Compounds and organic light emitting devices comprising the same

Abstract

The present specification provides a compound of Chemical Formula 1 and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0183776, filed on December 24, 2020, and Korean Patent Application No. 10-2021-0078639, filed on June 17, 2021, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein in their entirety by reference.

[0002] The present specification relates to a compound and an organic light emitting device comprising the same. BACKGROUND

[0003] An organic light emitting phenomenon generally refers to a phenomenon that electric energy is converted into light energy using an organic material. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode, a cathode, and an organic material layer therebetween. In this context, the organic material layer is typically formed in a multi-layer structure formed of different materials to improve efficiency and stability of the organic light emitting device, for example, the organic material layer can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied between two electrodes in such an organic light emitting device structure, holes and electrons are injected from the anode and the cathode into the organic material layer, excitons are formed when the injected holes and electrons meet, and light is emitted when these excitons fall back to a ground state.

[0004] There is a continuing need to develop new materials for such an organic light emitting device. Among them, a blue light organic light emitting device is essentially required to have high color purity and long lifetime characteristics, however, a technique for simultaneously obtaining both of the characteristics is insufficient due to instability caused by high energy of a blue material. Recently, a thermally activated delayed fluorescence material having a core structure including boron was newly developed and attracted attention due to its high efficiency and color purity, however, the material has a disadvantage of short lifetime due to high triplet energy and low reverse intersystem crossing rate. Therefore, there is a need to develop a blue organic light emitting material which simultaneously realizes high color purity and long lifetime characteristics. SUMMARY

[0005] TECHNICAL PROBLEM

[0006] The present specification aims to provide a compound and an organic light emitting device comprising the same.

[0007] TECHNICAL SOLUTION

[0008] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] A1 is any one of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted heterocyclic ring, and a fused ring thereof,

[0013] R5 to R8 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded to an adjacent group to form a substituted or unsubstituted ring,

[0014] Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded to A1 to form any one of a substituted or unsubstituted aromatic heterocyclic ring, an aliphatic heterocyclic ring, and a fused ring thereof, which contains any one or more of N, S, O, and Si.

[0015] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded to R5 to form any one of a substituted or unsubstituted aromatic heterocyclic ring, an aliphatic heterocyclic ring, and a fused ring thereof, which contains any one or more of N, S, O, and Si.

[0016] When Ar2 and R5 form a benzo oxazine ring, the benzo oxazine ring is an unsubstituted benzo oxazine ring.

[0017] At least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded to an adjacent group to form a substituted or unsubstituted ring, and the rest is hydrogen, and

[0018] Ar1is phenyl, A1is substituted or unsubstituted phenyl, R6to R8are hydrogen, adjacent groups among Z1to Z3are not bonded to each other to form a substituted or unsubstituted ring, and at the same time, Ar2and R5form an indolyl group, the indolyl group is a substituted indolyl group.

[0019] Another embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound.

[0020] Advantages

[0021] The compound according to one embodiment of the present specification can be used as a material of an organic material layer of an organic light-emitting device, and by using the compound, high color purity, high efficiency, and / or improved lifespan characteristics are obtained in an organic light-emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0022] Figure 1 and Figure 2 Each illustrates an organic light-emitting device according to one embodiment of the present specification.

[0023] Figure 3 is a graph showing a molecular model obtained by simulating the dopant B and BH system of Example 2-1 of the present specification.

[0024] Figure 4 is a graph showing a molecular model obtained by simulating the BD1 and BH system of Comparative Example 2-1 of the present specification.

[0025] Figure 5 is a graph showing a molecular model obtained by simulating the BD2 and BH system of Comparative Example 2-2 of the present specification.

[0026] Figure 6 is a graph showing the orbital distribution of the HOMO and LUMO of BD1.

[0027] [REFERENCE NUMERALS]

[0028] 1: Substrate

[0029] 2: First electrode

[0030] 3: Emission layer

[0031] 4: Second electrode

[0032] 5: First hole injection layer

[0033] 6: Second hole injection layer

[0034] 7: Hole transport layer

[0035] 8: electron blocking layer

[0036] 9: first electron transport layer

[0037] 10: second electron transport layer

[0038] 11: electron injection layer DETAILED DESCRIPTION

[0039] Hereinafter, the present specification will be described in more detail.

[0040] One embodiment of the present specification relates to a compound represented by Chemical Formula 1.

[0041] The existing organic light emitting device using a boron-based compound has high efficiency compared to an organic light emitting device using a pyrene-based compound, but has the disadvantage of short lifespan. However, the compound represented by Chemical Formula 1 has a narrow full width at half maximum, and the organic light emitting device including the same has the advantages of improved efficiency and lifespan. The narrow full width at half maximum is maintained due to the hexagonal ring of boron and amine, and the stability of the core in an unstable polaron state is increased by filling the deficient electrons of boron through direct bonding on the opposite side of boron and amine, thereby increasing the lifespan, and the organic light emitting device including the same has improved efficiency by promoting the transition of a polaron to an exciton state.

[0042] Throughout the specification, the term "combination thereof" included in the Markush expression means a mixture or combination of one or more selected from the constituent elements described in the Markush expression, and means to include one or more selected from the constituent elements.

[0043] Examples of the substituents in the present specification are described below, however, the substituents are not limited thereto.

[0044] In the present specification, means a connection site.

[0045] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0046] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, or substituted with two or more substituents connected to each other from among the above exemplified substituents, or not having a substituent.

[0047] In the present specification, two or more substituents connected to each other mean that a hydrogen of any substituent is connected to another substituent. For example, two or more substituents connected to each other can include phenyl and naphthyl connected to each other to be a substituent Further, three substituents connected to each other not only include (substituent 1) - (substituent 2) - (substituent 3) connected continuously, but also include (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be connected to each other to be a substituent When four or more substituents are connected to each other, the same definition described above is also applicable.

[0048] In the present specification, examples of the halogen group can include fluorine, chlorine, bromine, or iodine.

[0049] In the present specification, the alkyl group can be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof can include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, iso-hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0050] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms. Specific examples thereof can include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, norbornyl, and the like, but are not limited thereto.

[0051] In this specification, the alkoxy group can be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0052] In this specification, the alkenyl group can be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0053] In this specification, alkyl haloide means that, in the definition of alkyl, the hydrogen of the alkyl group is substituted with at least one halogen group.

[0054] In this specification, haloalkoxy means, in the definition of alkoxy, that the hydrogen of the alkoxy group is substituted with at least one halogen group.

[0055] In this specification, there are no particular limitations on the aryl group, but it is preferred to have 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0056] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of monocyclic aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, etc.

[0057] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of polycyclic aryl groups may include naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, finadeninyl, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0058] In this specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0059] When the fluorene group is substituted, it can include However, the structure is not limited to this.

[0060] In the present specification, "adjacent" groups can mean a substituent that substitutes an atom directly connected to an atom substituted by a corresponding substituent, a substituent located spatially closest to a corresponding substituent, or another substituent that substitutes an atom substituted by a corresponding substituent. For example, two substituents that substitute the ortho positions in a benzene ring and two substituents that substitute the same carbon in an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0061] In the present specification, arylalkyl means an alkyl group substituted with an aryl group, and the examples of the above-mentioned aryl and alkyl groups can be applied to the aryl and alkyl groups in the arylalkyl group.

[0062] In the present specification, aryloxy means that the alkyl group of the alkoxy group is replaced with an aryl group in the definition of the alkoxy group, and examples of the aryloxy group can include phenoxy, p-methoxyphenoxy, m-methoxyphenoxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-t-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, and the like, but are not limited thereto.

[0063] In the present specification, the alkyl group in the alkylthio group is the same as the examples of the above-mentioned alkyl group. Specific examples of the alkylthio group can include methylthio, ethylthio, t-butylthio, hexylthio, octylthio, and the like, but are not limited thereto.

[0064] In the present specification, the aryl group in the arylthio group is the same as the examples of the above-mentioned aryl group. Specific examples of the arylthio group can include phenylthio, 2-methylphenylthio, 4-t-butylphenylthio, and the like, but are not limited thereto.

[0065] In the present specification, a heterocyclic group is a group including one or more atoms other than carbon (i.e., a hetero atom), and specifically, the hetero atom can include one or more atoms selected from O, N, Se, S, and the like, and the heterocyclic group includes an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group can be represented as a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30, and the heterocyclic group can be monocyclic or polycyclic. Examples of the heterocyclic group can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phtalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benz azinyl, phenothiazinyl, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzazepinyl, dihydroindolocarbazolyl, spirofluore xanthenyl, spirofluore xanthyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl, tetrahydrobenzofuranyl, and the like, but are not limited thereto. azinyl, phenothiazinyl, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzazepinyl, dihydroindolocarbazolyl, spirofluore xanthenyl, spirofluore xanthyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl, tetrahydrobenzofuranyl, and the like, but are not limited thereto. azinyl, phenothiazinyl, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzazepinyl, dihydroindolocarbazolyl, spirofluore xanthenyl, spirofluore xanthyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl, tetrahydrobenzofuranyl, and the like, but are not limited thereto. azinyl, phenothiazinyl, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzazepinyl, dihydroindolocarbazolyl, spirofluore xanthenyl, spirofluore xanthyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl, tetrahydrobenzofuranyl, and the like, but are not limited thereto.

[0066] In the present specification, a silyl group can be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, and the like. As the alkyl group in the alkylsilyl group, the examples of the alkyl group described above can be applied, as the aryl group in the arylsilyl group, the examples of the aryl group described above can be applied, as the alkyl group and the aryl group in the alkylarylsilyl group, the examples of the alkyl group and the aryl group can be applied, and as the heteroaryl group in the heteroarylsilyl group, the examples of the heterocyclic group can be applied.

[0067] In the present specification, a boron group can be -BR 100 R 101 . R 100 and R 101 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; a halogen; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Specific examples of the boron group can include a dimethylboron group, a diethylboron group, a tert-butylmethylboron group, a diphenylboron group, and the like, but are not limited thereto.

[0068] In the present specification, an amine group can be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of the amine group can include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a diphenylamine group, an anthrylamine group, a 9-methyl-anthrylamine group, a diphenylamine group, a dimethylphenylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenyldiphenylamine group, an N-phenylnaphthylamine group, an N-diphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrylamine group, an N-diphenylphenanthrylamine group, an N-phenylfluorenylamine group, an N-phenyltrisbiphenylamine group, an N-phenanthrylfluorenylamine group, an N-diphenylfluorenylamine group, and the like, but are not limited thereto.

[0069] In the present specification, an N-alkylarylamine group means an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the above-mentioned alkyl group and aryl group.

[0070] In the present specification, an N-arylheteroarylamine group means an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-mentioned aryl group and heteroaryl group.

[0071] In the present specification, an N-alkylheteroarylamine group means an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-mentioned alkyl group and heteroaryl group.

[0072] In the present specification, examples of an alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group can be a linear or branched alkyl group. The alkylamine group including two or more alkyl groups can include a linear alkyl group, a branched alkyl group, or both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the alkylamine group can be selected from the examples of the above-mentioned alkyl group.

[0073] In the present specification, examples of a heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups can include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heteroaryl group.

[0074] In the present specification, a hydrocarbon ring group can be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from the examples of a cycloalkyl group, an aryl group, and a combination thereof. Examples of the hydrocarbon ring group can include a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthyl group, a tetrahydroanthryl group, a 1,2,3,4-tetrahydro-1,4-methanonnaphthyl group, a 1,2,3,4-tetrahydro-1,4-ethanonnaphthyl group, and the like, but are not limited thereto.

[0075] In the present specification, the meaning of "adjacent" in "bonded to an adjacent group to form a ring" is the same as the description provided above, and the "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0076] In the present specification, a hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, except that the hydrocarbon ring is not monovalent. Examples of the hydrocarbon ring can include benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methano naphthalene, 1,2,3,4-tetrahydro-1,4-ethano naphthalene, and the like, but are not limited thereto.

[0077] Further, an aliphatic hydrocarbon ring includes all of a hydrocarbon ring containing a single bond, a non-aromatic hydrocarbon ring containing a multiple bond, or a ring having a form in which a ring containing a single bond and a multiple bond is fused. Thus, a ring of the aliphatic hydrocarbon ring formed of a single bond can be selected from examples of a cycloalkyl group, except that the aliphatic hydrocarbon ring is not a monovalent group, and a hydrocarbon ring containing a single bond and a double bond but not an aromatic ring, such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, or norbornene, also belongs to the aliphatic hydrocarbon ring.

[0078] In the present specification, a heterocycle means a ring containing one or more non-carbon atoms (i.e., a heteroatom), and specifically, the heteroatom can include one or more atoms selected from O, N, Se, S, and the like. The heterocycle can be a single ring or a multiple ring, and can be an aromatic heterocycle; an aliphatic heterocycle; a fused ring of an aromatic heterocycle and an aliphatic heterocycle; a fused ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocycle, or a fused ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocycle, and the aromatic heterocycle can be selected from examples of a heteroaryl group of a heterocyclic group, except that the aromatic heterocycle is not monovalent.

[0079] In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. The aliphatic heterocycle includes all of an aliphatic ring containing a single bond, an aliphatic ring containing a multiple bond, or an aliphatic ring having a form in which a ring containing a single bond and a multiple bond is fused. Examples of the aliphatic heterocycle can include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azokane, thiokane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, tetrahydrobenzofuran, and the like, but are not limited thereto. The aliphatic heterocycle includes all of an aliphatic ring containing a single bond, an aliphatic ring containing a multiple bond, or an aliphatic ring having a form in which a ring containing a single bond and a multiple bond is fused. Examples of the aliphatic heterocycle can include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azokane, thiokane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, tetrahydrobenzofuran, and the like, but are not limited thereto.

[0080] Unless otherwise defined in this specification, all technical and scientific terms used in this specification have the same meaning as is commonly understood by one of ordinary skill in the art. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the embodiments of the present disclosure, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are herein incorporated by reference in their entirety, and to the extent that they conflict with the specification, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0081] According to one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0082] [Chemical Formula 1-1]

[0083]

[0084] In Chemical Formula 1-1,

[0085] R5 to R8, Ar2, and Z1 to Z3 have the same definition as in Chemical Formula 1,

[0086] R1 to R4 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or is bonded to an adjacent group to form any one of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted heterocycle, and a fused ring thereof,

[0087] Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or is bonded to R4 to form any one of a substituted or unsubstituted and containing any one or more of N, S, O, and Si aromatic heterocycle, aliphatic heterocycle, and a fused ring thereof, and

[0088] When Ar1 is a phenyl group, R1 to R4 and R6 to R8 are hydrogen, adjacent groups among Z1 to Z3 are not bonded to each other to form a substituted or unsubstituted ring, and at the same time, Ar2 and R5 form an indole group, the indole group is a substituted indole group.

[0089] According to one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-2.

[0090] [Chemical Formula 1-2]

[0091]

[0092] In Chemical Formula 1-2,

[0093] R5 to R8, Ar2, and Z1 to Z3 have the same definition as in Chemical Formula 1,

[0094] X1 is CRR', O, or S,

[0095] A11 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

[0096] Ar'1 is a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted aryl; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring, and

[0097] R and R' are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl; a substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic ring, or are bonded to each other to form a substituted or unsubstituted ring.

[0098] According to one embodiment of the present specification, Chemical Formula 1-1 is represented by any one of the following Chemical Formulae 1-1-1 to 1-1-36.

[0099] [Chemical Formula 1-1-1]

[0100]

[0101] [Chemical Formula 1-1-2]

[0102]

[0103] [Chemical Formula 1-1-3]

[0104]

[0105] [Chemical Formula 1-1-4]

[0106]

[0107] [Chemical Formula 1-1-5]

[0108]

[0109] [Chemical Formula 1-1-6]

[0110]

[0111] [Chemical Formula 1-1-7]

[0112]

[0113] [Chemical Formula 1-1-8]

[0114]

[0115] [Chemical Formula 1-1-9]

[0116]

[0117] [Chemical Formula 1-1-10]

[0118]

[0119] [Chemical Formula 1-1-11]

[0120]

[0121] [Chemical Formula 1-1-12]

[0122]

[0123] [Chemical Formula 1-1-13]

[0124]

[0125] [Chemical Formula 1-1-14]

[0126]

[0127] [Chemical Formula 1-1-15]

[0128]

[0129] [Chemical Formula 1-1-16]

[0130]

[0131] [Chemical Formula 1-1-17]

[0132]

[0133] [Chemical Formula 1-1-18]

[0134]

[0135] [Chemical Formula 1-1-19]

[0136]

[0137] [Chemical Formula 1-1-20]

[0138]

[0139] [Chemical Formula 1-1-21]

[0140]

[0141] [Chemical Formula 1-1-22]

[0142]

[0143] [Chemical Formula 1-1-23]

[0144]

[0145] [Chemical Formula 1-1-24]

[0146]

[0147] [Chemical Formula 1-1-25]

[0148]

[0149] [Chemical Formula 1-1-26]

[0150]

[0151] [Chemical Formula 1-1-27]

[0152]

[0153] [Chemical Formula 1-1-28]

[0154]

[0155] [Chemical Formula 1-1-29]

[0156]

[0157] [Chemical Formula 1-1-30]

[0158]

[0159] [Chemical Formula 1-1-31]

[0160]

[0161] [Chemical Formula 1-1-32]

[0162]

[0163] [Chemical Formula 1-1-33]

[0164]

[0165] [Chemical Formula 1-1-34]

[0166]

[0167] [Chemical Formula 1-1-35]

[0168]

[0169] [Chemical Formula 1-1-36]

[0170]

[0171] In Chemical Formulas 1-1-1 to 1-1-36,

[0172] X2to X9are the same as or different from each other, and each is independently CRR', NR", O, or S,

[0173] Y1and Y2are the same as or different from each other, and each is independently CG1G2, SiG8G9, NG101, O, or S,

[0174] y1is 0 or 1, and when y1is 0, Y1is a direct bond,

[0175] y2is 0 or 1, and when y2is 0, Y2is a direct bond,

[0176] R, R', and R" are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are bonded to each other to form a substituted or unsubstituted ring,

[0177] R'1to R'8are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group,

[0178] G1to G19, G'13, and G101are the same as or different from each other and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

[0179] g3, g7, and g15 to g18 are each an integer of 1 to 4,

[0180] g4and g10are each an integer of 1 to 8,

[0181] g13and g14are each 1 or 2,

[0182] g'13is an integer of 0 to 2,

[0183] g19is an integer of 1 to 3,

[0184] a21is 0 or 1,

[0185] when g3, g4, g7, g10, and g15 to g19 are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

[0186] when g13, g'13, and g14are each 2, the substituents in the two parentheses are the same as or different from each other,

[0187] Ar'1and Ar'2are the same as or different from each other and each is independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group,

[0188] A2and A21are the same as or different from each other and each is independently a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

[0189] at least one of Z1to Z3is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded to an adjacent group to form a substituted or unsubstituted ring, and the rest is hydrogen, and

[0190] in Chemical Formulae 1-1-4, 1-1-6, 1-1-8, 1-1-12, 1-1-28, and 1-1-32,

[0191] when y2 is 1 and Y2 is O, G7 and R'6 to R'8 are hydrogen.

[0192] According to one embodiment of the present specification, Chemical Formula 1-2 is represented by any one of the following Chemical Formulae 1-2-1 to 1-2-6.

[0193] [Chemical Formula 1-2-1]

[0194]

[0195] [Chemical Formula 1-2-2]

[0196]

[0197] [Chemical Formula 1-2-3]

[0198]

[0199] [Chemical Formula 1-2-4]

[0200]

[0201] [Chemical Formula 1-2-5]

[0202]

[0203] [Chemical Formula 1-2-6]

[0204]

[0205] in Chemical Formulae 1-2-1 to 1-2-6,

[0206] X1, A11, and Z1to Z3have the same definition as in Chemical Formula 1-2,

[0207] X3to X6are the same as or different from each other, and are each independently CRR', NR", O, or S,

[0208] Y2is CG1G2, SiG8G9, NG101, O, or S,

[0209] y2is 0 or 1, and when y2is 0, Y2is a direct bond,

[0210] A2is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

[0211] Ar'1is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group,

[0212] R, R', and R" are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic ring group, or are bonded to each other to form a substituted or unsubstituted ring,

[0213] R'5to R'8are the same or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group,

[0214] G1, G2, G7 to G12, G14, G15, G16, and G101are the same or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

[0215] g7, g15, and g16are each an integer of 1 to 4,

[0216] g10is an integer of 1 to 8,

[0217] g14is 1 or 2,

[0218] when each of g7, g10, g15, and g16 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

[0219] when g14 is 2, the substituents in the two parentheses are the same as or different from each other, and

[0220] Ar'1and Ar'2are the same as or different from each other, and each is independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0221] According to one embodiment of the present specification, in Chemical Formula 1-1-4,

[0222] Y2is CG1G2, SiG8G9, NG101, O, or S, and y2is 0 or 1,

[0223] when y2is 0, Y2is a direct bond,

[0224] R'1to R'4and R'6to R'8are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group,

[0225] G7are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, and g7is an integer of 1 to 4,

[0226] Ar'1is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group,

[0227] at least one of Z1to Z3is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, and

[0228] in Chemical Formula 1-2-2,

[0229] when y2 is 1 and Y2 is O, G7 and R'6 to R'8 are hydrogen.

[0230] According to one embodiment of the present specification, in Chemical Formula 1-1-4, a case where substituents are bonded to each other to form a substituted or unsubstituted ring is not included.

[0231] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3 to 1-5.

[0232] [Chemical Formula 1-3]

[0233]

[0234] [Chemical Formula 1-4]

[0235]

[0236] [Chemical Formula 1-5]

[0237]

[0238] in Chemical Formulas 1-3 to 1-5,

[0239] Ar1, Ar2, A1, R5 to R8, and Z1to Z3have the same definition as in Chemical Formula 1,

[0240] T1to T10are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or are bonded to adjacent groups to form a substituted or unsubstituted ring,

[0241] at least one of T1and T2is a substituted or unsubstituted alkyl; a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted aryl; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, and

[0242] at least one of T6and T7is a substituted or unsubstituted alkyl; a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted aryl; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group.

[0243] According to one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2.

[0244] [Chemical Formula 2]

[0245]

[0246] In Chemical Formula 2,

[0247] A1, Ar1, and Z1to Z3have the same definition as in Chemical Formula 1,

[0248] Ar2is a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted aryl; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded with R"51to form any one of a substituted or unsubstituted aromatic heterocyclic ring, an aliphatic heterocyclic ring, and a fused ring thereof, which includes any one or more of N, S, O, and Si,

[0249] R"51and R"5to R"8are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl; a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted alkoxy; a substituted or unsubstituted arylalkyl; a substituted or unsubstituted aryloxy; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring group, or is bonded with an adjacent group to form a substituted or unsubstituted ring,

[0250] r"51is 1 or 2, and

[0251] When r"51is 2, two R"51are the same as or different from each other.

[0252] According to one embodiment of the present specification, Chemical Formula 1-1 is represented by the following Chemical Formula 2-1.

[0253] [Chemical Formula 2-1]

[0254]

[0255] In Chemical Formula 2-1,

[0256] Ar1, R1 to R4, and Z1 to Z3 have the same definition as in Chemical Formula 1-1,

[0257] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or is bonded to R"51 to form any one of substituted or unsubstituted aromatic heterocycles, aliphatic heterocycles, and fused rings thereof, which contain any one or more of N, S, O, and Si,

[0258] R"51 and R"5 to R"8 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or is bonded to an adjacent group to form a substituted or unsubstituted ring,

[0259] r"51 is 1 or 2, and

[0260] When r"51 is 2, the two R"51 are the same as or different from each other.

[0261] According to one embodiment of the present specification, Chemical Formula 1-2 is represented by the following Chemical Formula 2-2.

[0262] [Chemical Formula 2-2]

[0263]

[0264] X1, A11, Ar'1, and Z1 to Z3 have the same definition as in Chemical Formula 1-2,

[0265] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or is bonded to R"51 to form any one of substituted or unsubstituted aromatic heterocycles, aliphatic heterocycles, and fused rings thereof, which contain any one or more of N, S, O, and Si,

[0266] R"51and R"5to R"8are the same as or different from each other and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic ring group, or bonded to an adjacent group to form a substituted or unsubstituted ring,

[0267] r"51is 1 or 2, and

[0268] When r"51is 2, the two R"51are the same as or different from each other.

[0269] According to one embodiment of the present specification, adjacent groups among Z1to Z3are bonded to each other to form a ring represented by Chemical Formula C-1 or C-2.

[0270] [Chemical Formula C-1]

[0271]

[0272] [Chemical Formula C-2]

[0273]

[0274] In Chemical Formula C-1 and C-2,

[0275] J1is O, S, NQ7, CQ8Q9, or SiQ10Q11,

[0276] W1to W8and Q7to Q11are the same as or different from each other and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic ring group, or bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0277] * is a site bonded to Chemical Formula 1.

[0278] According to one embodiment of the present specification, adjacent groups among W1to W8are bonded to each other to form a ring represented by Chemical Formula C-1.

[0279] According to one embodiment of the present specification, Chemical Formula C-2 is selected from any one of the following structures.

[0280]

[0281] In the structure,

[0282] W1to W4, W5to W8, and Q7to Q11have the same definition as described above.

[0283] According to one embodiment of the present specification, A1is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[0284] According to one embodiment of the present specification, A1is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[0285] According to one embodiment of the present specification, A1is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or NQ1Q2-substituted benzene; naphthalene; indene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; fluorene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthalene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzonaphthofuran; naphthofuran; benzonaphthothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzonaphthofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzonaphthothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzofluorene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or tetrahydrobenzindene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0286] According to one embodiment of the present specification, A1is phenyl unsubstituted or substituted with methyl, tert-butyl, tetramethyltetrahydronaphthyl, phenyl, or NQ1Q2; naphthalene; indene unsubstituted or substituted with methyl; fluorene unsubstituted or substituted with methyl; tetrahydronaphthalene unsubstituted or substituted with methyl; dibenzofuran unsubstituted or substituted with methyl or tert-butyl; dibenzothiophene unsubstituted or substituted with methyl or tert-butyl; benzofuran unsubstituted or substituted with methyl, phenyl, or tert-butyl; benzothiophene unsubstituted or substituted with methyl, phenyl, or tert-butyl; benzonaphthofuran; naphthofuran; benzonaphthothiophene unsubstituted or substituted with tert-butyl; tetrahydrobenzonaphthofuran unsubstituted or substituted with methyl; tetrahydrobenzonaphthothiophene unsubstituted or substituted with methyl; tetrahydrobenzofluorene unsubstituted or substituted with methyl; tetrahydronaphthofuran unsubstituted or substituted with methyl; tetrahydronaphthothiophene unsubstituted or substituted with methyl; naphthothiophene unsubstituted or substituted with methyl; or tetrahydrobenzoindene unsubstituted or substituted with methyl.

[0287] According to one embodiment of the present specification, Q1and Q2are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0288] According to one embodiment of the present specification, Q1and Q2are the same as or different from each other, and each independently a methyl group; a tert-butyl group; a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; a biphenyl group unsubstituted or substituted with a methyl group; a fluorenyl group unsubstituted or substituted with a methyl group; a tetrahydronaphthyl group unsubstituted or substituted with a methyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0289] According to one embodiment of the present specification, R5to R8are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[0290] According to one embodiment of the present specification, R5to R8are the same as or different from each other, and are each independently hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or are bonded to adjacent groups to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0291] According to one embodiment of the present specification, R5to R8are the same as or different from each other, and are each independently hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or are bonded to adjacent groups to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. ​benzo-oxathiine; benzodithiine; thioxanthene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; chromene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; or dihydronaphthalene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms.

[0292] According to one embodiment of the present specification, R5to R8are identical to or different from each other and are each independently hydrogen; deuterium; methyl; tert-butyl; phenyl; or NQ3Q4, or are bonded with an adjacent group to form cyclohexane unsubstituted or substituted with methyl; benzene; benzofuran unsubstituted or substituted with methyl, tert-butyl, or diphenylamine unsubstituted or substituted with tert-butyl; benzothiophene unsubstituted or substituted with methyl, tert-butyl, or diphenylamine unsubstituted or substituted with tert-butyl; naphthofuran; naphthothiophene; indene unsubstituted or substituted with methyl, or diphenylamine unsubstituted or substituted with tert-butyl; indole unsubstituted or substituted with phenyl; indoloindole unsubstituted or substituted with methyl; tetrahydronaphthofuran unsubstituted or substituted with methyl; tetrahydronaphthothiophene unsubstituted or substituted with methyl; tetrahydrobenzoindene unsubstituted or substituted with methyl; benzodioxole unsubstituted or substituted with methyl; benzodioxane unsubstituted or substituted with methyl; benzodioxepane unsubstituted or substituted with methyl; benzodithiophene unsubstituted or substituted with methyl; benzodioxole unsubstituted or substituted with methyl; benzodioxane unsubstituted or substituted with methyl; benzodioxepane unsubstituted or substituted with methyl; benzodithiophene unsubstituted or substituted with methyl; thioxanthene unsubstituted or substituted with methyl; chromene unsubstituted or substituted with methyl; or dihydronaphthalene unsubstituted or substituted with methyl. benzo-oxathiine; benzodithiine; thioxanthene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; chromene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; or dihydronaphthalene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms. benzo-oxathiine; benzodithiine; thioxanthene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; chromene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; or dihydronaphthalene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms.

[0293] According to one embodiment of the present specification, Q3and Q4are identical to or different from each other and are each independently monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; fused ring group of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; or monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0294] According to one embodiment of the present specification, Q3and Q4are identical to or different from each other and are each independently methyl; tert-butyl; phenyl unsubstituted or substituted with methyl or tert-butyl; biphenyl unsubstituted or substituted with methyl or tert-butyl; fluorenyl unsubstituted or substituted with methyl; tetrahydronaphthyl unsubstituted or substituted with methyl; diphenofuranyl; or diphenothiophenyl.

[0295] According to one embodiment of the present description, Ar1is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to A1to form any of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a fused ring thereof, including any one or more of N, S, O, and Si.

[0296] According to one embodiment of the present description, Ar1is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with any one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to A1to form any of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a fused ring thereof, including any one or more of N, S, O, and Si.

[0297] According to one embodiment of the present specification, Ar1is phenyl unsubstituted or substituted with any one or more selected from the group consisting of linear or branched alkyl having 1 to 30 carbon atoms, monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and combinations thereof; biphenyl unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; terphenyl; fluorenyl unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; tetrahydronaphthyl unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; dibenzofuranyl; or dibenzothiophenyl, or bonded with A1to form dihydroacridine unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms or monocyclic or polycyclic aryl having 6 to 30 carbon atoms; spiroacridine fluorene; hexahydrocarbazole unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; dihydrobenzacridine unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms or monocyclic or polycyclic aryl having 6 to 30 carbon atoms; hexahydrobenzacridine unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms or monocyclic or polycyclic aryl having 6 to 30 carbon atoms; spirobenzacridine; spiro-tetrahydrobenzacridine fluorene; benzofuroindole; benzothiophenoindole; dihydrodibenzazasilole unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms or monocyclic or polycyclic aryl having 6 to 30 carbon atoms; spiro-dibenzosilole dibenzazasilole; phenoxazine; phenothiazine; dihydroindenoinode unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms or monocyclic or polycyclic aryl having 6 to 30 carbon atoms; benzocarbazole; or carbazole unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, or monocyclic or polycyclic aryl having 6 to 30 carbon atoms.

[0298] According to one embodiment of the present specification, Ar1is phenyl unsubstituted or substituted with any one or more selected from the group consisting of methyl, isopropyl, tert-butyl, phenyl, and combinations thereof; biphenyl unsubstituted or substituted with methyl or tert-butyl; terphenyl; fluorenyl unsubstituted or substituted with methyl; tetrahydronaphthyl unsubstituted or substituted with methyl; dibenzofuranyl; or dibenzothiophenyl, or bonded with A1to form dihydroacridine unsubstituted or substituted with methyl or phenyl; spiroacridine fluorene; hexahydrocarbazole unsubstituted or substituted with any one or more selected from the group consisting of methyl and tert-butyl; dihydrobenzacridine unsubstituted or substituted with methyl or phenyl; hexahydrobenzacridine unsubstituted or substituted with methyl or phenyl; spirobenzacridine; spiro-tetrahydrobenzacridine fluorene; benzofuroindole; benzothiophenoindole; dihydrodibenzazasilole unsubstituted or substituted with methyl or phenyl; spiro-dibenzosilole dibenzazasilole; phenoxazine; phenothiazine; dihydroindenoinode unsubstituted or substituted with methyl or phenyl; benzocarbazole; or carbazole unsubstituted or substituted with methyl or phenyl. ​pyridine; pyrimidine; pyrazine; pyridazine; triazine; triazole; tetrazole; oxadiazole; thiadiazole; oxatriazole; thiatriazole; furan; thiophene; selenophene; oxazole; thiazole; oxathiazole; imidazole; pyrazole; indole; benzofuran; benzothiophene; benzoxazole; benzothiazole; benzimidazole; indazole; quinoline; isoquinoline; quinazoline; quinoxaline; quinolizine; purine; pteridine; carbazole; or indolizine.

[0299] According to one embodiment of the present U.S. Patent Application, Ar2is a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, or bonded to R5to form any of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and fused rings thereof, and containing any one or more of N, S, O, and Si.

[0300] According to one embodiment of the present U.S. Patent Application, Ar2is a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, or bonded to R5to form any of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and fused rings thereof, and containing any one or more of N, S, O, and Si.

[0301] According to one embodiment of this specification, Ar2 is an unsubstituted phenyl group or substituted with any or more of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combinations thereof; an unsubstituted biphenyl group or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a terphenyl group; an unsubstituted fluorenyl group or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl group or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a dibenzofuranyl group; or a dibenzothiophenyl group, or bonded to R5 to form an unsubstituted or substituted linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Substituted dihydroquinoline; spiroquinoline fluorene; unsubstituted or substituted hexahydroindene with a linear or branched alkyl group having 1 to 30 carbon atoms; unsubstituted or substituted dihydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; unsubstituted hexahydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophenopyrrole; unsubstituted or substituted dihydrobenzozasilane with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirodibenzothiophenobenzozasilane; benzo[…] Azides; benzothiazides; dihydroindopyrroles that are unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzoindole; or indoles that are unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0302] According to one embodiment of this specification, Ar2 is an unsubstituted or substituted phenyl group selected from any or more of methyl, isopropyl, tert-butyl, phenyl, and combinations thereof; an unsubstituted or substituted biphenyl group; a terphenyl group; an unsubstituted or substituted fluorenyl group; an unsubstituted or substituted tetrahydronaphthyl group; a dibenzofuranyl group; or a dibenzothiophene group, or bonded to R5 to form an unsubstituted or substituted dihydroquinoline group; a spirobenzoquinoline group; an unsubstituted or substituted hexahydroindene group selected from any or more of methyl and tert-butyl groups; an unsubstituted or substituted dihydrobenzoquinoline group; an unsubstituted or substituted hexahydrobenzoquinoline group; a spirobenzoquinoline group; a spirotetrahydrobenzoquinoline fluorene group; a benzofuranopyrrole group; a benzothiophene group; an unsubstituted or substituted dihydrobenzoazasilane group; a spirobenzothiophene dibenzoazasilane group; a benzo[…] oxazepine; benzothiazepine; indolizine unsubstituted or substituted with methyl or phenyl; benzindole; or indole unsubstituted or substituted with tert-butyl, adamantyl, or phenyl.

[0303] According to one embodiment of the present specification, at least one of Z1to Z3is a linear or branched alkyl having 1 to 30 carbon atoms, unsubstituted or substituted; a monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, unsubstituted or substituted; a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, unsubstituted or substituted; or NQ5Q6, or forms a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, unsubstituted or substituted; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, unsubstituted or substituted, and the rest is hydrogen.

[0304] According to one embodiment of the present specification, at least one of Z1to Z3is deuterium; a linear or branched alkyl having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, unsubstituted or substituted with deuterium, or a linear or branched alkyl having 1 to 30 carbon atoms; or NQ5Q6, or bonded to adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, unsubstituted or substituted with a linear or branched alkyl having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of a linear or branched alkyl having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and combinations thereof, and the rest is hydrogen.

[0305] According to one embodiment of the present specification, at least one of Z1to Z3is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; phenyl unsubstituted or substituted with deuterium, or a linear or branched alkyl having 1 to 30 carbon atoms; or NQ5Q6, or bonded to adjacent groups to form benzene; indene unsubstituted or substituted with a linear or branched alkyl having 1 to 30 carbon atoms; benzofuran unsubstituted or substituted with a linear or branched alkyl having 1 to 30 carbon atoms; naphthofuran; tetrahydronaphthofuran unsubstituted or substituted with a linear or branched alkyl having 1 to 30 carbon atoms; benzothiophene; or indole unsubstituted or substituted with one or more substituents selected from the group consisting of a linear or branched alkyl having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and combinations thereof, and the rest is hydrogen.

[0306] According to one embodiment of the present specification, at least one of Z1to Z3is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; phenyl unsubstituted or substituted with deuterium or methyl; or NQ5Q6, or bonded with adjacent groups to form benzene; indene unsubstituted or substituted with methyl; benzofuran unsubstituted or substituted with tert-butyl; naphthofuran; tetrahydronaphthofuran unsubstituted or substituted with methyl; benzothiophene; or indole unsubstituted or substituted with phenyl, or tetrahydronaphthyl substituted with methyl, and the rest is hydrogen.

[0307] According to one embodiment of the present specification, Z2is deuterium; substituted or unsubstituted linear or branched alkyl having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; or NQ5Q6.

[0308] According to one embodiment of the present specification, Z2is deuterium; linear or branched alkyl having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, or linear or branched alkyl having 1 to 30 carbon atoms; or NQ5Q6.

[0309] According to one embodiment of the present specification, Z2is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; phenyl unsubstituted or substituted with deuterium, or linear or branched alkyl having 1 to 30 carbon atoms; or NQ5Q6.

[0310] According to one embodiment of the present specification, Z2is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; phenyl unsubstituted or substituted with deuterium or methyl; or NQ5Q6.

[0311] According to one embodiment of the present specification, Z1and Z3are hydrogen.

[0312] According to one embodiment of the present specification, Z1to Z3are deuterium.

[0313] According to one embodiment of the present specification, Q5and Q6are the same as or different from each other, and each is independently monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; fused ring group of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0314] According to one embodiment of the present specification, Q5and Q6are the same as or different from each other, and each is independently a phenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a biphenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fluorenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a dibenzofuranyl; or a dibenzothiophenyl.

[0315] According to one embodiment of the present specification, Q5and Q6are the same as or different from each other, and each is independently a phenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a biphenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fluorenyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a dibenzofuranyl; or a dibenzothiophenyl.

[0316] According to one embodiment of the present specification, Z1and G3are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is substituted or unsubstituted.

[0317] According to one embodiment of the present specification, Z1and G3are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0318] According to one embodiment of the present specification, Z1and G3are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0319] According to one embodiment of the present specification, Z1and G3are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0320] According to one embodiment of the present specification, A1is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted with NQ1Q2, a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a fused ring of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, Q1and Q2are the same as or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic ring group having 2 to 30 carbon atoms, R5to R8are the same as or different from each other and are each independently hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or are bonded to an adjacent group to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a fused ring of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, Q3and Q4are the same as or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms,a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, Ar1is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms unsubstituted or substituted with any one or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and combinations thereof; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to A1to form any one of a monocyclic or polycyclic aromatic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and containing any one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocyclic ring having 2 to 30 carbon atoms, and fused rings thereof, Ar2is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms unsubstituted or substituted with any one or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and combinations thereof; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to R5to form any one of a monocyclic or polycyclic aromatic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and containing any one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocyclic ring having 2 to 30 carbon atoms, and fused rings thereof, at least one of Z1to Z3is deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium, or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or bonded to adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms;or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, which is unsubstituted or substituted by one or more substituents selected from the group consisting of linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, fused ring groups of aromatic and aliphatic hydrocarbon rings, and combinations thereof, and the remainder are hydrogen, Q5and Q6are the same as or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted by linear or branched alkyl groups having 1 to 30 carbon atoms; a fused ring group of monocyclic or polycyclic aromatic hydrocarbon rings having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon rings having 3 to 30 carbon atoms, which is unsubstituted or substituted by linear or branched alkyl groups having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring group having 2 to 30 carbon atoms, when Ar2and R5form a benzo when Ar2and R5form a benzo when Ar2and R5form a benzo when Ar2and R5form a benzo

[0321] According to one embodiment of the present specification, R1to R4are the same as or different from each other and are each independently hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms.

[0322] According to one embodiment of the present specification, R1to R4are the same as or different from each other, and each is independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to an adjacent group to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0323] According to one embodiment of the present specification, R1to R4are the same as or different from each other, and each is independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to an adjacent group to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. According to one embodiment of the present specification, R1to R4are the same as or different from each other, and each is independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to an adjacent group to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0324] ​According to one embodiment of the present specification, R1to R4are the same as or different from each other and are each independently hydrogen; methyl; tert-butyl; phenyl; or NQ3Q4, or are bonded to adjacent groups to form any of unsubstituted or methyl-substituted cyclohexane; benzene; unsubstituted or methyl- or tert-butyl-substituted benzofuran; unsubstituted or methyl- or tert-butyl-substituted benzothiophene; naphthofuran; naphthothiophene; unsubstituted or methyl-substituted indene; unsubstituted or methyl-substituted indole; unsubstituted or methyl-substituted indolinoindene; indolinoindole; unsubstituted or methyl-substituted tetrahydronaphthofuran; unsubstituted or methyl-substituted tetrahydronaphthothiophene; unsubstituted or methyl-substituted tetrahydrobenzoindene; benzo According to one embodiment of the present specification, Q3and Q4have the same definition as described above.

[0325] According to one embodiment of the present specification, R4is bonded to Ar1to form any of unsubstituted or substituted and having 2 to 30 carbon atoms, monocyclic or polycyclic aromatic heterocycle, monocyclic or polycyclic aliphatic heterocycle, and fused rings thereof, containing any one or more of N, S, O, and Si.

[0326] According to one embodiment of the present specification, R4is bonded to Ar1to form any of unsubstituted or substituted and having 2 to 30 carbon atoms, monocyclic or polycyclic aromatic heterocycle, monocyclic or polycyclic aliphatic heterocycle, and fused rings thereof, containing any one or more of N, S, O, and Si.

[0327] According to one embodiment of the present specification, R4is bonded to Ar1to form any of unsubstituted or substituted and having 2 to 30 carbon atoms, monocyclic or polycyclic aromatic heterocycle, monocyclic or polycyclic aliphatic heterocycle, and fused rings thereof, containing any one or more of N, S, O, and Si.

[0328] ​According to one embodiment of this specification, R4 is bonded to Ar1 to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, of dihydroquinoline; spiroquinoline fluorene; unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, of hexahydroindene; unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, of dihydroquinoline; Hexahydrobenzoquinoline; unsubstituted or substituted hexahydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophene pyrrole; dihydrobenzozasilanes unsubstituted or substituted dihydrobenzozasilanes with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirodibenzothiophene benzozasilane; benzo[…] Azides; benzothiazides; dihydroindopyrroles that are unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzoindole; or indoles that are unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0329] According to one embodiment of this specification, R4 is bonded to Ar1 to form an unsubstituted or methyl- or phenyl-substituted dihydroquinoline; spiroacridinequinoline; an unsubstituted or substituted hexahydroindene selected from methyl and tert-butyl groups or more; an unsubstituted or methyl- or phenyl-substituted dihydrobenzozoline; an unsubstituted or methyl- or phenyl-substituted hexahydrobenzozoline; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophenopyrrole; an unsubstituted or methyl- or phenyl-substituted dihydrobenzozasilane; spirobenzothiopyrrole dibenzozasilane; benzo[…]. Azides; benzothiazides; unsubstituted or methyl- or phenyl-substituted dihydroindopyrrole; benzoindole; or unsubstituted or tert-butyl, adamantyl, or phenyl-substituted indoles.

[0330] According to one embodiment of this specification, chemical formula 1 is selected from any of the following compounds.

[0331]

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[0940]

[0941]

[0942] In the compound, t-Bu is a tert-butyl group.

[0943] One embodiment of the present specification provides an organic light emitting device including the above compound.

[0944] In the present specification, the description that a certain member is "on" another member includes not only a case that a certain member is in contact with another member, but also a case that there is another member between the two members.

[0945] In the present specification, the description that a certain part "comprises" certain components means that it can further include other components, and does not exclude other components unless otherwise specifically stated.

[0946] In this specification, the term "layer" has the same meaning as "film" as commonly used in the art, and refers to a coating covering a target area. There is no limitation on the size of a "layer," and individual "layers" may have the same or different dimensions. According to one embodiment, the size of a "layer" may be the same as the entire device, may correspond to the size of a specific functional region, or may be as small as a single subpixel.

[0947] In this specification, the meaning of a specific material A being contained in a layer B includes both of the following: i) one or more types of material A being contained in a layer B, and ii) a layer B being formed of one or more layers, and material A being contained in one or more layers of a multilayered layer B.

[0948] In this specification, the meaning of a particular material A being contained in layers C or D includes the following three: i) being contained in one or more layers of one or more layers C, ii) being contained in one or more layers of one or more layers D, or iii) being contained in each of one or more layers C and one or more layers D.

[0949] In this specification, “deuteration,” “deuterated,” or “deuterated” means the substitution of hydrogen at a substituted position in a compound by deuteration.

[0950] In this specification, "deuterated by X%", "X% deuterated", "X% degree of deuteration" or "X% rate of deuteration" means that X% of the hydrogens at the substituted positions in the corresponding structure are deuterated. For example, when the corresponding structure is dibenzofuran, "25% deuterated", "25% deuterated", "25% degree of deuteration", or "25% rate of deuteration" means that two of the eight hydrogens at the substituted positions in dibenzofuran are deuterated.

[0951] In this specification, the degree of deuteration can be expressed using known methods such as nuclear magnetic resonance (NMR). 1 It is determined by H NMR, TLC / MS (thin-layer chromatography / mass spectrometry) or MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[0952] One embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more layers of organic material contain a compound represented by chemical formula 1.

[0953] The organic material layer of the organic light-emitting device of the present specification can be formed in a single layer structure, but can also be formed in a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present specification can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light-emitting device is not limited thereto, and can include a smaller number of organic layers.

[0954] In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 1.

[0955] In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 1 as a dopant of the light-emitting layer.

[0956] In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 1 as a blue fluorescent dopant of the light-emitting layer.

[0957] In one embodiment of the present specification, the organic light-emitting device further includes one, two, or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0958] In one embodiment of the present specification, the light-emitting layer further contains a host compound.

[0959] In one embodiment of the present specification, the light-emitting layer further contains a host compound, and at least one hydrogen at a substitutable position in the host compound is substituted with deuterium.

[0960] In one embodiment of the present specification, when the host compound is substituted with deuterium, the host compound is substituted with deuterium by 30% or more. In another embodiment, the host compound is substituted with deuterium by 40% or more. In another embodiment, the host compound is substituted with deuterium by 60% or more. In another embodiment, the host compound is substituted with deuterium by 80% or more. In another embodiment, the host compound is substituted with deuterium by 100%.

[0961] In one embodiment of the present specification, the light-emitting layer further contains a compound represented by the following Chemical Formula H.

[0962] [Chemical Formula H]

[0963]

[0964] In Chemical Formula H,

[0965] L20and L21are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene,

[0966] Ar20and Ar21are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclyl,

[0967] R200and R201are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl; a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclyl, and

[0968] r201is an integer of 1 to 7, and when r201is 2 or more, two or more R201are the same as or different from each other.

[0969] In one embodiment of the present specification, L20and L21are the same as or different from each other and are each independently a direct bond; a monocyclic or polycyclic arylene having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene having 2 to 30 carbon atoms.

[0970] In one embodiment of the present specification, L20and L21are the same as or different from each other and are each independently a direct bond; a monocyclic or polycyclic arylene having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene having 2 to 20 carbon atoms.

[0971] In one embodiment of the present specification, L20and L21are the same as or different from each other and are each independently a direct bond; a phenylene unsubstituted or substituted with deuterium; a biphenylene unsubstituted or substituted with deuterium; a naphthylene unsubstituted or substituted with deuterium; a bifer unsubstituted or substituted with deuterium; or a dibenzothiophene unsubstituted or substituted with deuterium.

[0972] In one embodiment of the present specification, Ar20and Ar21are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclyl having 2 to 30 carbon atoms.

[0973] In one embodiment of the present specification, Ar20and Ar21are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclyl having 2 to 20 carbon atoms.

[0974] In an embodiment of the specification, Ar20and Ar21are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic to tricyclic aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tricyclic heterocyclic group having 6 to 20 carbon atoms.

[0975] In an embodiment of the specification, Ar20and Ar21are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthryl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted phenalene; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted benzofluorenyl; a substituted or unsubstituted furanyl; a substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[0976] In an embodiment of the specification, Ar20and Ar21are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthryl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted phenalene; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted benzofluorenyl; a substituted or unsubstituted furanyl; a substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[0977] In an embodiment of the specification, Ar20and Ar21are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthryl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted phenalene; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted benzofluorenyl; a substituted or unsubstituted furanyl; a substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[0978] In an embodiment of the specification, Ar20is a substituted or unsubstituted heterocyclic group, and Ar21is a substituted or unsubstituted aryl group.

[0979] In an embodiment of the disclosure, R200 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0980] In an embodiment of the disclosure, R200 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0981] In an embodiment of the disclosure, R200 is hydrogen; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0982] In an embodiment of the disclosure, R200 is hydrogen; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

[0983] In an embodiment of the disclosure, R200 is hydrogen; a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0984] In an embodiment of the disclosure, R200 is hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthryl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted indacenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted furanyl group; a substituted or unsubstituted thienyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted naphthobenzothiophenyl group.

[0985] In an embodiment of the description, R200 is hydrogen; deuterium; phenyl which is unsubstituted or substituted with deuterium, or monocyclic or polycyclic aryl having 6 to 20 carbon atoms; biphenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; naphthyl which is unsubstituted or substituted with deuterium, phenyl, or naphthyl; dibenzofuranyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; naphthobenzofuranyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; dibenzothiophenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; or naphthobenzothiophenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms.

[0986] In an embodiment of the description, R200 is hydrogen; deuterium; phenyl which is unsubstituted or substituted with deuterium, or monocyclic or polycyclic aryl having 6 to 20 carbon atoms; biphenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; naphthyl which is unsubstituted or substituted with deuterium, phenyl, or naphthyl; dibenzofuranyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; naphthobenzofuranyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; dibenzothiophenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; or naphthobenzothiophenyl which is unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms.

[0987] According to an embodiment of the description, R201 is hydrogen.

[0988] According to an embodiment of the description, R201 is deuterium.

[0989] In an embodiment of the description, when the compound represented by Chemical Formula H is substituted with deuterium, 30% or more of H at the substitutable position is substituted with deuterium. In another embodiment, in the structure of Chemical Formula H, 40% or more of hydrogen at the substitutable position is substituted with deuterium. In another embodiment, in the structure of Chemical Formula H, 60% or more of hydrogen at the substitutable position is substituted with deuterium.

[0990] In another embodiment, in the structure of Chemical Formula H, 80% or more of hydrogen at the substitutable position is substituted with deuterium. In another embodiment, in the structure of Chemical Formula H, 100% of hydrogen at the substitutable position is substituted with deuterium.

[0991] In an embodiment of the description, the compound represented by Chemical Formula H is any one selected from the following compounds.

[0992]

[0993]

[0994]

[0995]

[0996]

[0997]

[0998]

[0999]

[1000]

[1001]

[1002]

[1003]

[1004]

[1005]

[1006]

[1007]

[1008]

[1009]

[1010]

[1011]

[1012] According to one embodiment of the present specification, the compound represented by Chemical Formula H can be prepared as in the following General Formula 1, however, the preparation is not limited thereto.

[1013] [General Formula 1]

[1014]

[1015] In General Formula 1,

[1016] Ar1 has the same limitation as -L20-Ar20 of Chemical Formula H,

[1017] Ar2 has the same limitation as -L21-Ar21 of Chemical Formula H, and the anthracene nucleus of General Formula 1 can be further substituted with R200 and R201.

[1018] In one embodiment of the present specification, in the light-emitting layer, the compound represented by Chemical Formula 1 is used as a dopant, and the compound represented by Chemical Formula H is used as a host.

[1019] In one embodiment of the present specification, when the light-emitting layer includes a host and a dopant, the content of the dopant can be selected in the range of 0.01 parts by weight to 10 parts by weight, based on 100 parts by weight of the light-emitting layer, however, the content is not limited thereto.

[1020] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host and the dopant are included in the weight ratio of 99:1 to 1:99, preferably in the weight ratio of 99:1 to 70:30, and more preferably in the weight ratio of 99:1 to 90:10.

[1021] The light-emitting layer can further include a host material, and the host includes a fused aromatic ring derivative, a heterocycle-containing compound, or the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, or the like, the heterocycle-containing compound includes a carbazole derivative, a diphenyl furan derivative, a ladder furan compound, a pyrimidine derivative, a triazine derivative, or the like, and can include a mixture of two or more types thereof, however, the fused aromatic ring derivative and the heterocycle-containing compound are not limited thereto.

[1022] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a host and one or more types of dopant.

[1023] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a host and two or more types of mixed dopant.

[1024] According to one embodiment of the present specification, one or more of the two or more types of mixed dopant includes Chemical Formula 1, and the host includes a compound represented by Chemical Formula H. One or more of the two or more types of mixed dopant includes Chemical Formula 1, and as the remaining part, a dopant material known in the art can be used, however, the material is not limited thereto.

[1025] According to one embodiment of the present specification, one or more of the two or more types of mixed dopant includes Chemical Formula 1, and as the remaining part, one or more of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Chemical Formula 1 can be used, however, the material is not limited thereto.

[1026] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes one or more types of host.

[1027] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes two or more types of mixed host.

[1028] According to one embodiment of the present specification, one or more of the two or more types of mixed hosts is a compound represented by Chemical Formula H.

[1029] According to one embodiment of the present specification, the two or more types of mixed hosts are different from each other, and each is independently a compound represented by Chemical Formula H.

[1030] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains two types of mixed hosts.

[1031] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains two types of mixed hosts, the two types of mixed hosts are different from each other, and the two types of hosts are compounds represented by Chemical Formula H.

[1032] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, contains a first host represented by Chemical Formula H and a second host represented by Chemical Formula H, and the first host and the second host are different from each other.

[1033] According to one embodiment of the present specification, the first host: the second host is contained in a weight ratio of 95:5 to 5:95, and preferably in a weight ratio of 70:30 to 30:70.

[1034] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains a dopant and one or more types of hosts.

[1035] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a dopant and one or more types of hosts, the host includes a compound represented by Chemical Formula H, and the dopant includes a compound represented by Chemical Formula 1.

[1036] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains a dopant and two or more types of mixed hosts.

[1037] According to one embodiment of the present specification, one or more of the two or more types of mixed hosts includes a compound represented by Chemical Formula H, and the dopant includes a compound represented by Chemical Formula 1.

[1038] In the present specification, the two or more types of mixed hosts are different from each other.

[1039] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains a dopant and two types of mixed hosts.

[1040] According to one embodiment of the present specification, two types of mixed hosts are different from each other, and each independently includes a compound represented by Chemical Formula H, and the dopant includes a compound represented by Chemical Formula 1.

[1041] According to one embodiment of the present specification, a first host represented by Chemical Formula H; a second host represented by Chemical Formula H; and a dopant represented by Chemical Formula 1 are included, and the first host and the second host are different from each other.

[1042] According to one embodiment of the present specification, the organic material layer uses one or more types of hosts and one or more types of dopants, and the one or more types of hosts include a compound represented by Chemical Formula H, and the one or more types of dopants include a compound represented by Chemical Formula 1.

[1043] According to one embodiment of the present specification, the organic material layer uses two or more types of mixed hosts and two or more types of mixed dopants, and as the two or more types of mixed hosts, the same materials as described above can be used, and as the two or more types of mixed dopants, the same materials as described above can be used.

[1044] According to one embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a dopant material, and the dopant material includes a compound of Chemical Formula 1.

[1045] According to one embodiment of the present specification, the emission layer further includes a host and one or more types of dopants. As the one or more types of dopants, a dopant material known in the art can be used, however, the dopant is not limited thereto.

[1046] According to one embodiment of the present specification, the emission layer further includes one or more types of hosts. The one or more types of hosts include a compound represented by Chemical Formula H.

[1047] According to one embodiment of the present specification, the emission layer includes two or more types of mixed hosts. One or more types of the two or more types of mixed hosts include a compound represented by Chemical Formula H.

[1048] According to one embodiment of the present specification, the emission layer further includes two or more types of mixed hosts. The two types of mixed hosts are different from each other, and each independently includes a compound represented by Chemical Formula H.

[1049] In an embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode; an emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the emitting layer and the first electrode or between the emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes a compound represented by Chemical Formula 1.

[1050] In an embodiment of the present specification, as the two or more organic material layers, the two or more organic material layers can be selected from an emitting layer, a hole transport layer, a hole injection layer, a layer simultaneously performing hole transport and hole injection, and an electron blocking layer.

[1051] In an embodiment of the present specification, the organic light emitting device can include two or more electron transport layers, but is not limited thereto.

[1052] In an embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Chemical Formula 1. Specifically, in an embodiment of the present specification, the compound represented by Chemical Formula 1 can be included in one of the two or more electron transport layers, or can be included in each of the two or more electron transport layers.

[1053] Further, in an embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Chemical Formula 1 can be the same as or different from each other.

[1054] Further, in an embodiment of the present specification, the materials of each of the two or more electron transport layers can be the same as or different from each other.

[1055] In an embodiment of the present specification, the organic light emitting device can include two or more hole injection layers, but is not limited thereto.

[1056] Further, in an embodiment of the present specification, the materials of each of the two or more hole injection layers can be the same as or different from each other.

[1057] When the organic material layer including the compound represented by Chemical Formula 1 is an electron transport layer, the electron transport layer can further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. For example, the electron transport layer including the compound represented by Chemical Formula 1 can further include LiQ (lithium quinolate).

[1058] In one embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers contains the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 can be contained in one of the two or more hole transport layers, or can be contained in each of the two or more hole transport layers.

[1059] Further, in one embodiment of the present specification, when the compound represented by Chemical Formula 1 is contained in each of the two or more hole transport layers, the materials other than the compound represented by Chemical Formula 1 can be the same as or different from each other.

[1060] In one embodiment of the present specification, in addition to the organic material layer containing the compound represented by Chemical Formula 1, the organic material layer can include a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazole group, or a benzocarbazole group.

[1061] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[1062] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[1063] In one embodiment of the present specification, the organic light emitting device can be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate (normal type).

[1064] In one embodiment of the present specification, the organic light emitting device can be an organic light emitting device having a reverse structure in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate (inverted type).

[1065] For example, the structure of the organic light emitting device according to one embodiment of the present specification is shown in Figure 1 and Figure 2 . Figure 1 and Figure 2 The organic light emitting device is merely shown, and the organic light emitting device is not limited thereto.

[1066] Figure 1 The structure of the organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially laminated is shown. In such a structure, the compound can be contained in the light emitting layer 3.

[1067] Figure 2A structure of an organic light emitting device in which a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, a light emitting layer 3, a first electron transport layer 9, a second electron transport layer 10, an electron injection layer 11, and a second electrode 4 are sequentially laminated is shown. In such a structure, the compound can be contained in the light emitting layer 3.

[1068] The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that one or more of the organic material layers contains the compound, i.e., the compound represented by Chemical Formula 1.

[1069] When the organic light emitting device includes a plurality of organic material layers, the organic material layers can be formed of materials that are the same as or different from each other.

[1070] For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. Herein, the organic light emitting device can be manufactured by forming an anode on a substrate by depositing a metal, a metal oxide having conductivity, or an alloy thereof using a physical vapor deposition (PVD) method such as a sputtering method or an electron beam evaporation method, and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[1071] Further, in manufacturing the organic light emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer using a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.

[1072] In addition to such a method, the organic light emitting device can also be manufactured by sequentially laminating a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Laid-Open No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[1073] As a first electrode material, a material having a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Examples thereof include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrole, and polyaniline, but are not limited thereto.

[1074] As the second electrode material, a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Examples thereof include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multilayer structure material such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[1075] In the present specification, when the compound represented by Chemical Formula 1 is contained in an organic material layer other than the light-emitting layer, or an additional light-emitting layer is provided, the light-emitting material of the light-emitting layer is a material capable of emitting light in the visible region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having a favorable quantum efficiency for fluorescence or phosphorescence. Examples thereof include an 8-hydroxy-quinoline aluminum complex (Alq3); a carbazole-based compound; a dimeric styryl compound; BAlq; a 10-hydroxybenzoquinoline-metal compound; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; a polyfluorene; rubrene; and the like, but are not limited thereto. In the present specification, when the compound represented by Chemical Formula 1 is contained in an organic material layer other than the light-emitting layer, or an additional light-emitting layer is provided, the light-emitting material of the light-emitting layer is a material capable of emitting light in the visible region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having a favorable quantum efficiency for fluorescence or phosphorescence. Examples thereof include an 8-hydroxy-quinoline aluminum complex (Alq3); a carbazole-based compound; a dimeric styryl compound; BAlq; a 10-hydroxybenzoquinoline-metal compound; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; a polyfluorene; rubrene; and the like, but are not limited thereto.

[1076] The light-emitting layer can contain a host material and a dopant material. The host material includes a fused aromatic ring derivative, a heterocycle-containing compound, and the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, the heterocycle-containing compound includes a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, however, the material is not limited thereto.

[1077] When an additional compound is contained in addition to the compound represented by Chemical Formula 1, the dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes a pyrene, an anthracene, a periflanthene, and the like having an arylamine group. In addition, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two, or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, it includes a styrylamine, a styryldiamine, a styryltriamine, a styryltetramine, and the like, however, the styrylamine compound is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

[1078] ​The hole injection layer is a layer that injects holes from the electrode. The hole injection material preferably has an effect of injecting holes from the first electrode due to the ability to transport holes, and an excellent hole injection effect to the light emitting layer or light emitting material. Furthermore, the hole injection material is preferably a material having an excellent ability to prevent excitons generated in the light emitting layer from moving to the electron injection layer or electron injection material. Furthermore, a material having an excellent thin film formation ability is preferable. Furthermore, the HOMO (Highest Occupied Molecular Orbital) of the hole injection material is preferably between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include: metal porphyrin; oligothiophene; arylamine-based organic material; carbazole-based organic material; nitrile-based organic material; hexacyanohexaazatriphenylene-based organic material; quinacridone-based organic material; perylene-based organic material; conductive polymer based on polythiophene, such as anthraquinone or polyaniline; and the like, or a mixture of two or more of the above examples, but are not limited thereto.

[1079] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following Chemical Formula HI-1.

[1080] [Chemical Formula HI-1]

[1081]

[1082] In Chemical Formula HI-1,

[1083] R301 to R308 are the same as or different from each other, and each is independently hydrogen; deuterium; cyano; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring,

[1084] r301 and r302 are each an integer of 1 to 4,

[1085] r303 and r304 are each an integer of 1 to 3,

[1086] R301 are the same as or different from each other when r301 is 2 or more,

[1087] R302 are the same as or different from each other when r302 is 2 or more,

[1088] R303 are the same as or different from each other when r303 is 2 or more, and

[1089] R304 are the same as or different from each other when r304 is 2 or more.

[1090] According to one embodiment of the present specification, R301 to R304 are hydrogen.

[1091] According to an embodiment of this specification, R300 is a substituted or unsubstituted aryl group.

[1092] According to an embodiment of this specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[1093] According to an embodiment of this specification, R300 is a phenyl group.

[1094] According to an embodiment of this specification, R300 and R301 or R302 are bonded to form a substituted or unsubstituted ring.

[1095] According to an embodiment of this specification, R300 and R301 or R302 are bonded to form a substituted or unsubstituted heterocyclic ring.

[1096] According to an embodiment of this specification, R300 and R301 or R302 are bonded to form a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[1097] According to an embodiment of this specification, R300 and R301 or R302 are bonded to form an indole.

[1098] According to an embodiment of this specification, R305 to R308 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted amine group.

[1099] According to an embodiment of this specification, R305 to R308 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic diaryl amine group having 6 to 30 carbon atoms.

[1100] According to an embodiment of this specification, R305 to R308 are the same as or different from each other, and each independently a phenyl group; or a diphenyl amine group.

[1101] According to an embodiment of this specification, Chemical Formula HI-1 is represented by the following compound.

[1102]

[1103] According to an embodiment of this specification, the hole injection layer comprises a compound represented by the following Chemical Formula HI-2.

[1104] [Chemical Formula HI-2]

[1105]

[1106] In Chemical Formula HI-2,

[1107] at least one of X'1to X'6is N, and the rest are CH, and

[1108] R309to R314are the same as or different from each other, and each is independently hydrogen; deuterium; cyano; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[1109] According to one embodiment of the present specification, X'1to X'6are N.

[1110] According to one embodiment of the present specification, R309to R314are cyano.

[1111] According to one embodiment of the present specification, Chemical Formula HI-2 is represented by the following compound.

[1112]

[1113] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As a hole transport material, a material capable of receiving holes from the first electrode or the hole injection layer and moving the holes to the light-emitting layer, and having a high hole mobility, is preferred. Specific examples thereof include arylamine-based organic materials, carbazole-based organic materials, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, and the like, but are not limited thereto.

[1114] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following Chemical Formula HT-1.

[1115] [Chemical Formula HT-1]

[1116]

[1117] In Chemical Formula HT-1,

[1118] R'314, R315, and R316are the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and combinations thereof, or are bonded to adjacent groups to form a substituted or unsubstituted ring,

[1119] r315is an integer of 1 to 4, and when r315is 2 or more, two or more R315are the same as or different from each other, and

[1120] r316is an integer of 1 to 4, and when r316is 2 or more, two or more R316are the same as or different from each other.

[1121] According to an embodiment of the present specification, R'314is selected from any one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and a combination thereof.

[1122] According to an embodiment of the present specification, R'314is selected from any one of carbazolyl, phenyl, biphenyl, and a combination thereof.

[1123] According to an embodiment of the present specification, R315and R316are the same as or different from each other, and each independently substituted or unsubstituted aryl, or bonded to an adjacent group to form an alkyl-substituted aromatic hydrocarbon ring.

[1124] According to an embodiment of the present specification, R315and R316are the same as or different from each other, and each independently phenyl, or bonded to an adjacent group to form a methyl-substituted indene.

[1125] According to an embodiment of the present specification, Chemical Formula HT-1 is selected from the following compounds.

[1126]

[1127] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. As an electron transport material, a material that can well receive electrons from the second electrode and move the electrons to the light-emitting layer, and has a high electron mobility is preferred. Specific examples thereof include A1 complex of 8-hydroxyquinoline; complexes including Alq3; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives; LiQ; and the like, but are not limited thereto. The electron transport layer can be used with any desired first electrode material used in the art. In particular, a suitable first electrode material is a common material having a low work function and having a subsequent aluminum layer or silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and in each case, a subsequent aluminum layer or silver layer.

[1128] According to an embodiment of the present specification, the electron transport layer comprises a compound represented by the following Chemical Formula ET-1.

[1129] [Chemical Formula ET-1]

[1130]

[1131] In Chemical Formula ET-1,

[1132] at least one of X'7and X'8is N, and the other is CH,

[1133] R317to R322are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted aminyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to an adjacent group to form a substituted or unsubstituted ring,

[1134] L'1is a direct bond; substituted or unsubstituted arylene; or substituted or unsubstituted heteroarylene,

[1135] r322is an integer from 1 to 7, and when r322is 2 or more, R322are the same as or different from each other, and

[1136] I'1is an integer from 1 to 5, and when I'1is 2 or more, L'1are the same as or different from each other.

[1137] According to one embodiment of the present specification, R317to R322are the same as or different from each other, and are each independently hydrogen; or substituted or unsubstituted aryl, and adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

[1138] According to one embodiment of the present specification, R317to R322are the same as or different from each other, and are each independently hydrogen; phenyl; or naphthyl, or adjacent groups are bonded to each other to form benzene.

[1139] According to one embodiment of the present specification, L'1is substituted or unsubstituted arylene.

[1140] According to one embodiment of the present specification, L'1is phenylene.

[1141] According to one embodiment of the present specification, ET-1 is represented by the following compound.

[1142]

[1143] According to one embodiment of the present specification, the electron transport layer comprises a compound represented by the following chemical formula ET-2.

[1144] [Chemical Formula ET-2]

[1145]

[1146] In Chemical Formula ET-2,

[1147] T1to T3are the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof, or bonded to an adjacent group to form a substituted or unsubstituted ring,

[1148] t1is an integer of 1 to 4, and when t1is 2 or more, two or more T1are the same as or different from each other,

[1149] t2is an integer of 1 to 4, and when t2is 2 or more, two or more T2are the same as or different from each other, and

[1150] t3is an integer of 1 to 10, and when t3is 2 or more, two or more T3are the same as or different from each other.

[1151] According to one embodiment of the present specification, T1to T3are the same as or different from each other, and each is independently selected from any one of hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[1152] According to one embodiment of the present specification, T1to T3are the same as or different from each other, and each is independently selected from any one of hydrogen, a carbazolyl group, a phenyl group, a biphenyl group, a triazinyl group, and a combination thereof.

[1153] According to one embodiment of the present specification, ET-2 is represented by the following compound.

[1154]

[1155] The electron transport layer can further include a metal complex. As the metal, metals used in the art can be used.

[1156] The electron injection layer is a layer that injects electrons from an electrode. As the electron injection material, a material having an excellent electron transport ability, having an effect of injecting electrons from a second electrode, and having an excellent electron injection effect on a light-emitting layer or a light-emitting material is preferred. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has an excellent thin film formation ability is preferred. Specific examples thereof include fluorenones, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, tetracarboxylic acid, fluorenylidene methane, anthrone, etc.; derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; a mixture of two or more of the above examples; and the like, but are not limited thereto.

[1157] The metal complex compound includes lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), chlorogallium bis(2-methyl-8-quinolinate), gallium bis(2-methyl-8-quinolinate)(o-cresol), aluminum bis(2-methyl-8-quinolinate)(1-naphthol), gallium bis(2-methyl-8-quinolinate)(2-naphthol), etc., but is not limited thereto.

[1158] The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing the electrons injected from the electron injecting layer from passing through the light emitting layer and entering the hole injecting layer. Known materials can be used without limitation, and the electron blocking layer can be formed between the light emitting layer and the hole injecting layer or between the light emitting layer and a layer that simultaneously performs hole injection and hole transport.

[1159] According to one embodiment of the present specification, the electron blocking layer is represented by Chemical Formula HT-1.

[1160] The hole blocking layer is a layer that blocks holes from passing through the light emitting layer and reaching the cathode, and can generally be formed under the same conditions as the electron injecting layer. Specific examples thereof can include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine, triazine derivatives, etc., but are not limited thereto.

[1161] The organic light emitting device according to the present specification can be a top emission type, a bottom emission type, or a dual side emission type, depending on the material used.

[1162] In one embodiment of the present specification, the compound represented by Chemical Formula 1 can be contained in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

[1163] The compound according to the present specification can also be used in an organic light emitting device including an organic phosphorescent device, an organic solar cell, an organic photoconductor, an organic transistor, etc., under similar principles used in the organic light emitting device. For example, the organic solar cell can have a structure including an anode, a cathode, and a photoactive layer disposed between the anode and the cathode, and the photoactive layer can contain the compound.

[1164] The organic light emitting device according to the present specification can be included in and used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[1165] The organic light emitting device of the present specification can be manufactured using a commonly used organic light emitting device manufacturing method and materials, except that one or more organic material layers are formed using the above-described compound.

[1166] Hereinafter, the present specification will be described in detail with reference to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification can be modified in various other forms, and the scope of the present specification should not be interpreted as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided in order to more fully describe the present specification to those of ordinary skill in the art.

[1167] Further, according to one embodiment of the present specification, the compounds of the following synthesis examples are examples of Chemical Formula 1 of the present specification, and Chemical Formula 1 includes any one of the compounds M1 to M5 and M7 to M16, M18 to M84, M86 to M115, M117 to M128, M130, M131, M133 to M144, and M146 to M150 of the following synthesis examples 1 to 5 and 7 to 16, 18 to 84, 86 to 115, 117 to 128, 130, 131, 133 to 144, and 146 to 150.

[1168] Synthesis Example 1. Synthesis of Compound M1

[1169]

[1170] 1) Synthesis of Int1

[1171] Int1 (30 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene] (23.8 g), potassium phosphate tribasic (33.2 g), and bis(tri-tert-butylphosphine)palladium(0) (0.5 g) were introduced into 1,4-dioxane (300 ml) and water (100 ml) and refluxed for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int2 (33 g, yield 73%). MS [M+H]+ = 872

[1172] 2) Synthesis of Int2

[1173] Int1 (30 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene] (23.8 g), potassium phosphate tribasic (33.2 g), and bis(tri-tert-butylphosphine)palladium(0) (0.5 g) were introduced into 1,4-dioxane (300 ml) and water (100 ml) and refluxed for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int2 (33 g, yield 73%). MS [M+H]+ = 872 Int1 (30 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene] (23.8 g), potassium phosphate tribasic (33.2 g), and bis(tri-tert-butylphosphine)palladium(0) (0.5 g) were introduced into 1,4-dioxane (300 ml) and water (100 ml) and refluxed for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int2 (33 g, yield 73%). MS [M+H]+ = 872

[1174] 3) Synthesis of compound M1

[1175] Int2 (25 g) and boron triiodide (19.1 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M1 (8.1 g, yield 32%). MS [M+H]+ = 880

[1176] Synthesis Example 2. Synthesis of compound M2

[1177]

[1178] 1) Synthesis of Int3

[1179] Using the same equivalents and method as in the synthesis method of Int1, using N-([1,1'-biphenyl]-4-yl)-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int3 (48.5 g, yield 78%). MS [M+H]+ = 557

[1180] 2) Synthesis of Int4

[1181] Using the same equivalents and method as in the synthesis method of Int2, using Int3 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int4 (35.7 g, yield 75%). MS [M+H]+ = 882

[1182] 3) Synthesis of compound M2

[1183] Int4 (25 g) and boron triiodide (18.9 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M2 (7.3 g, yield 29%). MS [M+H]+ = 890

[1184] Synthesis Example 3. Synthesis of compound M3

[1185]

[1186] 1) Synthesis of Int5

[1187] Using the same equivalents and method as in the synthesis of Intl, using bis([l,l'-biphenyl]-4-yl)amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int5 (45.4 g, yield 80%). MS [M+H]+=509

[1188] 2) Synthesis of Int6

[1189] Using the same equivalents and method as in the synthesis of Int2, using Int5 and l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-benzo[4,5]thieno[3,2- b]indole instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H- spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int6 (32.3 g, yield 79%). MS [M+H]+=695

[1190] 3) Synthesis of Compound M3

[1191] Under nitrogen atmosphere, Int6 (25 g) and boron triiodide (23.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M3 (7.2 g, yield 28%). MS [M+H]+=703

[1192] Synthesis Example 4. Synthesis of Compound M4

[1193]

[1194] 1) Synthesis of Int7

[1195] Using the same equivalents and method as in the synthesis of Intl, using N-(5-(tert- butyl)-[l,l'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-4-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int7 (51.1 g, yield 75%). MS [M+H]+=605

[1196] 2) Synthesis of Int8

[1197] Using the same equivalents and method as in the synthesis of Int 2, using Int 7 and 9,9-dimethyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9,10- dihydroacridine instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 8 (28.8 g, yield 75%). MS [M+H]+= 778

[1198] 3) Synthesis of compound M4

[1199] Under nitrogen atmosphere, Int 8 (25 g) and boron triiodide (21.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M4 (7.1 g, yield 28%). MS [M+H]+= 786

[1200] Synthesis example 5. Synthesis of compound M5

[1201]

[1202] 1) Synthesis of Int 9

[1203] Using the same equivalents and method as in the synthesis of Int 1, using N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-3-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 9 (52.5 g, yield 77%). MS [M+H]+= 605

[1204] 2) Synthesis of Int 10

[1205] Using the same equivalents and method as in the synthesis of Int 2, using Int 9 and 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)aniline instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 10 (33.1 g, yield 79%). MS [M+H]+= 850

[1206] 3) Synthesis of compound M5

[1207] Int 10 (25 g) and boron triiodide (19.6 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M5 (7.4 g, yield 29%). MS [M+H]+=858

[1208] Synthesis Example 7. Synthesis of compound M7

[1209]

[1210] 1) Synthesis of Int 13

[1211] Using the same equivalents and method as in the synthesis method of Int 1, bis(9,9- dimethyl-9H-fluoren-3-yl)amine was used instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 13 (49.5 g, yield 75%). MS [M+H]+=589

[1212] 2) Synthesis of Int 14

[1213] Using the same equivalents and method as in the synthesis method of Int 2, Int 13 and 3,6- di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole were used instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 14 (31.2 g, yield 74%). MS [M+H]+=832

[1214] 3) Synthesis of compound M7

[1215] Int 14 (25 g) and boron triiodide (20.0 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M7 (7.3 g, yield 29%). MS [M+H]+=840

[1216] Synthesis Example 8. Synthesis of compound M8

[1217]

[1218] 1) Synthesis of Int 15

[1219] Using the same equivalents and method as in the synthesis of Intl, using N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 15 (49.7 g, yield 73%). MS [M+H]+= 605

[1220] 2) Synthesis of Int 16

[1221] Using the same equivalents and method as in the synthesis of Int 2, using Int 15 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 16 (27.1 g, yield 77%). MS [M+H]+= 711

[1222] 3) Synthesis of Int 17

[1223] Using the same equivalents and method as in the synthesis of Intl, using Int 16 (27 g) and 4-bromo-l,l'-biphenyl (8.9 g) instead of 3-bromo-5-chloro-l,l'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 17 (26 g, yield 79%). MS [M+H]+= 864

[1224] 4) Synthesis of compound M8

[1225] Under nitrogen atmosphere, Int 17 (25 g) and boron triiodide (19.3 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M8 (7.4 g, yield 29%). MS [M+H]+= 872

[1226] Synthesis example 9. Synthesis of compound M9

[1227]

[1228] 1) Synthesis of Int 18

[1229] Using the same equivalents and method as in the synthesis of Intl, using bis(9,9-dimethyl-9H-fluoren-2-yl)amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 18 (48.7 g, yield 74%). MS [M+H]+= 589

[1230] 2) Synthesis of Int 19

[1231] Using the same equivalents and method as in the synthesis of Intl, using Int 18 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 19 (28.1 g, yield 79%). MS [M+H]+= 695

[1232] 3) Synthesis of Int 20

[1233] Using the same equivalents and method as in the synthesis of Intl, using Int 19 (27 g) and 4-bromo-l,l'-biphenyl (9.1 g) instead of 3-bromo-5-chloro-l,l'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 20 (26.2 g, yield 80%). MS [M+H]+= 848

[1234] 4) Synthesis of compound M9

[1235] Under nitrogen atmosphere, Int 20 (25 g) and boron triiodide (19.6 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M9 (7.5 g, yield 30%). MS [M+H]+= 856

[1236] Synthesis example 10. Synthesis of compound MlO

[1237]

[1238] 1) Synthesis of Int 21

[1239] Using the same equivalents and method as in the synthetic method of Int 1, using N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,d]thiophene-2-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 21 (48.9 g, yield 73%). MS [M+H]+= 595

[1240] 2) Synthesis of Int 22

[1241] Using the same equivalents and method as in the synthetic method of Int 2, using Int 21 and 4-((4-(tert-butyl)phenyl)amino)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 22 (30.2 g, yield 75%). MS [M+H]+= 800

[1242] 3) Synthesis of Int 23

[1243] Under a nitrogen atmosphere, Int 22 (25 g) and boron triiodide (20.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 23 (7.4 g, yield 29%). MS [M+H]+= 808

[1244] 4) Synthesis of Int 24

[1245] Int 23 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.4 ml), and potassium carbonate (3.6 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred at reflux for 2 hours. After completion of the reaction, the resulting product was extracted, then column-purified to obtain Int 24 (9 g, yield 95%). MS [M+H]+= 1089

[1246] 5) Synthesis of Compound M10

[1247] Int24 (7 g), bis(4-(tert-butyl)phenyl)amine (1.8 g), pd(dba)2(0.11 g), Xphos (0.18 g), and cesium carbonate (6.3 g) were introduced into xylene (100 ml) under a nitrogen atmosphere, and stirred at reflux for 12 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M10 (5 g, yield 73%). MS [M+H]+= 1071

[1248] Synthesis Example 11. Synthesis of Compound M11

[1249]

[1250] 1) Synthesis of Int25

[1251] Using the same equivalents and method as in the synthesis method of Int1, using N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-2-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int25 (49.2 g, yield 76%). MS [M+H]+= 579

[1252] 2) Synthesis of Int26

[1253] Using the same equivalents and method as in the synthesis method of Int2, using Int25 and 4-((4-(tert-butyl)phenyl)amino)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int26 (30.1 g, yield 74%). MS [M+H]+= 784

[1254] 3) Synthesis of Int27

[1255] Int26 (25 g) and boron triiodide (21.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int27 (7.5 g, yield 30%). MS [M+H]+= 792

[1256] 4) Synthesis of Int28

[1257] Int27 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.4 ml) and potassium carbonate (3.7 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred under reflux for 2 hours. After completion of the reaction, the resulting product was extracted and then column-purified to obtain Int28 (9.1 g, yield 96%). MS [M+H]+= 1074

[1258] 5) Synthesis of compound M11

[1259] Int28 (7 g), bis(4-(tert-butyl)phenyl)amine (1.84 g), pd(dba)2 (0.11 g), Xphos (0.19 g) and cesium carbonate (6.4 g) were introduced into xylene (100 ml) and stirred under reflux for 12 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M11 (5.2 g, yield 76%). MS [M+H]+= 1055

[1260] Synthesis example 12. Synthesis of compound M12

[1261]

[1262] 1) Synthesis of Int29

[1263] Using the same equivalents and method as in the synthesis method of Int1, using 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int29 (39 g, yield 78%). MS [M+H]+= 445

[1264] 2) Synthesis of Int30

[1265] Int30 (37 g, yield 75%) was obtained in the same manner as in the synthesis of Int2, except that Int29 and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-amine were used instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene]. MS [M+H]+= 730

[1266] 3) Synthesis of compound M12

[1267] Int 30 (25 g) and boron triiodide (22.8 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain compound M12 (7.7 g, yield 30%). MS [M+H]+=738

[1268] Synthesis Example 13. Synthesis of compound M13

[1269]

[1270] 1) Synthesis of Int 31

[1271] Int 31 (39 g, yield 73%) was obtained in the same manner as in the synthesis of Int 2, except that 9-(5-chloro-[l,l'-biphenyl]-3-yl)-4a,9a-dimethyl-6- phenyl-2,3,4,4a,9,9a-hexahydro-lH-carbazole and N-(9,9-dimethyl-9H-fluoren-2-yl)- 9,9-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine were used instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene]. MS [M+H]+=830

[1272] 2) Synthesis of compound M13

[1273] Int 31 (25 g) and boron triiodide (20.1 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain compound M13 (7.3 g, yield 29%). MS [M+H]+=838

[1274] Synthesis Example 14. Synthesis of compound M14

[1275]

[1276] 1) Synthesis of Int 32

[1277] Using the same equivalents and method as in the synthesis of Int2, using Int29 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int32 (29 g, yield 78%). MS [M+H]+=551

[1278] 2) Synthesis of Int33

[1279] Using the same equivalents and method as in the synthesis of Intl, using Int32 (27 g) and 2-bromo-9,9-dimethyl-9H-fluorene (13.4 g) instead of 3-bromo-5-chloro-l,l'- biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int33 (27.2 g, yield 75%). MS [M+H]+=744

[1280] 3) Synthesis of compound M14

[1281] Under nitrogen atmosphere, Int33 (25 g) and boron triiodide (22.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M14 (7.6 g, yield 30%). MS [M+H]+=752

[1282] Synthesis example 15. Synthesis of compound M15

[1283]

[1284] 1) Synthesis of Int34

[1285] Using the same equivalents and method as in the synthesis of Intl, using 3,6-di-tert-butyl-9H-carbazole instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int34 (38.5 g, yield 74%). MS [M+H]+=467

[1286] 2) Synthesis of Int35

[1287] Using the same equivalents and method as in the synthesis of Int2, using Int34 and N-([1,1 '-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-fluoren-2-amine instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int35 (38.3 g, yield 75%). MS [M+H]+ = 792

[1288] 3) Synthesis of compound M15

[1289] Under a nitrogen atmosphere, Int35 (25 g) and boron triiodide (21.0 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M15 (7.7 g, yield 31 %). MS [M+H]+ = 800

[1290] Synthesis example 16. Synthesis of compound M16

[1291]

[1292] 1) Synthesis of Int36

[1293] Int36 (38.2 g, yield 78%) was obtained in the same way as in the synthesis of Int2, except that 3,6-di-tert-butyl-9-(5-chloro-[1,1 '-biphenyl]-3-yl-2',3',4',5',6'-d5)-9H- carbazole and N-([1,1 '-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)dibenzo[b,d]furan-2-amine were used instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene]. MS [M+H]+ = 771

[1294] 2) Synthesis of compound M16

[1295] Under a nitrogen atmosphere, Int36 (25 g) and boron triiodide (21.6 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M16 (7.4 g, yield 29%). MS [M+H]+ = 779

[1296] Synthesis example 18. Synthesis of compound M18

[1297]

[1298] 1) Synthesis of Int 38

[1299] Using the same equivalents and method as in the synthesis of Int 2, Int 34 and N- (dibenzo [b, d] furan-4-yl) -3- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzene- 1, 2-diamine were used instead of Int 1 and 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -10H-spiro [acridine-9, 9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 38 (40.2 g, yield 79%). MS [M+H]+ = 795

[1300] 2) Synthesis of compound M18

[1301] Int 38 (25 g) and boron triiodide (20.9 g) were introduced into 1, 2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M18 (7.7 g, yield 31%). MS [M+H]+ = 803

[1302] Synthesis Example 19. Synthesis of compound M19

[1303]

[1304] 1) Synthesis of Int 39

[1305] Using the same equivalents and method as in the synthesis of Int 2, Int 34 and 3- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-2-amine were used instead of Int 1 and 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -10H-spiro [acridine-9, 9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 39 (27.3 g, yield 74%). MS [M+H]+ = 574

[1306] 2) Synthesis of Int 40

[1307] ​Using the same equivalents and method as in the synthetic method of Int 1, using Int 39 (27 g) and 4-bromo-1,1'-biphenyl (11 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 40 (27.1 g, yield 79%). MS [M+H]+= 726

[1308] 3) Synthesis of compound M19

[1309] Under nitrogen atmosphere, Int 40 (25 g) and boron triiodide (23 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M19 (7.4 g, yield 29%). MS [M+H]+= 734

[1310] Synthesis example 20. Synthesis of compound M20

[1311]

[1312] 1) Synthesis of Int 41

[1313] Using the same equivalents and method as in the synthetic method of Int 1, using 3,6-diphenyl-9H-carbazole instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 41 (41.4 g, yield 73%). MS [M+H]+= 507

[1314] 2) Synthesis of Int 42

[1315] Using the same equivalents and method as in the synthetic method of Int 2, using Int 41 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 42 (27.7 g, yield 76%). MS [M+H]+= 614

[1316] 3) Synthesis of Int 43

[1317] Using the same equivalents and method as in the synthetic method of Intl, using Int42 (27 g) and 4-bromo-3.5-dimethyl-l, l '-biphenyl (11.5 g) instead of 3-bromo-5-chloro-l, l '-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int43 (26.5 g, yield 76%). MS [M+H]+= 794

[1318] 4) Synthesis of compound M20

[1319] Under a nitrogen atmosphere, Int43 (25 g) and boron triiodide (21.0 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M20 (7.5 g, yield 30%). MS [M+H]+= 802

[1320] Synthesis example 21. Synthesis of compound M21

[1321]

[1322] 1) Synthesis of Int44

[1323] Using the same equivalents and method as in the synthetic method of Intl, using Int34 and 3-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amino)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl) phenol instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int44 (35.5 g, yield 75%). MS [M+H]+= 740

[1324] 2) Synthesis of Int45

[1325] Under a nitrogen atmosphere, Int44 (25 g) and boron triiodide (22.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int45 (7.2 g, yield 28%). MS [M+H]+= 748

[1326] 3) Synthesis of Int46

[1327] Int45 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.5 ml) and potassium carbonate (3.9 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred under reflux for 2 hours. After completion of the reaction, the resulting product was extracted and then column-purified to obtain Int46 (9.2 g, yield 95%). MS [M+H]+=1030

[1328] 4) Synthesis of compound M21

[1329] Int46 (7 g), bis(4-(tert-butyl)phenyl)amine (1.9 g), pd(dba)2(O.12 g), Xphos (0.19 g) and cesium carbonate (6.7 g) were introduced into xylene (100 ml) and stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M21 (5.4 g, yield 79%). MS [M+H]+=1011

[1330] Synthesis example 22. Synthesis of compound M22

[1331]

[1332] 1) Synthesis of Int47

[1333] Using the same equivalents and method as in the synthesis method of Int1, using 9,9-dimethyl-9,10-dihydroacridine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro- naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int47 (34 g, yield 77%). MS [M+H]+=396

[1334] 2) Synthesis of Int48

[1335] Using the same equivalents and method as in the synthesis method of Int2, using Int47 and 10,10-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5.10- dihydroindeno[1,2-b]indole instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int48 (35.1 g, yield 78%). MS [M+H]+=593

[1336] 3) Synthesis of compound M22

[1337] Int 48 (25 g) and boron triiodide (28.1 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M22 (6.7 g, yield 26 %). MS [M+H]+ = 601

[1338] Synthesis Example 23. Synthesis of compound M23

[1339]

[1340] 1) Synthesis of Int 49

[1341] Using the same equivalents and method as in the synthesis of Int 2, using Int 47 and N-([l,l'-biphenyl]-4-yl)-5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 5,6,7,8-tetrahydronaphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 49 (42.4 g, yield 78 %). MS [M+H]+ = 716

[1342] 2) Synthesis of compound M23

[1343] Int 49 (25 g) and boron triiodide (23.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M23 (7.1 g, yield 28 %). MS [M+H]+ = 724

[1344] Synthesis Example 24. Synthesis of compound M24

[1345]

[1346] 1) Synthesis of Int 50

[1347] Using the same equivalents and method as in the synthetic method of Int2, using Int47 and N-([1,1'-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10- dihydroanthracen-2-amine instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int50 (43.1 g, yield 75%). MS [M+H]+= 764

[1348] 2) Synthesis of compound M24

[1349] Under nitrogen atmosphere, Int50 (25 g) and boron triiodide (21.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After the completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M24 (7.3 g, yield 29%). MS [M+H]+= 772

[1350] Synthesis Example 25. Synthesis of compound M25

[1351]

[1352] 1) Synthesis of Int51

[1353] Using the same equivalents and method as in the synthetic method of Int1, using 11H- benzo[a]carbazole instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int51 (36 g, yield 79%). MS [M+H]+= 405

[1354] 2) Synthesis of Int52

[1355] Using the same equivalents and method as in the synthetic method of Int2, using Int51 and N-(dibenzo[b,d]thiophen-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen- 3-amine instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after the completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int52 (44 g, yield 79%). MS [M+H]+= 750

[1356] 3) Synthesis of compound M25

[1357] Int52 (25 g) and boron triiodide (22.2 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M25 (7.2 g, yield 29 %). MS [M+H]+= 758

[1358] Synthesis Example 26. Synthesis of compound M26

[1359]

[1360] 1) Synthesis of Int53

[1361] Using the same equivalents and method as in the synthesis method of Intl, using N- (5-(tert-butyl)-[l,l'-biphenyl]-2-yl)dibenzo[b,d]furan-2-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int53 (47 g, yield 73 %). MS [M+H]+= 579

[1362] 2) Synthesis of Int54

[1363] Using the same equivalents and method as in the synthesis method of Int2, using Int53 and 4a,9a-dimethyl-6-phenyl-8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 2,3,4,4a,9,9a-hexahydro-lH-carbazole instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lOH-spiro[azepine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int54 (32.2 g, yield 76 %). MS [M+H]+= 820

[1364] 3) Synthesis of compound M26

[1365] Int54 (25 g) and boron triiodide (20.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M26 (7.4 g, yield 29 %). MS [M+H]+= 828

[1366] Synthesis Example 27. Synthesis of compound M27

[1367]

[1368] 1) Synthesis of Int55

[1369] Using the same equivalents and method as in the synthesis of Intl, using N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3- b]furan-3-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int55 (55 g, yield 77%). MS [M+H]+=639

[1370] 2) Synthesis of Int56

[1371] Using the same equivalents and method as in the synthesis of Intl, using Int55 and N-(4-(tert-butyl)-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine instead of Intl and 4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lOH-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int56 (34.2 g, yield 78%). MS [M+H]+=938

[1372] 3) Synthesis of compound M27

[1373] Under a nitrogen atmosphere, Int56 (25 g) and boron triiodide (17.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M27 (7.7 g, yield 31%). MS [M+H]+=946

[1374] Synthesis Example 28. Synthesis of compound M28

[1375]

[1376] 1) Synthesis of Int57

[1377] Using the same equivalents and method as in the synthesis of Intl, using Int55 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lOH- spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int57 (33.3 g, yield 80%). MS [M+H]+=882

[1378] 2) Synthesis of compound M28

[1379] Int 57 (25 g) and boron triiodide (18.9 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M28 (7.3 g, yield 29 %). MS [M+H]+= 890

[1380] Synthesis Example 29. Synthesis of compound M29

[1381]

[1382] 1) Synthesis of Int 58

[1383] Using the same equivalents and method as in the synthesis method of Int 2, using 5-(tert-butyl)-N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-N-(5-chloro-[l,l'-biphenyl]-3-yl)benzofuran-3- amine and 9,9-diphenyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine- 9,9'-fluorene] instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H- spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 58 (35.2 g, yield 78 %). MS [M+H]+= 882

[1384] 2) Synthesis of compound M29

[1385] Int 58 (25 g) and boron triiodide (18.9 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M29 (7.2 g, yield 29 %). MS [M+H]+= 889

[1386] Synthesis Example 30. Synthesis of compound M30

[1387]

[1388] 1) Synthesis of Int 59

[1389] Using the same equivalents and method as in the synthesis of Intl, using 5,5,8,8- tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8- tetrahydronaphtho[2,3-b]furan-3-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int59 (55.6 g, yield 79%). MS [M+H]+= 631

[1390] 2) Synthesis of Int60

[1391] Using the same equivalents and method as in the synthesis of Intl, using Int59 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int60 (27.8 g, yield 79%). MS [M+H]+= 738

[1392] 3) Synthesis of Int61

[1393] Using the same equivalents and method as in the synthesis of Intl, using Int60 (27 g) and 4-bromo-l,l'_biphenyl (8.6 g) instead of 3-bromo-5-chloro-l,l'_biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int61 (25.1 g, yield 77%). MS [M+H]+= 890

[1394] 4) Synthesis of Compound M30

[1395] Under a nitrogen atmosphere, Int61 (25 g) and boron triiodide (18.7 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M30 (7.2 g, yield 29%). MS [M+H]+= 898

[1396] Synthesis Example 31. Synthesis of Compound M31

[1397]

[1398] 1) Synthesis of Int62

[1399] Using the same equivalents and method as in the synthesis of Intl, using N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)benzo[b]thiophen-3-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 62 (44 g, yield 72%). MS [M+H]+= 545

[1400] 2) Synthesis of Int 63

[1401] Using the same equivalents and method as in the synthesis of Int 2, using Int 62 and N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 9H-fluoren-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 63 (34.2 g, yield 71%). MS [M+H]+= 870

[1402] 3) Synthesis of compound M31

[1403] Under nitrogen atmosphere, Int 63 (25 g) and boron triiodide (19.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M31 (7.2 g, yield 29%). MS [M+H]+= 878

[1404] Synthesis Example 32. Synthesis of compound M32

[1405]

[1406] 1) Synthesis of Int 64

[1407] Using the same equivalents and method as in the synthesis of Int 2, using Int 62 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 64 (32.2 g, yield 78%). MS [M+H]+= 898

[1408] 2) Synthesis of compound M32

[1409] Int 64 (25 g) and boron triiodide (18.5 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M32 (7.2 g, yield 29 %). MS [M+H]+= 906

[1410] Synthesis Example 33. Synthesis of compound M33

[1411]

[1412] 1) Synthesis of Int 65

[1413] Using the same equivalents and method as in the synthesis method of Int 2, using N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-N-(5-chloro-[l,l'-biphenyl]-3-yl)-5- isopropylbenzo[b]thiophen-3-amine and 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-2,3,4,4a,9,9a-hexahydro-lH-carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 65 (31.1 g, yield 75 %). MS [M+H]+= 808

[1414] 2) Synthesis of compound M33

[1415] Int 65 (25 g) and boron triiodide (20.6 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M33 (7.3 g, yield 29 %). MS [M+H]+= 816

[1416] Synthesis Example 34. Synthesis of compound M34

[1417]

[1418] 1) Synthesis of Int 66

[1419] Using the same equivalents and method as in the synthetic method of Int2, using N-(4-(tert-butyl)phenyl)-N-(5-chloro-[l,l'-biphenyl]-3-yl)-5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine and 8-(4,4,5,5- tetramethyl- 1,3,2-dioxaborolan-2-yl)- 7H-benzo [c] carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)- 10H-spiro [acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 66 (28.9 g, yield 73%). MS [M+H]+ = 760

[1420] 2) Synthesis of compound M34

[1421] Under a nitrogen atmosphere, Int 66 (25 g) and boron triiodide (21.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain compound M34 (7.3 g, yield 29%). MS [M+H]+ = 768

[1422] Synthesis Example 35. Synthesis of compound M35

[1423]

[1424] 1) Synthesis of Int 67

[1425] Using the same equivalents and method as in the synthetic method of Int 1, using 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)- 5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 67 (55.2 g, yield 78%). MS [M+H]+ = 633

[1426] 2) Synthesis of Int 68

[1427] Using the same equivalents and method as in the synthetic method of Int2, using Int67 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int68 (31.1 g, yield 75%). MS [M+H]+= 876

[1428] 3) Synthesis of compound M35

[1429] Under a nitrogen atmosphere, Int68 (25 g) and boron triiodide (19 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M35 (7.1 g, yield 28%). MS [M+H]+= 884

[1430] Synthesis example 36. Synthesis of compound M36

[1431]

[1432] 1) Synthesis of Int69

[1433] Using the same equivalents and method as in the synthetic method of Intl, using 5,5,8,8-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8- tetrahydronaphtho[2,3-b]thiophen-3-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int69 (54.3 g, yield 75%). MS [M+H]+= 647

[1434] 2) Synthesis of Int70

[1435] Using the same equivalents and method as in the synthetic method of Int2, using Int69 and l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int70 (27.7 g, yield 79%). MS [M+H]+= 754

[1436] 3) Synthesis of Int71

[1437] Using the same equivalents and method as in the synthetic method of Int 1, using Int 70 (27 g) and 4-bromo- dibenzo[b,d]furan (8.9 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 71 (26.2 g, yield 79%). MS [M+H]+=920

[1438] 4) Synthesis of compound M36

[1439] Under nitrogen atmosphere, Int 71 (25 g) and boron triiodide (18.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M36 (6.9 g, yield 27%). MS [M+H]+=928

[1440] Synthesis example 37. Synthesis of compound M37

[1441]

[1442] 1) Synthesis of Int 72

[1443] Using the same equivalents and method as in the synthetic method of Int 1, using Int 69 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 72 (27.1 g, yield 78%). MS [M+H]+=754

[1444] 2) Synthesis of Int 73

[1445] Using the same equivalents and method as in the synthetic method of Int 1, using Int 72 (27 g) and 4-bromo-1,1'-biphenyl (8.4 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 73 (25.1 g, yield 77%). MS [M+H]+=906

[1446] 3) Synthesis of compound M37

[1447] Int 73 (25 g) and boron triiodide (18.4 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M37 (6.8 g, yield 27 %). MS [M+H]+= 914

[1448] Synthesis Example 38. Synthesis of compound M38

[1449]

[1450] 1) Synthesis of Int 74

[1451] Using the same equivalents and method as in the synthesis method of Int 1, using N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphtho[2,3-b]thiophen-2-amine instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 74 (55.2 g, yield 75 %). MS [M+H]+= 655

[1452] 2) Synthesis of Int 75

[1453] Using the same equivalents and method as in the synthesis method of Int 2, using Int 74 and 5,5,8,8-tetramethyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- [1,1'-biphenyl]-4-yl)-5,6,7,8-tetrahydronaphthalen-2-amine instead of Int 1 and 4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 75 (33.2 g, yield 74 %). MS [M+H]+= 974

[1454] 3) Synthesis of compound M38

[1455] Int 75 (25 g) and boron triiodide (17.1 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M38 (7.2 g, yield 29 %). MS [M+H]+= 982

[1456] Synthesis Example 39. Synthesis of compound M39

[1457]

[1458] 1) Synthesis of Int76

[1459] Using the same equivalents and method as in the synthesis of Intl, using 10H- benzo[4,5]thieno[3,2-b]indole instead of bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int76 (36.1 g, yield 78%). MS [M+H]+= 411

[1460] 2) Synthesis of Int77

[1461] Using the same equivalents and method as in the synthesis of Int2, using Int76 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int77 (30.1 g, yield 80%). MS [M+H]+= 518

[1462] 3) Synthesis of Int78

[1463] Using the same equivalents and method as in the synthesis of Intl, using Int77 (27 g) and 2-bromo-9,9-dimethyl-9H-fluorene (14.3 g) instead of 3-bromo-5-chloro-l,l'- biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int78 (26.6 g, yield 72%). MS [M+H]+= 710

[1464] 4) Synthesis of compound M39

[1465] Under nitrogen atmosphere, Int78 (25 g) and boron triiodide (23.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M39 (7.3 g, yield 29%). MS [M+H]+= 718

[1466] Synthesis Example 40. Synthesis of compound M40

[1467]

[1468] 1) Synthesis of Int79

[1469] Using the same equivalence and method as in the synthesis of Int2, Int76 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole were used instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-10H-spiro[acridin-9,9′-fluorene], and after the reaction was complete, the result was extracted and then recrystallized to obtain Int79 (34.5 g, yield 72%). MS[M+H]+=654

[1470] 2) Synthesis of compound M40

[1471] Under a nitrogen atmosphere, Int79 (25 g) and boron triiodide (25.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound M40 (7.2 g, yield 28%). MS[M+H]+=662

[1472] Synthesis Example 41. Synthesis of Compound M41

[1473]

[1474] 1) Synthesis of Int80

[1475] Using the same stoichiometry and method as in the synthesis of Int1, 10H-phenanthrene was used. Azine was used instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)amine, and after the reaction was complete, the result was extracted and then recrystallized to obtain Int80 (32.2 g, yield 78%). MS[M+H]+=371

[1476] 2) Synthesis of Int81

[1477] Using the same equivalence and method as in the synthesis of Int2, Int80 and N-([1,1′-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phen Thio-2-amine was used to replace Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)-10H-spiro[acridin-9,9′-fluorene], and after the reaction was complete, the result was extracted and then recrystallized to obtain Int81 (42 g, yield 74%). MS[M+H]+=702

[1478] 3) Synthesis of compound M41

[1479] Int 81 (25 g) and boron triiodide (23.7 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M41 (7.3 g, yield 29 %). MS [M+H]+= 710

[1480] Synthesis Example 42. Synthesis of compound M42

[1481]

[1482] 1) Synthesis of Int 82

[1483] Using the same equivalents and method as in the synthesis of Int 1, N-(5-(tert- butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,e][1,4]diazepine-2-amine was used instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 82 (47.1 g, yield 71 %). MS [M+H]+= 595

[1484] 2) Synthesis of Int 83

[1485] Using the same equivalents and method as in the synthesis of Int 2, Int 82 and 1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole were used instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 83 (29.8 g, yield 76 %). MS [M+H]+= 782

[1486] 3) Synthesis of compound M42

[1487] Int 83 (25 g) and boron triiodide (21.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M42 (7.5 g, yield 30 %). MS [M+H]+= 790

[1488] Synthesis Example 43. Synthesis of compound M43

[1489]

[1490] 1) Synthesis of Int 84 ​

[1491] Using the same equivalents and method as in the synthesis of Intl, Int 84 (46.6 g, yield 73%) was obtained using bis(dibenzo[b,e][l,4]diazepan-l-yl)amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine and after the completion of the reaction, the resulting product was extracted and then recrystallized. MS [M+H]+= 569

[1492] 2) Synthesis of Int 85

[1493] Using the same equivalents and method as in the synthesis of Intl, Int 85 (27.2 g, yield 76%) was obtained using Int 84 and 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-l-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after the completion of the reaction, the resulting product was extracted and then recrystallized. MS [M+H]+= 676

[1494] 3) Synthesis of Int 86

[1495] Using the same equivalents and method as in the synthesis of Intl, Int 86 (25.5 g, yield 77%) was obtained using Int 85 (27 g) and 4-bromo-l,l'-biphenyl (9.3 g) instead of 3-bromo-5-chloro-l,l'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine, and after the completion of the reaction, the resulting product was extracted and then recrystallized. MS [M+H]+= 828

[1496] 4) Synthesis of compound M43

[1497] Under nitrogen atmosphere, Int 86 (25 g) and boron triiodide (20.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M43 (7.4 g, yield 29%). MS [M+H]+= 836

[1498] Synthesis Example 44. Synthesis of compound M44

[1499]

[1500] 1) Synthesis of Int 87

[1501] ​Using the same equivalents and method as in the synthetic method of Int 1, using N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)thianthrene-2-amine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 87 (51 g, yield 73%). MS [M+H]+= 627

[1502] 2) Synthesis of Int 88

[1503] Using the same equivalents and method as in the synthetic method of Int 2, using Int 87 and 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-benzo[f]indol-3-ol instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 88 (28.1 g, yield 72%). MS [M+H]+= 814

[1504] 3) Synthesis of Int 89

[1505] Under a nitrogen atmosphere, Int 88 (25 g) and boron triiodide (20.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 89 (7.5 g, yield 30%). MS [M+H]+= 822

[1506] 4) Synthesis of Int 318

[1507] Int 89 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.3 ml) and potassium carbonate (3.6 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred at reflux for 2 hours. After completion of the reaction, the resulting product was extracted, then column-purified to obtain Int 318 (8.8 g, yield 94%). MS [M+H]+= 1104

[1508] 5) Synthesis of Compound M44

[1509] Int318 (7 g), diphenylamine (1.1 g), pd(dba)2(0.11 g), Xphos (0.18 g) and cesium carbonate (6.3 g) were introduced into xylene (100 ml) under nitrogen atmosphere and stirred at reflux for 12 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M44 (4.9 g, yield 79 %). MS [M+H]+= 973

[1510] Synthesis Example 45. Synthesis of compound M45

[1511]

[1512] 1) Synthesis of Int90

[1513] Using the same equivalents and method as in the synthesis method of Int1, using N1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-N3,N3-diphenylbenzene-1,3-diamine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int90 (54.3 g, yield 75 %). MS [M+H]+= 648

[1514] 2) Synthesis of Int91

[1515] Using the same equivalents and method as in the synthesis method of Int2, using Int90 and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,e][1,4]oxazepine-2-amine instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int91 (32.6 g, yield 73 %). MS [M+H]+= 963 3) Synthesis of compound M45

[1516] Int91 (25 g) and boron triiodide (17.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M45 (7.3 g, yield 29 %). MS [M+H]+= 971 Synthesis Example 46. Synthesis of compound M46

[1517]

[1518] ​

[1519] 1) Synthesis of Int 92

[1520] Using the same equivalents and method as in the synthesis of Int 2, using Int 90 and N-([1,1 '-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9,10-dihydroanthracen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 92 (35.2 g, yield 75%). MS [M+H]+ = 1015

[1521] 2) Synthesis of compound M46

[1522] Under nitrogen atmosphere, Int 92 (25 g) and boron triiodide (16.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M46 (7.5 g, yield 30%). MS [M+H]+ = 1023

[1523] Synthesis Example 47. Synthesis of compound M47

[1524]

[1525] 1) Synthesis of Int 93

[1526] Using the same equivalents and method as in the synthesis of Int 1, using N1-(5-(tert-butyl)- [1,1 '-biphenyl]-2-yl)-N3,N3-diphenylbenzene-1,3-diamine instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 93 (52.5 g, yield 71 %). MS [M+H]+ = 656

[1527] 2) Synthesis of Int 94

[1528] Using the same equivalents and method as in the synthesis of Int 2, using Int 93 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[b]carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 94 (29.8 g, yield 78%). MS [M+H]+ = 837

[1529] 3) Synthesis of compound M47

[1530] Int 94 (25 g) and boron triiodide (19.9 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M47 (7.5 g, yield 30 %). MS [M+H]+= 845

[1531] Synthesis example 48. Synthesis of compound M48

[1532]

[1533] 1) Synthesis of Int 95

[1534] Using the same equivalents and method as in the synthesis method of Int 2, using Int 93 and 8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 95 (29.4 g, yield 77 %). MS [M+H]+= 837

[1535] 2) Synthesis of compound M48

[1536] Int 95 (25 g) and boron triiodide (19.9 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M48 (7.1 g, yield 28 %). MS [M+H]+= 845

[1537] Synthesis example 49. Synthesis of compound M49

[1538]

[1539] 1) Synthesis of Int 96

[1540] Using the same equivalents and method as in the synthetic method of Int 1, using 3'- bromo-5'-chloro-2-methyl-1,1'-biphenyl (30 g) and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1,1,5,5,8,8- hexamethyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-3-amine (51 g) instead of 3- bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2- yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 96 (53.5 g, yield 74%). MS [M+H]+= 679

[1541] 2) Synthesis of Int 97

[1542] Using the same equivalents and method as in the synthetic method of Int 2, using Int 96 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[b]carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 97 (28.8 g, yield 76%). MS [M+H]+= 860

[1543] 3) Synthesis of Compound M49

[1544] Under a nitrogen atmosphere, Int 97 (25 g) and boron triiodide (19.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M49 (7.2 g, yield 29%). MS [M+H]+= 868

[1545] Synthesis Example 50. Synthesis of Compound M50

[1546]

[1547] 1) Synthesis of Int 98

[1548] Using the same equivalents and method as in the synthetic method of Int 1, using 3'- bromo-5'-chloro-2-methyl-1,1'-biphenyl (30 g) and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl) dibenzo[b,d]thiophene-4-amine (43.4 g) instead of 3-bromo-5-chloro-1,1'- biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 98 (49.4 g, yield 76%). MS [M+H]+= 609

[1549] 2) Synthesis of Int 99

[1550] Using the same equivalents and method as in the synthetic method of Int 2, using Int 98 and 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)aniline instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine- 9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 99 (29.9 g, yield 71%). MS [M+H]+= 854

[1551] 3) Synthesis of Compound M50

[1552] Under a nitrogen atmosphere, Int 99 (25 g) and boron triiodide (19.5 g) were introduced into 1,2-dichlorobenzene (250 ml), and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M50 (7.3 g, yield 29%). MS [M+H]+= 862

[1553] Synthesis Example 51. Synthesis of Compound M51

[1554]

[1555] 1) Synthesis of Int 100

[1556] Using the same equivalents and method as in the synthetic method of Int 1, using 3'-bromo-5'-chloro-2-methyl-1,1'-biphenyl (30 g) and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-7,7,10,10-tetramethyl-7,8,9,10-tetrahydrobenzo[b]naphtho[2,3-d]thiophen-3-amine (55.2 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 100 (53.5 g, yield 70%). MS [M+H]+ = 719

[1557] 2) Synthesis of Int 101

[1558] Using the same equivalents and method as in the synthetic method of Int 2, using Int 100 and 9,9-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroacridine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 101 (27.7 g, yield 74%). MS [M+H]+ = 892

[1559] 3) Synthesis of Compound M51

[1560] Under a nitrogen atmosphere, Int 101 (25 g) and boron triiodide (18.7 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M51 (7.1 g, yield 28%). MS [M+H]+ = 900

[1561] Synthesis Example 52. Synthesis of Compound M52

[1562]

[1563] 1) Synthesis of Int 102

[1564] Using the same equivalents and method as in the synthesis of Intl, using 3'- bromo-5'-chloro-2,6-dimethyl-l,l'-biphenyl (30 g) and 3,6-di-tert-butyl-9H-carbazole (28.4 g) instead of 3-bromo-5-chloro-l,l'-biphenyl and bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Intl 02 (38.1 g, yield 76%). MS [M+H]+= 495

[1565] 2) Synthesis of Int103

[1566] Using the same equivalents and method as in the synthesis of Intl, using Intl 02 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int103 (27.7 g, yield 76%). MS [M+H]+= 602

[1567] 3) Synthesis of Int104

[1568] Using the same equivalents and method as in the synthesis of Intl, using Intl 03 (27 g) and 4-bromo-l,l'-biphenyl (10.5 g) instead of 3-bromo-5-chloro-l,l'- biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Intl 04 (25.4 g, yield 75%). MS [M+H]+= 754

[1569] 4) Synthesis of compound M52

[1570] Under nitrogen atmosphere, Intl 04 (25 g) and boron triiodide (22.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M52 (7.2 g, yield 29%). MS [M+H]+= 762

[1571] Synthesis Example 53. Synthesis of compound M53

[1572]

[1573] 1) Synthesis of Int105

[1574] Using the same equivalents and method as in the synthesis of Intl, using 3'- bromo-5'-chloro-2,4,6-trimethyl-l,l '-biphenyl (30 g) and bis(9,9-dimethyl-9H-fluoren-2- yl)amine (27.1 g) instead of 3-bromo-5-chloro-l,l '-biphenyl and bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int105 (46.2 g, yield 76%). MS [M+H]+= 631

[1575] 2) Synthesis of Int106

[1576] Using the same equivalents and method as in the synthesis of Int2, using Int105 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Intl and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'- fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int106 (25.3 g, yield 72%). MS [M+H]+= 738

[1577] 3) Synthesis of Int107

[1578] Using the same equivalents and method as in the synthesis of Intl, using Int106 (27 g) and 4-bromo-l,l '-biphenyl (8.5 g) instead of 3-bromo-5-chloro-l,l '-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int107 (25.1 g, yield 77%). MS [M+H]+= 890

[1579] 4) Synthesis of compound M53

[1580] Under nitrogen atmosphere, Int107 (25 g) and boron triiodide (18.7 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M53 (7 g, yield 28%). MS [M+H]+= 898

[1581] Synthesis Example 54. Synthesis of compound M54

[1582]

[1583] 1) Synthesis of Int108

[1584] Using the same equivalents and method as in the synthesis of Int 1, using 1-bromo-3- chloro-5-methylbenzene (30 g) instead of 3-bromo-5-chloro-1,1'-biphenyl, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 108 (56 g, yield 75%). MS [M+H]+=515

[1585] 2) Synthesis of Int 109

[1586] Using the same equivalents and method as in the synthesis of Int 2, using Int 108 and N-([1,1'- biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]- 2',3',4',5',6'-d5-4-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H- spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 109 (34 g, yield 72%). MS [M+H]+=810

[1587] 3) Synthesis of compound M54

[1588] Under nitrogen atmosphere, Int 109 (25 g) and boron triiodide (20.6 g) were introduced into 1,2- dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M54 (7.2 g, yield 29%). MS [M+H]+=818

[1589] Synthesis Example 55. Synthesis of compound M55

[1590]

[1591] 1) Synthesis of Int 110

[1592] Using the same equivalents and method as in the synthesis of Int 2, using Int 108 and 3-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) dibenzo[b,d]furan-4-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H- spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 110 (36 g, yield 73%). MS [M+H]+=848

[1593] 2) Synthesis of compound M55

[1594] Int 110 (25 g) and boron triiodide (19.6 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M55 (7.5 g, yield 30%). MS [M+H]+= 856

[1595] Synthesis example 56. Synthesis of compound M56

[1596]

[1597] 1) Synthesis of Int 111

[1598] Using the same equivalents and method as in the synthesis method of Int 2, using N-(3-chlorophenyl-4,5,6-d3)-5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine and 2-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)dibenzo[b,d]thiophen-3-amine instead of Int 1 and 4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 111 (37.6 g, yield 74%). MS [M+H]+= 853

[1599] 2) Synthesis of compound M56

[1600] Int 111 (25 g) and boron triiodide (19.5 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M56 (7.2 g, yield 29%). MS [M+H]+= 861

[1601] Synthesis example 57. Synthesis of compound M57

[1602]

[1603] 1) Synthesis of Int 112

[1604] Using the same equivalences and methods as in the synthesis of Int1, 1-bromo-3-chloro-5-methylbenzene (30 g) and di([1,1′-biphenyl]-4-yl)amine (46.9 g) were used instead of 3-bromo-5-chloro-1,1′-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine, and after the reaction was complete, the result was extracted and then recrystallized to obtain Int112 (51 g, yield 78%). MS[M+H]+=447

[1605] 2) Synthesis of Int113

[1606] Using the same stoichiometry and method as in the synthesis of Int2, Int112 and N-(4-(tert-butyl)phenyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)dibenzo[b,d]furan-2-amine were used instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-10H-spiro[acridin-9,9′-fluorene], and after the reaction was complete, the result was extracted and then recrystallized to obtain Int113 (37 g, 76% yield). MS[M+H]+=726

[1607] 3) Synthesis of compound M57

[1608] Under a nitrogen atmosphere, Int113 (25 g) and boron triiodide (23 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound M57 (7.4 g, yield 29%). MS[M+H]+=734

[1609] Synthesis Example 58: Synthesis of Compound M58

[1610]

[1611] 1) Synthesis of Int114

[1612] Using the same equivalence and method as in the synthesis of Int1, 1-bromo-3-chloro-5-methylbenzene (30 g) and N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-yl)dibenzo[b,e][1,4]di Int-2-amine (58.4 g) was used in place of 3-bromo-5-chloro-1,1′-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine, and after the reaction was complete, the product was extracted and then recrystallized to obtain Int114 (55 g, yield 72%). MS[M+H]+=525

[1613] 2) Synthesis of Int 115

[1614] Using the same equivalents and method as in the synthesis of Int 2, using Int 114 and N-([1,1 '-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-fluoren-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 115 (36.3 g, yield 75%). MS [M+H]+= 850

[1615] 3) Synthesis of compound M58

[1616] Under a nitrogen atmosphere, Int 115 (25 g) and boron triiodide (19.6 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M58 (7.5 g, yield 30%). MS [M+H]+= 858

[1617] Synthesis Example 59. Synthesis of compound M59

[1618]

[1619] 1) Synthesis of Int 115-2

[1620] Using the same equivalents and method as in the synthesis of Int 2, using Int 114 and N-(5-(tert-butyl)-[1,1 '-biphenyl]-2-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-9H-fluoren-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 115-2 (37.7 g, yield 73%). MS [M+H]+= 906

[1621] 2) Synthesis of compound M59

[1622] Under a nitrogen atmosphere, Int 115-2 (25 g) and boron triiodide (18.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M59 (7.7 g, yield 31%). MS [M+H]+= 914

[1623] Synthesis of compound M60

[1624]

[1625] 1) Synthesis of Int 116

[1626] Using the same equivalents and method as in the synthesis of Int 1, using 1-bromo-3-(tert-butyl)-5-chlorobenzene (30 g) and 10H-spiro[acridine-9,9'-fluorene] (40.2 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 116 (46 g, yield 76%). MS [M+H]+= 499

[1627] 2) Synthesis of Int 117

[1628] Using the same equivalents and method as in the synthesis of Int 2, using Int 116 and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 117 (36.6 g, yield 76%). MS [M+H]+= 798

[1629] 3) Synthesis of compound M60

[1630] Under nitrogen atmosphere, Int 117 (25 g) and boron triiodide (20.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M60 (6.9 g, yield 27%). MS [M+H]+= 806

[1631] Synthesis of compound M61

[1632]

[1633] 1) Synthesis of Int 118

[1634] Using the same equivalents and method as in the synthetic method of Int 1, using 1-bromo-3-chloro-5-methylbenzene (30 g) and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-1-amine (57.2 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 118 (55 g, yield 73 %). MS [M+H]+=517

[1635] 2) Synthesis of Int 119

[1636] Using the same equivalents and method as in the synthetic method of Int 2, using Int 118 and N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 119 (36.6 g, yield 77 %). MS [M+H]+=816

[1637] 3) Synthesis of Compound M61

[1638] Under a nitrogen atmosphere, Int 119 (25 g) and boron triiodide (20.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M61 (6.8 g, yield 27 %). MS [M+H]+=824

[1639] Synthesis Example 62. Synthesis of Compound M62

[1640]

[1641] 1) Synthesis of Int 120

[1642] Using the same equivalents and method as in the synthetic method of Int 1, using 1-bromo-3-chloro-5-methylbenzene (30 g) and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine (57.2 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 120 (62 g, yield 72 %). MS [M+H]+ = 593

[1643] 2) Synthesis of Int 121

[1644] Using the same equivalents and method as in the synthetic method of Int 2, using Int 120 and 10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-11H-benzo[a]carbazole instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 121 (31.1 g, yield 79 %). MS [M+H]+ = 774

[1645] 3) Synthesis of Compound M62

[1646] Under nitrogen atmosphere, Int 121 (25 g) and boron triiodide (21.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M62 (6.2 g, yield 25 %). MS [M+H]+ = 782

[1647] Synthesis Example 63. Synthesis of Compound M63

[1648]

[1649] 1) Synthesis of Int 122

[1650] Using the same equivalents and method as in the synthetic method of Int 2, using Int 120 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 122 (27.7 g, yield 78 %). MS [M+H]+ = 700

[1651] 2) Synthesis of Int 123

[1652] Using the same equivalents and method as in the synthesis of Int 1, Int 122 (27 g) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.0 g) were used instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro- naphthalen-2-yl)amine, and after the reaction was completed, the resulting product was extracted, then recrystallized to obtain Int 123 (25.3 g, yield 74%). MS [M+H]+= 886

[1653] 3) Synthesis of compound M63

[1654] Int 123 (25 g) and boron triiodide (18.8 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After the reaction was completed, the resulting product was extracted, then recrystallized to obtain compound M63 (6.7 g, yield 27%). MS [M+H]+= 894

[1655] Synthesis Example 64. Synthesis of compound M64

[1656]

[1657] 1) Synthesis of Int 124

[1658] Using the same equivalents and method as in the synthesis of Int 1, 1-bromo-3-chloro-5- methylbenzene (30 g) and 10H-benzo[4,5]thieno[3,2-b]indole (32.6 g) were used instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro- naphthalen-2-yl)amine, and after the reaction was completed, the resulting product was extracted, then recrystallized to obtain Int 124 (39 g, yield 77%). MS [M+H]+= 349

[1659] 2) Synthesis of Int 125

[1660] Using the same equivalents and method as in the synthesis of Int 2, Int 124 and 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole were used instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[azepine-9,9'- fluorene], and after the reaction was completed, the resulting product was extracted, then recrystallized to obtain Int 125 (33.5 g, yield 73%). MS [M+H]+= 536

[1661] 3) Synthesis of compound M64

[1662] Int 125 (25 g) and boron triiodide (31.2 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M64 (6.8 g, yield 27%). MS [M+H]+= 544

[1663] Synthesis example 65. Synthesis of compound M65

[1664]

[1665] 1) Synthesis of Int 126

[1666] Using the same equivalents and method as in the synthesis method of Int 1, using N1,N1-bis(4-(tert-butyl)phenyl)-N3-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalen-2-yl)benzene-1,3-diamine instead of bis(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 126 (58 g, yield 74%). MS [M+H]+= 698

[1667] 2) Synthesis of Int 127

[1668] Using the same equivalents and method as in the synthesis method of Int 2, using Int 126 and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-3-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[ azecin-9,9'-fluorene], and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 127 (32.4 g, yield 73%). MS [M+H]+= 1031

[1669] 3) Synthesis of compound M65

[1670] Int 127 (25 g) and boron triiodide (16.2 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M65 (6.9 g, yield 27%). MS [M+H]+= 1039

[1671] Synthesis Example 66. Synthesis of Compound M66

[1672]

[1673] 1) Synthesis of Int 128

[1674] Using the same equivalents and method as in the synthesis of Int 1, using 1-bromo-3-(tert-butyl)-5-chlorobenzene (30 g) and 9,9-dimethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro naphthalen-2-yl)-9H-fluoren-2-amine (49.6 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 128 (53 g, yield 76 %). MS [M+H]+ = 577

[1675] 2) Synthesis of Int 129

[1676] Using the same equivalents and method as in the synthesis of Int 2, using Int 128 and 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)-5,6,7,8-tetrahydro naphthalen-2-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 129 (35.4 g, yield 73 %). MS [M+H]+ = 930

[1677] 3) Synthesis of Compound M66

[1678] Under a nitrogen atmosphere, Int 129 (25 g) and boron triiodide (17.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M66 (7.1 g, yield 28 %). MS [M+H]+ = 938

[1679] Synthesis Example 67. Synthesis of Compound M67

[1680]

[1681] 1) Synthesis of Int 130

[1682] Using the same equivalents and method as in the synthesis of Int 1, using 1-bromo-3-(tert-butyl)-5-chlorobenzene (30 g) and 12,12-dimethyl-5,12-dihydrobenzo[b]acridine (31.4 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 130 (38.9 g, yield 75%). MS [M+H]+= 427

[1683] 2) Synthesis of Int 131

[1684] Using the same equivalents and method as in the synthesis of Int 1, using Int 130 and N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine instead of Int 1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene], and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 131 (37.7 g, yield 74%). MS [M+H]+= 726

[1685] 3) Synthesis of compound M67

[1686] Under a nitrogen atmosphere, Int 131 (25 g) and boron triiodide (22.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M67 (7.2 g, yield 28%). MS [M+H]+= 734

[1687] Synthesis Example 68. Synthesis of compound M68

[1688]

[1689] 1) Synthesis of Int 132

[1690] Using the same equivalents and method as in the synthesis of Int 1, using 1-bromo-3-(tert-butyl)-5-chlorobenzene (30 g) and N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-2-amine (46.5 g) instead of 3-bromo-5-chloro-1,1'-biphenyl and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 132 (47.7 g, yield 72%). MS [M+H]+= 551

[1691] 2) Synthesis of Int133

[1692] Using the same equivalence and method as in the synthesis of Int2, Int132 and 1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole were used instead of Int1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-10H-spiro[acridin-9,9′-fluorene], and after the reaction was complete, the result was extracted and then recrystallized to obtain Int133 (30.3 g, 75% yield). MS[M+H]+=738

[1693] 3) Synthesis of compound M68

[1694] Under a nitrogen atmosphere, Int133 (25 g) and boron triiodide (22.6 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound M68 (7.1 g, yield 28%). MS[M+H]+=746

[1695] Synthesis Example 69. Synthesis of Compound M69

[1696]

[1697] 1) Synthesis of Int134

[1698] Under a nitrogen atmosphere, 2-bromo-4-chlorodibenzo[b,d]furan (30 g), di([1,1′-biphenyl]-4-yl)amine (43.2 g), sodium tert-butoxide (31 g), and bis(tri-tert-butylphosphine)palladium (0) (1.1 g) were introduced into toluene (600 ml) and refluxed for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain Int134 (41.1 g, yield 74%). MS[M+H]+=523

[1699] 2) Synthesis of Int135

[1700] Int134 (30 g), 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)-9H-carbazole (23.3 g), tripotassium phosphate (36.6 g), and bis(tri-tert-butylphosphine)palladium (0) (0.6 g) were introduced into 1,4-di The mixture was placed in alkane (300 ml) and water (100 ml) and refluxed for 6 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain Int135 (32.3 g, yield 73%). MS[M+H]+=766

[1701] 3) Synthesis of compound M69

[1702] Int 135 (25 g) and boron triiodide (21.8 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M69 (7.3 g, yield 29%). MS [M+H]+= 774

[1703] Synthesis Example 70. Synthesis of compound M70

[1704]

[1705] 1) Synthesis of Int 136

[1706] Using the same equivalents and method as in the synthesis method of Int 134, using 5,5,8,8-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)- 5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine instead of di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 136 (49.7 g, yield 71%). MS [M+H]+= 661

[1707] 2) Synthesis of Int 137

[1708] Using the same equivalents and method as in the synthesis method of Int 135, using Int 136 and N-(4-(tert-butyl)phenyl)-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)dibenzo[b,d] furan-2-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 137 (33.4 g, yield 78%). MS [M+H]+= 940

[1709] 3) Synthesis of compound M70

[1710] Int 137 (25 g) and boron triiodide (17.7 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M70 (7.1 g, yield 28%). MS [M+H]+= 948

[1711] Synthesis Example 71. Synthesis of compound M71

[1712]

[1713] 1) Synthesis of Int 138

[1714] Using the same equivalents and method as in the synthesis of Int 134, using N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro- naphtho[2,3-b]thiophen-3-amine instead of bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 138 (46.1 g, yield 73%). MS [M+H]+= 593

[1715] 2) Synthesis of Int 139

[1716] Using the same equivalents and method as in the synthesis of Int 135, using Int 138 and l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-di- o-tolyl-9H-carbazole instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 139 (33.2 g, yield 73%). MS [M+H]+= 904

[1717] 3) Synthesis of Compound M71

[1718] Under a nitrogen atmosphere, Int 139 (25 g) and boron triiodide (18.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M71 (7.1 g, yield 28%). MS [M+H]+= 912

[1719] Synthesis Example 72. Synthesis of Compound M72

[1720]

[1721] 1) Synthesis of Int 140

[1722] Using the same equivalents and method as in the synthesis of Int 134, using 3,6-di-tert-butyl-9H-carbazole instead of bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 140 (38 g, yield 74%). MS [M+H]+= 481

[1723] 2) Synthesis of Int 141

[1724] Using the same equivalents and method as in the synthetic method of Int 135, using Int 140 and 3-(dibenzo[b,d]furan-4-ylamino)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenol instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 141 (33 g, yield 73 %). MS [M+H]+= 720

[1725] 3) Synthesis of Int 142

[1726] Under a nitrogen atmosphere, Int 141 (25 g) and boron triiodide (23.2 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 142 (7.4 g, yield 29 %). MS [M+H]+= 728

[1727] 4) Synthesis of Int 142-2

[1728] Int 142 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-l-sulfonyl fluoride (2.6 ml) and potassium carbonate (4.0 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred at reflux for 2 hours. After completion of the reaction, the resultant was extracted, then column-purified to obtain Int 142-2 (9.1 g, yield 94 %). MS [M+H]+= 1010

[1729] 5) Synthesis of Compound M72

[1730] Under a nitrogen atmosphere, Int 142-2 (7 g), bis(4-(tert-butyl)phenyl)amine (1.8 g), pd(dba)2(0.11 g), Xphos (0.18 g) and cesium carbonate (6.3 g) were introduced into xylene (100 ml) and stirred at reflux for 12 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain Compound M72 (4.8 g, yield 76 %). MS [M+H]+= 991

[1731] Synthesis Example 73. Synthesis of Compound M73

[1732]

[1733] 1) Synthesis of Int 143

[1734] Using the same equivalents and method as in the synthesis of Int 134, using N-(5-(tert-butyl)-[1,1 '-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphtho[2,3-b]furan-3-amine instead of di([1,1 '-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 143 (54 g, yield 78%). MS [M+H]+= 653

[1735] 2) Synthesis of Int 144

[1736] Using the same equivalents and method as in the synthesis of Int 135, using Int 143 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-((5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)phenol instead of Int 134 and 3,6-di-tert-butyl-1 -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 144 (32.2 g, yield 77%). MS [M+H]+= 912

[1737] 3) Synthesis of Int 145

[1738] Int 144 (25 g) and boron triiodide (18.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 145 (7.3 g, yield 29%). MS [M+H]+= 920

[1739] 4) Synthesis of Int 145-2

[1740] Int 145 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1 -sulfonyl fluoride (2.1 ml) and potassium carbonate (3.2 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml) and stirred at reflux for 2 hours. After completion of the reaction, the resulting product was extracted, then column-purified to obtain Int 145-2 (8.8 g, yield 96%). MS [M+H]+= 1201

[1741] 5) Synthesis of compound M73

[1742] Int 145-2 (7 g), bis(4-(tert-butyl)phenyl)amine (1.7 g), pd(dba)2(0.11 g), Xphos (0.18 g), and cesium carbonate (5.7 g) were introduced into xylene (100 ml) under a nitrogen atmosphere, and stirred at reflux for 12 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain compound M73 (5.1 g, yield 74%). MS [M+H]+= 1183

[1743] Synthesis Example 74. Synthesis of compound M74

[1744]

[1745] 1) Synthesis of Int 146

[1746] Using the same equivalents and method as in the synthesis method of Int 134, using N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine instead of bis([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 146 (61.1 g, yield 73%). MS [M+H]+= 782

[1747] 2) Synthesis of Int 147

[1748] Using the same equivalents and method as in the synthesis method of Int 135, using Int 146 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 147 (27.1 g, yield 79%). MS [M+H]+= 889

[1749] 3) Synthesis of Int 148

[1750] Using the same equivalents and method as in the synthesis method of Int 134, using Int 147 (27 g) and 2-bromo-9,9-dimethyl-9H-fluorene (8.3 g) instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 148 (25.6 g, yield 78%). MS [M+H]+= 1080

[1751] 4) Synthesis of compound M74

[1752] Int 148 (25 g) and boron triiodide (15.4 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M74 (7.3 g, yield 29 %). MS [M+H]+= 1088.

[1753] Synthesis Example 75. Synthesis of compound M75

[1754]

[1755] 1) Synthesis of Int 149

[1756] Using the same equivalents and method as in the synthesis method of Int 134, using 1-bromo-3-chlorodibenzo[b,d]furan and N-(4-(tert-butyl)-2-methylphenyl)-5,5,8,8- tetramethyl-5,6,7,8-tetrahydro naphtho[2,3-b]thiophen-3-amine instead of 2-bromo-4- chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 149 (46.6 g, yield 72 %). MS [M+H]+= 607

[1757] 2) Synthesis of Int 150

[1758] Using the same equivalents and method as in the synthesis method of Int 135, using Int 149 instead of Int 134, and after completion of the reaction, the resultant was extracted and then recrystallized to obtain Int 150 (31.1 g, yield 74 %). MS [M+H]+= 850

[1759] 3) Synthesis of compound M75

[1760] Int 150 (25 g) and boron triiodide (19.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted and then recrystallized to obtain compound M75 (7.4 g, yield 29 %). MS [M+H]+= 858

[1761] Synthesis Example 76. Synthesis of compound M76

[1762]

[1763] 1) Synthesis of Int 151

[1764] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan instead of 2-bromo-4-chlorodibenzo[b,d]furan, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 151 (42.3 g, yield 76%). MS [M+H]+= 523

[1765] 2) Synthesis of Int 152

[1766] Using the same equivalents and method as in the synthesis of Int 135, using Int 151 instead of Int 134, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 152 (32.3 g, yield 73%). MS [M+H]+= 766

[1767] 3) Synthesis of Compound M76

[1768] Under nitrogen atmosphere, Int 152 (25 g) and boron triiodide (21.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M76 (7.5 g, yield 30%). MS [M+H]+= 774

[1769] Synthesis Example 77. Synthesis of Compound M77

[1770]

[1771] 1) Synthesis of Int 153

[1772] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N4,N4-diphenylbenzene-1,4-diamine instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 153 (55 g, yield 77%). MS [M+H]+= 670

[1773] 2) Synthesis of Int 154

[1774] Using the same equivalents and method as in the synthesis of Int 135, using Int 153 instead of Int 134, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 154 (31.2 g, yield 76%). MS [M+H]+= 913

[1775] 3) Synthesis of Compound M77

[1776] Int 154 (25 g) and boron triiodide (18.3 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M77 (7.3 g, yield 29%). MS [M+H]+=921

[1777] Synthesis Example 78. Synthesis of Compound M78

[1778]

[1779] 1) Synthesis of Int 155

[1780] Using the same equivalents and method as in the synthesis method of Int 135, using Int 151 and 3-([1,1'-biphenyl]-4-ylamino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- carbazole, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 155 (26.6 g, yield 79%). MS [M+H]+=748

[1781] 2) Synthesis of Int 156

[1782] Int 155 (25 g) and boron triiodide (22.3 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 156 (7.1 g, yield 28%). MS [M+H]+=756

[1783] 3) Synthesis of Int 157

[1784] Int 156 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.5 ml), and potassium carbonate (3.9 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml), and stirred at reflux for 2 hours. After completion of the reaction, the resultant was extracted, and then column-purified to obtain Int 157 (8.9 g, yield 93%). MS [M+H]+=1038

[1785] 4) Synthesis of Compound M78

[1786] Int 157 (7 g), bis(4-(tert-butyl)phenyl)amine (1.9 g), pd(dba)2(0.12 g), Xphos (0.19 g), and cesium carbonate (6.6 g) were introduced into xylene (100 ml) under a nitrogen atmosphere, and stirred at reflux for 12 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M78 (5.3 g, yield 77 %). MS [M+H]+= 1019

[1787] Synthesis Example 79. Synthesis of Compound M79

[1788]

[1789] 1) Synthesis of Int 158

[1790] Using the same equivalents and method as in the synthesis method of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and 3,6-di-tert-butyl-9H-carbazole instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 158 (38.7 g, yield 76 %). MS [M+H]+= 481

[1791] 2) Synthesis of Int 159

[1792] Using the same equivalents and method as in the synthesis method of Int 135, using Int 158 and N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)dibenzo[b,e][l,4]diazepine-2-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 159 (38.6 g, yield 73 %). MS [M+H]+= 844

[1793] 3) Synthesis of Compound M79

[1794] Int 159 (25 g) and boron triiodide (19.7 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M79 (7.3 g, yield 29 %). MS [M+H]+= 852

[1795] Synthesis Example 80. Synthesis of Compound M80 ​

[1796]

[1797] 1) Synthesis of Int 160

[1798] Using the same equivalents and method as in the synthesis of Int 135, using Int 158 and N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 160 (37.7 g, yield 75%). MS [M+H]+= 806

[1799] 2) Synthesis of compound M80

[1800] Under nitrogen atmosphere, Int 160 (25 g) and boron triiodide (20.7 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M80 (7.4 g, yield 29%). MS [M+H]+= 814

[1801] Synthesis example 81. Synthesis of compound M81

[1802]

[1803] 1) Synthesis of Int 161

[1804] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and 9,9-dimethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 161 (48.6 g, yield 75%). MS [M+H]+= 611

[1805] 2) Synthesis of Int 162

[1806] Using the same equivalents and method as in the synthesis of Int 135, Int 161 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine were used instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after the reaction was completed, the resulting product was extracted, then recrystallized to obtain Int 162 (34.5 g, yield 75 %). MS [M+H]+= 936

[1807] 3) Synthesis of compound M81

[1808] Under a nitrogen atmosphere, Int 162 (25 g) and boron triiodide (17.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After the reaction was completed, the resulting product was extracted, then recrystallized to obtain compound M81 (7.4 g, yield 29 %). MS [M+H]+= 944

[1809] Synthesis Example 82. Synthesis of compound M82

[1810]

[1811] 1) Synthesis of Int 163

[1812] Using the same equivalents and method as in the synthesis of Int 135, Int 161 and 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine were used instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after the reaction was completed, the resulting product was extracted, then recrystallized to obtain Int 163 (35 g, yield 74 %). MS [M+H]+= 964

[1813] 2) Synthesis of compound M82

[1814] Under a nitrogen atmosphere, Int 163 (25 g) and boron triiodide (17.3 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After the reaction was completed, the resulting product was extracted, then recrystallized to obtain compound M82 (7.5 g, yield 30 %). MS [M+H]+= 972

[1815] Synthesis Example 83. Synthesis of compound M83

[1816]

[1817] 1) Synthesis of Int 164

[1818] Using the same equivalents and method as in the synthesis of Int 135, using 2-chloro-N,N-bis(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalen-2-yl)phenyl)dibenzo[b,d]furan-4-amine and 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 164 (28 g, yield 75%). MS [M+H]+ = 930

[1819] 2) Synthesis of compound M83

[1820] Under nitrogen atmosphere, Int 164 (25 g) and boron triiodide (17.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M83 (7.1 g, yield 28%). MS [M+H]+ = 938

[1821] Synthesis Example 84. Synthesis of compound M84

[1822]

[1823] 1) Synthesis of Int 165

[1824] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 165 (36.3 g, yield 74%). MS [M+H]+ = 459

[1825] 2) Synthesis of Int 166

[1826] Using the same equivalents and method as in the synthesis of Int 135, using Int 165 instead of Int 134, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 166 (33 g, yield 72%). MS [M+H]+= 702

[1827] 3) Synthesis of compound M84

[1828] Under nitrogen atmosphere, Int 166 (25 g) and boron triiodide (23.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M84 (7.2 g, yield 28%). MS [M+H]+= 710

[1829] Synthesis example 86. Synthesis of compound M86

[1830]

[1831] 1) Synthesis of Int 169

[1832] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N4,N4-bis(4-(tert-butyl)phenyl)benzene-1,4-diamine instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 169 (59 g, yield 71%). MS [M+H]+= 782

[1833] 2) Synthesis of Int 170

[1834] Using the same equivalents and method as in the synthesis of Int 135, using Int 169 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 170 (32 g, yield 75%). MS [M+H]+= 1107

[1835] 3) Synthesis of compound M86

[1836] Int 170 (25 g) and boron triiodide (15.1 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain compound M86 (7.4 g, yield 29%). MS [M+H]+ = 1115

[1837] Synthesis Example 87. Synthesis of compound M87

[1838]

[1839] 1) Synthesis of Int 171

[1840] Using the same equivalents and method as in the synthesis method of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and 5,5,8,8-tetramethyl-N-(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen- 3-amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 171 (51.2 g, yield 74%). MS [M+H]+ = 647

[1841] 2) Synthesis of Int 172

[1842] Using the same equivalents and method as in the synthesis method of Int 135, using Int 171 instead of Int 134, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 172 (31 g, yield 75%). MS [M+H]+ = 890

[1843] 3) Synthesis of compound M87

[1844] Int 172 (25 g) and boron triiodide (18.7 g) were introduced into 1,2- dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain compound M87 (7.5 g, yield 30%). MS [M+H]+ = 898

[1845] Synthesis Example 88. Synthesis of compound M88

[1846]

[1847] 1) Synthesis of Int 173

[1848] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine instead of 2-bromo-4- chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 173 (53 g, yield 74%). MS [M+H]+ = 669

[1849] 2) Synthesis of Int 174

[1850] Using the same equivalents and method as in the synthesis of Int 135, using Int 173 and N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 9H-fluoren-2-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 174 (34 g, yield 76%). MS [M+H]+ = 994

[1851] 3) Synthesis of compound M88

[1852] Under nitrogen atmosphere, Int 174 (25 g) and boron triiodide (16.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M88 (7.3 g, yield 29%). MS [M+H]+ = 1002

[1853] Synthesis Example 89. Synthesis of compound M89

[1854]

[1855] 1) Synthesis of Int 175

[1856] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2- chlorodibenzo [b, d] furan and N- (5- (tert-butyl) - [1, 1 '-biphenyl] -2-yl) -5, 5, 8, 8- tetramethyl-5, 6, 7, 8-tetrahydronaphtho [2, 3-b] thiophen-2-amine instead of 2-bromo-4- chlorodibenzo [b, d] furan and bis ( [1, 1 '-biphenyl] -4-yl) amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 175 (52.4 g, yield 74%). MS [M+H]+ = 669

[1857] 2) Synthesis of Int 176

[1858] Using the same equivalents and method as in the synthesis of Int 135, using Int 175 and 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -10H-spiro [acridine-9, 9 '-fluorene] instead of Int 134 and 3, 6-di-tert-butyl-1- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H- carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 176 (33.2 g, yield 77%). MS [M+H]+ = 964

[1859] 3) Synthesis of Compound M89

[1860] Under a nitrogen atmosphere, Int 176 (25 g) and boron triiodide (17.3 g) were introduced into 1, 2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M89 (7.1 g, yield 28%). MS [M+H]+ = 972

[1861] Synthesis Example 90. Synthesis of Compound M90

[1862]

[1863] 1) Synthesis of Int 177

[1864] Using the same equivalents and method as in the synthesis of Int 134, using 4-bromo-2- chlorodibenzo [b, d] furan and N- (5- (tert-butyl) - [1, 1 '-biphenyl] -2-yl) -5, 5, 8, 8- tetramethyl-5, 6, 7, 8-tetrahydronaphtho [2, 3-b] thiophen-2-amine instead of 2-bromo-4- chlorodibenzo [b, d] furan and bis ( [1, 1 '-biphenyl] -4-yl) amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 175 (52.4 g, yield 74%). MS [M+H]+ = 669

[1865] 2) Synthesis of Int 178

[1866] Using the same equivalents and method as in the synthetic method of Int 135, using Int 177 and 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 2,3,4,4a,9,9a-hexahydro-lH-carbazole instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 178 (29.9 g, yield 73%). MS [M+H]+= 814

[1867] 3) Synthesis of compound M90

[1868] Under a nitrogen atmosphere, Int 178 (25 g) and boron triiodide (20.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain compound M90 (7.3 g, yield 29%). MS [M+H]+= 822

[1869] Synthesis example 91. Synthesis of compound M91

[1870]

[1871] 1) Synthesis of Int 179

[1872] Using the same equivalents and method as in the synthetic method of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and N-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)-7,7,10,10- tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-amine instead of 2-bromo-4- chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 179 (54.4 g, yield 73%). MS [M+H]+= 703

[1873] 2) Synthesis of Int 180

[1874] Using the same equivalents and method as in the synthetic method of Int 135, using Int 179 and 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 2,3,4,4a,9,9a-hexahydro-lH-carbazole instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 180 (28.4 g, yield 72 %). MS [M+H]+= 924

[1875] 3) Synthesis of compound M91

[1876] Under a nitrogen atmosphere, Int 180 (25 g) and boron triiodide (18.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resultant was extracted, then recrystallized to obtain compound M91 (7.2 g, yield 29 %). MS [M+H]+= 932

[1877] Synthesis example 92. Synthesis of compound M92

[1878]

[1879] 1) Synthesis of Int 181

[1880] Using the same equivalents and method as in the synthetic method of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and N-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalen-2-yl)dibenzo[b,d]fur-4-amine instead of 2-bromo-4- chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resultant was extracted, then recrystallized to obtain Int 181 (47.2 g, yield 76 %). MS [M+H]+= 585

[1881] 2) Synthesis of Int 182

[1882] Using the same equivalents and method as in the synthetic method of Int 135, using Int 181 and 5,5,8,8-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2- amine instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 182 (36.3 g, yield 75 %). MS [M+H]+= 938

[1883] 3) Synthesis of compound M92

[1884] Under nitrogen atmosphere, Int 182 (25 g) and boron triiodide (17.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M92 (7.4 g, yield 29 %). MS [M+H]+= 946

[1885] Synthesis example 93. Synthesis of compound M93

[1886]

[1887] 1) Synthesis of Int 183

[1888] Using the same equivalents and method as in the synthetic method of Int 135, using Int 151 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 183 (27.8 g, yield 77 %). MS [M+H]+= 630

[1889] 2) Synthesis of Int 184

[1890] Using the same equivalents and method as in the synthetic method of Int 134, using Int 183 (27 g) and 4-bromo-1,1 '-biphenyl (10.1 g) instead of 2-bromo-4-chlorodibenzo[b,d] furan and di([1,1 '-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 184 (25.4 g, yield 76 %). MS [M+H]+= 782

[1891] 3) Synthesis of compound M93

[1892] Int 184 (25 g) and boron triiodide (21.3 g) were introduced into 1,2- dichlorobenzene (250 ml) under nitrogen atmosphere and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted and then recrystallized to obtain compound M93 (7.5 g, yield 30%). MS [M+H]+= 790

[1893] Synthesis Example 94. Synthesis of compound M94

[1894]

[1895] 1) Synthesis of Int 185

[1896] Using the same equivalents and method as in the synthesis method of Int 134, using 4-bromo-2-chlorodibenzo[b,d]furan and bis(9,9-dimethyl-9H-fluoren-2-yl)amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 185 (48.5 g, yield 76%). MS [M+H]+= 603

[1897] 2) Synthesis of Int 186

[1898] Using the same equivalents and method as in the synthesis method of Int 135, using Int 185 and 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 186 (27.6 g, yield 78%). MS [M+H]+= 710

[1899] 3) Synthesis of Int 187

[1900] Using the same equivalents and method as in the synthesis method of Int 134, using Int 186 (27 g) and 4-bromo-l,l'-biphenyl (8.9 g) instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted and then recrystallized to obtain Int 187 (24.4 g, yield 74%). MS [M+H]+= 862

[1901] 4) Synthesis of compound M94

[1902] Under a nitrogen atmosphere, Int187 (25 g) and boron triiodide (19.4 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound M94 (7.1 g, yield 28%). MS[M+H]+=870

[1903] Synthesis Example 95. Synthesis of Compound M95

[1904]

[1905] 1) Synthesis of Int188

[1906] Using the same equivalences and methods as in the synthesis of Int135, Int158 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine were used instead of Int134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole, and after the reaction was complete, the result was extracted and then recrystallized to obtain Int188 (27.1 g, yield 74%). MS[M+H]+=588

[1907] 2) Synthesis of Int189

[1908] Using the same equivalences and methods as in the synthesis of Int134, Int188 (27 g) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (12.9 g) were used instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([1,1′-biphenyl]-4-yl)amine, and after the reaction was complete, the result was extracted and then recrystallized to obtain Int189 (26.6 g, 73% yield). MS[M+H]+=788

[1909] 3) Synthesis of compound M95

[1910] Under a nitrogen atmosphere, Int189 (25 g) and boron triiodide (21.1 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound M95 (7.2 g, yield 29%). MS[M+H]+=796

[1911] Synthesis Example 96. Synthesis of Compound M96

[1912]

[1913] 1) Synthesis of Int190

[1914] Using the same equivalents and method as in the synthesis of Int 134, using 3-bromo- 1-chlorodibenzo[b,d]furan and 9,9-dimethyl-9,10-dihydroacridine instead of 2-bromo-4- chlorodibenzo[b,d]furan and di([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 190 (34.5 g, yield 79%). MS [M+H]+= 411

[1915] 2) Synthesis of Int 191

[1916] Using the same equivalents and method as in the synthesis of Int 135, using Int 190 and 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)dibenzo[b,d]thiophen-3-amine instead of Int 134 and 3,6-di-tert- butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 191 (41.1 g, yield 74%). MS [M+H]+= 760

[1917] 3) Synthesis of Compound M96

[1918] Under nitrogen atmosphere, Int 191 (25 g) and boron triiodide (21.9 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Compound M96 (7.4 g, yield 29%). MS [M+H]+= 768

[1919] Synthesis Example 97. Synthesis of Compound M97

[1920]

[1921] 1) Synthesis of Int 192

[1922] Using the same equivalents and method as in the synthesis of Int 134, using 3-bromo- 1-chlorodibenzo[b,d]furan instead of 2-bromo-4-chlorodibenzo[b,d]furan, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 192 (43 g, yield 77%). MS [M+H]+= 523

[1923] 2) Synthesis of Int 193

[1924] Using the same equivalents and method as in the synthesis of Int 135, using Int 192 instead of Int 134, and after the reaction is complete, the resulting product is extracted, then recrystallized to obtain Int 193 (34.3 g, yield 78%). MS [M+H]+= 766

[1925] 3) Synthesis of compound M97

[1926] Under a nitrogen atmosphere, Int 193 (25 g) and boron triiodide (21.7 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction is complete, the resulting product is extracted, then recrystallized to obtain compound M97 (7.0 g, yield 28%). MS [M+H]+= 774

[1927] Synthesis Example 98. Synthesis of compound M98

[1928]

[1929] 1) Synthesis of Int 194

[1930] Using the same equivalents and method as in the synthesis of Int 134, using 3-bromo-1- chlorodibenzo[b,d]furan and bis(dibenzo[b,d]furan-2-yl)amine instead of 2-bromo-4- chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after the reaction is complete, the resulting product is extracted, then recrystallized to obtain Int 194 (42 g, yield 72%). MS [M+H]+= 551

[1931] 2) Synthesis of Int 195

[1932] Using the same equivalents and method as in the synthesis of Int 135, using Int 194 instead of Int 134, and after the reaction is complete, the resulting product is extracted, then recrystallized to obtain Int 195 (33.2 g, yield 77%). MS [M+H]+= 794

[1933] 3) Synthesis of compound M98

[1934] Under a nitrogen atmosphere, Int 195 (25 g) and boron triiodide (21 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After the reaction is complete, the resulting product is extracted, then recrystallized to obtain compound M98 (7.1 g, yield 28%). MS [M+H]+= 802

[1935] Synthesis Example 99. Synthesis of compound M99

[1936]

[1937] 1) Synthesis of Int 196

[1938] Using the same equivalents and method as in the synthesis of Int 134, using 3-bromo- 1-chlorodibenzo[b,d]furan and 9,9-dimethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalen-2-yl)-9H-fluoren-4-amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 196 (47.2 g, yield 73%). MS [M+H]+=611

[1939] 2) Synthesis of Int 197

[1940] Using the same equivalents and method as in the synthesis of Int 135, using Int 196 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-((5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amino)phenol instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 197 (33.1 g, yield 77%). MS [M+H]+=870

[1941] 3) Synthesis of Int 198

[1942] Int 197 (25 g) and boron triiodide (19.2 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 198 (7.2 g, yield 29%). MS [M+H]+=878

[1943] 4) Synthesis of Int 199

[1944] Int 198 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.2 ml) and potassium carbonate (3.3 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml), and stirred at reflux for 2 hours. After completion of the reaction, the resulting product was extracted, then column-purified to obtain Int 199 (8.8 g, yield 95%). MS [M+H]+=1160

[1945] 5) Synthesis of Compound M99

[1946] Int 199 (7 g), bis(4-(tert-butyl)phenyl)amine (1.7 g), pd(dba)2(0.11 g), Xphos (0.18 g), and cesium carbonate (6.0 g) were introduced into xylene (100 ml) under a nitrogen atmosphere, and stirred at reflux for 12 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M99 (5.4 g, yield 78 %). MS [M+H]+= 1141

[1947] Synthesis Example 100. Synthesis of Compound M100

[1948]

[1949] 1) Synthesis of Int 200

[1950] Using the same equivalents and method as in the synthesis method of Int 134, using 3-bromo-l-chlorodibenzo[b,d]thiophene instead of 2-bromo-4-chlorodibenzo[b,d]furan, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 200 (41.4 g, yield 72 %). MS [M+H]+= 539

[1951] 2) Synthesis of Int 201

[1952] Using the same equivalents and method as in the synthesis method of Int 135, using Int 200 and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5H-benzo[b]carbazole instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resultant was extracted, and then recrystallized to obtain Int 201 (28.8 g, yield 72 %). MS [M+H]+= 720

[1953] 3) Synthesis of Compound M100

[1954] Int 201 (25 g) and boron triiodide (23.1 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere, and stirred at 160°C for 4 hours. After completion of the reaction, the resultant was extracted, and then recrystallized to obtain Compound M100 (7.6 g, yield 30 %). MS [M+H]+= 728

[1955] Synthesis Example 101. Synthesis of Compound M101

[1956]

[1957] 1) Synthesis of Int 202

[1958] Using the same equivalents and method as in the synthesis of Int 134, using 1-bromo-3-chloro-9,9-dimethyl-9H-fluorene and bis(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-yl)amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 202 (43.3 g, yield 72%). MS [M+H]+= 617

[1959] 2) Synthesis of Int 203

[1960] Using the same equivalents and method as in the synthesis of Int 135, using Int 202 and N-([l,l'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-[l,l'- biphenyl]-4-amine instead of Int 134 and 3,6-di-tert-butyl-l-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 203 (34.3 g, yield 78%). MS [M+H]+= 902

[1961] 3) Synthesis of compound M101

[1962] Under nitrogen atmosphere, Int 203 (25 g) and boron triiodide (18.5 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160 °C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M101 (7.6 g, yield 30%). MS [M+H]+= 910

[1963] Synthesis Example 102. Synthesis of compound M102

[1964]

[1965] 1) Synthesis of Int 204

[1966] Using the same equivalents and method as in the synthesis of Int 134, using 1-bromo-3-chloro-9,9-dimethyl-9H-fluorene and N1-(5-(tert-butyl)-[l,l'-biphenyl]-2-yl)- N4,N4-bis(4-(tert-butyl)phenyl)benzene-l,4-diamine instead of 2-bromo-4- chlorodibenzo[b,d]furan and bis([l,l'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 204 (55.9 g, yield 71%). MS [M+H]+= 809

[1967] 2) Synthesis of Int205

[1968] Using the same equivalents and method as in the synthesis of Int 135, using Int 204 instead of Int 134, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int 205 (29.8 g, yield 76%). MS [M+H]+= 1052

[1969] 3) Synthesis of compound M102

[1970] Under a nitrogen atmosphere, Int 205 (25 g) and boron triiodide (15.8 g) were introduced into 1,2-dichlorobenzene (250 ml) and stirred at 160°C for 4 hours. After completion of the reaction, the resulting product was extracted, then recrystallized to obtain compound M102 (7.4 g, yield 29%). MS [M+H]+= 1060

[1971] Synthesis Example 103. Synthesis of compound M103

[1972]

[1973] 1) Synthesis of Int206

[1974] Using the same equivalents and method as in the synthesis of Int 134, using 1-bromo-3-chloro-9,9-dimethyl-9H-fluorene and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1,1,5,5,8,8-hexamethyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-3-amine instead of 2-bromo-4-chlorodibenzo[b,d]furan and di([1,1'-biphenyl]-4-yl)amine, and after completion of the reaction, the resulting product was extracted, then recrystallized to obtain Int206 (52 g, yield 76%). MS [M+H]+= 705

[1975] 2) Synthesis of Int207

[1976] Using the same equivalents and method as in the synthesis of Int 135, using Int 206 and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole instead of Int 134 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and after completion ...

Claims

1. A compound represented by the following chemical formula 1-1: [Chemical Formula 1-1] In chemical formula 1-1, R5 to R8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted aromatic hydrocarbon rings fused to aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic groups, or bonded to adjacent groups to form substituted or unsubstituted rings; Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring fused ring group; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form any of a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle and fused ring thereof containing N; At least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; and the remainder is hydrogen. R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted aromatic ring and aliphatic ring fused ring; or substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form any one of substituted or unsubstituted aromatic ring, substituted or unsubstituted aliphatic ring, substituted or unsubstituted heterocyclic ring, and fused ring thereof; Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or a group bonded to R4 to form any one of a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle and its fused ring containing N; and When Ar2 reacts with R5 to form benzo[a] When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring; At least one of R1 to R4 is bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, or at least one of R5 to R8 is bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

2. A compound represented by the following chemical formulas 1-2: [Chemical Formula 1-2] In chemical formulas 1-2, R5 to R8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted aromatic hydrocarbon rings fused to aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic groups, or bonded to adjacent groups to form substituted or unsubstituted rings; Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring fused ring group; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form any of a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle and fused ring thereof containing N; At least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; and the remainder is hydrogen. X1 is CRR', O, or S; A11 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; and R and R' may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to each other to form a substituted or unsubstituted ring, and When Ar2 reacts with R5 to form benzo[a] When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring.

3. The compound according to claim 2, wherein chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-6: [Chemical Formula 1-2-1] [Chemical Formula 1-2-2] [Chemical Formula 1-2-3] [Chemical Formula 1-2-4] [Chemical Formula 1-2-5] [Chemical Formula 1-2-6] In chemical formulas 1-2-1 to 1-2-6, X1, A11 and Z1 to Z3 have the same limitations as in chemical formulas 1-2; X3 to X6 may be the same as or different from each other, and each is independently CRR', NR'', O or S; Y2 is CG1G2, SiG8G9, NG101, O, or S; y2 is either 0 or 1, and when y2 is 0, Y2 is a direct bond; A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused cycloalkanes of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group. R, R' and R'' are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or they are bonded to each other to form a substituted or unsubstituted ring; R'5 to R'8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group; G1, G2, G7 to G12, G14, G15, G16 and G101 are the same as or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form substituted or unsubstituted aromatic rings, substituted or unsubstituted aliphatic rings, or substituted or unsubstituted aromatic and aliphatic rings; g7, g15, and g16 are each integers from 1 to 4; g10 is an integer from 1 to 8; g14 is 1 or 2; When g7, g10, g15 and g16 are each 2 or greater, the substituents in two or more brackets are the same or different from each other; When g14 is 2, the substituents in the two brackets are either the same or different from each other; Ar'1 and Ar'2 may be identical or different from each other, and each is independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; and In chemical formula 1-2-2, When y2 is 1 and Y2 is 0, G7 and R'6 to R'8 are hydrogen.

4. The compound according to claim 2, wherein R5 to R8 are the same or different from each other and are each independently hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or bonded to adjacent groups to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aliphatic ring having 3 to 30 carbon atoms; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic alkyl group having 6 to 30 carbon atoms; or an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic alkyl group having 6 to 30 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted with an arylamine group; a fused ring having 6 to 30 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted with a monocyclic or polycyclic heterocycle having 6 to 30 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted with a diarylamine group having 1 to 30 carbon atoms; Q3 and Q4 may be the same as or different from each other, and each independently consists of an unsubstituted or linearly or branched alkyl group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a fused ring group having a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Ar'1 is an unsubstituted or substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, selected from linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; or a fused monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. Cycloyl group; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to A1 to form an unsubstituted or linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms and containing N, a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, or a fused ring thereof; Ar2 is an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or substituted with any or more of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a fused ring consisting of an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. The group; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to R5 to form an unsubstituted or linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms and containing N, a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, or a fused ring thereof; At least one of Z1 to Z3 is deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic alkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or bonded to an adjacent group to form a monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused cyclic group of an aromatic ring and an aliphatic ring, and combinations thereof, and the remainder is hydrogen; Q5 and Q6 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, either unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group having a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; and When Ar2 reacts with R5 to form benzo[a] When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring.

5. A compound represented by any one of the following chemical formulas 1-1-1 to 1-1-3, 1-1-5 to 1-1-11, 1-1-13 to 1-1-27 and 1-1-29 to 1-1-36: [Chemical Formula 1-1-1] [Chemical Formula 1-1-2] [Chemical Formula 1-1-3] [Chemical Formula 1-1-5] [Chemical Formula 1-1-6] [Chemical Formula 1-1-7] [Chemical Formula 1-1-8] [Chemical Formula 1-1-9] [Chemical Formula 1-1-10] [Chemical Formula 1-1-11] [Chemical Formula 1-1-13] [Chemical Formula 1-1-14] [Chemical Formula 1-1-15] [Chemical Formula 1-1-16] [Chemical Formula 1-1-17] [Chemical Formula 1-1-18] [Chemical Formula 1-1-19] [Chemical Formula 1-1-20] [Chemical Formula 1-1-21] [Chemical Formula 1-1-22] [Chemical Formula 1-1-23] [Chemical Formula 1-1-24] [Chemical Formula 1-1-25] [Chemical Formula 1-1-26] [Chemical Formula 1-1-27] [Chemical Formula 1-1-29] [Chemical Formula 1-1-30] [Chemical Formula 1-1-31] [Chemical Formula 1-1-32] [Chemical Formula 1-1-33] [Chemical Formula 1-1-34] [Chemical Formula 1-1-35] [Chemical Formula 1-1-36] In chemical formulas 1-1-1 to 1-1-3, 1-1-5 to 1-1-11, 1-1-13 to 1-1-27 and 1-1-29 to 1-1-36, X2 to X9 may be the same as or different from each other, and each is independently CRR', NR'', O or S; Y1 and Y2 may be the same as or different from each other, and each is independently CG1G2, SiG8G9, NG101, O or S; y1 is either 0 or 1, and when y1 is 0, Y1 is a direct bond; y2 is either 0 or 1, and when y2 is 0, Y2 is a direct bond; R, R'' and R'' are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or they are bonded to each other to form a substituted or unsubstituted ring; R'1 to R'8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group; G1 to G19, G'13 and G101 are the same as or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted aromatic ring with aliphatic ring; or substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form substituted or unsubstituted aromatic ring; substituted or unsubstituted aliphatic ring; or substituted or unsubstituted aromatic ring with aliphatic ring; g3, g7, and g15 through g18 are each integers from 1 to 4; g4 and g10 are each integers from 1 to 8; g13 and g14 are each 1 or 2; g'13 is an integer from 0 to 2; g19 is an integer from 1 to 3; a21 is either 0 or 1; When g3, g4, g7, g10 and g15 to g19 are each 2 or larger, the substituents in two or more brackets are the same or different from each other; When g13, g'13 and g14 are each 2, the substituents in the two brackets are the same or different from each other; Ar'1 and Ar'2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring fused ring group; or a substituted or unsubstituted heterocyclic group; A2 and A21 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. At least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; and the remainder is hydrogen; and In chemical formulas 1-1-6, 1-1-8, and 1-1-32, When y2 is 1 and Y2 is 0, G7 and R'6 to R'8 are hydrogen.

6. The compound according to claim 2 or 5, wherein adjacent groups in Z1 to Z3 are bonded to each other to form a ring represented by the following chemical formula C-1 or C-2: [Chemical formula C-1] [Chemical formula C-2] In chemical formulas C-1 and C-2, J1 is O, S, NQ7, CQ8Q9 or SiQ10Q11; W1 to W8 and Q7 to Q11 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or a group bonded to an adjacent group to form a substituted or unsubstituted ring; and * indicates a site that bonds to any of the chemical formulas 1-2, 1-1-1 to 1-1-3, 1-1-5 to 1-1-11, 1-1-13 to 1-1-27, and 1-1-29 to 1-1-36.

7. A compound selected from any of the following: In the compound, t-Bu is tert-butyl.

8. An organic light-emitting device, comprising: First electrode; Second electrode; as well as One or more layers of organic material disposed between the first electrode and the second electrode. One or more of the organic material layers contain a compound according to any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound.

10. The organic light-emitting device of claim 8, wherein the organic material layer comprises a light-emitting layer, the light-emitting layer comprises a dopant material, and the dopant material comprises the compound.

11. The organic light-emitting device according to claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer further comprises a compound represented by the following chemical formula H: [Chemical formula H] In the chemical formula H, L20 and L21 may be the same as or different from each other, and each is a direct bond independently; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group; Ar20 and Ar21 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group; R200 and R201 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; and r201 is an integer from 1 to 7, and when r201 is 2 or greater, two or more R201 are the same or different from each other.

12. The organic light-emitting device of claim 10, wherein the light-emitting layer further comprises a host compound, and wherein at least one hydrogen atom at a substituted position is deuterated in the host compound.

13. The organic light-emitting device of claim 10, wherein the light-emitting layer further comprises a host and one or more types of dopants.

14. The organic light-emitting device of claim 10, wherein the light-emitting layer further comprises one or more types of bodies.

15. The organic light-emitting device of claim 10, wherein the light-emitting layer further comprises two or more types of hybrid bodies.

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