Novel compound and organic light-emitting device using same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2022-0121090 filed on September 22, 2022 and Korean Patent Application No. 10-2023-0126570 filed on September 21, 2023, and incorporates all the contents disclosed in the documents of the Korean patent applications as part of this specification.

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

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

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

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

[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 novel compounds and organic light-emitting devices comprising the same.

[0012] Solution to the problem

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

[0014] [Chemical formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Y is each independently O or S,

[0018] R1 is each independently hydrogen or deuterium,

[0019] L1, L2 and L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and

[0020] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 Heteroaryl,

[0021] However, at least one of R1, L1 to L3, Ar1 and Ar2 is deuterium or substituted with deuterium.

[0022] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains the compound represented by the above chemical formula 1.

[0023] Effects of the Invention

[0024] The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, lower driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] 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 .

[0026] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown. DETAILED DESCRIPTION

[0027] In the following, the present invention will be described in more detail to help understanding the present invention.

[0028] In this manual, It represents the bond to other substituents.

[0029] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or substituted or unsubstituted with one or more substituents in a heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0030] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0031]

[0032] In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the group may be a group of the following structural formula, but is not limited thereto.

[0033]

[0034] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0035]

[0036] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0037] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0038] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0039] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0040] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0041] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0042] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0043] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0044] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0045] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the aryl group described above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in aralkenyl is the same as the examples of the alkenyl group described above. In the present specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above-mentioned description of the aryl group or cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above-mentioned description of the heterocyclic group can be applied.

[0046] 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.

[0047] In addition, "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with 1 to 9 deuteriums in the substitutable hydrogens". As an example, the term "unsubstituted or substituted with deuterium phenanthrenyl" can be understood to mean "unsubstituted or substituted with 1 to 9 deuteriums in the phenanthrenyl structure" when considering that the maximum number of hydrogens that can be substituted with deuteriums is 9.

[0048] In addition, the meaning of "deuterated structure" refers to compounds, divalent linking groups, or monovalent substituents including all structures in which at least one hydrogen is replaced by deuterium. As an example, the deuterated structure of phenyl shown below can be understood as referring to all structures in which at least one hydrogen that can be replaced in phenyl is replaced by deuterium and monovalent substituents.

[0049]

[0050] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to the ratio of the number of deuterium substituted in the compound to the total number of hydrogens that can exist (the sum of the number of hydrogens that can be substituted with deuterium in the compound and the number of substituted deuteriums) calculated as a percentage. Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogens that can be substituted with deuterium in the compound are substituted with deuterium.

[0051] In this case, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be measured by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry), etc., and are measured according to commonly known methods. More specifically, when using MALDI-TOF MS, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be determined by analyzing the number of deuterium substituted in the compound through MALDI-TOF MS, and then calculating the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist as a percentage.

[0052] The present invention provides a compound represented by the above Chemical Formula 1.

[0053] Specifically, the compound represented by the above chemical formula 1 is a compound having a tertiary amine group of a specific structure bonded to a specific position of the benzene ring at one end of the mother core structure of benzodibenzofuran or benzodibenzothiophene, that is, the second carbon position after the oxygen or sulfur atom in the terminal benzene ring fused with benzothiophene or benzofuran, and is characterized in that at least one of the substituents of the above compound is deuterium or is substituted with deuterium. In particular, the above compound has a long lifespan characteristic compared with a compound having a protium substituent, and can therefore be effectively used in the light-emitting layer of an organic light-emitting device.

[0054] More specifically, in the above Chemical Formula 1,

[0055] Y is each independently O or S,

[0056] R1 is each independently hydrogen or deuterium,

[0057] L1, L2 and L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and

[0058] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 Heteroaryl,

[0059] However, at least one of R1, L1 to L3, Ar1 and Ar2 is deuterium or is substituted with deuterium.

[0060] Preferably, in the above Chemical Formula 1, all Y are O, or all Y are S, or one of Y is S and the others are O.

[0061] In one aspect, at least one of R1 is deuterium, and the rest of R1 can be hydrogen. Preferably, at least 3 or 3 to 9 of R1 can be deuterium, or at least 4 or 4 to 9 can be deuterium. In this case, the rest of R1 can be hydrogen. Alternatively, all R1 can be deuterium.

[0062] In particular, in the above Chemical Formula 1, when the mother core structure of benzobisbenzofuran or benzobisbenzothiophene is substituted with deuterium, that is, when at least one of R1 is deuterium, it can be represented by the following Chemical Formula 1-1.

[0063] [Chemical formula 1-1]

[0064]

[0065] In the above chemical formula 1,

[0066] Y is each independently O or S,

[0067] D is deuterium,

[0068] n is an integer from 1 to 9,

[0069] L1, L2 and L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and

[0070] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 Heteroaryl.

[0071] In the above chemical formula 1-1, n is the number of deuterium substituted in the core structure of benzobisbenzofuran or benzobisbenzothiophene, as represented by b in a representative example described later. Here, n>0, n is at least 1 or 1 to 9.

[0072] On the one hand, in the above Chemical Formula 1 and Chemical Formula 1-1, L1, L2 and L3 may each be a single bond; or may be a phenylene group, a phenylene group substituted with at least one deuterium, a naphthylene group, or a naphthylene group substituted with at least one deuterium.

[0073] As an example, L1, L2 and L3 may each be a single bond; or may be a phenylene group, a phenylene group substituted with at least one or 1 to 4 deuteriums, a naphthylene group, or a naphthylene group substituted with 1 or more or 1 to 6 deuteriums.

[0074] Specifically, L1, L2 and L3 each may be a single bond, or may be any one selected from the following groups.

[0075]

[0076] More specifically, L1 and L2 may each independently be a single bond, or a phenylene group substituted with hydrogen or deuterium.

[0077] As an example, L1 and L2 may each independently be a single bond; or may be a phenylene group, a phenylene group substituted with 4 deuterium groups, a naphthyl group, or a naphthyl group substituted with 3 or more or 3 to 6 deuterium groups. Preferably, L1 and L2 may each independently be a single bond; or may be a phenylene group, or a phenylene group substituted with 4 deuterium groups.

[0078] In addition, L3 may be a phenylene group substituted with hydrogen or deuterium.

[0079] As an example, L3 may be a phenylene group or a phenylene group substituted with four deuteriums.

[0080] Preferably, at least one of L1, L2 and L3 may be a phenylene group substituted with deuterium.

[0081] On the one hand, in the above Chemical Formula 1 and Chemical Formula 1-1, Ar1 and Ar2 can each independently be a C substituted by hydrogen or deuterium. 6-19 Aryl or C substituted by hydrogen or deuterium 6-14 Aryl, or C may be substituted by hydrogen or deuterium 2-19 Heteroaryl or C substituted by hydrogen or deuterium 2-12 Heteroaryl.

[0082] Specifically, at least one of Ar1 and Ar2 may be a C substituted with deuterium. 6-19 Aryl or C substituted by hydrogen or deuterium 6-14 Aryl, or C substituted by deuterium 2-19 Heteroaryl or C substituted by hydrogen or deuterium 2-12 Heteroaryl.

[0083] More specifically, Ar1 and Ar2 can each independently be a phenyl group substituted by hydrogen or deuterium, a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, a phenanthryl group substituted by hydrogen or deuterium, a dibenzofuranyl group substituted by hydrogen or deuterium, a dibenzothienyl group substituted by hydrogen or deuterium, or a carbazolyl group substituted by hydrogen or deuterium.

[0084] Preferably, Ar1 and Ar2 can each independently be phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, biphenyl substituted by 1 to 9 deuteriums, naphthyl, naphthyl substituted by 1 to 7 deuteriums, phenanthryl, phenanthryl substituted by 1 to 9 deuteriums, dibenzofuranyl, dibenzofuranyl substituted by 1 to 7 deuteriums, dibenzothienyl, dibenzothienyl substituted by 1 to 7 deuteriums, carbazolyl, or carbazolyl substituted by 1 to 8 deuteriums.

[0085] As an example, in the above Chemical Formula 1, Ar1 or Ar2 may each be any one selected from the following groups.

[0086]

[0087]

[0088] More specifically, Ar1 and Ar2 can each independently be phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, biphenyl substituted by 1 to 9 deuteriums, naphthyl, naphthyl substituted by 1 to 7 deuteriums, phenanthryl, phenanthryl substituted by 1 to 9 deuteriums, dibenzofuranyl, dibenzofuranyl substituted by 1 to 7 deuteriums, dibenzothienyl, or dibenzothienyl substituted by 1 to 7 deuteriums.

[0089] On the one hand, in the above Chemical Formula 1 and Chemical Formula 1-1, at least one of Ar1 and Ar2 may include two or more benzene rings.

[0090] Specifically, at least one of Ar1 and Ar2 may be a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, a phenanthryl group substituted by hydrogen or deuterium, a dibenzofuranyl group substituted by hydrogen or deuterium, or a dibenzothiophenyl group substituted by hydrogen or deuterium.

[0091] More specifically, at least one of Ar1 and Ar2 can be a biphenyl group, a biphenyl group substituted by 1 to 9 deuteriums, a naphthyl group, a naphthyl group substituted by 1 to 7 deuteriums, a phenanthryl group, a phenanthryl group substituted by 1 to 9 deuteriums, a dibenzofuranyl group, a dibenzofuranyl group substituted by 1 to 7 deuteriums, a dibenzothiophenyl group, or a dibenzothiophenyl group substituted by 1 to 7 deuteriums.

[0092] As an example, at least one of Ar1 and Ar2 can be a biphenyl group substituted by 5 or more or 5 to 9 deuteriums, a naphthyl group substituted by 4 or more or 4 to 7 deuteriums, a phenanthryl group substituted by 4 or more or 4 to 9 deuteriums, a dibenzofuranyl group substituted by 2 or more or 2 to 7 deuteriums, or a dibenzothiophenyl group substituted by 2 or more or 2 to 7 deuteriums.

[0093] On the other hand, in the above Chemical Formula 1 and Chemical Formula 1-1, at least one of Ar1 and Ar2 may be a C 6-19 Aryl, or C substituted by hydrogen or deuterium 6-14 Aryl.

[0094] Specifically, at least one of Ar1 and Ar2 may be a phenyl group substituted by hydrogen or deuterium, a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, or a phenanthryl group substituted by hydrogen or deuterium.

[0095] More specifically, at least one of Ar1 and Ar2 may be phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, biphenyl substituted by 1 to 9 deuteriums, naphthyl, naphthyl substituted by 1 to 7 deuteriums, phenanthryl, or phenanthryl substituted by 1 to 9 deuteriums.

[0096] As an example, at least one of Ar1 and Ar2 can be phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl substituted by 5 or more or 5 to 9 deuteriums, naphthyl substituted by 4 or more or 4 to 7 deuteriums, or phenanthryl substituted by 4 or more or 4 to 9 deuteriums.

[0097] On the one hand, in the above Chemical Formula 1 and Chemical Formula 1-1, at least one of R1, L1 to L3, Ar1, and Ar2 may be deuterium or may be substituted with deuterium.

[0098] Specifically, at least one of R1 may be deuterium, or at least one of L1 to L3 may be a phenylene group substituted with deuterium, or at least one of Ar1 and Ar2 may be substituted with deuterium.

[0099] More specifically, at least one of R1 may be deuterium, and at the same time, at least one of L1 to L3 may be a phenylene group substituted with deuterium, or at least one of Ar1 and Ar2 may be substituted with deuterium.

[0100] In a preferred embodiment, in the above Chemical Formula 1 and Chemical Formula 1-1, when L1 is a single bond, Ar1 can be a C 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl, L1 is substituted or unsubstituted C 6-60 In the case of an arylene group, Ar1 may be a C substituted by hydrogen or deuterium. 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 In addition, when L2 is a single bond, Ar2 is a C 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl, L2 is substituted or unsubstituted C 6-60 In the case of an arylene group, Ar2 may be a C 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl.

[0101] Specifically, in the above Chemical Formula 1 and Chemical Formula 1-1, when L1 is a single bond, Ar1 can be phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl substituted by hydrogen or deuterium, or dibenzothiopheneyl substituted by hydrogen or deuterium, and L1 is a substituted or unsubstituted C 6-60In the case of an arylene group, Ar1 may be a phenyl group substituted by hydrogen or deuterium, a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, a phenanthryl group substituted by hydrogen or deuterium, a dibenzofuranyl group substituted by hydrogen or deuterium, or a dibenzothienyl group substituted by hydrogen or deuterium. In addition, when L2 is a single bond, Ar2 may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group substituted by hydrogen or deuterium, or a dibenzothienyl group substituted by hydrogen or deuterium, and L2 is a substituted or unsubstituted C 6-60 In the case of an arylene group, Ar2 may be a phenyl group substituted by hydrogen or deuterium, a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, a phenanthryl group substituted by hydrogen or deuterium, a dibenzofuranyl group substituted by hydrogen or deuterium, or a dibenzothiophenyl group substituted by hydrogen or deuterium.

[0102] In one aspect, the above compounds contain at least one deuterium.

[0103] The total number of deuterium substitutions in the above compounds and the number of substitutions of each substituent are as described with reference to a, b, c, d, e, f, and g in the structural formula of a representative example described later, and specific descriptions are omitted.

[0104] In particular, with respect to the above compounds, at least one of the substituents of the benzobisbenzofuran or benzobisbenzothiophene core structure, ie, R1, in the above Chemical Formula 1 and Chemical Formula 1-1 may be deuterium.

[0105] In this case, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the above-mentioned compound may be 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 28% or more, 30% or more, 32% or more, 35% or more, 38% or more, 40% or more, 42% or more, 45% or more, 48% or more, 50% or more, 52% or more, 55% or more, 58% or more, 60% or more, 62% or more, 65% or more, 68% or more, 70% or more, 72% or more, 75% or more, 78% or more, 80% or more, or 90% or more and 100% or less.

[0106] As an example, the deuterium substitution rate of the above-mentioned compound can be greater than 20%, greater than 25%, greater than 28%, greater than 30%, greater than 32%, greater than 35%, greater than 38%, greater than 40%, greater than 42%, greater than 45%, greater than 48%, or greater than 50% and less than 100%, less than 98%, less than 95%, less than 92%, less than 90%, less than 88%, less than 85%, less than 82%, less than 80%, less than 78%, less than 75%, less than 72%, less than 70%, less than 68%, less than 65%, less than 62%, less than 60%, less than 58%, or less than 55%.

[0107] In addition, the compound may contain at least one deuterium or 1 to 50 deuteriums. More specifically, the compound may contain at least 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, or 11 or more and 50 or less, 40 or less, 35 or less, 32 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 19 or less, 18 or less, 17 or less, or 16 or less deuteriums.

[0108] As an example, the compounds represented by the above Chemical Formula 1 and Chemical Formula 1-1 may be substituted with at least 3 or 3 to 35 deuteriums, specifically, at least 4 or 4 to 30 deuteriums, or at least 6 or 6 to 25 deuteriums, or at least 8 or 8 to 20 deuteriums. More specifically, at least 11 or 11 to 16 deuteriums may be substituted. For example, at least one of R1, L1 to L3 and Ar1 to Ar2 may be at least 3 or 3 to 35 deuteriums or may be substituted with at least 3 or 3 to 35 deuteriums, or may be at least 4 or 4 to 30 deuteriums or may be substituted with at least 4 or 4 to 30 deuteriums, or may be at least 6 or 6 to 25 deuteriums or may be substituted with at least 6 or 6 to 25 deuteriums, or may be at least 8 or 8 to 20 deuteriums or may be substituted with at least 8 or 8 to 20 deuteriums. More specifically, at least one of R1, L1 to L3 and Ar1 to Ar2 may be at least 11 or 11 to 16 deuteriums or may be substituted with at least 11 or 11 to 16 deuteriums.

[0109] As an example, all hydrogens included in the above Chemical Formula 1 may be substituted with deuterium. Representative examples of the compound represented by the above Chemical Formula 1 are shown below.

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] In the above formula, D is deuterium, a is the number of deuterium substitutions, and a>0.

[0167] Specifically, a in the above structural formula is the total number of deuterium substitutions in the above compound, and a>0 is the sum of the number of deuterium substitutions of each substituent. a in the above structural formula can be at least 1 or 1 to 50. More specifically, a in the above structural formula can be at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11 and 50 or less, 40 or less, 35 or less, 32 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 19 or less, 18 or less, 17 or less, or 16 or less. As an example, a in the above structural formula can be at least 3 or 3 to 35, or at least 4 or 4 to 30, or at least 6 or 6 to 25, or at least 8 or 8 to 20. More specifically, a in the above structural formula can be at least 11 or 11 to 16.

[0168] More specifically, the number of deuterium substitutions of each substituent constituting a in the above structural formula can be represented by b, c, d, e, f, and g, respectively, as shown in a specific example described later. In this case, b is the number of deuterium substitutions on the benzodibenzofuranyl or benzodibenzothiophene parent core structure in the above chemical formula 1, and can be b>0. For example, b can be at least 1 or 1 to 9. In addition, c is the number of deuterium substitutions on the L1 substituent as a linking group in the above chemical formula 1, d is the number of deuterium substitutions on the L2 substituent as a linking group in the above chemical formula 1, e is the number of deuterium substitutions on the L3 substituent as a linking group in the above chemical formula 1, f is the number of deuterium substitutions on the Ar1 substituent as a tertiary amine group substituent in the above chemical formula 1, and g is the number of deuterium substitutions on the Ar2 substituent as a tertiary amine group substituent in the above chemical formula 1. Here, the sum of c+d+e+f+g can be 0 to 49.

[0169] On the one hand, a specific example of the compound represented by the above Chemical Formula 1 is shown below.

[0170]

[0171]

[0172]

[0173] In the above structural formula, D is deuterium, a is the total number of deuterium substitutions, a>0, and is the sum of the number of deuterium substitutions of each substituent. The specific range is as described above.

[0174] On the one hand, a more specific example of the compound represented by the above Chemical Formula 1 is shown below.

[0175]

[0176]

[0177]

[0178] In the above formula, D is deuterium, and a is the total number of deuterium substitutions in the above compound, a>0, which is the sum of the number of deuterium substitutions of each substituent. In this case, a can be at least 1 or 1 to 50, and the specific range is as described above. In addition, b, c, d, e, f, and g are the number of deuterium substitutions of each substituent in the above formula, b can be at least 1 or 1 to 9, and the sum of c+d+e+f+g can be 0 to 49, and the specific range is as described above.

[0179] On the one hand, the compound represented by the above Chemical Formula 1 can be produced by a production method as shown in the following Reaction Formula 1. The above production method can be further embodied in the synthesis examples described below.

[0180] [Reaction 1]

[0181]

[0182] In the above reaction formula 1, Y, R1, L1, L2, L3, Ar1 and Ar2 are the same as those in the above chemical formula 1.

[0183] Q1 is BO2C2(CH3)4 or B(OH)2,

[0184] Q2 is a halogen,

[0185] p and q are each 0 or 1, but at least one of p and q is 0 and the rest of p and q are 1.

[0186] As an example, Q1 is B(OH)2.

[0187] As an example, Q2 is Cl, Br or I, preferably Cl or Br, more preferably Cl.

[0188] Specifically, the above reaction formula 1 is a reaction in which a tertiary amine substituent of a specific structure is introduced at a specific position of the benzene ring at one end of the benzodibenzofuran or benzodibenzothiophene mother core structure, that is, at the second carbon position after the oxygen or sulfur atom in the terminal benzene ring fused with benzothiophene or benzofuran, and substituted by deuterium. Here, in the above reaction formula 1, in the case of using a reactant substituted with deuterium, the deuterium substitution reaction can be omitted, or the deuterium substitution reaction can be carried out together in order to further replace deuterium on the remaining substituents. In the above reaction formula 1, the reaction of introducing a tertiary amine substituent of a specific structure on the above-mentioned specific structure of the benzodibenzofuran or benzodibenzothiophene mother core structure is completed by reacting with a palladium catalyst (Pd catalyst) in the presence of a base. In addition, in the above-mentioned compound, the reaction of replacing the hydrogen substituent with deuterium is completed by reacting the compound introduced with a tertiary amine in the presence of deuterium oxide (D2O) and trifluoromethanesulfonic anhydride (Trifluoromethanesulfonic anhydride) (Tf2O). The specific reaction conditions of such reaction formula 1 can be carried out with reference to the known reactions known in the art. The above-mentioned manufacturing method can be more specifically described in the synthesis examples described later.

[0189] In addition, in the above reaction formula 1, as the base component, potassium carbonate (K2CO3), sodium bicarbonate (NaHCO3), cesium carbonate (Cs2CO3), sodium acetate (NaOAc), potassium acetate (KOAc), sodium ethoxide (NaOEt), sodium tert-butoxide (NaOtBu), triethylamine (Et3N), or N,N-diisopropylethylamine (EtN(iPr)2) etc. can be used. Preferably, the above base component can be potassium carbonate (K2CO3), cesium carbonate (Cs2CO3), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), or N,N-diisopropylethylamine (EtN(iPr)2). In particular, in the above reaction formula 1, potassium carbonate (K2CO3) can be used as the base component.

[0190] In the above reaction formula 1, as the above palladium catalyst, bis(tri-(tert-butyl)phosphine)palladium(0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu3)2), tetrakis(triphenylphosphine)palladium(0) (tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4), tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0) )(bis(dibenzylideneacetone)palladium(0), Pd(dba)2), or palladium(II)acetate (palladium(II)acetate, Pd(OAc)2), etc. Preferably, the palladium catalyst may be bis(tri(tert-butyl)phosphine)palladium(0) (Pd(P-tBu3)2), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), or bis(dibenzylideneacetone)palladium(0) (Pd(dba)2). In particular, in the above reaction formula 1, bis(tri(tert-butyl)phosphine)palladium(0) (Pd(P-tBu3)2) may be used as a catalyst.

[0191] In one aspect, the present invention provides an organic light-emitting device comprising the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the above first electrode, and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers comprises the compound represented by the above Chemical Formula 1.

[0192] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, but may also be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0193] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound represented by Chemical Formula 1.

[0194] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound represented by Chemical Formula 1.

[0195] In addition, the organic layer may include an electron blocking layer, and the electron blocking layer may include the compound represented by Chemical Formula 1.

[0196] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0197] In addition, the light-emitting layer further contains a dopant compound.

[0198] In addition, the light emitting layer includes the compound of Chemical Formula 1 and a dopant.

[0199] As an example, the light emitting layer includes the compound of Chemical Formula 1 and the dopant in a weight ratio of 100:1 to 1:1.

[0200] In addition, the light emitting layer includes the compound of Chemical Formula 1 and a dopant, and the compound of Chemical Formula 1 and the dopant are included in a content ratio of 100:1 to 2:1.

[0201] In addition, the light emitting layer includes the compound of Chemical Formula 1 and the dopant in a weight ratio of 100:1 to 5:1, or 100:1 to 10:1, or 100:1 to 20:1, or 100:1 to 30:1.

[0202] As an example, the dopant is a metal complex.

[0203] Specifically, the dopant is an iridium-based metal complex.

[0204] In addition, the organic layer includes a light-emitting layer, the light-emitting layer contains a dopant, and the dopant substance is selected from the following structural formulas.

[0205]

[0206]

[0207]

[0208] The structures explicitly described above are dopant compounds and are not limited thereto.

[0209] In addition, the organic layer may include a hole blocking layer, and the hole blocking layer may include the compound represented by Chemical Formula 1.

[0210] In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or the layer that simultaneously injects and transports electrons includes the compound represented by Chemical Formula 1.

[0211] In addition, the organic layer includes a light-emitting layer and an electron blocking layer, and the light-emitting layer or the electron blocking layer may include the compound represented by Chemical Formula 1.

[0212] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and 2 .

[0213] Figure 1 The figure shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above light emitting layer.

[0214] 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. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, and electron injection and transport layer. Specifically, the compound represented by the above chemical formula 1 may be contained in the above light-emitting layer, for example, as a host material of the light-emitting layer.

[0215] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0216] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0217] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. In particular, the compound represented by the above chemical formula 1 has excellent solubility in the solvent used in the solution coating method, and thus is easily applicable to the solution coating method. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited thereto.

[0218] Therefore, the present invention provides a coating composition including the compound represented by the above Chemical Formula 1 and a solvent.

[0219] The above-mentioned solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention. As an example, chlorine-based solvents such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc.; tetrahydrofuran, dichloroethane, etc. ether solvents such as alkane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylol, mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol ethyl ether acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, propylene glycol, diethoxymethane , triethylene glycol monoethyl ether, propylene glycol, 1,2-hexanediol and other polyols and their derivatives; methanol, ethanol, propanol, isopropanol, cyclohexanol and other alcohol solvents; dimethyl sulfoxide and other sulfoxide solvents; and N-methyl-2-pyrrolidone, N,N-dimethylformamide and other amide solvents; butyl benzoate, methyl 2-methoxybenzoate and other benzoate solvents; tetralin; 3-phenoxy-toluene and other solvents. In addition, one of the above solvents can be used alone, or two or more solvents can be used in combination.

[0220] In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

[0221] In addition, the present invention provides a method for forming a functional layer using the coating composition. Specifically, the method comprises the following steps: coating the coating composition according to the present invention through a solution process; and heat treating the coated coating composition.

[0222] In the heat treatment step, the heat treatment temperature is preferably 150° C. to 230° C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed under an inert gas atmosphere such as argon or nitrogen.

[0223] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0224] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0225] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0226] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0227] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0228] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3), carbazole compounds, dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0229] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Preferably, the compound according to the present invention is used as the host material.

[0230] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto. Preferably, an iridium-based metal complex is used as the above-mentioned dopant material.

[0231] The above-mentioned light-emitting layer can be a red light-emitting layer. When the compound according to the present invention is used as a main material, the stability of electrons and holes is increased, and the energy transfer from the main body to the red dopant is well formed. At the same time, the driving voltage, luminous efficiency and life characteristics of the organic light-emitting device can be improved.

[0232] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for materials with large electron mobility. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0233] The electron injection layer is a layer for injecting electrons from the electrode, and preferably uses the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0234] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0235] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a bidirectional light-emitting device, and in particular, may be a bottom emission device requiring relatively high light-emitting efficiency.

[0236] In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to being included in an organic light-emitting device.

[0237] The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0238] [Example]

[0239] Synthesis example 1

[0240]

[0241] Under nitrogen atmosphere, compound substance (sub) 1 (15 g, 51.2 mmol) and amine compound amine 1 (15.6 g, 53.8 mmol) were added to 300 mL of tetrahydrofuran (THF), stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the filtrate was 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_P1. (yield 60%, MS: [M+H] + =502).

[0242] Under nitrogen atmosphere, the above compound 1_P1 (10 g, 19.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene (1,2,4-trichlorobenzene) (TCB) and stirred at room temperature. In another container, heavy water (D2O, 14.4 g, 717.7 mmol) was added to trifluoromethanesulfonic anhydride (Tf2O, 45 g, 159.5 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 1. (Yield 51%, MS: [M+H] + =513).

[0243] Synthesis example 2

[0244]

[0245] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 2 (22.3 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound 2_P1. (Yield 73%, MS: [M+H] + =628).

[0246] Under a nitrogen atmosphere, the above compound 2_P1 (10 g, 15.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (11.5 g, 573.5 mmol) was added to trifluoromethanesulfonic anhydride (36 g, 127.4 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C while stirring while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7 g of compound 2. (Yield 69%, MS: [M+H] + =641).

[0247] Synthesis example 3

[0248]

[0249] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 3 (23.7 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 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 22.8 g of compound 3_P1. (Yield 68%, MS: [M+H] + =654).

[0250] Under a nitrogen atmosphere, the above compound 3_P1 (10 g, 15.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (11 g, 550.6 mmol) was added to trifluoromethanesulfonic anhydride (34.5 g, 122.4 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.1 g of compound 3. (Yield 50%, MS: [M+H] + =669).

[0251] Synthesis example 4

[0252]

[0253] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 4 (22.3 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 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 24.1 g of compound 4_P1. (Yield 75%, MS: [M+H] + =628).

[0254] Under a nitrogen atmosphere, the above compound 4_P1 (10 g, 15.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (11.5 g, 573.5 mmol) was added to trifluoromethanesulfonic anhydride (36 g, 127.4 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 4. (Yield 51%, MS: [M+H] + =640).

[0255] Synthesis example 5

[0256]

[0257] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 5 (20.4 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.2 g of compound 5_P1. (Yield 60%, MS: [M+H] + =592).

[0258] Under a nitrogen atmosphere, the above compound 5_P1 (10 g, 16.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (12.2 g, 608.4 mmol) was added to trifluoromethanesulfonic anhydride (38.1 g, 135.2 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.1 g of compound 5. (yield 60%, MS: [M+H] + =605).

[0259] Synthesis example 6

[0260]

[0261] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 6 (24.5 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25 g of compound 6_P1. (Yield 73%, MS: [M+H] + =668).

[0262] Under a nitrogen atmosphere, the above compound 6_P1 (10 g, 15 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.8 g, 539.1 mmol) was added to trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C while stirring while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.6 g of compound 6. (Yield 55%, MS: [M+H] + =684).

[0263] Synthesis Example 7

[0264]

[0265] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 7 (24.5 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.6 g of compound 7_P1. (Yield 69%, MS: [M+H] + =668).

[0266] Under a nitrogen atmosphere, the above compound 7_P1 (10 g, 15 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.8 g, 539.1 mmol) was added to trifluoromethanesulfonic anhydride (33.8 g, 119.8 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.7 g of compound 7. (Yield 56%, MS: [M+H] + =683).

[0267] Synthesis example 8

[0268]

[0269] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 8 (21.3 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound 8_P1. (Yield 70%, MS: [M+H] + =608).

[0270] Under a nitrogen atmosphere, the above compound 8_P1 (10 g, 16.5 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (11.9 g, 592.4 mmol) was added to trifluoromethanesulfonic anhydride (37.1 g, 131.6 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.7 g of compound 8. (yield 56%, MS: [M+H] + =622).

[0271] Synthesis example 9

[0272]

[0273] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 9 (25.4 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.4 g of compound 9_P1. (Yield 61%, MS: [M+H] + =684).

[0274] Under a nitrogen atmosphere, the above compound 9_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.5 g, 526.4 mmol) was added to trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C while stirring while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.1 g of compound 9. (Yield 50%, MS: [M+H] + =697).

[0275] Synthesis example 10

[0276]

[0277] Under a nitrogen atmosphere, compound substance 1 (15 g, 51.2 mmol) and amine compound amine 10 (29.5 g, 53.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 21.2 g, 153.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 10_P1. (Yield 68%, MS: [M+H] + =760).

[0278] Under a nitrogen atmosphere, the above compound 10_P1 (10 g, 13.2 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.5 g, 473.7 mmol) was added to trifluoromethanesulfonic anhydride (29.7 g, 105.3 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 10. (yield 68%, MS: [M+H] + =772).

[0279] Synthesis example 11

[0280]

[0281] Under a nitrogen atmosphere, compound substance 2 (15 g, 48.6 mmol) and amine compound amine 11 (18.6 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 17.6 g of compound 11_P1. (Yield 61%, MS: [M+H] + =594).

[0282] Under a nitrogen atmosphere, the above compound 11_P1 (10 g, 16.8 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (12.1 g, 606.3 mmol) was added to trifluoromethanesulfonic anhydride (38 g, 134.7 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 11. (yield 66%, MS: [M+H] + =605).

[0283] Synthesis example 12

[0284]

[0285] Under a nitrogen atmosphere, compound substance 2 (15 g, 48.6 mmol) and amine compound amine 12 (25.1 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 24.8 g of compound 12_P1. (Yield 71%, MS: [M+H] + =720).

[0286] Under a nitrogen atmosphere, the above compound 12_P1 (10 g, 13.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10 g, 500.1 mmol) was added to trifluoromethanesulfonic anhydride (31.4 g, 111.1 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 12. (yield 68%, MS: [M+H] + =732).

[0287] Synthesis example 13

[0288]

[0289] Under a nitrogen atmosphere, compound substance 2 (15 g, 48.6 mmol) and amine compound amine 13 (23.2 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 21.9 g of compound 13_P1. (Yield 66%, MS: [M+H] + =684).

[0290] Under a nitrogen atmosphere, the above compound 13_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.5 g, 526.4 mmol) was added to trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.2 g of compound 13. (Yield 61%, MS: [M+H] + =699).

[0291] Synthesis Example 14

[0292]

[0293] Under a nitrogen atmosphere, compound substance 2 (15 g, 48.6 mmol) and amine compound amine 14 (24 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 24.5 g of compound 14_P1. (Yield 72%, MS: [M+H] + =700).

[0294] Under a nitrogen atmosphere, the above compound 14_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.3 g, 514.4 mmol) was added to trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.9 g of compound 14. (yield 58%, MS: [M+H] + =714).

[0295] Synthesis Example 15

[0296]

[0297] Under a nitrogen atmosphere, compound substance 2 (15 g, 48.6 mmol) and amine compound amine 15 (27.9 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 27.9 g of compound 15_P1. (Yield 74%, MS: [M+H] + =776).

[0298] Under a nitrogen atmosphere, the above compound 15_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.3 g, 463.9 mmol) was added to trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 15. (yield 51%, MS: [M+H] + =787).

[0299] Synthesis Example 16

[0300]

[0301] Under a nitrogen atmosphere, compound substance 3 (15 g, 48.6 mmol) and amine compound amine 16 (23.2 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 22.9 g of compound 16_P1. (Yield 69%, MS: [M+H] + =684).

[0302] Under a nitrogen atmosphere, the above compound 16_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.5 g, 526.4 mmol) was added to trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.7 g of compound 16. (Yield 56%, MS: [M+H] + =696).

[0303] Synthesis Example 17

[0304]

[0305] Under a nitrogen atmosphere, compound substance 3 (15 g, 48.6 mmol) and amine compound amine 17 (23.2 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 23.6 g of compound 17_P1. (Yield 71%, MS: [M+H] + =684).

[0306] Under a nitrogen atmosphere, the above compound 17_P1 (10 g, 14.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.5 g, 526.4 mmol) was added to trifluoromethanesulfonic anhydride (33 g, 117 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 17. (Yield 68%, MS: [M+H] + =698).

[0307] Synthesis Example 18

[0308]

[0309] Under a nitrogen atmosphere, compound substance 3 (15 g, 48.6 mmol) and amine compound amine 18 (24 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 23.1 g of compound 18_P1. (Yield 68%, MS: [M+H] + =700).

[0310] Under a nitrogen atmosphere, the above compound 18_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.3 g, 514.4 mmol) was added to trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 18. (yield 51%, MS: [M+H] + =713).

[0311] Synthesis example 19

[0312]

[0313] Under a nitrogen atmosphere, compound substance 3 (15 g, 48.6 mmol) and amine compound amine 19 (24 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 22.4 g of compound 19_P1. (Yield 66%, MS: [M+H] + =700).

[0314] Under a nitrogen atmosphere, the above compound 19_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.3 g, 514.4 mmol) was added to trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.4 g of compound 19. (yield 63%, MS: [M+H] + =715).

[0315] Synthesis example 20

[0316]

[0317] Under a nitrogen atmosphere, compound substance 3 (15 g, 48.6 mmol) and amine compound amine 20 (27.9 g, 51 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 20.1 g, 145.7 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 26 g of compound 20_P1. (Yield 69%, MS: [M+H] + =776).

[0318] Under a nitrogen atmosphere, the above compound 20_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.3 g, 463.9 mmol) was added to trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 20. (yield 70%, MS: [M+H] + =788).

[0319] Synthesis Example 21

[0320]

[0321] Under a nitrogen atmosphere, compound substance 4 (15 g, 46.2 mmol) and amine compound amine 21 (22.1 g, 48.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 19.1 g, 138.5 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 21_P1. (Yield 63%, MS: [M+H] + =700).

[0322] Under a nitrogen atmosphere, the above compound 21_P1 (10 g, 14.3 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.3 g, 514.4 mmol) was added to trifluoromethanesulfonic anhydride (32.2 g, 114.3 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.1 g of compound 21. (yield 50%, MS: [M+H] + =715).

[0323] Synthesis example 22

[0324]

[0325] Under a nitrogen atmosphere, compound substance 4 (15 g, 46.2 mmol) and amine compound amine 22 (25.8 g, 48.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 19.1 g, 138.5 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 21.5 g of compound 22_P1. (Yield 60%, MS: [M+H] + =776).

[0326] Under a nitrogen atmosphere, the above compound 22_P1 (10 g, 12.9 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.3 g, 463.9 mmol) was added to trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6 g of compound 22. (yield 59%, MS: [M+H] + =789).

[0327] Synthesis example 23

[0328]

[0329] Under a nitrogen atmosphere, compound substance 4 (15 g, 46.2 mmol) and amine compound amine 23 (22.9 g, 48.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 19.1 g, 138.5 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 24.1 g of compound 23_P1. (Yield 73%, MS: [M+H] + =716).

[0330] Under a nitrogen atmosphere, the above compound 23_P1 (10 g, 14 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.1 g, 502.8 mmol) was added to trifluoromethanesulfonic anhydride (31.5 g, 111.7 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.6 g of compound 23. (yield 55%, MS: [M+H] + =730).

[0331] Synthesis example 24

[0332]

[0333] Under a nitrogen atmosphere, compound substance 4 (15 g, 46.2 mmol) and amine compound amine 24 (22.9 g, 48.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 19.1 g, 138.5 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 22.1 g of compound 24_P1. (Yield 67%, MS: [M+H] + =716).

[0334] Under a nitrogen atmosphere, the above compound 24_P1 (10 g, 14 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (10.1 g, 502.8 mmol) was added to trifluoromethanesulfonic anhydride (31.5 g, 111.7 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.8 g of compound 24. (yield 57%, MS: [M+H] + =728).

[0335] Synthesis example 25

[0336]

[0337] Under a nitrogen atmosphere, compound substance 4 (15 g, 46.2 mmol) and amine compound amine 25 (26.5 g, 48.5 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (K2CO3, 19.1 g, 138.5 mmol) was dissolved in 100 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 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 29.2 g of compound 25_P1. (Yield 80%, MS: [M+H] + =792).

[0338] Under a nitrogen atmosphere, the above compound 25_P1 (10 g, 12.6 mmol) was added to 200 mL of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, heavy water (9.1 g, 454.5 mmol) was added to trifluoromethanesulfonic anhydride (28.5 g, 101 mmol) at 0°C and stirred for 5 hours to prepare a solution. Then, a mixed solution of trifluoromethanesulfonic anhydride and heavy water was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the mixture was heated to 140°C and stirred while maintaining the temperature. After reacting for 10 hours, the mixture was cooled to room temperature and the organic layer and the aqueous layer were separated. Then, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 25. (yield 51%, MS: [M+H] + =803).

[0339] Example 1

[0340] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0341] On the ITO transparent electrode prepared in this way, the following compound HI-1 was added as a hole injection layer. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a film with a thickness of Next, on the hole transport layer, the following compound EB-1 was vacuum-deposited to form a film with a thickness of Next, on the electron blocking layer, the following compound 1 and the following compound Dp-7 prepared above were vacuum-deposited at a weight ratio of 98:2 to form a film with a thickness of On the above-mentioned light-emitting layer, the following compound HB-1 was vacuum-deposited to form a film with a thickness of Next, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form a film with a thickness of On the electron injection and transport layer, lithium fluoride (LiF) is sequentially The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0342]

[0343] In the above process, the evaporation rate of organic matter is maintained to Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2*10 -7 Up to 5×10 -6 A support is provided to produce an organic light-emitting device.

[0344] Examples 2 to 25

[0345] In the organic light-emitting device of Example 1, an organic light-emitting device was manufactured by the same method as in Example 1, except that Compounds 2 to 25 described in Table 1 below were used as a host instead of Compound 1 when forming the light-emitting layer.

[0346]

[0347]

[0348]

[0349] Comparative Examples 1 to 8

[0350] In the organic light-emitting device of Example 1, when forming the light-emitting layer, the compounds described in Table 2 below were used instead of Compound 1 as the main body, and the organic light-emitting device was manufactured by the same method as in Example 1. Comparative compounds RH-1 to RH-6, comparative compound 1_P1, and compound 13_P1 used in Table 2 below are respectively shown below.

[0351]

[0352] [Experimental example]

[0353] The organic light-emitting devices manufactured in the above embodiments and comparative examples were subjected to a 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 50 mA / cm 2 The time required for the luminance to decrease to 95% relative to the initial luminance (T95, hr) was measured at a current density of 1.5 %. The results are shown in Tables 1 and 2 below.

[0354] [Table 1]

[0355]

[0356] [Table 2]

[0357]

[0358] When current was applied to the organic light-emitting devices prepared by Examples 1 to 25 and Comparative Examples 1 to 8, the results of Tables 1 and 2 were obtained. The red organic light-emitting device of Example 1 used a substance that was widely used in the past, and had a structure in which Compound 1 was used as a light-emitting layer and Dp-7 was used as a dopant for the red light-emitting layer. Examples 2 to 25 used Compounds 2 to 25 instead of Compound 1 to manufacture organic light-emitting devices, and Comparative Examples 1 to 19 used Comparative Compounds RH-1 to RH-6, Comparative Compound 1_P1, and Comparative Compound 13_P1 instead of Compound 1 to manufacture organic light-emitting devices.

[0359] From the results in Table 1, it can be confirmed that when the compound having the structure of Chemical Formula 1 is applied to the light-emitting layer of an organic electroluminescent device, a device having low voltage, high efficiency and long life characteristics can be obtained.

[0360] Specifically, the device of embodiments 1 to 25 in which the compound represented by chemical formula 1 according to the present invention, i.e., the specific position of the benzene ring at the end of one side of the benzodibenzofuran or benzodibenzothiophene mother core structure, i.e., the second carbon position behind the oxygen or sulfur atom in the terminal benzene ring fused with benzothiophene or benzofuran, is combined with a compound of a tertiary amine of a specific structure as the main material of the light-emitting layer, is compared with all the organic light-emitting devices of comparative examples 1 to 8 in which the above-mentioned comparative compounds RH-1 to RH-6, comparative compounds 1_P1, and comparative compounds 13_P1 are used as the main material of the light-emitting layer. The driving voltage is greatly reduced and the efficiency is also improved. From this point of view, it can be seen that the energy transfer from the main body to the red dopant is well formed. In addition, it can be seen that the organic light-emitting devices of embodiments 1 to 25 can greatly improve the life characteristics while maintaining high efficiency. It can be judged that this is ultimately due to the high stability of the compounds according to the embodiments of the present invention to electrons and holes compared with the compounds of the comparative examples. In summary, it can be confirmed that when the compound of the present invention is used as a light-emitting layer or a hole transport layer, the driving voltage, light-emitting efficiency and life characteristics of an organic light-emitting device can be improved.

[0361] In particular, it is found that the organic light-emitting device manufactured by using the compound according to the present invention as a host of the light-emitting layer shows more excellent performance in terms of efficiency and lifespan than the organic light-emitting device of the comparative example.

[0362] As described above, it was confirmed that the compound of the present invention exhibits superior characteristics in terms of efficiency and life, depending on the position of the substituent and the type of the substituent, compared with the comparative example compound.

[0363] [Explanation of symbols]

[0364] 1: Substrate 2: Anode

[0365] 3: Light-emitting layer 4: Cathode

[0366] 5: Hole injection layer 6: Hole transport layer

[0367] 7: Electron blocking layer 8: Hole blocking layer

[0368] 9: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Y is each independently O or S, R1 is each independently hydrogen or deuterium, L1, L2 and L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene, and Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 Heteroaryl, The prerequisite is that at least one of R1, L1 to L3, Ar1 and Ar2 is deuterium or is substituted with deuterium.

2. The compound according to claim 1, wherein At least one of R1 is deuterium.

3. The compound according to claim 1, wherein L1 and L2 are each independently a single bond, or a phenylene group substituted with hydrogen or deuterium.

4. The compound according to claim 1, wherein L3 is a phenylene group substituted with hydrogen or deuterium.

5. The compound according to claim 1, wherein At least one of L1, L2 and L3 is a phenylene group substituted with deuterium.

6. The compound according to claim 1, wherein Ar1 and Ar2 are each independently C substituted by hydrogen or deuterium 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl.

7. The compound according to claim 1, wherein At least one of Ar1 and Ar2 is C substituted with deuterium 6-19 Aryl, or C substituted by deuterium 2-19 Heteroaryl.

8. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl substituted by hydrogen or deuterium, biphenyl substituted by hydrogen or deuterium, naphthyl substituted by hydrogen or deuterium, phenanthryl substituted by hydrogen or deuterium, dibenzofuranyl substituted by hydrogen or deuterium, or dibenzothiophenyl substituted by hydrogen or deuterium.

9. The compound according to claim 1, wherein At least one of Ar1 and Ar2 is a biphenyl group substituted by hydrogen or deuterium, a naphthyl group substituted by hydrogen or deuterium, a phenanthryl group substituted by hydrogen or deuterium, or a dibenzofuranyl group substituted by hydrogen or deuterium.

10. The compound according to claim 1, wherein When L1 is a single bond, Ar1 is a C 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl, L1 is substituted or unsubstituted C 6-60 In the case of an arylene group, Ar1 is a C substituted by hydrogen or deuterium 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl, When L2 is a single bond, Ar2 is a C 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl, and L2 is substituted or unsubstituted C 6-60 In the case of an arylene group, Ar2 is a C substituted by hydrogen or deuterium. 6-19 Aryl, or C substituted by hydrogen or deuterium 2-19 Heteroaryl.

11. The compound according to claim 1, wherein The compound represented by the Chemical Formula 1 is substituted with 1 to 50 deuteriums.

12. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the following compounds: In the above formula, D is deuterium, a is the number of deuterium substitutions, and a>0.

13. An organic light emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 12.

14. The organic light emitting device according to claim 13, wherein: The organic layer containing the compound is a light-emitting layer.

15. The organic light emitting device according to claim 13, wherein: The compound is included as a host material of the light-emitting layer.

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