Novel compound and organic light-emitting device containing the same

Abstract

The present invention provides novel compounds and organic light-emitting devices using the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0104201 filed on August 19, 2020 and Korean Patent Application No. 10-2021-0109438 filed on August 19, 2021, and incorporates all the contents disclosed in the documents of the Korean patent applications as a part of this specification.

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

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.

[0005] An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted.

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

[0007] Prior art literature

[0008] Patent Literature

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

[0010] Technical issues

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

[0012] Solution to the problem

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

[0014] [Chemical formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] L is a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0018] R1 to R4 are each independently hydrogen or deuterium, or two adjacent ones are combined to form a benzene ring, and the rest are hydrogen or deuterium.

[0019] Ar1 is substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0020] Ar2 is substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0021] Ar3 is a substituent represented by the following chemical formula 2:

[0022] [Chemical formula 2]

[0023]

[0024] In the above chemical formula 2,

[0025] One of R is a part bonded to Chemical Formula 1, and the rest are hydrogen or deuterium.

[0026] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and at least one organic layer arranged between the first electrode and the second electrode, at least one of the organic layers contains the compound represented by the above chemical formula 1.

[0027] Effects of the Invention

[0028] The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, lower driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, electron suppression, luminescence, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1The figure shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 .

[0030] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 7 , an electron transport layer 8 , and a cathode 4 .

[0031] Figure 3 The diagram shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , an electron suppression layer 9 , a light-emitting layer 7 , an electron transport layer 8 , and a cathode 4 . DETAILED DESCRIPTION

[0032] In the following, the present invention will be described in more detail to help understanding the present invention.

[0033] In this manual, or It represents the bond to other substituents.

[0034] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphino group, or heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with substituents formed by connecting two or more substituents among the substituents exemplified above. For example, "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0035] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0036]

[0037] In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the group may be a group of the following structural formula, but is not limited thereto.

[0038]

[0039] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0040]

[0041] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0042] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0043] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0044] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0045] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0046] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0047] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0048] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form etc., but not limited thereto.

[0049] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0050] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the aryl group described above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in aralkenyl is the same as the examples of the alkenyl group described above. In the present specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above-mentioned description of the aryl group or cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above-mentioned description of the heterocyclic group can be applied.

[0051] In the above Chemical Formula 1, one or more hydrogens may be substituted with deuterium.

[0052] Preferably, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0053] [Chemical formula 1-1]

[0054]

[0055] [Chemical formula 1-2]

[0056]

[0057] [Chemical formula 1-3]

[0058]

[0059] In the above chemical formulas 1-1 to 1-3,

[0060] L, R1 to R4 and Ar1 to Ar3 are the same as defined above.

[0061] Preferably, L is a single bond, a phenylene group, a biphenyldiyl group or a naphthylene group.

[0062] Preferably, L is a single bond, or is selected from any one of the following groups:

[0063]

[0064] Preferably, Ar1 is unsubstituted C 6-18 Aryl. Preferably, Ar1 is phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl or phenanthryl.

[0065] Preferably, Ar2 is unsubstituted C 6-20 Aryl. Preferably, Ar2 is phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, phenanthrenylphenyl, triphenylene, dibenzofuranyl or dibenzothiophenyl.

[0066] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] On the other hand, as an example, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.

[0085] [Reaction 1]

[0086]

[0087] In the above reaction formula 1, the remaining definitions except X are the same as those above, and X is a halogen, more preferably chlorine or bromine. The above reaction is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be changed according to the technology known in the art. The above production method can be more specifically described in the production examples described later.

[0088] In addition, the present invention provides an organic light-emitting device including the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layers including the compound represented by the above chemical formula 1.

[0089] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, but may also be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0090] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0091] In addition, the organic layer includes an electron suppressing layer, and the electron suppressing layer includes the compound represented by the chemical formula 1.

[0092] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0093] In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons contains the compound represented by Chemical Formula 1.

[0094] In addition, the organic layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include the compound represented by Chemical Formula 1.

[0095] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figures 1 to 3 .

[0096] Figure 1 The figure shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above light emitting layer.

[0097] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8 and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in at least one of the above hole injection layer, hole transport layer, light-emitting layer and electron transport layer.

[0098] Figure 3 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in at least one of the above hole injection layer, hole transport layer, electron suppression layer, light-emitting layer, and electron transport layer.

[0099] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0100] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0101] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0102] In addition to this method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0103] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0104] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0105] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0106] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0107] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited to these.

[0108] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and preferably has a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0109] The light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as the aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but it is not limited thereto.

[0110] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0111] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. The material with high electron mobility is suitable. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0112] The electron injection layer is a layer for injecting electrons from the electrode, and preferably uses the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have excellent electron injection effects on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0113] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, 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) gallium chloride, 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.

[0114] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0115] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0116] Below, preferred examples are presented to help understand the present invention. However, the following examples are provided only to make the present invention easier to understand, and the content of the present invention is not limited thereto.

[0117] [Manufacturing example]

[0118] Production Example 1

[0119]

[0120] Under a nitrogen atmosphere, 2-bromo-1-chloro-3-fluorobenzene (15g, 71.6mmol) and (3-hydroxynaphthalene-2-yl)boric acid (14.8g, 78.8mmol) were added to THF (300ml), stirred and refluxed. Then, potassium carbonate (29.7g, 214.9mmol) was dissolved in water (89ml) and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.4g, 0.7mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2g of compound AA_P1. (Yield 73%, MS: [M+H] + =273)

[0121] Under nitrogen atmosphere, compound AA_P1 (15 g, 55 mmol) and potassium carbonate (22.8 g, 165 mmol) were added to DMF (300 ml), stirred and refluxed. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.3 g of compound AA. (Yield 74%, MS: [M+H] + =253)

[0122] Production Example 2

[0123]

[0124] Compound AB was produced by the same method as in Production Example 1 except that 2-bromo-4-chloro-1-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene.

[0125] Production Example 3

[0126]

[0127] Compound AC was produced by the same method as in Production Example 1 except that 1-bromo-4-chloro-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene.

[0128] Production Example 4

[0129]

[0130] Compound AD was produced by the same method as in Production Example 1 except that 1-bromo-3-chloro-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene.

[0131] Production Example 5

[0132]

[0133] Compound AE was prepared by the same method as in Preparation Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (4-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0134] Production Example 6

[0135]

[0136] Compound AF was prepared by the same method as in Preparation Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (5-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0137] Production Example 7

[0138]

[0139] Compound AG was prepared by the same method as in Preparation Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (6-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0140] Production Example 8

[0141]

[0142] Compound AH was produced by the same method as in Production Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (7-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0143] Production Example 9

[0144]

[0145] Compound AI was prepared by the same method as in Preparation Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (8-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0146] Production Example 10

[0147]

[0148] Compound AJ was prepared by the same method as in Preparation Example 1 except that 1-bromo-2-fluorobenzene was used instead of 2-bromo-1-chloro-3-fluorobenzene and (1-chloro-3-hydroxynaphthalen-2-yl)boric acid was used instead of (3-hydroxynaphthalen-2-yl)boric acid.

[0149] [Example]

[0150] Example 1

[0151]

[0152] Under a nitrogen atmosphere, compound substance (sub) 1 (10 g, 31 mmol), compound amine (amine) 1 (9.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, it was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of compound substance 1-1. (Yield 63%, MS: [M+H] + =537)

[0153] Under a nitrogen atmosphere, compound 1-1 (10 g, 18.6 mmol), compound AA (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 1. (Yield 57%, MS: [M+H] + =753)

[0154] Example 2

[0155]

[0156] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 2 (7.6 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of compound 1-2. (Yield 54%, MS: [M+H] + =487)

[0157] Under nitrogen atmosphere, compound substance 1-2 (10 g, 20.5 mmol), compound AA (5.2 g, 20.5 mmol), sodium tert-butoxide (2.6 g, 26.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.1 g of compound 2. (Yield 63%, MS: [M+H] + =703)

[0158] Example 3

[0159]

[0160] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 3 (6.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of compound 1-3. (Yield 60%, MS: [M+H] + =441)

[0161] Under nitrogen atmosphere, compound substance 1-3 (10 g, 22.7 mmol), compound AA (5.7 g, 22.7 mmol), sodium tert-butoxide (2.8 g, 29.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 3. (Yield 54%, MS: [M+H] + =657)

[0162] Example 4

[0163]

[0164] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 4 (6.8 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 1-4. (Yield 68%, MS: [M+H] + =461)

[0165] Under a nitrogen atmosphere, compound 1-4 (10 g, 21.7 mmol), compound AB (5.5 g, 21.7 mmol), sodium tert-butoxide (2.7 g, 28.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 4. (Yield 59%, MS: [M+H] + =677)

[0166] Example 5

[0167]

[0168] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 5 (5.7 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.2 g of compound 1-5. (Yield 55%, MS: [M+H] + =425)

[0169] Under nitrogen atmosphere, compound 1-5 (10 g, 23.5 mmol), compound AB (5.9 g, 23.5 mmol), sodium tert-butoxide (2.9 g, 30.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2 g of compound 5. (Yield 68%, MS: [M+H] + =641)

[0170] Experimental Example 6

[0171]

[0172] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 6 (5.3 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 1-6. (Yield 62%, MS: [M+H] + =411)

[0173] Under nitrogen atmosphere, compound 1-6 (10 g, 24.4 mmol), compound AC (6.2 g, 24.4 mmol), sodium tert-butoxide (3 g, 31.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 6. (Yield 63%, MS: [M+H] + =627)

[0174] Example 7

[0175]

[0176] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 7 (6.8 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 1-7. (Yield 67%, MS: [M+H] + =461)

[0177] Under nitrogen atmosphere, compound 1-7 (10 g, 21.7 mmol), compound AC (5.5 g, 21.7 mmol), sodium tert-butoxide (2.7 g, 28.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 7. (Yield 68%, MS: [M+H] + =677)

[0178] Example 8

[0179]

[0180] Under nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 8 (9.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 1-8. (Yield 62%, MS: [M+H] + =537)

[0181] Under nitrogen atmosphere, compound 1-8 (10 g, 18.6 mmol), compound AD (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 8. (Yield 67%, MS: [M+H] + =753)

[0182] Example 9

[0183]

[0184] Under nitrogen atmosphere, compound 2 (10 g, 26.9 mmol), compound amine 9 (4.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 2-1. (Yield 61%, MS: [M+H] + =461)

[0185] Under a nitrogen atmosphere, compound 2-1 (10 g, 21.7 mmol), compound AA (5.5 g, 21.7 mmol), sodium tert-butoxide (2.7 g, 28.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 9. (Yield 69%, MS: [M+H] + =677)

[0186] Example 10

[0187]

[0188] Under nitrogen atmosphere, compound substance 3 (10 g, 25.1 mmol), compound amine 8 (7.4 g, 25.1 mmol), sodium tert-butoxide (3.1 g, 32.6 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.6 g of compound substance 3-1. (Yield 69%, MS: [M+H] + =613)

[0189] Under a nitrogen atmosphere, compound 3-1 (10 g, 16.3 mmol), compound AD (4.1 g, 16.3 mmol), sodium tert-butoxide (2 g, 21.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.5 g of compound 10. (Yield 70%, MS: [M+H] + =829)

[0190] Embodiment 11

[0191]

[0192] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 10 (8.4 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 4-1. (Yield 50%, MS: [M+H] + =511)

[0193] Under a nitrogen atmosphere, compound 4-1 (10 g, 19.6 mmol), compound AA (4.9 g, 19.6 mmol), sodium tert-butoxide (2.4 g, 25.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of compound 11. (Yield 65%, MS: [M+H] + =727)

[0194] Example 12

[0195]

[0196] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 11 (7.6 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 4-2. (Yield 64%, MS: [M+H] + =487)

[0197] Under a nitrogen atmosphere, compound 4-2 (10 g, 20.5 mmol), compound AA (5.2 g, 20.5 mmol), sodium tert-butoxide (2.6 g, 26.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of compound 12. (Yield 57%, MS: [M+H] + =703)

[0198] Example 13

[0199]

[0200] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 12 (4.4 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 4-3. (Yield 56%, MS: [M+H] + =385)

[0201] Under a nitrogen atmosphere, compound 4-3 (10 g, 26 mmol), compound AB (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 13. (Yield 70%, MS: [M+H] + =601)

[0202] Embodiment 14

[0203]

[0204] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 13 (6 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 4-4. (Yield 69%, MS: [M+H] + =435)

[0205] Under nitrogen atmosphere, compound substance 4-4 (10 g, 23 mmol), compound AC (5.8 g, 23 mmol), sodium tert-butoxide (2.9 g, 29.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 14. (Yield 56%, MS: [M+H] + =651)

[0206] Embodiment 15

[0207]

[0208] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 6 (5.3 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7 g of compound 4-5. (Yield 55%, MS: [M+H] + =411)

[0209] Under nitrogen atmosphere, compound 4-5 (10 g, 24.4 mmol), compound AC (6.2 g, 24.4 mmol), sodium tert-butoxide (3 g, 31.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 15. (Yield 57%, MS: [M+H] + =627)

[0210] Example 16

[0211]

[0212] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 14 (8.4 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 4-6. (Yield 65%, MS: [M+H] + =511)

[0213] Under nitrogen atmosphere, compound 4-6 (10 g, 19.6 mmol), compound AC (4.9 g, 19.6 mmol), sodium tert-butoxide (2.4 g, 25.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.4 g of compound 16. (Yield 52%, MS: [M+H] + =727)

[0214] Embodiment 17

[0215]

[0216] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 15 (6.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.5 g of compound 4-7. (Yield 62%, MS: [M+H] + =441)

[0217] Under nitrogen atmosphere, compound 4-7 (10 g, 22.7 mmol), compound AC (5.7 g, 22.7 mmol), sodium tert-butoxide (2.8 g, 29.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of compound 17. (Yield 62%, MS: [M+H] + =657)

[0218] Embodiment 18

[0219]

[0220] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 16 (9.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of compound 4-8. (Yield 59%, MS: [M+H] + =537)

[0221] Under nitrogen atmosphere, compound 4-8 (10 g, 18.6 mmol), compound AD (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.5 g of compound 18. (Yield 68%, MS: [M+H] + =753)

[0222] Embodiment 19

[0223]

[0224] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 17 (5.7 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of compound 4-9. (Yield 67%, MS: [M+H] + =425)

[0225] Under nitrogen atmosphere, compound 4-9 (10 g, 23.6 mmol), compound AD (6 g, 23.6 mmol), sodium tert-butoxide (2.9 g, 30.6 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 19. (Yield 67%, MS: [M+H] + =641)

[0226] Embodiment 20

[0227]

[0228] Under nitrogen atmosphere, compound 4-8 (10 g, 18.6 mmol), compound AE (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 20. (Yield 60%, MS: [M+H] + =753)

[0229] Embodiment 21

[0230]

[0231] Under a nitrogen atmosphere, compound 4-5 (10 g, 24.4 mmol), compound AG (6.2 g, 24.4 mmol), sodium tert-butoxide (3 g, 31.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of compound 21. (Yield 65%, MS: [M+H] + =627)

[0232] Embodiment 22

[0233]

[0234] Under nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 18 (6.8 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.1 g of compound 4-10. (Yield 64%, MS: [M+H] + =461)

[0235] Under nitrogen atmosphere, compound 4-10 (10 g, 21.7 mmol), compound AH (5.5 g, 21.7 mmol), sodium tert-butoxide (2.7 g, 28.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of compound 22. (Yield 55%, MS: [M+H] + =677)

[0236] Embodiment 23

[0237]

[0238] Under nitrogen atmosphere, compound 5 (10 g, 31 mmol), compound amine 19 (7.6 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.3 g of compound 5-1. (Yield 55%, MS: [M+H] + =485)

[0239] Under a nitrogen atmosphere, compound 5-1 (10 g, 20.6 mmol), compound AB (5.2 g, 20.6 mmol), sodium tert-butoxide (2.6 g, 26.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 23. (Yield 58%, MS: [M+H] + =701)

[0240] Embodiment 24

[0241]

[0242] Under nitrogen atmosphere, compound 5 (10 g, 31 mmol), compound amine 20 (9.2 g, 31 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2 g of compound 5-2. (Yield 61%, MS: [M+H] + =537)

[0243] Under nitrogen atmosphere, compound 5-2 (10 g, 18.6 mmol), compound AC (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 24. (Yield 57%, MS: [M+H] + =753)

[0244] Embodiment 25

[0245]

[0246] Under a nitrogen atmosphere, compound substance 6 (10 g, 25.1 mmol), compound amine 6 (4.2 g, 25.1 mmol), sodium tert-butoxide (3.1 g, 32.6 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, it was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.8 g of compound substance 6-1. (Yield 56%, MS: [M+H] + =487)

[0247] Under a nitrogen atmosphere, compound 6-1 (10 g, 20.5 mmol), compound AA (5.2 g, 20.5 mmol), sodium tert-butoxide (2.6 g, 26.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of compound 25. (Yield 62%, MS: [M+H] + =703)

[0248] Embodiment 26

[0249]

[0250] Under nitrogen atmosphere, compound 6 (10 g, 25.1 mmol), compound amine 21 (5.5 g, 25.1 mmol), sodium tert-butoxide (3.1 g, 32.6 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 6-2. (Yield 50%, MS: [M+H] + =537)

[0251] Under a nitrogen atmosphere, compound 6-2 (10 g, 18.6 mmol), compound AH (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of compound 26. (Yield 58%, MS: [M+H] + =753)

[0252] Embodiment 27

[0253]

[0254] Under a nitrogen atmosphere, compound 7 (10 g, 21.1 mmol), compound amine 22 (2 g, 21.1 mmol), sodium tert-butoxide (2.6 g, 27.4 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 7-1. (Yield 69%, MS: [M+H] + =487)

[0255] Under a nitrogen atmosphere, compound 7-1 (10 g, 20.5 mmol), compound AE (5.2 g, 20.5 mmol), sodium tert-butoxide (2.6 g, 26.7 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 27. (Yield 55%, MS: [M+H] + =703)

[0256] Embodiment 28

[0257]

[0258] Under nitrogen atmosphere, compound 8 (10 g, 26.9 mmol), compound amine 23 (5.2 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.5 g of compound 8-1. (Yield 65%, MS: [M+H] + =485)

[0259] Under nitrogen atmosphere, compound 8-1 (10 g, 20.6 mmol), compound AC (5.2 g, 20.6 mmol), sodium tert-butoxide (2.6 g, 26.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 28. (Yield 54%, MS: [M+H] + =701)

[0260] Embodiment 29

[0261]

[0262] Under nitrogen atmosphere, compound 8 (10 g, 26.9 mmol), compound amine 22 (2.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 8-2. (Yield 50%, MS: [M+H] + =385)

[0263] Under a nitrogen atmosphere, compound 8-2 (10 g, 26 mmol), compound AH (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 29. (Yield 66%, MS: [M+H] + =601)

[0264] Embodiment 30

[0265]

[0266] Under nitrogen atmosphere, compound 9 (10 g, 26.9 mmol), compound amine 22 (2.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.9 g of compound 9-1. (Yield 57%, MS: [M+H] + =385)

[0267] Under a nitrogen atmosphere, compound 9-1 (10 g, 26 mmol), compound AG (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 30. (Yield 50%, MS: [M+H] + =601)

[0268] Embodiment 31

[0269]

[0270] Under nitrogen atmosphere, compound substance 10 (10 g, 22.3 mmol), compound amine 6 (3.8 g, 22.3 mmol), sodium tert-butoxide (2.8 g, 29 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, it was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.2 g of compound substance 10-1. (Yield 52%, MS: [M+H] + =537)

[0271] Under a nitrogen atmosphere, compound 10-1 (10 g, 18.6 mmol), compound AA (4.7 g, 18.6 mmol), sodium tert-butoxide (2.3 g, 24.2 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 31. (Yield 67%, MS: [M+H] + =753)

[0272] Embodiment 32

[0273]

[0274] Under a nitrogen atmosphere, compound 11 (10 g, 26.9 mmol), compound amine 22 (2.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.2 g of compound 11-1. (Yield 70%, MS: [M+H] + =385)

[0275] Under a nitrogen atmosphere, compound substance 11-1 (10 g, 26 mmol), compound AD (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 32. (Yield 62%, MS: [M+H] + =601)

[0276] Embodiment 33

[0277]

[0278] Under a nitrogen atmosphere, compound 12 (10 g, 26.9 mmol), compound amine 22 (2.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 12-1. (Yield 69%, MS: [M+H] + =385)

[0279] Under a nitrogen atmosphere, compound substance 12-1 (10 g, 26 mmol), compound AD (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 33. (Yield 62%, MS: [M+H] + =601)

[0280] Embodiment 34

[0281]

[0282] Under nitrogen atmosphere, compound 13 (10 g, 26.9 mmol), compound amine 22 (2.5 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 13-1. (Yield 65%, MS: [M+H] + =385)

[0283] Under a nitrogen atmosphere, compound substance 13-1 (10 g, 26 mmol), compound AB (6.6 g, 26 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 34. (Yield 66%, MS: [M+H] + =601)

[0284] Embodiment 35

[0285]

[0286] Under nitrogen atmosphere, compound substance 14 (10 g, 26.9 mmol), compound amine 24 (5.9 g, 26.9 mmol), sodium tert-butoxide (3.4 g, 34.9 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.4 g of compound substance 14-1. (Yield 54%, MS: [M+H] + =511)

[0287] Under a nitrogen atmosphere, compound 14-1 (10 g, 19.6 mmol), compound AD (4.9 g, 19.6 mmol), sodium tert-butoxide (2.4 g, 25.5 mmol) were added to xylene (200 ml), stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 35. (Yield 50%, MS: [M+H] + =727)

[0288] [Experimental example]

[0289] Experimental Example 1

[0290] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0291] On the ITO transparent electrode prepared in this way, as a hole injection layer, the following HI-1 compound was added in the form of The following A-1 compound was p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film with a thickness of On the hole transport layer, the compound 1 prepared above was vacuum-deposited to form a film with a thickness of On the electron suppression layer, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 to form a film with a thickness of On the above-mentioned light-emitting layer, the following HB-1 compound was vacuum-deposited to form a film with a thickness of On the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1, thereby forming a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0292]

[0293] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting device.

[0294] Experimental Examples 2 to 35

[0295] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds described in Tables 1 and 2 below were used instead of Compound 1.

[0296] Comparative Experimental Examples 1 to 8

[0297] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds described in Table 3 below were used instead of Compound 1. In Table 3 below, Compounds C-1 to C-8 are shown below.

[0298]

[0299] When current was applied to the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, the driving voltage and luminous efficiency (15 mA / cm 2), and the results are shown in the following Tables 1 to 3. In the following, the lifespan T95 refers to the time (hr) required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

[0300] [Table 1]

[0301]

[0302] [Table 2]

[0303]

[0304] [Table 3]

[0305]

[0306] As shown in Tables 1 to 3 above, when the compound of the present invention is used as an electron suppression layer, the driving voltage is greatly reduced and the efficiency is greatly increased compared to the comparative experimental example, from which it can be seen that the energy transfer from the host to the red dopant is well formed. In addition, it can be seen that high efficiency is maintained while greatly improving the life characteristics. It can be judged that this is because the compound of the present invention has high stability for electrons and holes compared to the compound used in the comparative experimental example. Therefore, it can be confirmed that when the compound of the present invention is used as an electron suppression layer, the driving voltage, luminous efficiency and life characteristics of the organic light-emitting device can be improved.

[0307] [Explanation of symbols]

[0308] 1: Substrate 2: Anode

[0309] 3: Light-emitting layer 4: Cathode

[0310] 5: Hole injection layer 6: Hole transport layer

[0311] 7: Light-emitting layer 8: Electron transport layer

[0312] 9: Electron suppression layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, R1 to R4 are each independently hydrogen or deuterium, or two adjacent ones are combined to form a benzene ring, and the rest are hydrogen or deuterium, L is a single bond, a phenylene group, a biphenylene group or a naphthylene group, Ar1 is phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, or phenylnaphthyl, Ar2 is phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, phenanthrenylphenyl, triphenylene, dibenzofuranyl or dibenzothiophenyl, Ar3 is a substituent represented by the following chemical formula 2: Chemical formula 2 In the chemical formula 2, One of R is a part that is bonded to chemical formula 1, and the rest are hydrogen or deuterium. In Chemical Formula 1, one or more hydrogen atoms are optionally replaced by deuterium.

2. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: Chemical formula 1-1 Chemical formula 1-2 Chemical formula 1-3 In the chemical formulas 1-1 to 1-3, L, R1 to R4 and Ar1 to Ar3 are the same as defined in claim 1.

3. The compound according to claim 1, wherein L is a single bond, or any one selected from the following groups:

4. The compound according to claim 1, wherein The compound represented by Chemical Formula 1 is any one selected from the following compounds:

5. An organic light-emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound according to any one of claims 1 to 4.

6. The organic light emitting device according to claim 5, wherein: The organic layer including the compound is an electron suppressing layer.

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