Organic light emitting device

Abstract

An organic light emitting device is provided.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2023-0085762 filed on July 3, 2023, and incorporates all disclosures of the Korean Patent Application No. 10-2023-0085762 into this specification.

[0003] The present invention relates to organic light emitting devices. Background Art

[0004] Organic light emitting diodes (OLEDs) are currently under extensive research due to their wide viewing angles, excellent contrast, and fast response times, as well as their superior brightness, drive voltage, and response speed.

[0005] An organic light-emitting device typically has a structure comprising an anode, a cathode, and an organic layer positioned between the anode and cathode. To improve the efficiency and stability of an organic light-emitting device, the organic layer is often formed from multiple layers composed of different materials. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device structure, when 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. When these excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used in the organic light-emitting devices described above, there is a continuous demand for the development of new materials.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] The present invention relates to organic light emitting devices.

[0012] Solution to the problem

[0013] The present invention provides the following organic light-emitting device, comprising:

[0014] anode,

[0015] a cathode disposed opposite to the anode, and

[0016] A light-emitting layer is provided between the anode and the cathode,

[0017] 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:

[0018] [Chemical Formula 1]

[0019]

[0020] In the above Chemical Formula 1,

[0021] L1 to L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene groups,

[0022] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl,

[0023] R is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl, but at least one of R is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl,

[0024] h is 0, 1, or 2,

[0025] k is an integer from 1 to 7,

[0026] [Chemical Formula 2]

[0027]

[0028] In the above chemical formula 2,

[0029] X is O or S,

[0030] L'1 to L'3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene groups,

[0031] Ar' is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl,

[0032] R'1 and R'2 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl,

[0033] a and b are each independently an integer from 0 to 9.

[0034] Effects of the Invention

[0035] The organic light-emitting device comprises two host compounds in the light-emitting layer, thereby improving the efficiency, driving voltage and / or lifespan characteristics of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 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 is shown.

[0037] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, 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. DETAILED DESCRIPTION

[0038] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0039] (Definition of terms)

[0040] In this manual, and "D" represents a bond to other substituents, and "D" represents deuterium.

[0041] 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 1-10Alkyl, C 1-10 Alkoxy and C 6-20 The term "substituted with one or more substituents in an aryl group" or "unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, methyl, ethyl, phenyl, biphenyl and naphthyl" may be used to mean "substituted with one to a maximum number of substitutable hydrogens". Alternatively, the term "substituted with one or more substituents" may be used to mean "substituted with one to five substituents" or "substituted with one or two substituents".

[0042] 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 substituents may be of the following structures, but are not limited thereto.

[0043]

[0044] In the present specification, 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 those of the following structural formulas, but are not limited thereto.

[0045]

[0046] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0047]

[0048] In this specification, silyl refers to -Si(Z1)(Z2)(Z3), where 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 Halogenated alkenyl, 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 6-20Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0049] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0050] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0051] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 5. 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, etc., but are not limited thereto.

[0052] 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 alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0053] 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 number of carbon atoms in the alicyclic group is 3 to 60. According to another embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 20. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spirohydrocarbon groups, and substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds.

[0054] Specifically, examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0055] 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.

[0056] Examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited thereto.

[0057] In addition, the substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds are substituents derived from compounds formed 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.

[0058] In this 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, and 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-mentioned aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned aryl group is 6 to 20. Regarding the above-mentioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the above-mentioned polycyclic aryl group, it can be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0059] In this 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.

[0060] 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 non-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 and substituents derived from hydrogenated derivatives of heteroaromatic compounds.

[0061] 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, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline, isothiophene Examples include, but are not limited to, oxazolyl, thiadiazolyl, and phenothiazinyl.

[0062] The substituents derived from hydrogenated derivatives of heteroaromatic compounds are substituents derived from compounds obtained by hydrogenating some unsaturated bonds of monocyclic or polycyclic heteroaromatic compounds. 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.

[0063] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl groups is the same as the examples of aryl groups described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the examples of alkyl groups described above. In this specification, the heteroaryl group in heteroarylamine is the same as the examples of heteroaryl groups described above. In this specification, the alkenyl group in aralkenyl is the same as the examples of alkenyl groups described above. In this specification, the description of aryl groups described above is applicable except that an arylene group is a divalent group. In this specification, the description of heteroarylene groups described above is applicable except that a heteroarylene group is a divalent group. In this specification, the description of heteroaryl groups described above is applicable except that a hydrocarbon ring is not a monovalent group but is formed by bonding two substituents. In this specification, the description of aryl or cycloalkyl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents. In this specification, the description of heteroaryl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents.

[0064] 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.

[0065] Furthermore, "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with deuterium in which one to a maximum of a maximum of substitutable hydrogen atoms are substituted with deuterium." For example, the term "unsubstituted or substituted with deuterium phenanthrenyl" can be understood to mean "unsubstituted or substituted with one to nine deuterium phenanthrenyl," given that the maximum number of hydrogen atoms that can be substituted with deuterium in the phenanthrenyl structure is nine.

[0066] Furthermore, the term "deuterated structure" refers to compounds, divalent linking groups, or monovalent substituents comprising any structure in which at least one hydrogen atom is replaced by deuterium. For example, the deuterated structure of a phenyl group shown below can be understood to refer to any monovalent substituent in which at least one substitutable hydrogen atom within the phenyl group is replaced by deuterium.

[0067]

[0068] Furthermore, the "deuterium substitution rate" or "degree of deuteration" of a compound is the ratio of the number of deuterium substituted in the compound to the total number of hydrogen atoms that can be present (the sum of the number of hydrogen atoms that can be substituted with deuterium in the compound and the number of substituted deuterium atoms), calculated as a percentage. Therefore, the "deuterium substitution rate" or "degree of deuteration" of a compound as "K%" means that K% of the hydrogen atoms that can be substituted with deuterium in the compound are substituted with deuterium.

[0069] At this time, 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 Deuterium substitution can be measured by conventionally known methods such as H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry). More specifically, when using MALDI-TOF MS, the "deuterium substitution rate" or "degree of deuteration" can be determined by MALDI-TOF MS analysis to determine the number of deuterium substitutions in the compound, and then calculating the ratio of the number of deuterium substitutions in the compound to the total number of hydrogen atoms that may be present as a percentage.

[0070] An organic light-emitting device is provided, comprising: an anode, a cathode disposed opposite the anode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0071] The organic light-emitting device according to the present invention comprises two compounds having specific structures as host substances in the light-emitting layer, which can improve the efficiency, driving voltage and / or life characteristics of the organic light-emitting device.

[0072] Hereinafter, the present invention will be described in detail according to each configuration.

[0073] anode and cathode

[0074] The anode material is preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0075] The cathode material is preferably one with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0076] hole injection layer

[0077] The organic light-emitting device according to the present invention may include a hole injection layer between the anode and a hole transport layer described later, as needed.

[0078] The hole injection layer is located on the anode and is a layer that injects holes from the anode, and contains a hole injection material. Such a hole injection material 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 on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and has excellent thin film forming ability. In particular, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.

[0079] Specific examples of the hole-injecting 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 thereto.

[0080] hole transport layer

[0081] 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. A substance with a high hole mobility is suitable. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers with both conjugated and non-conjugated parts, but the present invention is not limited to these.

[0082] electron blocking layer

[0083] The organic light-emitting device according to the present invention may, if desired, include an electron-blocking layer between the hole-transporting layer and the light-emitting layer. This electron-blocking layer is formed on the hole-transporting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by regulating hole mobility and preventing excessive electron migration, thereby increasing the probability of hole-electron binding. The electron-blocking layer comprises an electron-blocking substance. Examples of such electron-blocking substances include, but are not limited to, arylamine-based organic substances.

[0084] light-emitting layer

[0085] The organic light-emitting device according to the present invention includes a light-emitting layer between an anode and a cathode. The light-emitting layer contains the first and second compounds as host materials. Specifically, the first compound functions as an N-type host material with superior electron-transporting capability compared to hole-transporting capability, while the second compound functions as a P-type host material with superior hole-transporting capability compared to electron-transporting capability. This maintains a suitable hole-to-electron ratio within the light-emitting layer. As a result, excitons emit light uniformly throughout the light-emitting layer, improving both the luminous efficiency and the lifetime of the organic light-emitting device.

[0086] Next, the first compound and the second compound will be described in order.

[0087] (First Compound)

[0088] The first compound is represented by Chemical Formula 1. Specifically, the first compound is a compound in which one triazine group is substituted on dibenzofuran, and has excellent electron transport capability, thereby effectively transferring electrons to the dopant substance, thereby increasing the electron-hole recombination probability in the light-emitting layer.

[0089] On the other hand, in the above Chemical Formula 1, if the binding position of L3 is specifically indicated, it can be represented by the following Chemical Formula 1':

[0090] [Chemical Formula 1']

[0091]

[0092] In the above chemical formula 1',

[0093] 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,

[0094] L1 to L3, Ar1, Ar2, R, h, and k are the same as defined in the above Chemical Formula 1.

[0095] For example, the above Chemical Formula 1 can be represented by the following Chemical Formula 1-1:

[0096] [Chemical Formula 1-1]

[0097]

[0098] In the above chemical formula 1-1,

[0099] L1 to L3, Ar1, Ar2, R, h, and k are the same as defined in the above Chemical Formula 1.

[0100] In one embodiment, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0101] In another embodiment, L1 and L2 are each independently a single bond; or C1 is unsubstituted or substituted with one or more substituents selected from deuterium, phenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium. 6-20 Arylene.

[0102] In another embodiment, L1 and L2 can each independently be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0103] In another embodiment, 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.

[0104] In another embodiment, L1 and L2 are each independently a single bond, a phenylene group, a biphenylene group, or a naphthylene group,

[0105] The above-mentioned phenylene group, biphenyldiyl group and naphthylene group may be unsubstituted or substituted with deuterium.

[0106] For example, L1 and L2 can each independently be a single bond, or any one selected from the following groups and their deuterated structures:

[0107]

[0108] In addition, L1 and L2 may be the same as each other. Alternatively, L1 and L2 may be different.

[0109] For example, L1 and L2 are both single bonds; or

[0110] One of L1 and L2 is 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.

[0111] In addition, in one embodiment, L3 can be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0112] In another embodiment, L3 can be a single bond; or C3 which is unsubstituted or substituted with one or more substituents selected from deuterium, phenyl and naphthyl. 6-20 Arylene.

[0113] In another embodiment, L3 may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0114] For example, L3 may be a single bond or any one of the divalent linking groups represented by the following chemical formulas 4a to 4m:

[0115]

[0116] In the above Chemical Formulas 4a to 4m,

[0117] D stands for deuterium,

[0118] p is an integer from 0 to 6,

[0119] q is an integer from 0 to 4.

[0120] In other words, in the above Chemical Formulas 4a to 4m,

[0121] p is 0, 1, 2, 3, 4, 5, or 6,

[0122] q is 0, 1, 2, 3 or 4.

[0123] Here, h refers to the number of L3. When h is 2, the two L3 can be the same as or different from each other.

[0124] In addition, in one embodiment, Ar1 and Ar2 can be substituted or unsubstituted C 6-20 Aryl.

[0125] In another embodiment, Ar1 and Ar2 can each independently be unsubstituted or selected from deuterium, deuterium-substituted or unsubstituted C 1-10 Alkyl, deuterium-substituted or unsubstituted C 6-20 Aryl, -Si (substituted or unsubstituted C1-10 Alkyl)3, and -Si (substituted or unsubstituted C 6-20 Aryl) 3 substituted with one or more substituents C 6-20 Aryl.

[0126] Specifically, for example, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthofuranyl group or a benzonaphthothiophenyl group,

[0127] 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.

[0128] For example, Ar1 and Ar2 can each independently be any one selected from the following groups and their deuterated structures:

[0129]

[0130]

[0131] In one embodiment, Ar1 and Ar2 may be identical to each other. Alternatively, Ar1 and Ar2 may be different.

[0132] In another embodiment, L1-Ar1 and L2-Ar2 may be identical to each other.

[0133] Alternatively, L1-Ar1 and L2-Ar2 may be different.

[0134] In addition, in one embodiment, R is hydrogen; deuterium; substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing one heteroatom of N, O and S 2-20 Heteroaryl, however, at least one of R may be substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing one heteroatom of N, O and S 2-20 Heteroaryl.

[0135] In another embodiment, R is hydrogen, deuterium, C 6-20 Aryl, or C containing O or S 2-20 Heteroaryl, but at least one of R is C 6-20 Aryl, or C containing O or S 2-20 heteroaryl,

[0136] Among them, the above C 6-20 Aryl and C 2-20The heteroaryl group may be unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

[0137] In another embodiment, at least one of R is any one of an aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any one of a heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, and the rest are hydrogen or deuterium,

[0138] The aryl and heteroaryl groups may be unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, and deuterium-substituted or unsubstituted naphthyl.

[0139] For example, at least one of R is any one selected from the following substituents and deuterated substituents thereof, and the rest may be hydrogen or deuterium:

[0140]

[0141]

[0142] Here, k represents the number of R. When k is 2 or greater, the two or more Rs may be the same or different. Specifically, k is 0, 1, 2, 3, 4, 5, 6, or 7.

[0143] For example, k is 1, R is any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, or

[0144] k is 2 to 7, one of R is any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, and the rest are deuterium,

[0145] The aryl and heteroaryl groups may be unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

[0146] More specifically, when one of R is an aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, and fluoranthenyl; or a heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl, one, two, three, four, five, or six of the remaining R may be deuterium. In other words, k may be 2, 3, 4, 5, 6, or 7.

[0147] In addition, in one embodiment, It may be any one of the substituents represented by the following Chemical Formulas 1a to 1g:

[0148]

[0149] In the above Chemical Formulas 1a to 1g,

[0150] R' is substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing one heteroatom of N, O and S 2-20 heteroaryl,

[0151] d is an integer from 0 to 6.

[0152] For example, d can be 0, 1, 2, 3, 4, 5, or 6.

[0153] For example, R' is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl, or

[0154] Here, R' may be unsubstituted, or substituted with one or more substituents selected from deuterium, halogen, cyano, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, and deuterium-substituted or unsubstituted naphthyl.

[0155] In addition, the first compound may contain no deuterium or may contain one or more deuteriums.

[0156] 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.

[0157] As an example, the first compound may contain no deuterium, or may contain 1 to 50 deuterium atoms. More specifically, the first compound may contain no 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 deuterium atoms.

[0158] In this case, the number of deuterium substitutions in the first compound can be represented by the following chemical formula 1D:

[0159] [Chemical Formula 1D]

[0160]

[0161] In the above Chemical Formula 1D,

[0162] Dn means n hydrogens are replaced by deuterium.

[0163] Wherein, n is an integer greater than 0,

[0164] L 1a To L 3a 、Ar 1a 、Ar 2a and R a Each represents L1 to L3, Ar1, Ar2 and R substituents which are not substituted by deuterium.

[0165] Specifically, in the above Chemical Formula 1D, n may be 1 or greater. More specifically, in the above Chemical Formula 1D, n may be 1 or greater, 2 or greater, 3 or greater, 4 or greater, 5 or greater, 6 or greater, 7 or greater, 8 or greater, 9 or greater, 10 or greater, 11 or greater, 13 or greater, 15 or greater, or 17 or greater and 50 or less, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, or 20 or less.

[0166] On the other hand, representative examples of the first compound are shown below:

[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]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[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]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329] On the other hand, the first compound can be produced by the production method shown in the following reaction formula 1:

[0330] [Reaction formula 1]

[0331]

[0332] In the above reaction formula 1, Y is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0333] 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-coupling reaction can be appropriately changed. The manufacturing method of the first compound can be more specifically described in the manufacturing example described later.

[0334] (Second Compound)

[0335] The second compound is represented by Chemical Formula 2. Specifically, the second compound is a tertiary amine compound having both a phenanthrene substituent and a (benzonaphthofuranyl / benzonaphthothienyl) substituent of a specific structure, characterized in that any carbon atom from carbon atoms 1 to 4 of the phenanthrene substituent is bonded to the nitrogen atom of the amino group, and the benzene ring of the benzonaphthofuranyl / benzonaphthothienyl substituent is bonded to the nitrogen atom of the amino group. The compound represented by Chemical Formula 1 having the above structure can effectively transfer holes to the dopant substance, thereby increasing the recombination probability of holes and electrons within the light-emitting layer together with the first compound having excellent electron transport ability.

[0336] In one embodiment, It may be any one of the substituents represented by the following Chemical Formulas 2a to 2d:

[0337]

[0338] In the above Chemical Formulas 2a to 2d,

[0339] R'1 and a are the same as defined in the above Chemical Formula 1.

[0340] In addition, in one embodiment, It may be any one of the substituents represented by the following Chemical Formulas 3a to 3d:

[0341]

[0342] In the above Chemical Formulas 3a to 3d,

[0343] X, R'2 and b are the same as defined in the above Chemical Formula 1.

[0344] In one embodiment, L'1 and L'2 are each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0345] In another embodiment, L'1 and L'2 are each independently a single bond; or C ' is unsubstituted or substituted with one or more substituents selected from deuterium, phenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium. 6-20 Arylene.

[0346] In another embodiment, L'1 and L'2 can each independently be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0347] In another embodiment, 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.

[0348] 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:

[0349]

[0350] In another embodiment, L'1 can be substituted or unsubstituted C 6-12 Arylene.

[0351] For example, L'1 may be a substituted or unsubstituted phenylene group.

[0352] For example, L'1 may be a substituted or unsubstituted 1,4-phenylene group.

[0353] In another embodiment, L'2 can be a single bond.

[0354] In this case, L'1 and L'2 may be the same as each other or different from each other.

[0355] In another embodiment, L'3 can be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0356] In another embodiment, L'3 can be a single bond, or a C '3 which is unsubstituted or substituted with one or more substituents selected from deuterium, phenyl substituted or unsubstituted with deuterium, and naphthyl substituted or unsubstituted with deuterium. 6-20 Arylene.

[0357] In another embodiment, L'3 can be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0358] In another embodiment, L'3 may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0359] For example, L'3 can be a single bond.

[0360] In another embodiment, Ar' can be substituted or unsubstituted C 6-20 Aryl, or substituted or unsubstituted C containing O or S heteroatom 2-20 Heteroaryl.

[0361] In another embodiment, Ar' is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl,

[0362] Here, Ar' may be substituted or unsubstituted.

[0363] In another embodiment, Ar' is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl,

[0364] Ar' may be unsubstituted, or substituted with one or more substituents selected from deuterium, halogen, cyano, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, and deuterium-substituted or unsubstituted naphthyl.

[0365] For example, Ar' may be any one selected from the following groups and their deuterated structures, but is not limited thereto:

[0366]

[0367]

[0368] Wherein, 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.

[0369] 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.

[0370] For example, R'1 and R'2 may both be hydrogen, or may both be deuterium.

[0371] In addition, the second compound can be represented by the following Chemical Formula 2A or 2B:

[0372] [Chemical Formula 2A]

[0373]

[0374] [Chemical Formula 2B]

[0375]

[0376] In the above Chemical Formulas 2A and 2B,

[0377] R'3 is hydrogen or deuterium,

[0378] c is an integer from 0 to 4,

[0379] X, L'2, L'3, Ar', R'1, R'2, a and b are the same as defined in the above Chemical Formula 2.

[0380] More specifically, the second compound may be represented by any one of the following Chemical Formulas 2-1 to 2-4:

[0381] [Chemical Formula 2-1]

[0382]

[0383] [Chemical Formula 2-2]

[0384]

[0385] [Chemical formula 2-3]

[0386]

[0387] [Chemical formula 2-4]

[0388]

[0389] In the above chemical formulas 2-1 to 2-4,

[0390] X, L'2, L'3, Ar', R'1, R'2, a and b are the same as defined in the above Chemical Formula 2.

[0391] In addition, the second compound may contain no deuterium or may contain one or more deuteriums.

[0392] 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.

[0393] As an example, the second compound may contain no deuterium, or may contain 1 to 50 deuterium atoms. More specifically, the second compound may contain no 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 deuterium atoms.

[0394] In this case, the number of deuterium substitutions in the second compound can be represented by the following chemical formula 2D:

[0395] [Chemical Formula 2D]

[0396]

[0397] In the above Chemical Formula 2D,

[0398] Dn means n hydrogens are replaced by deuterium.

[0399] Wherein, n is an integer greater than 0,

[0400] L' 1a To L' 3a 、Ar' a , R' 1a and R' 2a Each represents L'1 to L'3, Ar', R'1 and R'2 substituents which are not substituted by deuterium.

[0401] Specifically, in the above Chemical Formula 2D, n may be 1 or greater. More specifically, in the above Chemical Formula 2D, n may be 1 or greater, 2 or greater, 3 or greater, 4 or greater, 5 or greater, 6 or greater, 7 or greater, 8 or greater, 9 or greater, 10 or greater, 11 or greater, 13 or greater, 15 or greater, or 17 or greater and 50 or less, 40 or less, 30 or less, 28 or less, 26 or less, or 24 or less.

[0402] On the other hand, representative examples of the second compound are shown below:

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431] Among the above compounds,

[0432] Dn means n hydrogens are replaced by deuterium.

[0433] Here, n is an integer greater than or equal to 1.

[0434] On the other hand, as an example, the second compound can be produced by the production method shown in the following reaction formula 2:

[0435] [Reaction formula 2]

[0436]

[0437] 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.

[0438] 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 in the amine substitution reaction can be appropriately modified. The method for producing the second compound can be further specified in the production examples described below.

[0439] 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, 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 to appropriately maintain the hole-to-electron ratio in the light-emitting layer. Preferably, the first compound and the second compound are contained in the light-emitting layer at a weight ratio of 50:50.

[0440] On the other hand, the light-emitting layer may contain a dopant substance in addition to the two host substances. Such dopant substances include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0441] More specifically, the dopant material may include, but is not limited to, the following compounds:

[0442]

[0443]

[0444]

[0445]

[0446] hole blocking layer

[0447] 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 is 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 the 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 hole blocking substances, azine derivatives containing triazine, triazole derivatives, Compounds into which electron-withdrawing groups are introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0448] Electron injection and transport layer

[0449] 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 an electron transport layer and an 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, as well as their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives, are used together, but are not limited thereto.

[0450] The electron injection and transport layer can 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 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, fluorenylmethane, anthrone, etc. and their derivatives, metal coordination compounds and nitrogen-containing five-membered ring derivatives, etc.

[0451] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-hydroxyquinolinato)gallium chloride, bis(2-methyl-8-hydroxyquinolinato)(o-cresol)gallium, bis(2-methyl-8-hydroxyquinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-hydroxyquinolinato)(2-naphthol)gallium.

[0452] organic light-emitting devices

[0453] The structure of the organic light emitting device according to the present invention is shown in FIG. Figure 1 . 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.

[0454] Figure 2 The figure shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the above structure, the first compound and the second compound can be contained in the light-emitting layer.

[0455] The organic light-emitting device according to the present invention can be manufactured by sequentially stacking the above-mentioned structures. In this case, it can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is vapor-deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then the above-mentioned layers are formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. In addition, a main body and a dopant can be formed into a light-emitting layer not only by vacuum evaporation, but also by solution coating. 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 these.

[0456] 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.

[0457] 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. In particular, it may be a bottom emission device requiring relatively high luminous efficiency.

[0458] The preparation of the compound represented by the above Chemical Formula 1, the compound represented by the above Chemical Formula 2, and an organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are provided to illustrate the present invention and the scope of the present invention is not limited thereto.

[0459] [Manufacturing of the First Compound Represented by Chemical Formula 1]

[0460] Synthesis example 1-1

[0461]

[0462] (2-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz1 (26.7 g, 63.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then added to the mixture after being dissolved in 76 mL of water and stirred thoroughly. Bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was then added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.5 g of compound 1-1_P1. (Yield 69%, MS: [M+H] + =584)

[0463] Compound 1-1_P1 (15 g, 25.7 mmol) and naphthalen-2-ylboronic acid (4.6 g, 27 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.6 g, 77 mmol) was then dissolved in 32 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 12.1 g of compound 1-1. (Yield 70%, MS: [M+H] + =676)

[0464] Synthesis example 1-2

[0465]

[0466] (2-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz2 (30.9 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 26.5 g of compound 1-2_P1. (Yield 67%, MS: [M+H] + =650)

[0467] Compound 1-2_P1 (15 g, 23.1 mmol) and dibenzo[b, d]furan-2-ylboronic acid (5.1 g, 24.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.6 g, 69.2 mmol) was then dissolved in 29 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 2 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 1-2. (Yield 73%, MS: [M+H] + =782)

[0468] Synthesis Example 1-3

[0469]

[0470] (2-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz3 (27.1 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 23.3 g of compound 1-3_P1. (Yield 66%, MS: [M+H] + =580)

[0471] Compound 1-3_P1 (15 g, 25.4 mmol) and [1,1'-biphenyl]-4-ylboronic acid (5.3 g, 26.7 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.5 g, 76.3 mmol) was then dissolved in 32 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 13.5 g of compound 1-3. (Yield 75%, MS: [M+H] + =708)

[0472] Synthesis Example 1-4

[0473]

[0474] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz4 (28.4 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 mL of water and added, and 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, 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 27.4 g of compound 1-4_P1. (Yield 74%, MS: [M+H] + =610)

[0475] Compound 1-4_P1 (15 g, 24.6 mmol) and naphthalene-2-ylboronic acid (4.4 g, 25.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.2 g, 73.8 mmol) was then 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 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 11.2 g of compound 1-4. (Yield 65%, MS: [M+H] + =702)

[0476] Synthesis Example 1-5

[0477]

[0478] (3-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz5 (17.1 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 18.7 g of compound 1-5_P1. (Yield 71%, MS: [M+H] + =434)

[0479] Compound 1-5_P1 (15 g, 34.6 mmol) and fluoranthen-3-ylboronic acid (fluoranthen-3-ylboronic acid) (8.9 g, 36.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.3 g, 103.7 mmol) was then 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 14.9 g of compound 1-5. (Yield 72%, MS: [M+H] + =600)

[0480] Synthesis Example 1-6

[0481]

[0482] Compound 1-5_P1 (15 g, 34.6 mmol) and naphtho[2,3-b]benzofuran-1-ylboronic acid (9.5 g, 36.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.3 g, 103.7 mmol) was then 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 13.8 g of compound 1-6. (Yield 65%, MS: [M+H] + =616)

[0483] Synthesis Example 1-7

[0484]

[0485] (3-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz6 (32.9 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 27.4 g of compound 1-7_P1. (Yield 71%, MS: [M+H] + =636)

[0486] Compound 1-7_P1 (15 g, 23.6 mmol) and naphthalene-2-ylboronic acid (4.3 g, 24.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.8 g, 70.7 mmol) was then dissolved in 29 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 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 11.5 g of compound 1-7. (Yield 67%, MS: [M+H] + =728)

[0487] Synthesis Example 1-8

[0488]

[0489] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium oxide (10.7 g, 532.8 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium oxide was then slowly added dropwise to the mixed solution of 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then 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 6.5 g of substance (sub) 1-1-1. (Yield 43%, MS: [M+H] + =283)

[0490] Substance 1-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were mixed in 300 mL of 1,4-diborane. The mixture was refluxed and stirred in 1,4-dioxane. Then, potassium acetate (7.8 g, 79.4 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.8 g of substance 1-1-2. (Yield 62%, MS: [M+H] + =331)

[0491] Substance 1-1-2 (15 g, 45.4 mmol) and Trz7 (28.1 g, 47.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 136.1 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 2 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 23.3 g of compound 1-8_P1. (Yield 72%, MS: [M+H] + =714)

[0492] Compound 1-8_P1 (15 g, 21 mmol) and phenylboronic acid (2.7 g, 22.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (8.7 g, 63 mmol) was then dissolved in 26 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 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 10 g of compound 1-8. (Yield 63%, MS: [M+H] + =756)

[0493] Synthesis Example 1-9

[0494]

[0495] Substance 1-1-2 (15 g, 45.4 mmol) and Trz8 (29.6 g, 47.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 136.1 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 25.3 g of compound 1-9_P1. (Yield 75%, MS: [M+H] + =744)

[0496] Compound 1-9_P1 (15 g, 20.2 mmol) and phenylboronic acid (2.6 g, 21.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (8.4 g, 60.5 mmol) was then dissolved in 25 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 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, 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 11.1 g of compound 1-9. (Yield 70%, MS: [M+H] + =786)

[0497] Synthesis Example 1-10

[0498]

[0499] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium hydroxide (21.4 g, 1065.6 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-Bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was then slowly added dropwise to the mixed solution of 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.3 g of substance 1-2-1. (Yield 35%, MS: [M+H] + =285)

[0500] Material 1-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were mixed in 300 mL of 1,4-diboron The mixture was refluxed in oxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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 11 g of substance 1-2-2. (Yield 63%, MS: [M+H] + =333)

[0501] Substance 1-2-2 (15 g, 45.1 mmol) and Trz9 (15.8 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 14.6 g of compound 1-10_P1. (Yield 66%, MS: [M+H] + =493)

[0502] Compound 1-10_P1 (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. Potassium carbonate (12.6 g, 91.3 mmol) was then 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 2 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 1-10. (Yield 70%, MS: [M+H] + =625)

[0503] Synthesis Example 1-11

[0504]

[0505] (3-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz10 (25.2 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 21.1 g of compound 1-11_P1. (Yield 62%, MS: [M+H] + =560)

[0506] Compound 1-11_P1 (15 g, 26.8 mmol) and phenylboronic acid (3.4 g, 28.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 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 2 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 11.8 g of compound 1-11_P2. (Yield 73%, MS: [M+H] + =602)

[0507] In a shake tube, compound 1-11_P2 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O were added. The tube was sealed and heated at 250°C and 600 psi for 12 hours. At the end of the reaction, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 3.1 g of compound 1-11. (Yield 30%, MS: [M+H]) + =626)

[0508] Synthesis Example 1-12

[0509]

[0510] (3-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz11 (23.5 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 1-12_P1. (Yield 72%, MS: [M+H] + =534)

[0511] Compound 1-12_P1 (15 g, 28.1 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (6.7 g, 29.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.6 g, 84.3 mmol) was then 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 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, 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 12.4 g of compound 1-12_P2. (Yield 65%, MS: [M+H] + =682)

[0512] Compound 1-12_P2 (10 g, 14.7 mmol), PtO2 (1 g, 4.4 mmol), and 73 mL of D2O were added to a shaker tube. The tube was sealed and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 5.1 g of compound 1-12. (Yield 49%, MS: [M+H]) + =706)

[0513] Synthesis Example 1-13

[0514]

[0515] (4-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz12 (30 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 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, 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 24.4 g of compound 1-13_P1. (Yield 63%, MS: [M+H] + =636)

[0516] Compound 1-13_P1 (15 g, 23.6 mmol) and naphthalene-2-ylboronic acid (4.3 g, 24.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.8 g, 70.7 mmol) was then dissolved in 29 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 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 10.5 g of compound 1-13. (Yield 61%, MS: [M+H] + =728)

[0517] Synthesis Example 1-14

[0518]

[0519] (4-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz13 (22 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 22.3 g of compound 1-14_P1. (Yield 72%, MS: [M+H] + =510)

[0520] Compound 1-14_P1 (15 g, 29.4 mmol) and naphtho[2,3-b]benzofuran-4-ylboronic acid (8.1 g, 30.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.2 g, 88.2 mmol) was then 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 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 14.2 g of compound 1-14. (Yield 70%, MS: [M+H] + =692)

[0521] Synthesis Example 1-15

[0522]

[0523] (4-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz14 (26.1 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 24.8 g of compound 1-15_P1. (Yield 71%, MS: [M+H] + =574)

[0524] Compound 1-15_P1 (15 g, 26.1 mmol) and dibenzo[b,d]furan-1-ylboronic acid (5.8 g, 27.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.8 g, 78.4 mmol) was then dissolved in 33 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 11.1 g of compound 1-15. (Yield 60%, MS: [M+H] + =706)

[0525] Synthesis Example 1-16

[0526]

[0527] Trifluoromethanesulfonic anhydride (45.1 g, 159.8 mmol) and deuterium hydroxide (16 g, 799.2 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-Bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was then slowly added dropwise to the mixed solution of 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The temperature was raised to 140°C and maintained while stirring. After reacting for 7 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.6 g of substance 1-3-1. (Yield 37%, MS: [M+H] + =284)

[0528] Material 1-3-1 (15 g, 52.7 mmol) and bis(pinacolato)diboron (14.7 g, 58 mmol) were mixed in 300 mL of 1,4-diboron. The mixture was refluxed in oxane and stirred. Then, potassium acetate (7.8 g, 79.1 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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 10.1 g of substance 1-3-2. (Yield 58%, MS: [M+H] + =332)

[0529] Substance 1-3-2 (15 g, 45.2 mmol) and Trz15 (17.7 g, 47.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 135.7 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 2 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 15.4 g of compound 1-16_P1. (Yield 63%, MS: [M+H] + =542)

[0530] Compound 1-16_P1 (15 g, 27.7 mmol) and (phenyl-d5) boronic acid ((phenyl-d5) boronic acid) (3.7 g, 29.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.5 g, 83 mmol) was then 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 11.9 g of compound 1-16. (Yield 73%, MS: [M+H] + =589)

[0531] Synthesis Example 1-17

[0532]

[0533] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz16 (23.5 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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, 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 23.4 g of compound 1-17_P1. (Yield 72%, MS: [M+H] + =534)

[0534] Compound 1-17_P1 (15 g, 28.1 mmol) and naphthalene-2-ylboronic acid (5.1 g, 29.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.6 g, 84.3 mmol) was then 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 12.5 g of compound 1-17. (Yield 71%, MS: [M+H] + =626)

[0535] Synthesis Example 1-18

[0536]

[0537] (6-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz17 (29.7 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 24.6 g of compound 1-18_P1. (Yield 69%, MS: [M+H] + =586)

[0538] Compound 1-18_P1 (15 g, 25.6 mmol) and naphthalene-2-ylboronic acid (4.6 g, 26.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.6 g, 76.8 mmol) was then dissolved in 32 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 2 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 10.9 g of compound 1-18. (Yield 63%, MS: [M+H] + =678)

[0539] Synthesis Example 1-19

[0540]

[0541] (6-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz18 (31.2 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 24.5 g of compound 1-19_P1. (Yield 66%, MS: [M+H] +=610)

[0542] Compound 1-19_P1 (15 g, 24.6 mmol) and naphthalene-2-ylboronic acid (4.4 g, 25.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.2 g, 73.8 mmol) was then 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 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-19. (Yield 66%, MS: [M+H] + =702)

[0543] Synthesis Example 1-20

[0544]

[0545] (6-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz19 (20.3 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 19.1 g of compound 1-20_P1. (Yield 65%, MS: [M+H] + =484)

[0546] Compound 1-20_P1 (15 g, 31 mmol) and phenanthren-9-ylboronic acid (7.2 g, 32.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then 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 2 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 g of compound 1-20. (Yield 62%, MS: [M+H] + =626)

[0547] Synthesis example 1-21

[0548]

[0549] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium hydroxide (10.7 g, 532.8 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-bromo-6-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was slowly added dropwise to the mixed solution of 1-bromo-6-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, and then filtered. The filtrate was evaporated under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.8 g of substance 2-1-1. (Yield 45%, MS: [M+H] + =283)

[0550] Substance 2-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were mixed in 300 mL of 1,4-diboron The mixture was refluxed in oxane and stirred. Then, potassium acetate (7.8 g, 79.4 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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 13.1 g of substance 2-1-2. (Yield 75%, MS: [M+H] + =331)

[0551] Substance 2-1-2 (15 g, 45.4 mmol) and Trz20 (22.6 g, 47.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 136.1 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 17.8 g of compound 1-21_P1. (Yield 61%, MS: [M+H] + =643)

[0552] Compound 1-21_P1 (15 g, 23.3 mmol) and (phenyl-d5) boronic acid (3.1 g, 24.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.7 g, 70 mmol) was then dissolved in 29 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 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, 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 11.9 g of compound 1-21. (Yield 74%, MS: [M+H] + =690)

[0553] Synthesis example 1-22

[0554]

[0555] Substance 2-1-2 (15 g, 45.4 mmol) and Trz21 (21.1 g, 47.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 136.1 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 18.6 g of compound 1-22_P1. (Yield 67%, MS: [M+H] + =612)

[0556] Compound 1-22_P1 (15 g, 24.5 mmol) and (phenyl-d5) boronic acid (3.3 g, 25.7 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.2 g, 73.5 mmol) was then dissolved in 30 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 2 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 10 g of compound 1-22. (Yield 62%, MS: [M+H] + =659)

[0557] Synthesis example 1-23

[0558]

[0559] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium hydroxide (21.4 g, 1065.6 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-Bromo-6-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was then slowly added dropwise to the mixed solution of 1-bromo-6-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The temperature was raised to 140°C and maintained while stirring. After reacting for 10 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.5 g of substance 2-2-1. (Yield 43%, MS: [M+H] + =285)

[0560] Material 2-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were mixed in 300 mL of 1,4-diboron The mixture was refluxed in alkane and stirred. Then, potassium acetate (7.7 g, 78.8 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted for 5 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 13.1 g of substance 2-2-2. (Yield 75%, MS: [M+H] + =333)

[0561] Substance 2-2-2 (15 g, 60.9 mmol) and Trz22 (36.1 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 28.9 g of compound 1-23_P1. (Yield 69%, MS: [M+H] + =690)

[0562] Compound 1-23_P1 (15 g, 21.7 mmol) and phenylboronic acid (2.8 g, 22.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9 g, 65.2 mmol) was then dissolved in 27 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 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 9.5 g of compound 1-23. (Yield 60%, MS: [M+H] + =732)

[0563] Synthesis Example 1-24

[0564]

[0565] In a shaker tube, compound 1-8 (10 g, 14.8 mmol), PtO2 (1 g, 4.4 mmol), and 74 mL of D2O were added, the tube was sealed, and heated at 250°C and 600 psi for 12 hours. At the end of the reaction, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified by silica gel column chromatography to produce 5.1 g of compound 1-24. (Yield 49%, MS: [M+H] + =706)

[0566] Synthesis Example 1-25

[0567]

[0568] (3-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz23 (25.2 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 20.7 g of compound 1-25_P1. (Yield 63%, MS: [M+H] + =540)

[0569] Compound 1-25_P1 (15 g, 27.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.2 g, 29.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.5 g, 83.3 mmol) was then 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 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, 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 11.4 g of compound 1-25_P2. (Yield 61%, MS: [M+H] + =672)

[0570] In a shaker tube, compound 1-25_P2 (10 g, 14.9 mmol), PtO2 (1 g, 4.5 mmol), and 74 mL of D2O were added. The tube was sealed and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 3.7 g of compound 1-25. (Yield 36%, MS: [M+H]) + =695)

[0571] Synthesis example 1-26

[0572]

[0573] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz19 (20.3 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 17.6 g of compound 1-26_P1. (Yield 60%, MS: [M+H] + =484)

[0574] Compound 1-26_P1 (15 g, 31 mmol) and naphthalene-2-ylboronic acid (5.6 g, 32.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then 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 2 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 1-26. (Yield 73%, MS: [M+H] + =576)

[0575] Synthesis example 1-27

[0576]

[0577] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz24 (22.9 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 20.4 g of compound 1-27_P1. (Yield 64%, MS: [M+H] + =524)

[0578] Compound 1-27_P1 (15 g, 28.6 mmol) and naphthalene-2-ylboronic acid (5.2 g, 30.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.9 g, 85.9 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. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 1-27. (Yield 62%, MS: [M+H] + =616)

[0579] Synthesis example 1-28

[0580]

[0581] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz25 (22.9 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 22.6 g of compound 1-28_P1. (Yield 71%, MS: [M+H] + =524)

[0582] Compound 1-28_P1 (15 g, 28.6 mmol) and phenanthren-3-ylboronic acid (6.7 g, 30.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.9 g, 85.9 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. 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 1-28. (Yield 68%, MS: [M+H] + =666)

[0583] Synthesis example 1-29

[0584]

[0585] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz26 (25.2 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 21.1 g of compound 1-29_P1. (Yield 62%, MS: [M+H] + =560)

[0586] Compound 1-29_P1 (15 g, 26.8 mmol) and dibenzo[b,d]thiophene-4-ylboronic acid (6.4 g, 28.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 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, 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 12.3 g of compound 1-29. (Yield 65%, MS: [M+H] + =708)

[0587] Synthesis Example 1-30

[0588]

[0589] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz27 (38.6 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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 29.1 g of compound 1-30_P1. (Yield 66%, MS: [M+H]+ =726)

[0590] Compound 1-30_P1 (15 g, 20.7 mmol) and naphthalene-2-ylboronic acid (3.7 g, 21.7 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (8.6 g, 62 mmol) was then dissolved in 26 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, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.6 g of compound 1-30. (Yield 63%, MS: [M+H] + =818)

[0591] Synthesis example 1-31

[0592]

[0593] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium hydroxide (10.7 g, 532.8 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-bromo-7-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was then slowly added dropwise to the mixed solution of 1-bromo-7-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, and then filtered. The filtrate was evaporated under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6 g of substance 3-1-1. (Yield 40%, MS: [M+H] + =283)

[0594] Material 3-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were mixed in 300 mL of 1,4-diboron. The mixture was refluxed in oxane and stirred. Potassium acetate (7.8 g, 79.4 mmol) was then added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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 11.4 g of substance 3-1-2. (Yield 65%, MS: [M+H] + =331)

[0595] Substance 3-1-2 (15 g, 45.4 mmol) and Trz28 (28.6 g, 47.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.8 g, 136.1 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 2 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 1-31_P1. (Yield 62%, MS: [M+H] + =723)

[0596] Compound 1-31_P1 (15 g, 20.7 mmol) and phenanthren-3-ylboronic acid (4.8 g, 21.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (8.6 g, 62.2 mmol) was then dissolved in 26 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 2 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 11.5 g of compound 1-31. (Yield 64%, MS: [M+H] + =866)

[0597] Synthesis example 1-32

[0598]

[0599] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium hydroxide (21.4 g, 1065.6 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-Bromo-7-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was then slowly added dropwise to the mixed solution of 1-bromo-7-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.7 g of substance 3-2-1. (Yield 44%, MS: [M+H] + =285)

[0600] Material 3-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were mixed in 300 mL of 1,4-diboron. The mixture was refluxed in alkane and stirred. Then, potassium acetate (7.7 g, 78.8 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was reacted 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 11.7 g of substance 3-2-2. (Yield 67%, MS: [M+H] + =333)

[0601] Substance 3-2-2 (15 g, 45.1 mmol) and Trz29 (18.7 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 2 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 g of compound 1-32_P1. (Yield 71%, MS: [M+H] + =564)

[0602] Compound 1-32_P1 (15 g, 26.6 mmol) and (phenyl-d5) boronic acid (3.5 g, 27.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11 g, 79.8 mmol) was then dissolved in 33 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 11.4 g of compound 1-32. (Yield 70%, MS: [M+H] + =611)

[0603] Synthesis example 1-33

[0604]

[0605] Substance 3-2-2 (15 g, 45.1 mmol) and Trz30 (24.8 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 2 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 18.4 g of compound 1-33_P1. (Yield 63%, MS: [M+H] + =650)

[0606] Compound 1-33_P1 (15 g, 23.1 mmol) and phenylboronic acid (3 g, 24.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.6 g, 69.2 mmol) was then dissolved in 29 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 2 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 11.5 g of compound 1-33. (Yield 72%, MS: [M+H] + =692)

[0607] Synthesis example 1-34

[0608]

[0609] Compound 1-26 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O were added to a shaker tube, the tube was sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified by silica gel column chromatography to produce 3.9 g of compound 1-34. (Yield 38%, MS: [M+H]) + =598)

[0610] Synthesis example 1-35

[0611]

[0612] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz29 (25.2 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 23.8 g of compound 1-35_P1. (Yield 70%, MS: [M+H] + =560)

[0613] Compound 1-35_P1 (15 g, 26.8 mmol) and phenylboronic acid (3.4 g, 28.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 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 11.3 g of compound 1-35_P2. (Yield 70%, MS: [M+H] + =602)

[0614] Compound 1-35_P2 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 mL of D2O were added to a shaker tube, the tube was sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified by silica gel column chromatography to produce 3.7 g of compound 1-35. (Yield 36%, MS: [M+H]) + =626)

[0615] Synthesis example 1-36

[0616]

[0617] In a shaker tube, compound 1-27 (10 g, 16.2 mmol), PtO2 (1.1 g, 4.9 mmol), and 81 mL of D2O were added. The tube was sealed and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 3.9 g of compound 1-36. (Yield 38%, MS: [M+H]) + =639)

[0618] Synthesis example 1-37

[0619]

[0620] (8-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz31 (26.8 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 26.7 g of compound 1-37_P1. (Yield 75%, MS: [M+H] + =586)

[0621] Compound 1-37_P1 (15 g, 25.6 mmol) and naphthalene-2-ylboronic acid (4.6 g, 26.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.6 g, 76.8 mmol) was then dissolved in 32 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 12.7 g of compound 1-37. (Yield 73%, MS: [M+H] + =678)

[0622] Synthesis example 1-38

[0623]

[0624] (8-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz5 (17.1 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, 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 16.3 g of compound 1-38_P1. (Yield 62%, MS: [M+H] + =434)

[0625] Compound 1-38_P1 (15 g, 34.6 mmol) and triphenylen-2-ylboronic acid (9.9 g, 36.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.3 g, 103.7 mmol) was then 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 14.7 g of compound 1-38. (Yield 68%, MS: [M+H] + =626)

[0626] Synthesis example 1-39

[0627]

[0628] (8-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz32 (32.9 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 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, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.8 g of compound 1-39_P1. (Yield 72%, MS: [M+H] + =636)

[0629] Compound 1-39_P1 (15 g, 23.6 mmol) and dibenzo[b, d]furan-4-ylboronic acid (5.2 g, 24.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (9.8 g, 70.7 mmol) was then dissolved in 29 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 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 11.6 g of compound 1-39. (Yield 64%, MS: [M+H] + =769)

[0630] Synthesis Example 1-40

[0631]

[0632] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium hydroxide (21.4 g, 1065.6 mmol) were added to the mixture at 0°C and stirred for 5 hours to prepare a solution. 1-bromo-8-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The resulting mixed solution of trifluoromethanesulfonic anhydride and deuterium hydroxide was slowly added dropwise to the mixed solution of 1-bromo-8-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene. The mixture was heated to 140°C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred, and then filtered. The filtrate was evaporated under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.4 g of substance 4-1-1. (Yield 42%, MS: [M+H] + =285)

[0633] Material 4-1-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were mixed in 300 mL of 1,4-diboron. The mixture was refluxed in oxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added and stirred thoroughly. Bis(dibenzylideneacetone)palladium (0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were then added. The mixture was reacted for 6 hours, cooled to room temperature, and the organic layer was separated by chloroform and water, and then the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water, 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 g of substance 4-1-2. (Yield 69%, MS: [M+H] + =333)

[0634] Substance 4-1-2 (15 g, 45.1 mmol) and Trz33 (17.8 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 16 g of compound 1-40_P1. (Yield 65%, MS: [M+H] + =546)

[0635] Compound 1-40_P1 (15 g, 27.5 mmol) and dibenzo[b,d]furan-4-ylboronic acid (6.1 g, 28.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.4 g, 82.4 mmol) was then 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 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 1-40. (Yield 62%, MS: [M+H] + =678)

[0636] Synthesis example 1-41

[0637]

[0638] Substance 4-1-2 (15 g, 45.1 mmol) and Trz34 (20.3 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 19.4 g of compound 1-41_P1. (Yield 72%, MS: [M+H] + =599)

[0639] Compound 1-41_P1 (15 g, 25 mmol) and phenylboronic acid (3.2 g, 26.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10.4 g, 75.1 mmol) was then dissolved in 31 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 2 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 9.8 g of compound 1-41. (Yield 61%, MS: [M+H] + =641)

[0640] Synthesis example 1-42

[0641]

[0642] Substance 4-1-2 (15 g, 45.1 mmol) and Trz35 (21.3 g, 47.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.7 g, 135.3 mmol) was then dissolved in 56 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 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 g of compound 1-42_P1. (Yield 61%, MS: [M+H] + =619)

[0643] Compound 1-42_P1 (15 g, 24.2 mmol) and (phenyl-d5) boronic acid (3.2 g, 25.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (10 g, 72.7 mmol) was then dissolved in 30 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 11.1 g of compound 1-42. (Yield 69%, MS: [M+H] + =666)

[0644] Synthesis example 1-43

[0645]

[0646] Compound 1-38 (10 g, 16 mmol), PtO2 (1.1 g, 4.8 mmol), and 80 mL of D2O were added to a shaker tube. The tube was sealed and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 3.5 g of 1-43. (Yield 34%, MS: [M+H]) + =649)

[0647] Synthesis example 1-44

[0648]

[0649] (7-Chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and Trz36 (22 g, 63.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then 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 23.6 g of compound 1-44_P1. (Yield 76%, MS: [M+H] + =511)

[0650] Compound 1-44_P1 (15 g, 29.4 mmol) and naphthalene-2-ylboronic acid (5.3 g, 30.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.2 g, 88.2 mmol) was then dissolved in 100 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 2 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 1-44. (Yield 79%, MS: [M+H] + =603)

[0651] Synthesis example 1-45

[0652]

[0653] Compound 1-44 (10 g, 16.6 mmol), trifluoromethanesulfonic anhydride (46.9 g, 166.2 mmol), and 83 mL of D2O were added to a shaker tube. The tube was sealed and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography to produce 4.4 g of compound 1-45. (Yield 43%, MW = 620)

[0654] [Production of the Second Compound Represented by Chemical Formula 2]

[0655] Synthesis example 2-1

[0656]

[0657] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 1 (22.3 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.7 g of compound 2-1. (Yield 52%, MS: [M+H] + =639)

[0658] Synthesis example 2-2

[0659]

[0660] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 2 (21 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.6 g of compound 2-2. (Yield 70%, MS: [M+H] + =613)

[0661] Synthesis example 2-3

[0662]

[0663] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 3 (21 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.6 g of compound 2-3. (Yield 70%, MS: [M+H] + =613)

[0664] Synthesis Example 2-4

[0665]

[0666] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 4 (26.4 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.1 g of compound 2-4. (Yield 64%, MS: [M+H] + =715)

[0667] Synthesis Example 2-5

[0668]

[0669] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 5 (28 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.3 g of compound 2-5. (Yield 54%, MS: [M+H] + =745)

[0670] Synthesis example 2-6

[0671]

[0672] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 6 (28 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-6. (Yield 58%, MS: [M+H] + =745)

[0673] Synthesis Example 2-7

[0674]

[0675] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 7 (21.2 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.7 g of compound 2-7. (Yield 63%, MS: [M+H] + =655)

[0676] Synthesis example 2-8

[0677]

[0678] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 8 (25 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.1 g of compound 2-8. (Yield 66%, MS: [M+H] + =731)

[0679] Synthesis example 2-9

[0680]

[0681] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 9 (25.7 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-9. (Yield 51%, MS: [M+H] + =745)

[0682] Synthesis example 2-10

[0683]

[0684] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 10 (21 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of compound 2-10. (Yield 56%, MS: [M+H] + =613)

[0685] Synthesis example 2-11

[0686]

[0687] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 11 (25 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.3 g of compound 2-11. (Yield 70%, MS: [M+H] + =689)

[0688] Synthesis example 2-12

[0689]

[0690] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 12 (25 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.8 g of compound 2-12. (Yield 57%, MS: [M+H] + =689)

[0691] Synthesis example 2-13

[0692]

[0693] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 13 (26.4 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.5 g of compound 2-13. (Yield 68%, MS: [M+H] + =715)

[0694] Synthesis example 2-14

[0695]

[0696] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 14 (23.1 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of compound 2-14. (Yield 52%, MS: [M+H] + =653)

[0697] Synthesis example 2-15

[0698]

[0699] Under a nitrogen atmosphere, substance 1 (15 g, 50.5 mmol), amine 15 (27.1 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.9 g of compound 2-15. (Yield 57%, MS: [M+H] + =729)

[0700] Synthesis example 2-16

[0701]

[0702] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 16 (21.2 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.2 g of compound 2-16. (Yield 55%, MS: [M+H] + =655)

[0703] Synthesis example 2-17

[0704]

[0705] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 17 (23.7 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-17. (Yield 54%, MS: [M+H] + =705)

[0706] Synthesis example 2-18

[0707]

[0708] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 18 (23.7 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-18. (Yield 54%, MS: [M+H] + =705)

[0709] Synthesis example 2-19

[0710]

[0711] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 19 (25 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.2 g of compound 2-19. (Yield 55%, MS: [M+H] + =731)

[0712] Synthesis example 2-20

[0713]

[0714] Under a nitrogen atmosphere, substance 2 (15 g, 47.9 mmol), amine 20 (26.5 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-20. (Yield 53%, MS: [M+H] + =761)

[0715] Synthesis example 2-21

[0716]

[0717] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 21 (22.3 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.5 g of compound 2-21. (Yield 70%, MS: [M+H] + =639)

[0718] Synthesis example 2-22

[0719]

[0720] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 22 (25 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, 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 54%, MS: [M+H] + =689)

[0721] Synthesis example 2-23

[0722]

[0723] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 23 (26.4 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.1 g of compound 2-23. (Yield 53%, MS: [M+H] + =715)

[0724] Synthesis example 2-24

[0725]

[0726] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 24 (26.4 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.9 g of compound 2-24. (Yield 58%, MS: [M+H] + =715)

[0727] Synthesis example 2-25

[0728]

[0729] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 25 (27.1 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.6 g of compound 2-25. (Yield 56%, MS: [M+H] + =729)

[0730] Synthesis example 2-26

[0731]

[0732] Under a nitrogen atmosphere, substance 3 (15 g, 50.5 mmol), amine 26 (28 g, 53 mmol), and sodium tert-butoxide (7.3 g, 75.7 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.3 g of compound 2-26. (Yield 54%, MS: [M+H] + =745)

[0733] Synthesis example 2-27

[0734]

[0735] Under a nitrogen atmosphere, substance 4 (15 g, 47.9 mmol), amine 27 (21.2 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, it was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.5 g of compound 2-27. (Yield 50%, MS: [M+H] + =731)

[0736] Synthesis example 2-28

[0737]

[0738] Under a nitrogen atmosphere, substance 4 (15 g, 47.9 mmol), amine 28 (25 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.4 g of compound 2-28. (Yield 64%, MS: [M+H] + =731)

[0739] Synthesis example 2-29

[0740]

[0741] Under a nitrogen atmosphere, substance 4 (15 g, 47.9 mmol), amine 29 (23.7 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, 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 2-29. (Yield 58%, MS: [M+H] + =705)

[0742] Synthesis example 2-30

[0743]

[0744] Under a nitrogen atmosphere, substance 4 (15 g, 47.9 mmol), amine 30 (22.7 g, 50.3 mmol), and sodium tert-butoxide (6.9 g, 71.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the organic layer was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19 g of compound 2-30. (Yield 58%, MS: [M+H] + =685)

[0745] Synthesis example 2-31

[0746]

[0747] Compound 2-1 (10 g, 13.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.6 g, 479.2 mmol) was added to trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0°C and stirred for 10 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the mixed solution of 1,2,4-trichlorobenzene to be prepared, and the temperature was raised to 140 degrees, maintained and stirred. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing 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 obtain 4.6 g of compound 2-31. (Yield 54%, MS: [M+H] + =639)

[0748] Synthesis example 2-32

[0749]

[0750] Compound 2-12 (10 g, 13.8 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.9 g, 496.4 mmol) was added to trifluoromethanesulfonic anhydride (35 g, 124.1 mmol) at 0°C and stirred for 10 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the mixed solution of 1,2,4-trichlorobenzene to be prepared, and the temperature was raised to 140 degrees, maintained and stirred. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing 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 obtain 6.6 g of compound 2-32. (Yield 70%, MS: [M+H] + =689)

[0751] Synthesis example 2-33

[0752]

[0753] Compound 2-27 (10 g, 13.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.6 g, 479.2 mmol) was added to trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0°C and stirred for 10 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the mixed solution of 1,2,4-trichlorobenzene to be prepared, and the temperature was raised to 140 degrees, maintained and stirred. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing 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 obtain 4.9 g of compound 2-33. (Yield 56%, MS: [M+H] + =655)

[0754] Synthesis example 2-34

[0755]

[0756] Compound 2-21 (10 g, 15.7 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (11.3 g, 564.5 mmol) was added to trifluoromethanesulfonic anhydride (39.8 g, 141.1 mmol) at 0°C and stirred for 10 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the mixed solution of 1,2,4-trichlorobenzene to be prepared, and the temperature was raised to 140 degrees, maintained and stirred. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing 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 obtain 6.6 g of compound 2-34. (Yield 64%, MS: [M+H] + =662)

[0757] Example 1

[0758] ITO (indium tin oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0759] On the ITO transparent electrode prepared in this way, the following HI-1 compound was added as a hole injection layer. 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 Then, on the hole transport layer, a film with a thickness of The electron blocking layer was formed by vacuum deposition of the following EB-1 compound.

[0760] Next, on the EB-1 vapor-deposited film, the compound 1-1 prepared in the above-mentioned Synthesis Example 1-1, the compound 2-1 prepared in the above-mentioned Synthesis Example 2-1, and the Dp-7 compound were vacuum-deposited at a weight ratio of 49:49:2 to form Thickness of the red light emitting layer.

[0761] 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

[0762] On the electron injection and transport layer, lithium fluoride (LiF) and The thickness of the aluminum A thickness of 1000 nm is evaporated to form a cathode.

[0763]

[0764] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is maintained at 2 x 10-7 ~5ⅹ10 -6 The organic light-emitting device is thus produced.

[0765] Examples 2 to 130

[0766] In the organic light-emitting device of Example 1, the organic light-emitting device was manufactured by the same method as in Example 1, except that the compound of Chemical Formula 1 described in Table 1 below was used as the first host and the compound of Chemical Formula 2 described in Table 1 below was used as the second host in a 1:1 ratio instead of Compound 1-1 and Compound 2-1 for co-evaporation.

[0767] Comparative Examples 1 to 12

[0768] In the organic light-emitting device of Example 1, the organic light-emitting device was manufactured by the same method as in Example 1, except that the compound of Chemical Formula 1 described in Table 2 below was used as the first host and the compounds A-1 to A-5 described in Table 2 below were used as the second host in a 1:1 ratio instead of Compound 1-1 and Compound 2-1 for co-evaporation.

[0769]

[0770] Experimental Example 1: Characteristic Evaluation of Organic Light-Emitting Devices

[0771] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 130 and Comparative Examples 1 to 12, the voltage, efficiency (15 mA / cm 2 The results are shown in Tables 1 to 4 below. The lifespan T95 was measured based on a standard of 7000 nits, and T95 refers to the time required for the initial lifespan to decrease to 95%.

[0772] [Table 1]

[0773]

[0774] [Table 2]

[0775]

[0776] [Table 3]

[0777]

[0778] [Table 4]

[0779]

[0780] As shown in Tables 1 to 4 above, the organic light-emitting devices of the examples in which the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 are simultaneously used as host materials of the light-emitting layer exhibit excellent driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light-emitting devices of the comparative examples in which the comparative compound is used as the second host.

[0781] In particular, the devices according to the Examples exhibited improved driving voltage, efficiency, and lifetime characteristics compared to all devices in the Comparative Examples, which used the compound represented by Chemical Formula 1 as the first host and Comparative Compounds A-1 to A-45 as the second host. This confirms that the combination of the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 as a common host effectively achieves energy transfer to the red dopant within the red light-emitting layer. This is believed to be due to the fact that the common host combination of the Examples maintains a more stable equilibrium within the light-emitting layer than the common host combination of the Comparative Example devices.

[0782] Therefore, it was confirmed that the combined use of the first and second compounds as host materials in an organic light-emitting device can improve the driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting device. Considering that the luminous efficiency and lifetime characteristics of an organic light-emitting device generally exhibit a trade-off relationship, it can be seen that the organic light-emitting device using the combination of the compounds of the present invention exhibits significantly improved device characteristics compared to the comparative example device.

[0783] [Explanation of symbols]

[0784] 1: Substrate 2: Anode

[0785] 3: Light-emitting layer 4: Cathode

[0786] 5: Hole injection layer 6: Hole transport layer

[0787] 7: Electron blocking layer 8: Hole blocking layer

[0788] 9: Electron injection and transport layer.

Claims

1. An organic light-emitting device, comprising: anode, a cathode disposed opposite to the anode, and A light-emitting layer is provided 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 groups, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl, R is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl, but at least one of R is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl, h is 0, 1, or 2, k is an integer from 1 to 7, [Chemical Formula 2] In the chemical formula 2, X is O or S, L'1 to L'3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene groups, Ar' is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of 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, h 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. 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. The organic light-emitting device according to claim 1 , wherein: Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl, wherein Ar1 and Ar2 are unsubstituted; or are 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. The organic light-emitting device according to claim 1 , wherein: At least one of R is any one of an aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any one of a heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, and the rest are hydrogen or deuterium, The aryl and heteroaryl groups are unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

7. The organic light-emitting device according to claim 1, wherein k is 1, R is any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, or k is 2 to 7, one of R is any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene and fluoranthenyl; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzonaphthothiophenyl, and the rest are deuterium, The aryl and heteroaryl groups are unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

8. The organic light-emitting device according to claim 1, wherein is any one of the substituents represented by the following Chemical Formulas 1a to 1g: In the chemical formulas 1a to 1g, R' is substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing one heteroatom of N, O and S 2-20 heteroaryl, d is an integer from 0 to 6.

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

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 2d: In the chemical formulas 2a to 2d, R'1 and a are the same as defined in claim 1. The organic light-emitting device according to claim 1 , wherein: is any one of the substituents represented by the following chemical formulas 3a to 3d: In the chemical formulas 3a to 3d, X, 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 is substituted or unsubstituted C 6-12 Arylene.

13. The organic light emitting device according to claim 1, wherein L'2 is a single bond.

14. The organic light emitting device according to claim 1, wherein L'3 is a single bond, or a substituted or unsubstituted C 6-12 Arylene.

15. The organic light emitting device according to claim 1, wherein Ar' is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl, wherein Ar' is unsubstituted; or substituted with one or more substituents selected from deuterium, halogen, cyano, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, and deuterium-substituted or unsubstituted naphthyl.

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

17. The organic light emitting device according to claim 1, wherein: The second compound is represented by the following chemical formula 2A or 2B: [Chemical Formula 2A] [Chemical Formula 2B] In the chemical formulas 2A and 2B, R'3 is hydrogen or deuterium, c is an integer from 0 to 4, X, L'2, L'3, Ar', R'1, R'2, a and b are the same as defined in claim 1.

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

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