Novel compound and organic light-emitting device using same

Abstract

The invention provides a novel compound and an organic light-emitting device using the same.

Description

Technical Field

[0001] The present invention relates to novel compounds and organic light-emitting devices comprising the same. Background Art

[0002] 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.

[0003] 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.

[0004] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0005] Prior art literature

[0006] Patent Literature

[0007] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the invention

[0008] Technical issues

[0009] The present invention relates to novel compounds and organic light-emitting devices comprising the same.

[0010] Solution to the problem

[0011] The present invention provides a compound represented by the following Chemical Formula 1:

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60 Heteroaryl,

[0016] L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0017] R is substituted or unsubstituted C 6-60 Aryl,

[0018] D a and D b It means D a and D b The number of deuterium substitutions in the benzene ring of the phenanthryl group to which each is attached, a and b are each independently an integer from 0 to 4, wherein 0 <a+b≤8,

[0019] D m refers to the number of deuterium substitutions in the phenylene group, m is an integer from 0 to 4,

[0020] D n It refers to the number of deuterium substitutions in a compound, where n is an integer greater than 1.

[0021] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the above chemical formula 1.

[0022] Effects of the Invention

[0023] 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 a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection (hereinafter referred to as an "electron transport and electron injection layer"). BRIEF DESCRIPTION OF THE DRAWINGS

[0024] 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 .

[0025] 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 .

[0026] [Explanation of symbols]

[0027] 1: Substrate 2: Anode

[0028] 3: Light-emitting layer 4: Cathode

[0029] 5: Hole injection layer 6: Hole transport layer

[0030] 7: Light-emitting layer 8: Electron transport layer DETAILED DESCRIPTION

[0031] In the following, the present invention will be described in more detail to help understanding the present invention.

[0032] In this manual, It represents the bond to other substituents.

[0033] In this specification, D is deuterium, and for compounds or specific functional groups, "D x " means substituted by x deuterium. As an example, in Formula 1, D m It means that the phenylene group is substituted by m deuterium groups, wherein when m is an integer of 0, it means that the phenylene group is unsubstituted.

[0034] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or substituted or unsubstituted with one or more substituents in a heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a 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 structure shown below may be used, but the structure 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 structure may be as shown below, but the present invention 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 structure shown below may be used, but the present invention 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, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0043] 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 60. 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, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0044] 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 60. 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.

[0045] 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.

[0046] 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.

[0047] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0048] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, 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.

[0049] 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 heteroaryl 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 heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the heterocyclic group can be applied.

[0050] Preferably, the above chemical formula 1 can be represented by the following chemical formula 1-1:

[0051] [Chemical formula 1-1]

[0052]

[0053] In the above chemical formula 1-1,

[0054] Ar1, Ar2, L1, L2, R, D a , D b , D m , D n , a, b, m and n are the same as defined in the above Chemical Formula 1.

[0055] Preferably, in the above Chemical Formula 1, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, (phenyl)naphthyl or (naphthyl)phenyl, and the above Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuteriums.

[0056] Specifically, Ar1 and Ar2 are each independently any one of the following groups,

[0057] The above Ar1 and Ar2 may each independently be unsubstituted or may be substituted with one or more deuteriums:

[0058]

[0059] Preferably, in the above Chemical Formula 1, L1 and L2 are each independently a single bond; or a phenylene group, a biphenylene group or a naphthalenediyl group, and the above phenylene group, biphenylene group and naphthalenediyl group are each independently unsubstituted or substituted with one or more deuterium groups.

[0060] Specifically, L1 and L2 can each independently be a single bond, or can be any of the following formulae:

[0061]

[0062] In the above formula,

[0063] D p1 To D p28 It refers to the number of deuterium substitutions, and p1 to p28 are each independently an integer greater than or equal to 0.

[0064] Specifically, p1 to p5 and p12 to p19 are each independently an integer of 0 to 4. Furthermore, p6, p8, and p10 are each independently an integer of 0 to 3. Furthermore, p7, p9, and p11 are each independently an integer of 0 to 5. Furthermore, p20 to p28 are each independently an integer of 0 to 6.

[0065] Preferably, in the above Chemical Formula 1, R is a phenyl group or a naphthyl group, and the above R may be unsubstituted or substituted with one or more deuterium groups.

[0066] Specifically, R is any one of the following groups, and the above R may be unsubstituted or substituted with one or more deuteriums:

[0067]

[0068] In the above Chemical Formula 1, D is deuterium.

[0069] Preferably, in the above chemical formula 1, D a and D b In the above, a is an integer of 0, 1, 2, 3 or 4, b is an integer of 0, 1, 2, 3 or 4, and a+b is an integer of 1, 2, 3, 4, 5, 6, 7 or 8.

[0070] Preferably, in the above chemical formula 1, D m In the above formula, m is 0 or an integer from 1 to 4. Specifically, m is an integer from 0, 1, 2, 3 or 4.

[0071] Preferably, in the above chemical formula 1, D n In the above, n is an integer of 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, or 8 or more.

[0072] Specifically, n is an integer of 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more and 50 or less, 40 or less, 30 or less, 20 or less, or 10 or less.

[0073] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

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[0204] In the above chemical formula,

[0205] D m refers to the number of deuterium substitutions in the phenylene group, m is an integer from 0 to 4,

[0206] D n1 , D n2 , D n3 , D n4 , D n5 , D n6 , D n7 and D n8 refers to the number of deuterium substitutions in each compound.

[0207] n1 is an integer greater than 1,

[0208] n2 is an integer greater than or equal to 2,

[0209] n3 is an integer greater than or equal to 3,

[0210] n4 is an integer greater than or equal to 4,

[0211] n5 is an integer greater than or equal to 5,

[0212] n6 is an integer greater than or equal to 6,

[0213] n7 is an integer greater than or equal to 7,

[0214] n8 is an integer greater than or equal to 8.

[0215] Specifically, n1 is an integer of 1 to 50 or less, or 30 or less. In addition, n2 is an integer of 2 to 50 or less, or 30 or less. In addition, n3 is an integer of 3 to 50 or less, or 30 or less. In addition, n4 is an integer of 4 to 50 or less, or 30 or less. In addition, n5 is an integer of 5 to 10 to 50 or less, or 40 or less. In addition, n6 is an integer of 6 to 50 or less, or 40 or less. In addition, n7 is an integer of 7 to 50 or less, or 40 or less, or 35 or less. In addition, n8 is an integer of 8 to 20 to 25 to 50 or less, or 40 or less, or 35 or less.

[0216] On the other hand, as an example, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in the following Reaction Formula 1, and the remaining compounds can also be produced similarly.

[0217] [Reaction 1]

[0218]

[0219] In the above reaction formula 1, Ar1, Ar2, L1, L2, R, D a , D b , D m , D n , a, b, m and n are the same as those defined in the above Chemical Formula 1. In addition, X is a halogen group, specifically, X is chlorine or bromine. In addition, D p and D q Refers to the number of deuterium substitutions in each compound, D p is an integer greater than 0, D q is an integer greater than 1, and D p +D q =D n .

[0220] The above step is an amine substitution reaction, which is 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 techniques known in the art. The above production method can be further embodied in the production examples described below.

[0221] 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 including: a first electrode; a second electrode disposed opposite to the above first electrode; and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above chemical formula 1.

[0222] The organic layer of the organic light-emitting device of the present invention may be formed by a single-layer structure or a multi-layer 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, a hole transport auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, or an electron transport and injection layer as an organic layer. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0223] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0224] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a hole transport auxiliary layer, and the hole injection layer, the hole transport layer, or the hole transport auxiliary layer includes the compound represented by Chemical Formula 1.

[0225] In addition, the above-mentioned organic layer may include an electron transport layer, an electron injection layer, an electron transport auxiliary layer, or a layer that simultaneously performs electron transport and electron injection (hereinafter referred to as "electron transport and electron injection layer"), and the above-mentioned electron transport layer, electron injection layer, electron transport auxiliary layer, or electron transport and electron injection layer contains the compound represented by the above-mentioned Chemical Formula 1.

[0226] In addition, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, a hole blocking layer, and an electron transport and electron injection layer, and the above-mentioned hole injection layer, hole transport layer, hole transport auxiliary layer, light-emitting layer, hole blocking layer, or electron transport and electron injection layer contains the compound represented by the above-mentioned Chemical Formula 1.

[0227] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and Figure 2 .

[0228] 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.

[0229] Figure 2The 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 one or more of the above hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0230] 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.

[0231] 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.

[0232] 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.

[0233] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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.

[0238] 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 thereto.

[0239] 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 is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0240] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0241] 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 metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0242] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used 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.

[0243] 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 an excellent electron injection effect 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, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0244] 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.

[0245] 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.

[0246] 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.

[0247] The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0248] In this specification, unless otherwise specified, ordinary temperature refers to 23±5° C. which is a normal laboratory temperature.

[0249] Synthesis example 1

[0250]

[0251] Under a nitrogen atmosphere, amine 1 (10 g, 30.2 mmol), compound 1-1 (12 g, 31.7 mmol), sodium tert-butoxide (3.8 g, 39.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 1. (Yield 61%, MS: [M+H] + =676)

[0252] Synthesis example 2

[0253]

[0254] Under a nitrogen atmosphere, amine 2 (10 g, 24.2 mmol), compound 2-1 (9.5 g, 25.4 mmol), sodium tert-butoxide (3 g, 31.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 2. (Yield 73%, MS: [M+H] + =754)

[0255] Synthesis example 3

[0256]

[0257] Under a nitrogen atmosphere, amine 3 (10 g, 29.4 mmol), compound 3-1 (11.7 g, 30.8 mmol), sodium tert-butoxide (3.7 g, 38.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of compound 3. (Yield 73%, MS: [M+H] + =684)

[0258] Synthesis example 4

[0259]

[0260] Under a nitrogen atmosphere, amine 4 (10 g, 25.8 mmol), compound 4-1 (10.2 g, 27.1 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 4. (Yield 64%, MS: [M+H] + =730)

[0261] Synthesis example 5

[0262]

[0263] Under a nitrogen atmosphere, amine 5 (10 g, 24.1 mmol), compound 5-1 (9.6 g, 25.3 mmol), sodium tert-butoxide (3 g, 31.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.9 g of compound 5. (Yield 65%, MS: [M+H] + =759)

[0264] Synthesis example 6

[0265]

[0266] Under a nitrogen atmosphere, amine 6 (10 g, 25.5 mmol), compound 6-1 (10.1 g, 26.8 mmol), sodium tert-butoxide (3.2 g, 33.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 6. (Yield 73%, MS: [M+H] + =733)

[0267] Synthesis Example 7

[0268]

[0269] Under a nitrogen atmosphere, amine 7 (10 g, 30.1 mmol), compound 7-1 (11.9 g, 31.6 mmol), sodium tert-butoxide (3.8 g, 39.1 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of compound 7. (Yield 75%, MS: [M+H] + =675)

[0270] Synthesis example 8

[0271]

[0272] Under a nitrogen atmosphere, amine 8 (10 g, 31.1 mmol), compound 8-1 (14.2 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 8. (Yield 60%, MS: [M+H] + =720)

[0273] Synthesis example 9

[0274]

[0275] Under a nitrogen atmosphere, amine 9 (10 g, 23.1 mmol), compound 9-1 (10.3 g, 24.3 mmol), sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 9. (Yield 63%, MS: [M+H] + =805)

[0276] Synthesis example 10

[0277]

[0278] Under a nitrogen atmosphere, amine 10 (10 g, 29.4 mmol), compound 10-1 (11.5 g, 30.8 mmol), sodium tert-butoxide (3.7 g, 38.2 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of compound 10. (Yield 68%, MS: [M+H] + =677)

[0279] Synthesis Example 11

[0280]

[0281] Under a nitrogen atmosphere, amine 11 (10 g, 31.1 mmol), compound 11-1 (12.2 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.5 g of compound 11. (Yield 71%, MS: [M+H] + =659)

[0282] Synthesis example 12

[0283]

[0284] Under a nitrogen atmosphere, amine 12 (10 g, 25.2 mmol), compound 12-1 (10 g, 26.4 mmol), sodium tert-butoxide (3.1 g, 32.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 12. (Yield 70%, MS: [M+H] + =740)

[0285] Synthesis example 13

[0286]

[0287] Under a nitrogen atmosphere, amine 13 (10 g, 27.6 mmol), compound 13-1 (11 g, 29 mmol), and sodium tert-butoxide (3.4 g, 35.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.6 g of compound 13. (Yield 75%, MS: [M+H] + =706)

[0288] Synthesis example 14

[0289]

[0290] Under a nitrogen atmosphere, amine 14 (10 g, 25.5 mmol), compound 14-1 (10.1 g, 26.8 mmol), and sodium tert-butoxide (3.2 g, 33.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound 14. (Yield 74%, MS: [M+H] + =733)

[0291] Synthesis Example 15

[0292]

[0293] Under a nitrogen atmosphere, amine 15 (10 g, 25.8 mmol), compound 15-1 (10.2 g, 27.1 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 15. (Yield 66%, MS: [M+H] + =729)

[0294] Synthesis Example 16

[0295]

[0296] Under a nitrogen atmosphere, amine 16 (10 g, 25.8 mmol), compound 16-1 (10.2 g, 27.1 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.8 g of compound 16. (Yield 79%, MS: [M+H] + =728)

[0297] Synthesis Example 17

[0298]

[0299] Under a nitrogen atmosphere, amine 17 (10 g, 27.4 mmol), compound 17-1 (10.9 g, 28.8 mmol), sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of compound 17. (Yield 66%, MS: [M+H] + =705)

[0300] Synthesis example 18

[0301]

[0302] Under a nitrogen atmosphere, amine 18 (10 g, 29.9 mmol), compound 18-1 (11.9 g, 31.4 mmol), sodium tert-butoxide (3.7 g, 38.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of compound 18. (Yield 75%, MS: [M+H] + =678)

[0303] Synthesis example 19

[0304]

[0305] Under a nitrogen atmosphere, amine 19 (10 g, 26 mmol), compound 19-1 (10.2 g, 27.3 mmol), sodium tert-butoxide (3.2 g, 33.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound 19. (Yield 76%, MS: [M+H] + =721)

[0306] Synthesis example 20

[0307]

[0308] Under a nitrogen atmosphere, amine 20 (10 g, 25.9 mmol), compound 20-1 (10.2 g, 27.2 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.7 g of compound 20. (Yield 73%, MS: [M+H] + =728)

[0309] Synthesis Example 21

[0310]

[0311] Under a nitrogen atmosphere, amine 21 (10 g, 21.6 mmol), compound 21-1 (8.6 g, 22.6 mmol), sodium tert-butoxide (2.7 g, 28 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 21. (Yield 66%, MS: [M+H] + =806)

[0312] Synthesis example 22

[0313]

[0314] Under a nitrogen atmosphere, amine 22 (10 g, 22.6 mmol), compound 22-1 (8.9 g, 23.8 mmol), sodium tert-butoxide (2.8 g, 29.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 22. (Yield 70%, MS: [M+H] + =782)

[0315] Synthesis example 23

[0316]

[0317] Under a nitrogen atmosphere, amine 23 (10 g, 22.6 mmol), compound 23-1 (8.9 g, 23.8 mmol), sodium tert-butoxide (2.8 g, 29.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of compound 23. (Yield 63%, MS: [M+H] + =780)

[0318] Synthesis example 24

[0319]

[0320] Under a nitrogen atmosphere, amine 24 (10 g, 25.9 mmol), compound 24-1 (10.1 g, 27.2 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 24. (Yield 75%, MS: [M+H] + =723)

[0321] Synthesis example 25

[0322]

[0323] Under a nitrogen atmosphere, amine 25 (10 g, 31.1 mmol), compound 25-1 (12.1 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 15.3 g of compound 25. (Yield 75%, MS: [M+H] + =658)

[0324] Synthesis Example 26

[0325]

[0326] Under a nitrogen atmosphere, amine 26 (10 g, 23.8 mmol), compound 26-1 (9.4 g, 25 mmol), and sodium tert-butoxide (3 g, 30.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.1 g of compound 26. (Yield 67%, MS: [M+H] + =762)

[0327] Synthesis Example 27

[0328]

[0329] Under a nitrogen atmosphere, amine 27 (10 g, 24.3 mmol), compound 27-1 (9.7 g, 25.5 mmol), sodium tert-butoxide (3 g, 31.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.9 g of compound 27. (Yield 76%, MS: [M+H] + =756)

[0330] Synthesis example 28

[0331]

[0332] Under a nitrogen atmosphere, amine 28 (10 g, 24.2 mmol), compound 28-1 (9.6 g, 25.5 mmol), sodium tert-butoxide (3 g, 31.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 28. (Yield 79%, MS: [M+H] + =755)

[0333] Synthesis Example 29

[0334]

[0335] Under a nitrogen atmosphere, amine 29 (10 g, 25.5 mmol), compound 29-1 (10.1 g, 26.8 mmol), and sodium tert-butoxide (3.2 g, 33.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 29. (Yield 61%, MS: [M+H] + =734)

[0336] Synthesis example 30

[0337]

[0338] Under a nitrogen atmosphere, amine 30 (10 g, 24.2 mmol), compound 30-1 (9.5 g, 25.4 mmol), sodium tert-butoxide (3 g, 31.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.3 g of compound 30. (Yield 62%, MS: [M+H] + =754)

[0339] Synthesis Example 31

[0340]

[0341] Under a nitrogen atmosphere, amine 31 (10 g, 21.2 mmol), compound 31-1 (8.3 g, 22.2 mmol), sodium tert-butoxide (2.6 g, 27.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of compound 31. (Yield 63%, MS: [M+H] + =808)

[0342] Synthesis example 32

[0343]

[0344] Under a nitrogen atmosphere, amine 32 (10 g, 24.3 mmol), compound 32-1 (9.6 g, 25.5 mmol), sodium tert-butoxide (3 g, 31.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 32. (Yield 71%, MS: [M+H] + =753)

[0345] Synthesis example 33

[0346]

[0347] Under a nitrogen atmosphere, amine 33 (10 g, 21.5 mmol), compound 33-1 (8.5 g, 22.6 mmol), sodium tert-butoxide (2.7 g, 28 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.9 g of compound 33. (Yield 80%, MS: [M+H] + =806)

[0348] Synthesis example 34

[0349]

[0350] Under a nitrogen atmosphere, amine 34 (10 g, 21.2 mmol), compound 34-1 (8.4 g, 22.2 mmol), sodium tert-butoxide (2.6 g, 27.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 34. (Yield 64%, MS: [M+H] + =812)

[0351] Synthesis Example 35

[0352]

[0353] Under a nitrogen atmosphere, amine 35 (10 g, 20.3 mmol), compound 35-1 (8.1 g, 21.4 mmol), sodium tert-butoxide (2.5 g, 26.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 35. (Yield 65%, MS: [M+H] + =834)

[0354] Synthesis example 36

[0355]

[0356] Under a nitrogen atmosphere, amine 36 (10 g, 23.8 mmol), compound 36-1 (9.4 g, 25 mmol), and sodium tert-butoxide (3 g, 30.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 36. (Yield 62%, MS: [M+H] + =760)

[0357] Synthesis Example 37

[0358]

[0359] Under a nitrogen atmosphere, amine 37 (10 g, 25.2 mmol), compound 37-1 (9.8 g, 26.4 mmol), sodium tert-butoxide (3.1 g, 32.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 37. (Yield 74%, MS: [M+H] + =733)

[0360] Synthesis example 38

[0361]

[0362] Under a nitrogen atmosphere, amine 38 (10 g, 25.9 mmol), compound 38-1 (10.3 g, 27.2 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 38. (Yield 61%, MS: [M+H] + =729)

[0363] Synthesis Example 39

[0364]

[0365] Under a nitrogen atmosphere, amine 39 (10 g, 20.4 mmol), compound 39-1 (8 g, 21.4 mmol), and sodium tert-butoxide (2.5 g, 26.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 39. (Yield 77%, MS: [M+H] + =830)

[0366] Synthesis Example 40

[0367]

[0368] Under a nitrogen atmosphere, amine 40 (10 g, 20.4 mmol), compound 40-1 (8.1 g, 21.4 mmol), sodium tert-butoxide (2.6 g, 26.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 40. (Yield 69%, MS: [M+H] + =833)

[0369] Synthesis Example 41

[0370]

[0371] Under a nitrogen atmosphere, amine 41 (10 g, 25.7 mmol), compound 41-1 (10.3 g, 27 mmol), sodium tert-butoxide (3.2 g, 33.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 41. (Yield 75%, MS: [M+H] + =733)

[0372] Synthesis Example 42

[0373]

[0374] Under a nitrogen atmosphere, amine 42 (10 g, 25.2 mmol), compound 42-1 (9.8 g, 26.4 mmol), sodium tert-butoxide (3.1 g, 32.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 42. (Yield 62%, MS: [M+H] + =785)

[0375] Synthesis Example 43

[0376]

[0377] Under a nitrogen atmosphere, amine 43 (10 g, 26.9 mmol), compound 43-1 (10.6 g, 28.3 mmol), sodium tert-butoxide (3.4 g, 35 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 43. (Yield 75%, MS: [M+H] + =711)

[0378] Synthesis Example 44

[0379]

[0380] Under nitrogen atmosphere, amine 44 (10 g, 20 mmol), compound 44-1 (7.9 g, 21 mmol), sodium tert-butoxide (2.5 g, 26 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was over, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 44. (Yield 67%, MS: [M+H] + =840)

[0381] Synthesis Example 45

[0382]

[0383] Under a nitrogen atmosphere, amine 45 (10 g, 25.2 mmol), compound 45-1 (9.8 g, 26.4 mmol), sodium tert-butoxide (3.1 g, 32.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound 45. (Yield 77%, MS: [M+H] + =733)

[0384] Synthesis Example 46

[0385]

[0386] Under a nitrogen atmosphere, amine 46 (10 g, 22.5 mmol), compound 46-1 (8.9 g, 23.6 mmol), sodium tert-butoxide (2.8 g, 29.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 46. (Yield 80%, MS: [M+H] + =785)

[0387] Synthesis Example 47

[0388]

[0389] Under a nitrogen atmosphere, amine 47 (10 g, 29.7 mmol), compound 47-1 (11.7 g, 31.2 mmol), sodium tert-butoxide (3.7 g, 38.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound 47. (Yield 69%, MS: [M+H] + =676)

[0390] Synthesis Example 48

[0391]

[0392] Under a nitrogen atmosphere, amine 48 (10 g, 25.2 mmol), compound 48-1 (10 g, 26.4 mmol), sodium tert-butoxide (3.1 g, 32.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 48. (Yield 71%, MS: [M+H] + =741)

[0393] Synthesis Example 49

[0394]

[0395] Under a nitrogen atmosphere, amine 49 (10 g, 24.1 mmol), compound 49-1 (9.4 g, 25.3 mmol), sodium tert-butoxide (3 g, 31.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 49. (Yield 62%, MS: [M+H] + =752)

[0396] Synthesis Example 50

[0397]

[0398] Under a nitrogen atmosphere, amine 50 (10 g, 21.1 mmol), compound 50-1 (8.4 g, 22.2 mmol), sodium tert-butoxide (2.6 g, 27.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 50. (Yield 76%, MS: [M+H] + =817)

[0399] Synthesis Example 51

[0400]

[0401] Under a nitrogen atmosphere, amine 51 (10 g, 21.2 mmol), compound 51-1 (8.3 g, 22.2 mmol), sodium tert-butoxide (2.6 g, 27.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 51. (Yield 64%, MS: [M+H] + =808)

[0402] Synthesis example 52

[0403]

[0404] Under a nitrogen atmosphere, amine 52 (10 g, 30.1 mmol), compound 52-1 (13.5 g, 31.6 mmol), sodium tert-butoxide (3.8 g, 39.1 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 16.1 g of compound 52. (Yield 74%, MS: [M+H] + =726)

[0405] Synthesis example 53

[0406]

[0407] Under a nitrogen atmosphere, amine 53 (10 g, 21.2 mmol), compound 53-1 (8.4 g, 22.2 mmol), sodium tert-butoxide (2.6 g, 27.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 53. (Yield 68%, MS: [M+H] + =815)

[0408] Synthesis example 54

[0409]

[0410] Under a nitrogen atmosphere, amine 54 (10 g, 29.9 mmol), compound 54-1 (11.8 g, 31.4 mmol), and sodium tert-butoxide (3.7 g, 38.9 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 54. (Yield 65%, MS: [M+H] + =700)

[0411] Synthesis Example 55

[0412]

[0413] Under a nitrogen atmosphere, amine 55 (10 g, 27.4 mmol), compound 55-1 (10.7 g, 28.8 mmol), and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of compound 55. (Yield 70%, MS: [M+H] + =701)

[0414] Synthesis example 56

[0415]

[0416] Under a nitrogen atmosphere, amine 56 (10 g, 24.2 mmol), compound 56-1 (9.5 g, 25.4 mmol), and sodium tert-butoxide (3 g, 31.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound 56. (Yield 68%, MS: [M+H] + =751)

[0417] Synthesis Example 57

[0418]

[0419] Under a nitrogen atmosphere, amine 57 (10 g, 31.1 mmol), compound 57-1 (12.1 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 57. (Yield 60%, MS: [M+H] + =657)

[0420] Synthesis example 58

[0421]

[0422] Under a nitrogen atmosphere, amine 58 (10 g, 25.9 mmol), compound 58-1 (10.2 g, 27.2 mmol), and sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 58. (Yield 75%, MS: [M+H] + =728)

[0423] Synthesis Example 59

[0424]

[0425] Under a nitrogen atmosphere, amine 59 (10 g, 22.5 mmol), compound 59-1 (8.7 g, 23.6 mmol), sodium tert-butoxide (2.8 g, 29.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 59. (Yield 75%, MS: [M+H] + =778)

[0426] Synthesis Example 60

[0427]

[0428] Under a nitrogen atmosphere, amine 60 (10 g, 31.1 mmol), compound 60-1 (12.2 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 60. (Yield 68%, MS: [M+H] + =661)

[0429] Synthesis Example 61

[0430]

[0431] Under a nitrogen atmosphere, amine 61 (10 g, 25.8 mmol), compound 61-1 (10.2 g, 27.1 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 61. (Yield 65%, MS: [M+H] + =727)

[0432] Synthesis example 62

[0433]

[0434] Under a nitrogen atmosphere, amine 62 (10 g, 31.1 mmol), compound 62-1 (12 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound 62. (Yield 70%, MS: [M+H] + =654)

[0435] Synthesis example 63

[0436]

[0437] Under a nitrogen atmosphere, amine 63 (10 g, 25.5 mmol), compound 63-1 (10 g, 26.8 mmol), sodium tert-butoxide (3.2 g, 33.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 63. (Yield 77%, MS: [M+H] + =729)

[0438] Synthesis Example 64

[0439]

[0440] Under a nitrogen atmosphere, amine 64 (10 g, 31.1 mmol), compound 64-1 (12.1 g, 32.7 mmol), and sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 15.3 g of compound 64. (Yield 75%, MS: [M+H] + =657)

[0441] Synthesis Example 65

[0442]

[0443] Under a nitrogen atmosphere, amine 65 (10 g, 29.7 mmol), compound 65-1 (11.4 g, 31.2 mmol), sodium tert-butoxide (3.7 g, 38.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 65. (Yield 72%, MS: [M+H] + =667)

[0444] Synthesis example 66

[0445]

[0446] Under a nitrogen atmosphere, amine 66 (10 g, 29.4 mmol), compound 66-1 (12.9 g, 30.8 mmol), sodium tert-butoxide (3.7 g, 38.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 66. (Yield 62%, MS: [M+H] + =723)

[0447] Synthesis Example 67

[0448]

[0449] Under a nitrogen atmosphere, amine 67 (10 g, 22.8 mmol), compound 67-1 (8.9 g, 23.9 mmol), sodium tert-butoxide (2.8 g, 29.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 67. (Yield 76%, MS: [M+H] + =778)

[0450] Synthesis example 68

[0451]

[0452] Under a nitrogen atmosphere, amine 68 (10 g, 31.1 mmol), compound 68-1 (12 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 68. (Yield 71%, MS: [M+H] + =653)

[0453] Synthesis example 69

[0454]

[0455] Under a nitrogen atmosphere, amine 69 (10 g, 25.9 mmol), compound 69-1 (10.1 g, 27.2 mmol), sodium tert-butoxide (3.2 g, 33.6 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound 69. (Yield 74%, MS: [M+H] + =724)

[0456] Synthesis Example 70

[0457]

[0458] Under a nitrogen atmosphere, amine 70 (10 g, 23.8 mmol), compound 70-1 (9.2 g, 25 mmol), sodium tert-butoxide (3 g, 30.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 70. (Yield 61%, MS: [M+H] + =753)

[0459] Synthesis Example 71

[0460]

[0461] Under a nitrogen atmosphere, amine 71 (10 g, 31.1 mmol), compound 71-1 (12 g, 32.7 mmol), sodium tert-butoxide (3.9 g, 40.4 mmol) were added to 200 ml of xylene, 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 completed, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The final compound was completely dissolved in chloroform, washed with water twice, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The final concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound 71. (Yield 77%, MS: [M+H] + =652)

[0462] Example 1

[0463] ITO (Indium Tin Oxide) 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.

[0464] 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 Next, as a hole transport auxiliary layer, the compound 1 of the present invention is Next, as a light-emitting layer, the compounds represented by the following chemical formulas BH-1 and BD-1 were deposited at a weight ratio of 25:1 and 1:1. Next, as a hole blocking layer, a compound represented by the following chemical formula HB-1 was deposited in an amount of Next, as a layer for simultaneously performing electron transport and electron injection, a compound represented by the following chemical formula ET-1 and a compound represented by the following LiQ were added at a weight ratio of 1:1 and at a weight ratio of On the electron transport and electron injection layers, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0465]

[0466] Examples 2 to 71

[0467] Except that the compounds described in the following Tables 1 to 4 were used instead of Compound 1, the same method as in Example 1 was carried out to manufacture organic light-emitting devices of Examples 2 to 71, respectively.

[0468] Comparative Examples 1 to 15

[0469] Organic light-emitting devices of Comparative Examples 1 to 15 were manufactured in the same manner as in Example 1 except that the compounds described in Table 5 below were used instead of Compound 1.

[0470] On the other hand, the structures of compounds C-1 to C-15 used in Comparative Examples 1 to 15 are shown below.

[0471]

[0472] Experimental example

[0473] The organic light-emitting devices manufactured in the above-mentioned Examples 1 to 71 and Comparative Examples 1 to 15 were respectively measured by applying 15 mA / cm 2 The voltage, efficiency and life T95 at the current are shown in the following Tables 1 to 5.

[0474] On the other hand, the lifetime T95 refers to the time required for the brightness to decrease from the initial brightness (1000 nits) to 95%.

[0475]

Table 1

[0476]

[0477]

Table 2

[0478]

[0479]

Table 3

[0480]

[0481]

Table 4

[0482]

[0483]

Table 5

[0484]

[0485] As shown in Tables 1 to 5 above, the organic light-emitting device of the embodiment using the compound according to the present invention as the hole transport auxiliary layer of the blue light-emitting layer shows an improved effect in terms of driving voltage, efficiency and life compared with the comparative example. In particular, when compared with the comparative example containing the compound not substituted with deuterium, it was confirmed that a significant improvement in life characteristics was shown. It is judged that the above results are due to the fact that the compound according to the present invention contributes to the stability of the excitons formed in the light-emitting layer, so that the characteristics of the organic light-emitting device are greatly improved.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Ar1 and Ar2 are each independently 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, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene, R is substituted or unsubstituted C 6-60 Aryl, D a and D b It means D a and D b The number of deuterium substitutions in the benzene ring of the phenanthryl group to which each is bonded, a and b are each independently an integer from 0 to 4, wherein, 0 <a+b≤8, D m refers to the number of deuterium substitutions in the phenylene group, m is an integer from 0 to 4, D n It refers to the number of deuterium substitutions in a compound, where n is an integer greater than 1.

2. The compound according to claim 1, wherein The chemical formula 1 is represented by the following chemical formula 1-1: [Chemical formula 1-1] In the chemical formula 1-1, Ar1, Ar2, L1, L2, R, D a , D b , D m , D n , a, b, m and n are the same as defined in claim 1.

3. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, (phenyl)naphthyl or (naphthyl)phenyl, The Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuterium groups.

4. The compound according to claim 1, wherein Ar1 and Ar2 are each independently any one of the following groups, The Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuteriums:

5. The compound according to claim 1, wherein L1 and L2 are each independently a single bond; or phenylene, biphenylene or naphthalene diyl, The phenylene group, biphenylene group and naphthalenediyl group are each independently unsubstituted or substituted with one or more deuterium groups.

6. The compound according to claim 1, wherein L1 and L2 are each independently a single bond, or any one of the following formulae: In the formula, D p1 To D p28 It refers to the number of deuterium substitutions, and p1 to p28 are each independently an integer greater than or equal to 0.

7. The compound according to claim 1, wherein R is phenyl or naphthyl, The R is unsubstituted or substituted with one or more deuteriums.

8. The compound according to claim 1, wherein R is any one of the following groups, The R is unsubstituted or substituted by one or more deuteriums:

9. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the following chemical formulas: In the chemical formula, D m refers to the number of deuterium substitutions in the phenylene group, m is an integer from 0 to 4, D n1 , D n2 , D n3 , D n4 , D n5 , D n6 , D n7 and D n8 refers to the number of deuterium substitutions in each compound. n1 is an integer greater than 1, n2 is an integer greater than or equal to 2, n3 is an integer greater than or equal to 3, n4 is an integer greater than or equal to 4, n5 is an integer greater than or equal to 5, n6 is an integer greater than or equal to 6, n7 is an integer greater than or equal to 7, n8 is an integer greater than or equal to 8.

10. An organic light emitting device, wherein: include: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 9.

11. The organic light emitting device according to claim 10, wherein: The organic layer containing the compound is a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, or an electron transport and electron injection layer.

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