KR102462985B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel hetero-cyclic compound and organic light emitting device using same

The present invention relates to a novel heterocyclic 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 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. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, 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 It lights up when it falls back to the ground state.

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 heterocyclic 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,

X ₁ To X ₃ are each independently N or CR ₆ However, at least one is N,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted aryl having 6 to 60 carbon atoms; Or a substituted or unsubstituted O, N, Si, and S is a heteroaryl having 2 to 60 carbon atoms including at least one,

R ₁ to R ₆ are each independently hydrogen; heavy hydrogen; halogen; hydroxy; nitrile; nitro; amino; substituted or unsubstituted C 2 to C 60 alkyl; substituted or unsubstituted alkoxy having 2 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted C 6 to C 60 aryl; Or a substituted or unsubstituted O, N, Si and S, including at least one of C 2 to C 60 heteroaryl,

One of A, B, C and D is a substituent represented by the following formula 1-1, and the rest is hydrogen or deuterium;

[Formula 1-1]

In Formula 1-1,

R ₇ to R ₁₁ are each independently hydrogen; heavy hydrogen; halogen; hydroxy; nitrile; nitro; amino; substituted or unsubstituted C 2 to C 60 alkyl; substituted or unsubstituted alkoxy having 2 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted C 6 to C 60 aryl; A substituted or unsubstituted O, N, Si, and S heteroaryl containing at least one of 2 to 60 carbon atoms, or R ₇ to R ₁₀ are combined with adjacent groups to form a condensed ring,

n is an integer from 1 to 6.

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. do.

The compound represented by Chemical Formula 1 described above may be used as a material for the organic 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 the above formula (1) may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.

FIG. 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), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light-emitting device including a cathode 4 are shown.

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).

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

and

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 containing one or more, or substituted or unsubstituted, in which two or more substituents of the above-exemplified substituents are 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 of the carbonyl group is not particularly limited, but it is preferably from 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 a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

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, 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, phenanthroline group, isoxazolyl group, thiadia and a jolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is 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, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the above-described alkenyl groups. 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-A, 1-B, 1-C and 1-D.

In the above formulas 1-A, 1-B, 1-C and 1-D,

Descriptions of X ₁ , X ₂ , X ₃ , Ar ₁ , Ar ₂ , and R ₇ to R ₁₀ are as defined above.

Preferably, X ₁ to X ₃ are all N.

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

Preferably, Formula 1-1 may be any one selected from the group consisting of the following compounds.

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

Meanwhile, the compound represented by Chemical Formula 1 may be prepared by a preparation method as shown in Scheme 1 below.

[Scheme 1]

In Scheme 1, definitions other than X are the same as defined above, and X is halogen and more preferably bromo or chloro. The reaction is a Suzuki coupling reaction, and preferably carried out 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 the formula (1). 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, an electron blocking layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, the electron blocking layer or the hole injection and transport at the same time The layer includes a compound represented by Formula 1 above.

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

Specifically, the emission layer may include a host material.

In this case, the host material may include a compound represented by Formula 1 above.

In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or the layer that simultaneously injects and transports electrons is represented by Formula 1 compounds.

In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons includes 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.

In addition, 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 diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

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

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 material 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 as 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to the above 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 multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection material is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is generated in the light emitting layer A compound that prevents the excitons from moving to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that 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, polyaniline and polythiophene-based conductive polymers, and the like, 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. A material with high hole mobility. 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 heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., 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. As the styrylamine compound, a substituted or unsubstituted 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 an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport material is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. This is suitable. 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.

Hereinafter, preferred embodiments are presented to help the understanding of the invention. However, the following examples are only for illustrating the present invention, and the present invention is not limited thereto.

Preparation Example 1: Preparation of Compound A

(1) Preparation of compound A-1

Naphthalen-2-amine (naphthalen-2-amine, 200.0 g, 1.0 eq), 1-bromo-2-iodobenzene (1-bromo-2-iodobenzene, 395.1 g, 1.0 eq), sodium tert-butoxide (NaOt-Bu, 268.4 g, 2 eq), palladium acetate (Pd(OAc) ₂ , 3.13 g, 0.01 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4,5 -Bis(diphenylphosphino)-9,9-dimethylxanthene, Xantphos, 16.1 g, 0.02 eq) and toluene (Toluene, 2 L) were dissolved under reflux and stirred at 60 °C. After 2 hours, when the reaction was completed, silica was filtered to remove sodium tert-butoxide, and then the solvent was removed by distillation under reduced pressure. It was dissolved using chloroform, washed with water, added with magnesium sulfate and acid clay, stirred, filtered, and concentrated under reduced pressure. Thereafter, compound A-1 was obtained through column chromatography under the condition of ethyl acetate:hexane = 1:50. (316.5 g, yield 76%, MS: [M+H] ⁺ =299)

(2) Preparation of compound A (5H-benzo[b]carbazole)

Bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu ₃ P) ₂ , 5.42 g, 0.01 eq) in compound A-1 (316.5 g, 1.0 eq), potassium carbonate (K ₂ CO ₃ , 293.4 g, 2.00 eq) was added to diethylacetamide (Dimethylacetamide, DMAc, 3 L), refluxed and stirred. After 3 hours, the reaction product was poured into water to crystallize and filtered to obtain a solid. The filtered solid was completely dissolved in 1,2-dichlorobenzene (1 L) at 100 °C, washed with water, and magnesium sulfate and acid clay were added to the solution in which the product was dissolved, stirred and filtered. and concentrated under reduced pressure. After purification by column chromatography, compound A (5H-benzo[b]carbazole) was obtained. (131.4 g, yield 57%, MS: [M+H] ⁺ =218)

Preparation Example 2: Preparation of Compound B

Using 2-bromo-1-iodonaphthalene instead of 1-bromo-2-idobenzene, the following compound B (13H-dibenzo [ a,h]carbazole) was obtained.

Preparation Example 3: Preparation of compound C

Using 2,3-dibromonaphthalene instead of 1-bromo-2-idobenzene, the following compound C (6H-dibenzo[b,h] carbazole) was obtained.

Preparation Example 4: Preparation of compound D

Using 1-bromo-2-iodonaphthalene instead of 1-bromo-2-idobenzene, the following compound D (7H-dibenzo[ b, g] carbazole) was obtained.

Preparation Example 5: Preparation of compound E

(1) Preparation of compound E-3

1-bromonaphthalen-2-ol (1-bromonaphthalen-2-ol, 100.0 g, 1.0 eq), (3-chloro-2-fluorophenyl) boronic acid ((3-chloro-2-fluorophenyl) boronic acid , 93.8 g, 1.2 eq), calcium carbonate (K ₂ CO ₃ , 185.9 g, 3.0 eq), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ , Tetrakis(triphenylphosphine)palladium(0) ), 15.5 g, 0.03 eq) was dissolved in tetrahydrofuran (THF, 1 L) and water (300 ml) and heated and stirred at 80 °C. When the reaction was completed after 2 hours, the organic solvent layer was separated, magnesium sulfate and acid clay were added, stirred, filtered, and concentrated under reduced pressure. This was subjected to column chromatography to obtain compound E-3 (100.2 g, yield 82%, MS: [M+H] ⁺ =273)

(2) Preparation of compound E-2

Compound E-3 (100.2 g) and calcium carbonate (K ₂ CO ₃ , 152.6 g, 3 eq) were added to diethylacetamide (Dimethylacetamide, DMAc, 1 L), and the mixture was heated and stirred at 80 °C. When the reaction was completed after 1 hour, the reaction product was poured into water (2 L) to drop crystals and filtered to obtain a solid. The obtained solid was dissolved in toluene (1 L), washed with water, the organic solvent layer was separated, magnesium sulfate and acid clay were added, stirred, and then filtered. Ethyl acetate was poured, leaving only 20% of the filtered solvent, to drop crystals and filtered. Through this, compound E-2 was obtained. (68.8 g, yield 74%, MS: [M+H] ⁺ =253)

(3) Preparation of compound E-1

After dissolving compound E-2 (68.8 g) in chloroform (CHCl ₃ , 1 L), the temperature was lowered to 0 °C while stirring. N-bromosuccinimide (N-bromosuccinimide, 54.4 g, 1.1 eq) is slowly added. When the reaction was completed after 1 hour, it was washed with an aqueous solution of sodium sulfite (Na ₂ SO ₃ ), the organic solvent layer was separated, magnesium sulfate and acid clay were added, stirred, and then filtered. Ethyl acetate was poured, leaving only 20% of the filtered solvent, to drop crystals and filtered. Through this, compound E-1 was obtained. (57.2 g, yield 56%, MS: [M+H] ⁺ =332)

(4) Preparation of compound E

Compound E-1 (57.2 g, 1.0 eq), bis(pinacolato)diboron (Bis(pinacolato)diboron, 78.1 g, 1.2 eq), (1,1'-bis(diphenylphosphino)ferrocene)palladium dichloride (Pd(dppf)Cl ₂ , (1,1'-Bis(diphenylphosphino)ferrocene)palladium dichloride, 3.75 g, 0.02 eq) and potassium acetate (KOAc, potassium acetate, 50.3 g, 2.00 eq) were placed in 1,4-dioxane (1,4-Dioxnae, 600 ml) and heated and stirred at 100 °C. When the reaction was completed after 3 hours, the solvent was removed under reduced pressure. The filtered solid was completely dissolved in chloroform (CHCl ₃ ), washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to remove about 80% of the solvent. Ethanol was added thereto under reflux to drop crystals, cooled, and filtered to obtain compound E. (80.6 g, yield 83%, MS: [M+H] ⁺ =379)

Preparation Example 6: Preparation of compound F

The following compound F was obtained in the same manner as in the preparation of compound E using (4-chloro-2-fluorophenyl)boronic acid instead of (3-chloro-2-fluorophenyl)boronic acid. (MS: [M+H] ⁺ =379)

Preparation Example 7: Preparation of compound G

The following compound G was obtained in the same manner as in the preparation of compound E using (5-chloro-2-fluorophenyl)boronic acid instead of (3-chloro-2-fluorophenyl)boronic acid. (MS: [M+H] ⁺ =379)

Preparation 8: Preparation of compound H

The following compound H was synthesized in the same manner as in the preparation of compound E using (2-chloro-6-fluorophenyl)boronic acid instead of (3-chloro-2-fluorophenyl)boronic acid. MS: [M+H] ⁺ =379

Intermediate for preparing compounds 1 to 51 of Examples 1 to 51 below by reacting the compound prepared in Preparation Examples 5 to 8 and an intermediate containing triazine through a Suzuki coupling reaction Each was used as a compound.

Example 1: Preparation of compound 1

In a nitrogen atmosphere, compound sub1 (20 g, 41.3 mmol), compound A (9.9 g, 45.5 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (106 mg, 0.207 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again purified with chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1. (13.7 g, yield 50%, MS: [M+H] ⁺ =665)

Example 2: Preparation of compound 2

In a nitrogen atmosphere, compound sub2 (20 g, 41.3 mmol), compound A (9.8 g, 45.5 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (105 mg, 0.2 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2. (11.8 g yield 43%, MS: [M+H] ⁺ =665)

Example 3: Preparation of compound 3

In a nitrogen atmosphere, compound sub3 (20 g, 41.3 mmol), compound A (9.8 g, 45.5 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (105 mg, 0.2 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3. (14.5 g, yield 53%, MS: [M+H] ⁺ =665)

Example 4: Preparation of compound 4

In a nitrogen atmosphere, compound sub4 (20 g, 41.3 mmol), compound A (9.8 g, 45.5 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (105 mg, 0.2 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 4. (15.6 g, yield 57%, MS: [M+H] ⁺ =665)

Example 5: Preparation of compound 5

In a nitrogen atmosphere, compound sub5 (20 g, 37.5 mmol), compound A (9.0 g, 41.2 mmol) and sodium tert-butoxide (sodium tert-butoxide, 10.8 g, 112 mmol) were added to xylene (200 ml) and stirred and reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (96 mg, 0.187 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5. (14.7 g, yield 55%, MS: [M+H] ⁺ =715)

Example 6: Preparation of compound 6

In a nitrogen atmosphere, compound sub6 (20 g, 37.5 mmol), compound A (9.0 g, 41.2 mmol) and sodium tert-butoxide (sodium tert-butoxide, 10.8 g, 112 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (96 mg, 0.187 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6. (14.7 g, yield 55%, MS: [M+H] ⁺ =715)

Example 7: Preparation of compound 7

In a nitrogen atmosphere, compound sub7 (20 g, 34.2 mmol), compound A (8.2 g, 37.7 mmol) and sodium tert-butoxide (9.9 g, 102 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (87 mg, 0.171 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7. (15.5 g, yield 59%, MS: [M+H] ⁺ =765)

Example 8: Preparation of compound 8

In a nitrogen atmosphere, compound sub8 (20 g, 34.2 mmol), compound A (8.2 g, 37.7 mmol) and sodium tert-butoxide (9.9 g, 102 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (87 mg, 0.171 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8. (13.8 g, yield 53%, MS: [M+H] ⁺ =765)

Example 9: Preparation of compound 9

In a nitrogen atmosphere, compound sub9 (20 g, 35.7 mmol), compound A (8.5 g, 39.3 mmol) and sodium tert-butoxide (10.3 g, 107 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (91 mg, 0.179 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9. (12.9 g, yield 49%, MS: [M+H] ⁺ =741)

Example 10: Preparation of compound 10

In a nitrogen atmosphere, compound sub10 (20 g, 35.7 mmol), compound A (8.5 g, 39.3 mmol) and sodium tert-butoxide (sodium tert-butoxide, 10.3 g, 107 mmol) were added to it, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (91 mg, 0.179 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10. (14.8 g, yield 56%, MS: [M+H] ⁺ =741)

Example 11: Preparation of compound 11

In a nitrogen atmosphere, compound sub11 (20 g, 34.2 mmol), compound A (8.21 g, 37.7 mmol) and sodium tert-butoxide (9.9 g, 102 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (87 mg, 0.171 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11. (16.2 g, yield 62%, MS: [M+H] ⁺ =765)

Example 12: Preparation of compound 12

In a nitrogen atmosphere, compound sub12 (20 g, 31.5 mmol), compound A (7.5 g, 34.7 mmol) and sodium tert-butoxide (9.1 g, 94.6 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (81 mg, 0.158 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12. (15.6 g, yield 61%, MS: [M+H] ⁺ =815)

Example 13: Preparation of compound 13

In a nitrogen atmosphere, compound sub13 (20 g, 31.4 mmol), compound A (7.5 g, 34.6 mmol) and sodium tert-butoxide (9.1 g, 94.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (80 mg, 0.157 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13. (16.9 g, yield 66%, MS: [M+H] ⁺ =817)

Example 14: Preparation of compound 14

In a nitrogen atmosphere, compound sub14 (20 g, 29.2 mmol), compound A (7.0 g, 32.2 mmol) and sodium tert-butoxide (8.4 g, 87.7 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (75 mg, 0.146 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 14. (13.6 g, yield 54%, MS: [M+H] ⁺ =866)

Example 15: Preparation of compound 15

In a nitrogen atmosphere, compound sub15 (20 g, 31.4 mmol), compound A (7.5 g, 34.6 mmol) and sodium tert-butoxide (9.1 g, 94.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (80 mg, 0.157 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 15. (13.8 g, yield 54%, MS: [M+H] ⁺ =817)

Example 16: Preparation of compound 16

In a nitrogen atmosphere, compound sub16 (20 g, 30.8 mmol), compound A (7.4 g, 33.9 mmol) and sodium tert-butoxide (8.9 g, 92.4 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (79 mg, 0.154 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16. (14.0 g, yield 55%, MS: [M+H] ⁺ =830)

Example 17: Preparation of compound 17

In a nitrogen atmosphere, compound sub17 (20 g, 28.6 mmol), compound A (6.8 g, 31.5 mmol) and sodium tert-butoxide (8.2 g, 85.8 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (73 mg, 0.143 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 17. (13.8 g, yield 55%, MS: [M+H] ⁺ =881)

Example 18: Preparation of compound 18

In a nitrogen atmosphere, compound sub18 (20 g, 26.7 mmol), compound A (6.4 g, 29.4 mmol) and sodium tert-butoxide (7.7 g, 80.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (68 mg, 0.133 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 18. (15.8 g, yield 64%, MS: [M+H] ⁺ =931)

Example 19: Preparation of compound 19

In a nitrogen atmosphere, compound sub19 (20 g, 27.6 mmol), compound A (6.6 g, 30.3 mmol) and sodium tert-butoxide (8.0 g, 82.7 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (70 mg, 0.138 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 19. (12.5 g, yield 50%, MS: [M+H] ⁺ =907)

Example 20: Preparation of compound 20

In a nitrogen atmosphere, compound sub20 (20 g, 34.8 mmol), compound A (8.3 g, 38.3 mmol) and sodium tert-butoxide (10.0 g, 104 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (89 mg, 0.174 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 20. (15.0 g, yield 57%, MS: [M+H] ⁺ =755)

Example 21: Preparation of compound 21

In a nitrogen atmosphere, compound sub21 (20 g, 32.0 mmol), compound A (7.7 g, 35.3 mmol) and sodium tert-butoxide (9.2 g, 96.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (82 mg, 0.160 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21. (15.7 g, yield 61%, MS: [M+H] ⁺ =805)

Example 22: Preparation of compound 22

In a nitrogen atmosphere, compound sub22 (20 g, 29.7 mmol), compound A (7.1 g, 32.6 mmol) and sodium tert-butoxide (8.6 g, 89.0 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (76 mg, 0.148 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 22. (15.4 g, yield 61%, MS: [M+H] ⁺ =855)

Example 23: Preparation of compound 23

In a nitrogen atmosphere, compound sub23 (20 g, 30.8 mmol), compound A (7.4 g, 33.8 mmol) and sodium tert-butoxide (8.9 g, 92.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (79 mg, 0.154 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 23. (13.8 g, yield 54%, MS: [M+H] ⁺ =831)

Example 24: Preparation of compound 24

In a nitrogen atmosphere, compound sub24 (20 g, 33.9 mmol), compound A (8.1 g, 37.3 mmol) and sodium tert-butoxide (9.8 g, 101 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (87 mg, 0.169 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 24. (14.6 g, yield 56%, MS: [M+H] ⁺ =771)

Example 25: Preparation of compound 25

In a nitrogen atmosphere, compound sub25 (20 g, 30.0 mmol), compound A (7.2 g, 33.0 mmol) and sodium tert-butoxide (8.7 g, 90.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (77 mg, 0.150 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 25. (15.5 g, yield 61%, MS: [M+H] ⁺ =848)

Example 26: Preparation of compound 26

In a nitrogen atmosphere, compound sub26 (20 g, 27.1 mmol), compound A (6.5 g, 29.80 mmol) and sodium tert-butoxide (7.8 g, 81.2 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (69 mg, 0.135 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 26. (12.2 g, yield 49%, MS: [M+H] ⁺ =921)

Example 27: Preparation of compound 27

Compound sub27 (20 g, 26.5 mmol), compound A (6.3 g, 29.1 mmol) and odium tert-butoxide (7.6 g, 79.4 mmol) were added to xylene (200 ml) in a nitrogen atmosphere, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (68 mg, 0.132 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 27. (14.8 g, yield 60%, MS: [M+H] ⁺ =937)

Example 28: Preparation of compound 28

In a nitrogen atmosphere, compound sub28 (20 g, 30.1 mmol), compound A (7.2 g, 33.1 mmol) and sodium tert-butoxide (8.7 g, 90.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (77 mg, 0.151 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 28. (13.2 g, yield 52%, MS: [M+H] ⁺ =845)

Example 29: Preparation of compound 29

In a nitrogen atmosphere, compound sub29 (20 g, 28.7 mmol), compound A (6.9 g, 31.6 mmol) and sodium tert-butoxide (8.3 g, 86.2 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (73 mg, 0.144 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 29. (12.8 g, yield 51%, MS: [M+H] ⁺ =878)

Example 30: Preparation of compound 30

In a nitrogen atmosphere, compound sub1 (20 g, 41.3 mmol), compound B (12.6 g, 45.54 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (106 mg, 0.207 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 30. (16.2 g, yield 55%, MS: [M+H] ⁺ =715)

Example 31: Preparation of compound 31

In a nitrogen atmosphere, compound sub31 (20 g, 34.8 mmol), compound B (10.7 g, 38.3 mmol) and sodium tert-butoxide (10.0 g, 104 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (89 mg, 0.174 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 31. (15.7 g, yield 56%, MS: [M+H] ⁺ =805)

Example 32: Preparation of compound 32

In a nitrogen atmosphere, compound sub32 (20 g, 32.0 mmol), compound B (9.8 g, 35.3 mmol) and sodium tert-butoxide (9.2 g, 96.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (82 mg, 0.160 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 32. (13.1 g, yield 48%, MS: [M+H] ⁺ =855)

Example 33: Preparation of compound 33

In a nitrogen atmosphere, compound sub33 (20 g, 29.0 mmol), compound B (8.9 g, 31.9 mmol) and sodium tert-butoxide (8.4 g, 86.9 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (74 mg, 0.145 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 33. (13.3 g, yield 50%, MS: [M+H] ⁺ =922)

Example 34: Preparation of compound 34

In a nitrogen atmosphere, compound sub34 (20 g, 30.8 mmol), compound B (9.4 g, 33.8 mmol) and sodium tert-butoxide (8.9 g, 92.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (79 mg, 0.154 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 34. (15.4 g, yield 57%, MS: [M+H] ⁺ =882)

Example 35: Preparation of compound 35

In a nitrogen atmosphere, compound sub35 (20 g, 26.5 mmol), compound B (8.1 g, 29.1 mol) and sodium tert-butoxide (7.6 g, 79.4 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (68 mg, 0.132 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 35. (14.3 g, yield 55%, MS: [M+H] ⁺ =987)

Example 36: Preparation of compound 36

In a nitrogen atmosphere, compound sub36 (20 g, 24.6 mmol), compound B (7.5 g, 27.0 mmol) and sodium tert-butoxide (7.1 g, 73.7 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (63 mg, 0.123 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 36. (12.3 g, yield 48%, MS: [M+H] ⁺ =1046)

Example 37: Preparation of compound 37

In a nitrogen atmosphere, compound sub37 (20 g, 32.8 mmol), compound B (10.0 g, 36.1 mmol) and sodium tert-butoxide (9.5 g, 98.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (84 mg, 0.164 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 37. (12.9 g, yield 47%, MS: [M+H] ⁺ =841)

Example 38: Preparation of compound 38

In a nitrogen atmosphere, compound sub38 (20 g, 34.2 mmol), compound B (10.5 g, 37.7 mmol) and sodium tert-butoxide (9.9 g, 102 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (87 mg, 0.171 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 38. (13.9 g, yield 50%, MS: [M+H] ⁺ =815)

Example 39: Preparation of compound 39

In a nitrogen atmosphere, compound sub39 (20 g, 32.0 mmol), compound C (9.8 g, 35.3 mmol) and sodium tert-butoxide (9.2 g, 96.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (82 mg, 0.160 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 39. (16.4 g, yield 60%, MS: [M+H] ⁺ =855)

Example 40: Preparation of compound 40

In a nitrogen atmosphere, compound sub40 (20 g, 27.6 mmol), compound C (8.4 g, 30.3 mmol) and sodium tert-butoxide (8.0 g, 82.7 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (70 mg, 0.138 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 40. (16.6 g, yield 63%, MS: [M+H] ⁺ =957)

Example 41: Preparation of compound 41

In a nitrogen atmosphere, compound sub41 (20 g, 26.5 mmol), compound C (8.1 g, 29.1 mmol) and sodium tert-butoxide (7.6 g, 79.4 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (68 mg, 0.132 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 41. (14.3 g, yield 55%, MS: [M+H] ⁺ =987)

Example 42: Preparation of compound 42

In a nitrogen atmosphere, compound sub42 (20 g, 30.3 mmol), compound C (9.3 g, 33.3 mmol) and sodium tert-butoxide (8.7 g, 90.9 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (77 mg, 0.151 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 42. (15.1 g, yield 56%, MS: [M+H] ⁺ =892)

Example 43: Preparation of compound 43

In a nitrogen atmosphere, compound sub43 (20 g, 28.6 mmol), compound B (8.8 g, 31.5 mmol) and sodium tert-butoxide (8.2 g, 85.8 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (73 mg, 0.143 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 43. (14.1 g, yield 53%, MS: [M+H] ⁺ =931)

Example 44: Preparation of compound 44

In a nitrogen atmosphere, compound sub44 (20 g, 30.0 mmol), compound C (9.2 g, 33.0 mmol) and sodium tert-butoxide (8.7 g, 90.1 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (77 mg, 0.150 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 44. (13.2 g, yield 49%, MS: [M+H] ⁺ =898)

Example 45: Preparation of compound 45

In a nitrogen atmosphere, compound sub45 (20 g, 35.7 mmol), compound D (10.9 g, 39.3 mmol) and sodium tert-butoxide (10.3 g, 107 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (91 mg, 0.179 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 45. (16.4 g, yield 58%, MS: [M+H] ⁺ =791)

Example 46: Preparation of compound 46

In a nitrogen atmosphere, compound sub46 (20 g, 24.6 mmol), compound D (7.5 g, 27.0 mmol) and sodium tert-butoxide (7.1 g, 73.7 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (63 mg, 0.23 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 46. (16.9 g, yield 66%, MS: [M+H] ⁺ =1046)

Example 47: Preparation of compound 47

In a nitrogen atmosphere, compound sub47 (20 g, 30.8 mmol), compound D (9.4 g, 33.8 mmol) and sodium tert-butoxide (8.9 g, 92.3 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (79 mg, 0.154 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 47. (18.4 g, yield 68%, MS: [M+H] ⁺ =882)

Example 48: Preparation of compound 48

In a nitrogen atmosphere, compound sub48 (20 g, 31.5 mmol), compound D (9.6 g, 34.7 mmol) and sodium tert-butoxide (9.1 g, 94.6 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (81 mg, 0.158 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 48. (17.2 g, yield 63%, MS: [M+H] ⁺ =866)

Example 49: Preparation of compound 49

In a nitrogen atmosphere, compound sub2 (20 g, 41.3 mmol), compound C (12.6 g, 45.54 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (106 mg, 0.207 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 49. (13.6 g, yield 46%, MS: [M+H] ⁺ =715)

Example 50: Preparation of compound 50

In a nitrogen atmosphere, compound sub3 (20 g, 41.3 mmol), compound D (12.6 g, 45.54 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (106 mg, 0.207 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 50. (15.1 g, yield 51%, MS: [M+H] ⁺ =715)

Example 51: Preparation of compound 51

In a nitrogen atmosphere, compound sub4 (20 g, 41.3 mmol), compound D (12.6 g, 45.54 mmol) and sodium tert-butoxide (11.9 g, 124 mmol) were added to xylene (200 ml) and stirred and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (106 mg, 0.207 mmol) was added. After 2 hours, the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. After this, the compound was again dissolved in chloroform (CHCl ₃ , 500 ml), washed twice with water, the organic layer was separated, treated with magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 51. (14.7 g, yield 50%, MS: [M+H] ⁺ =715)

Experimental Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, 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 cleaning 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, and after drying, it was 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.

The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 Å, but the following A-1 compound was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following EB-1 compound was vacuum-deposited to a film thickness of 150 Å on the hole transport layer to form an electron blocking layer. Then, on the electron blocking layer, the compound 1 prepared in Example 1 and the compound Dp-7 below were vacuum deposited in a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 to By maintaining 5×10 ^-6 torr, an organic light-emitting device was manufactured.

Experimental Examples 2 to 51 and Comparative Experimental Examples 1 to 11

An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds shown in Tables 1 and 2 were used instead of Compound 1 in the organic light emitting device of Experimental Example 1.

When a current of 10 mA/cm ² was applied to the organic light emitting diodes prepared in Experimental Examples 1 to 51 and Comparative Experimental Examples 1 to 11, voltage, efficiency and lifetime were measured (based on 6000 nits), and the results are shown in the table below 1 and 2 are shown. The lifetime T ₉₅ means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division host material Driving voltage (V) Efficiency (cd/A) Life T ₉₅ (hr) luminous color Experimental Example 1 compound 1 3.51 44.5 280 Red Experimental Example 2 compound 2 3.65 42.5 286 Red Experimental Example 3 compound 3 3.70 43.7 279 Red Experimental Example 4 compound 4 3.78 42.9 268 Red Experimental Example 5 compound 5 3.84 44.0 278 Red Experimental Example 6 compound 6 3.58 47.8 Red Experimental Example 7 compound 7 3.60 45.6 295 Red Experimental Example 8 compound 8 3.55 45.8 290 Red Experimental Example 9 compound 9 3.63 45.8 281 Red Experimental Example 10 compound 10 3.59 47.6 286 Red Experimental Example 11 compound 11 46.4 278 Red Experimental Example 12 compound 12 3.38 47.8 271 Red Experimental Example 13 compound 13 3.64 46.8 261 Red Experimental Example 14 compound 14 3.65 47.4 308 Red Experimental Example 15 compound 15 3.72 46.0 259 Red Experimental Example 16 compound 16 3.60 45.3 292 Red Experimental Example 17 compound 17 3.54 46.5 311 Red Experimental Example 18 compound 18 3.50 45.1 321 Red Experimental Example 19 compound 19 3.53 45.7 315 Red Experimental Example 20 compound 20 3.67 50.2 327 Red Experimental Example 21 compound 21 3.61 48.7 332 Red Experimental Example 22 compound 22 3.66 49.1 341 Red Experimental Example 23 compound 23 3.63 48.8 354 Red Experimental Example 24 compound 24 3.34 48.3 Red Experimental Example 25 compound 25 3.49 47.5 310 Red Experimental Example 26 compound 26 3.50 43.1 309 Red Experimental Example 27 compound 27 3.58 47.1 298 Red Experimental Example 28 compound 28 3.54 48.0 321 Red Experimental Example 29 compound 29 3.58 47.3 334 Red Experimental Example 30 compound 30 3.67 46.5 287 Red

division host material Driving voltage (V) Efficiency (cd/A) Life T ₉₅ (hr) luminous color Experimental Example 31 compound 31 3.49 49.5 307 Red Experimental Example 32 compound 32 3.66 49.2 318 Red Experimental Example 33 compound 33 3.63 48.7 354 Red Experimental Example 34 compound 34 3.57 48.3 336 Red Experimental Example 35 compound 35 3.61 51.1 351 Red Experimental Example 36 compound 36 3.68 48.1 Red Experimental Example 37 compound 37 3.47 49.0 329 Red Experimental Example 38 compound 38 3.62 48.0 357 Red Experimental Example 39 compound 39 3.54 48.7 343 Red Experimental Example 40 compound 40 3.61 49.4 345 Red Experimental Example 41 compound 41 3.52 50.6 358 Red Experimental Example 42 compound 42 3.50 47.8 324 Red Experimental Example 43 compound 43 3.47 49.0 303 Red Experimental Example 44 compound 44 3.49 48.5 290 Red Experimental Example 45 compound 45 3.55 324 Red Experimental Example 46 compound 46 3.54 51.2 313 Red Experimental Example 47 compound 47 3.37 48.5 288 Red Experimental Example 48 compound 48 3.35 47.2 326 Red Experimental Example 49 compound 49 45.4 312 Red Experimental Example 50 compound 50 3.50 47.6 345 Red Experimental Example 51 compound 51 3.39 48.9 329 Red Comparative Experiment Example 1 C-1 4.61 32.5 105 Red Comparative Experimental Example 2 C-2 4.52 36.8 178 Red Comparative Experimental Example 3 C-3 4.15 34.7 120 Red Comparative Experimental Example 4 C-4 4.08 36.5 165 Red Comparative Experiment Example 5 C-5 4.34 39.1 146 Red Comparative Experiment Example 6 C-6 4.12 37.5 110 Red Comparative Experimental Example 7 C-7 4.97 31.2 97 Red Comparative Experimental Example 8 C-8 5.11 34.6 132 Red Comparative Experimental Example 9 C-9 4.85 35.4 105 Red Comparative Experimental Example 10 C-10 4.38 39.8 145 Red Comparative Experimental Example 11 RH-1 4.34 35.7 175 Red

According to Tables 1 and 2, it was confirmed that the organic light emitting device of the experimental example had a significantly lower driving voltage and significantly higher efficiency and lifespan than the organic light emitting device of the comparative example.

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

Claims (9)

A compound that is any one selected from the group consisting of:

.
delete delete delete delete delete 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 according to claim 1 .
8. The method of claim 7,
The organic material layer may include an emission layer, wherein the emission layer includes a host material.
9. The method of claim 8,
The host material is an organic light emitting device comprising a compound selected from the group consisting of the compound.

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