyl-2-bromobenzoate (1 eq.) Was dissolved in 180 mL of THF, followed by addition of NaH (2 eq.) And stirring for 30 minutes. After stirring, 1- (5-bromonaphthalen-2-yl) ethan-1-one (1 eq.) Was slowly added dropwise. The mixture was stirred at room temperature for 2 hours and heated at 100 占 폚 for 16 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted successively with ethyl acetate, 1N HCl, aqueous NaHCO ₃ solution, and H ₂ O. The extract was separated and purified by column chromatography to obtain 13-1.

Preparation of Compound 13-2

Compound 13-2 was obtained in the same manner as in the production of 5-2 in Production Example 5 except that Compound 13-1 was used instead of Compound 5-1.

Preparation of Compound 13-3

Compound 13-2 was prepared in the same manner as in the production of 5-3 in Production Example 5, except that Compound 13-2 was used instead of Compound 5-2.

Preparation of Compound 13-4

Compound 13-4 was obtained in the same manner as in the production of 5-4 in Production Example 5 except that Compound 13-3 was used instead of Compound 5-3.

Preparation of Compound 13-5

Compound 13-5 was obtained in the same manner as in the production of 5-5 in Production Example 5 except that Compound 13-4 was used instead of Compound 5-4.

compound P13 Manufacturing

Compound P13 was obtained in the same manner as in the production of P5 in Production Example 5, except that Compound 13-5 was used instead of Compound 5-5.

In Preparation Example 13, Ar of S-1 was applied as shown in the following Table 13 to prepare Compounds 96 to 98.

compound No . Ar compound No . Ar 96

98

97

The compounds were prepared in the same manner as in the above Preparation Examples, and the results of confirmation of the synthesis are shown in Table 14 below.

NO ^One 1 H NMR ( CDCl ₃ , 300 Mz ) Found calculated One 2H), 7.84-7.83 (m, 4H), 7.58-7.49 (m, 10H), 7.25 (d, 766.91 766.28 2 2H), 8.13-7.96 (m, 9H), 7.84-7.79 (m, 5H), 7.58-7.49 (m, 8H), 7.25 (d, 6.53 (s, 2 H) 766.91 766.28 3 2H), 8.14-7.96 (m, 12H), 7.64-7.49 (m, 10H), 7.25 (d, 4H), 6.53 766.91 766.28 4 2H), 8.15-7.96 (m, 12H), 7.84-7.83 (t, 4H), 7.64-7.49 (m, 766.91 766.28 5 (d, 1H), 7.69 (d, 1H), 7.83 (d, 1H) 7.49 (m, 8H), 7.25 (m, 12H), 6.56 (s, 2H) 919.10 918.35 6 2H), 1.69 (s, 6H), 7.58 (d, 2H) 833.01 832.33 7 2H), 2.09 (t, 4H), 1.51 (t, 4H), 7.51 (d, 859.05 858.35 8 (m, 8H), 7.96-7.78 (m, 12H), 7.58-7.49 (m, 8H), 7.26-7.18 957.15 956.36 9 2H), 7.05 (d, 2H), 7.25 (d, 2H), 7.15 (d, 6.53 (s, 2 H), 2.19 (s, 6 H) 985.21 984.39 10 2H), 7.84-7.76 (m, 8H), 7.58-7.49 (m, 8H), 7.25 (d, 806.93 806.28 11 2H), 7.25 (d, 4H), 6.53 (s, 2H), 7.18-7.96 (m, 806.93 806.28 12 8H), 7.25 (d, 4H), 6.53 (s, 2H), 7.30-7. 806.93 806.28 13 4H), 7.25 (d, 4H), 6.53 (s, 2H), 7.30-7. 822.99 822.26 14 (m, 8H), 7.58-7.49 (m, 8H), 7.84-7.83 (m, 2H) 7.25 (d, 4 H), 6.53 (s, 2 H) 822.99 822.26 15 2H), 7.25 (d, 4H), 6.53 (s, 2H), 7.30-7.86 (m, 822.99 822.26 16 4H), 8.13-7.96 (m, 10H), 7.84-7.75 (m, 6H), 7.58-7.49 (m, 8H), 7.25 ), 6.53 (s, 2 H) 816.97 816.30 17 8H), 7.25 (d, 4H), 6.53 (s, 2H), 8.13-7.83 (m, 816.97 816.30 18 8H), 7.25-7.24 (m, 8H), 6.53 (s, 2H), 7.85-7.83 (m, 6H) ), 1.69 (s, 6H) 849.01 848.33 19 2H), 7.18 (d, 2H), 7.18 (d, 2H), 7.83-7.76 (m, 6H), 7.58-7.49 6.53 (s, 2 H), 1.69 (s, 6 H) 849.01 848.33 20 2H), 7.37 (m, 4H), 7.25 (d, 4H), 6.53 (s, 2H), 7.30-7.83 (m, 816.97 816.30 21 12H), 7.39-7.38 (m, 4H), < RTI ID = 0.0 > ), 6.53 (s, 2 H) 867.03 866.32 22 2H), 8.51 (s, 2H), 8.15-7.83 (m, 16H), 7.64-7.49 (m, 12H), 7.38 s, 2H) 867.03 866.32 23 2H), 6.53 (s, 2H), 7.38 (d, 2H), 8.57-8.51 (m, 4H), 8.15-7.83 867.03 866.32 24 8H), 7.93-7.83 (m, 6H), 7.69-7.72 (m, 4H), 7.58-7.54 (m, 8H) ), 6.53 (s, 2 H) 768.88 768.27 25 8H), 6.53 (s, 2H), 7.83 (d, IH) 768.88 768.27 26 2H), 7.61-7.49 (m, 12H), 7.84-7.83 (m, 4H) 7.39 (m, 2 H), 6.53 (s, 2 H) 766.91 766.28 27 2H), 7.84-7. 49 (m, 18H), 6.53 (s, 2H), 8.14-8. 766.91 766.28 28 (m, 2H), 7.83-7.54 (m, 18H), 6.53 (s, 2H) 766.91 766.28 29 2H), 8.38 (d, 2H), 8.15-8.06 (m, 8H), 7.94 (m, 2H), 7.83-7.49 766.91 766.28 30 (m, 8H), 7.94 (m, 2H), 7.84-7.69 (m, 8H), 7.61-7.49 (m, 10H) ), 7.25 (s, 8 H), 6.53 (s, 2 H) 919.10 918.35 31 2H), 1.69 (s, 6H), 7.63-7.30 (m, 10H) 833.01 832.33 32 2H), 2.09 (t, 4H), 1.51 (t, 4H), 7.51 (d, 859.05 858.35 33 10H), 7.26-7.18 (m, 10H), 6.53 (s, 2H), 8.13-8.06 (m, 8H), 7.94-7.73 ) 957.15 956.36 34 4H), 7.05 (d, 4H), 7.13 (d, 2H), 8.13-8.06 (m, 8H), 7.994-7.73 6.53 (s, 2 H), 2.19 (s, 6 H) 985.21 984.39 35 2H), 8.13-8.03 (m, 8H), 7.84-7.73 (m, 10H), 7.61-7.49 (m, 806.93 806.28 36 2H), 8.13-8.02 (m, 10H), 7.84-7.73 (m, 6H), 7.61-7.49 (m, 806.93 806.28 37 2H), 8.13-8.06 (m, 6H), 7.94-7.73 (m, 14H), 7.61-7.49 (m, 806.93 806.28 38 2H), 8.24-8.06 (m, 12H), 7.84-7.73 (m, 6H), 7.61-7.49 (m, 822.99 822.26 39 2H), 8.38 (d, 2H), 8.13-8.06 (m, 6H), 7.94 (s, 2H), 7.84-7.49 s, 2H) 822.99 822.26 40 2H), 7.61-7.49 (m, 10H), 6.53 (s, 2H), 8.38 (d, 2H), 8.13-7.99 (m, 14H), 7.84-7.83 822.99 822.26 41 (m, 6H), 7.94-7.73 (m, 8H), 7.61-7.49 (m, 10H) ), 6.53 (s, 2 H) 816.97 816.30 42 6H), 7.94-7.73 (m, 10H), 7.61-7.49 (m, 10H), 6.53 (s, 2H), 8.46-8.38 ) 816.97 816.30 43 (m, 2H), 7.73 (m, 2H), 7.58-7.49 (d, 2H) m, 10H), 7.25-7.24 (m, 4H), 6.53 (s, 2H), 1.69 849.01 848.33 44 2H), 8.13 (d, 2H), 8.06 (d, 4H), 7.94 (s, 2H), 7.84-7.73 (m, 8H), 7.61-7.49 d, 2H), 6.53 (s, 2H), 1.69 (s, 6H) 849.01 848.33 45 2H), 7.94-7.73 (m, 6H), 7.61-7.49 (m, 10H), 7.37 (m, 4H) 6.53 (s, 2 H) 816.97 816.30 46 2H), 8.23 (d, 2H), 8.13-8.03 (m, 12H), 7.84-7.77 (m, 6H), 7.58-7.49 7.39 (d, 2 H), 6.53 (s, 2 H) 867.03 866.32 47 8H), 8.43 (d, 2H), 8.29-8.23 (m, 4H), 8.14-8.03 (m, 12H), 7.84-7.77 (m, 6H), 7.58-7.49 ), 6.53 (s, 2 H) 867.03 866.32 48 2H), 8.50 (d, 2H), 8.23-8.06 (m, 16H), 7.84-7.77 (m, 6H), 7.58-7.49 867.03 866.32 49 (m, 4H), 7.72-7.69 (m, 4H), 7.62-7.69 (m, 2H) 7.58-7.49 (m, 8 H), 6.53 (s, 2 H) 768.88 768.27 50 2H), 8.50 (d, 2H), 8.31-8.00 (m, 1H), 7.84-7.58 (m, 4H), 7.58- 7.49 (m, 8 H), 6.53 (s, 2 H) 768.88 768.27 51 (m, 8H), 8.13 (m, 2H), 8.05 (d, 2H), 7.85-7.83 6.53 (s, 2 H) 766.91 766.28 52 7H), 7.69 (d, 1H), 7.58-7.50 (m, 8H), 8.35-8.28 (m, 9H) ), 7.25 (d, 2 H), 6.53 (s, 2 H) 766.91 766.28 53 8H), 8.14-8.13 (m, 4H), 7.84-7.83 (m, 4H), 7.64-7.50 (m, 10H), 7.25 ), 6.3 (s, 2 H) 766.91 766.28 54 8H), 8.15-8.13 (m, 4H), 7.84-7.83 (m, 4H), 7.64-7.50 (m, 10H), 7.25 ), 6.53 (s, 2 H) 766.91 766.28 55 (d, 1H), 7.58-7.50 (m, 8H), 8.35-8.28 (m, 9H), 8.13-8.07 (m, 4H), 7.85-7.79 ), 7.25 (s, 8 H), 6.53 (s, 2 H) 919.10 918.35 56 8H), 6.53 (s, 2H), 1.69 (s, 6H), 7.89-7.75 ) 833.01 832.33 57 8H), 6.53 (s, 2H), 2.09 (t, 4H), 7.85-7.78 (m, ), 1.51 (t, 4H) 859.05 858.35 58 (m, 8H), 8.13-8.09 (m, 4H), 7.85-7.78 (m, 12H), 7.58-7.50 , 2H) 975.15 956.36 59 8H), 7.13 (d, 2H), 7.05 (d, 2H < RTI ID = 0.0 > ), 6.53 (s, 2 H), 2.19 (s, 6 H) 985.21 984.39 60 (m, 8H), 8.13 (d, 2H), 8.03 (d, 2H), 7.85-7.76 (m, 12H), 7.58-7.50 806.93 806.28 61 8H), 8.13-8.02 (m, 6H), 7.84-7.83 (m, 4H), 7.58-7.50 (m, 10H), 7.25 ) 806.93 806.28 62 (m, 8H), 8.13 (m, 2H), 7.88-7.83 (m, 14H), 7.58-7.50 806.93 806.28 63 (m, 8H), 7.53 (s, 2H), 7.58-7.50 (m, 8H) 822.99 822.26 64 8H), 8.13 (d, 2H), 7.84-7.83 (m, 4H), 7.70 (t, 2H), 7.58-7.50 (m, 8H) 7.25 (d, 4 H), 6.53 (s, 2 H) 822.99 822.26 65 8H), 7.53-8.12 (m, 6H), 7.99 (d, 2H), 7.85-7.83 ) 822.99 822.26 66 2H), 8.35-8.28 (m, 12H), 8.13 (d, 2H), 7.85-7.75 (m, 10H), 7.58-7.50 816.97 816.30 67 8H), 8.46-8.43 (m, 4H), 8.30-8.28 (m, 8H), 8.13 (d, 2H), 7.92-7.83 ), 6.53 (s, 2 H) 816.97 816.30 68 8H), 8.13 (m, 2H), 7.85-7.83 (m, 6H), 7.58-7.50 (m, 8H), 7.25-7.24 ), 1.69 (s, 6H) 849.01 848.33 69 (d, 2H), 6.53 (s, 2H), 7.18 (m, 2H), 7.83-7.76 1.69 (s, 6H) 849.01 848.33 70 2H), 7.37 (d, 4H), 7.25 (d, 4H), 6.53 (s, 2H), 7.30-7.83 (m, 4H) 816.97 816.30 71 2H), 7.38-7.38 (m, 4H), 6.53 (s, 2H), 8.13-7.83 (m, 14H), 7.58-7.50 867.03 866.32 72 4H), 8.00-7.83 (m, 10H), 7.64-7.50 (m, 12H), 8.14-8.13 (d, 2H) 7.38 (d, 2 H), 6.53 (s, 2 H) 867.03 866.32 73 4H), 8.15-8.13 (m, 4H), 8.00-7.83 (m, 10H), 7.61-7.50 (m, 12H), 7.38 (d, 2H ), 6.53 (s, 2 H) 867.03 866.32 74 (m, 4H), 7.72-7.69 (m, 4S), 7.58-7.50 (m, 8H) ), 6.48 (s, 2 H) 768.88 768.27 75 (m, 4H), 7.58-7.50 (m, 8H), 8.00 (m, 2H) 6.48 (s, 2H) 768.88 768.27 76 4H), 7.73 (t, 2H), 7.61-7.50 (m, 2H), 8.04 (m, m, 12H), 7.39 (d, 2H), 6.53 (s, 2H) 766.91 766.28 77 4H), 7.94 (m, 4H), 7.84-7.69 (m, 8H), 7.61 (d, 1H) 7.50 (m, 10 H), 6.53 (s, 2 H) 766.91 766.28 78 4H), 7.84-7.83 (m, 4H), 7.73-7.50 (m, 14H), 8.14-8.13 (dd, 6.53 (s, 2 H) 766.91 766.28 79 (m, 4H), 7.94-7.83 (m, 4H), 7.73-7.50 (m, 14H) 6.53 (s, 2 H) 766.91 766.28 80 (m, 4H), 7.84-7.73 (m, 8H), 7.61-7.50 (m, 10H), 8.13-8.07 ), 7.25 (s, 4 H), 6.53 (s, 2 H) 919.10 918.35 81 2H), 1.69 (s, 6H), 7.69 (d, IH), 7.30-7.75 (m, 4H) 833.01 832.33 82 4H), 7.94-7.83 (m, 14H), 7.61-7.50 (m, 10H), 6.53 (s, 2H), 2.09 1.51 (t, 4H) 859.05 858.35 83 (m, 4H), 7.94-7.70 (m, 14H), 7.61-7.50 (m, 10H), 7.28-7.10 ) 957.15 956.36 84 (m, 4H), 7.94-7.70 (m, 14H), 7.61-7.50 (m, 10H), 7.39 6.53 (s, 2 H), 2.19 (s, 6 H) 985.21 984.39 85 4H), 7.84-7.73 (m, 10H), 7.61-7.50 (m, 10H), 6.53 (m, 2H), 8.03 s, 2H) 806.93 806.28 86 2H), 7.61-7.50 (m, 12H), 6.53 (m, 4H), 7.83 (m, 4H) s, 2H) 806.93 806.28 87 2H), 7.94-7.73 (m, 16H), 7.61-7.50 (m, 10H), 6.53 (s, 2H) 806.93 806.28 88 2H), 7.61-7.50 (m, 10H), 6.53 (s, 2H), 7.73-7.83 (m, 4H) 822.99 822.26 89 4H), 7.73-7.50 (m, 14H), 7.94-7.83 (m, 2H) 6.53 (s, 2 H) 822.99 822.26 90 4H), 7.73 (t, 2H), 7.61-7.50 (m, 6H), 7.99-7.94 (m, 6H), 7.84-7.83 ), 6.53 (s, 2 H) 822.99 822.26 91 4H), 7.84-7.73 (m, 8H), 7.61-7.50 (m, 10H), 8.14 (m, 2H) 6.53 (s, 2 H) 816.97 816.30 92 (d, 2H), 7.94-7.73 (m, 12H), 7.61-7.50 (m, 10H) 6.53 (s, 2 H) 816.97 816.30 93 2H), 7.61-7.50 (m, 10H), 7.25-7.83 (m, 2H) 7.24 (m, 4H), 6.53 (s, 2H), 1.69 (s, 6H) 849.01 848.33 94 2H), 7.14 (m, 2H), 7.84-7.73 (m, 8H), 7.61-7.5 (m, s, 2 H), 1.69 (s, 6 H) 849.01 848.33 95 4H), 7.73 (t, 2H), 7.61-7.50 (m, 10H), 7.37 (d, 4H) 6.53 (s, 2 H) 816.97 816. 96 2H), 8.23-8.23 (m, 8H), 8.13-8.03 (m, 8H), 7.84-7.77 (m, 6H), 7.58-7.50 867.03 866.32 97 8H), 8.35-8.23 (m, 9H), 8.13-8.03 (m, 8H), 7.84-7.69 (m, 8H), 7.58-7.50 (m, 8H), 6.53 , 2H) 867.03 866.32 98 2H), 8.50 (d, 2H), 8.28-8.03 (m, 13H), 7.84-7.77 (m, 6H), 7.64-7.50 867.03 866.32 99 (m, 2H), 7.93 (m, 2H), 7.84-7.83 (m, 2H), 8.52 (d, 2H) 4H), 7.72-7.69 (m, 69 (m, 4H), 7.48-7.50 (m, 8H), 6.48 786.88 786.27 100 2H), 8.50 (m, 2H), 8.31-8.25 (m, 6H), 8.18-8.10 (m, 4H), 8.00 (d, 2H) (m, 4H), 7.58-7.50 (m, 8H), 6.48 (s, 2H) 867.03 866.32 101 7H), 7.58-7.49 (m, 10H), 7.39 (d, 2H), 7.85-7.83 (m, 6H) 2H), [delta] 7.25 (d, 2H), 6.53 (s, 2H) 766.91 766.28 102 8H), 7.25 (d, 2H), 6.53 (s, 2H), 7.89-7.78 (m, ), 1.69 (s, 6H) 833.01 832.33 103 12H), 7.58-7.50 (m, 8H), 7.25-7.18 (m, 12H), 6.53 (s, 1H), 8.13-8.06 , 2H) 957.15 956.36 104 8H), 7.25 (d, 2H), 6.53 (s, 2H), 7.30-8. ), 2.21-1.96 (tt, 4H), 1.73-1.63 (m, 4H) 859.05 858.35 105 8H), 7.25 (d, 2H), 6.53 (s, 2H), 7.85-7.83 ) 822.99 822.26 106 8H), 7.25 (d, 2H), 7.13-7.05 (dd, < RTI ID = , 4H), 6.53 (s, 2H), 2.19 (s, 6H) 822.99 822.26 107 8H), 7.25 (d, 2H), 7.13-7.05 (dd, < RTI ID = 0.0 > , 4H), 6.53 (s, 2H), 2.19 (s, 6H) 985.21 984.39 108 8H), 7.25 (d, 2H), 6.53 (s, 2H), 7.30-7.96 ) 806.93 806.28 109 (m, 4H), 7.96 (m, 2H), 7.88-7.79 (m, 12H), 7.56-7.49 ), 6.53 (s, 2 H) 806.93 806.28 110 8H), 7.37 (d, 4H), 7.25 (d, 4H), 7.85-7.83 (m, 6.53 (s, 2 H) 816.97 816.30

[Example 1] Production of organic light emitting device

An organic electroluminescent device was prepared in the following manner.

The substrate with ITO thickness of 1500 Å was immersed in distilled water and washed with an ultrasonic cleaner. After the distilled water was washed, it was ultrasonically washed with a solvent such as acetone, methanol, isopropyl alcohol, dried to remove water, and treated with UVO for 5 minutes in a UV scrubber. Subsequently, the substrate was transferred to a plasma cleaner (PT), plasma treatment was performed to improve the hole injection characteristics of the organic device and to remove the residual film, and the substrate was transferred to a thermal vapor deposition apparatus for vapor deposition.

N, N'-bis (a-naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'- naphthyl) -N, N'-diphenyl-4,4'-diamine: NPB) was deposited in a thickness of 400 Å by thermal vacuum deposition to form a hole transport layer.

NPB

After forming a hole transporting layer, a light emitting layer was formed thereon by thermal vacuum deposition as follows. The light-emitting layer CBP (4,4'N, N '-dicarbazole- biphenyl), a green phosphorescent dopant _{Ir (ppy) 3 (tris (} 2-phenylpyridine) iridium) of the Ir (ppy) ₃ in CBP 7 with the host % ≪ / RTI > Then, BCP was deposited to a thickness of 100 Å as a hole blocking layer. As an electron transport layer, compounds 1 to 4, 6, 16, 19 to 21, 26, 49, 52, 71, 74 and 76 And 101 were deposited in a thickness of 200Å. Finally, lithium fluoride was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer. An aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1200 Å to form a cathode. .

CBP Ir ( ppy ) ₃ BCP

[Comparative Example 1] Fabrication of an organic light emitting device

Alq ₃ was used instead of the compounds 1 to 4, 6, 16, 19 to 21, 26, 49, 52, 71, 74, 76 and 101 in the compounds synthesized in Production Examples 1 to 13 used in forming the electron transport layer in Example 1 , An organic electroluminescent device was fabricated in the same manner as in Example 1.

Alq ₃

[Experimental Example 1] Driving voltage and luminous efficiency of an organic electroluminescent device

The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated in the above-described Example 1 and Comparative Example 1 were measured by M7000 of Mitsubishi Electric Corporation, and the results of the measurement were used to determine the lifetime The T ₉₀ was measured with a reference luminance of 6000 cd / m ² through the equipment (M6000). Table 15 shows the results of measuring the driving voltage, the luminance, the luminous efficiency, and the lifetime of the organic EL device manufactured according to Example 1 and Comparative Example 1 of the present invention.

Electron transport layer Driving voltage
(V) Luminance
(cd / m ² ) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T ₉₀ ) Compound 1 4.89 6000 52.14 (0.295, 0.634) 54.8 Compound 2 4.76 6000 53.21 (0.292, 0.633) 55.3 Compound 3 4.92 6000 51.38 (0.294, 0.632) 53.5 Compound 4 4.99 6000 52.13 (0.295, 0.634) 56.2 Compound 6 4.68 6000 51.79 (0.295, 0.631) 54.3 Compound 16 4.59 6000 51.98 (0.295, 0.635) 54.6 Compound 19 4.86 6000 53.47 (0.293, 0.634) 56.7 Compound 20 4.76 6000 52.13 (0.292, 0.634) 52.3 Compound 21 4.63 6000 50.86 (0.293, 0.633) 52.7 Compound 26 4.87 6000 53.23 (0.294, 0.635) 55.1 Compound 49 4.68 6000 52.43 (0.294, 0.632) 52.3 Compound 52 4.74 6000 53.99 (0.295, 0.632) 56.2 Compound 71 4.82 6000 54.12 (0.295, 0.633) 55.2 Compound 74 4.73 6000 51.23 (0.293, 0.631) 52.3 Compound 76 4.81 6000 51.55 (0.295, 0.633) 56.7 Compound 101 4.93 6000 50.35 (0.295, 0.634) 52.3 Alq ₃ 5.24 6000 48.15 (0.293, 0.635) 50.3

As shown in Table 15, when the compound of the present application is used as the electron transport layer material of the organic electroluminescent device, the driving voltage is lower than that of the conventional Alq ₃ , the luminous efficiency is improved, and the lifetime is significantly improved .

100 substrate
200 anode
300 organic layer
301 hole injection layer
302 hole transport layer
303 luminous layer
304 hole stop layer
305 electron transport layer
306 electron injection layer
400 cathode

Claims (17)

A compound of formula
[Chemical Formula 1]

In Formula 1,
L1 to L3 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic arylene; Or a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroarylene,
t is an integer from 0 to 5,
R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C ₁ to C ₆₀ straight or branched alkyl; Substituted or unsubstituted C ₂ to C ₆₀ straight or branched chain alkenyl; Substituted or unsubstituted C ₂ to C ₆₀ straight or branched chain alkynyl; A substituted or unsubstituted C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; Substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; Substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl; -SiRR'R "; -P (= O) RR 'and -NRR'
Wherein R, R 'and R "are the same or different from each other and each independently represents hydrogen, C ₁ to C ₆₀ linear or branched alkyl, substituted or unsubstituted C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl C ₆ to C ₆₀ monocyclic or polycyclic aryl, and C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl,
m and n are each independently an integer of 0 to 4,
p and q are each independently an integer of 0 to 2,
When m, n, p, q, and t are each an integer of 2 or more, the substituents in each parenthesis are the same or different from each other. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
R 1, R 2, R 3, R 4, m and n are the same as defined in formula (1)
R5 and R6 are the same as defined in R1 of formula (1). The compound according to claim 1, wherein L1 to L3 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ monocyclic or polycyclic arylene; Or a substituted or unsubstituted C ₂ to C ₂₀ monocyclic or polycyclic heteroarylene. The compound according to claim 1, wherein L1 and L3 are the same or different from each other and each independently selected from the group consisting of phenylene, biphenylene, naphthylene, anthracenylene, pyridylene, pyrimidylene, and triazienylene,
A C ₁ ~ C ₂₀ alkyl, C ₆ ~ C ₂₀ aryl, or C ₂ ~ C ₂₀ heteroaryl further substituted by one or being unsubstituted compound. The compound according to claim 1, wherein L 2 is selected from the group consisting of phenylene, biphenylene, naphthylene, anthracenylene, phenanthrene, klychenylene, pyrenylene, triphenylenylene, pyridylene, pyrimidylene, But are not limited to, fluorene, spirocyclopentane fluorene, dibenzothiophenylene, dibenzoselenophenylene, dibenzosylolylene, acridinylene, xanthenylene, thioxanthrenylene , Dibenzosilinylene, and selenoxanthrenylene,
A C ₁ ~ C ₂₀ alkyl, C ₆ ~ C ₂₀ aryl, or C ₂ ~ C ₂₀ heteroaryl further substituted by one or being unsubstituted compound. The compound according to claim 1, wherein t is an integer of 1 to 3. [4] The compound according to claim 1, wherein R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl. The compound according to claim 2, wherein R1 to R6 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; And substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl. The compound according to claim 2, wherein at least one of R 1 to R 6 is a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl. 3. The compound of claim 2, wherein R1, R2, R5 and R6 are the same or different from each other, and each independently hydrogen; Or deuterium. The compound according to claim 2, wherein R 3 and R 4 are the same or different and each independently is a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl. 2. The compound according to claim 1, wherein said formula (1) is selected from the following formulas:

1. An organic light emitting device comprising: an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of any one of claims 1 to 12. [14] The organic light emitting device according to claim 13, wherein the organic compound layer comprising the compound of Formula 1 is at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. [14] The organic light emitting device according to claim 13, wherein the organic material layer including the compound of Formula 1 is an electron transport layer. [14] The organic light emitting device according to claim 13, wherein the organic material layer including the compound of Formula 1 is a hole blocking layer. [14] The organic light emitting device according to claim 13, wherein the organic material layer including the compound of Formula 1 is a light emitting layer.

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