KR102328684B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

Novel compound and organic light emitting device using the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

Any one of Q is CR, R is a substituent represented by the following formula (2), any one of the other is CR', R' is a substituent represented by the following formula (3), the remainder is CH,

However, the substituent represented by the following formula (2) and the substituent represented by the following formula (3) are connected by an ortho position,

n is an integer from 0 to 4,

R ₁ is hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _2-60 alkynyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; _{or C 5-60} heteroaryl comprising at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,

[Formula 2]

In Formula 2,

each X is independently N or CH, provided that at least one of them is N,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 5-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

[Formula 3]

In Formula 3,

Y is O or S.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above.

The compound represented by Chemical Formula 1 described above may be used as a material for the organic material layer of the organic light emitting device, and may improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device. In particular, the compound represented by Formula 1 described above may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole blocking layer (7), light emitting layer (3), electron transport layer (8), electron injection layer (9) and an example of an organic light emitting device including a cathode 4 .

Hereinafter, it will be described in more detail to help the understanding of the present invention.

The present invention provides a compound represented by the above formula (1).

, 또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

, or

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group including one or more, or substituted or unsubstituted with two or more substituents of the exemplified substituents connected. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. can be However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group 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, 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, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, as for heteroaryl among heteroarylamines, the description of the above-described heterocyclic group may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

Preferably, Chemical Formula 1 may be any one selected from compounds represented by the following Chemical Formulas 1-1 to 1-6:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,

Descriptions of X, Y, Ar ₁ , Ar ₂ , R ₁ and n are as defined above.

Preferably, n may be 0 or 1.

Preferably, R ₁ is hydrogen; heavy hydrogen; methyl; or phenyl.

Preferably, all X can be N.

Preferably, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

In the above formula,

m is an integer from 0 to 5,

k is an integer from 0 to 4,

R ₂ is hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _2-60 alkynyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; _{or C 5-60} heteroaryl including at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.

Preferably, R ₂ is hydrogen; heavy hydrogen; methyl; or phenyl.

For example, the compound represented by Formula 1 may be any one selected from the group consisting of the following.

On the other hand, the compound represented by Formula 1-1 may be prepared by a manufacturing method as shown in Scheme 1 below, and the compound represented by Formula 1-2 may be prepared by a manufacturing method as shown in Scheme 2 below, for example. and the compound represented by Chemical Formula 1-3 may be prepared by, for example, a preparation method as shown in Scheme 3 below, and the compound represented by Chemical Formula 1-4 may be prepared by, for example, a preparation method as shown in Scheme 4 below. And, the compound represented by Formula 1-5 may be prepared by, for example, a preparation method as shown in Scheme 5 below, and the compound represented by Formula 1-6 may be prepared by a preparation method as shown in Scheme 6 below, for example. have.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

[Scheme 6]

In Schemes 1 to 6, definitions other than Z are the same as defined above, and Z is halogen and more preferably bromo or chloro. The reaction is a Suzuki coupling reaction, and preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

In addition, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 It may include the indicated compound.

In addition, the organic layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.

In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1 above.

In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons may include the compound represented by Formula 1 above.

In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Formula 1 above.

Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole blocking layer (7), light emitting layer (3), electron transport layer (8), electron injection layer (9) and an example of an organic light emitting device including a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

Specifically, the organic material layer may include an emission layer, and the emission layer may include two or more types of host materials.

In this case, the two or more kinds of host materials may include the compound represented by Formula 1 above.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. And, after forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

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

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

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect with respect to the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. A material capable of transporting holes from the anode or hole injection layer to the light emitting layer as a hole transport material. This 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-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is a substituted or unsubstituted derivative. It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The organic light emitting device 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 compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of compound sub 1

(1) Preparation of compound A-1

In a nitrogen atmosphere, 2-bromo-3-chloro-1,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (61.1 g, 442.7 mmol) were mixed with tetrahydrofuran (2000). ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound A-1 (74.4 g, yield 70%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound A-2

In a nitrogen atmosphere, A1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were placed in dimethylformamide (250 ml), potassium carbonate was added, and stirred and heated to 140 ° C. did. After the reaction for 4 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound A-2 (24.3 g, yield 53%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound A-3

A-2 (20 g, 90.9 mmol) and bis (pinacolato) diboron (46.2 g, 181.8 mmol) were added to dioxane (400 ml) in a nitrogen atmosphere, stirred and refluxed. Then, potassium acetate (26.2 g, 272.7 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (1.6 g, 2.7 mmol) and tricyclohexylphosphine (1.5 g, 5.5 mmol) were added. After reaction for 6 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (284 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound A-3 (23.3 g, yield 82%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 1

In a nitrogen atmosphere, A-3 (20 g, 64.1 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (17.1 g, 64.1 mmol) were added to tetrahydrofuran (400 ml). Stirred and refluxed. Thereafter, potassium carbonate (26.6 g, 192.2 mmol) was dissolved in water (27 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.2 g, 1.9 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (535 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 1 (18.4 g, yield 69%, MS: [M+H] ⁺ = 418.1).

Preparation Example 2: Preparation of compound sub 2

(1) Preparation of compound B-1

In a nitrogen atmosphere, 1-bromo-4-chloro-2,5-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (61.1 g, 442.7 mmol) were mixed with tetrahydrofuran (2000). ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound B-1 (56.3 g, yield 53%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound B-2

In a nitrogen atmosphere, B-1 (50 g, 208.3 mmol) and bis (pinacolato) diboron (55.6 g, 208.3 mmol) were put in dimethylformamide (250 ml), potassium carbonate was added, and stirred and 140 ° C. heated with After the reaction for 6 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound B-2 (30.2 g, yield 66%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound B-3

In a nitrogen atmosphere, B-2 (20 g, 71.9 mmol) and bis (pinacolato) diboron (36.6 g, 143.9 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (20.7 g, 215.8 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (1.2 g, 2.2 mmol) and tricyclohexylphosphine (1.2 g, 4.3 mmol) were added. After reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (225 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound B-3 (11.7 g, yield 52%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 2

In a nitrogen atmosphere, B-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (363 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 2 (9.8 g, yield 54%, MS: [M+H] ⁺ = 418.1).

Preparation Example 3: Preparation of compound sub 3

(1) Preparation of compound C-1

In a nitrogen atmosphere, 1-bromo-4-chloro-2,3-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (159.6 g, 442.7 mmol) were mixed with tetrahydrofuran (2000). ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound C-1 (60.6 g, yield 57%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound C-2

In a nitrogen atmosphere, C-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were put in dimethylformamide (250 ml), potassium carbonate was added, and stirred and 140 ° C. heated with After the reaction for 5 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound C-2 (26.6 g, yield 58%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound C-3

In a nitrogen atmosphere, C-2 (20 g, 50 mmol) and bis (pinacolato) diboron (25.4 g, 100 mmol) were added to dioxane (400 ml), stirred and refluxed. Thereafter, potassium acetate (14.4 g, 150 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.9 g, 1.5 mmol) and tricyclohexylphosphine (0.8 g, 3 mmol) were added. After reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to chloroform (156 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound C-3 (11.7 g, yield 75%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 3

In a nitrogen atmosphere, C-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (363 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 3 (10.5 g, yield 58%, MS: [M+H] ⁺ = 418.1).

Preparation Example 4: Preparation of compound sub 4

(1) Preparation of compound D-1

In a nitrogen atmosphere, 1-bromo-3-chloro-2,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (151.9 g, 442.7 mmol) were mixed with tetrahydrofuran (2000). ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound D-1 (80.8 g, yield 76%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound D-2

In a nitrogen atmosphere, D-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were put in dimethylformamide (250 ml), potassium carbonate was added, and stirred and 140 ° C. heated with After the reaction for 7 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound D-2 (28.4 g, yield 62%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound D-3

In a nitrogen atmosphere, D-2 (20 g, 40 mmol) and bis (pinacolato) diboron (20.3 g, 80 mmol) were added to dioxane (400 ml), and the mixture was stirred and refluxed. Then, potassium acetate (11.5 g, 120 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added. After the reaction for 4 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound D-3 (8.6 g, yield 69%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 4

In a nitrogen atmosphere, D-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (363 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 4 (9.6 g, yield 53%, MS: [M+H] ⁺ = 418.1).

Preparation Example 5: Preparation of compound sub 5

(1) Preparation of compound E-1

In a nitrogen atmosphere, 1-bromo-5-chloro-2,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (151.9 g, 442.7 mmol) were mixed with tetrahydrofuran (2000 ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound E-1 (85 g, yield 80%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound E-2

In a nitrogen atmosphere, E-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were put in dimethylformamide (250 ml), potassium carbonate was added, and stirred and 140 ° C. heated with After the reaction for 7 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound E-2 (29.8 g, yield 65%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound E-3

In a nitrogen atmosphere, E-2 (20 g, 33.3 mmol) and bis (pinacolato) diboron (16.9 g, 66.7 mmol) were added to dioxane (400 ml), stirred and refluxed. Thereafter, potassium acetate (9.6 g, 100 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.6 g, 1 mmol) and tricyclohexylphosphine (0.6 g, 2 mmol) were added. After reaction for 6 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (104 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound E-3 (8 g, yield 77%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 5

E-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were placed in tetrahydrofuran (400 ml) in a nitrogen atmosphere. Stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (363 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound sub 5 (10.9 g, yield 60%, MS: [M+H] ⁺ = 418.1).

Preparation Example 6: Preparation of compound sub 6

(1) Preparation of compound F-1

In a nitrogen atmosphere, 2-bromo-4-chloro-1,3-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl) boronic acid (151.9 g, 442.7 mmol) were mixed with tetrahydrofuran (2000 ml), stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (15.3 g, 13.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (2125 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound F-1 (62.7 g, yield 59%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound F-2

In a nitrogen atmosphere, F-1 (50 g, 208.3 mmol) and bis (pinacolato) diboron (55.6 g, 208.3 mmol) were put in dimethylformamide (250 ml), potassium carbonate was added, and stirred and 140 ° C. heated with After the reaction for 4 hours, after cooling to room temperature, water was added. The solid formed was then filtered off. This was again put in chloroform (458 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound F-2 (27.5 g, yield 60%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound F-3

In a nitrogen atmosphere, F-2 (20 g, 33.3 mmol) and bis(pinacolato)diboron (16.9 g, 66.7 mmol) were added to dioxane (400 ml), stirred and refluxed. Thereafter, potassium acetate (9.6 g, 100 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.6 g, 1 mmol) and tricyclohexylphosphine (0.6 g, 2 mmol) were added. After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (104 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound F-3 (7.8 g, yield 75%, MS: [M+H] ⁺ = 313.1).

(4) Preparation of compound sub 6

In a nitrogen atmosphere, F-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirred and refluxed. Thereafter, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (363 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound sub 6 (12.9 g, yield 71%, MS: [M+H] ⁺ = 418.1).

Preparation Example 7: Preparation of compound G-2

(1) Preparation of compound G-1

A-2 (50 g, 227.3 mmol) and int G (79.3 g, 227.3 mmol) were added to dimethylformamide (1000 ml) in a nitrogen atmosphere, stirred and refluxed. Thereafter, sodium tert-butoxide (144.7 g, 681.8 mmol) was added, and after sufficient stirring, bis(tertiary-butylphosphine)palladium (3.5 g, 6.8 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again added to chloroform (1248 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound G-1 (97.3 g, yield 78%, MS: [M+H] ⁺ = 550.1).

(2) Preparation of compound G-2

In a nitrogen atmosphere, G-1 (20 g, 36.4 mmol) and bis(pinacolato)diboron (18.5 g, 72.8 mmol) were added to dioxane (400 ml), stirred and refluxed. Thereafter, potassium acetate (10.5 g, 109.3 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol) were added. After the reaction for 4 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (234 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound G-2 (17.8 g, yield 76%, MS: [M+H] ⁺ = 642.2).

Preparation Example 8: Preparation of compound int A

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] furan-4-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1481 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int A (54.8 g, yield 74%, MS: [M+H] ⁺ = 334.1).

Preparation Example 9: Preparation of compound int B

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] furan-3-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1481 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int B (43.7 g, yield 59%, MS: [M+H] ⁺ = 334.1).

Preparation 10: Preparation of compound int C

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] furan-2-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1481 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int C (41.5 g, yield 56%, MS: [M+H] ⁺ = 334.1).

Preparation Example 11: Preparation of compound int D

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] furan-1-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1481 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int D (45.2 g, yield 61%, MS: [M+H] ⁺ = 334.1).

Preparation 12: Preparation of compound int E

2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere added, stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (1552 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int E (52 g, yield 67%, MS: [M+H] ⁺ = 350.1).

Preparation 13: Preparation of compound int F

1-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere added, stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (1552 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int F (50.4 g, yield 65%, MS: [M+H] ⁺ = 350.1).

Preparation 14: Preparation of compound int G

3-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere added, stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (1552 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int G (39.6 g, yield 51%, MS: [M+H] ⁺ = 350.1).

Preparation 15: Preparation of compound int H

4-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere added, stirred and refluxed. Thereafter, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.7 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (1552 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound int H (42.7 g, yield 55%, MS: [M+H] ⁺ = 350.1).

Example 1: Synthesis of compound 1

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int A (8 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 4 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (175 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 1 (11.6 g, yield 66%, MS: [M+H] ⁺ = 731.2).

Example 2: Synthesis of compound 2

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int B (8 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 4 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (175 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 2 (13.1 g, yield 75%, MS: [M+H] ⁺ = 731.2).

Example 3: Synthesis of compound 3

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int C (8 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 5 hours, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (175 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 3 (13.8 g, yield 79%, MS: [M+H] ⁺ = 731.2).

Example 4: Synthesis of compound 4

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int D (8 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 3 hours, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again put in chloroform (175 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 4 (13.5 g, yield 77%, MS: [M+H] ⁺ = 731.2).

Example 5: Synthesis of compound 5

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int E (8.4 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 3 hours, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 5 (10.9 g, yield 61%, MS: [M+H] ⁺ = 747.2).

Example 6: Synthesis of compound 6

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int F (8.4 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 5 hours, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 6 (10.9 g, yield 61%, MS: [M+H] ⁺ = 747.2).

Example 7: Synthesis of compound 7

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 7 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 7 (9.3 g, yield 52%, MS: [M+H] ⁺ = 747.2).

Example 8: Synthesis of compound 8

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int H (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), and the mixture was stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 4 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 8 (12.7 g, yield 71%, MS: [M+H] ⁺ = 747.2).

Example 9: Synthesis of compound 9

In a nitrogen atmosphere, sub 2 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 4 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 9 (12.3 g, yield 69%, MS: [M+H] ⁺ = 747.2).

Example 10: Synthesis of compound 10

In a nitrogen atmosphere, sub 3 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were placed in dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 5 hours, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 10 (10.2 g, yield 57%, MS: [M+H] ⁺ = 747.2).

Example 11: Synthesis of compound 11

In a nitrogen atmosphere, sub 4 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, and after sufficiently stirring, the reaction was cooled to room temperature for 3 hours, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 11 (13.1 g, yield 73%, MS: [M+H] ⁺ = 747.2).

Example 12: Synthesis of compound 12

In a nitrogen atmosphere, sub 5 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Then, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 7 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 12 (11.6 g, yield 65%, MS: [M+H] ⁺ = 747.2).

Example 13: Synthesis of compound 13

In a nitrogen atmosphere, sub 6 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Thereafter, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after reaction for 4 hours, cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was again put in chloroform (179 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 13 (12.3 g, yield 69%, MS: [M+H] ⁺ = 747.2).

Example 14: Synthesis of compound 14

G-2 (50 g, 78 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (26.8) in nitrogen atmosphere g, 78 mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1282 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 14 (50 g, yield 78%, MS: [M+H] ⁺ = 823.3).

Example 15: Synthesis of compound 15

G-2 (50 g, 78 mmol) and 2-chloro-4- (naphthalen-2-yl)-6-phenyl-1,3,5-triazine (24.7 g, 78 mmol) were reacted with tetrahydrogen It was added to furan (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1242 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 15 (34.8 g, yield 56%, MS: [M+H] ⁺ = 797.2).

Example 16: Synthesis of compound 16

G-2 (50 g, 78 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) -6-phenyl-1,3,5-triazine (30.7 g, 78) in nitrogen atmosphere mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1360 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 16 (45.6 g, yield 67%, MS: [M+H] ⁺ = 873.3).

Example 17: Synthesis of compound 17

G-2 (50 g, 78 mmol) and 2-chloro-4- (dibenzo [b,d] furan-4-yl) -6-phenyl-1,3,5-triazine (27.8 g) in a nitrogen atmosphere , 78 mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to chloroform (1304 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 17 (35.2 g, yield 54%, MS: [M+H] ⁺ = 837.2).

Example 18: Synthesis of compound 18

G-2 (50 g, 78 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine (29.1 g, 78 mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1329 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 18 (44.5 g, yield 67%, MS: [M+H] ⁺ = 853.2).

Example 19: Synthesis of compound 19

G-2 (50 g, 78 mmol) and 9- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) -9H-carbazole (27.8 g, 78 mmol) in nitrogen atmosphere was put in tetrahydrofuran (1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1303 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 19 (41 g, yield 63%, MS: [M+H] ⁺ = 836.2).

Example 20: Synthesis of compound 20

In a nitrogen atmosphere, G-2 (50 g, 78 mmol) and 2-chloro-4-phenyl-6- (phenyl-d5) -1,3,5-triazine (21.2 g, 78 mmol) were mixed with tetrahydrofuran ( 1000 ml), stirred and refluxed. Thereafter, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.7 g, 2.3 mmol) was added. After the reaction for 2 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in chloroform (1172 ml) to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound 20 (42.8 g, yield 73%, MS: [M+H] ⁺ = 752.2).

[Experimental example]

Experimental Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HI-1 compound to a thickness of 50 Å on the ITO transparent electrode prepared as described above. On the hole injection layer, the following HT-1 compound was thermally vacuum deposited to a thickness of 250 Å to form a hole transport layer, and the following HT-2 compound was vacuum deposited to a thickness of 50 Å on the HT-1 deposited film to form an electron blocking layer. . Compound 1 prepared in Example 1 above, the following YGH-1 compound, and phosphorescent dopant YGD-1 as a light emitting layer on the HT-2 deposited film were co-deposited in a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 Å. . The following ET-1 compound was vacuum deposited to a thickness of 250 Å on the light emitting layer to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited at a weight ratio of 98:2 on the electron transport layer to inject an electron having a thickness of 100 Å layer was formed. A cathode was formed by depositing aluminum to a thickness of 1000 Å on the electron injection layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 ~ 5 × 10 ^-8 torr did.

Experimental Examples 2 to 20 and Comparative Experimental Examples 1 to 2

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1 in Experimental Example 1. The compounds of CE1 and CE2 in Table 1 below are as follows.

In the Experimental Examples and Comparative Experimental Examples, voltage and efficiency were measured ^{for the organic light emitting device at a current density of 10 mA/cm 2 , and lifetimes were measured at a current density of 50 mA/cm 2} The results are shown in Table 1 below. . At this time, LT ₉₅ means the time at which 95% of the initial luminance is obtained.

light emitting layer voltage (V,
@10 mA/cm ² ) Efficiency (Cd/A, @10 mA/cm ² ) color coordinates
(x,y) Lifetime (hr, LT ₉₅ at 50 mA/cm ² ) Experimental Example 1 compound 1 4.0 78 0.46, 0.54 200 Experimental Example 2 compound 2 4.1 79 0.46, 0.54 210 Experimental Example 3 compound 3 4.2 80 0.46, 0.54 195 Experimental Example 4 compound 4 4.1 80 0.46, 0.54 215 Experimental Example 5 compound 5 4.1 81 0.46, 0.53 275 Experimental Example 6 compound 6 4.1 80 0.46, 0.54 210 Experimental Example 7 compound 7 4.1 80 0.46, 0.54 280 Experimental Example 8 compound 8 4.1 80 0.46, 0.54 244 Experimental Example 9 compound 9 4.0 83 0.46, 0.54 220 Experimental Example 10 compound 10 4.0 81 0.46, 0.54 215 Experimental Example 11 compound 11 4.1 83 0.46, 0.54 230 Experimental Example 12 compound 12 4.0 85 0.46, 0.54 244 Experimental Example 13 compound 13 4.1 84 0.46, 0.54 199 Experimental Example 14 compound 14 4.1 82 0.46, 0.54 185 Experimental Example 15 compound 15 4.2 83 0.46, 0.53 266 Experimental Example 16 compound 16 4.2 81 0.46, 0.54 275 Experimental Example 17 compound 17 4.2 83 0.46, 0.54 246 Experimental Example 18 compound 18 4.2 83 0.46, 0.54 251 Experimental Example 19 compound 19 4.4 81 0.46, 0.54 305 Experimental Example 20 compound 20 4.1 80 0.46, 0.54 320 Comparative Experimental Example 1 CE1 4.0 74 0.46, 0.54 110 Comparative Experimental Example 2 CE2 4.2 72 0.46, 0.55 90

As shown in Table 1, when the compound of the present invention was used as a material for the light emitting layer, it was confirmed that the efficiency and lifespan were superior to those of Comparative Experimental Examples. It seems that electrical stability is increased as a triazine-based substituent and a carbazole-based substituent are connected to the dibenzofuran at an ortho position, and a dibenzofuranyl group or a dibenzothiophenyl group is substituted for the carbazole-based substituent.

1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron transport layer
9: electron injection layer

Claims (11)

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

In Formula 1,
Any one of Q is CR, R is a substituent represented by the following formula (2), any one of the other is CR', R' is a substituent represented by the following formula (3), and the remainder is CH,
However, the substituent represented by the following formula (2) and the substituent represented by the following formula (3) are connected by an ortho position,
n is an integer from 0 to 4,
R ₁ is hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _2-60 alkynyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; _{or C 5-60} heteroaryl comprising at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,
[Formula 2]

In Formula 2,
each X is independently N or CH, provided that at least one of them is N;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 5-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
[Formula 3]

In Formula 3,
Y is O or S.
According to claim 1,
Formula 1 is a compound represented by the following Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,
Descriptions of X, Y, Ar ₁ , Ar ₂ , R ₁ and n are as defined in claim 1 .
According to claim 1,
n is 0 or 1.
According to claim 1,
R ₁ is hydrogen; heavy hydrogen; methyl; or phenyl.
According to claim 1,
X is all N;
According to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

In the above formula,
m is an integer from 0 to 5,
k is an integer from 0 to 4,
R ₂ is hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _2-60 alkynyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; _{or C 5-60} heteroaryl including at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.
7. The method of claim 6,
R ₂ is hydrogen; heavy hydrogen; methyl; or phenyl.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 8 which is an organic light emitting device.
10. The method of claim 9,
The organic material layer may include an emission layer, wherein the emission layer includes two or more host materials.
11. The method of claim 10,
The at least two host materials include the compound represented by Formula 1, an organic light emitting device.

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