Novel compounds and organic light emitting devices comprising the same

Abstract

The present application provides an organic light emitting device comprising a compound represented by Chemical Formula 1 in the light emitting layer and / or the electron blocking layer, and thus can improve the efficiency, driving voltage and / or lifespan characteristics.

Description

Technical Field

[0001] Cross-reference to related applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0041273, filed with the Korean Intellectual Property Office on March 30, 2021, and Korean Patent Application No. 10-2022-0039623, filed with the Korean Intellectual Property Office on March 30, 2022, the disclosures of which are incorporated herein by reference in their entirety.

[0003] This disclosure relates to novel compounds and organic light-emitting devices incorporating the same. Background Technology

[0004] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit characteristics such as wide viewing angle, excellent contrast, fast response time, and superior brightness, driving voltage, and response speed, and have therefore been the subject of much research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic material layer between the anode and cathode. The organic material layer often has a multilayer structure containing different materials to improve the efficiency and stability of the OLED. For example, the organic material layer can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of an OLED, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state.

[0006] There is a continued need to develop new organic materials for use in organic light-emitting devices as described above.

[0007] [Existing Technical Documents]

[0008] (Patent Document 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0009] Technical issues

[0010] This disclosure relates to novel compounds and organic light-emitting devices incorporating the same.

[0011] Technical solution

[0012] In this disclosure, compounds represented by the following chemical formula 1 are provided:

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] A1 is represented by the following chemical formula 1-a.

[0017] [Chemical Formula 1-a]

[0018]

[0019] In chemical formula 1-a,

[0020] The dashed line merges with the adjacent ring.

[0021] X is O or S.

[0022] Ar1 is C with or without substitution. 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 heteroaryl, and

[0023] A2 is a substituent represented by the following chemical formula 1-b; or the following chemical formula 1-c.

[0024] [Chemical Formula 1-b]

[0025]

[0026] [Chemical Formula 1-c]

[0027]

[0028] In chemical formulas 1-b and 1-c,

[0029] L1 to L4 are each a single bond; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 Hybrid aryl,

[0030] Ar2 through Ar5 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 Mixed aromatics,

[0031] D represents deuterium, and

[0032] n is an integer from 0 to 5.

[0033] In addition, an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains a compound represented by chemical formula 1.

[0034] Beneficial effects

[0035] Compounds represented by Formula 1 can be used as materials for organic material layers in organic light-emitting devices, and can improve the efficiency, low driving voltage, and / or lifetime of organic light-emitting devices. In particular, compounds represented by Formula 1 can be used as materials for hole injection, hole transport, hole injection and transport, electron blocking, light emission, electron transport, or electron injection. Attached Figure Description

[0036] Figure 1 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.

[0037] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4.

[0038] Figure 3 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 12, and a cathode 4. Detailed Implementation

[0039] In the following sections, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

[0040] In this disclosure, compounds represented by chemical formula 1 are provided.

[0041] As used in this article, symbols This refers to a bond that is connected to another substituent.

[0042] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group; aryl thio group; alkyl sulfonyl group; aryl sulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; arylenyl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphine group; and heterocyclic group containing at least one of N, O, and S atoms, or unsubstituted or substituted with two or more substituents linked together from the substituents exemplified above. For example, "substituents linked together with two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can also be interpreted as a substituent linked together with two phenyl groups.

[0043] In this disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably from 1 to 40. Specifically, the carbonyl group can be a group having the following structural formula, but is not limited thereto.

[0044]

[0045] In this disclosure, the ester group may have a structure in which the oxygen atom of the ester group is substituted by a straight-chain, 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 having the following structural formulas, but is not limited thereto.

[0046]

[0047] In this disclosure, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25.

[0048] Specifically, the imide group can be a group having the following structural formula, but is not limited thereto.

[0049]

[0050] In this disclosure, silane specifically includes, but is not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc.

[0051] In this disclosure, boron group specifically includes, but is not limited to, trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc.

[0052] Examples of halogen groups in this disclosure include fluorine, chlorine, bromine, or iodine.

[0053] In this disclosure, the alkyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbons. According to another embodiment, the alkyl group has 1 to 10 carbons. According to yet another embodiment, the alkyl group has 1 to 6 carbons. Specific examples of alkyl groups 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0054] In this disclosure, the alkenyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbons. According to another embodiment, the alkenyl group has 2 to 10 carbons. According to yet another embodiment, the alkenyl group has 2 to 6 carbons. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc.

[0055] In this disclosure, the cycloalkyl group is not particularly limited, but it is preferably composed of 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 yet 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, cyclooctyl, etc.

[0056] In this disclosure, the aryl group is not particularly limited, but it is preferably composed of 6 to 60 carbon atoms, and can be either a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0057] In this disclosure, the fluorene group can be substituted, and the two substituents can bond together to form a spirocyclic structure. When the fluorene group is substituted, a spirocyclic structure can be formed. However, the structure is not limited to this.

[0058] In this disclosure, the heterocyclic group is a heterocyclic group containing at least one heteroatom selected from O, N, Si, and S as a heteroelement, and its carbon number is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, and others. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolinel, iso Azolyl, thiadiazolyl, phenthiazinyl, dibenzofuranyl, etc., but not limited to these.

[0059] In this disclosure, the aryl group in aralkyl, arylenyl, alkylaryl, and arylamine is the same as the aforementioned examples of aryl. In this disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the aforementioned examples of alkyl. In this disclosure, the heteroaryl group in heteroarylamine can be described using the aforementioned description of heterocyclic groups. In this disclosure, the alkenyl group in arylenyl is the same as the aforementioned examples of alkenyl. In this disclosure, the aforementioned description of aryl can be applied, except that the arylene group is a divalent group. In this disclosure, the aforementioned description of heterocyclic groups can be applied, except that the heteroarylene group is a divalent group. In this disclosure, the aforementioned description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this disclosure, the aforementioned description of heterocyclic groups can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0060] Compounds represented by chemical formula 1 have benzo[…] The core consists of a azole or benzothiazole ring fused to a benzothiphene ring, and includes a triazine or amine substituent bonded thereto. Due to these structural properties, compounds represented by Formula 1 exhibit low voltage and excellent efficiency and lifetime when applied to organic light-emitting devices.

[0061] Chemical formula 1 can be specifically represented by any of the following chemical formulas 1-1 to 1-4:

[0062] [Chemical Formula 1-1]

[0063]

[0064] [Chemical Formula 1-2]

[0065]

[0066] [Chemical Formulas 1-3]

[0067]

[0068] [Chemical Formulas 1-4]

[0069]

[0070] In chemical formulas 1-1 to 1-4,

[0071] X, L1 to L4, Ar1 to Ar5, D and n are as defined in chemical formula 1.

[0072] Preferably, L1 and L2 are each independently a single bond; or substituted or unsubstituted C bonds. 6-20 arylene. More preferably, L1 and L2 are each independently a single bond; phenylene; biphenyl diyl; or naphthyl diyl.

[0073] Preferably, L3 and L4 are each independently a single bond; or substituted or unsubstituted C bonds. 6-20 arylene. More preferably, L3 and L4 are each independently a single bond; phenylene; biphenyl diyl; or naphthyl diyl.

[0074] Preferably, Ar1 is substituted or unsubstituted C. 6-20 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-20 Mixed aromatic compounds.

[0075] More preferably, Ar1 is phenyl; biphenyl; naphthyl; dibenzofuranyl; or dibenzothiophene.

[0076] Preferably, Ar2 to Ar5 are each independently substituted or unsubstituted C. 6-20aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-20 Mixed aromatic compounds.

[0077] Preferably, Ar2 and Ar3 are each independently phenyl; biphenyl; naphthyl; phenylnaphthyl (i.e., naphthyl substituted with one phenyl); naphthylphenyl (i.e., phenyl substituted with one naphthyl); phenanthrenephenyl (i.e., phenyl substituted with one phenanthrene); dibenzofuranyl; dibenzothiophenyl; or phenanthrene.

[0078] Preferably, Ar4 and Ar5 are each independently phenyl; biphenyl; terphenyl; naphthyl; naphthylphenyl; phenylnaphthyl; phenanthryl; 9-phenylcarbazolyl; dibenzofuranyl; or dibenzothiophene.

[0079] Furthermore, in the compound represented by Formula 1, at least one hydrogen atom may be substituted with deuterium. That is, n in Formula 1 may be an integer of 1 or greater, and / or at least one substituent of L1 to L4 and Ar1 to Ar5 in Formula 1 may be substituted with deuterium.

[0080] Representative examples of compounds represented by chemical formula 1 are as follows:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

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[0099]

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[0109]

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[0122]

[0123]

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[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] In addition, a method for preparing compounds represented by chemical formula 1 is provided.

[0164] For example, chemical formula 1 can be prepared by the preparation method as shown in reaction scheme 1 below.

[0165] [Reaction Scheme 1]

[0166]

[0167] In the above, the other substituents, except for X', are defined in the same way as in Formula 1, and X' is a halogen, preferably chlorine or bromine.

[0168] Reaction scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base. Furthermore, the reactive groups used in the Suzuki coupling reaction can be appropriately modified as is known in the art.

[0169] Alternatively, when A2 is formula 1-c and L2 is a single bond in formula 1, the compound of formula 1 can be prepared by the preparation method in reaction scheme 2 below.

[0170] [Reaction Scheme 2]

[0171]

[0172] In the above, the other substituents, except for X', are defined in the same way as in Formula 1, and X' is a halogen, preferably chlorine or bromine.

[0173] Reaction scheme 2 is an amine substitution reaction, and is preferably carried out in the presence of a palladium catalyst and a base. Furthermore, the reactive groups used in the amine substitution reaction can be appropriately modified as is known in the art.

[0174] The preparation method can be described in more detail in the following preparation examples.

[0175] Furthermore, an organic light-emitting device comprising a compound represented by Chemical Formula 1 is provided. As an example, such an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1.

[0176] The organic material layer of the organic light-emitting device disclosed herein can have a single-layer structure, or it can have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of this disclosure can have a structure that includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it may include a small number of organic material layers.

[0177] Furthermore, the organic material layer may include a light-emitting layer, and the light-emitting layer comprises a compound represented by Chemical Formula 1. In particular, the compound according to this disclosure may be used as the host of the light-emitting layer.

[0178] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer contains a compound represented by chemical formula 1.

[0179] Furthermore, the organic light-emitting device according to this disclosure can be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to this disclosure can be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of this disclosure is shown below. Figures 1 to 3 middle.

[0180] Figure 1 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4. In such a structure, a compound represented by chemical formula 1 can be included in the light-emitting layer.

[0181] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4. In such a structure, a compound represented by chemical formula 1 may be contained in at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer.

[0182] Figure 3 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 12, and a cathode 4. In such a structure, a compound represented by chemical formula 1 may be contained in at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, and electron injection and transport layer. For example, it may be contained in either the light-emitting layer or the electron blocking layer.

[0183] Organic light-emitting devices according to this disclosure can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer comprises a compound represented by chemical formula 1. Furthermore, when the organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed from the same material or different materials.

[0184] For example, the organic light-emitting device according to this disclosure can be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode; and then depositing a material that can be used as a cathode on the organic material layer. Besides this method, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0185] Furthermore, in the fabrication of organic light-emitting devices, compounds represented by chemical formula 1 can be formed into organic material layers through solution coating and vacuum deposition methods. In this paper, solution coating methods refer to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but are not limited to these.

[0186] In addition to this method, organic light-emitting devices can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the fabrication method is not limited to this.

[0187] For example, the first electrode is the anode and the second electrode is the cathode, or alternatively, the first electrode is the cathode and the second electrode is the anode.

[0188] As an anode material, materials with a high work function are generally preferred, allowing holes to be smoothly injected into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0189] As cathode materials, materials with low work functions are generally preferred, allowing electrons to be easily injected into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0190] A hole injection layer is a layer used to inject holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, thus exhibiting an effect of injecting holes into the anode and an excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and having excellent ability to form thin films. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0191] Furthermore, the hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. Suitable hole transport materials are those with high hole mobility, capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0192] Electron blocking layers are used to improve the efficiency of organic light-emitting devices by preventing electrons injected from the cathode from being transferred to the anode and recombine in the light-emitting layer. Materials with electron affinities lower than those of electron transport layers are preferably used for electron blocking layers. Preferably, the materials represented by Chemical Formula 1 of this disclosure can be used as electron blocking materials.

[0193] Luminescent materials are suitable for emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, and exhibiting good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0194] Furthermore, the light-emitting layer may comprise a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic compound. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. In particular, compounds represented by Formula 1 can be used as the host material of the light-emitting layer in this disclosure, and in this case, low voltage, high efficiency, and / or long lifetime of organic light-emitting devices can be achieved.

[0195] Specifically, in Formula 1, when A2 is a triazine substituent represented by Formula 1-b, it is suitable as an N-type host material, and when A2 is an amine substituent represented by Formula 1-c, it is suitable as a P-type host material. Therefore, in Formula 1, at least one compound in which A2 is a triazine substituent represented by Formula 1-b and at least one compound in which A2 is an amine substituent represented by Formula 1-c can be simultaneously included in the luminescent layer.

[0196] Dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives with aryl amino groups, either substituted or unsubstituted, and examples include pyrene, anthracene, etc., which contain aryl amino groups. Diindrone pyrene, etc. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0197] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material used is suitably one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and possesses a high electron mobility. Specifically, examples may include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the relevant art. In particular, suitable examples of cathode materials are typical materials with low work functions, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0198] An electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that possesses the ability to transport electrons, the effect of injecting electrons from the cathode, and an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation capabilities. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0199] Examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium.

[0200] According to one embodiment of this disclosure, electron transport materials and electron injection materials can be deposited simultaneously to form an electron injection and transport layer as a single layer.

[0201] The organic light-emitting device according to this disclosure can be a bottom-emitting device, a top-emitting device, or a dual-sided emitting device, and in particular, the organic light-emitting device can be a bottom-emitting device that requires relatively high luminous efficiency.

[0202] In addition to organic light-emitting devices, compounds represented by chemical formula 1 can also be included in organic solar cells or organic transistors.

[0203] The following examples will describe in detail the preparation of compounds represented by Formula 1 and organic light-emitting devices comprising them. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of this disclosure.

[0204] [Example]

[0205] <Preparation Example: Preparation of the nucleus of a compound of chemical formula 1>

[0206] (Synthetic schemes for preparation examples 1 to 4)

[0207]

[0208] Preparation Example 1: Synthesis of Chemical Formula AA

[0209]

[0210] 2-Amino-6-bromophenol (15 g, 79.8 mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (17 g, 83.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (33.1 g, 239.3 mmol) was then dissolved in 99 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.1 g of chemical formula AA_P1 (yield 76%, MS: [M+H]+=266).

[0211] Under a nitrogen atmosphere, 15 g (56.6 mmol) of AA_P1 and 3.8 g (113.2 mmol) were added to 300 mL of acetic acid, and the mixture was stirred and refluxed. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic layer was distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8 g of AA_P2 (74% yield, MS: [M+H]+ = 282).

[0212] AA_P2 (15 g, 53.2 mmol) and trifluoromethanesulfonic acid (12 g, 79.9 mmol) were added to 300 mL of pyridine under a nitrogen atmosphere and stirred at room temperature. After reacting for 11 hours, the mixture was poured into 600 mL of water for coagulation and then filtered. The mixture was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.2 g of AA_P3 (62% yield, MS: [M+H]+ = 250).

[0213] Under a nitrogen atmosphere, AA_P3 (15 g, 60.2 mmol), carbon disulfide (5.5 g, 72 mmol), and potassium hydroxide (4.1 g, 77 mmol) were added to 150 mL of EtOH, and the mixture was stirred and refluxed. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic solvent was distilled under reduced pressure. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.9 g of AA_P4 (64% yield, MS: [M+H]+ = 258).

[0214] AA_P4 (15 g, 58.4 mmol) and phosphorus pentachloride (12.2 g, 70 mmol) were added to 150 mL of toluene under a nitrogen atmosphere, and the mixture was stirred and refluxed. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic solvent was distilled under reduced pressure. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.1 g of AA (yield 67%, MS: [M+H]+=260).

[0215] Preparation Example 2: Synthesis of Chemical Formula AB

[0216]

[0217] Chemical formula AB was prepared in the same manner as in Preparation Example 1, except that (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0218] Preparation Example 3: Synthesis of Chemical Formula AC

[0219]

[0220] Chemical formula AC was prepared in the same manner as in Preparation Example 1, except that (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0221] Preparation Example 4: Synthesis of chemical formula AD

[0222]

[0223] The chemical formula AD was prepared in the same manner as in Preparation Example 1, except that (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0224] (Synthetic schemes for preparation examples 5 and 6)

[0225]

[0226] Preparation Example 5: Synthesis of Chemical Formula AE

[0227]

[0228] Chemical formula AE was prepared in the same manner as in Preparation Example 1, except that 2-amino-6-bromo-4-chlorophenol was used instead of 2-amino-6-bromophenol, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0229] Preparation Example 6: Synthesis of Chemical Formula AF

[0230]

[0231] Chemical formula AE was prepared in the same manner as in Preparation Example 1, except that 2-amino-6-bromo-3-chlorophenol was used instead of 2-amino-6-bromophenol, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0232] (Synthetic schemes for preparation examples 7 to 10)

[0233]

[0234] Preparation Example 7: Synthesis of Chemical Formula BA

[0235]

[0236] Chemical formula BA was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromophenol was used instead of 2-amino-6-bromophenol.

[0237] Preparation Example 8: Synthesis of Chemical Formula BB

[0238]

[0239] Chemical formula BB was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromophenol was used instead of 2-amino-6-bromophenol, and (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0240] Preparation Example 9: Synthesis of Chemical Formula BC

[0241]

[0242] Chemical formula BC was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromophenol was used instead of 2-amino-6-bromophenol, and (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0243] Preparation Example 10: Synthesis of Chemical Formula BD

[0244]

[0245] Chemical formula BD was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromophenol was used instead of 2-amino-6-bromophenol, and (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0246] (Synthetic schemes for preparation examples 11 to 12)

[0247]

[0248] Preparation Example 11: Synthesis of Chemical Formula BE

[0249]

[0250] Chemical formula BE was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromo-5-chlorophenol was used instead of 2-amino-6-bromophenol, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0251] Preparation Example 12: Synthesis of chemical formula BF

[0252]

[0253] Chemical formula BF was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromo-6-chlorophenol was used instead of 2-amino-6-bromophenol, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0254] (Synthetic schemes for preparation examples 13 to 16)

[0255]

[0256] Preparation Example 13: Synthesis of Chemical Formula CA

[0257]

[0258] 3-Bromo-2-fluoroaniline (15 g, 78.9 mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (24 g, 118.4 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (32.7 g, 236.8 mmol) was then dissolved in 98 mL of water and added to the mixture. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.8 g of the chemical formula CA_P1 (yield 51%, MS: [M+H]+=268).

[0259] Under a nitrogen atmosphere, 15 g (56.2 mmol) of the chemical formula CA_P1 and 2.9 g (84.3 mmol) of hydrogen peroxide were added to 300 mL of acetic acid, and the mixture was stirred and refluxed. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic layer was distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.6 g of the chemical formula CA_P2 (yield 54%, MS: [M+H]+=284).

[0260] Under a nitrogen atmosphere, 15 g (53 mmol) of CA_P2 and 11.9 g (79.5 mmol) of trifluoromethanesulfonic acid were added to 300 mL of pyridine and stirred at room temperature. After 11 hours of reaction, the mixture was poured into 600 mL of water for coagulation and then filtered. The mixture was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.9 g of CA_P3 (yield 52%, MS: [M+H]+=252).

[0261] Under a nitrogen atmosphere, 15 g (59.7 mmol) of the chemical formula CA_P3 and 21.0 g (131 mmol) of potassium dithiocarbonate O-ethyl ester were added to 150 mL of DMF, and the mixture was stirred and refluxed. After reacting for 9 hours, the mixture was cooled to room temperature, and the organic solvent was distilled under reduced pressure. The solvent was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g of the chemical formula CA_P4 (80% yield, MS: [M+H]+=308).

[0262] Under a nitrogen atmosphere, 15 g (48.7 mmol) of the chemical formula CA_P4 was added to 150 mL of CHCl3 and cooled to 0 °C in an ice bath. Then, thionyl chloride (12.8 g, 107.5 mmol) was slowly added dropwise with stirring. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic solvent was distilled under reduced pressure. The solvent was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g of the chemical formula CA (68% yield, MS: [M+H]+=310).

[0263] Preparation Example 14: Synthesis of Chemical Formula CB

[0264]

[0265] Chemical formula CB was prepared in the same manner as in Preparation Example 13, except that (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0266] Preparation Example 15: Synthesis of Chemical Formula CC

[0267]

[0268] The chemical formula CC was prepared in the same manner as in Preparation Example 13, except that (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0269] Preparation Example 16: Synthesis of Chemical Formula CD

[0270]

[0271] The chemical formula CD was prepared in the same manner as in Preparation Example 13, except that (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0272] (Synthetic schemes for preparation examples 17 to 18)

[0273]

[0274] Preparation Example 17: Synthesis of Chemical Formula CE

[0275]

[0276] Chemical formula CE was prepared in the same manner as in Preparation Example 13, except that 3-bromo-5-chloro-2-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0277] Preparation Example 18: Synthesis of Chemical Formula CF

[0278]

[0279] Chemical formula CF was prepared in the same manner as in Preparation Example 13, except that 3-bromo-6-chloro-2-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0280] (Synthetic schemes for preparation examples 19 to 22)

[0281]

[0282] Preparation Example 19: Synthesis of Chemical Formula DA

[0283]

[0284] Chemical formula DA was prepared in the same manner as in Preparation Example 13, except that 2-bromo-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline.

[0285] Preparation Example 20: Synthesis of Chemical Formula DB

[0286]

[0287] Chemical formula DB was prepared in the same manner as in Preparation Example 13, except that 2-bromo-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0288] Preparation Example 21: Synthesis of DC (Chemical Formula)

[0289]

[0290] The chemical formula DC was prepared in the same manner as in Preparation Example 13, except that 2-bromo-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0291] Preparation Example 22: Synthesis of Chemical Formula DD

[0292]

[0293] Chemical formula DD was prepared in the same manner as in Preparation Example 13, except that 2-bromo-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0294] (Synthetic schemes for preparation examples 23 to 24)

[0295]

[0296] Preparation Example 23: Synthesis of Chemical Formula DE

[0297]

[0298] Chemical formula DE was prepared in the same manner as in Preparation Example 13, except that 2-bromo-4-chloro-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0299] Preparation Example 24: Synthesis of Chemical Formula DF

[0300]

[0301] Chemical formula DF was prepared in the same manner as in Preparation Example 13, except that 6-bromo-3-chloro-2-fluoroaniline was used instead of 3-bromo-2-fluoroaniline, and (2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

[0302] <Synthetic Example: Preparation of Compounds of Formula 1>

[0303] Synthesis example 1-1

[0304]

[0305] Under a nitrogen atmosphere, AA (15 g, 51 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.6 g, 53.5 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of subAA-1 (61% yield, MS: [M+H]+ = 412).

[0306] Under a nitrogen atmosphere, subAA-1 (15 g, 36.4 mmol) and bis(pinacol)diboron (10.2 g, 40.1 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in alkane. Potassium acetate (5.4 g, 54.6 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After 7 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g subAA-2 (yield 63%, MS: [M+H]+=504).

[0307] SubAA-2 (15 g, 29.8 mmol) and Trz1 (9.9 g, 31.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.4 mmol) was then dissolved in 37 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7 g of compound 1-1 (70% yield, MS: [M+H]+ = 659).

[0308] Synthesis example 1-2

[0309]

[0310] Chemical compound AB (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.6 g subAB-1 (yield 56%, MS: [M+H]+=336).

[0311] Under a nitrogen atmosphere, subAB-1 (15 g, 44.7 mmol) and bis(pinacol)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in alkane. Potassium acetate (6.6 g, 67 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After 6 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.6 g subAB-2 (yield 66%, MS: [M+H]+ = 428).

[0312] SubAB-2 (15 g, 35.1 mmol) and Trz2 (9.9 g, 36.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12 g of compound 1-2 (yield 64%, MS: [M+H]+=533).

[0313] Synthesis Example 1-3

[0314]

[0315] AE (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.4 g subAE-1 (yield 55%, MS: [M+H]+ = 336).

[0316] Under a nitrogen atmosphere, subAE-1 (15 g, 44.7 mmol) and Trz3 (22.5 g, 46.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20 g of compound 1-3 (yield 61%, MS: [M+H]+ = 735).

[0317] Synthesis Example 1-4

[0318]

[0319] Under a nitrogen atmosphere, subAE-1 (15 g, 44.7 mmol) and Trz4 (20.8 g, 46.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compounds 1-4 (yield 54%, MS: [M+H]+ = 699).

[0320] Synthesis Example 1-5

[0321]

[0322] Chemical compound AF (15 g, 51 mmol) and naphthyl-2-ylboronic acid (9.2 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.5 g subAF-1 (yield 69%, MS: [M+H]+ = 386).

[0323] SubAF-1 (15 g, 38.9 mmol) and Trz5 (16.5 g, 40.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to prepare 18.2 g of compounds 1-5 (66% yield, MS: [M+H]+ = 709).

[0324] Synthesis Example 1-6

[0325]

[0326] BA (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8 g subBA-1 (69% yield, MS: [M+H]+ = 336).

[0327] Under a nitrogen atmosphere, subBA-1 (15 g, 44.7 mmol) and bis(pinacol)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in alkane. Potassium acetate (6.6 g, 67 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g subBA-2 (78% yield, MS: [M+H]+ = 428).

[0328] SubBA-2 (15 g, 35.1 mmol) and Trz6 (14.5 g, 36.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to prepare 13.6 g of compounds 1-6 (yield 59%, MS: [M+H]+ = 659).

[0329] Synthesis Example 1-7

[0330]

[0331] BB (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g subBB-1 (60% yield, MS: [M+H]+ = 336).

[0332] SubBB-1 (15 g, 44.7 mmol) and Trz7 (18.9 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to prepare 17.9 g of compounds 1-7 (yield 61%, MS: [M+H]+ = 659).

[0333] Synthesis Example 1-8

[0334]

[0335] BE (15 g, 51 mmol) and dibenzo[b,d]thiophene-1-ylboronic acid (12.2 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.7 g subBE-1 (yield 52%, MS: [M+H]+ = 442).

[0336] Under a nitrogen atmosphere, subBE-1 (15 g, 33.9 mmol) and Trz8 (14.4 g, 35.6 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (14.1 g, 101.8 mmol) was then dissolved in 42 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to prepare 14.8 g of compounds 1-8 (yield 57%, MS: [M+H]+ = 765).

[0337] Synthesis Example 1-9

[0338]

[0339] BF (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g subBF-1 (66% yield, MS: [M+H]+ = 336).

[0340] SubBF-1 (15 g, 44.7 mmol) and Trz9 (22.5 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to prepare 16.7 g of compounds 1-9 (yield 51%, MS: [M+H]+ = 735).

[0341] Synthesis Example 1-10

[0342]

[0343] Under a nitrogen atmosphere, CA (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.3 g subCA-1 (yield 55%, MS: [M+H]+=352).

[0344] Under a nitrogen atmosphere, subCA-1 (15 g, 42.6 mmol) and Trz10 (19.2 g, 44.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.6 g of compound 1-10 (69% yield, MS: [M+H]+=701).

[0345] Synthesis Example 1-11

[0346]

[0347] CB (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.2 g subCB-1 (yield 54%, MS: [M+H]+ = 352).

[0348] Under a nitrogen atmosphere, subCB-1 (15 g, 42.6 mmol) and bis(pinacol)diboron (11.9 g, 46.9 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in alkane. Potassium acetate (6.3 g, 63.9 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.7 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.6 mmol). After 5 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g subCB-2 (75% yield, MS: [M+H]+ = 444).

[0349] SubCB-2 (15 g, 33.8 mmol) and Trz11 (14 g, 35.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14 g, 101.5 mmol) was then dissolved in 42 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound 1-11 (yield 58%, MS: [M+H]+ = 675).

[0350] Synthesis Example 1-12

[0351]

[0352] SubCB-1 (15 g, 42.6 mmol) and Trz12 (18 g, 44.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.8 g of compound 1-12 (yield 55%, MS: [M+H]+ = 675).

[0353] Synthesis Example 1-13

[0354]

[0355] Under a nitrogen atmosphere, CE (15 g, 48.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (10.8 g, 50.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g subCE-1 (yield 58%, MS: [M+H]+ = 442).

[0356] Under a nitrogen atmosphere, subCE-1 (15 g, 33.9 mmol) and Trz13 (12.6 g, 35.6 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (14.1 g, 101.8 mmol) was then dissolved in 42 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5 g of compound 1-13 (64% yield, MS: [M+H]+=715).

[0357] Synthesis Example 1-14

[0358]

[0359] Chemical compound CF (15 g, 48.4 mmol) and naphthalene-2-ylboronic acid (10.8 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13 g subCF-1 (67% yield, MS: [M+H]+=402).

[0360] Under a nitrogen atmosphere, subCF-1 (15 g, 37.3 mmol) and Trz5 (15.8 g, 39.2 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (15.5 g, 112 mmol) was then dissolved in 46 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.4 g of compound 1-14 (68% yield, MS: [M+H]+ = 725).

[0361] Synthesis Example 1-15

[0362]

[0363] Under a nitrogen atmosphere, DA (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.7 g subDA-1 (69% yield, MS: [M+H]+ = 352).

[0364] Under a nitrogen atmosphere, subDA-1 (15 g, 42.6 mmol) and bis(pinacol)diboron (11.9 g, 46.9 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in an alkane. Potassium acetate (6.3 g, 63.9 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.7 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.6 mmol). After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g subDA-2 (78% yield, MS: [M+H]+ = 444).

[0365] Under a nitrogen atmosphere, subDA-2 (15 g, 33.8 mmol) and Trz14 (14 g, 35.5 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (14 g, 101.5 mmol) was then dissolved in 42 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.7 g of compound 1-15 (69% yield, MS: [M+H]+ = 675).

[0366] Synthesis Example 1-16

[0367]

[0368] Under a nitrogen atmosphere, 15 g (48.4 mmol) of chemical formula DB and 10.8 g (50.8 mmol) of naphthyl-2-ylboronic acid were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.9 g of subDB-1 (yield 51%, MS: [M+H]+=402).

[0369] Under a nitrogen atmosphere, subDB-1 (15 g, 37.3 mmol) and bis(pinacol)diboron (10.4 g, 41.1 mmol) were added to 300 ml of 1,4-dioxanone. The mixture was stirred and refluxed in alkane. Potassium acetate (5.5 g, 56 mmol) was then added and stirred thoroughly, followed by bis(dibenzylacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After 7 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.3 g subDB-2 (yield 67%, MS: [M+H]+ = 494).

[0370] SubDB-2 (15 g, 30.4 mmol) and Trz2 (8.5 g, 31.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.6 g, 91.2 mmol) was then dissolved in 38 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of compound 1-16 (64% yield, MS: [M+H]+ = 599).

[0371] Synthesis Example 1-17

[0372]

[0373] DF (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g subDF-1 (yield 53%, MS: [M+H]+ = 352).

[0374] Under a nitrogen atmosphere, subDF-1 (15 g, 42.6 mmol) and Trz15 (18 g, 44.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.5 g of compound 1-17 (68% yield, MS: [M+H]+ = 675).

[0375] Synthesis example 2-1

[0376]

[0377] Under a nitrogen atmosphere, AA (15 g, 51 mmol) and naphthyl-2-ylboronic acid (9.2 g, 53.5 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g subAA-3 (yield 57%, MS: [M+H]+ = 386).

[0378] Under a nitrogen atmosphere, subAA-3 (10 g, 25.9 mmol), amine 1 (8.7 g, 25.9 mmol), and sodium tert-butoxide (8.3 g, 38.9 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.6 g of compound 2-1 (yield 54%, MS: [M+H]+=685).

[0379] Synthesis example 2-2

[0380]

[0381] Under a nitrogen atmosphere, subAB-1 (10 g, 29.8 mmol), amine 2 (8.8 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.6 g of compound 2-2 (yield 54%, MS: [M+H]+=595).

[0382] Synthesis example 2-3

[0383]

[0384] AC (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.4 g subAC-1 (yield 55%, MS: [M+H]+ = 336).

[0385] Under a nitrogen atmosphere, subAC-1 (10 g, 29.8 mmol), amine 3 (12.2 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of compound 2-3 (yield 53%, MS: [M+H]+=710).

[0386] Synthesis example 2-4

[0387]

[0388] SubAC-1 (15 g, 44.7 mmol) and amine 4 (22.8 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.5 g of compound 2-4 (50% yield, MS: [M+H]+ = 741).

[0389] Synthesis example 2-5

[0390]

[0391] AE (15 g, 51 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.6 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g subAE-2 (yield 53%, MS: [M+H]+ = 412).

[0392] Under a nitrogen atmosphere, subAE-2 (10 g, 24.3 mmol), amine 5 (7.2 g, 24.3 mmol), and sodium tert-butoxide (7.7 g, 36.4 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.9 g of compound 2-5 (yield 55%, MS: [M+H]+ = 671).

[0393] Synthesis example 2-6

[0394]

[0395] Chemical compound AF (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g subAF-2 (yield 66%, MS: [M+H]+ = 336).

[0396] SubAF-2 (15 g, 44.7 mmol) and amine 6 (20.7 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compound 2-6 (yield 54%, MS: [M+H]+ = 697).

[0397] Synthesis example 2-7

[0398]

[0399] SubBA-1 (15 g, 44.7 mmol) and amine 7 (18.5 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 2-7 (yield 59%, MS: [M+H]+ = 651).

[0400] Synthesis example 2-8

[0401]

[0402] SubBB-1 (15 g, 44.7 mmol) and amine 8 (23 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22 g of compound 2-8 (66% yield, MS: [M+H]+ = 747).

[0403] Synthesis example 2-9

[0404]

[0405] Under a nitrogen atmosphere, subBB-1 (10 g, 29.8 mmol), amine 9 (12.6 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.4 g of compound 2-9 (yield 53%, MS: [M+H]+=724).

[0406] Synthesis example 2-10

[0407]

[0408] 15 g (51 mmol) of chemical formula BC and 9.2 g (53.5 mmol) of naphthyl-2-ylboronic acid were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7 g subBC-1 (70% yield, MS: [M+H]+ = 386).

[0409] Under a nitrogen atmosphere, subBC-1 (10 g, 25.9 mmol), amine 10 (8.3 g, 25.9 mmol), and sodium tert-butoxide (8.3 g, 38.9 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of compound 2-10 (yield 52%, MS: [M+H]+ = 671).

[0410] Synthesis example 2-11

[0411]

[0412] 15 g (51 mmol) of BC and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g subBC-2 (60% yield, MS: [M+H]+ = 336).

[0413] SubBC-2 (15 g, 44.7 mmol) and amine 11 (17.8 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.4 g of compound 2-11 (yield 51%, MS: [M+H]+ = 635).

[0414] Synthesis example 2-12

[0415]

[0416] 15 g (51 mmol) of BC and 11.4 g (53.5 mmol) of dibenzo[b,d]furan-1-ylboronic acid were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g subBC-3 (66% yield, MS: [M+H]+ = 426).

[0417] SubBC-3 (15 g, 35.2 mmol) and amine 12 (16.3 g, 37 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.7 mmol) was then dissolved in 44 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.1 g of compound 2-12 (69% yield, MS: [M+H]+ = 787).

[0418] Synthesis example 2-13

[0419]

[0420] BE (15 g, 51 mmol) and phenylboronic acid (6.5 g, 53.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.5 g subBE-2 (50% yield, MS: [M+H]+ = 336).

[0421] Under a nitrogen atmosphere, subBE-2 (10 g, 29.8 mmol), amine 13 (10.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g of compound 2-13 (60% yield, MS: [M+H]+ = 645).

[0422] Synthesis example 2-14

[0423]

[0424] SubBE-2 (15 g, 44.7 mmol) and amine 14 (21.4 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.3 g of compound 2-14 (64% yield, MS: [M+H]+ = 711).

[0425] Synthesis example 2-15

[0426]

[0427] SubBF-1 (15 g, 44.7 mmol) and amine 15 (22.1 g, 46.9 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.8 g of compound 2-15 (yield 55%, MS: [M+H]+ = 727).

[0428] Synthesis example 2-16

[0429]

[0430] Under a nitrogen atmosphere, 15 g (48.4 mmol) of the chemical formula CA and 11.6 g (50.8 mmol) of dibenzo[b,d]thiophene-3-ylboronic acid were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g subCA-2 (yield 51%, MS: [M+H]+ = 458).

[0431] SubCA-2 (15 g, 32.8 mmol) and amine 16 (14.3 g, 34.4 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (13.6 g, 98.3 mmol) was then dissolved in 41 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g of compound 2-16 (yield 55%, MS: [M+H]+ = 793).

[0432] Synthesis example 2-17

[0433]

[0434] Under a nitrogen atmosphere, subCB-1 (10 g, 28.4 mmol), amine 17 (12 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound 2-17 (yield 63%, MS: [M+H]+=737).

[0435] Synthesis example 2-18

[0436]

[0437] SubCB-1 (15 g, 42.6 mmol) and amine 18 (21.1 g, 44.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18 g of compound 2-18 (yield 57%, MS: [M+H]+ = 743).

[0438] Synthesis example 2-19

[0439]

[0440] Under a nitrogen atmosphere, 15 g (48.4 mmol) of compound CC and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.7 g subCC-1 (yield 51%, MS: [M+H]+=352).

[0441] Under a nitrogen atmosphere, subCC-1 (10 g, 28.4 mmol), amine 19 (11.7 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound 2-19 (65% yield, MS: [M+H]+ = 727).

[0442] Synthesis example 2-20

[0443]

[0444] Under a nitrogen atmosphere, subCC-1 (10 g, 28.4 mmol), amine 20 (10.6 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.3 g of compound 2-20 (yield 63%, MS: [M+H]+=687).

[0445] Synthesis example 2-21

[0446]

[0447] SubCC-1 (15 g, 42.6 mmol) and amine 21 (22 g, 44.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.1 g of compound 2-21 (65% yield, MS: [M+H]+ = 763).

[0448] Synthesis example 2-22

[0449]

[0450] Chemical compound CD (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.7 g subCD-1 (yield 51%, MS: [M+H]+=352).

[0451] SubCD-1 (15 g, 42.6 mmol) and amine 22 (19.8 g, 44.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of compound 2-22 (yield 57%, MS: [M+H]+=713).

[0452] Synthesis example 2-23

[0453]

[0454] Chemical compound CE (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g subCE-2 (yield 66%, MS: [M+H]+=352).

[0455] Under a nitrogen atmosphere, subCE-2 (10 g, 28.4 mmol), amine 23 (9.8 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of compound 2-23 (yield 59%, MS: [M+H]+ = 661).

[0456] Synthesis example 2-24

[0457]

[0458] Chemical compound CF (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.8 g subCF-2 (yield 58%, MS: [M+H]+=352).

[0459] Under a nitrogen atmosphere, subCF-2 (10 g, 28.4 mmol), amine 24 (10 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.2 g of compound 2-24 (yield 54%, MS: [M+H]+ = 667).

[0460] Synthesis example 2-25

[0461]

[0462] SubDB-1 (15 g, 37.3 mmol) and amine 25 (17.3 g, 39.2 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.5 g, 112 mmol) was then dissolved in 46 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.8 g of compound 2-25 (yield 52%, MS: [M+H]+ = 763).

[0463] Synthesis example 2-26

[0464]

[0465] Under a nitrogen atmosphere, 15 g (48.4 mmol) of chemical formula DB and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (20 g, 145.1 mmol) was dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g subDB-2 (yield 66%, MS: [M+H]+=352).

[0466] Under a nitrogen atmosphere, subDB-2 (10 g, 29.8 mmol), amine 26 (12.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.4 g of compound 2-26 (yield 54%, MS: [M+H]+=711).

[0467] Synthesis example 2-27

[0468]

[0469] Under a nitrogen atmosphere, 15 g (48.4 mmol) of chemical formula DC and 8.7 g (50.8 mmol) of naphthyl-2-ylboronic acid were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (20 g, 145.1 mmol) was dissolved in 60 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of subDC-1 (yield 57%, MS: [M+H]+=402).

[0470] Under a nitrogen atmosphere, subDC-1 (10 g, 24.9 mmol), amine 10 (8 g, 24.9 mmol), and sodium tert-butoxide (7.9 g, 37.3 mmol) were added to 200 mL of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. Subsequently, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.7 g of compound 2-27 (yield 51%, MS: [M+H]+=687).

[0471] Synthesis example 2-28

[0472]

[0473] DC (15 g, 48.4 mmol) and phenylboronic acid (6.2 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g subDC-2 (yield 53%, MS: [M+H]+=352).

[0474] SubDC-2 (15 g, 42.6 mmol) and amine 27 (21 g, 44.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (17.7 g, 127.9 mmol) was then dissolved in 53 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.1 g of compound 2-28 (70% yield, MS: [M+H]+ = 741).

[0475] Synthesis example 2-29

[0476]

[0477] DE (15 g, 48.4 mmol) and dibenzo[b,d]furan-2-ylboronic acid (10.8 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9 g subDE-1 (yield 56%, MS: [M+H]+ = 442).

[0478] SubDE-1 (15 g, 33.9 mmol) and amine 28 (17.5 g, 35.6 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.1 g, 101.8 mmol) was then dissolved in 42 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 2-29 (yield 59%, MS: [M+H]+ = 853).

[0479] Synthesis example 2-30

[0480]

[0481] DF (15 g, 48.4 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.1 g, 50.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (20 g, 145.1 mmol) was then dissolved in 60 mL of water and added to the solution. The mixture was then stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.5 g subDF-2 (yield 51%, MS: [M+H]+ = 428).

[0482] SubDF-2 (15 g, 35.1 mmol) and amine 29 (18.1 g, 36.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.5 g, 105.2 mmol) was then dissolved in 44 mL of water and added to the solution. The mixture was then stirred thoroughly, and bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved again in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of compound 2-30 (yield 59%, MS: [M+H]+ = 839).

[0483] <Examples and Comparative Examples>

[0484] Comparative Example A

[0485] It is coated with a thickness of The ITO (indium tin oxide) glass substrate, used as the thin film, was immersed in distilled water containing a cleaning agent and ultrasonically cleaned. A product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes each time with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropanol, acetone, and methanol solvents, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum deposition apparatus.

[0486] On the prepared ITO transparent electrode, the following compound HI-1 is formed to... The thickness is such that compound A-1 is p-doped at a concentration of 1.5% to form a hole injection layer. On the hole injection layer, compound HT-1 is vacuum-deposited to form a thickness of [thickness value missing]. A hole transport layer. Then, on the hole transport layer, the following compound EB-1 is vacuum deposited to form a thickness. An electron blocking layer was then formed. Next, on the film deposited with EB-1, compounds RH-1 and Dp-7 were vacuum deposited at a weight ratio of 98:2 to form a thickness of [thickness missing]. A red luminescent layer. On the luminescent layer, the following compound HB-1 is vacuum-deposited to form a thickness of [thickness missing]. A hole-blocking layer. On the hole-blocking layer, compounds ET-1 and LiQ are vacuum-deposited at a weight ratio of 2:1 to form a thickness of [thickness missing]. Electron injection and transport layers. Lithium fluoride (LiF) and aluminum (Al) are sequentially deposited onto the electron injection and transport layers. and The thickness is used to form the cathode.

[0487]

[0488] In the above process, the deposition rate of organic materials is maintained at to Maintain the deposition rate of lithium fluoride on the cathode at And keep the aluminum deposition rate at In addition, the vacuum level during deposition was maintained at 2×10⁻⁶. -7 Up to 5×10 -6 This led to the creation of organic light-emitting devices.

[0489] Examples 1 to 17

[0490] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 1 was used instead of compound RH-1, which was the main component in the organic light-emitting device of Comparative Example A.

[0491] Comparative Examples 1 to 7

[0492] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compounds shown in Table 1 were used instead of compound RH-1, which was the main component in the organic light-emitting device of Comparative Example A. Compounds B-8 to B-14 are listed in Table 1 below.

[0493] Examples 18 to 47

[0494] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 2 was used as the electron blocking layer material instead of compound EB-1 in the organic light-emitting device of Comparative Example A.

[0495] Comparative Examples 8 to 14

[0496] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compounds shown in Table 2 were used as electron blocking layer materials instead of compound EB-1 in the organic light-emitting device of Comparative Example A. The compounds B-1 to B-7 listed in Table 2 are as follows.

[0497] Examples 48 to 119

[0498] The organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the first and second main bodies described in Table 3 were used in a 1:1 weight ratio instead of compound RH-1, which was the main body in the organic light-emitting device of Comparative Example A.

[0499]

[0500] <Experimental Example>

[0501] For the organic light-emitting devices prepared in Examples 1 to 119, Comparative Example A, and Comparative Examples 1 to 14, by applying a current (15 mA / cm²) 2 The voltage, efficiency, and lifetime were measured, and the results are shown in Tables 1 to 3 below. Lifetime (T95) refers to the time it takes for the initial brightness (7,000 nits) to decrease to 95%.

[0502] [Table 1]

[0503]

[0504] [Table 2]

[0505]

[0506]

[0507] [Table 3]

[0508]

[0509]

[0510]

[0511] When an electric current was applied to the organic light-emitting devices manufactured according to Examples 1 to 119 and Comparative Examples 1 to 14, the results shown in Tables 1 to 3 were obtained.

[0512] When compounds 1-1 to 1-17 of this disclosure are used as the red body, it is determined that the driving voltage is reduced and the efficiency and lifetime are increased compared to the case where the compounds of the comparative examples shown in Table 1 are used. Furthermore, when compounds 2-1 to 2-30 of this disclosure are used as the electron blocking layer, it is determined that the driving voltage is reduced and the efficiency and lifetime are increased compared to the case where the compounds of the comparative examples shown in Table 2 are used.

[0513] In Table 3, when one of compounds 1-1 to 1-17 is selected as the first host and one of compounds 2-1 to 2-30 is selected as the second host, and they are co-deposited and used as the red host, it is determined that the driving voltage is reduced and the efficiency and lifetime are increased compared with the case of using a single material host.

[0514] The results in Tables 1 to 3 show that when compounds of Formula 1 are used as the host material for the red emitting layer or the electron blocking layer material in red devices, the driving voltage, luminous efficiency, and lifetime of organic light-emitting devices can be improved.

[0515] [Explanation of reference numerals in the attached figures]

[0516] 1: Substrate 2: Anode

[0517] 3: Organic material layer; 4: Cathode

[0518] 5: Hole injection layer; 6: Hole transport layer

[0519] 7: Electron blocking layer; 8: Emissive layer

[0520] 9: Hole blocking layer 10: Electron transport layer

[0521] 11: Electron injection layer 12: Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In chemical formula 1, A1 is represented by the following chemical formula 1-a. [Chemical Formula 1-a] In chemical formula 1-a, The dashed line merges with the adjacent ring. X is O or S. Ar1 is unsubstituted C 6-20 aryl; or unsubstituted C containing at least one heteroatom selected from O and S. 2-20 heteroaryl, and A2 is a substituent represented by the following chemical formula 1-b; or the following chemical formula 1-c. [Chemical Formula 1-b] [Chemical Formula 1-c] In chemical formulas 1-b and 1-c, L1 through L4 are each independently a single bond or an unreplaced C bond. 6-20 Alpha-aryl Ar2 to Ar5 are each independently defined by C. 6-20 Aryl-substituted or unsubstituted C 6-20 aryl; or C 6-20 Aryl-substituted or unsubstituted C containing at least one heteroatom selected from N, O and S 2-20 Mixed aromatics, D represents deuterium, and n is an integer from 0 to 5.

2. The compound according to claim 1, The chemical formula 1 therein is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-1 to 1-4, X, L1 to L4, Ar1 to Ar5, D and n are as defined in claim 1.

3. The compound according to claim 1, L1 and L2 are each independently a single bond; phenylene; biphenyl dimethyl; or naphthyl dimethyl.

4. The compound according to claim 1, Ar1 is phenyl; biphenyl; naphthyl; dibenzofuranyl; or dibenzothiophene.

5. The compound according to claim 1, Ar2 and Ar3 are each independently phenyl; biphenyl; naphthyl; phenylnaphthyl; naphthylphenyl; dibenzofuranyl; dibenzothiophene; or phenanthryl.

6. The compound according to claim 1, L3 and L4 are each independently a single bond; phenylene; biphenyl dimethyl; or naphthyl dimethyl.

7. The compound according to claim 1, Ar4 and Ar5 are each independently phenyl; biphenyl; terphenyl; naphthyl; naphthylphenyl; phenylnaphthyl; phenanthryl; 9-phenylcarbazolyl; dibenzofuranyl; or dibenzothiophene.

8. A compound selected from any of the following: 。 9. An organic light-emitting device, comprising: First electrode; The second electrode is configured to be opposite to the first electrode; And one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 8.

10. The organic light-emitting device according to claim 9, The organic material layer containing the compound is a light-emitting layer and / or an electron-blocking layer.

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