KR20220116604A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention is an organic light emitting compound represented by chemical formula I. When the organic light emitting compound is employed in an electron transport layer, a hole blocking layer, etc., it is possible to implement an organic light emitting device having very excellent light emitting properties such as low voltage driving characteristics, long lifespan, and light emitting efficiency.

Description

An organic light emitting compound and an organic light emitting device comprising the same

The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound employed in an organic layer in an organic light emitting device and an organic light emitting device having significantly improved light emitting characteristics such as low voltage driving characteristics, long lifespan, and luminous efficiency by employing the same. .

The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.

However, in order for the organic light emitting device to exhibit the above characteristics, the material constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a hole blocking material, an electron blocking material, etc. It should be supported by a stable and efficient material, but the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed. Accordingly, the development of a new material capable of improving light emitting characteristics and development of an organic layer structure in a device are continuously required.

Accordingly, the present invention is a novel organic light-emitting compound that can significantly improve light-emitting properties such as low voltage driving characteristics, long lifespan, and luminous efficiency by being employed as an organic layer material such as an electron transport layer and a hole blocking layer in an organic light-emitting device, and an organic light-emitting compound containing the same An object of the present invention is to provide a light emitting device.

In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following [Formula I] and an organic light emitting device including the same in an organic layer in the device.

[Formula Ⅰ]

The specific structure of the [Formula I] and specific compounds and L, X ₁ to X ₃ , Y, A, B and C implemented thereby will be described later.

The organic light emitting device employing the organic light emitting compound according to the present invention in an organic layer such as an electron transport layer and a hole blocking layer has significantly superior light emitting characteristics such as low voltage driving characteristics, long lifespan, and luminous efficiency compared to conventional devices, making it useful for various display devices. can be used

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic light emitting compound represented by the following [Formula I], and when employed in various organic layers in an organic light emitting device, preferably an electron transport layer, a hole blocking layer, etc., low voltage driving characteristics, long life, luminous efficiency, etc. It is possible to realize an organic light emitting device with significantly improved light emitting characteristics.

The organic light emitting compound represented by the following [Formula I] according to the present invention is structurally,

(i) introducing a structure represented by the following [Structural Formula 3] at the C position in the skeleton of dibenzofuran, dibenzothiophene, fluorene, carbazole, etc.;

(ii) pyridine (pyrimidine, triazine) derivatives are introduced,

(iii) [Formula I] according to the present invention is characterized in that it contains at least one cyano group (CN) through A, B and C.

Through these structural features, it is possible to implement an organic light emitting device with significantly improved light emitting characteristics such as low voltage driving characteristics, long lifespan, and luminous efficiency by employing the electron transport layer and hole blocking layer in the device.

[Formula Ⅰ]

In the above [Formula I],

X _One To X ₃ Are the same as or different from each other, each independently represents N or CH, and at least one of X _One To X ₃ is N.

Y is CR ₁ R ₂ , NR ₃ , O or S, wherein R ₁ to R ₃ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, substituted or unsubstituted It is selected from a cyclic cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In addition, R ₁ and R ₂ may be combined with each other to form an alicyclic ring or an aromatic ring.

A is represented by the following [Structural Formula 1], B is represented by the following [Structural Formula 2], and C is represented by the following [Structural Formula 3].

[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

In the [Structural Formula 1] to [Structural Formula 3],

L and L ₁ to L ₃ are the same as or different from each other, and each independently is a single bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or It is selected from an unsubstituted benzoxazolylene group and a substituted or unsubstituted benzothiazolylene group.

p is an integer of 0 to 2, and when p is 2, a plurality of L's are the same as or different from each other.

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, cycloalkyl or heterocycloalkyl. A substituted or unsubstituted C 6 to C 30 aryl group, cycloalkyl or heterocycloalkyl fused or more fused or unsubstituted substituted or unsubstituted C 3 to C 30 heteroaryl group, substituted or unsubstituted selected from a fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole, and a substituted or unsubstituted benzothiazole.

Ar ₃ is a direct bond (not defined as non-existent), a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzoxazole, and a substituted or unsubstituted cyclic benzothiazoles.

CN means a cyano group.

n and m are each an integer from 0 to 2, and o is an integer from 0 to 1.

However, as n + m + o ≥ 1, the organic light emitting compound represented by [Formula I] according to the present invention is characterized in that it contains at least one cyano group (CN).

On the other hand, substituted or unsubstituted means that R ₁ to R ₃ , L, L ₁ to L ₃ and Ar ₁ to Ar ₃ are deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, halogenated alkyl group, alkoxy group, respectively. , a halogenated alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, and substituted with one or more substituents selected from a silyl group, or substituted with a substituent to which two or more of the substituents are linked, or any substituents means not having

For specific examples, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. are substituted with other substituents do.

The substituted heteroaryl group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and a condensed heterocyclic group thereof, such as a benzquinoline group, a benz It means that an imidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, etc. are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, but is not limited thereto.

In the present invention, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl. and the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

,

,

등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example,

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

,

,

,

등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example,

,

,

,

etc.

In addition, in the present invention, the fluorenyl group may be a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring are further condensed in the linked structure or an open structure.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N, or S as a heteroatom, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 30 carbon atoms. Examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, iso An oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and the like, but are not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohex Sil group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo octyl group, spirodecyl, spirodecyl, adamantyl, etc., but are not limited thereto, and may be further substituted by other substituents, and polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group As such, the other ring group may be a cycloalkyl group, but may be a different type of ring group such as a heterocycloalkyl group, an aryl group, or a heteroaryl group.

In the present invention, the heterocycloalkyl group includes heteroatoms such as O, S, Se, N or Si, and also includes monocyclic or polycyclic, and may be further substituted by other substituents, and polycyclic means heterocyclo The alkyl group refers to a group directly connected or condensed with another ring group, and the other ring group may be a heterocycloalkyl group, but may be a different type of ring group such as a cycloalkyl group, an aryl group, or a heteroaryl group.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In addition, various specific examples of the substituent according to the present invention can be clearly identified in the specific compounds described below.

The organic light emitting compound according to the present invention represented by the above [Formula I] can be used as an organic layer of an organic light emitting device due to its structural specificity as described above, and more specifically, the electrons of the organic layer according to the characteristics of various substituents introduced It can be used as a material for a transport layer, a hole blocking layer, and the like.

Preferred examples of the compound represented by [Formula I] according to the present invention include the following compounds, but are not limited thereto.

As described above, in the present invention, an organic light emitting compound having a skeleton and a unique characteristic of the substituent can be synthesized by introducing a substituent in a skeleton having a characteristic structure and a characteristic position. For example, an organic light emitting compound material that satisfies the conditions required for each organic layer, such as an electron transport layer and a hole blocking layer, can be prepared when manufacturing an organic light emitting device. , when employed in the hole blocking layer, it is possible to further improve the light emitting characteristics such as low voltage driving characteristics, long lifespan, and luminous efficiency of the device.

The organic light emitting compound according to the present invention can be applied to an organic light emitting device according to a conventional manufacturing method.

The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using a conventional device manufacturing method and material.

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.

Accordingly, in the organic light emitting device according to the present invention, the organic layer may include an electron transport layer or a hole blocking layer, and at least one of the layers may include the organic light emitting compound represented by the [Formula I].

In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al Structural materials and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light-emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and Benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention can act on a principle similar to that applied to the organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, an organic transistor, and the like.

Hereinafter, synthesis examples and device examples of preferred compounds are provided to help the understanding of the present invention. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereby.

Synthesis example 1: Synthesis of compound 12

(One) production example 1: Synthesis of Intermediate 12-1

2,4-Dichloro-6-phenyl-1,3,5-triazine (10.0 g, 0.044 mol), 4-Cyanophenylboronic acid (7.8 g, 0.053 mol), K ₂ CO ₃ (18.3 g, 0.133 mol), Pd 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O were added to (PPh ₃ ) ₄ (1.0 g, 0.001 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.2 g (yield 55.6%) of <Intermediate 12-1>.

(2) production example 2: Synthesis of compound 12

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), Intermediate 12-1 (12.2 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.2 g (yield 70.2%) of <Compound 12>.

LC/MS: m/z=500[(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 36

(One) production example 1: Synthesis of Intermediate 36-1

4-(4-Bromophenyl)-6-phenyldibenzofuran (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (4.9 g, 0.050 mol), Pd(dppf)Cl ₂ (0.5 g , 0.0008 mol) was added with 200 Ml of Dioxane and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.9 g (yield 71.1%) of <Intermediate 36-1>.

(2) production example 2: Synthesis of compound 36

Intermediate 36-1 (10.0 g, 0.022 mol), Intermediate 12-1 (7.9 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.4 g (yield 70.3%) of <Compound 36>.

LC/MS: m/z=576[(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 58

(One) production example 1: Synthesis of intermediate 58-1

Toluene 200 in Cyanuric chloride (10.0 g, 0.054 mol), 4-Cyanophenylboronic Acid (19.1 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd(PPh ₃ ) ₄ (1.3 g, 0.001 mol) mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.5 g (yield 66.8%) of <Intermediate 58-1>.

(2) production example 2: Synthesis of compound 58

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 58-1 (13.2 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 12.5 g (yield 68.5%) of <Compound 58> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=525[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 106

(One) production example 1: Synthesis of intermediate 106-1

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 4-Cyanophenylboronic acid (5.4 g, 0.037 mol), K ₂ CO ₃ (12.7 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL was added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 5.8 g (yield 54.3%) of <Intermediate 106-1>.

(2) production example 2: Synthesis of compound 106

Intermediate 106-1 (10.0 g, 0.031 mol), 4-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenylboronic acid (13.0 g, 0.037 mol), K ₂ CO ₃ (12.7 g , 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 75.2%) of <Compound 106>.

LC/MS: m/z=576[(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 110

(One) production example 1: Synthesis of intermediate 110-1

Intermediate 106-1 (10.0 g, 0.029 mol), 1,4-Phenylenediboronic acid (5.7 g, 0.035 mol), K ₂ CO ₃ (11.9 g, 0.086 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.5 g (yield 67.1%) of <Intermediate 110-1>.

(2) production example 2: Synthesis of compound 110

Intermediate 110-1 (10.0 g, 0.026 mol), 2-Chloro-4,6-di(biphenyl-3-yl)-1,3,5-triazine (13.0 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.077 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was added with 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100° C. for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.9 g (yield 68.9%) of <Compound 110>.

LC/MS: m/z=728 [(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 119

(One) production example 1: Synthesis of Intermediate 119-1

Intermediate 106-1 (10.0 g, 0.029 mol), 1,3-Benzenediboronic acid (5.7 g, 0.035 mol), K ₂ CO ₃ (11.9 g, 0.086 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.2 g (yield 55.5%) of <Intermediate 119-1>.

(2) production example 2: Synthesis of compound 119

Intermediate 119-1 (10.0 g, 0.026 mol), 2-Chloro-4-(3-dibenzofuranyl)-6-phenyl-1,3,5-triazine (11.0 g, 0.031 mol), K ₂ CO ₃ (10.7 g , 0.077 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.7 g (yield 68.3%) of <Compound 119>.

LC/MS: m/z=666[(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 126

(One) production example 1: Synthesis of compound 126

Intermediate 110-1 (10.0 g, 0.026 mol), 2-(4-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.077) mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was added with 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100° C. for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.5 g (yield 74.5%) of <Compound 126>.

LC/MS: m/z=652 [(M+1) ⁺ ]

Synthesis example 8: Synthesis of compound 167

(One) production example 1: Synthesis of intermediate 167-1

Intermediate 106-1 (10.0 g, 0.029 mol), Naphthalene-1,4-diboronic acid (7.4 g, 0.035 mol), K ₂ CO ₃ (11.9 g, 0.086 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 7.5 g (yield: 59.5%) of <Intermediate 167-1>.

(2) production example 2: Synthesis of intermediate 167-2

4-Bromo-2,6-diiodopyridine (10.0 g, 0.024 mol), 4-Cyanophenylboronic acid (8.6 g, 0.059 mol), K ₂ CO ₃ (20.2 g, 0.146 mol), Pd(PPh ₃ ) ₄ (0.6 g , 0.0005 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 5.5 g (yield 62.6%) of <Intermediate 167-2>.

(3) production example 3: Synthesis of compound 167

Intermediate 167-1 (10.0 g, 0.023 mol), Intermediate 167-2 (9.8 g, 0.027 mol), K ₂ CO ₃ (9.4 g, 0.068 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.6 g (yield 62.5%) of <Compound 167>.

LC/MS: m/z=674 [(M+1) ⁺ ]

Synthesis example 9: Synthesis of compound 176

(One) production example 1: Synthesis of intermediate 176-1

Cyanuric chloride (10.0 g, 0.054 mol), 4-Cyano-[1,1'-biphenyl]-4'-boronic acid (29.0 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd ( Toluene 200 mL, Ethanol 50 mL, and H ₂ O 50 mL were added to PPh ₃ ) ₄ (1.3 g, 0.001 mol), and the reaction was stirred at 100° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.8 g (yield 62.0%) of <Intermediate 176-1>.

(2) production example 2: Synthesis of compound 176

To intermediate 110-1 (10.0 g, 0.026 mol), intermediate 176-1 (14.5 g, 0.031 mol), K ₂ CO ₃ (10.6 g, 0.077 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.9 g (yield 69.5%) of <Compound 176>.

LC/MS: m/z=778 [(M+1) ⁺ ]

Synthesis example 10: synthesis of compound 184

(One) production example 1: Synthesis of Intermediate 184-1

Cyanuric chloride (10.0 g, 0.054 mol), 3,5-Dicyanophenylboronic acid (22.4 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd(PPh ₃ ) ₄ (1.3 g, 0.001 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.2 g (yield 66.2%) of <Intermediate 184-1>.

(2) production example 2: Synthesis of compound 184

To intermediate 110-1 (10.0 g, 0.026 mol), intermediate 184-1 (11.3 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.077 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.7 g (yield 61.5%) of <Compound 184>.

LC/MS: m/z=676 [(M+1) ⁺ ]

Synthesis example 11: Synthesis of compound 206

(One) production example 1: Synthesis of Intermediate 206-1

2,4-Dichloro-6-(3-dibenzofuranyl)-1,3,5-triazine (10.0 g, 0.032 mol), 4-Cyanobenzeneboronic acid (5.6 g, 0.038 mol), K ₂ CO ₃ (13.1 g, 0.095) mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.8 g (yield 56.2%) of <Intermediate 206-1>.

(2) production example 2: Synthesis of compound 206

4-Phenyldibenzothiophene-6-boronic acid (10.0 g, 0.033 mol), Intermediate 206-1 (15.1 g, 0.040 mol), K ₂ CO ₃ (13.6 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 14.8 g (yield 74.2%) of <Compound 206>.

LC/MS: m/z=606[(M+1) ⁺ ]

Synthesis example 12: Synthesis of compound 293

(One) production example 1: Synthesis of intermediate 293-1

4,6-Dibromodibenzothiophene (10.0 g, 0.029 mol), 4-Cyanophenylboronic acid (5.2 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL was added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 5.3 g (yield 49.8%) of <Intermediate 293-1>.

(2) production example 2: Synthesis of intermediate 293-2

Intermediate 293-1 (10.0 g, 0.028 mol), 1,4-Phenylenediboronic acid (5.5 g, 0.033 mol), K ₂ CO ₃ (11.4 g, 0.082 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 6.1 g (yield 54.8%) of <Intermediate 293-2>.

(3) production example 3: Synthesis of intermediate 293-3

2-(4-Biphenylyl)-4,6-dichloro-1,3,5-triazine (10.0 g, 0.033 mol), 9,9-Dimethylfluoren-2-boronic acid (9.5 g, 0.040 mol), K ₂ CO ₃ (13.7 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.5 g (yield 49.3%) of <Intermediate 293-3>.

(4) production example 4: Synthesis of compound 293

Intermediate 293-2 (10.0 g, 0.025 mol), Intermediate 293-3 (13.6 g, 0.030 mol), K ₂ CO ₃ (10.2 g, 0.074 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.9 g (yield 71.8%) of <Compound 293>.

LC/MS: m/z=784 [(M+1) ⁺ ]

Synthesis example 13: Synthesis of compound 319

(One) production example 1: Synthesis of intermediate 319-1

Dioxane 200 in Intermediate 293-1 (10.0 g, 0.028 mol), Bis(pinacolato)diboron (8.4 g, 0.033 mol), KOAc (5.4 g, 0.055 mol), Pd(dppf)Cl ₂ (0.6 g, 0.0008 mol) mL was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 8.5 g (yield 75.3%) of <Intermediate 319-1>.

(2) production example 2: Synthesis of intermediate 319-2

Intermediate 319-1 (10.0 g, 0.024 mol), 3-Bromo-1-iodobenzene (8.3 g, 0.029 mol), K ₂ CO ₃ (10.1 g, 0.073 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005) mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.8 g (yield 72.9%) of <Intermediate 319-2>.

(3) production example 3: Synthesis of compound 319

Intermediate 319-2 (10.0 g, 0.023 mol), 4-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenylboronic acid (9.7 g, 0.027 mol), K ₂ CO ₃ (9.4 g , 0.068 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0005 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.8 g (yield 71.1%) of <Compound 319>.

LC/MS: m/z=668[(M+1) ⁺ ]

Synthesis example 14: Synthesis of compound 347

(One) production example 1: Synthesis of intermediate 347-1

DMF was added to 4-Bromobenzenealdehyde (10.0 g, 0.054 mol), 4-Cyanobenzamidine hydrochloride (19.6 g, 0.108 mol), K ₂ CO ₃ (14.9 g, 0.108 mol), and the reaction was stirred at 120 ° C. under reflux for 18 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.4 g (yield 65.0%) of <Intermediate 347-1>.

(2) production example 2: Synthesis of compound 347

Intermediate 319-1 (10.0 g, 0.024 mol), Intermediate 347-1 (12.8 g, 0.029 mol), K ₂ CO ₃ (10.1 g, 0.073 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.3 g (yield 72.3%) of <Compound 347>.

LC/MS: m/z=642 [(M+1) ⁺ ]

Synthesis example 15: Synthesis of compound 377

(One) production example 1: Synthesis of intermediate 377-1

150 mL of DMF was added to 4,6-Dibromodibenzofuran (10.0 g, 0.031 mol) and Copper(I) cyanide (1.5 g, 0.015 mol), and the reaction was stirred under reflux at 150 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 3.8 g (yield 45.5%) of <Intermediate 377-1>.

(2) production example 2: Synthesis of intermediate 377-2

Intermediate 377-1 (10.0 g, 0.037 mol), Bis(pinacolato)diboron (11.2 g, 0.044 mol), KOAc (7.2 g, 0.074 mol), Dioxane 200 in Pd(dppf)Cl ₂ (0.8 g, 0.001 mol) mL was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.6 g (yield 73.3%) of <Intermediate 377-2>.

(3) production example 3: Synthesis of compound 377

Intermediate 377-2 (10.0 g, 0.031 mol), 2-([1,1'-Biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (12.9 g, 0.038 mol) ), K ₂ CO ₃ (13.0 g, 0.094 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added to 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, and stirred at 100 °C for 6 hours. and reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.2 g (yield 71.4%) of <Compound 377>.

LC/MS: m/z=500[(M+1) ⁺ ]

Synthesis example 16: Synthesis of compound 394

(One) production example 1: Synthesis of intermediate 394-1

Intermediate 377-1 (10.0 g, 0.037 mol), 1,4-Phenylenediboronic acid (7.3 g, 0.044 mol), K ₂ CO ₃ (15.2 g, 0.110 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0007 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.1 g (yield 61.7%) of <Intermediate 394-1>.

(2) production example 2: Synthesis of compound 394

Intermediate 394-1 (10.0 g, 0.032 mol), Intermediate 293-3 (17.6 g, 0.038 mol), K ₂ CO ₃ (13.2 g, 0.096 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) to Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.7 g (yield 71.0%) of <Compound 394>.

LC/MS: m/z=692[(M+1) ⁺ ]

Synthesis example 17: Synthesis of compound 413

(One) production example 1: Synthesis of intermediate 413-1

Add DMF to 4-Bromo-1-naphthaldehyde (10.0 g, 0.043 mol), 4-Cyanobenzamidine hydrochloride (15.5 g, 0.085 mol), K ₂ CO ₃ (11.8 g, 0.085 mol), and stir at reflux at 120 ° C for 18 hours. and reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.7 g (yield 66.0%) of <Intermediate 413-1>.

(2) production example 2: Synthesis of compound 413

Intermediate 377-2 (10.0 g, 0.031 mol), Intermediate 413-1 (18.4 g, 0.038 mol), K ₂ CO ₃ (13.0 g, 0.094 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 70.7%) of <Compound 413>.

LC/MS: m/z=600[(M+1) ⁺ ]

Synthesis example 18: Synthesis of compound 433

(One) production example 1: Synthesis of intermediate 433-1

4,6-Dibromodibenzofuran (10.0 g, 0.024 mol), 4-Biphenylboronic acid (18.0 g, 0.037 mol), K ₂ CO ₃ (12.7 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL was added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction, concentration, and column were performed to obtain 9.8 g (yield 53.2%) of <Intermediate 433-1>.

(2) production example 2: Synthesis of intermediate 433-2

Intermediate 433-1 (10.0 g, 0.025 mol), 1,4-Phenylenediboronic acid (5.0 g, 0.030 mol), K ₂ CO ₃ (10.4 g, 0.075 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 7.2 g (yield 65.3%) of <Intermediate 433-2>.

(3) production example 3: Synthesis of intermediate 433-3

2-(4-Biphenylyl)-4,6-dichloro-1,3,5-triazine (10.0 g, 0.033 mol), 4-Cyanophenylboronic acid (5.8 g, 0.040 mol), K ₂ CO ₃ (13.7 g, 0.099) mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added with 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100° C. for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 5.8 g (yield 47.5%) of <Intermediate 433-3>.

(4) production example 4: Synthesis of compound 433

To intermediate 433-2 (10.0 g, 0.023 mol), intermediate 433-3 (10.0 g, 0.027 mol), K ₂ CO ₃ (9.4 g, 0.068 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.3 g (yield 74.3%) of <Compound 433>.

LC/MS: m/z=728[(M+1) ⁺ ]

Synthesis example 19: Synthesis of compound 457

(One) production example 1: Synthesis of intermediate 457-1

DMF was added to 4-Bromobenzenealdehyde (10.0 g, 0.054 mol), 4-Phenylbenzamidine hydrochloride (25.2 g, 0.108 mol), K ₂ CO ₃ (14.9 g, 0.108 mol), and the reaction was stirred at 120 ° C. under reflux for 18 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 18.7 g (yield 64.0%) of <Intermediate 457-1>.

(2) production example 2: Synthesis of intermediate 457-2

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 4'-Cyanobiphenyl-4-ylboronic acid (8.2 g, 0.037 mol), K ₂ CO ₃ (12.7 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.3 g (yield 48.4%) of <Intermediate 457-2>.

(3) production example 3: Synthesis of intermediate 457-3

Intermediate 457-2 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.2 g, 0.028 mol), KOAc (4.6 g, 0.047 mol), Pd(dppf)Cl ₂ (0.5 g, 0.001 mol) in Dioxane 200 mL was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.7 g (yield 69.3%) of <Intermediate 457-3>.

(4) production example 4: Synthesis of compound 457

Intermediate 457-3 (10.0 g, 0.022 mol), Intermediate 457-1 (10.8 g, 0.026 mol), K ₂ CO ₃ (8.9 g, 0.065 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.1 g (yield 75.7%) of <Compound 457>.

LC/MS: m/z=804 [(M+1) ⁺ ]

Synthesis example 20: Synthesis of compound 491

(One) production example 1: Synthesis of intermediate 491-1

Cyanuric chloride (10.0 g, 0.054 mol), (4-(Benzo[d]oxazol-2-yl)phenyl)boronic acid (31.1 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd ( Toluene 200 mL, Ethanol 50 mL, and H ₂ O 50 mL were added to PPh ₃ ) ₄ (1.3 g, 0.001 mol), and the reaction was stirred at 100° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 17.2 g (yield: 63.2%) of <Intermediate 491-1>.

(2) production example 2: Synthesis of compound 491

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 491-1 (20.9 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 15.8 g (yield 62.0%) of <Compound 491> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=734 [(M+1) ⁺ ]

Synthesis example 21: Synthesis of compound 524

(One) production example 1: Synthesis of intermediate 524-1

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 1,3-Benzoxazole-6-carbonitrile (6.6 g, 0.046 mol), Pd(OAc) ₂ (0.07 g, 0.0003 mol), Cu(OAc) ₂ (0.1 g, 0.0006 mmol), K ₂ CO ₃ (8.5 g, 0.061 mol), PPh ₃ (4.0 g, 0.015 mol) was added to Toluene, and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 5.8 g (yield 48.6%) of <Intermediate 524-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 524-2

Intermediate 524-1 (10.0 g, 0.026 mol), Bis(pinacolato)diboron (7.8 g, 0.031 mol), KOAc (5.0 g, 0.051 mol), Pd(dppf)Cl ₂ (0.6 g, 0.001 mol) in dioxane 200 mL was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.1 g (yield 72.3%) of <Intermediate 542-2>.

(3) production example 3: Synthesis of compound 524

To intermediate 524-2 (10.0 g, 0.023 mol), intermediate 491-1 (13.8 g, 0.028 mol), K ₂ CO ₃ (9.5 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0005 mol) Toluene 200 mL, Ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 74.8%) of <Compound 524>.

LC/MS: m/z=775[(M+1) ⁺ ]

Device Example (ETL)

In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm in size using an ITO glass substrate to which an ITO transparent electrode is attached, on a glass substrate of 25 mm × 25 mm × 0.7 mm After that, it was washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 ^-6 torr or more, the organic material and the metal were deposited on the ITO in the following structure.

Device Examples 1 to 105

The compound implemented according to the present invention was used as an electron transport layer, and an organic light emitting device having the following device structure was manufactured, and light emitting characteristics including current efficiency were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was used to deposit 5 nm, and then the hole transport layer was deposited at 100 nm using α-NPB. The electron blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, [BH1] was used as a host compound for the light emitting layer, and [BD1] was used as a dopant compound to be co-deposited to a thickness of 20 nm. The electron transport layer was formed to a thickness of 30 nm (Liq doping) using the compound of the formula shown in Table 1 below according to the present invention. An organic light emitting device was manufactured by forming a film of 1 nm of LiF and 100 nm of Al.

Device Comparative Example 1

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that the following [ET 1] was used instead of the compound according to the present invention for the electron transport layer in the device structures of Examples 1 to 105.

Device Comparative Example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner except that the following [ET 2] was used instead of the compound according to the present invention for the electron transport layer in the device structure of Examples 1 to 105.

Device Comparative Example 3

The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner except that the following [ET 3] was used instead of the compound according to the present invention for the electron transport layer in the device structure of Examples 1 to 105.

Experimental Example 1: Light emitting characteristics of Device Examples 1 to 105

For the organic light emitting device manufactured according to the above example, voltage, current and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1000 nit is shown in [Table 1] below.

Example electron transport layer V cd/A CIEx CIEy One Formula 1 4.1 8.1 0.139 0.146 2 Formula 12 3.7 8.2 0.139 0.146 3 Formula 13 4.1 8.3 0.139 0.145 4 Formula 15 4.1 8.3 0.139 0.148 5 Formula 16 4.0 7.7 0.140 0.144 6 Formula 17 4.2 8.4 0.138 0.146 7 Formula 19 4.0 8.5 0.138 0.148 8 Formula 20 4.1 8.1 0.139 0.148 9 Formula 30 3.9 8.1 0.136 0.148 10 Formula 36 4.1 8.1 0.139 0.147 11 Formula 37 3.9 8.1 0.141 0.148 12 Formula 38 4.1 7.9 0.137 0.150 13 Formula 39 4.3 8.0 0.137 0.149 14 Formula 40 3.9 8.3 0.138 0.148 15 Formula 41 3.9 8.1 0.140 0.151 16 Formula 50 3.8 8.2 0.140 0.154 17 Formula 53 3.8 8.1 0.137 0.152 18 Formula 54 4.0 7.8 0.139 0.145 19 Formula 55 4.4 7.8 0.138 0.154 20 chemical formula 57 4.2 8.3 0.139 0.152 21 Formula 58 4.1 8.1 0.138 0.148 22 Formula 59 3.9 8.3 0.138 0.148 23 Formula 60 3.8 8.1 0.139 0.145 24 Formula 66 4.1 8.3 0.138 0.143 25 Formula 68 4.0 7.9 0.139 0.145 26 Formula 69 3.9 8.3 0.138 0.147 27 Formula 72 3.9 8.0 0.138 0.144 28 Formula 74 4.0 8.1 0.138 0.148 29 Formula 75 4.2 8.3 0.137 0.150 30 Formula 76 4.3 8.1 0.138 0.148 31 Formula 78 4.1 8.3 0.139 0.145 32 Formula 84 3.9 8.1 0.136 0.145 33 Formula 85 4.1 8.4 0.139 0.143 34 Formula 86 4.0 7.7 0.140 0.154 35 Formula 87 4.0 8.3 0.138 0.148 36 Formula 88 4.0 8.0 0.137 0.150 37 Formula 89 3.9 8.3 0.139 0.145 38 Formula 90 3.8 8.1 0.137 0.149 39 Formula 91 3.8 8.2 0.137 0.150 40 Formula 92 4.0 8.1 0.138 0.145 41 Formula 93 4.0 8.1 0.139 0.147 42 Formula 98 3.9 8.1 0.136 0.148 43 Formula 102 3.8 8.1 0.139 0.146 44 Formula 106 4.1 8.0 0.139 0.149 45 Formula 107 3.9 8.2 0.141 0.145 46 Formula 110 4.3 8.3 0.136 0.150 47 Formula 111 4.1 8.1 0.14 0.151 48 Formula 113 3.9 7.8 0.132 0.155 49 Formula 115 3.9 7.9 0.132 0.154 50 Formula 118 3.7 8.2 0.133 0.153 51 Formula 119 3.9 8.0 0.135 0.156 52 Formula 126 3.6 8.1 0.135 0.159 53 Formula 128 3.6 8.0 0.132 0.157 54 Formula 133 3.8 7.7 0.134 0.150 55 Formula 134 3.7 8.0 0.135 0.156 56 Formula 135 3.6 8.1 0.135 0.159 57 Formula 143 3.9 8.2 0.133 0.148 58 Formula 146 3.8 7.8 0.134 0.150 59 Formula 155 3.7 8.2 0.133 0.152 60 Formula 157 3.7 7.9 0.133 0.149 61 Formula 167 4.0 8.0 0.133 0.153 62 Formula 173 3.8 8.2 0.132 0.155 63 Formula 176 3.9 8.2 0.133 0.153 64 Formula 184 3.9 8.2 0.134 0.150 65 Formula 191 3.7 8.0 0.131 0.150 66 Formula 201 3.9 8.3 0.134 0.148 67 Formula 206 3.7 7.4 0.131 0.153 68 Formula 212 3.6 7.9 0.134 0.151 69 Formula 224 3.9 8.1 0.134 0.154 70 Formula 227 3.7 7.7 0.136 0.150 71 Formula 232 4.3 8.2 0.131 0.155 72 Formula 233 3.7 8.0 0.135 0.156 73 Formula 234 3.5 8.1 0.134 0.151 74 Formula 240 3.9 8.2 0.134 0.150 75 Formula 258 4.2 8.2 0.134 0.153 76 Formula 291 3.8 7.6 0.135 0.149 77 Formula 292 4.0 8.3 0.133 0.151 78 Formula 293 3.8 8.4 0.133 0.153 79 Formula 294 3.6 8.0 0.134 0.151 80 Formula 295 3.9 7.9 0.134 0.154 81 Formula 296 3.7 8.1 0.136 0.150 82 Formula 303 3.7 8.1 0.139 0.145 83 Formula 311 3.5 7.9 0.136 0.145 84 Formula 313 3.7 8.2 0.139 0.143 85 Formula 319 3.5 7.3 0.136 0.148 86 Formula 347 3.4 7.8 0.139 0.146 87 Formula 349 3.7 8.0 0.139 0.149 88 Formula 359 4.4 8.1 0.139 0.148 89 Formula 363 3.7 7.9 0.133 0.152 90 Formula 377 3.5 7.3 0.136 0.148 91 Formula 391 3.9 7.9 0.134 0.154 92 Formula 394 4.1 8.2 0.136 0.153 93 Formula 395 3.6 7.9 0.138 0.151 94 Formula 413 3.7 8.4 0.133 0.152 95 Formula 425 4.4 8.2 0.130 0.155 96 Formula 433 3.9 7.8 0.135 0.149 97 Formula 437 4.0 8.1 0.142 0.151 98 Formula 457 4.2 8.1 0.139 0.147 99 Formula 463 3.9 8.2 0.140 0.152 100 Formula 479 3.8 8.2 0.133 0.153 101 Formula 491 3.6 8.0 0.132 0.149 102 Formula 502 3.9 7.8 0.131 0.150 103 Formula 508 3.7 8.0 0.135 0.156 104 Formula 524 3.6 8.3 0.133 0.157 105 Formula 526 4.0 7.9 0.137 0.143 Comparative Example 1 ET 1 4.7 6.6 0.135 0.151 Comparative Example 2 ET 2 4.8 6.2 0.136 0.155 Comparative Example 3 ET 3 5.0 6.0 0.131 0.159

Looking at the results shown in [Table 1], in the case of a device employing the compound according to the present invention as an electron transport layer in an organic light emitting device, a device employing a conventional compound in contrast to the characteristic structure of the compound according to the present invention (comparison) As compared to Examples 1 to 3), it can be seen that the driving voltage is reduced and the current efficiency is improved.

[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]

[ET 1] [ET 2] [ET 3]

Claims (7)

An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]

In the [Formula I],
X _One To X ₃ Are the same as or different from each other, each independently represent N or CH, wherein at least one of X _One To X ₃ is N,
Y is CR ₁ R ₂ , NR ₃ , O or S;
wherein R ₁ to R ₃ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted Any one selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
The R ₁ and R ₂ may be combined with each other to form an alicyclic ring or an aromatic ring,
A is represented by the following [Structural Formula 1], B is represented by the following [Structural Formula 2], C is represented by the following [Structural Formula 3],
[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

In the [Structural Formula 1] to [Structural Formula 3],
L and L ₁ to L ₃ are the same or different from each other, and each independently is a single bond, or a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, substituted Or any one selected from an unsubstituted benzoxazolylene group and a substituted or unsubstituted benzothiazolylene group,
p is an integer from 0 to 2, and when p is 2, a plurality of L's are the same or different from each other,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, cycloalkyl or heterocycloalkyl. A substituted or unsubstituted substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms in which one or more cycloalkyl or heterocycloalkyl is fused, a substituted or unsubstituted any one selected from a fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole, and a substituted or unsubstituted benzothiazole,
Ar ₃ is a direct bond, or is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzoxazole, and a substituted or unsubstituted benzothiazole which one,
CN means a cyano group,
n and m are each an integer from 0 to 2, and o is an integer from 0 to 1, provided that n+m+o≧1. According to claim 1,
The substituted or unsubstituted means that R ₁ to R ₃ , L, L ₁ to L ₃ and Ar ₁ to Ar ₃ are deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, halogenated alkyl group, alkoxy group, It is substituted with one or more substituents selected from a halogenated alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, and a silyl group, or is substituted with a substituent to which two or more of the substituents are linked, or does not have any substituents Organic light emitting compound which means not. According to claim 1,
The [Formula I] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 534]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device, characterized in that it comprises at least one organic light emitting compound implemented by [Formula I] according to claim 1. 5. The method of claim 4,
The organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the electron transport layer. 6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the hole blocking layer.