Novel compounds and organic light emitting devices comprising the same

Abstract

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

Description

TECHNICAL FIELD

[0001] Cross Reference to Related Applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0020508, filed February 16, 2021, and Korean Patent Application No. 10-2022-0020090, filed February 16, 2022, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein in their entireties by reference.

[0003] The present disclosure relates to a novel compound and an organic light emitting device comprising the same. BACKGROUND

[0004] In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using organic material. An organic light emitting device utilizing the organic light emitting phenomenon has characteristics such as a wide viewing angle, an excellent contrast, a fast response time, an excellent luminance, a driving voltage and a response speed, and thus has been extensively researched.

[0005] An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multi-layer structure including different materials to enhance the efficiency and stability of the organic light emitting device, for example, the organic material layer can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light emitting device, 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, and excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to a ground state again.

[0006] There is a continuous need to develop new materials for organic materials used in the organic light emitting device as described above.

[0007] [Prior Art Document]

[0008] [Patent Document]

[0009] (Patent Document 1) Korean Unexamined Patent Publication No. 10-2000-0051826 SUMMARY

[0010] TECHNICAL PROBLEM

[0011] An object of the present disclosure is to provide a novel organic light emitting material and an organic light emitting device comprising the same.

[0012] TECHNICAL SOLUTION

[0013] According to one aspect of the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0014] [Chemical Formula 1]

[0015]

[0016] In Chemical Formula 1,

[0017] R1to R 12 any one of which is a substituent represented by the following Chemical Formula 2, and the rest are each independently hydrogen or deuterium,

[0018] [Chemical Formula 2]

[0019]

[0020] In Chemical Formula 2,

[0021] L1is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenyldiyl, a substituted or unsubstituted naphthalenediyl, or

[0022] L2and L3are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene comprising at least one selected from N, O, and S,

[0023] Ar1is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl, and

[0024] Ar2is biphenyl, terphenyl, naphthyl, phenanthryl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, dimethylfluorenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0025] According to another aspect of the present disclosure, there is provided an organic light emitting device including: 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 one or more of the organic material layers comprises a compound represented by Chemical Formula 1.

[0026] Advantageous Effects

[0027] The above-described compound represented by Chemical Formula 1 can be used as a material for an organic material layer of an organic light emitting device, and can improve efficiency, achieve a low driving voltage, and / or improve a lifespan characteristic in an organic light emitting device. In particular, the above-described compound represented by Chemical Formula 1 can be used as a light emitting material. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, an electron blocking layer 3, a light emitting layer 4, and a cathode 5 is shown.

[0029] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron blocking layer 3, a light emitting layer 4, a hole blocking layer 8, an electron transport and injection layer 9, and a cathode 5 is shown. DETAILED DESCRIPTION

[0030] Hereinafter, embodiments of the present disclosure will be described in more detail in order to facilitate the understanding of the present application.

[0031] Provided herein are compounds represented by Chemical Formula 1.

[0032] As used herein, the symbol or means a bond to another substituent.

[0033] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; an oxidized phosphonic group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; and a heteroaryl group including at least one of N, O, and S atom, or a substituent substituted with two or more substituents bonded to each other from among the above exemplified substituents. For example, "a substituent substituted with two or more substituents bonded to each other" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or it can also be interpreted as a substituent in which two phenyl groups are bonded to each other.

[0034] In the present disclosure, the number of carbons of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group can be a substituent having the following structural formula, but is not limited thereto.

[0035]

[0036] In the present disclosure, the ester group can have a structure in which the oxygen of the ester group can be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group can be a substituent having the following structural formula, but is not limited thereto.

[0037]

[0038] In the present disclosure, the number of carbons of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group can be a substituent having the following structural formula, but is not limited thereto.

[0039]

[0040] In the present disclosure, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto.

[0041] In the present disclosure, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.

[0042] In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0043] In the present disclosure, the alkyl group can be linear or branched, and the number of carbons thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbons of the alkyl group is 1 to 20. According to another embodiment, the number of carbons of the alkyl group is 1 to 10. According to another embodiment, the number of carbons of the alkyl group is 1 to 6. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a t-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, an n-octyl group, a t-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an iso-hexyl group, a 2-methylpentyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but is not limited thereto.

[0044] 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.

[0045] 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.

[0046] 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. As a monocyclic aryl group, the aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0047] In this disclosure, the fluorene group can be substituted, and two substituents can be linked 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.

[0048] In this disclosure, a heteroaryl group is a heteroaryl group containing at least one of O, N, Si, and S as a heteroatom, and its carbon number is not particularly limited, but is preferably 2 to 60. According to one exemplary embodiment of the heteroaryl group, the heteroaryl group has 6 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thiopheneyl, furanyl, pyrroleyl, 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.

[0049] In this disclosure, the aryl group in aralkyl, arylenyl, alkylaryl, and arylamine is the same as the aryl group described above. In this disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the alkyl group described above. In this disclosure, the heteroaryl group in heteroarylamine can be applied to the above description of heteroaryl. In this disclosure, the alkenyl group in arylenyl is the same as the alkenyl group described above. In this disclosure, the above description of aryl can be applied, except that the arylene group is a divalent group. In this disclosure, the above description of heteroaryl can be applied, except that the heteroarylene group is a divalent group. In this disclosure, the above 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 above description of heteroaryl can be applied, except that the heteroaryl is not a monovalent group but is formed by combining two substituents.

[0050] Preferably, R1 to R3, R5 to R9, R 11 and R 12 Any one of them is a substituent represented by chemical formula 2, and the others are each independently hydrogen or deuterium, as well as R4 and R 10 Each can be either hydrogen or deuterium independently. More preferably, R1 to R3, R5 to R9, R 11 and R 12 Any one of them can be a substituent represented by chemical formula 2, the rest are each independently hydrogen, and R4 and R 10 Each can be hydrogen independently.

[0051] Preferably, L1 can be an unsubstituted or monophenyl-substituted phenylene, an unsubstituted or monophenyl-substituted biphenyldiyl, or an unsubstituted or monophenyl-substituted naphthyl, or

[0052] More preferably, L1 can be selected from any of the following:

[0053]

[0054] More preferably, L1 can be an unsubstituted or monophenyl-substituted phenylene, an unsubstituted or monophenyl-substituted biphenyldiyl, or a naphthyldiyl.

[0055] More preferably, L1 can be selected from any of the following:

[0056]

[0057] More preferably, R5 or R 11 The substituent is represented by chemical formula 2, and L1 can be selected from any of the following:

[0058]

[0059] Preferably, L2 and L3 can each be a single bond independently; substituted or unsubstituted C 6-20 Aromatic; or substituted or unsubstituted C containing at least one of N, O and S. 2-20 Hybrid aryl.

[0060] More preferably, L2 and L3 can each be independently a single bond, a phenylene, a phenylene substituted with one phenyl group, a biphenyl diyl, a biphenyl diyl substituted with one phenyl group, or a naphthyl diyl.

[0061] Most preferably, L2 and L3 can each be a single bond independently or selected from any of the following:

[0062]

[0063] Preferably, Ar1 can be substituted or unsubstituted C. 6-20 aryl, or substituted or unsubstituted C containing at least one of N, O and S. 2-20 Mixed aromatic compounds.

[0064] More preferably, Ar1 can be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, phenylnaphthyl, dibenzofuranyl, dibenzothiophene, phenylcarbazoyl, dimethylfluorenyl, benzonaphthiophene, or benzonaphthiophene.

[0065] More preferably, Ar1 can be selected from any of the following:

[0066]

[0067] More preferably, Ar1 can be selected from any of the following:

[0068]

[0069] Preferably, Ar2 can be selected from any of the following:

[0070]

[0071] Representative examples of compounds represented by chemical formula 1 are as follows:

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[0171] As an example, compounds represented by chemical formula 1 (where R1 to R...) 12Any one of them is a substituent represented by the following chemical formula 2, and the remainder is hydrogen) can be prepared by the preparation method shown in reaction scheme 1 below, and the other remaining compounds can be prepared in a similar manner.

[0172] [Reaction Scheme 1]

[0173]

[0174] In reaction scheme 1, L1 to L3, Ar1 and Ar2 are defined as in chemical formula 1, X is a halogen, and preferably, X is chlorine or bromine.

[0175] Reaction scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used in the Suzuki coupling reaction can be modified as known in the art. The above preparation method can be further illustrated in the preparation examples described below.

[0176] In another embodiment of this disclosure, an organic light-emitting device comprising a compound represented by Chemical Formula 1 is provided. In one example, this disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more layers of organic material comprise a compound represented by Chemical Formula 1.

[0177] 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 can include fewer organic material layers.

[0178] In addition, the organic material layer may include a light-emitting layer, wherein the light-emitting layer may contain a compound represented by chemical formula 1.

[0179] In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer for simultaneously performing hole transport and injection, wherein the hole transport layer, the hole injection layer, or the layer for simultaneously performing hole transport and injection may contain a compound represented by chemical formula 1.

[0180] In addition, the organic material layer may include an electron injection layer, an electron transport layer, or an electron transport and injection layer, wherein the electron injection layer, electron transport layer, or electron transport and injection layer may contain a compound represented by chemical formula 1.

[0181] 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. Figure 1 and Figure 2 middle.

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

[0183] The organic light-emitting device according to this disclosure can be manufactured using materials and methods known in the art, except that at least one of the organic material layers 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 a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer on the anode including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, 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, spraying, roll coating, etc., but are not limited to these.

[0186] In addition to this method, organic light-emitting devices can 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] As an 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 anode materials, materials with a large 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 compounds, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0189] As cathode materials, materials with a small work function 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 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 also exhibiting excellent ability to form thin films. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of 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] A hole transport layer is a layer that receives holes from a hole injection layer and transports them to a light-emitting layer. Suitable materials for the hole transport layer 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. Preferably, compounds represented by Formula 1 can be used as materials for the hole transport layer.

[0192] An electron blocking layer is a layer disposed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the hole transport layer and recombining in the light-emitting layer; it can also be called an electron suppression layer. The electron blocking layer is preferably made of a material with a lower electron affinity than the electron transport layer. Preferably, a compound represented by chemical formula 1 can be used as the material for the electron blocking layer.

[0193] Luminescent materials are preferably those capable of receiving holes and electrons transported from the hole transport layer and electron transport layer, respectively, and combining the holes and electrons to emit light in the visible light region, while exhibiting good quantum efficiency for fluorescence or phosphorescence. Specific examples of luminescent materials 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] The organic light-emitting layer may comprise a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, etc. 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. Preferably, compounds represented by Formula 1 may be included as the host material.

[0195] Examples of dopant materials include aromatic amine derivatives, styrylamine 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., with aryl amino groups. Diindrone pyrene, etc. Styrenicoamine 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, styrenicoamines, styrenicodiamines, styrenicotriamines, styrenicotetraamines, etc. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0196] Preferably, the dopant material can be selected from at least one of the following:

[0197]

[0198]

[0199]

[0200] A hole blocking layer is a layer placed between the electron transport layer and the light-emitting layer to prevent holes injected from the anode from transferring to the electron transport layer and recombining in the light-emitting layer; it can also be called a hole suppression layer. The hole blocking layer is preferably made of a material with a large ionization energy.

[0201] The electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material 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. Specific examples of electron transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes including Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, etc. 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 a small work function, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0202] 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 of electron injection layers 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.

[0203] 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.

[0204] On the other hand, in this disclosure, the “electron transport and injection layer” is a layer that serves as both an electron injection layer and an electron transport layer, and the materials that serve the functions of each layer can be used alone or in combination, and are not limited thereto.

[0205] The organic light-emitting device according to this disclosure can be a bottom-emitting device, a top-emitting device, or a dual-sided light-emitting device, and in particular, it can be a bottom-emitting device that requires relatively high luminous efficiency.

[0206] In addition to organic light-emitting devices, compounds represented by chemical formula 1 can be included in organic solar cells or organic transistors.

[0207] The preparation of compounds represented by Formula 1 and organic light-emitting devices comprising them will be described in detail by way of examples. However, the following examples are for illustrative purposes only, and the scope of this disclosure is not limited thereto.

[0208] [Preparation Example]

[0209] Preparation Example 1

[0210]

[0211] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 1 (34 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.1 g of compound 1. (Yield: 68%, MS: [M+H)) + =750)

[0212] Preparation Example 2

[0213]

[0214] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 2 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31 g of compound 2. (Yield: 75%, MS: [M+H)) + =724)

[0215] Preparation Example 3

[0216]

[0217] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 3 (24.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 3. (Yield: 74%, MS: [M+H)) + =598)

[0218] Preparation Example 4

[0219]

[0220] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 4 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.8 g of compound 4. (Yield: 65%, MS: [M+H)) + =724)

[0221] Preparation Example 5

[0222]

[0223] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 5 (31.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.5 g of compound 5. (Yield: 65%, MS: [M+H)) + =714)

[0224] Preparation Example 6

[0225]

[0226] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 6 (28.3 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.2 g of compound 6. (Yield: 73%, MS: [M+H)) + =654)

[0227] Preparation Example 7

[0228]

[0229] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 7 (27.2 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.3 g of compound 7. (Yield: 78%, MS: [M+H)) + =637)

[0230] Preparation Example 8

[0231]

[0232] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 8 (24.3 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.1 g of compound 8. (Yield: 63%, MS: [M+H)) + =588)

[0233] Preparation Example 9

[0234]

[0235] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 9 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 9. (Yield: 63%, MS: [M+H)) + =674)

[0236] Preparation Example 10

[0237]

[0238] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 10 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.3 g of compound 10. (Yield: 71%, MS: [M+H)) + =674)

[0239] Preparation Example 11

[0240]

[0241] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 11 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.5 g of compound 11. (Yield: 69%, MS: [M+H)) + =674)

[0242] Preparation Example 12

[0243]

[0244] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 12 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.8 g of compound 12. (Yield: 60%, MS: [M+H]+=724)

[0245] Preparation Example 13

[0246]

[0247] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 13 (34 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 33.8 g of compound 13. (Yield: 79%, MS: [M+H)) + =750)

[0248] Preparation Example 14

[0249]

[0250] Under a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine 14 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.3 g of compound 14. (Yield: 76%, MS: [M+H)) + =700)

[0251] Preparation Example 15

[0252]

[0253] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 15 (24.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.8 g of compound 15. (Yield: 64%, MS: [M+H)) + =598)

[0254] Preparation Example 16

[0255]

[0256] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 16 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.3 g of compound 16. (Yield: 66%, MS: [M+H)) + =700)

[0257] Preparation Example 17

[0258]

[0259] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 17 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.7 g of compound 17. (Yield: 72%, MS: [M+H)) + =674)

[0260] Preparation Example 18

[0261]

[0262] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 18 (27.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.4 g of compound 18. (Yield: 66%, MS: [M+H)) + =648)

[0263] Preparation Example 19

[0264]

[0265] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 19 (28.1 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.5 g of compound 19. (Yield: 74%, MS: [M+H)) + =652)

[0266] Preparation Example 20

[0267]

[0268] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 20 (30.3 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.3 g of compound 20. (Yield: 72%, MS: [M+H)) + =688)

[0269] Preparation Example 21

[0270]

[0271] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 21 (28.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.8 g of compound 21. (Yield: 68%, MS: [M+H)) + =664)

[0272] Preparation Example 22

[0273]

[0274] Under a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 22 (30.3 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.6 g of compound 22. (Yield: 78%, MS: [M+H)) + =688)

[0275] Preparation Example 23

[0276]

[0277] Under a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine 23 (26.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.6 g of compound 23. (Yield: 69%, MS: [M+H)) + =624)

[0278] Preparation Example 24

[0279]

[0280] Under a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine 24 (27.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.3 g of compound 24. (Yield: 74%, MS: [M+H]) + =648)

[0281] Preparation Example 25

[0282]

[0283] Under a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine 25 (26.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 25. (Yield: 66%, MS: [M+H)) + =624)

[0284] Preparation Example 26

[0285]

[0286] Under a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine 26 (30.1 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 26. (Yield: 62%, MS: [M+H)) + =684)

[0287] Preparation Example 27

[0288]

[0289] Under a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine 27 (26.7 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.7 g of compound 27. (Yield: 69%, MS: [M+H)) + =628)

[0290] Preparation Example 28

[0291]

[0292] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 28 (26.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 28. (Yield: 68%, MS: [M+H)) + =624)

[0293] Preparation Example 29

[0294]

[0295] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 29 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.8 g of compound 29. (Yield: 60%, MS: [M+H)) + =724)

[0296] Preparation Example 30

[0297]

[0298] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 30 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.9 g of compound 30. (Yield: 80%, MS: [M+H)) + =700)

[0299] Preparation Example 31

[0300]

[0301] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 31 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.8 g of compound 31. (Yield: 80%, MS: [M+H)) + =674)

[0302] Preparation Example 32

[0303]

[0304] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 32 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.1 g of compound 32. (Yield: 73%, MS: [M+H)) + =674)

[0305] Preparation Example 33

[0306]

[0307] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 33 (28.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.9 g of compound 33. (Yield: 79%, MS: [M+H)) + =664)

[0308] Preparation Example 34

[0309]

[0310] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 34 (29.1 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.4 g of compound 34. (Yield: 72%, MS: [M+H)) + =668)

[0311] Preparation Example 35

[0312]

[0313] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 35 (30.3 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 35. (Yield: 60%, MS: [M+H)) + =688)

[0314] Preparation Example 36

[0315]

[0316] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 36 (26.7 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.4 g of compound 36. (Yield: 71%, MS: [M+H)) + =628)

[0317] Preparation Example 37

[0318]

[0319] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 37 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.9 g of compound 37. (Yield: 80%, MS: [M+H]) + =700)

[0320] Preparation Example 38

[0321]

[0322] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 38 (24.9 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 38. (Yield: 69%, MS: [M+H)) + =598)

[0323] Preparation Example 39

[0324]

[0325] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 39 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.6 g of compound 39. (Yield: 74%, MS: [M+H)) + =724)

[0326] Preparation Example 40

[0327]

[0328] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 40 (34 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.8 g of compound 40. (Yield: 72%, MS: [M+H)) + =750)

[0329] Preparation Example 41

[0330]

[0331] Under a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 41 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26 g of compound 41. (Yield: 63%, MS: [M+H)) + =724)

[0332] Preparation Example 42

[0333]

[0334] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 42 (26.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.6 g of compound 42. (Yield: 72%, MS: [M+H)) + =624)

[0335] Preparation Example 43

[0336]

[0337] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 43 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.2 g of compound 43. (Yield: 76%, MS: [M+H)) + =674)

[0338] Preparation Example 44

[0339]

[0340] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 44 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.4 g of compound 44. (Yield: 64%, MS: [M+H)) + =724)

[0341] Preparation Example 45

[0342]

[0343] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 45 (22.7 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.4 g of compound 45. (Yield: 70%, MS: [M+H)) + =562)

[0344] Preparation Example 46

[0345]

[0346] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 46 (31.8 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.6 g of compound 46. (Yield: 63%, MS: [M+H)) + =713)

[0347] Preparation Example 47

[0348]

[0349] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 47 (25.7 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.4 g of compound 47. (Yield: 70%, MS: [M+H]) + =612)

[0350] Preparation Example 48

[0351]

[0352] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 48 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.5 g of compound 48. (Yield: 79%, MS: [M+H)) + =700)

[0353] Preparation Example 49

[0354]

[0355] Under a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 49 (32.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 49. (Yield: 61%, MS: [M+H]) + =724)

[0356] Preparation Example 50

[0357]

[0358] Under a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine 50 (26.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.3 g of compound 50. (Yield: 71%, MS: [M+H)) + =624)

[0359] Preparation Example 51

[0360]

[0361] Under a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine 51 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 51. (Yield: 63%, MS: [M+H)) + =700)

[0362] Preparation Example 52

[0363]

[0364] Under a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine 52 (29.5 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.1 g of compound 52. (Yield: 73%, MS: [M+H)) + =674)

[0365] Preparation Example 53

[0366]

[0367] Under a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine 53 (31 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.9 g of compound 53. (Yield: 65%, MS: [M+H)) + =700)

[0368] Preparation Example 54

[0369]

[0370] Under a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine 54 (34 g, 59.9 mmol) were added to 300 mL of THF, and the mixture was stirred and refluxed. Potassium carbonate (23.7 g, 171.3 mmol) was then dissolved in 71 mL of water and added to the mixture. The mixture was stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. It was redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.4 g of compound 54. (Yield: 71%, MS: [M+H)) + =750)

[0371] [Example]

[0372] Example 1

[0373] It is coated with a thickness of A glass substrate with an ITO (indium tin oxide) thin film was immersed in distilled water containing a cleaning agent dissolved therein and washed ultrasonically. In this case, the cleaning agent used was a commercially available product from Fischer Co., and the distilled water was distilled water filtered twice using a commercially available filter from Millipore Co. The ITO was cleaned for 30 minutes, followed by two 10-minute ultrasonic cleaning cycles using distilled water. After the distilled water washing was complete, the substrate was ultrasonically cleaned with isopropanol, acetone, and methanol solvents and dried before being transferred to a plasma cleaner. The substrate was then cleaned with oxygen plasma for 5 minutes and transferred to a vacuum evaporator.

[0374] On such prepared ITO transparent electrodes, The following compound HI-1 was formed as a hole injection layer with a thickness of [thickness value missing], while the following compound A-1 was p-doped at a concentration of 1.5 wt%. The following compound HT-1 was then vacuum-deposited on the hole injection layer to form a film with a thickness of [thickness value missing]. The hole transport layer. Then, compound 1 prepared in Example 1 was prepared by vacuum deposition on the hole transport layer. The thickness is such that an electron blocking layer is formed. Then, compound RH-1 and compound Dp-7 as a dopant are vacuum deposited on the electron blocking layer at a weight ratio of 98:2 to form a thickness of [missing information]. A red luminescent layer. The following compound HB-1 was vacuum-deposited onto the luminescent layer. The film thickness is adjusted to form a hole-blocking layer. Then, compound ET-1 and compound LiQ are vacuum-deposited on the hole-blocking layer at a weight ratio of 2:1 to form a film with a thickness of [missing information]. An electron transport and injection layer. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron transport and injection layer to respectively possess... and The thickness of the cathode is thus formed.

[0375]

[0376] In the above process, the deposition rate of organic materials is maintained at / seconds / second, maintaining the deposition rates of lithium fluoride and aluminum at the cathode at respectively / second and / second, and maintain the vacuum level at 2×10 during deposition. -7 Up to 5×10 -6 This allows for the fabrication of organic light-emitting devices.

[0377] Examples 2 to 54

[0378] The organic light-emitting device was manufactured in the same manner as in Example 1, except that in the organic light-emitting device of Example 1, the compounds shown in Table 1 below were used instead of compound 1.

[0379] Comparative Examples 1 to 16

[0380] The organic light-emitting device was manufactured in the same manner as in Example 1, except that in the organic light-emitting device of Example 1, the compounds shown in Table 1 below were used instead of compound 1. The structures of compounds C-1 to C-16 in Table 1 are as follows.

[0381]

[0382] [Experimental Example]

[0383] By applying a current (15 mA / cm²) to the organic light-emitting devices manufactured in Examples 1 to 54 and Comparative Examples 1 to 16 2 The drive voltage and efficiency were measured, and the results are shown in Table 1 below. Lifetime T95 refers to the time required for the brightness to decrease to 95% of the initial brightness (6000 nits).

[0384] [Table 1]

[0385]

[0386]

[0387] Comparative Example 7 Compound C-7 4.46 13.41 81 Red Comparative Example 8 Compound C-8 4.39 12.48 63 Red Comparative Example 9 Compound C-9 4.15 14.88 121 Red Comparative Example 10 Compound C-10 4.42 12.18 64 Red Comparative Example 11 Compound C-11 4.41 12.32 57 Red Comparative Example 12 Compound C-12 4.22 15.28 103 Red Comparative Example 13 Compound C-13 4.18 15.11 101 Red Comparative Example 14 Compound C-14 4.09 15.36 126 Red Comparative Example 15 Compound C-15 4.17 15.06 94 Red Comparative Example 16 Compound C-16 4.38 13.33 77 Red

[0388] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 54 and Comparative Examples 1 to 16, the results shown in Table 1 were obtained. In the examples and comparative examples, materials widely used in the prior art were used as materials other than the electron blocking layer, and Dp-7 was used as the dopant for the red light-emitting layer.

[0389] Referring to the results in Table 1 above, compared to the comparative examples, the driving voltage was significantly reduced and the efficiency was improved when the compound of this disclosure was used as the electron blocking layer. In this respect, the energy transfer from the host to the red dopant was found to be successful. Furthermore, it was found that lifetime characteristics could be greatly improved while maintaining high efficiency.

[0390] In summary, when the compounds of the present invention are used as electron blocking layers in red light-emitting devices, the driving voltage, luminous efficiency, and lifetime characteristics of organic light-emitting devices can be improved.

[0391] <Figure Labels>

[0392] 1: Substrate 2: Anode

[0393] 3: Electron blocking layer; 4: Emissive layer

[0394] 5: Cathode; 6: Hole injection layer

[0395] 7: Hole transport layer 8: Hole blocking layer

[0396] 9: Electron transport and injection layer

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] ###0001### in Chemical Formula 1, [Chemical Formula 2] ###0002### in Chemical Formula 2, L1 is selected from any one of the following: R1to R 12 any one of R1to R4is a substituent represented by the following Chemical Formula 2, and the rest are each independently hydrogen or deuterium, L2 and L3 are each independently a single bond, phenylene, phenylene substituted with one phenyl group, biphenyldiyl, biphenyldiyl substituted with one phenyl group, or naphthalenediyl, Ar1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, dimethylfluorenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, and Ar2 is biphenyl, terphenyl, naphthyl, phenanthryl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, dimethylfluorenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, 2. The compound according to claim 1, wherein L2 and L3 are each independently a single bond or selected from any one of the following:

3. The compound according to claim 1, wherein: wherein the compound does not include Ar1 is selected from any one of the following:

4. The compound according to claim 1, wherein Ar2 is selected from any one of the following:

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is selected from any one of the following: 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 one or more of the organic material layers comprise the compound according to any one of claims 1 to 5.

6. An organic light emitting device comprising:

7. The organic light emitting device according to claim 6, wherein the organic material layer is an emission layer.

8. The organic light emitting device according to claim 6, wherein the organic material layer comprises an electron blocking layer, and wherein the electron blocking layer comprises the compound. ​ ​ ​

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