Organic light emitting device

Abstract

An organic light emitting device is provided. The organic light-emitting device includes an anode, a cathode provided facing the anode, and a light-emitting layer provided between the anode and the cathode, the light-emitting layer containing a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2. The organic light-emitting device comprises two host compounds in the light-emitting layer, so that the efficiency, the driving voltage and / or the life characteristic of the organic light-emitting device can be improved.

Description

Technical Field

[0001] The present invention relates to organic light emitting devices. 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 organic light emitting devices.

[0010] Solution to the problem

[0011] The present invention provides the following organic light-emitting device:

[0012] Including: anode,

[0013] a cathode disposed opposite to the anode, and

[0014] A light-emitting layer is provided between the anode and the cathode,

[0015] The light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

[0016] [Chemical formula 1]

[0017]

[0018] In the above chemical formula 1,

[0019] L1 to L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0020] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0021] R is hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl,

[0022] k is an integer from 0 to 7,

[0023] [Chemical formula 2]

[0024]

[0025] In the above chemical formula 2,

[0026] X1 and X2 are each independently O or S,

[0027] A1 and A2 are each independently a naphthalene ring fused to an adjacent five-membered ring,

[0028] L'1 to L'3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0029] Ar' is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0030] R'1 and R'2 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl,

[0031] a and b are each independently an integer from 0 to 9.

[0032] Effects of the Invention

[0033] The organic light-emitting device mentioned above comprises two host compounds in the light-emitting layer, thereby improving the efficiency, driving voltage and / or life characteristics of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 is shown.

[0035] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown.

[0036] Explanation of symbols

[0037] 1: Substrate 2: Anode

[0038] 3: Light-emitting layer 4: Cathode

[0039] 5: Hole injection layer 6: Hole transport layer

[0040] 7: Electron blocking layer 8: Hole blocking layer

[0041] 9: Electron injection and transport layer DETAILED DESCRIPTION

[0042] In the following, the present invention will be described in more detail to help understanding the present invention.

[0043] (Definition of terms)

[0044] In this manual, "D" represents a bond to other substituents, and "D" represents deuterium.

[0045] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano 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" can be a biphenyl group. That is, a biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups. As an example, the term "substituted or unsubstituted" can be understood as "unsubstituted or substituted with a substituent selected from deuterium, halogen, cyano, silyl, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20The term "substituted with one or more substituents in an aryl group" may be understood as "substituted with one to the maximum number of replaceable hydrogen atoms". Alternatively, the term "substituted with one or more substituents" may be understood as "substituted with one to five substituents" or "substituted with one or two substituents".

[0046] 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 substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0047]

[0048] 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 substituents may be of the following structural formulas, but are not limited thereto.

[0049]

[0050] 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 substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0051]

[0052] In this specification, silyl refers to -Si(Z1)(Z2)(Z3), wherein Z1, Z2 and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 1-60 Haloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 haloalkenyl, or substituted or unsubstituted C 6-60 According to one embodiment, Z1, Z2 and Z3 can each independently be hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20 Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0053] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0054] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0055] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, 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-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl and the like, but are not limited thereto.

[0056] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0057] In this specification, the alicyclic group refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound containing only carbon as a ring atom and not having aromaticity, and is understood to include all monocyclic or condensed polycyclic compounds. According to one embodiment, the alicyclic group has 3 to 60 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl, bridged hydrocarbon groups, spirohydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, and the like.

[0058] Specifically, examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl, but are not limited thereto.

[0059] Examples of the bridged cyclic hydrocarbon group include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, and decalinyl.

[0060] In addition, examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited to these.

[0061] The substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds are substituents derived from compounds obtained by hydrogenating some unsaturated bonds of monocyclic or polycyclic aromatic hydrocarbon compounds. Examples of such substituents include, but are not limited to, 1H-indenyl, 2H-indenyl, 4H-indenyl, 2,3-dihydro-1H-indenyl, 1,4-dihydronaphthyl, 1,2,3,4-tetrahydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl and 6,7-dihydro-5H-benzocycloheptenyl.

[0062] In the present specification, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound containing only carbon as a ring atom and having aromaticity. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 60. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 20. Regarding the above aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the above polycyclic aryl group, it can be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0063] 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.

[0064] In this specification, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound containing one or more heteroatoms selected from O, N, Si and S as ring atoms in addition to carbon, and is understood to include all substituents having aromaticity or substituents not having aromaticity. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 60. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of such heterocyclic groups include heteroaryl groups, substituents derived from hydrogenated derivatives of heteroaromatic compounds, and the like.

[0065] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound containing one or more heteroatoms selected from N, O and S as ring atoms in addition to carbon, and refers to a substituent having aromaticity. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 60. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 20. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 12. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 10. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 8. Examples of the heteroaryl group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline, isothiophene Examples of the present invention include, but are not limited to, oxazolyl, thiadiazolyl, and phenothiazinyl.

[0066] The substituent derived from a hydrogenated derivative of a heteroaromatic compound refers to a substituent derived from a compound obtained by hydrogenating a portion of unsaturated bonds of a monocyclic or polycyclic heteroaromatic compound. Examples of such substituents include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0067] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl is the same as the aryl group exemplified above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the alkyl group exemplified above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above description of heteroaryl. In the present specification, the alkenyl group in aralkenyl is the same as the alkenyl group exemplified above. In the present specification, the arylene group is a divalent group, and the above description of aryl can be applied otherwise. In the present specification, the heteroarylene group is a divalent group, and the above description of heteroaryl can be applied otherwise. In the present specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above description of aryl or cycloalkyl can be applied otherwise. In the present specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above description of heteroaryl can be applied otherwise.

[0068] In the present specification, "deuterated or substituted with deuterium" means that at least one of the replaceable hydrogen atoms in a compound, a divalent linking group or a monovalent substituent is substituted with deuterium.

[0069] In addition, "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with one to a maximum of substitutable hydrogen atoms being substituted with deuterium". As an example, the term "phenanthryl group unsubstituted or substituted with deuterium" can be understood to mean "phenanthryl group unsubstituted or substituted with one to nine deuterium atoms" when considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the structure of the phenanthryl group is nine.

[0070] In addition, the meaning of "deuterated structure" refers to compounds, divalent linking groups or monovalent substituents including all structures in which at least one hydrogen is replaced by deuterium. As an example, the deuterated structure of phenyl shown below can be understood as referring to all structures in which at least one substitutable hydrogen in phenyl is replaced by deuterium and monovalent substituents.

[0071]

[0072] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to the value calculated as a percentage of the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist (the sum of the number of hydrogen that can be substituted with deuterium in the compound and the number of deuterium substituted). Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogen that can be substituted with deuterium in the compound is substituted with deuterium.

[0073] In this case, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be measured by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry) or GC / MS (Gas Chromatography / Mass Spectrometry), etc., and are measured according to commonly known methods. More specifically, when MALDI-TOF MS is used, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be determined by analyzing the number of deuterium substituted in the compound through MALDI-TOF MS, and then calculating the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist as a percentage.

[0074] An organic light-emitting device is provided, comprising: an anode; a cathode disposed opposite to the anode; and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by the chemical formula 1 and a second compound represented by the chemical formula 2.

[0075] The organic light-emitting device according to the present invention comprises two compounds having specific structures as host substances in the light-emitting layer, thereby improving the efficiency, driving voltage and / or life characteristics of the organic light-emitting device.

[0076] Hereinafter, the present invention will be described in detail according to each structure.

[0077] Anode and cathode

[0078] 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.

[0079] 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.

[0080] Hole injection layer

[0081] The organic light emitting device according to the present invention may include a hole injection layer between the anode and the hole transport layer described below as necessary.

[0082] The hole injection layer is located on the anode, is a layer for injecting holes from the anode, and contains a hole injection substance. As such a hole injection substance, it is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film forming ability. In particular, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection substance is between the work function of the anode substance and the HOMO of the surrounding organic layer.

[0083] Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited to these.

[0084] Hole transport layer

[0085] The organic light-emitting device according to the present invention may include a hole transport layer between the anode and the light-emitting layer. The hole transport layer is a layer that receives holes from the anode or the hole injection layer formed on the anode and transports the holes to the light-emitting layer, and contains a hole transport substance. The hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is suitable for substances with high hole mobility. As specific examples, there are aromatic amine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited to these.

[0086] Electron blocking layer

[0087] The organic light-emitting device according to the present invention may include an electron blocking layer between the hole transport layer and the light-emitting layer as required. The electron blocking layer refers to a layer formed on the hole transport layer, preferably arranged in contact with the light-emitting layer, and improving the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing the excessive migration of electrons to increase the probability of hole-electron bonding. The electron blocking layer contains an electron blocking substance. As an example of such an electron blocking substance, an arylamine-based organic substance can be used, but it is not limited to this.

[0088] Luminescent layer

[0089] The organic light-emitting device according to the present invention includes a light-emitting layer between an anode and a cathode, and the light-emitting layer includes the first compound and the second compound as host substances. Specifically, the first compound functions as an N-type host substance having a better electron transport capability than a hole transport capability, and the second compound functions as a P-type host substance having a better hole transport capability than an electron transport capability, thereby appropriately maintaining the ratio of holes and electrons in the light-emitting layer. Therefore, the excitons emit light uniformly throughout the light-emitting layer, thereby simultaneously improving the luminous efficiency and life characteristics of the organic light-emitting device.

[0090] Next, the first compound and the second compound are described in order.

[0091] (First Compound)

[0092] The first compound is represented by the chemical formula 1. Specifically, the first compound is a compound in which one triazine group is substituted in dibenzofuran, has excellent electron transport capability, and effectively transfers electrons to the dopant substance, thereby increasing the electron-hole recombination probability in the light-emitting layer.

[0093] On the other hand, the specific binding position of L3 in the above chemical formula 1 can be represented by the following chemical formula 1':

[0094] [Chemical Formula 1']

[0095]

[0096] In the above chemical formula 1',

[0097] L3 is linked to one of the carbon at the *1 position, the carbon at the *2 position, the carbon at the *3 position, and the carbon at the *4 position,

[0098] L1 to L3, Ar1, Ar2, R and k are the same as defined in the above Chemical Formula 1.

[0099] For example, the above Chemical Formula 1 can be represented by the following Chemical Formula 1-1:

[0100] [Chemical formula 1-1]

[0101]

[0102] In the above chemical formula 1-1,

[0103] L1 to L3, Ar1, Ar2, R and k are the same as defined in the above Chemical Formula 1.

[0104] In one embodiment, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0105] In another specific example, L1 and L2 are each independently a single bond; or a C 6-20 Arylene.

[0106] In another specific example, L1 and L2 can each independently be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0107] In another specific example, L1 and L2 can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0108] In another specific example, L1 and L2 are each independently a single bond, a phenylene group, a biphenylene group or a naphthylene group,

[0109] The above-mentioned phenylene group, biphenyldiyl group and naphthylene group may be unsubstituted or substituted with deuterium.

[0110] For example, L1 and L2 can each independently be a single bond, or any one selected from the following groups and their deuterated structures:

[0111]

[0112] In addition, L1 and L2 may be the same as each other. Alternatively, L1 and L2 may be different.

[0113] For example, L1 and L2 may both be single bonds; or

[0114] One of L1 and L2 may be a single bond, and the other may be a phenylene group which may be substituted by deuterium or a naphthylene group which may be substituted by deuterium or not.

[0115] In one specific example, L3 can be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0116] In another specific example, L3 may be a single bond; or a C 6-20 Arylene.

[0117] In another specific example, L3 may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0118] For example, L3 may be a single bond or any one of the divalent linking groups represented by the following chemical formulae 4a to 4m:

[0119]

[0120] In the above chemical formulae 4a to 4m,

[0121] D stands for deuterium,

[0122] p is an integer from 0 to 6,

[0123] q is an integer from 0 to 4.

[0124] In other words, in the above chemical formulas 4a to 4m,

[0125] p is 0, 1, 2, 3, 4, 5 or 6,

[0126] q is 0, 1, 2, 3 or 4.

[0127] In one embodiment, Ar1 and Ar2 may be substituted or unsubstituted C 6-20 Aryl.

[0128] In another embodiment, Ar1 and Ar2 are each independently unsubstituted or selected from deuterium, deuterium-substituted or unsubstituted C 1-10 Alkyl, deuterium-substituted or unsubstituted C 6-20 Aryl, -Si (C substituted or unsubstituted by deuterium 1-10 alkyl)3, and -Si (C 6-20aryl)3 substituted with one or more substituents 6-20 Aryl.

[0129] Among them, Si (C substituted or unsubstituted by deuterium) 1-10 Alkyl)3 and -Si (C 6-20 The three substituents bonded to Si in the aryl group)3 may be the same as or different from each other.

[0130] Specifically, for example, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,

[0131] Wherein, Ar1 and Ar2 may be unsubstituted or substituted by one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, and -Si(phenyl substituted or unsubstituted by deuterium)3.

[0132] For example, Ar1 and Ar2 can each independently be any one selected from the following groups and their deuterated structures:

[0133]

[0134]

[0135] In one embodiment, Ar1 and Ar2 may be identical to each other. Alternatively, Ar1 and Ar2 may be different.

[0136] In another specific example, L1-Ar1 and L2-Ar2 may be the same as each other.

[0137] Alternatively, L1-Ar1 and L2-Ar2 may be different.

[0138] In addition, in one specific example, R can be deuterium, halogen, methyl or ethyl.

[0139] Here, k represents the number of R. When k is 2 or more, the two or more Rs may be the same or different from each other. Specifically, k is 0, 1, 2, 3, 4, 5, 6 or 7.

[0140] For example, k may be 0; or

[0141] k may be greater than 1, and R may be deuterium.

[0142] In addition, the first compound may contain no deuterium, or may contain one or more deuteriums.

[0143] When the first compound contains deuterium, the deuterium substitution rate of the first compound may be 1% to 100%. Specifically, the deuterium substitution rate of the first compound may be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, or 90% or more and 100% or less.

[0144] As an example, the first compound may not contain deuterium, or may contain 1 to 50 deuteriums. More specifically, the first compound may not contain deuterium, or may contain 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more and 50 or less, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 13 or less, 12 or less, 11 or less, or 10 or less deuteriums.

[0145] At this time, when expressing the number of deuterium substitutions in the first compound, it can be represented by the following chemical formula 1D:

[0146] [Chemical formula 1D]

[0147]

[0148] In the above chemical formula 1D,

[0149] Dn means n hydrogens are replaced by deuterium.

[0150] Wherein, n is an integer greater than 0,

[0151] L 1a To L 3a ,Ar 1a ,Ar 2a and R a represent L1 to L3, Ar1, Ar2 and R substituents which are not substituted by deuterium, respectively.

[0152] On the other hand, representative examples of the above-mentioned first compound are shown below:

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] On the other hand, the first compound can be prepared by the preparation method shown in the following reaction formula 1:

[0192] [Reaction 1]

[0193]

[0194] In the above reaction formula 1, Y is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as described above.

[0195] Specifically, the first compound can be manufactured by Suzuki-coupling reaction of starting materials A1 and A2. Such Suzuki-coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the Suzuki reaction can be appropriately changed. The manufacturing method of the first compound can be more specifically described in the manufacturing example described later.

[0196] (Second Compound)

[0197] The second compound is represented by the chemical formula 2. Specifically, the second compound is a tertiary amine compound having two benzonaphthofuranyl / benzonaphthothienyl substituents, and the compound has a structure in which one of the benzonaphthofuranyl / benzonaphthothienyl substituents is connected to the nitrogen atom of the amino group via a benzene ring, and the other of the benzonaphthofuranyl / benzonaphthothienyl substituents is connected to the nitrogen atom of the amino group via a naphthalene ring. The compound represented by the chemical formula 2 having the structure as described above can effectively transfer holes to the dopant substance, and thus can increase the recombination probability of holes and electrons in the light-emitting layer together with the first compound having excellent electron transport ability.

[0198] On the other hand, the second compound may be represented by any one of the following chemical formulas 1A to 1C according to the fusion position of the A1 ring:

[0199] [Chemical Formula 1A]

[0200]

[0201] [Chemical formula 1B]

[0202]

[0203] [Chemical formula 1C]

[0204]

[0205] In the above chemical formulas 1A to 1C,

[0206] L1 is linked to one of the carbon at the *1 position, the carbon at the *2 position, the carbon at the *3 position, the carbon at the *4 position, the carbon at the *5 position, and the carbon at the *6 position,

[0207] X1, X2, A2, L'1 to L'3, Ar', R'1, R'2, a and b are the same as defined in the above Chemical Formula 1.

[0208] In one specific example, X1 and X2 may both be 0; or

[0209] X1 and X2 can both be S; or

[0210] X1 may be O, X2 may be S; or

[0211] X1 may be S, and X2 may be O.

[0212] In a specific example, the second compound can be represented by the following chemical formula 2-1:

[0213] [Chemical formula 2-1]

[0214]

[0215] In the above chemical formula 2-1,

[0216] A'1 is a benzene ring fused with an adjacent five-membered ring and a benzene ring,

[0217] X1, X2, A2, L'1 to L'3, Ar', R'1, R'2, a and b are the same as defined in the above Chemical Formula 1.

[0218] In a specific example, It may be any one of the substituents represented by the following chemical formulas 2a to 21:

[0219]

[0220] In the above chemical formulae 2a to 21,

[0221] X1, R'1 and a are the same as defined in the above Chemical Formula 1.

[0222] In addition, in one specific example, It may be any one of the substituents represented by the following chemical formulas 3a to 31:

[0223]

[0224] In the above chemical formulae 3a to 31,

[0225] X2, R'2 and b are the same as defined in the above Chemical Formula 1.

[0226] In one specific example, L'1 and L'2 are each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0227] In another specific example, L'1 and L'2 are each independently a single bond; or a C substituted with one or more substituents selected from deuterium, phenyl and naphthyl. 6-20 Arylene.

[0228] In another specific example, L'1 and L'2 can each independently be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0229] In another specific example, L'1 and L'2 can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0230] In another specific example, L'1 and L'2 are each independently a single bond, a phenylene group, a biphenylene group, or a naphthylene group,

[0231] The above-mentioned phenylene group, biphenyldiyl group and naphthylene group may be unsubstituted or substituted with deuterium.

[0232] For example, L'1 and L'2 can each independently be a single bond, or any one selected from the following groups and their deuterated structures:

[0233]

[0234] More specifically, for example, L'1 and L'2 may each independently be a single bond, or a substituted or unsubstituted 1,4-phenylene group.

[0235] In another specific example, at least one of L'1 and L'2 may be a single bond.

[0236] At this time, L'1 and L'2 may be the same as each other, or L'1 and L'2 may be different.

[0237] For example, L'1 and L'2 may both be single bonds; or

[0238] L'1 can be a single bond, and L'2 can be a substituted or unsubstituted C 6-12 an arylene group; or

[0239] L'1 can be substituted or unsubstituted C 6-12 In the arylene group, L'2 may be a single bond.

[0240] For example, L'1 and L'2 may both be single bonds; or

[0241] L'1 can be a single bond, and L'2 can be a substituted or unsubstituted C 6-10 an arylene group; or

[0242] L'1 can be substituted or unsubstituted C 6-10 In the arylene group, L'2 may be a single bond.

[0243] In one specific example, L'3 can be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0244] In another specific example, L'3 may be a single bond; or a C '3 which is unsubstituted or substituted with one or more substituents selected from deuterium, phenyl and naphthyl. 6-20 Arylene.

[0245] In another specific example, L'3 can be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0246] For example, L'3 may be a single bond, or a substituted or unsubstituted phenylene group.

[0247] In one specific example, Ar' can be a substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C containing a heteroatom of O or S 2-20 Heteroaryl.

[0248] In another specific example, Ar' is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,

[0249] Here, Ar' may be substituted or unsubstituted.

[0250] In another specific example, Ar' is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,

[0251] Ar' may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

[0252] For example, Ar' may be any one selected from the following groups and their deuterated structures, but is not limited thereto:

[0253]

[0254]

[0255] Here, a represents the number of R'1, and when a is 2 or more, the two or more R'1 may be the same or different. Specifically, a is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0256] In addition, b represents the number of R'2, and when b is 2 or more, the two or more R'2 may be the same or different. Specifically, b is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0257] For example, R'1 and R'2 may both be hydrogen, or may both be deuterium.

[0258] In addition, the second compound may be represented by any one of the following chemical formulas 2-1 to 2-9:

[0259] [Chemical formula 2-1]

[0260]

[0261] [Chemical formula 2-2]

[0262]

[0263] [Chemical formula 2-3]

[0264]

[0265] [Chemical formula 2-4]

[0266]

[0267] [Chemical formula 2-5]

[0268]

[0269] [Chemical formula 2-6]

[0270]

[0271] [Chemical formula 2-7]

[0272]

[0273] [Chemical formula 2-8]

[0274]

[0275] [Chemical formula 2-9]

[0276]

[0277] In the above chemical formulas 2-1 to 2-9,

[0278] X1, X2, L'1 to L'3, Ar', R'1, R'2, a and b are the same as defined in the above Chemical Formula 1.

[0279] In addition, the second compound may contain no deuterium, or may contain one or more deuteriums.

[0280] When the second compound contains deuterium, the deuterium substitution rate of the second compound may be 1% to 100%. Specifically, the deuterium substitution rate of the second compound may be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, or 90% or more and 100% or less.

[0281] As an example, the second compound may not contain deuterium, or may contain 1 to 50 deuteriums. More specifically, the second compound may not contain deuterium, or may contain 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more and 50 or less, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 13 or less, 12 or less, 11 or less, or 10 or less deuteriums.

[0282] At this time, when expressing the number of deuterium substitutions in the second compound, it can be represented by the following chemical formula 2D:

[0283] [Chemical Formula 2D]

[0284]

[0285] In the above chemical formula 2D,

[0286] Dn means n hydrogens are replaced by deuterium.

[0287] Wherein, n is an integer greater than 0,

[0288] L' 1aTo L' 3a ,Ar' a , R' 1a and R' 2a represent L'1 to L'3, Ar', R'1 and R'2 substituents which are not substituted by deuterium, respectively.

[0289] On the other hand, representative examples of the second compound are shown below:

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] Among the above compounds,

[0317] Dn means n hydrogens are replaced by deuterium.

[0318] Here, n is an integer greater than or equal to 1.

[0319] On the other hand, as an example, the second compound can be produced by the production method shown in the following reaction formula 2:

[0320] [Reaction 2]

[0321]

[0322] In the above reaction formula 2, Y' is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as described above.

[0323] Specifically, the second compound can be produced by an amine substitution reaction of starting materials B1 and B2. Such an amine substitution reaction 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 appropriately changed. The production method of the second compound can be more specifically described in the production example described later.

[0324] In addition, the first compound and the second compound may be contained in the light-emitting layer at a weight ratio of 1:99 to 99:1. In this case, in order to appropriately maintain the ratio of holes to electrons in the light-emitting layer, the first compound and the second compound are more preferably contained in a weight ratio of 10:90 to 50:50, or 20:80 to 40:60. Preferably, the first compound and the second compound may be contained in the light-emitting layer at a weight ratio of 30:70.

[0325] On the other hand, the above-mentioned light-emitting layer may contain a dopant substance in addition to the above-mentioned two main substances. Such dopant substances include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic condensed ring derivatives having substituted or unsubstituted arylamino groups, and include 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.

[0326] More specifically, as the dopant material, the following compounds may be used, but are not limited thereto:

[0327]

[0328]

[0329]

[0330]

[0331] Hole blocking layer

[0332] The organic light-emitting device according to the present invention may include a hole blocking layer between the light-emitting layer and the electron transport layer described later as needed. The hole blocking layer refers to a layer formed on the light-emitting layer, preferably arranged in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. As examples of such a hole blocking substance, azine derivatives containing triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0333] Electron injection and transport layer

[0334] The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and plays the role of both the electron transport layer and the electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such electron injection and transport substances are substances that can well receive electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. As specific examples of electron injection and transport substances, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc. can be used, but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

[0335] The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and as the electron transport material contained in the electron transport layer, the electron injection and transport material mentioned above can be used. In addition, the electron injection layer is formed on the electron transport layer, and as the electron injection material contained in the electron injection layer, LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal coordination compounds and nitrogen-containing five-membered ring derivatives, etc.

[0336] 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-hydroxyquinoline) gallium chloride, bis(2-methyl-8-hydroxyquinoline)(o-cresol) gallium, bis(2-methyl-8-hydroxyquinoline)(1-naphthol) aluminum, and bis(2-methyl-8-hydroxyquinoline)(2-naphthol) gallium.

[0337] Organic light-emitting devices

[0338] The structure of the organic light emitting device according to the present invention is shown in Figure 1 and 2 . 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 first compound and the second compound may be contained in the light-emitting layer.

[0339] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown.

[0340] In the above structure, the first compound and the second compound may be included in the light-emitting layer.

[0341] The organic light-emitting device according to the present invention can be manufactured by stacking the above-mentioned structures in sequence. In this case, it can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation (e-beam evaporation) to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then form the above-mentioned layers on the anode, and then vapor-deposit a substance that can be used as a cathode thereon to manufacture. In addition to this method, an organic light-emitting device can also be manufactured by vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate in sequence. In addition, not only a vacuum evaporation method but also a solution coating method can be used to form a main body and a dopant into a light-emitting layer. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to this.

[0342] 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.

[0343] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a bidirectional light-emitting device, and in particular, may be a bottom emission device requiring relatively high light-emitting efficiency.

[0344] The preparation of the compound represented by the above Chemical Formula 1, the compound represented by the above Chemical Formula 2, 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.

[0345] [Production of the compound represented by Chemical Formula 1]

[0346] Synthesis example 1-1

[0347]

[0348] Trz1 (15 g, 28.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.4 g, 30.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12 g, 86.5 mmol) was then dissolved in 36 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of compound 1-1. (yield 65%, MS: [M+H] + =652)

[0349] Synthesis example 1-2

[0350]

[0351] Trz2 (15 g, 30.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.8 g, 31.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.6 g, 91.1 mmol) was dissolved in 38 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound 1-2. (Yield 74%, MS: [M+H] + =626)

[0352] Synthesis Example 1-3

[0353]

[0354] Trz3 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 1-3. (Yield 69%, MS: [M+H] + =576)

[0355] Synthesis Example 1-4

[0356]

[0357] Trz4 (15 g, 30.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.8 g, 31.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.6 g, 91.1 mmol) was dissolved in 38 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-4. (Yield 70%, MS: [M+H] + =626)

[0358] Synthesis Example 1-5

[0359]

[0360] Trz5 (15 g, 24.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (5.5 g, 26.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (10.3 g, 74.7 mmol) was dissolved in 31 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6 g of compound 1-5. (Yield 69%, MS: [M+H] + =734)

[0361] Synthesis Example 1-6

[0362]

[0363] Trz6 (15 g, 30.2 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.7 g, 31.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.5 g, 90.7 mmol) was dissolved in 38 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound 1-6. (Yield 66%, MS: [M+H] + =629)

[0364] Synthesis Example 1-7

[0365]

[0366] Trz7 (15 g, 36.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (8.2 g, 38.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of compound 1-7. (Yield 75%, MS: [M+H] + =540)

[0367] Synthesis Example 1-8

[0368]

[0369] Trz8 (15 g, 35.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (8 g, 37.7 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 1-8. (Yield 70%, MS: [M+H] + =550)

[0370] Synthesis Example 1-9

[0371]

[0372] Trz9 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of compound 1-9. (Yield 70%, MS: [M+H] + =576)

[0373] Synthesis Example 1-10

[0374]

[0375] Trz10 (15 g, 35.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (8 g, 37.7 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 1-10. (Yield 70%, MS: [M+H] + =550)

[0376] Synthesis Example 1-11

[0377]

[0378] Trz11 (15 g, 30.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.8 g, 31.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.6 g, 91.1 mmol) was dissolved in 38 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.7 g of compound 1-11. (Yield 72%, MS: [M+H] + =626)

[0379] Synthesis Example 1-12

[0380]

[0381] Trz12 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-12. (Yield 73%, MS: [M+H] + =576)

[0382] Synthesis Example 1-13

[0383]

[0384] Trz13 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 1-13. (Yield 69%, MS: [M+H] + =576)

[0385] Synthesis Example 1-14

[0386]

[0387] Trz14 (15 g, 31.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.1 g, 33.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-14. (Yield 74%, MS: [M+H] + =602)

[0388] Synthesis Example 1-15

[0389]

[0390] Trz15 (15 g, 35.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.9 g, 37.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.7 g, 106.2 mmol) was dissolved in 44 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 1-15. (Yield 73%, MS: [M+H] + =556)

[0391] Synthesis Example 1-16

[0392]

[0393] Trz16 (15 g, 32.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.3 g, 34.4 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.6 g, 98.3 mmol) was dissolved in 41 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 1-16. (Yield 74%, MS: [M+H] + =590)

[0394] Synthesis Example 1-17

[0395]

[0396] Trz17 (15 g, 30 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.7 g, 31.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound 1-17. (Yield 74%, MS: [M+H] + =632)

[0397] Synthesis Example 1-18

[0398]

[0399] Trz18 (15 g, 31.6 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7 g, 33.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.1 g, 94.7 mmol) was dissolved in 39 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-18. (Yield 74%, MS: [M+H] + =607)

[0400] Synthesis Example 1-19

[0401]

[0402] Trz19 (15 g, 31.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.1 g, 33.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of compound 1-19. (Yield 66%, MS: [M+H] + =602)

[0403] Synthesis Example 1-20

[0404]

[0405] Trz20 (15 g, 34.6 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.7 g, 36.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of compound 1-20. (Yield 71%, MS: [M+H] + =566)

[0406] Synthesis example 1-21

[0407]

[0408] Trz21 (15 g, 33.3 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.4 g, 35 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.8 g, 100 mmol) was dissolved in 41 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of compound 1-21. (Yield 72%, MS: [M+H] + =582)

[0409] Synthesis example 1-22

[0410]

[0411] Trz22 (15 g, 28.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.4 g, 30.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-22. (Yield 71%, MS: [M+H] + =652)

[0412] Synthesis example 1-23

[0413]

[0414] Trz23 (15 g, 28.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.4 g, 30.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.7 g of compound 1-23. (Yield 73%, MS: [M+H] + =652)

[0415] Synthesis Example 1-24

[0416]

[0417] Trz24 (15 g, 28.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.4 g, 30.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6 g of compound 1-24. (Yield 67%, MS: [M+H] + =652)

[0418] Synthesis Example 1-25

[0419]

[0420] Trz25 (15 g, 30 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.7 g, 31.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-25. (Yield 75%, MS: [M+H] + =632)

[0421] Synthesis example 1-26

[0422]

[0423] Trz26 (15 g, 27.5 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.1 g, 28.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (11.4 g, 82.4 mmol) was dissolved in 34 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound 1-26. (Yield 75%, MS: [M+H] + =678)

[0424] Synthesis Example 1-27

[0425]

[0426] Trz27 (15 g, 25 mmol) and dibenzo[b,d]furan-1-ylboronic acid (5.6 g, 26.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (10.4 g, 75 mmol) was dissolved in 31 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6 g of compound 1-27. (Yield 69%, MS: [M+H] + =732)

[0427] Synthesis example 1-28

[0428]

[0429] Trz28 (15 g, 31 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.9 g, 32.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13 g of compound 1-28. (Yield 68%, MS: [M+H] + =616)

[0430] Synthesis example 1-29

[0431]

[0432] Trz29 (15 g, 31 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.9 g, 32.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-29. (Yield 70%, MS: [M+H] + =616)

[0433] Synthesis Example 1-30

[0434]

[0435] Trz30 (15 g, 28.2 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.3 g, 29.7 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (11.7 g, 84.7 mmol) was dissolved in 35 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-30. (Yield 69%, MS: [M+H] + =663)

[0436] Synthesis example 1-31

[0437]

[0438] Trz31 (15 g, 30.7 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.8 g, 32.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.7 g, 92 mmol) was dissolved in 38 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 1-31. (Yield 75%, MS: [M+H] + =621)

[0439] Synthesis example 1-32

[0440]

[0441] Trz32 (15 g, 34.6 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.7 g, 36.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of compound 1-32. (Yield 71%, MS: [M+H] + =566)

[0442] Synthesis example 1-33

[0443]

[0444] Trifluoromethanesulfonic anhydride (24 g, 85 mmol) and deuterium oxide (8.5 g, 424.9 mmol) were added at 0°C and stirred for 5 hours to prepare a solution. 1-bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and deuterium oxide was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained and stirred. After reacting for 5 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.7 g of substance (sub) 1-1-1. (Yield 38%, MS: [M+H] + =248)

[0445] Substance 1-1-1 (15 g, 60.5 mmol) and bis(pinacolato)diboron (16.9 g, 66.5 mmol) were mixed in 300 mL of 1,4-dibromopropane. Reflux and stir in 1,4-dioxane. Then, potassium acetate (8.9 g, 90.7 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The reaction was carried out for 6 hours, cooled to room temperature, and the organic layer was separated by chloroform and water, and then the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of substance 1-1-2. (Yield 75%, MS: [M+H] + =296)

[0446] Substance 1-2-2 (15 g, 50.8 mmol) and Trz33 (26.4 g, 53.4 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21 g of compound 1-33. (Yield 66%, MS: [M+H] + =627)

[0447] Synthesis example 1-34

[0448]

[0449] Substance 1-2-2 (15 g, 50.8 mmol) and Trz34 (23.4 g, 53.4 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.4 g of compound 1-34. (Yield 67%, MS: [M+H] + =572)

[0450] Synthesis example 1-35

[0451]

[0452] At 0°C, trifluoromethanesulfonic anhydride (48 g, 170 mmol) and heavy water (17 g, 849.9 mmol) were added and stirred for 5 hours to prepare a solution. 1-Bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, heated to 140°C, maintained and stirred. After reacting for 8 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6 g of substance 1-2-1. (yield 40%, MS: [M+H] + =249)

[0453] Material 1-2-1 (15 g, 60.2 mmol) and bis(pinacolato)diboron (16.8 g, 66.2 mmol) were mixed in 300 mL of 1,4-dihydro- Reflux and stir in oxane. Then, add potassium acetate (8.9 g, 90.3 mmol), stir well, and then add bis(dibenzylideneacetone)palladium (0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol). React for 4 hours, cool to room temperature, separate the organic layer using chloroform and water, and distill the organic layer. Dissolve it again in chloroform, wash it with water twice, separate the organic layer, add anhydrous magnesium sulfate, filter after stirring, and distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of substance 1-2-2. (Yield 70%, MS: [M+H] + =297)

[0454] Substance 1-2-2 (15 g, 50.6 mmol) and Trz35 (28 g, 53.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21 g, 151.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 1-35. (Yield 70%, MS: [M+H] + =660)

[0455] Synthesis example 1-36

[0456]

[0457] Substance 1-2-2 (15 g, 50.6 mmol) and Trz36 (21.9 g, 53.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21 g, 151.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.5 g of compound 1-36. (Yield 68%, MS: [M+H] + =654)

[0458] Synthesis example 1-37

[0459]

[0460] Substance 1-2-2 (15 g, 50.6 mmol) and Trz37 (21.9 g, 53.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21 g, 151.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.9 g of compound 1-37. (Yield 65%, MS: [M+H] + =546)

[0461] Synthesis example 1-38

[0462]

[0463] Substance 1-2-2 (15 g, 50.6 mmol) and Trz36 (23.1 g, 53.2 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (21 g, 151.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19 g of compound 1-38. (Yield 66%, MS: [M+H] + =568)

[0464] Synthesis example 1-39

[0465]

[0466] At 0°C, trifluoromethanesulfonic anhydride (71.9 g, 255 mmol) and heavy water (25.5 g, 1274.8 mmol) were added and stirred for 5 hours to prepare a solution. 1-Bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, and the temperature was raised to 140°C, and then maintained and stirred. After reacting for 14 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.3 g of substance 1-3-1. (yield 42%, MS: [M+H] + =250)

[0467] Material 1-3-1 (15 g, 60 mmol) and bis(pinacolato)diboron (16.8 g, 66 mmol) were mixed in 300 mL of 1,4-dihydro- Reflux and stir in oxane. Then, add potassium acetate (8.8 g, 90 mmol), stir well, and then add bis(dibenzylideneacetone)palladium (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol). React for 6 hours, cool to room temperature, separate the organic layer using chloroform and water, and distill the organic layer. Dissolve it again in chloroform, wash it with water twice, separate the organic layer, add anhydrous magnesium sulfate, filter after stirring, and distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of substance 1-3-2. (Yield 64%, MS: [M+H] + =298)

[0468] Substance 1-3-2 (15 g, 50.5 mmol) and Trz18 (25.2 g, 53 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 151.4 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.1 g of compound 1-39. (Yield 75%, MS: [M+H] + =610)

[0469] Synthesis Example 1-40

[0470]

[0471] Substance 1-3-2 (15 g, 50.5 mmol) and Trz39 (22.8 g, 53 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 151.4 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.5 g of compound 1-40. (Yield 65%, MS: [M+H] + =565)

[0472] Synthesis example 1-41

[0473]

[0474] Substance 1-3-2 (15 g, 50.5 mmol) and Trz39 (21.1 g, 53 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 151.4 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.8 g of compound 1-39. (Yield 66%, MS: [M+H] + =534)

[0475] Synthesis example 1-42

[0476]

[0477] Substance 1-3-2 (15 g, 50.5 mmol) and Trz41 (29.5 g, 53 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 151.4 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.4 g of compound 1-42. (Yield 70%, MS: [M+H] + =691)

[0478] Synthesis example 1-43

[0479]

[0480] At 0°C, trifluoromethanesulfonic anhydride (95.9 g, 340 mmol) and heavy water (34 g, 1699.8 mmol) were added and stirred for 5 hours to prepare a solution. 1-Bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, and the temperature was raised to 140°C, and then maintained and stirred. After reacting for 20 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.6 g of substance 1-4-1. (yield 37%, MS: [M+H] + =251)

[0481] Material 1-4-1 (15 g, 59.7 mmol) and bis(pinacolato)diboron (16.7 g, 65.7 mmol) were mixed in 300 mL of 1,4-diborane. Reflux and stir in oxane. Then, add potassium acetate (8.8 g, 89.6 mmol), stir well, and then add bis(dibenzylideneacetone)palladium (0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol). React for 5 hours, cool to room temperature, separate the organic layer using chloroform and water, and distill the organic layer. Dissolve it again in chloroform, wash it with water twice, separate the organic layer, add anhydrous magnesium sulfate, filter after stirring, and distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of substance 1-4-2. (Yield 70%, MS: [M+H] + =299)

[0482] Substance 1-4-2 (15 g, 50.3 mmol) and Trz42 (26.1 g, 52.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 150.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 1-43. (Yield 68%, MS: [M+H] + =631)

[0483] Synthesis example 1-44

[0484]

[0485] Substance 1-4-2 (15 g, 50.3 mmol) and Trz43 (24.1 g, 52.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 150.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.2 g of compound 1-44. (Yield 68%, MS: [M+H] + =592)

[0486] Synthesis example 1-45

[0487]

[0488] Substance 1-4-2 (15 g, 50.3 mmol) and Trz44 (28.1 g, 52.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.9 g, 150.9 mmol) was dissolved in 63 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 1-45. (Yield 72%, MS: [M+H] + =668)

[0489] Synthesis example 1-46

[0490]

[0491] At 0°C, trifluoromethanesulfonic anhydride (119.9 g, 424.9 mmol) and heavy water (42.6 g, 2124.7 mmol) were added and stirred for 5 hours to prepare a solution. 1-Bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, and the temperature was raised to 140°C, and then maintained and stirred. After reacting for 24 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.9 g of substance 1-5-1. (yield 39%, MS: [M+H] + =252)

[0492] Material 1-5-1 (15 g, 59.5 mmol) and bis(pinacolato)diboron (16.6 g, 65.4 mmol) were mixed in 300 mL of 1,4-dihydro- Reflux and stir in oxane. Then, add potassium acetate (8.8 g, 89.2 mmol), stir well, and then add bis(dibenzylideneacetone)palladium (0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol). React for 4 hours, cool to room temperature, separate the organic layer using chloroform and water, and distill the organic layer. Dissolve it again in chloroform, wash it with water twice, separate the organic layer, add anhydrous magnesium sulfate, filter after stirring, and distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.2 g of substance 1-5-2. (Yield 63%, MS: [M+H] + =300)

[0493] Substance 1-5-2 (15 g, 50.1 mmol) and Trz45 (23.4 g, 52.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.8 g, 150.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.1 g of compound 1-46. (Yield 69%, MS: [M+H] + =581)

[0494] Synthesis example 1-47

[0495]

[0496] Substance 1-5-2 (15 g, 50.1 mmol) and Trz46 (23.6 g, 52.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.8 g, 150.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.2 g of compound 1-47. (Yield 69%, MS: [M+H] + =586)

[0497] Synthesis example 1-48

[0498]

[0499] Substance 1-5-2 (15 g, 50.1 mmol) and Trz47 (23.6 g, 52.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.8 g, 150.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 1-48. (Yield 74%, MS: [M+H] + =586)

[0500] Synthesis example 1-49

[0501]

[0502] Substance 1-5-2 (15 g, 50.1 mmol) and Trz48 (27.6 g, 52.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.8 g, 150.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.5 g of compound 1-49. (Yield 68%, MS: [M+H]+=662)

[0503] Synthesis Example 1-50

[0504]

[0505] At 0°C, trifluoromethanesulfonic anhydride (167.8 g, 594.9 mmol) and heavy water (59.6 g, 2974.6 mmol) were added and stirred for 5 hours to prepare a solution. 1-Bromodibenzo[b, d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of 1-bromodibenzo[b, d]furan and 1,2,4-trichlorobenzene, and the temperature was raised to 140°C, and then maintained and stirred. After reacting for 36 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.1 g of substance 1-6-1. (yield 40%, MS: [M+H] + =254)

[0506] Material 1-6-1 (15 g, 59 mmol) and bis(pinacolato)diboron (16.5 g, 64.9 mmol) were mixed in 300 mL of 1,4-dihydro- Reflux in oxane and stir. Then, potassium acetate (8.7 g, 88.5 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.5 mmol) were added. The reaction was allowed to react for 4 hours, cooled to room temperature, and the organic layer was separated by chloroform and water, and then the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6 g of substance 1-6-2. (Yield 65%, MS: [M+H] + =302)

[0507] Substance 1-6-2 (15 g, 49.8 mmol) and Trz49 (22.3 g, 52.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.6 g, 149.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3 g of compound 1-50. (Yield 72%, MS: [M+H] + =566)

[0508] Synthesis example 1-51

[0509]

[0510] Substance 1-6-2 (15 g, 49.8 mmol) and Trz50 (22.5 g, 52.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.6 g, 149.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.4 g of compound 1-51. (Yield 72%, MS: [M+H] + =569)

[0511] Synthesis example 1-52

[0512]

[0513] Substance 1-6-2 (15 g, 49.8 mmol) and Trz51 (27.9 g, 52.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.6 g, 149.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.7 g of compound 1-52. (Yield 74%, MS: [M+H] + =672)

[0514] Synthesis example 1-53

[0515]

[0516] Substance 1-6-2 (15 g, 49.8 mmol) and Trz52 (24.2 g, 52.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.6 g, 149.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound 1-53. (Yield 75%, MS: [M+H] + =601)

[0517] Synthesis example 1-54

[0518]

[0519] Substance 1-6-2 (15 g, 49.8 mmol) and Trz53 (22.9 g, 52.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (20.6 g, 149.4 mmol) was dissolved in 62 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound 1-54. (Yield 65%, MS: [M+H] + =577)

[0520] Synthesis example 1-55

[0521]

[0522] Trz45 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound 1-55_P1. (Yield 66%, MS: [M+H] + =576)

[0523] After adding compound 1-55_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.1 g of compound 1-55. (Yield 40%, MS: [M+H] + =598)

[0524] Synthesis example 1-56

[0525]

[0526] After adding compound 1-3 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.4 g of compound 1-56. At this time, the deuterium substitution rate was calculated by analyzing the number of deuterium substituted in the compound using MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer) and then calculating the percentage of the number of deuterium substituted to the total number of hydrogen that can exist in the chemical formula. (Yield 43%, MS: [M+H] + =597)

[0527] Synthesis example 1-57

[0528]

[0529] After adding compound 1-10 (10 g, 18.2 mmol), PtO2 (1.2 g, 5.5 mmol), and 91 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.1 g of compound 1-57. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 40%, MS: [M+H] + =570)

[0530] Synthesis example 1-58

[0531]

[0532] After adding compound 1-13 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.5 g of compound 1-58. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 43%, MS: [M+H] + =598)

[0533] Synthesis example 1-59

[0534]

[0535] Trz54 (15 g, 31.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.1 g, 33.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-59_P1. (Yield 74%, MS: [M+H] + =602)

[0536] After adding compound 1-59_P1 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.5 g of compound 1-59. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 43%, MS: [M+H] + =626)

[0537] Synthesis Example 1-60

[0538]

[0539] Trz55 (15 g, 33.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (7.5 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2 g of compound 1-60_P1. (Yield 68%, MS: [M+H] +=576)

[0540] After adding compound 1-60_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.2 g of compound 1-60. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 50%, MS: [M+H] + =595)

[0541] Synthesis example 1-61

[0542]

[0543] After adding compound 1-28 (10 g, 16.2 mmol), PtO2 (1.1 g, 4.9 mmol), and 81 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5 g of compound 1-61. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 48%, MS: [M+H] + =638)

[0544] [Production of the compound represented by Chemical Formula 2]

[0545] Synthesis example 2-1

[0546]

[0547] Under a nitrogen atmosphere, substance 2-1 (15 g, 59.4 mmol), amine 1 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.2 g of compound 2-1. (Yield 51%, MS: [M+H] + =602)

[0548] Synthesis example 2-2

[0549]

[0550] Under a nitrogen atmosphere, substance 2-2 (15 g, 59.4 mmol), amine 2 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.3 g of compound 2-2. (Yield 54%, MS: [M+H] + =602)

[0551] Synthesis example 2-3

[0552]

[0553] Substance 2-3 (15 g, 59.4 mmol) and amine 3 (26.8 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 2-3. (Yield 62%, MS: [M+H] + =602)

[0554] Synthesis example 2-4

[0555]

[0556] Under a nitrogen atmosphere, substance 2-4 (15 g, 59.4 mmol), amine 4 (19.3 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.5 g of compound 2-4. (Yield 53%, MS: [M+H] + =526)

[0557] Synthesis Example 2-5

[0558]

[0559] Under a nitrogen atmosphere, substance 2-4 (15 g, 59.4 mmol), amine 5 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.1 g of compound 2-5. (Yield 62%, MS: [M+H] + =602)

[0560] Synthesis Example 2-6

[0561]

[0562] Under a nitrogen atmosphere, substance 2-4 (15 g, 59.4 mmol), amine 6 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.7 g of compound 2-6. (Yield 58%, MS: [M+H] + =602)

[0563] Synthesis Example 2-7

[0564]

[0565] Substance 2-4 (15 g, 59.4 mmol) and amine 7 (26.8 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.5 g of compound 2-7. (Yield 63%, MS: [M+H] + =602)

[0566] Synthesis example 2-8

[0567]

[0568] Under a nitrogen atmosphere, substance 2-5 (15 g, 59.4 mmol), amine 8 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.2 g of compound 2-8. (Yield 51%, MS: [M+H] + =602)

[0569] Synthesis example 2-9

[0570]

[0571] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 9 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.7 g of compound 2-9. (Yield 58%, MS: [M+H] + =602)

[0572] Synthesis example 2-10

[0573]

[0574] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 1 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.2 g of compound 2-10. (Yield 51%, MS: [M+H] + =602)

[0575] Synthesis example 2-11

[0576]

[0577] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 10 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.6 g of compound 2-11. (Yield 55%, MS: [M+H] + =602)

[0578] Synthesis example 2-12

[0579]

[0580] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 11 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.6 g of compound 2-12. (Yield 55%, MS: [M+H] + =602)

[0581] Synthesis example 2-13

[0582]

[0583] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 12 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.2 g of compound 2-13. (Yield 65%, MS: [M+H] + =602)

[0584] Synthesis example 2-14

[0585]

[0586] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 13 (24.9 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.8 g of compound 2-14. (Yield 68%, MS: [M+H] + =616)

[0587] Synthesis example 2-15

[0588]

[0589] Substance 2-6 (15 g, 59.4 mmol) and amine 14 (31.5 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 31 g of compound 2-15. (Yield 77%, MS: [M+H] + =678)

[0590] Synthesis example 2-16

[0591]

[0592] Substance 2-6 (15 g, 59.4 mmol) and amine 15 (34.6 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 32.4 g of compound 2-16. (Yield 75%, MS: [M+H]+ =728)

[0593] Synthesis example 2-17

[0594]

[0595] Under a nitrogen atmosphere, substance 2-6 (15 g, 59.4 mmol), amine 16 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.8 g of compound 2-17. (Yield 61%, MS: [M+H] + =602)

[0596] Synthesis example 2-18

[0597]

[0598] Under a nitrogen atmosphere, substance 2-7 (15 g, 59.4 mmol), amine 10 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.6 g of compound 2-18. (Yield 66%, MS: [M+H] + =602)

[0599] Synthesis example 2-19

[0600]

[0601] Substance 2-7 (15 g, 59.4 mmol) and amine 17 (31.5 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 31 g of compound 2-19. (Yield 77%, MS: [M+H] + =678)

[0602] Synthesis example 2-20

[0603]

[0604] Under a nitrogen atmosphere, substance 2-7 (15 g, 59.4 mmol), amine 18 (24.9 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23 g of compound 2-20. (Yield 63%, MS: [M+H] + =616)

[0605] Synthesis example 2-21

[0606]

[0607] Substance 2-7 (15 g, 59.4 mmol) and amine 19 (26.8 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 2-21. (Yield 67%, MS: [M+H]+ =602)

[0608] Synthesis example 2-22

[0609]

[0610] Under a nitrogen atmosphere, substance 2-7 (15 g, 59.4 mmol), amine 20 (19.3 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.7 g of compound 2-22. (Yield 60%, MS: [M+H] + =526)

[0611] Synthesis example 2-23

[0612]

[0613] Substance 2-7 (15 g, 59.4 mmol) and amine 21 (31.5 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.1 g of compound 2-23. (Yield 70%, MS: [M+H] + =678)

[0614] Synthesis example 2-24

[0615]

[0616] Under a nitrogen atmosphere, substance 2-7 (15 g, 59.4 mmol), amine 22 (24.9 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.5 g of compound 2-24. (Yield 59%, MS: [M+H] + =616)

[0617] Synthesis example 2-25

[0618]

[0619] Substance 2-7 (15 g, 59.4 mmol) and amine 23 (34.6 g, 62.3 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.8 g of compound 2-25. (Yield 62%, MS: [M+H] + =728)

[0620] Synthesis example 2-26

[0621]

[0622] Under a nitrogen atmosphere, substance 2-8 (15 g, 59.4 mmol), amine 16 (24 g, 62.3 mmol), and sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.2 g of compound 2-26. (Yield 65%, MS: [M+H] + =602)

[0623] Synthesis example 2-27

[0624]

[0625] After adding compound 2-2 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.2 g of compound 2-27. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 51%, MW = 614)

[0626] Synthesis example 2-28

[0627]

[0628] After adding compound 2-7 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.3 g of compound 2-28. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 42%, MW = 615)

[0629] Synthesis example 2-29

[0630]

[0631] After adding compound 2-9 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.7 g of compound 2-29. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 46%, MW = 616)

[0632] Synthesis example 2-30

[0633]

[0634] After adding compound 2-10 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.3 g of compound 2-30. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 52%, MW = 617)

[0635] Synthesis example 2-31

[0636]

[0637] After adding compound 2-11 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.3 g of compound 2-31. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 42%, MW = 619)

[0638] Synthesis example 2-32

[0639]

[0640] After adding compound 2-12 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.6 g of compound 2-32. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 55%, MW = 616)

[0641] Synthesis example 2-33

[0642]

[0643] After adding compound 2-14 (10 g, 16.2 mmol), PtO2 (1.1 g, 4.9 mmol), and 81 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.6 g of compound 2-33. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 55%, MW = 628)

[0644] Synthesis example 2-34

[0645]

[0646] After adding compound 2-17 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 5.6 g of compound 2-34. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 55%, MW = 615)

[0647] Synthesis example 2-35

[0648]

[0649] After adding compound 2-24 (10 g, 16.2 mmol), PtO2 (1.1 g, 4.9 mmol), and 81 mL of D2O to a shaking tube, the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with MgSO4, and the sample was purified by silica gel column chromatography to produce 4.4 g of compound 2-35. At this time, the deuterium substitution rate was calculated by the same method as compound 1-56. (Yield 43%, MW = 629)

[0650] Example 1

[0651] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0652] 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 wt %. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film with a thickness of Next, on the hole transport layer, a layer with a film thickness of The electron blocking layer was formed by vacuum deposition of the following EB-1 compound.

[0653] Next, on the EB-1 vapor-deposited film, the following compound 1-1, compound 2-1, and Dp-7 compound were vacuum-deposited at a weight ratio of 49:49:2 to form Thickness of the red emitting layer.

[0654] On the above-mentioned light-emitting layer, the film thickness is The following HB-1 compound was vacuum-deposited to form a hole blocking layer. Next, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form a hole blocking layer. The electron injection and transport layer is formed with a thickness of

[0655] On the electron injection and transport layer, lithium fluoride (LiF) is sequentially The thickness of the aluminum A thickness of is evaporated to form a cathode.

[0656]

[0657] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains / sec evaporation speed, aluminum maintains The evaporation speed is 2x10 / s. During evaporation, the vacuum degree is maintained at 2x10 -7 ~5ⅹ10-6 A support is provided to produce an organic light-emitting device.

[0658] Example 2 to Example 190

[0659] In the organic light-emitting device of Example 1, an organic light-emitting device was manufactured by the same method as in Example 1, except that the first host and the second host described in Tables 1 to 5 below were used instead of Compound 1-1 and Compound 2-1 for co-evaporation at a ratio of 1:1.

[0660] Comparative Examples 1 to 12

[0661] In the organic light-emitting device of Example 1, the first host and the second host described in the following Table 6 were used instead of the compound 1-1 and the compound 2-1 for co-evaporation at a ratio of 1:1, and the organic light-emitting device was manufactured by the same method as in the above Example 1. At this time, the structures of the comparative compounds B-1 to B-4 used in the comparative examples are shown below.

[0662]

[0663] Experimental Example 1: Device Characteristics Evaluation

[0664] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 190 and Comparative Examples 1 to 12, the voltage, efficiency, and life (15 mA / cm 2 The results are shown in the following Tables 1 to 5. The lifespan T95 was measured based on 7000 nits, and T95 refers to the time required for the initial lifespan to be reduced to 95%.

[0665] [Table 1]

[0666]

[0667] [Table 2]

[0668]

[0669] [Table 3]

[0670]

[0671] [Table 4]

[0672]

[0673] [Table 5]

[0674]

[0675] [Table 6]

[0676]

[0677] As shown in Tables 1 to 6 above, the organic light-emitting device of the embodiment in which the first compound represented by the above Chemical Formula 1 and the second compound represented by the above Chemical Formula 2 are simultaneously used as the main materials of the light-emitting layer, shows excellent driving voltage, luminous efficiency and lifespan characteristics compared with the organic light-emitting device of the comparative example using one of the compounds represented by the above Chemical Formulas 1 and 2 and compounds of other structures.

[0678] In particular, the device according to the embodiment has improved driving voltage, efficiency and life characteristics compared with all the comparative example devices using the compound represented by the above chemical formula 1 as the first host and the comparative compounds B-1 to B-4 as the second host. It is thus confirmed that when the combination of the first compound represented by the above chemical formula 1 and the second compound represented by the above chemical formula 2 is used as a common host, energy transfer to the red dopant is effectively achieved in the red light-emitting layer. It can be judged that this is because the common host combination of the embodiment maintains a more stable balance in the light-emitting layer compared with the common host combination of the comparative example device.

[0679] Therefore, it can be confirmed that when the first compound and the second compound are used as the host material of the organic light-emitting device at the same time, the driving voltage, luminous efficiency and life characteristics of the organic light-emitting device can be improved. In this regard, considering that the luminous efficiency and life characteristics of the organic light-emitting device are usually in a trade-off relationship with each other, it can be seen that the organic light-emitting device using the combination of the compounds of the present invention shows significantly improved device characteristics compared with the device of the comparative example.

Claims

1. An organic light-emitting device, comprising: anode, a cathode disposed opposite to the anode, and A light-emitting layer is disposed between the anode and the cathode, The light emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2, [Chemical formula 1] In the chemical formula 1, L1 to L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, R is hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl, k is an integer from 0 to 7, [Chemical formula 2] In the chemical formula 2, X1 and X2 are each independently O or S, A1 and A2 are each independently a naphthalene ring fused to an adjacent five-membered ring, L'1 to L'3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar' is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, R'1 and R'2 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl, a and b are each independently an integer from 0 to 9.

2. The organic light emitting device 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, L1 to L3, Ar1, Ar2, R and k are the same as defined in claim 1.

3. The organic light emitting device according to claim 1, wherein: L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-12 Arylene.

4. The organic light emitting device according to claim 1, wherein: L3 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

5. The organic light emitting device according to claim 1, wherein: Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, or phenanthryl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, Wherein, Ar1 and Ar2 are unsubstituted or substituted by one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, and -Si(phenyl substituted or unsubstituted by deuterium)3.

6. The organic light emitting device according to claim 1, wherein: k is 0; or k is 1 or more, and R is deuterium.

7. The organic light emitting device according to claim 1, wherein: The first compound is any one selected from the following compounds:

8. The organic light emitting device according to claim 1, wherein: The second compound is represented by the following chemical formula 2-1: [Chemical formula 2-1] In the chemical formula 2-1, A'1 is a benzene ring fused with an adjacent five-membered ring and a benzene ring, X1, X2, A2, L'1 to L'3, Ar', R'1, R'2, a and b are the same as defined in claim 1.

9. The organic light emitting device according to claim 1, wherein: X1 and X2 are both O; or X1 and X2 are both S; or X1 is O, X2 is S; or X1 is S and X2 is O.

10. The organic light emitting device according to claim 1, wherein: is any one of the substituents represented by the following chemical formulas 2a to 21: In the chemical formulae 2a to 21, X1, R'1 and a are the same as defined in claim 1.

11. The organic light emitting device according to claim 1, wherein: is any one of the substituents represented by the following chemical formulas 3a to 31: In the chemical formulae 3a to 31, X2, R'2 and b are the same as defined in claim 1.

12. The organic light emitting device according to claim 1, wherein: L'1 and L'2 are each independently a single bond, or a substituted or unsubstituted C 6-12 Arylene.

13. The organic light emitting device according to claim 1, wherein: L'3 is a single bond or a substituted or unsubstituted phenylene group.

14. The organic light emitting device according to claim 1, wherein: Ar' is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, Here, Ar' is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

15. The organic light emitting device according to claim 1, wherein: R'1 and R'2 are both hydrogen; or both deuterium.

16. The organic light emitting device according to claim 1, wherein: The second compound is represented by any one of the following chemical formulas 2-1 to 2-9: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6] [Chemical formula 2-7] [Chemical formula 2-8] [Chemical formula 2-9] In the chemical formulas 2-1 to 2-9, X1, X2, L'1 to L'3, Ar', R'1, R'2, a and b are the same as defined in claim 1.

17. The organic light emitting device according to claim 1, wherein: The second compound is any one selected from the following compounds: In the compound, Dn represents that n hydrogen atoms are replaced by deuterium, wherein n is an integer greater than or equal to 1.

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