Organic Light-Emitting Device

Abstract

The present invention provides an organic light-emitting device with improved driving voltage, efficiency, and lifespan.

Description

Technical Field

[0001] Cross - reference to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2019-0121787 filed on October 1, 2019 and Korean Patent Application No. 10-2020-0128123 filed on October 5, 2020, and includes all the contents disclosed in the documents of the Korean patent applications as part of this specification.

[0003] The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan. Background Art

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast ratio, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus extensive research is being conducted.

[0005] An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure composed of different substances respectively. For example, it can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state again.

[0006] Regarding the organic light emitting device as described above, there is a continuous demand for the development of an organic light emitting device with improved driving voltage, efficiency, and lifespan.

[0007] Prior Art Documents

[0008] Patent Documents

[0009] (Patent Document 1) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical Problem

[0011] The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan.

[0012] Solution to the Problem

[0013] The present invention provides the following organic light emitting device:

[0014] An organic light-emitting device, comprising:

[0015] An anode;

[0016] A cathode; and

[0017] A light-emitting layer between the above-mentioned anode and cathode,

[0018] The above-mentioned light-emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2:

[0019] [Chemical Formula 1]

[0020]

[0021] In the above Chemical Formula 1,

[0022] X is N or CH, but at least one of X is N,

[0023] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C containing any one or more selected from N, O, and S 5-60 heteroaryl,

[0024] R 1 to R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted C 6-60 aryl, or two adjacent ones combine to form a benzene ring,

[0025] R 5 to R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted C 6-60 aryl,

[0026] n1 is an integer from 0 to 6,

[0027] n2 and n3 are each independently an integer from 0 to 3,

[0028] [Chemical Formula 2]

[0029]

[0030] In the above Chemical Formula 2,

[0031] A' is a benzene ring fused to two adjacent five-membered rings,

[0032] L' 1 and L' 2 are each independently a single bond; a substituted or unsubstituted C 6-60Arylene; or substituted or unsubstituted C containing any one or more selected from N, O and S 5-60 heteroarylene,

[0033] Ar' 1 and Ar' 2 each independently is substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing any one or more selected from N, O and S 5-60 heteroaryl,

[0034] R' 1 and R' 2 each independently is hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl,

[0035] n'1 and n'2 are each independently an integer from 0 to 4.

[0036] Advantages of the Invention

[0037] The above organic light-emitting device includes the compounds represented by Chemical Formula 1 and Chemical Formula 2 in the light-emitting layer, thereby having excellent driving voltage, efficiency, and lifespan. Brief Description of the Drawings

[0038] Figure 1 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is illustrated.

[0039] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 is illustrated.

[0040] Figure 3 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 12, and a cathode 4 is illustrated. Detailed Description of the Invention

[0041] Hereinafter, a more detailed description will be given to help understand the present invention.

[0042] In this specification, a bond connecting to other substituents is represented.

[0043] In this specification, the term "substituted or unsubstituted" means being substituted or unsubstituted by one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkyl thioxy group; an aryl thioxy group; an alkyl sulfoxy group; an aryl sulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroarylamino group; an arylamino group; an arylphosphine group; or a heterocyclic group containing one or more of N, O, and S atoms, or being substituted or unsubstituted by a substituent formed by linking two or more of the above-exemplified substituents. For example, the "substituent formed by linking two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group or may be interpreted as a substituent formed by linking two phenyl groups.

[0044] In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, it may be a group having the following structure, but is not limited thereto.

[0045]

[0046] In this specification, in the ester group, the oxygen of the ester group may be substituted by 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 group having the following structural formula, but is not limited thereto.

[0047]

[0048] In this specification, the number of carbon atoms of the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, it may be a group having the following structure, but is not limited thereto.

[0049]

[0050] In this specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0051] In this specification, specific examples of the boron group include trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, phenylboron, etc., but are not limited thereto.

[0052] In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0053] In this specification, the above alkyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the above alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the above alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the above alkyl group is 1 to 6. 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, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0054] In this specification, the above alkenyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the above alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0055] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are 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, etc., but are not limited thereto.

[0056] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the above aryl group, as the monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As the above polycyclic aryl group, it may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, -yl group, a fluorenyl group, etc., but is not limited thereto.

[0057] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the above fluorenyl group is substituted, it may become etc. But it is not limited thereto.

[0058] In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophenyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, -azolyl group, a diazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzo -azolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuryl group, a phenanthroline group, an iso -azolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuryl group, etc., but is not limited thereto.

[0059] In this specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamino group is the same as the exemplified aryl group above. In this specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the exemplified alkyl group above. In this specification, the heteroaryl group in the heteroarylamine may apply the above description regarding the heterocyclic group. In this specification, the alkenyl group in the aralkenyl group is the same as the exemplified alkenyl group above. In this specification, the arylene group is a divalent group, and in addition, the above description regarding the aryl group may be applied. In this specification, the heteroarylene group is a divalent group, and in addition, the above description regarding the heterocyclic group may be applied. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by the combination of two substituents, and in addition, the above description regarding the aryl group or cycloalkyl group may be applied. In this specification, the heterocyclic ring is not a monovalent group, but is formed by the combination of two substituents, and in addition, the above description regarding the heterocyclic group may be applied.

[0060] Hereinafter, the present invention will be described in detail according to each component.

[0061] Anode and cathode

[0062] The anode and cathode used in the present invention refer to the electrodes used in an organic light-emitting device.

[0063] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is generally preferred. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but not limited thereto.

[0064] As the above-mentioned cathode material, in order to enable electrons to be easily injected into the organic layer, a material with a small work function is generally preferred. Specific examples of the above-mentioned cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multi-layer structure materials such as LiF / Al or LiO 2 / Al, etc., but not limited thereto.

[0065] Light-emitting layer

[0066] The light-emitting layer used in the present invention refers to a layer that can emit light in the visible light region by combining holes and electrons received from the anode and cathode. Generally speaking, the light-emitting layer contains a host material and a dopant material. In the present invention, the compounds represented by the above Chemical Formula 1 and the compounds represented by the above Chemical Formula 2 are included as the host.

[0067] Preferably, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0068] [Chemical Formula 1-1]

[0069]

[0070] [Chemical Formula 1-2]

[0071]

[0072] [Chemical Formula 1-3]

[0073]

[0074] In the above Chemical Formulas 1-1 to 1-3, X, Ar 1 、Ar2 , R 1 to R 5 , and n1 is the same as defined above.

[0075] Preferably, each X is N.

[0076] Preferably, Ar 1 and Ar 2 are each independently phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.

[0077] Preferably, R 5 to R 7 are each independently hydrogen, deuterium, phenyl, biphenyl, naphthyl or phenanthryl. More preferably, R 5 is hydrogen, deuterium, phenyl, biphenyl, naphthyl or phenanthryl, R 6 and R 7 are hydrogen or deuterium.

[0078] Preferably, n1 is 0 or 1.

[0079] Preferably, n2 and n3 are each independently 0 or 1.

[0080] Representative examples of the compound represented by Chemical Formula 1 above are shown below.

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] On the other hand, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in Reaction Formula 1 below.

[0097] [Reaction Formula 1]

[0098]

[0099] In the above Reaction Formula 1, the remaining definitions except for X' and X" are the same as the above definitions, and X' and X" are each independently a halogen, and more preferably, each independently bromine or chlorine. Step 1 of the above Reaction Formula 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the Suzuki coupling reaction can be changed according to the techniques known in the art. Step 2 of the above Reaction Formula 1 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to the techniques known in the art. The above production method can be further specified in the production examples described later.

[0100] Preferably, the above Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-5:

[0101] [Chemical Formula 2-1]

[0102]

[0103] [Chemical Formula 2-2]

[0104]

[0105] [Chemical Formula 2-3]

[0106]

[0107] [Chemical Formula 2-4]

[0108]

[0109] [Chemical Formula 2-5]

[0110]

[0111] In the above Chemical Formulas 2-1 to 2-5, L' 1 , L' 2 , Ar' 1 , Ar' 2 , R' 1 , R' 2 , n'1 and n'2 are the same as the above definitions.

[0112] Preferably, L' 1 and L' 2 are each independently a single bond, a phenylene or a naphthylene.

[0113] Preferably, Ar' 1 and Ar' 2 are each independently a phenyl, a biphenyl, a terphenyl, a quaterphenyl, a naphthyl, a dimethylfluorenyl, a dibenzofuranyl, or a dibenzothiophenyl.

[0114] Preferably, R' 1 and R' 2 are each independently hydrogen.

[0115] Representative examples of the compound represented by Chemical Formula 2 above are shown below.

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] On the other hand, the compound represented by the above Chemical Formula 2 can be produced by the production method shown in Reaction Formula 2 below.

[0138] [Reaction Formula 2]

[0139]

[0140] In the above Reaction Formula 2, the remaining definitions except for X' and X" are the same as the above definitions, and X' and X" are each independently a halogen, and more preferably, each independently bromine or chlorine. Step 1 of the above Reaction Formula 2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to the techniques known in the art. Step 2 of the above Reaction Formula 2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to the techniques known in the art. The above production method can be more specific in the production examples described later.

[0141] On the other hand, the weight ratio of the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 is from 1:99 to 99:1, preferably from 10:90 to 90:10, 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0142] On the other hand, in addition to the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2, the above light-emitting layer may contain a dopant.

[0143] The above dopant material is not particularly limited as long as it is a substance used in an organic light-emitting device. As an example, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and there are pyrene, anthracene having an arylamino group, , such as diindenopyrene, etc. Styrenylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino. Specifically, there are styrenylamine, styrenyldiamine, styrenyltriamine, styrenyltetramine, etc., but are not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but are not limited thereto.

[0144] Hole transport layer

[0145] The organic light-emitting device according to the present invention may include a hole transport layer between the above-mentioned light-emitting layer and the anode.

[0146] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable.

[0147] Specific examples of the above-mentioned hole transport material include arylamine-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, etc., but are not limited thereto.

[0148] Hole injection layer

[0149] The organic light-emitting device according to the present invention may further include a hole injection layer between the above-mentioned anode and the hole transport layer as needed.

[0150] The above-mentioned hole injection layer is a layer that injects holes from the electrode. As the hole injection material, the following compounds are preferably used: compounds having the ability to transport holes, having the effect of injecting holes from the anode, having an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and having excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.

[0151] Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and polyaniline and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0152] Electron transport layer

[0153] The organic light-emitting device according to the present invention may include an electron transport layer between the above-mentioned light-emitting layer and the cathode.

[0154] The above-mentioned electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode, transports the electrons to the light-emitting layer, and inhibits the transfer of holes from the light-emitting layer. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable.

[0155] As a specific example of the above-mentioned electron transport material, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq 3 complexes, organic radical compounds, hydroxyflavone-metal complexes, etc., but not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are ordinary materials with a low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each accompanied by an aluminum layer or a silver layer in each case.

[0156] Electron injection layer

[0157] The organic light-emitting device according to the present invention may further include an electron injection layer between the above-mentioned electron transport layer and the cathode as needed.

[0158] The above-mentioned electron injection layer is a layer that injects electrons from the electrode, and preferably uses the following compounds: compounds having excellent electron transport ability, having the effect of injecting electrons from the cathode, excellent electron injection effect on the light-emitting layer or the light-emitting material, preventing the migration of excitons generated in the light-emitting layer to the hole injection layer, and having excellent thin film forming ability.

[0159] As a specific example of the material that can be used for the above-mentioned electron injection layer, there are fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

[0160] As the above-mentioned metal coordination compounds, there are lithium 8-hydroxyquinoline, zinc bis(8-hydroxyquinoline), copper bis(8-hydroxyquinoline), manganese bis(8-hydroxyquinoline), aluminum tris(8-hydroxyquinoline), aluminum tris(2-methyl-8-hydroxyquinoline), gallium tris(8-hydroxyquinoline), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(1-naphthol), gallium bis(2-methyl-8-quinoline)(2-naphthol), etc., but not limited thereto.

[0161] Organic light-emitting device

[0162] The structure of the organic light-emitting device according to the present invention is illustrated in Figure 1 . Figure 1 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is illustrated. In addition, Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 is illustrated. In addition, Figure 3 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 12, and a cathode 4 is illustrated. In the structure as described above, the compound represented by the above Chemical Formula 1 may be included in one or more of the above hole injection layer, hole transport layer, electron suppression layer, light-emitting layer, hole blocking layer, and electron transport and injection layer.

[0163] The organic light-emitting device according to the present invention can be manufactured by sequentially laminating the above components. At this time, it can be manufactured as follows: using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then after forming the above layers on the anode, a substance that can be used as a cathode is evaporated thereon for manufacturing. In addition to this method, an organic light-emitting device can also be manufactured by evaporating from the cathode material to the anode material in the reverse order of the above-described composition on the substrate (WO2003 / 012890). In addition, not only can a vacuum evaporation method be used, but also a solution coating method can be used to form a host and a dopant into a light-emitting layer. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0164] On the other hand, depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0165] Hereinafter, preferred embodiments are presented to assist in understanding the present invention. However, the following embodiments are provided only to more easily understand the present invention, and the content of the present invention is not limited thereto.

[0166] [Manufacturing Example]

[0167] Manufacturing Example 1: Preparation of Compound 1

[0168]

[0169] Under a nitrogen atmosphere, compound substance (sub) 1 (15 g, 56 mmol) and compound a (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, and then 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 by silica gel column chromatography to produce compound substance 1-1 (16.5 g, yield 68%).

[0170] MS: [M+H] + = 434

[0171] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-1 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, and then the organic layer was separated. It was treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 1 (18.4 g, yield 65%).

[0172] MS: [M+H] + = 615

[0173] Production Example 2: Production of Compound 2

[0174]

[0175] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound b (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-2 (16 g, yield 66%).

[0176] MS: [M+H] + = 434

[0177] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-2 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, then the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 2 (15.3 g, yield 54%).

[0178] MS: [M+H] + = 615

[0179] Production Example 3: Production of Compound 3

[0180]

[0181] Under a nitrogen atmosphere, compound B (10 g, 37.4 mmol), compound substance 1-2 (17.9 g, 41.1 mmol), and sodium tert-butoxide (7.2 g, 74.8 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, then the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 3 (12.7 g, yield 51%).

[0182] MS: [M+H]+ = 665

[0183] Production Example 4: Production of Compound 4

[0184]

[0185] Under a nitrogen atmosphere, Compound Substance 2 (15 g, 41.9 mmol) and Compound c (11.4 g, 46.1 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.3 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. The organic layer was distilled. It was redissolved in chloroform, 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 by silica gel column chromatography to produce Compound Substance 1-3 (17.3 g, yield 79%).

[0186] MS: [M+H] + = 524

[0187] Under a nitrogen atmosphere, Compound A (10 g, 46 mmol), Compound Substance 1-3 (26.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 4 (21.1 g, yield 65%).

[0188] MS: [M+H] + = 705

[0189] Production Example 5: Production of Compound 5

[0190]

[0191] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound d (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-4 (15.3 g, yield 63%).

[0192] MS: [M+H] + = 434

[0193] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-4 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 5 (17 g, yield 60%).

[0194] MS: [M+H] + = 615

[0195] Production Example 6: Production of Compound 6

[0196]

[0197] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound e (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-5 (18.9 g, yield 78%).

[0198] MS: [M+H] + = 434

[0199] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-5 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 6 (14.1 g, yield 50%).

[0200] MS: [M+H] + = 615

[0201] Production Example 7: Production of Compound 7

[0202]

[0203] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound f (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-6 (17.7 g, yield 73%).

[0204] MS: [M+H] + = 434

[0205] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-6 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 7 (17.5 g, yield 62%).

[0206] MS: [M+H] + = 615

[0207] Production Example 8: Production of Compound 8

[0208]

[0209] Under a nitrogen atmosphere, compound B (10 g, 37.4 mmol), compound substance 1-6 (17.9 g, 41.1 mmol), and sodium tert-butoxide (7.2 g, 74.8 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 8 (16.9 g, yield 68%).

[0210] MS: [M+H] + = 665

[0211] Production Example 9: Production of Compound 9

[0212]

[0213] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound g (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-7 (18 g, yield 74%).

[0214] MS: [M+H] + = 434

[0215] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-7 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 9 (19.8 g, yield 70%).

[0216] MS: [M+H] + = 615

[0217] Production Example 10: Production of Compound 10

[0218]

[0219] Under a nitrogen atmosphere, compound substance 3 (15 g, 43.6 mmol) and compound h (11.8 g, 48 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in water (54 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-8 (14.2 g, yield 64%).

[0220] MS: [M+H] + = 510

[0221] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-8 (25.4 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 10 (18.1 g, yield 57%).

[0222] MS: [M+H] + = 691

[0223] Production Example 11: Production of Compound 11

[0224]

[0225] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound i (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, 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 by silica gel column chromatography to produce compound substance 1-9 (18.9 g, yield 78%).

[0226] MS: [M+H] + = 434

[0227] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-9 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 11 (16.7 g, yield 59%).

[0228] MS: [M+H] + = 615

[0229] Production Example 12: Production of Compound 12

[0230]

[0231] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound j (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-10 (15.5 g, yield 64%).

[0232] MS: [M+H] + = 434

[0233] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-10 (22 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 12 (16.7 g, yield 59%).

[0234] MS: [M+H]+ = 615

[0235] Production Example 13: Production of Compound 13

[0236]

[0237] Under a nitrogen atmosphere, Compound Substance 4 (15 g, 47.2 mmol) and Compound k (12.8 g, 51.9 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was redissolved in chloroform, 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 by silica gel column chromatography to produce Compound Substance 1-11 (15.1 g, yield 66%).

[0238] MS: [M+H] + = 484

[0239] Under a nitrogen atmosphere, Compound A (10 g, 46 mmol), Compound Substance 1-11 (24.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 13 (15.9 g, yield 52%).

[0240] MS: [M+H] + = 665

[0241] Production Example 14: Production of Compound 14

[0242]

[0243] Under a nitrogen atmosphere, compound substance 5 (15 g, 41.9 mmol) and compound l (11.4 g, 46.1 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.3 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-12 (14.7 g, yield 67%).

[0244] MS: [M+H] + =524

[0245] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-12 (26.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, then the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 14 (20.1 g, yield 62%).

[0246] MS: [M+H] + =705

[0247] Production Example 15: Production of Compound 15

[0248]

[0249] Under a nitrogen atmosphere, compound substance 2 (15 g, 41.9 mmol) and compound m (11.4 g, 46.1 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-13 (17.1 g, yield 78%).

[0250] MS: [M+H] + = 524

[0251] Under a nitrogen atmosphere, compound C (10 g, 37.4 mmol), compound substance 1-13 (21.6 g, 41.2 mmol), and sodium tert-butoxide (7.2 g, 74.8 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 15 (13.2 g, yield 50%).

[0252] MS: [M+H] + = 705

[0253] Production Example 16: Production of Compound 16

[0254]

[0255] Under a nitrogen atmosphere, compound substance 6 (15 g, 40.8 mmol) and compound n (11.1 g, 44.9 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (16.9 g, 122.3 mmol) was dissolved in water (51 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-14 (15.4 g, yield 71%).

[0256] MS: [M+H] + = 534

[0257] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-14 (27 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 16 (19.4 g, yield 59%).

[0258] MS: [M+H] + = 715

[0259] Production Example 17: Production of Compound 17

[0260]

[0261] Under a nitrogen atmosphere, compound substance 4 (15 g, 47.2 mmol) and compound o (12.8 g, 51.9 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-15 (16.6 g, yield 73%).

[0262] MS: [M+H] + = 484

[0263] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-15 (24.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 17 (18 g, yield 59%).

[0264] MS: [M+H] + = 665

[0265] Production Example 18: Production of Compound 18

[0266]

[0267] Under a nitrogen atmosphere, Compound Substance 7 (15 g, 47.2 mmol) and Compound p (12.8 g, 51.9 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. The organic layer was distilled. It was redissolved in chloroform, washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added, and after stirring, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound Substance 1-16 (16.9 g, yield 74%).

[0268] MS: [M+H] + = 484

[0269] Under a nitrogen atmosphere, Compound A (10 g, 46 mmol), Compound Substance 1-16 (24.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, and then the organic layer was separated. It was treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 18 (18.3 g, yield 60%).

[0270] MS: [M+H] + = 665

[0271] Production Example 19: Production of Compound 19

[0272]

[0273] Under a nitrogen atmosphere, compound substance 3 (15 g, 43.6 mmol) and compound b (11.8 g, 48 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in water (54 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-17 (17.1 g, yield 77%).

[0274] MS: [M+H] + = 510

[0275] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-17 (25.4 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 19 (21 g, yield 66%).

[0276] MS: [M+H] + = 691

[0277] Production Example 20: Production of Compound 20

[0278]

[0279] Under a nitrogen atmosphere, compound substance 8 (15 g, 35.7 mmol) and compound p (9.7 g, 39.3 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in water (44 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.1 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-18 (13 g, yield 62%).

[0280] MS: [M+H] + = 586

[0281] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-18 (29.7 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 20 (24.7 g, yield 70%).

[0282] MS: [M+H] + = 767

[0283] Production Example 21: Production of Compound 21

[0284]

[0285] Under a nitrogen atmosphere, compound substance 4 (15 g, 47.2 mmol) and compound q (12.8 g, 51.9 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-19 (17.8 g, yield 78%).

[0286] MS: [M+H] + = 484

[0287] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-19 (24.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 21 (16.8 g, yield 55%).

[0288] MS: [M+H] + = 665

[0289] Production Example 22: Production of Compound 22

[0290]

[0291] Under a nitrogen atmosphere, compound substance 1 (15 g, 56 mmol) and compound k (15.2 g, 61.6 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.7 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, 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 by silica gel column chromatography to produce compound substance 1-20 (23.4 g, yield 80%).

[0292] MS: [M+H] + = 524

[0293] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-20 (26.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 22 (16.2 g, yield 50%).

[0294] MS: [M+H] + = 705

[0295] Production Example 23: Production of Compound 23

[0296]

[0297] Under a nitrogen atmosphere, Compound 9 (15 g, 41.9 mmol) and Compound i (11.4 g, 46.1 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.3 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and then the organic layer was distilled. It was redissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 1-21 (14.3 g, yield 65%).

[0298] MS: [M+H] + = 524

[0299] Under a nitrogen atmosphere, Compound D (10 g, 37.4 mmol), Compound 1-21 (21.6 g, 41.1 mmol), and sodium tert-butoxide (7.2 g, 74.8 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 23 (17.5 g, yield 62%).

[0300] MS: [M+H] + = 755

[0301] Production Example 24: Production of Compound 24

[0302]

[0303] Under a nitrogen atmosphere, compound substance 10 (15 g, 43.6 mmol) and compound r (11.8 g, 48 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.3 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-22 (16 g, yield 72%).

[0304] MS: [M+H] + = 510

[0305] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-22 (25.8 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely redissolved in chloroform, washed twice with water, and then the organic layer was separated. It was treated with anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 24 (22.2 g, yield 70%).

[0306] MS: [M+H] + = 691

[0307] Production Example 25: Production of Compound 25

[0308]

[0309] Under a nitrogen atmosphere, compound substance 10 (15 g, 43.6 mmol) and compound s (11.8 g, 48 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.3 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. It was redissolved in chloroform, washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound substance 1-23 (15.8, yield 71%).

[0310] MS: [M+H] + = 510

[0311] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-23 (25.8 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 25 (21.3 g, yield 67%).

[0312] MS: [M+H] + = 691

[0313] Production Example 26: Production of Compound 26

[0314]

[0315] Under a nitrogen atmosphere, compound substance 2 (15 g, 41.9 mmol) and compound t (11.4 g, 46.1 mmol) were added to THF (300 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.3 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, 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 by silica gel column chromatography to produce compound substance 1-24 (14 g, yield 64%).

[0316] MS: [M+H] + = 524

[0317] Under a nitrogen atmosphere, compound A (10 g, 46 mmol), compound substance 1-24 (26.5 g, 50.6 mmol), and sodium tert-butoxide (8.8 g, 92.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 26 (22.7 g, yield 70%).

[0318] MS: [M+H] + = 705

[0319] Production Example 27: Production of Compound 27

[0320]

[0321] Under a nitrogen atmosphere, compound E (10 g, 39 mmol), compound substance 11 (9.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound E-1 (10.8 g, yield 68%).

[0322] MS: [M+H] + = 409

[0323] Under a nitrogen atmosphere, compound E-1 (10 g, 24.5 mmol), compound substance 12 (6.3 g, 26.9 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 27 (8.2 g, yield 60%).

[0324] MS: [M+H] + = 561

[0325] Production Example 28: Production of Compound 28

[0326]

[0327] Under a nitrogen atmosphere, Compound E (10 g, 39 mmol), Compound Substance 13 (11 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound E-2 (9.8 g, yield 55%).

[0328] MS: [M+H] + = 459

[0329] Under a nitrogen atmosphere, Compound E-2 (10 g, 21.8 mmol), Compound Substance 14 (5 g, 24 mmol), and sodium tert-butoxide (4.2 g, 43.6 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 28 (7.1 g, yield 56%).

[0330] MS: [M+H] + = 585

[0331] Production Example 29: Production of Compound 29

[0332]

[0333] Under a nitrogen atmosphere, compound F (10 g, 39 mmol), compound substance 15 (6.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound F-1 (8.3 g, yield 64%).

[0334] MS: [M+H] + = 333

[0335] Under a nitrogen atmosphere, compound F-1 (10 g, 30.1 mmol), compound substance 16 (10.2 g, 33.1 mmol), and sodium tert-butoxide (5.8 g, 60.2 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 29 (9.9 g, yield 59%).

[0336] MS: [M+H] + = 561

[0337] Production Example 30: Production of Compound 30

[0338]

[0339] Under a nitrogen atmosphere, compound E (10 g, 39 mmol), compound substance 17 (12.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound E-3 (9.6 g, yield 51%).

[0340] MS: [M+H] + = 485

[0341] Under a nitrogen atmosphere, compound E-3 (10 g, 20.6 mmol), compound substance 18 (4.7 g, 22.7 mmol), and sodium tert-butoxide (4 g, 41.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 30 (7.8 g, yield 62%).

[0342] MS: [M+H] + = 611

[0343] Production Example 31: Production of Compound 31

[0344]

[0345] Under a nitrogen atmosphere, compound F (10 g, 39 mmol), compound substance 14 (17.8 g, 85.8 mmol), and sodium tert-butoxide (15 g, 156.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.8 g, 1.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 31 (11.3 g, yield 57%).

[0346] MS: [M+H] + = 509

[0347] Production Example 32: Production of Compound 32

[0348]

[0349] Under a nitrogen atmosphere, compound F (10 g, 39 mmol), compound substance 12 (9.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound F-2 (9.6 g, yield 60%).

[0350] MS: [M+H] + = 409

[0351] Under a nitrogen atmosphere, compound F-2 (10 g, 24.5 mmol), compound substance 19 (6.7 g, 26.9 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 32 (8.2 g, yield 58%).

[0352] MS: [M+H] + = 575

[0353] Production Example 33: Production of Compound 33

[0354]

[0355] Under a nitrogen atmosphere, compound F-2 (10 g, 24.5 mmol), compound substance 20 (7.6 g, 26.9 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 33 (8.1 g, yield 54%).

[0356] MS: [M+H] + = 611

[0357] Production Example 34: Production of Compound 34

[0358]

[0359] Under a nitrogen atmosphere, Compound F-2 (10 g, 24.5 mmol), Compound Substance 21 (7.6 g, 26.9 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 34 (8.7 g, yield 58%).

[0360] MS: [M+H] + = 611

[0361] Production Example 35: Production of Compound 35

[0362]

[0363] Under a nitrogen atmosphere, Compound G (10 g, 39 mmol), Compound Substance 22 (9.6 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound G-1 (10.2 g, yield 62%).

[0364] MS: [M+H] + = 423

[0365] Under a nitrogen atmosphere, compound G-1 (10 g, 23.7 mmol), compound substance 14 (5.4 g, 26 mmol), and sodium tert-butoxide (4.5 g, 47.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 35 (8.6 g, yield 66%).

[0366] MS: [M+H] + = 549

[0367] Production Example 36: Production of Compound 36

[0368]

[0369] Under a nitrogen atmosphere, compound G (10 g, 39 mmol), compound substance 23 (12.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound G-2 (12.8 g, yield 68%).

[0370] MS: [M+H] + = 485

[0371] Under a nitrogen atmosphere, compound G-2 (10 g, 20.6 mmol), compound substance 12 (5.3 g, 22.7 mmol), and sodium tert-butoxide (4 g, 41.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 36 (7 g, yield 53%).

[0372] MS: [M+H] + = 637

[0373] Production Example 37: Production of Compound 37

[0374]

[0375] Under a nitrogen atmosphere, Compound G (10 g, 39 mmol), Compound Substance 14 (8.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound G-3 (9.7 g, yield 65%).

[0376] MS: [M+H] + = 383

[0377] Under a nitrogen atmosphere, Compound G-3 (10 g, 26.1 mmol), Compound Substance 11 (6.7 g, 28.8 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 37 (9.1 g, yield 65%).

[0378] MS: [M+H] + = 535

[0379] Production Example 38: Production of Compound 38

[0380]

[0381] Under a nitrogen atmosphere, compound G (10 g, 39 mmol), compound substance 15 (6.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound G-4 (6.9 g, yield 53%).

[0382] MS: [M+H] + = 333

[0383] Under a nitrogen atmosphere, compound G-4 (10 g, 30.1 mmol), compound substance 24 (8.7 g, 33.1 mmol), and sodium tert-butoxide (5.8 g, 60.2 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 38 (8.4 g, yield 54%).

[0384] MS: [M+H] + = 515

[0385] Production Example 39: Production of Compound 39

[0386]

[0387] Under a nitrogen atmosphere, compound G (10 g, 39 mmol), compound substance 19 (9.6 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound G-5 (10.2 g, yield 62%).

[0388] MS: [M+H] + = 423

[0389] Under a nitrogen atmosphere, compound G-5 (10 g, 23.7 mmol), compound substance 21 (7.4 g, 26 mmol), and sodium tert-butoxide (4.5 g, 47.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 39 (8.3 g, yield 56%).

[0390] MS: [M+H] + = 625

[0391] Production Example 40: Production of Compound 40

[0392]

[0393] Under a nitrogen atmosphere, compound G (10 g, 39 mmol), compound substance 25 (9.6 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound G-6 (9.9 g, yield 60%).

[0394] MS: [M+H] + = 423

[0395] Under a nitrogen atmosphere, compound G-6 (10 g, 23.7 mmol), compound substance 26 (7.4 g, 26 mmol), and sodium tert-butoxide (4.5 g, 47.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 40 (8.1 g, yield 55%).

[0396] MS: [M+H] + = 625

[0397] Production Example 41: Production of Compound 41

[0398]

[0399] Under a nitrogen atmosphere, Compound G-4 (10 g, 30.1 mmol), Compound Substance 27 (8.7 g, 33.1 mmol), and sodium tert-butoxide (5.8 g, 60.2 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 41 (9.1 g, yield 59%).

[0400] MS: [M+H] + = 515

[0401] Production Example 42: Production of Compound 42

[0402]

[0403] Under a nitrogen atmosphere, Compound H (10 g, 39 mmol), Compound Substance 11 (20 g, 85.8 mmol), and sodium tert-butoxide (15 g, 156.1 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.8 g, 1.6 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 42 (14.6 g, yield 67%).

[0404] MS: [M+H] + = 561

[0405] Production Example 43: Production of Compound 43

[0406]

[0407] Under a nitrogen atmosphere, compound H (10 g, 39 mmol), compound substance 23 (12.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound H-1 (13.2 g, yield 70%).

[0408] MS: [M+H] + = 485

[0409] Under a nitrogen atmosphere, compound H-1 (10 g, 20.6 mmol), compound substance 15 (3.6 g, 22.7 mmol), and sodium tert-butoxide (4 g, 41.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 43 (7.7 g, yield 67%).

[0410] MS: [M+H] + = 561

[0411] Production Example 44: Production of Compound 44

[0412]

[0413] Under a nitrogen atmosphere, compound H (10 g, 39 mmol), compound substance 11 (9.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound H-2 (8.8 g, yield 55%).

[0414] MS: [M+H] + = 409

[0415] Under a nitrogen atmosphere, compound H-2 (10 g, 24.5 mmol), compound substance 13 (7.6 g, 26.9 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 44 (10.5 g, yield 70%).

[0416] MS: [M+H] + = 611

[0417] Production Example 45: Production of Compound 45

[0418]

[0419] Under a nitrogen atmosphere, compound H (10 g, 39 mmol), compound substance 28 (10.7 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound H-3 (10 g, yield 57%).

[0420] MS: [M+H] + = 449

[0421] Under a nitrogen atmosphere, compound H-3 (10 g, 22.3 mmol), compound substance 15 (3.9 g, 24.5 mmol), and sodium tert-butoxide (4.3 g, 44.6 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 45 (7.4 g, yield 63%).

[0422] MS: [M+H] + = 525

[0423] Production Example 46: Production of Compound 46

[0424]

[0425] Under a nitrogen atmosphere, Compound H (10 g, 39 mmol), Compound Substance 19 (9.6 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound H-4 (8.4 g, yield 51%).

[0426] MS: [M+H] + = 423

[0427] Under a nitrogen atmosphere, Compound H-4 (10 g, 22.6 mmol), Compound Substance 11 (5.8 g, 24.9 mmol), and sodium tert-butoxide (4.3 g, 45.2 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 46 (8.6 g, yield 66%).

[0428] MS: [M+H] + = 575

[0429] Production Example 47: Production of Compound 47

[0430]

[0431] Under a nitrogen atmosphere, compound I (10 g, 39 mmol), compound substance 16 (12.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound I-1 (13.1 g, yield 60%).

[0432] MS: [M+H] + = 561

[0433] Under a nitrogen atmosphere, compound I-1 (10 g, 17.8 mmol), compound substance 12 (4.6 g, 19.6 mmol), and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 47 (7.2 g, yield 57%).

[0434] MS: [M+H] + = 713

[0435] Production Example 48: Production of Compound 48

[0436]

[0437] Under a nitrogen atmosphere, compound I (10 g, 39 mmol), compound substance 14 (8.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound I-2 (8.1 g, yield 54%).

[0438] MS: [M+H] + = 383

[0439] Under a nitrogen atmosphere, Compound I-2 (10 g, 26.1 mmol), Compound Substance 17 (8.9 g, 28.8 mmol), and sodium tert-butoxide (5 g, 52.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 48 (8.1 g, yield 51%).

[0440] MS: [M+H] + = 611

[0441] Production Example 49: Production of Compound 49

[0442]

[0443] Under a nitrogen atmosphere, Compound I (10 g, 39 mmol), Compound Substance 29 (12.1 g, 39 mmol), and sodium tert-butoxide (7.5 g, 78 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound I-3 (12.3 g, yield 65%).

[0444] MS: [M+H] + = 485

[0445] Under a nitrogen atmosphere, Compound I-3 (10 g, 20.6 mmol), Compound Substance 11 (5.3 g, 22.7 mmol), and sodium tert-butoxide (4 g, 41.3 mmol) were added to xylene (200 ml), and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce Compound 49 (7.7 g, yield 59%).

[0446] MS: [M+H] + = 637

[0447] [Example]

[0448] Example 1: Fabrication of an Organic Light-Emitting Device

[0449] A glass substrate coated with ITO (indium tin oxide) in a film thickness of was placed in distilled water dissolved with a detergent and washed using ultrasonic waves. At this time, the detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol and then dried, and then it was transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate was cleaned for 5 minutes, and then the substrate was transported to a vacuum evaporator.

[0450] On the ITO transparent electrode prepared in this way, as a hole injection layer, the following HI-1 compound was formed in a thickness of and the following A-1 compound was p-doped at a concentration of 1.5%. On the above hole injection layer, the following HT-1 compound was vacuum-evaporated to form a hole transport layer with a film thickness of . On the above hole transport layer, the following EB-1 compound was vacuum-evaporated to form an electron blocking layer with a film thickness of . On the above electron blocking layer, the above-prepared Compound 1 (first host), Compound 28 (second host), and the following Dp-7 compound (dopant) were vacuum-evaporated at a weight ratio of 49:49:2 to form a red light-emitting layer with a thickness of . On the above light-emitting layer, the following HB-1 compound was vacuum-evaporated to form a hole blocking layer with a film thickness of . On the above hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1 to form an electron injection and transport layer with a film thickness of . On the above electron injection and transport layer, lithium fluoride (LiF) was successively evaporated in a thickness of and aluminum was evaporated in a thickness of to form a cathode.

[0451]

[0452] In the above process, the evaporation rate of the organic matter was maintained at and the lithium fluoride of the cathode was maintained at The evaporation rate of aluminum is maintained The evaporation rate is maintained at 2×10 -7 ~5×10 -6 Torr during evaporation, and thus an organic light-emitting device was fabricated.

[0453] Examples 2 to 104

[0454] Compounds described in Tables 1 to 3 below were used to replace Compound 1 and Compound 28, respectively. Otherwise, an organic light-emitting device was fabricated by the same method as in Example 1 above.

[0455] Comparative Examples 1 to 15

[0456] Compounds described in Table 4 below were used to replace Compound 1 and Compound 28, respectively. Otherwise, an organic light-emitting device was fabricated by the same method as in Example 1 above. In each comparative example, no second host was used, and a first host and a dopant were used in a weight ratio of 98:2 to fabricate a light-emitting layer.

[0457] Comparative Examples 16 to 63

[0458] Compounds described in Tables 5 and 6 below were used to replace Compound 1 and Compound 28, respectively. Otherwise, an organic light-emitting device was fabricated by the same method as in Example 1 above. Each compound in Tables 5 and 6 below is as follows.

[0459]

[0460] When a current was applied to the organic light-emitting devices fabricated in the above examples and Comparative Example 1, the voltage, efficiency, and lifetime were measured, and the results are shown in Tables 1 to 6 below. Lifetime T95 represents the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

[0461] [Table 1]

[0462]

[0463]

[0464]

[0465] [Table 2]

[0466]

[0467]

[0468]

[0469] [Table 3]

[0470]

[0471]

[0472]

[0473] [Table 4]

[0474]

[0475] [Table 5]

[0476]

[0477]

[0478]

[0479]

[0480] [Table 6]

[0481]

[0482]

[0483] As shown in Tables 1 to 6 above, the organic light-emitting device of the embodiment in which the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 of the present invention are simultaneously used as the host material of the light-emitting layer shows excellent luminous efficiency and significantly improved lifetime characteristics compared with the organic light-emitting device of the comparative example in which only one of the compounds represented by the above Chemical Formulas 1 and 2 is used, or neither of them is used. Specifically, the device according to the embodiment shows high efficiency and long lifetime compared with the device of the comparative example using the compound represented by the above Chemical Formula 1 as a single host. In addition, the efficiency and lifetime characteristics are also improved for the device according to the embodiment compared with the device of the comparative example using Comparative Example Compounds C-1 to C-12 as the first host and the compound represented by the above Chemical Formula 2 as the second host. Thus, it was confirmed that when the combination of the first compound represented by the above Chemical Formula 1 and the second compound represented by the above Chemical Formula 2 is used as the host, energy transfer to the red dopant proceeds effectively in the red light-emitting layer. This can be judged because the compound represented by the above Chemical Formula 1 has high stability for electrons and holes, and also because the compound represented by the above Chemical Formula 2 is used simultaneously, so that while the amount of holes increases, a more stable balance of electrons and holes is maintained in the red light-emitting layer.

[0484] Therefore, it can be confirmed that when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 of the present invention are simultaneously used as host materials of an organic light-emitting device, the driving voltage, luminous efficiency, and / or lifetime characteristics of the organic light-emitting device can be improved.

[0485] [Symbolic Explanation]

[0486] 1: Substrate 2: Anode

[0487] 3: Light-emitting layer 4: Cathode

[0488] 5: Hole injection layer 6: Hole transport layer

[0489] 7: Light-emitting layer 8: Electron transport layer

[0490] 9: Electron blocking layer 10: Hole blocking layer

[0491] 11: Electron transport and injection layer.

Claims

1. An organic light emitting device, comprising: an anode; a cathode; and a light emitting layer between the anode and the cathode, wherein the light emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: Chemical Formula 1 In Chemical Formula 1, each X is N, Ar 1 and Ar 2 each independently is phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl, R 1 to R 4 each independently is hydrogen or deuterium, or R 1 to R 4 in which two adjacent ones combine to form a benzene ring R 5 is hydrogen, deuterium, phenyl, biphenyl, naphthyl or phenanthryl, R 6 and R 7 each independently is hydrogen or deuterium, n1 is an integer from 0 to 6, n2 and n3 are each independently an integer from 0 to 3, Chemical Formula 2 In Chemical Formula 2, A' is a benzene ring fused to two adjacent five-membered rings, L' 1 and L' 2 each independently represents a single bond, a phenylene group or a naphthylene group, Ar' 1 and Ar' 2 each independently is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, or dibenzothiophenyl, R' 1 and R' 2 each independently is hydrogen or deuterium, n'1 and n'2 are each independently an integer from 0 to 4.

2. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3: Chemical Formula 1-1 Chemical Formula 1-2 Chemical Formula 1-3 In Chemical Formulas 1-1 to 1-3, X, Ar 1 , Ar 2 , R 1 to R 5 and n1 is as defined in claim 1.

3. The organic light emitting device according to claim 1, wherein n1 is 0 or 1.

4. The organic light emitting device according to claim 1, wherein n2 and n3 are each independently 0 or 1.

5. The organic light emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the following compounds:

6. The organic light emitting device according to claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-5: Chemical Formula 2-1 Chemical Formula 2-2 Chemical Formula 2-3 Chemical Formula 2-4 Chemical Formula 2-5 In Chemical Formulas 2-1 to 2-5, L' 1 、L' 2 、Ar' 1 、Ar' 2 、R' 1 、R' 2 、n'1 and n'2 are the same as defined in claim 1.

7. The organic light emitting device according to claim 1, wherein R' 1 and R' 2 each independently is hydrogen.

8. The organic light emitting device according to claim 1, wherein the compound represented by Chemical Formula 2 is any one selected from the following compounds:

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