Novel compound and organic light-emitting device containing the same

Abstract

The present specification relates to a compound represented by Chemical Formula 1 or Chemical Formula 2, and an organic light-emitting device, wherein the organic light-emitting device is an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound represented by Chemical Formula 1 or 2.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2021-0024930 filed on February 24, 2021, and incorporates all disclosures of the Korean Patent Application No. 10-2021-0024930 into this specification.

[0003] The present invention relates to novel compounds and organic light-emitting devices containing the same. Background Art

[0004] Organic light emitting diodes (OLEDs) are currently under extensive research due to their wide viewing angles, excellent contrast, and fast response times, as well as their superior brightness, drive voltage, and response speed.

[0005] An organic light-emitting device typically has a structure comprising an anode, a cathode, and an organic layer positioned between the anode and cathode. To improve the efficiency and stability of an organic light-emitting device, the organic layer is often formed from multiple layers composed of different materials. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] The present invention relates to novel compounds and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] The present invention provides a compound represented by the following Chemical Formula 1 or Chemical Formula 2:

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 2]

[0017]

[0018] In the above Chemical Formulas 1 and 2,

[0019] Ar is substituted or unsubstituted C 6-60 Aryl,

[0020] One of R1 to R6 is a substituent represented by the following Chemical Formula 3, and the others are each independently hydrogen or deuterium,

[0021] [Chemical Formula 3]

[0022]

[0023] In the above chemical formula 3,

[0024] L is a single bond; substituted or unsubstituted C 6-60 Arylene; or substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 Heteroarylene,

[0025] L1 and L2 are each independently a single bond; substituted or unsubstituted C 6-60 Arylene; or substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 Heteroarylene,

[0026] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 heteroaryl,

[0027] However, when R5 or R6 is a substituent represented by the above chemical formula 3,

[0028] L1 is substituted or unsubstituted C 6-60 Arylene, Ar1 is substituted or unsubstituted C 8-60 Aryl, or

[0029] L1 is a single bond; or substituted or unsubstituted C 6-60 Arylene, Ar1 is a substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 Heteroaryl.

[0030] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by Chemical Formula 1 or Chemical Formula 2.

[0031] Effects of the Invention

[0032] The compounds represented by Chemical Formula 1 or Chemical Formula 2 can be used as materials for the organic layer of an organic light-emitting device, thereby achieving improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device. In particular, the compounds represented by Chemical Formula 1 or Chemical Formula 2 can be used as materials for hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 The figure shows 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.

[0034] Figure 2 The diagram shows 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 . DETAILED DESCRIPTION

[0035] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0036] In this manual, It represents a bond to other substituents.

[0037] In the present specification, the term "substituted or unsubstituted" refers to a group 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 alkylthio group Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or a heterocyclic group containing one or more N, O, and S atoms, which may be substituted or unsubstituted with one or more substituents, or with a substituent formed by linking two or more of the substituents listed above. For example, a "substituent formed by linking two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group, or it may be interpreted as a substituent formed by linking two phenyl groups.

[0038] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0039]

[0040] In the present specification, 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, the ester group may be a group of the following structural formula, but is not limited thereto.

[0041]

[0042] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0043]

[0044] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0045] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0046] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0047] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-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, stilbene, and styryl, but are not limited thereto.

[0048] 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 cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0049] 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 carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0050] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.

[0051] etc. However, the present invention is not limited thereto.

[0052] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, etc., but are not limited thereto.

[0053] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine groups is the same as the examples of aryl groups described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the examples of alkyl groups described above. In this specification, the heteroaryl group in heteroarylamine is the same as the examples of heterocyclic groups described above. In this specification, the alkenyl group in aralkenyl groups is the same as the examples of alkenyl groups described above. In this specification, the description of aryl groups described above is applicable except that an arylene group is a divalent group. In this specification, the description of heterocyclic groups described above is applicable except that a heteroarylene group is a divalent group. In this specification, the description of heterocyclic groups described above is applicable except that a hydrocarbon ring is not a monovalent group but is formed by bonding two substituents. In this specification, the description of aryl or cycloalkyl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents. In this specification, the description of heterocyclic groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents.

[0054] In the above Chemical Formulas 1 and 2, one or more hydrogen atoms may be substituted with deuterium atoms.

[0055] Preferably, Ar is substituted or unsubstituted C 6-12 More preferably, Ar is phenyl, biphenyl or naphthyl.

[0056] Preferably, L is a single bond, or a substituted or unsubstituted C 6-12 More preferably, L is a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthylene, or -(phenylene)-(naphthylene)-. More preferably, L is a single bond, 1,4-phenylene, 4,4'-biphenyldiyl, or 2,6-naphthylene.

[0057] Preferably, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-12 Arylene. Preferably, L1 and L2 are each independently a single bond, a phenylene group, or a biphenyl diyl group. More preferably, L1 and L2 are each independently a single bond, a 1,4-phenylene group, or a 4,4'-biphenyl diyl group.

[0058] Preferably, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

[0059] Preferably, one of R1 to R4 is a substituent represented by the above Chemical Formula 3, and the others are each independently hydrogen or deuterium; and R5 and R6 are each independently hydrogen or deuterium.

[0060] Preferably, R1 to R4 are each independently hydrogen or deuterium; one of R5 and R6 is a substituent represented by the above Chemical Formula 3, and the rest are hydrogen or deuterium. Here, preferably, L1 is a phenylene group or a biphenyldiyl group, and Ar1 is a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a dimethylfluorenyl group, or a diphenylfluorenyl group; or L1 is a single bond, a phenylene group, or a biphenyldiyl group, and Ar1 is a dibenzofuranyl group, a dibenzothiophenyl group, a 9H-carbazole-9-yl group, or a 9-phenyl-9H-carbazole group. More preferably, Ar1 and Ar2 are each independently a terphenyl group, a naphthyl group, a phenanthryl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9H-carbazole-9-yl group, or a 9-phenyl-9H-carbazole group. Alternatively, preferably, Ar1 is a phenyl group, and Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, a dibenzothienyl group, a 9H-carbazole-9-yl group, or a 9-phenyl-9H-carbazole group; or Ar1 is a biphenyl group, and Ar2 is a terphenyl group, a phenanthryl group, a dibenzofuranyl group, a dibenzothienyl group, a 9H-carbazole-9-yl group, or a 9-phenyl-9H-carbazole group. Here, preferably, L1 and L2 are each independently a single bond, a phenylene group, or a biphenyldiyl group, and more preferably, L1 and L2 are each independently a single bond, a 1,4-phenylene group, or a 4,4'-biphenyldiyl group.

[0061] Representative examples of the compounds represented by the above Chemical Formula 1 or the above Chemical Formula 2 are shown below:

[0062]

[0063]

[0064]

[0065]

[0066]

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[0068]

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[0070]

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[0179] In addition, the present invention provides a method for producing a compound represented by the above Chemical Formula 1 wherein R1 is a compound represented by Chemical Formula 3 as shown in the following Reaction Formula 1. Other compounds represented by Chemical Formula 1 and compounds represented by Chemical Formula 2 can also be produced by similar methods.

[0180] [Reaction formula 1]

[0181]

[0182] In the above reaction formula 1, the remaining definitions except for X and Y are the same as those above, X is a halogen, preferably bromine or chlorine, Y is hydrogen when L is a single bond, and is -B(OH)2 when L is not a single bond. The above reaction formula 1 is an amine substitution reaction or a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base. The reactive groups used in each reaction can be changed according to techniques known in the art. The above production method can be further specified in the production examples described below.

[0183] The present invention also provides an organic light-emitting device comprising a compound represented by Chemical Formula 1 or Chemical Formula 2. As an example, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode disposed opposite the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by Chemical Formula 1 or Chemical Formula 2.

[0184] The organic layer of the organic light-emitting device of the present invention may be a single-layer structure or a multilayer structure comprising two or more organic layers. For example, the organic light-emitting device of the present invention may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include a smaller number of organic layers. The organic layer containing the aforementioned compound may also be an electron suppression layer.

[0185] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by the above Chemical Formula 1 or the above Chemical Formula 2. In particular, the compound according to the present invention may be used as a dopant for the light-emitting layer.

[0186] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1 or Chemical Formula 2.

[0187] In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons contains the compound represented by Chemical Formula 1 or Chemical Formula 2.

[0188] In addition, the organic layer includes a light-emitting layer and an electron transport layer, and the electron transport layer may include the compound represented by Chemical Formula 1 or Chemical Formula 2.

[0189] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and 2 .

[0190] Figure 1 The figure shows 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. In the above structure, the compound represented by the above Chemical Formula 1 or the above Chemical Formula 2 may be contained in the above light-emitting layer.

[0191] Figure 2 The figure shows 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. In the above structure, the compound represented by Chemical Formula 1 or Chemical Formula 2 may be contained in one or more of the hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0192] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1 or Chemical Formula 2. Furthermore, when the organic light-emitting device includes multiple organic layers, the organic layers can be formed of the same substance or different substances.

[0193] For example, an organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. An organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is then formed on the anode. A cathode material is then deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0194] Furthermore, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 or Chemical Formula 2 can be applied not only by vacuum evaporation but also by solution coating to form an organic layer. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spraying, and roller coating.

[0195] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0196] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0197] The anode material is preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, 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 SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0198] The cathode material is preferably one with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0199] The hole injection layer is a layer that injects holes from the electrode. As a hole injection material, it is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline, and polythiophene conductive polymers, but are not limited thereto.

[0200] The hole transport layer receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance capable of receiving holes from the anode or the hole injection layer and transferring them to the light-emitting layer. Suitable materials have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0201] The above-mentioned luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light range. It is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Azoles, benzothiazoles and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorenes, rubrene, etc., but are not limited thereto.

[0202] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

[0203] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0204] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with high electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. 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 common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, and in each case, they are accompanied by an aluminum layer or a silver layer.

[0205] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0206] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0207] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the materials used.

[0208] The preparation of the compound represented by the above Chemical Formula 1 or 2 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0209] [Manufacturing Example]

[0210] Preparation Example 1: Preparation of Compound AA

[0211]

[0212] Under a nitrogen atmosphere, 1-bromo-3-chloronaphthalene-2-amine (15 g, 58.5 mmol) and benzoyl chloride (9.9 g, 70.2 mmol) were added to chloroform (300 ml) and stirred. Then, pyridine (6.9 g, 87.7 mmol) was added dropwise. After reacting for 9 hours at room temperature, ethanol (600 ml) was added to solidify. After filtering the solid, it was redissolved in chloroform and washed with water twice. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.4 g of compound AA_P1. (Yield 83%, MS: [M+H] + =360)

[0213] Under a nitrogen atmosphere, compound AA_P1 (15 g, 41.6 mmol) and phosphorus pentasulfide (9.2 g, 41.6 mmol) were added to pyridine (150 ml), stirred, and refluxed. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer was distilled. The mixture was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.3 g of compound AA_P2. (Yield 53%, MS: [M+H]) + =376)

[0214] Under a nitrogen atmosphere, compound AA_P2 (15 g, 39.8 mmol) and potassium carbonate (16.5 g, 119.5 mmol) were added to DMF (150 ml), stirred and refluxed. Then, after sufficient stirring, copper iodide (0.1 g, 0.4 mmol) and 1,10-phenanthroline (0.1 g, 0.8 mmol) were added. After reacting for 11 hours, the mixture was cooled to room temperature and poured into water (300 ml) for solidification. After filtering the solid, it was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.8 g of compound AA. (Yield 75%, MS: [M+H] + =296)

[0215] Preparation Example 2: Preparation of Compound AB

[0216]

[0217] Compound AB was produced by the same method as in Production Example 1, except that 1-bromo-4-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0218] Preparation Example 3: Preparation of Compound AC

[0219]

[0220] Compound AC was produced by the same method as in Production Example 1, except that 1-bromo-5-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0221] Preparation Example 4: Preparation of Compound AD

[0222]

[0223] Compound AD was produced by the same method as in Production Example 1, except that 1-bromo-6-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0224] Preparation Example 5: Preparation of Compound AE

[0225]

[0226] Compound AE was produced by the same method as in Production Example 1, except that 1-bromo-7-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0227] Preparation Example 6: Preparation of Compound AF

[0228]

[0229] Compound AF was produced by the same method as in Production Example 1, except that 1-bromo-8-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0230] Preparation Example 7: Preparation of Compound AG

[0231]

[0232] Compound AG was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride.

[0233] Preparation Example 8: Preparation of Compound AH

[0234]

[0235] Compound AH was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-4-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0236] Preparation Example 9: Preparation of Compound AI

[0237]

[0238] Compound AI was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-5-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0239] Preparation Example 10: Preparation of Compound AJ

[0240]

[0241] Compound AJ was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-6-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0242] Preparation Example 11: Preparation of Compound AK

[0243]

[0244] Compound AK was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-7-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0245] Preparation Example 12: Preparation of Compound AL

[0246]

[0247] Compound AL was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-8-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0248] Preparation Example 13: Preparation of Compound AM

[0249]

[0250] Compound AM was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride.

[0251] Preparation Example 14: Preparation of Compound AN

[0252]

[0253] Compound AN was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-4-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0254] Preparation Example 15: Preparation of Compound AO

[0255]

[0256] Compound AO was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-5-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0257] Preparation Example 16: Preparation of Compound AP

[0258]

[0259] Compound AP was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-6-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0260] Preparation Example 17: Preparation of Compound AQ

[0261]

[0262] Compound AQ was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-7-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0263] Preparation Example 18: Preparation of Compound AR

[0264]

[0265] Compound AR was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-8-chloronaphthalene-2-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0266] Preparation Example 19: Preparation of Compound BA

[0267]

[0268] Compound BA was produced by the same method as in Production Example 1, except that 2-bromo-3-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0269] Preparation Example 20: Preparation of Compound BB

[0270]

[0271] Compound BB was produced by the same method as in Production Example 1, except that 2-bromo-4-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0272] Preparation Example 21: Preparation of Compound BC

[0273]

[0274] Compound BC was produced by the same method as in Production Example 1, except that 2-bromo-5-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0275] Preparation Example 22: Preparation of Compound BD

[0276]

[0277] Compound BD was produced by the same method as in Production Example 1, except that 2-bromo-6-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0278] Preparation Example 23: Preparation of Compound BE

[0279]

[0280] Compound BE was produced by the same method as in Production Example 1, except that 2-bromo-7-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0281] Preparation Example 24: Preparation of Compound BF

[0282]

[0283] Compound BF was produced by the same method as in Production Example 1, except that 2-bromo-8-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0284] Preparation Example 25: Preparation of Compound BG

[0285]

[0286] Compound BG was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-3-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0287] Preparation Example 26: Preparation of Compound BH

[0288]

[0289] Compound BH was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-4-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0290] Preparation Example 27: Preparation of Compound BI

[0291]

[0292] Compound BI was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0293] Preparation Example 28: Preparation of Compound BJ

[0294]

[0295] Compound BJ was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-6-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0296] Preparation Example 29: Preparation of Compound BK

[0297]

[0298] Compound BK was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-7-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0299] Preparation Example 30: Preparation of Compound BL

[0300]

[0301] Compound BL was produced by the same method as in Production Example 1, except that [1,1′-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-8-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0302] Preparation Example 31: Preparation of Compound BM

[0303]

[0304] Compound BM was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-3-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0305] Preparation Example 32: Preparation of Compound BN

[0306]

[0307] Compound BN was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-4-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0308] Preparation Example 33: Preparation of Compound BO

[0309]

[0310] Compound BO was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0311] Preparation Example 34: Preparation of Compound BP

[0312]

[0313] Compound BP was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-6-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0314] Preparation Example 35: Preparation of Compound BQ

[0315]

[0316] Compound BQ was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride, and 2-bromo-7-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0317] Preparation Example 36: Preparation of Compound BR

[0318]

[0319] Compound BR was produced by the same method as in Production Example 1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-8-chloronaphthalene-1-amine was used instead of 1-bromo-3-chloronaphthalene-2-amine.

[0320] [Example]

[0321] Example 1: Preparation of Compound 1

[0322]

[0323] Under a nitrogen atmosphere, compound AA (10 g, 33.8 mmol), compound amine 1 (15.1 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 1. (Yield 51%, MS: [M+H] + =707)

[0324] Example 2: Preparation of Compound 2

[0325]

[0326] Under a nitrogen atmosphere, compound AB (10 g, 33.8 mmol), compound amine 2 (12.2 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of compound 2. (Yield 50%, MS: [M+H] + =621)

[0327] Example 3: Preparation of Compound 3

[0328]

[0329] Under a nitrogen atmosphere, compound AC (10 g, 33.8 mmol), compound amine 3 (15.1 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 3. (Yield 55%, MS: [M+H] + =707)

[0330] Example 4: Preparation of Compound 4

[0331]

[0332] Under a nitrogen atmosphere, compound AF (10 g, 33.8 mmol), compound amine 4 (11.7 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 4. (Yield 55%, MS: [M+H] + =605)

[0333] Example 5: Preparation of Compound 5

[0334]

[0335] Under a nitrogen atmosphere, compound AE (10 g, 33.8 mmol), compound amine 5 (11.3 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 5. (Yield 52%, MS: [M+H] + =595)

[0336] Example 6: Preparation of Compound 6

[0337]

[0338] Under a nitrogen atmosphere, compound AE (10 g, 33.8 mmol), compound amine 6 (12.6 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of compound 6. (Yield 50%, MS: [M+H] + =631)

[0339] Example 7: Preparation of Compound 7

[0340]

[0341] Under a nitrogen atmosphere, compound AD (10 g, 33.8 mmol), compound amine 7 (10 g, 33.8 mmol), and sodium tert-butoxide (10.8 g, 50.7 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of compound 7. (Yield 53%, MS: [M+H] + =555)

[0342] Example 8: Preparation of Compound 8

[0343]

[0344] Under a nitrogen atmosphere, compound AA (15 g, 50.7 mmol) and compound amine 8 (24.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 8. (Yield 54%, MS: [M+H] + =671)

[0345] Example 9: Preparation of Compound 9

[0346]

[0347] Under a nitrogen atmosphere, compound AC (15 g, 50.7 mmol) and compound amine 9 (28.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.8 g of compound 9. (Yield 55%, MS: [M+H] + =746)

[0348] Example 10: Preparation of Compound 10

[0349]

[0350] Under a nitrogen atmosphere, compound AB (15 g, 50.7 mmol) and compound amine 10 (28.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.9 g of compound 10. (Yield 50%, MS: [M+H] + =746)

[0351] Example 11: Preparation of Compound 11

[0352]

[0353] Under a nitrogen atmosphere, compound AD (15 g, 50.7 mmol) and compound amine 11 (23.5 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound 11. (Yield 55%, MS: [M+H] + =657)

[0354] Example 12: Preparation of Compound 12

[0355]

[0356] Under a nitrogen atmosphere, compound AD (15 g, 50.7 mmol) and compound amine 12 (28.8 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.9 g of compound 12. (Yield 52%, MS: [M+H] + =757)

[0357] Example 13: Preparation of Compound 13

[0358]

[0359] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 13 (22.1 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.6 g of compound 13. (Yield 55%, MS: [M+H] + =632)

[0360] Example 14: Preparation of Compound 14

[0361]

[0362] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 14 (20.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6 g of compound 14. (Yield 55%, MS: [M+H] + =595)

[0363] Example 15: Preparation of Compound 15

[0364]

[0365] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 11 (23.5 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6 g of compound 15. (Yield 50%, MS: [M+H] + =657)

[0366] Example 16: Preparation of Compound 16

[0367]

[0368] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 15 (28.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.8 g of compound 16. (Yield 55%, MS: [M+H] + =746)

[0369] Example 17: Preparation of Compound 17

[0370]

[0371] Under a nitrogen atmosphere, compound AF (15 g, 50.7 mmol) and compound amine 16 (26.4 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 17. (Yield 51%, MS: [M+H] + =711)

[0372] Example 18: Preparation of Compound 18

[0373]

[0374] Under a nitrogen atmosphere, compound AA (15 g, 50.7 mmol) and compound amine 17 (31.5 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.5 g of compound 18. (Yield 55%, MS: [M+H] + =808)

[0375] Example 19: Preparation of Compound 19

[0376]

[0377] Under a nitrogen atmosphere, compound AB (15 g, 50.7 mmol) and compound amine 18 (34.3 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.2 g of compound 19. (Yield 51%, MS: [M+H] + =860)

[0378] Example 20: Preparation of Compound 20

[0379]

[0380] Under a nitrogen atmosphere, compound AD (15 g, 50.7 mmol) and compound amine 19 (23.5 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17 g of compound 20. (Yield 51%, MS: [M+H] + =657)

[0381] Example 21: Preparation of Compound 21

[0382]

[0383] Under a nitrogen atmosphere, compound AD (15 g, 50.7 mmol) and compound amine 20 (28.2 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 0.5 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.9 g of compound 21. (Yield 50%, MS: [M+H] + =784)

[0384] Example 22: Preparation of Compound 22

[0385]

[0386] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 21 (22.1 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 11 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 with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.9 g of compound 22. (Yield 53%, MS: [M+H] + = 631)

[0387] Example 23: Preparation of Compound 23

[0388]

[0389] Under a nitrogen atmosphere, compound AE (15 g, 50.7 mmol) and compound amine 22 (22.1 g, 53.2 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21 g, 152.1 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16 g of compound 23. (Yield 50%, MS: [M+H] + =631)

[0390] Example 24: Preparation of Compound 24

[0391]

[0392] Under a nitrogen atmosphere, compound AH (10 g, 26.9 mmol), compound amine 23 (10.7 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 24g. (Yield 53%, MS: [M+H] + =734)

[0393] Example 25: Preparation of Compound 25

[0394]

[0395] Under a nitrogen atmosphere, compound AJ (10 g, 26.9 mmol), compound amine 24 (12 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 25. (Yield 53%, MS: [M+H] + =784)

[0396] Example 26: Preparation of Compound 26

[0397]

[0398] Under a nitrogen atmosphere, compound AJ (10 g, 26.9 mmol), compound amine 25 (10 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 26. (Yield 51%, MS: [M+H] + =708)

[0399] Example 27: Preparation of Compound 27

[0400]

[0401] Under a nitrogen atmosphere, compound AK (10 g, 26.9 mmol), compound amine 26 (9.4 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 27. (Yield 52%, MS: [M+H] + =685)

[0402] Example 29: Preparation of Compound 29

[0403]

[0404] Under a nitrogen atmosphere, compound AK (15 g, 40.3 mmol) and compound amine 28 (15.5 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 29. (Yield 54%, MS: [M+H] + = 657)

[0405] Example 30: Preparation of Compound 30

[0406]

[0407] Under a nitrogen atmosphere, compound AG (15 g, 40.3 mmol) and compound amine 29 (24 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 30. (Yield 50%, MS: [M+H] + =859)

[0408] Example 31: Preparation of Compound 31

[0409]

[0410] Under a nitrogen atmosphere, compound AI (15 g, 40.3 mmol) and compound amine 30 (20.8 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.4 g of compound 31. (Yield 55%, MS: [M+H] + =783)

[0411] Example 32: Preparation of Compound 32

[0412]

[0413] Under a nitrogen atmosphere, compound AJ (15 g, 40.3 mmol) and compound amine 31 (21.9 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 32. (Yield 53%, MS: [M+H] + =809)

[0414] Example 33: Preparation of Compound 33

[0415]

[0416] Under a nitrogen atmosphere, compound AK (15 g, 40.3 mmol) and compound amine 32 (24 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.7 g of compound 33. (Yield 51%, MS: [M+H] + =859)

[0417] Example 34: Preparation of Compound 34

[0418]

[0419] Under a nitrogen atmosphere, compound AL (15 g, 40.3 mmol) and compound amine 33 (21.9 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 34. (Yield 53%, MS: [M+H] + =809)

[0420] Example 35: Preparation of Compound 35

[0421]

[0422] Under a nitrogen atmosphere, compound AI (15 g, 40.3 mmol) and compound amine 34 (21.4 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.1 g of compound 35. (Yield 50%, MS: [M+H] + = 797)

[0423] Example 37: Preparation of Compound 37

[0424]

[0425] Under a nitrogen atmosphere, compound AQ (10 g, 28.9 mmol), compound amine 36 (10.6 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of compound 37. (Yield 55%, MS: [M+H] + =675)

[0426] Example 38: Preparation of Compound 38

[0427]

[0428] Under a nitrogen atmosphere, compound AO (10 g, 28.9 mmol), compound amine 37 (12.9 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.6 g of compound 38. (Yield 53%, MS: [M+H]+ =757)

[0429] Example 39: Preparation of Compound 39

[0430]

[0431] Under a nitrogen atmosphere, compound AQ (10 g, 28.9 mmol), compound amine 38 (9.7 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 39. (Yield 52%, MS: [M+H] + =645)

[0432] Example 40: Preparation of Compound 40

[0433]

[0434] Under a nitrogen atmosphere, compound AN (15 g, 43.4 mmol) and compound amine 39 (23.6 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 40. (Yield 51%, MS: [M+H] + =783)

[0435] Example 41: Preparation of Compound 41

[0436]

[0437] Under a nitrogen atmosphere, compound AQ (15 g, 43.4 mmol) and compound amine 28 (16.6 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.7 g of compound 41. (Yield 50%, MS: [M+H] + =631)

[0438] Example 42: Preparation of Compound 42

[0439]

[0440] Under a nitrogen atmosphere, compound AR (15 g, 43.4 mmol) and compound amine 40 (20.1 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.5 g of compound 42. (Yield 54%, MS: [M+H] + =707)

[0441] Example 43: Preparation of Compound 43

[0442]

[0443] Under a nitrogen atmosphere, compound AP (15 g, 43.4 mmol) and compound amine 41 (26.5 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound 43. (Yield 51%, MS: [M+H] + =847)

[0444] Example 44: Preparation of Compound 44

[0445]

[0446] Under a nitrogen atmosphere, compound AQ (15 g, 43.4 mmol) and compound amine 42 (22.4 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.7 g of compound 44. (Yield 54%, MS: [M+H] + =757)

[0447] Example 45: Preparation of Compound 45

[0448]

[0449] Under a nitrogen atmosphere, compound AN (15 g, 43.4 mmol) and compound amine 43 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 45. (Yield 51%, MS: [M+H] + =834)

[0450] Example 46: Preparation of Compound 46

[0451]

[0452] Under a nitrogen atmosphere, compound AN (15 g, 43.4 mmol) and compound amine 44 (22.4 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 46. (Yield 51%, MS: [M+H] + =757)

[0453] Example 47: Preparation of Compound 47

[0454]

[0455] Under a nitrogen atmosphere, compound AQ (15 g, 43.4 mmol) and compound amine 45 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.1 g of compound 47. (Yield 53%, MS: [M+H] + =833)

[0456] Example 48: Preparation of Compound 48

[0457]

[0458] Under a nitrogen atmosphere, compound AO (15 g, 43.4 mmol) and compound amine 46 (18.9 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.6 g of compound 48. (Yield 53%, MS: [M+H] + =681)

[0459] Example 49: Preparation of Compound 49

[0460]

[0461] Under a nitrogen atmosphere, compound AP (15 g, 43.4 mmol) and compound amine 47 (22.4 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.7 g of compound 49. (Yield 54%, MS: [M+H] + =757)

[0462] Example 50: Preparation of Compound 50

[0463]

[0464] Under a nitrogen atmosphere, compound BA (10 g, 33.9 mmol), compound amine 48 (12.6 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.3 g of compound 50. (Yield 53%, MS: [M+H] + =631)

[0465] Example 51: Preparation of Compound 51

[0466]

[0467] Under a nitrogen atmosphere, compound BA (10 g, 33.9 mmol), compound amine 49 (13.5 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of compound 51. (Yield 50%, MS: [M+H] + =657)

[0468] Example 52: Preparation of Compound 52

[0469]

[0470] Under a nitrogen atmosphere, compound BC (10 g, 33.9 mmol), compound amine 50 (15.6 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 52. (Yield 50%, MS: [M+H] + =720)

[0471] Example 53: Preparation of Compound 53

[0472]

[0473] Under a nitrogen atmosphere, compound BB (10 g, 33.9 mmol), compound amine 51 (14.4 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 53. (Yield 55%, MS: [M+H]+ =684)

[0474] Example 54: Preparation of Compound 54

[0475]

[0476] Under a nitrogen atmosphere, compound BD (10 g, 33.9 mmol), compound amine 52 (15.2 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 54. (Yield 53%, MS: [M+H] + =707)

[0477] Example 55: Preparation of Compound 55

[0478]

[0479] Under a nitrogen atmosphere, compound BE (10 g, 33.9 mmol), compound amine 53 (13.5 g, 33.9 mmol), and sodium tert-butoxide (10.8 g, 50.8 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of compound 55. (Yield 50%, MS: [M+H] + =657)

[0480] Example 56: Preparation of Compound 56

[0481]

[0482] Under a nitrogen atmosphere, compound BA (15 g, 50.8 mmol) and compound amine 54 (25.7 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 56. (Yield 52%, MS: [M+H] + =698)

[0483] Example 57: Preparation of Compound 57

[0484]

[0485] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 55 (23.6 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18 g of compound 57. (Yield 54%, MS: [M+H] + =658)

[0486] Example 58: Preparation of Compound 58

[0487]

[0488] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 56 (25.2 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 58. (Yield 55%, MS: [M+H] + =687)

[0489] Example 59: Preparation of Compound 59

[0490]

[0491] Under a nitrogen atmosphere, compound BF (15 g, 50.8 mmol) and compound amine 57 (31 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound 59. (Yield 54%, MS: [M+H] + =796)

[0492] Example 60: Preparation of Compound 60

[0493]

[0494] Under a nitrogen atmosphere, compound BE (15 g, 50.8 mmol) and compound amine 58 (34.3 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound 60. (Yield 50%, MS: [M+H] + =859)

[0495] Example 61: Preparation of Compound 61

[0496]

[0497] Under a nitrogen atmosphere, compound BE (15 g, 50.8 mmol) and compound amine 59 (21.1 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.1 g of compound 61. (Yield 55%, MS: [M+H] + =611)

[0498] Example 62: Preparation of Compound 62

[0499]

[0500] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 60 (28.3 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 62. (Yield 52%, MS: [M+H] + =746)

[0501] Example 63: Preparation of Compound 63

[0502]

[0503] Under a nitrogen atmosphere, compound BE (15 g, 50.8 mmol) and compound amine 61 (22.2 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 63. (Yield 52%, MS: [M+H] + =631)

[0504] Example 64: Preparation of Compound 64

[0505]

[0506] Under a nitrogen atmosphere, compound BD (15 g, 50.8 mmol) and compound amine 62 (26.2 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Potassium carbonate (21.1 g, 152.5 mmol) was then dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 64. (Yield 53%, MS: [M+H] + =407)

[0507] Example 65: Preparation of Compound 65

[0508]

[0509] Under a nitrogen atmosphere, compound BD (15 g, 50.8 mmol) and compound amine 63 (21.6 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 65. (Yield 53%, MS: [M+H] + =621)

[0510] Example 66: Preparation of Compound 66

[0511]

[0512] Under a nitrogen atmosphere, compound BF (15 g, 50.8 mmol) and compound amine 64 (29.9 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 66. (Yield 50%, MS: [M+H] + =776)

[0513] Example 67: Preparation of Compound 67

[0514]

[0515] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 65 (30.3 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3 g of compound 67. (Yield 51%, MS: [M+H] + =783)

[0516] Example 68: Preparation of Compound 68

[0517]

[0518] Under a nitrogen atmosphere, compound BB (15 g, 50.8 mmol) and compound amine 66 (30.3 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 68. (Yield 54%, MS: [M+H] + =783)

[0519] Example 69: Preparation of Compound 69

[0520]

[0521] Under a nitrogen atmosphere, compound BB (15 g, 50.8 mmol) and compound amine 67 (27.6 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.5 g of compound 69. (Yield 55%, MS: [M+H] + =733)

[0522] Example 70: Preparation of Compound 70

[0523]

[0524] Under a nitrogen atmosphere, compound BF (15 g, 50.8 mmol) and compound amine 68 (28.9 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 70. (Yield 50%, MS: [M+H] + =757)

[0525] Example 71: Preparation of Compound 71

[0526]

[0527] Under a nitrogen atmosphere, compound BE (15 g, 50.8 mmol) and compound amine 69 (30.3 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 71. (Yield 54%, MS: [M+H] + =783)

[0528] Example 72: Preparation of Compound 72

[0529]

[0530] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 70 (24.8 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 72. (Yield 50%, MS: [M+H] + =681)

[0531] Example 73: Preparation of Compound 73

[0532]

[0533] Under a nitrogen atmosphere, compound BF (15 g, 50.8 mmol) and compound amine 71 (22.2 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 73. (Yield 52%, MS: [M+H] + =631)

[0534] Example 74: Preparation of Compound 74

[0535]

[0536] Under a nitrogen atmosphere, compound BC (15 g, 50.8 mmol) and compound amine 72 (37 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.1 g of compound 74. (Yield 50%, MS: [M+H] + =910)

[0537] Example 75: Preparation of Compound 75

[0538]

[0539] Under a nitrogen atmosphere, compound BD (15 g, 50.8 mmol) and compound amine 73 (34.4 g, 53.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in water (63 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.2 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24 g of compound 75. (Yield 55%, MS: [M+H] + =860)

[0540] Example 76: Preparation of Compound 76

[0541]

[0542] Under a nitrogen atmosphere, compound BG (10 g, 26.9 mmol), compound amine 74 (10 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 76. (Yield 55%, MS: [M+H] + =707)

[0543] Example 77: Preparation of Compound 77

[0544]

[0545] Under a nitrogen atmosphere, compound BI (10 g, 26.9 mmol), compound amine 75 (9 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of compound 77. (Yield 55%, MS: [M+H] + =671)

[0546] Example 78: Preparation of Compound 78

[0547]

[0548] Under a nitrogen atmosphere, compound BK (10 g, 26.9 mmol), compound amine 76 (11.3 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of compound 78. (Yield 53%, MS: [M+H] +=757)

[0549] Example 79: Preparation of Compound 79

[0550]

[0551] Under a nitrogen atmosphere, compound BJ (10 g, 26.9 mmol), compound amine 77 (10 g, 26.9 mmol), and sodium tert-butoxide (8.6 g, 40.3 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 79. (Yield 54%, MS: [M+H] + =708)

[0552] Example 80: Preparation of Compound 80

[0553]

[0554] Under a nitrogen atmosphere, compound BJ (15 g, 40.3 mmol) and compound amine 78 (15.5 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 80. (Yield 52%, MS: [M+H] + =657)

[0555] Example 81: Preparation of Compound 81

[0556]

[0557] Under a nitrogen atmosphere, compound BG (15 g, 40.3 mmol) and compound amine 79 (20.8 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 81. (Yield 53%, MS: [M+H] + =783)

[0558] Example 82: Preparation of Compound 82

[0559]

[0560] Under a nitrogen atmosphere, compound BG (15 g, 40.3 mmol) and compound amine 80 (20.8 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.1 g of compound 82. (Yield 51%, MS: [M+H] + =783)

[0561] Example 83: Preparation of Compound 83

[0562]

[0563] Under a nitrogen atmosphere, compound BI (15 g, 40.3 mmol) and compound amine 81 (25.1 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 83. (Yield 55%, MS: [M+H] + =889)

[0564] Example 84: Preparation of Compound 84

[0565]

[0566] Under a nitrogen atmosphere, compound BH (15 g, 40.3 mmol) and compound amine 82 (19.3 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.7 g of compound 84. (Yield 52%, MS: [M+H] + =747)

[0567] Example 85: Preparation of Compound 85

[0568]

[0569] Under a nitrogen atmosphere, compound BL (15 g, 40.3 mmol) and compound amine 83 (21.9 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 85. (Yield 53%, MS: [M+H] + =809)

[0570] Example 86: Preparation of Compound 86

[0571]

[0572] Under a nitrogen atmosphere, compound BI (15 g, 40.3 mmol) and compound amine 84 (21.4 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.4 g of compound 86. (Yield 51%, MS: [M+H] + =797)

[0573] Example 87: Preparation of Compound 87

[0574]

[0575] Under a nitrogen atmosphere, compound BG (15 g, 40.3 mmol) and compound amine 85 (22.5 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6 g of compound 87. (Yield 50%, MS: [M+H] + =823)

[0576] Example 88: Preparation of Compound 88

[0577]

[0578] Under a nitrogen atmosphere, compound BI (15 g, 40.3 mmol) and compound amine 86 (21.4 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.4 g of compound 88. (Yield 51%, MS: [M+H] + =797)

[0579] Example 89: Preparation of Compound 89

[0580]

[0581] Under a nitrogen atmosphere, compound BJ (15 g, 40.3 mmol) and compound amine 87 (19.7 g, 42.4 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (16.7 g, 121 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.5 g of compound 89. (Yield 54%, MS: [M+H] + =757)

[0582] Example 90: Preparation of Compound 90

[0583]

[0584] Under a nitrogen atmosphere, compound BN (10 g, 28.9 mmol), compound amine 88 (10.7 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2 g of compound 90. (Yield 52%, MS: [M+H] + =681)

[0585] Example 91: Preparation of Compound 91

[0586]

[0587] Under a nitrogen atmosphere, compound BM (10 g, 28.9 mmol), compound amine 89 (12.2 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of compound 91. (Yield 51%, MS: [M+H] + =731)

[0588] Example 92: Preparation of Compound 92

[0589]

[0590] Under a nitrogen atmosphere, compound BQ (10 g, 28.9 mmol), compound amine 90 (11.5 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 92. (Yield 51%, MS: [M+H] + =707)

[0591] Example 93: Preparation of Compound 93

[0592]

[0593] Under a nitrogen atmosphere, compound BP (10 g, 28.9 mmol), compound amine 91 (11.5 g, 28.9 mmol), and sodium tert-butoxide (9.2 g, 43.4 mmol) were added to xylene (200 ml), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, 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 with water twice, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.6 g of compound 93. (Yield 52%, MS: [M+H] +=707)

[0594] Example 94: Preparation of Compound 94

[0595]

[0596] Under a nitrogen atmosphere, compound BP (15 g, 43.4 mmol) and compound amine 92 (24.4 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 94. (Yield 53%, MS: [M+H] + =801)

[0597] Example 95: Preparation of Compound 95

[0598]

[0599] Under a nitrogen atmosphere, compound BP (15 g, 43.4 mmol) and compound amine 93 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 8 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18 g of compound 95. (Yield 50%, MS: [M+H] + =833)

[0600] Example 96: Preparation of Compound 96

[0601]

[0602] Under a nitrogen atmosphere, compound BN (15 g, 43.4 mmol) and compound amine 94 (24.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19 g of compound 96. (Yield 54%, MS: [M+H] + =811)

[0603] Example 97: Preparation of Compound 97

[0604]

[0605] Under a nitrogen atmosphere, compound BN (15 g, 43.4 mmol) and compound amine 95 (23 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 97. (Yield 50%, MS: [M+H] + =909)

[0606] Example 98: Preparation of Compound 98

[0607]

[0608] Under a nitrogen atmosphere, compound BR (15 g, 43.4 mmol) and compound amine 96 (20.1 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.3 g of compound 98. (Yield 50%, MS: [M+H] + =707)

[0609] Example 99: Preparation of Compound 99

[0610]

[0611] Under a nitrogen atmosphere, compound BP (15 g, 43.4 mmol) and compound amine 97 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 99. (Yield 54%, MS: [M+H] + =833)

[0612] Example 100: Preparation of Compound 100

[0613]

[0614] Under a nitrogen atmosphere, compound BN (15 g, 43.4 mmol) and compound amine 98 (23.6 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound 100. (Yield 55%, MS: [M+H] + =783)

[0615] Example 101: Preparation of Compound 101

[0616]

[0617] Under a nitrogen atmosphere, compound BM (15 g, 43.4 mmol) and compound amine 99 (23.6 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 12 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound 101. (Yield 55%, MS: [M+H] + =783)

[0618] Example 102: Preparation of Compound 102

[0619]

[0620] Under a nitrogen atmosphere, compound BP (15 g, 43.4 mmol) and compound amine 100 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.1 g of compound 102. (Yield 53%, MS: [M+H] + =833)

[0621] Example 103: Preparation of Compound 103

[0622]

[0623] Under a nitrogen atmosphere, compound BO (15 g, 43.4 mmol) and compound amine 101 (23 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 103. (Yield 55%, MS: [M+H] + =771)

[0624] Example 104: Preparation of Compound 104

[0625]

[0626] Under a nitrogen atmosphere, compound BO (15 g, 43.4 mmol) and compound amine 102 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 11 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.9 g of compound 104. (Yield 55%, MS: [M+H] + =833)

[0627] Example 105: Preparation of Compound 105

[0628]

[0629] Under a nitrogen atmosphere, compound BN (15 g, 43.4 mmol) and compound amine 103 (25.8 g, 45.5 mmol) were added to THF (300 ml), stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After reacting for 10 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 with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 105. (Yield 54%, MS: [M+H] + =833)

[0630] [Experimental example]

[0631] Experimental Example 1

[0632] ITO (indium tin oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0633] On the ITO transparent electrode prepared in this way, the following HI-1 compound was applied as The following A-1 compound was p-doped at a concentration of 1.5% to form a hole injection layer. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film with a thickness of Next, the compound 1 prepared above was vacuum-deposited on the hole transport layer to form a film having a thickness of On the electron suppression layer, the following RH-1 compound as the main body and the following Dp-7 compound as the dopant were vacuum-deposited at a weight ratio of 98:2 to form a film with a thickness of On the above-mentioned light-emitting layer, the following HB-1 compound was vacuum-deposited to form a film with a thickness of On the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form a film with a thickness of On the electron injection and transport layer, lithium fluoride (LiF) and The thickness of the aluminum A thickness of 1000 nm is evaporated to form a cathode.

[0634]

[0635] In the above process, the evaporation rate of organic matter is maintained at / second, the lithium fluoride at the cathode maintains / second evaporation speed, aluminum maintains The evaporation speed is 2x10 / s. During evaporation, the vacuum degree is maintained at 2x10 -7 ~5ⅹ10 -6 The organic light-emitting device is thus produced.

[0636] Experimental Examples 2 to 105

[0637] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds described in Tables 1 to 5 below were used instead of Compound 1.

[0638] Comparative Experimental Examples 1 to 16

[0639] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds listed in Table 6 below were used instead of Compound 1. Compounds C-1 to C-16 in Table 6 below are respectively as shown below.

[0640]

[0641] When current was applied to the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, the voltage and efficiency (15 mA / cm 2 ), and the results are shown in the following Tables 1 to 6. Lifespan T95 refers to the time (hr) required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0642] [Table 1]

[0643]

[0644] [Table 2]

[0645]

[0646] [Table 3]

[0647]

[0648] [Table 4]

[0649]

[0650] [Table 5]

[0651]

[0652] [Table 6]

[0653]

[0654] When current was applied to the organic light-emitting devices produced by Experimental Examples 1 to 105 and Comparative Experimental Examples 1 to 16, the results in Table 1 above were obtained. The red organic light-emitting device of Experimental Example 1 above used a substance that was widely used in the past and had a structure using Dp-7 as a dopant for the red light-emitting layer. In Comparative Examples 1 to 16, C-1 to C-16 were used instead of Compound 1 to produce organic light-emitting devices. From the results in Table 1 above, it can be seen that when the compound of the present invention is used for the electron suppression layer, the driving voltage is greatly reduced and the efficiency is also improved compared with the comparative example substance, which shows that the energy transfer from the host to the red dopant is well formed. In addition, it can be seen that while maintaining high efficiency, the life characteristics can also be greatly improved. It can be judged that this is ultimately due to the high stability of the compound of the present invention to electrons and holes compared with the comparative example compound. In summary, it can be confirmed that when the compound of the present invention is used for the electron suppression layer of the red light-emitting layer, the driving voltage, luminous efficiency and life characteristics of the organic light-emitting device can be improved.

[0655] [Explanation of symbols]

[0656] 1: Substrate 2: Anode

[0657] 3: Light-emitting layer 4: Cathode

[0658] 5: Hole injection layer 6: Hole transport layer

[0659] 7: Light-emitting layer 8: Electron transport layer.

Claims

1. A compound represented by the following chemical formula 1 or 2: Chemical formula 1 Chemical formula 2 In the chemical formulas 1 and 2, Ar is phenyl, biphenyl or naphthyl, One of R1 to R6 is a substituent represented by the following Chemical Formula 3, and the others are each independently hydrogen or deuterium, Chemical formula 3 In the chemical formula 3, L is a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthylene or -phenylene-naphthylene-, L1 and L2 are each independently a single bond, a phenylene group or a biphenyl diyl group, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl, Provided that, when R5 or R6 is a substituent represented by the chemical formula 3, L1 is phenylene or biphenyldiyl, Ar1 is biphenyl, naphthyl, or phenanthryl, or L1 is a single bond, and Ar1 is a dibenzofuranyl group, a dibenzothiophenyl group, a 9H-carbazol-9-yl group, or a 9-phenyl-9H-carbazolyl group.

2. The compound according to claim 1, wherein One of R1 to R4 is a substituent represented by Chemical Formula 3, and the others are each independently hydrogen or deuterium, R5 and R6 are each independently hydrogen or deuterium.

3. The compound according to claim 1, wherein R1 to R4 are each independently hydrogen or deuterium, One of R5 and R6 is a substituent represented by the chemical formula 3, and the others are hydrogen or deuterium.

4. The compound according to claim 3, wherein L1 is a phenylene group or a biphenyl diyl group, Ar1 is biphenyl, naphthyl or phenanthrenyl.

5. The compound according to claim 3, wherein L1 is a single bond, Ar1 is a dibenzofuranyl group, a dibenzothiophenyl group, a 9H-carbazol-9-yl group, or a 9-phenyl-9H-carbazolyl group.

6. A compound selected from the group consisting of:

7. An organic light-emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein: The organic layer containing the compound serves as an electron suppression layer.

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